Ep. 34 - The Good Guys in a Not So Great Industry

1 - > SPEAKER_05: Maybe we can be the good guys in a not so great 2 - > industry. 3 - > SPEAKER_01: Yeah. 4 - > SPEAKER_02: I think like customers will find a way if 5 - > they think your business is unfair, they will find the way 6 - > to make to create fairness. 7 - > SPEAKER_05: Ultimately, serve there's really like one thing 8 - > driving us, which is ultimately like be the world's most loved 9 - > payments company and serve small business customers that are 10 - > being taken advantage of or not being well serviced like every 11 - > day.

12 - > SPEAKER_02: All right, let me get this story started. 13 - > So, so on paper, the story doesn't make sense. 14 - > In 2007, a 23-year-old web designer from Calgary looked at 15 - > one of the most conservative bank-dominated industries in the 16 - > world and decided that he wanted to enter the payments space. 17 - > Now there's phases to this because there's there's company 18 - > one and there's company two.

19 - > We're gonna talk about the evolution of that, but no 20 - > finance degree, no venture capital, no Silicon Valley 21 - > swagger, just the stubborn conviction that small businesses 22 - > were getting ripped off and someone needed to fix it. 23 - > I love the the the the the the the vigor of that step. 24 - > So Nick Beak, Nick Beak, French back, French background, you 25 - > know, French heritage, yeah, yeah, yeah. 26 - > SPEAKER_05: Grew up in Quebec.

27 - > SPEAKER_02: You grew up in Quebec. 28 - > Where in Quebec? 29 - > SPEAKER_05: Um, so Montreal Island, West Island. 30 - > SPEAKER_02: Montreal Island, West Island.

31 - > That's awesome. 32 - > I love I love Montreal. 33 - > Honestly, if there's any city I would live in aside from where 34 - > I'm living in, that would be Montreal. 35 - > SPEAKER_05: Except for the winters, the Montreal winters 36 - > are it says the Calgarian now.

37 - > Oh no, Montreal's much worse. 38 - > SPEAKER_02: It's it the ice, the iciness of Montreal. 39 - > SPEAKER_05: It's just heavy, heavy snow and it never lets up. 40 - > SPEAKER_02: It never lets up.

41 - > Yeah, yeah, yeah, yeah. 42 - > Um, so you founded Hellsom, a company that would spend, I 43 - > mean, two phases. 44 - > Phase phase one lasted how many years? 45 - > SPEAKER_05: So that was like from 2009 to 2020 or 19.

46 - > Not yeah. 47 - > And then we reinvented ourselves and relaunched a business in 48 - > 2020. 49 - > SPEAKER_02: Okay, so so Hellsom 2.0 is about five years.

50 - > Yep. 51 - > And Hellsom 1.0 It's kind of 11 years prior to that. 52 - > 11 years.

53 - > Um, and you you you had this mission around building an 54 - > ethical alternative to these payment goliaths that existed. 55 - > Because when you really look into this payment, everyone just 56 - > takes their piece. 57 - > If the small business owner is working hard to try and make 58 - > ends meet, and in that transaction of a customer 59 - > actually going to buy something, there are so many little pieces 60 - > taken away. 61 - > Um, and that that uh is is interesting.

62 - > Now there's a few Goliaths in this story, right? 63 - > The one that comes to mind in 2020 is sort of stripe and 64 - > square, the the sort of new fintech goliaths. 65 - > But early days, that's not the fintech goliath. 66 - > It's sort of Moneris?

67 - > It's sort of like where where where what who are the 68 - > competitors? 69 - > Who are the big Goliaths when you first get started? 70 - > SPEAKER_05: Yeah, it was the bank-owned processor kind of 71 - > legacy processors. 72 - > So you had Moneris and TD and Global Payments, and you know, 73 - > those kind of like old school processors that um dominated the 74 - > market, um, still dominate, you know, they're still giant 75 - > companies to this day.

76 - > The interesting part about payments is that nobody likes 77 - > their payments company, but number everybody needs to accept 78 - > payments. 79 - > Like it's it's a little bit like you know, the the you know, the 80 - > telephone companies where it's like everybody needs a phone, 81 - > but not everybody's in love with their their telephone companies. 82 - > And um we th we thought, hey, maybe there's maybe we can be 83 - > the good guys in a not so great industry. 84 - > SPEAKER_02: Maybe we can be the good guys in a not so great 85 - > industry.

86 - > I love that. 87 - > I I love that you you know that well because I've I've heard you 88 - > say that before. 89 - > So we're gonna quote you on that. 90 - > But let's be the good guys in the not so great industry.

91 - > I think one of the interesting things that we've learned in a 92 - > lot of these David versus Goliath stories as we've done 93 - > this research is that whenever there is excess fat that an 94 - > industry is sitting on, the consumer will will and and and 95 - > the the competition will find a way to eat away at it. 96 - > Yeah, right. 97 - > It's so it's sort of like blockbuster having you know 98 - > taken advantage of the the late fees. 99 - > Yeah, the late fees.

100 - > Yeah, right. 101 - > SPEAKER_05: Like I mean, there's that there's that quote from 102 - > Bezos, which is like, your margin is my opportunity, um, 103 - > which is like, I mean, he comes at it much more aggressively 104 - > from like a logistics and like massive cost reduction 105 - > standpoint. 106 - > But yeah, I mean, if whenever you have a service that 107 - > everybody needs, yet there's all these, you know, excessive 108 - > billing and excessive charges and like hidden fees and 109 - > everything like that, you have to ask yourself, like, why why 110 - > is that happening and why how is the what's the option in a 111 - > market if customers are like letting that happen to them?

112 - > SPEAKER_02: Yeah. 113 - > And and you like you came to a really interesting, I think, 114 - > insight, your sort of slingshot as as David. 115 - > One of your strategic insights was that radical transparency of 116 - > fee structure was more important than simplifying maybe the the 117 - > pricing page or the the fee structure. 118 - > That if I'm more transparent and give my buyer options, then it's 119 - > better than just like simplifying it because then they 120 - > can actually have more ownership, more agency over what 121 - > they want to spend.

122 - > SPEAKER_05: Yeah, it's it's it's weird that um it's a little like 123 - > counterintuitive because you would think that there's kind of 124 - > two ways to go about it. 125 - > You can have the kind of Silicon Valley way, which is very much 126 - > like make things very simple, which it can be very effective, 127 - > but it doesn't mean it's actually like affordable. 128 - > Yeah right. 129 - > Like the simplicity can actually be even more expensive, right?

130 - > Um, or you have the other way, which is how much do you 131 - > actually trust your customer? 132 - > How much do you trust that the average small business owner is 133 - > actually um you know sophisticated enough to be able 134 - > to kind of look at that, cut through that, and go like, no, 135 - > no, no, how much am I actually paying? 136 - > And can you put a more complicated rate structure in 137 - > front of them if it's um more affordable, which is what's me, 138 - > what we did, right?

139 - > Which is like a cost plus structure. 140 - > We said, like, here's the the raw, true wholesale cost with 141 - > Visa Mask card. 142 - > We're just gonna show it to you. 143 - > They're very complicated, show it to you.

144 - > And then we're just gonna charge you a kind of negotiated margin 145 - > on top, the way that like the big enterprise companies 146 - > operate. 147 - > And they it works in their favor as a big enterprise. 148 - > They use that model because it's it's what makes sense to them or 149 - > what reduces their costs. 150 - > But then everybody assumes, well, SMBs are too, they're 151 - > they're not smart enough to um to go for that model.

152 - > They'll just want a 2.9% flattened to worry about. 153 - > And it's like, I don't know, this this really hits their 154 - > margin. 155 - > This really matters.

156 - > I think you're underestimating the average like SMB operator. 157 - > Yeah. 158 - > And like, yeah, they will do their if it if it's costing them 159 - > an extra like 10,000 bucks a year, whatever, they will do 160 - > their homework. 161 - > SPEAKER_02: People do their homework.

162 - > SPEAKER_05: Yeah. 163 - > SPEAKER_02: I it's you know, again, I think I think this is 164 - > the insight. 165 - > So it's sort of the two pieces that I really like. 166 - > It's the consumer is smarter, and I'm gonna treat them like 167 - > that they're smarter.

168 - > I'm gonna give them that radical transparency, and your margins 169 - > are my opportunity. 170 - > Like I think those three together. 171 - > It reminds me of a like a funny little story I had the other. 172 - > I was a couple a couple weeks, a couple months ago, a couple 173 - > months ago now.

174 - > I was in I was in New York. 175 - > Uh, we I was doing a I was doing a fun gig for Chick-fil-A, the 176 - > speaking thing. 177 - > Yeah, it's kind of funny thing. 178 - > I was with my wife, we went down, we're having fun.

179 - > We we went to this little chapter, this is indigo chapters 180 - > right before the the day before, and um shopping around for 181 - > books, and then I had to go use the washroom. 182 - > So I go to use the washroom, and there's a sign on the washroom 183 - > door, and it says, um only customers allowed if you've 184 - > paid, like if you've paid. 185 - > And and there's a code, and you need to have a receipt for the 186 - > code. 187 - > And I was like, I just gotta use the washroom.

188 - > Like, I'm gonna buy something. 189 - > I've been in your store for 20 minutes. 190 - > I look over and there's like a little pile of receipts. 191 - > Customers were leaving their receipts next to the washroom 192 - > door because they felt like that policy was unfair to the and I 193 - > love that.

194 - > Yeah, I think like customers will find a way if they think 195 - > your business is unfair, they will find the way to make to 196 - > create fairness. 197 - > They go, let people use the washroom. 198 - > I literally picked up the receipt, I plugged it in, put 199 - > the receipt back for the next person to use it. 200 - > I was like, that's so you know, like, and I'm sure the staff 201 - > like come and clean that up every day, a few times a day 202 - > when they see it happening.

203 - > But I I like this because this is where this episode is going. 204 - > We're gonna get into how you how you had the conviction to start 205 - > a company like this because you are a tiny little David in 206 - > Canada, Calgary, to try to take on this massive industry. 207 - > You were 23 years old when you first started the first 208 - > business. 209 - > Obviously, you you matured in grade for the second, for the 210 - > second business, learned some good lessons along the way.

211 - > I want to kind of know the lessons of how David approaches 212 - > the fight, you know, day one versus how David approaches the 213 - > second fight. 214 - > Like I think that's an interesting piece. 215 - > And then how how some grows from this scrappy Calgary startup 216 - > culture, too. 217 - > I'm I'm interested in in how startups survive in the cold, 218 - > the the cold and maybe not as as money available, you know, uh 219 - > cities like Calgary versus right where everyone thinks like New 220 - > York or Toronto or the Valley, right?

221 - > Like where there's easier to to raise capital. 222 - > So that's where the that's where the story is gonna go. 223 - > That's where we're gonna really look into it. 224 - > So take me to 2007 and what is the insight that actually drives 225 - > this?

226 - > What's the moment? 227 - > Is there a moment? 228 - > What's the friend that you decide I'm gonna do this with? 229 - > Take me back to this this beginning, the beginning 230 - > origins.

231 - > SPEAKER_05: Yeah. 232 - > So um I started out as a geeky kid in the 90s that was really 233 - > into computers and what you you know in the late 90s, early 234 - > 2000s, what do you do with that if you're good with computers 235 - > and you're that kid? 236 - > You you build websites, right? 237 - > SPEAKER_01: So, like I was on Microsoft Paint.

238 - > SPEAKER_05: Yeah, there you go, right? 239 - > Um, and you you build websites for people, you you know, and I 240 - > would I was a teenager and I would go to my barber and the 241 - > local gym and different small businesses and just say, like, 242 - > I'd love to build you a website, and here's the work I've done. 243 - > And a lot of times they would say yes, and sometimes they'll 244 - > just write me a check on the spot and be like, How much do 245 - > you want? 246 - > And I'd be like, I don't know 500 bucks, 700 bucks, whatever.

247 - > And they would do it. 248 - > And that taught me a few things. 249 - > Um, I fell in love with small business in those moments where 250 - > it's like small business owners are like literally, there's no 251 - > reason to like write a check to a teenager that walks in your 252 - > door that says gonna build you something, but there's like a 253 - > camaraderie that immediately built, which is like these 254 - > people are risk takers and they believe in like supporting each 255 - > other, and there's like a kindred spirit.

256 - > And so I fell in love with with small business right there. 257 - > And that journey evolved into we started building more and more 258 - > websites and we started coding e-commerce websites. 259 - > This was kind of before the Shopify days. 260 - > SPEAKER_01: Well, yeah, yeah, yeah.

261 - > Who were what were you building on? 262 - > SPEAKER_05: No, it was uh uh like you would you'd find like 263 - > and you you'd host it yourself, so you'd like rack servers and 264 - > like I mean it's the old school days, right? 265 - > And then we started coding e-commerce websites, and then it 266 - > led into well, we got to plug in payments to those websites, and 267 - > that was like, so I'm in my my mid-20ness now, and we kept 268 - > seeing that, and there wasn't much, there was like PayPal and 269 - > Meneris.

270 - > SPEAKER_04: Yeah. 271 - > SPEAKER_05: Um, and it was awful. 272 - > Every time we tried to pass a business, they would like, you 273 - > know, PayPal's just PayPal's had a terrible reputation for like 274 - > 25 years, right? 275 - > And even the banks, like, you know, you'd you'd have to go 276 - > this convoluted process.

277 - > They wanted even I wanted to accept payments for my own 278 - > business so I can accept credit cards for the the work we were 279 - > doing. 280 - > And they wanted a$5,000 GIC and money down, and like it was just 281 - > this like, this is awful every time maybe there's an 282 - > opportunity. 283 - > And so we got in our heads, and we're like, no idea. 284 - > And this was me and and a co-founder at the time, and like 285 - > we we we're like, okay, we're gonna start a payments company.

286 - > The idea originally was like, we're gonna start we're gonna 287 - > mix our e-commerce with the payments, a little bit like 288 - > Shopify, right? 289 - > So it was like we're gonna build e-commerce websites, but then 290 - > we're gonna pair them with payments. 291 - > And now we don't know the terminology, we don't even know 292 - > what to ask for. 293 - > We're calling up literally calling a bank's cold and going, 294 - > like, I'd like to sell payments, please.

295 - > SPEAKER_02: And like, I'd like to plug you into our website. 296 - > SPEAKER_05: Yeah, it just did not like you know, so it was it 297 - > was a tough go, and it actually took two years of just trying to 298 - > call banks to do this. 299 - > SPEAKER_02: That's really interesting. 300 - > Oh, it was just like isn't that the story?

301 - > Like for so many founders, it took two years of just calling. 302 - > Yeah, just like I we don't even know what to call it, we don't 303 - > know what it is, I don't know how to Google it, I don't know 304 - > how to search it, I don't know how to talk about it. 305 - > But through enough conversations with bankers, yeah, the most 306 - > conservative of the bunch. 307 - > SPEAKER_05: And ironically, so we're you know, we're we're 308 - > we're Calgary kids trying to figure this thing out, and it 309 - > was actually an American bank that was expanding into Canada 310 - > that said, Hey, we have this this kind of reseller program, 311 - > you can sell payments, um, you know, you can you'll have some 312 - > control over it, and you can kind of build it into your your 313 - > your thing, or you, you know, and we got introduced somehow, 314 - > and and they said, Yeah, well, we'll they I think they were 315 - > desperate to grow into the Canadian market, and something 316 - > clicked, and it was the first one to say yes, and we just said 317 - > like yes on the spot.

318 - > Like my first yes, yeah, and and ironically, it came from a an 319 - > American partner, yeah. 320 - > SPEAKER_02: Um, that was willing that it shows you how 321 - > conservative the Canadian banks are, which is interesting 322 - > because wouldn't you what like I would argue that the Canadian 323 - > banks adopted digital faster than some of the American banks. 324 - > That is that an accurate. 325 - > SPEAKER_05: Yeah, but they're so monopolistic that they they 326 - > don't want to leave, they won't they don't want to let anyone 327 - > in.

328 - > So like it's kind of like even if you were to start a telephone 329 - > company in Canada versus the US, like it's gonna be easier there. 330 - > And and I'm obviously like I'm I'm a patriot, I'm super bullish 331 - > about Canadian and everything that's happening right now. 332 - > SPEAKER_02: We have some real log oligopolies here in Canada. 333 - > Oh, yeah.

334 - > SPEAKER_05: Banking and telephone, like it's just like 335 - > you can't get media, media, banking, telephone, right? 336 - > SPEAKER_02: Like it's it's it is controlled and it's they're the 337 - > Goliaths of these industries. 338 - > They are and they play defense, they actually play defense 339 - > aggressively. 340 - > Yes, yeah, it's aggressive defense, aggressive defense, 341 - > full court press is what they're doing.

342 - > Okay, so so you get your you get a first like uh opportunity to 343 - > resell this payment service from an American bank that you could 344 - > plug into your website. 345 - > Do they have plugins? 346 - > Are they like what are they do they have any of the like tech 347 - > to actually be the website? 348 - > No, no, no.

349 - > SPEAKER_05: You're just like you're ever you're coding 350 - > everything from scratch, um, it's super manual. 351 - > But then so we built um, so we're about to launch the first 352 - > payments company with the e-commerce piece, and we uh we 353 - > we decided to build a bunch of infrastructure that we needed to 354 - > plug in the payments to the e-commerce, right? 355 - > And like payment gateways and virtual terminals and things 356 - > like that. 357 - > And then so we launch and we got 49 clients in the first year, 358 - > and we're really happy.

359 - > And but then the feedback from the clients was like, yeah, your 360 - > software is fine. 361 - > We really like the payments piece. 362 - > And the payments piece is actually a little bit more of 363 - > the afterthought. 364 - > It was like the two are coming together, but we had built a lot 365 - > of these tools just to support the the e-commerce.

366 - > They're like, Yeah, uh, the e-commerce, I don't know if I'll 367 - > use it or not, but like, can I keep the payments? 368 - > Can I use more of the payments? 369 - > And it was this realization. 370 - > SPEAKER_02: Were you charging for the e-commerce?

371 - > Or were you charging for the payments? 372 - > SPEAKER_05: We're charging for both. 373 - > Okay, yeah. 374 - > And um, it was this realization it's like, hey, maybe we're 375 - > better at payments.

376 - > Maybe maybe this is like what we'd be uh good at. 377 - > So we decided to to to shift our focus and be like, let's let's 378 - > do that. 379 - > And that's how that was like the start of the first payments 380 - > company. 381 - > unknown: Cool.

382 - > SPEAKER_02: And and and that's an interesting insight because 383 - > you you're you you hear it from your customers, you hear it from 384 - > the first ones. 385 - > They go, This is what we like as part of your product, this is 386 - > what we enjoy. 387 - > What did they say they liked about it? 388 - > What was it?

389 - > Just like this was easy, I have no other solution because there 390 - > wasn't any, was there a lot of things? 391 - > SPEAKER_05: No, like I mean so this is like 2019, 2000 or 392 - > sorry, 2009, 2010. 393 - > Stripe came out, 2011. 394 - > It was still like like the early days of that world, right?

395 - > So we created something that was like super simple. 396 - > And then when it came to the our pricing approach, even that 397 - > early in that came from inside, which was like we want to be the 398 - > good guys in a not so great industry. 399 - > So we're like, let's make it transparent, let's make it 400 - > honest. 401 - > Now it was there from like they won.

402 - > Yes, and I think they resonated with that because the industry 403 - > was nothing but right. 404 - > SPEAKER_02: And so initially, I guess you got this funded and 405 - > started because you were building websites and e-commerce 406 - > stores. 407 - > That was your initial capital. 408 - > You were fee for service, you're just professional services, and 409 - > then you build this tool, and now you're like, okay, maybe we 410 - > can just now are you selling it as a initially as like a SaaS 411 - > membership license, or were you always you know taking a portion 412 - > of transactions?

413 - > SPEAKER_05: Always a portion of transactions. 414 - > There was a basic kind of monthly fee. 415 - > And so we shifted to that, and um the the there's no funding, 416 - > there's no capital. 417 - > There's I didn't know what the word VC was.

418 - > Yeah, yeah. 419 - > I'm a Calgary. 420 - > I didn't even know what the word startup was. 421 - > I'm just a Calgary tech business owner, and you know, we're gonna 422 - > go and have to like funding.

423 - > SPEAKER_02: Like I have to sell something to get money. 424 - > SPEAKER_05: Yeah, they that's and then it was so it was get, 425 - > you know, get two classes, get four, get eight, you know, get 426 - > 16, and like, you know, keep growing as slowly and get to the 427 - > point where like it the first few years were slow. 428 - > Like we were it took a few years for us to be able to like give 429 - > ourselves a basic salary, and we're just kind of grinding it 430 - > away.

431 - > But we were building a small business and building a 432 - > reputation locally as like good payments guys. 433 - > SPEAKER_02: I mean, that's the beauty of starting in your early 434 - > 20s. 435 - > You don't need much, right? 436 - > You're like, what?

437 - > I don't I don't even need that much. 438 - > What's a you know a basic salary? 439 - > I don't even know. 440 - > SPEAKER_05: I'm super thankful for my wife because she's 441 - > carried me for a long time.

442 - > She carried me for a long time. 443 - > SPEAKER_02: So we have a I have a term, we have a term for it. 444 - > We call it uh uh the founder founders, partners who who 445 - > carry. 446 - > They're the steady Freddies.

447 - > Yeah, like that's awesome. 448 - > So shout shout out to your wife. 449 - > What's your wife's name? 450 - > Leslie.

451 - > Leslie. 452 - > Thank you, Leslie, for giving us giving us Nick, you know? 453 - > So, so okay, you have this moment where you realize this is 454 - > this is the opportunity. 455 - > You start building towards it.

456 - > It takes three years before you're you're making enough 457 - > revenue to pay yourself. 458 - > What what is what is the three, four year, what does that look 459 - > like? 460 - > Uh uh at five years. 461 - > Um, what do you have?

462 - > Is it a few staff? 463 - > Is it you and the founders? 464 - > How many how many clients? 465 - > SPEAKER_05: Yeah, so we got to about like uh three three staff 466 - > and two two founders.

467 - > Um, and then uh there's uh uh my co-founder left. 468 - > Um, so then it was like me and the business, right? 469 - > Um and it wasn't like at the time, it was just like it was 470 - > just a small business, you know, you buy yourself a job, exactly, 471 - > right? 472 - > And it's like, okay, you know, been doing that for with me for 473 - > for four or five years, and it's like, okay, we got at this 474 - > point, but you know, like you know, change change of heart 475 - > kind of thing, right?

476 - > Yeah, and um we this is so I go to I so this is like 2014 or so, 477 - > and I still have it for me. 478 - > I'm like, no, no, no, I think I think I can get this to a 479 - > bigger, yeah, bigger stage, and um, but we're still a reseller 480 - > of the bank. 481 - > So we're still like you know still skimming on top of the 482 - > skim. 483 - > Like it's yeah, and and and and you're still like we're 484 - > controlling, we have great customer service, we have good 485 - > reputation, we're trying to be honest with pricing, but when I 486 - > say trying to be honest with pricing, because you're still 487 - > navigating the bank.

488 - > Yes, and they're you know, you're you're saying, No, no, 489 - > no, I don't think we should charge these fees. 490 - > The bank's like, well, that's what we charge. 491 - > And then so then you're like you're trying to make up for it 492 - > with even better customer service and even you know better 493 - > tools to kind of make up for that. 494 - > So you always feel like you're in the shadow.

495 - > And that was really tough. 496 - > And I I saw what was happening. 497 - > SPEAKER_02: How can you do good when you are strapped to the 498 - > Goliath, to the person doing bad? 499 - > Like exactly.

500 - > I'm just the other side of their coin. 501 - > SPEAKER_05: And uh the best analogy I have is like if you're 502 - > uh an insurance broker, so it's kind of like you could have 503 - > right insurance brokers with like fantastic reputations, they 504 - > could take their custom they could take care of their 505 - > customers, people refer to them like he should you know find my 506 - > my you know, use my friend, but ultimately you're still at the 507 - > mercy of like the insurance companies, yeah, and whether 508 - > they actually want to pay out or yeah, exactly, and how they 509 - > ultimately achieve customers and how they ultimately price 510 - > policies and everything.

511 - > So that's probably like the closest analogy where like we 512 - > were building a really good reputation, but still under the 513 - > limits of being in the shadow of a bigger um kind of bank, right? 514 - > SPEAKER_02: Well, and the regulations here in Canada, like 515 - > how like you know, one of the the pieces that one of the when 516 - > when when studying wealth simple story, for example, that I that 517 - > I learned that what they they actually uh early on acquired an 518 - > existing uh small kind of player bank that already had their 519 - > licensing because it would have taken too long to get the 520 - > licensing to actually move forward.

521 - > Yeah, like they but they have to have the pockets to do that. 522 - > And they were raising yeah, yeah, they they had the pockets 523 - > different. 524 - > But it was interesting, like the regulation here in Canada. 525 - > So were you facing any regulation issues?

526 - > That's why you sort of had to stick with the bank for a while. 527 - > SPEAKER_05: It's not really regulation as much as like 528 - > obviously we have regulations, we have like uh thing frameworks 529 - > we have to operate under, but the main thing is just like a 530 - > bank has to open a door for you, period. 531 - > You cannot ask you cannot act access Visa Master to interact 532 - > in those networks, you just can't access them without a bank 533 - > connecting you to them.

534 - > Yeah, so now okay, we're mid-2010s, the business is 535 - > starting to accelerate. 536 - > Um, still the the the kind of reselling business but organic 537 - > growth, reputation, starting to get better at marketing and 538 - > everything, right? 539 - > So starting to grow and it grew pretty well. 540 - > So, like in the next five years, all the way 2019, we grew to 541 - > about 40 people.

542 - > So we're like 40 staff, 6,000 customers. 543 - > This thing's becoming a real thing. 544 - > Um, again, it's all bootstrapped. 545 - > SPEAKER_02: All bootstrapped 40 staff, yeah, 6,000 customers.

546 - > That's huge, that's that's amazing. 547 - > That's an amazing small, medium-sized business. 548 - > SPEAKER_05: Like, that's it's it's but you know, you're then 549 - > I'm starting to see what's happening in the market. 550 - > So I'm seeing like, oh, Square is starting to really like grow 551 - > and Stripe is starting to become dominant, and like, and they 552 - > have different licenses than I do because I'm just a reseller 553 - > under the bank's shadow, and they were giving a license to 554 - > essentially operate and kind of be their own payments company, 555 - > their own processor, right?

556 - > Yeah, and I'm so they were their relationship directly with Visa 557 - > MasterCard and yeah, and you still it's funny because you're 558 - > still even in that world of payments, you're still got a 559 - > bank kind of backstopping you, but they are being giving very 560 - > different licenses to kind of do it on their own, right? 561 - > So seeing what's happening, so the the the the the bootstrap 562 - > business starting to grow. 563 - > Um Um starting to be more meaningful.

564 - > I'm starting this this this bank relationship uh that we have 565 - > down in the US. 566 - > Um I'm starting to, you know, it's a it's a good relationship 567 - > that I'm building and they're trusting me more and more, and 568 - > the business is becoming more significant. 569 - > And I go to them and I go, like, this has served us both well. 570 - > Yeah, but I need to move away from your shadow, and I want to 571 - > go on my own and and do this, right?

572 - > SPEAKER_02: How do they feel about that? 573 - > SPEAKER_05: Um, I think that banks, regardless of the great 574 - > partnership or not, like nobody wants to wholesale their 575 - > business, nobody wants to like create competitors out of 576 - > nowhere. 577 - > Um, but we grew to a certain size where uh we said, look, 578 - > we're I'm gonna I'm gonna get back on the phone for two years 579 - > and I'm gonna find a new way to do this. 580 - > Yes.

581 - > And I would love for you to be that partner, but you're gonna 582 - > have to make a a call, right? 583 - > And um they finally said yes. 584 - > And you know, they but they said, you know, first one 585 - > through the door gets bloody, and like it's gonna be, and so 586 - > we got the yes in 2017. 587 - > SPEAKER_02: And from and and they what was the what the yes 588 - > was like we want you they're gonna give us this license to go 589 - > on our own, okay, right?

590 - > SPEAKER_05: So essentially to be our own payments company where 591 - > we are in charge of everything A to Z. 592 - > SPEAKER_02: That's it. 593 - > SPEAKER_05: But also also the rest of the city. 594 - > SPEAKER_02: And you're paying for that license.

595 - > SPEAKER_05: Yeah, exactly. 596 - > Right. 597 - > So um, and you know, everything is your responsibility, like 598 - > risk, moving the money, all like technology, hardware, it doesn't 599 - > matter. 600 - > Like it's all yours.

601 - > If you want the keys, fine, we'll give you the keys. 602 - > SPEAKER_02: But like uh yeah, we're washing our hands of this 603 - > exactly, right? 604 - > SPEAKER_05: And um, so we go, okay, great, like this is gonna 605 - > be the this is the chance to kind of reinvent ourselves and 606 - > ultimately it's it's about our small business customers, like 607 - > really like fell in love with those original small business 608 - > owners and wanting to like be able to like fully actualize 609 - > that mission that I had in my head, which is like to be the 610 - > world's most left payments company, which is an oxymoron.

611 - > Um, but I'm like, we're never gonna do it under the shadow of 612 - > a bank, we're gonna have to go on our own and ultimately like 613 - > bring this to the market the way that like we think it like even 614 - > with Square Even a Stripe, even with everybody in the market, 615 - > like they weren't doing it the way I think it should have been 616 - > done for the small businesses. 617 - > Yeah, and the only way for us to do it is to go on our own and 618 - > try to do that.

619 - > SPEAKER_02: So what do you do? 620 - > What do you do now with this new is this this is this is so the 621 - > new license is the birth of Hellsome 2.0. 622 - > SPEAKER_05: Yeah.

623 - > So get this license 2007, or get sorry, get the thumbs up that 624 - > we're gonna get this license in 2007. 625 - > SPEAKER_02: Okay, yeah, there's some time between the thumbs up 626 - > and the execution. 627 - > SPEAKER_05: In my mind, I'm like, okay, I've got this 628 - > business, it's profitable, it's bootstrapped, right? 629 - > I want to do this giant, giant pivot to essentially be reinvent 630 - > ourselves as a company.

631 - > Um, this the my bank partner's telling me it's gonna give me 632 - > this license, yeah, but I gotta convince their, and this is like 633 - > kind of the first one through the door gets bloody. 634 - > So it's like I gotta convince their compliance officers, 635 - > they're legal, get everything in place, get everybody happy and 636 - > and and regulations and everything, right? 637 - > And we're still just a small Calgary bootstrap company. 638 - > Yeah, yeah.

639 - > Um, and we still gotta like, yeah, we have a basic outline of 640 - > a payment service, but like we're about to take on 641 - > everything ourselves. 642 - > So we gotta go build a ton of stuff, and I gotta find a 643 - > manufacturer for my hardware. 644 - > I gotta build like a ton of systems. 645 - > SPEAKER_02: Well, you're not just building a software 646 - > company.

647 - > No, you're it's it's making hardware. 648 - > SPEAKER_05: Like somebody from Calgary with like a small little 649 - > business is no business trying to make a competitor to like. 650 - > Maybe that's why they agreed. 651 - > SPEAKER_02: You know, that's like go get your ear, try it.

652 - > Yeah. 653 - > SPEAKER_05: So in my mind, I'm like, okay, so what I I mean, 654 - > the hurdle is huge. 655 - > Yeah. 656 - > SPEAKER_02: I think there's a there is, there's, there's who 657 - > said it?

658 - > I think it was it was um um CEO of Nvidia Jensen there. 659 - > He goes, If I if I truly knew and understood what it would 660 - > have taken, I would have never done it. 661 - > SPEAKER_05: Yeah. 662 - > I remember seeing that quote.

663 - > You have to be, I mean, there's certain industries, I'm sure 664 - > like building chips is definitely one of those, right? 665 - > Where it's like you kind of have to be like a is the term 666 - > masochist? 667 - > Like you just like you just have to like enjoy pain somehow at 668 - > some deep level. 669 - > Yeah.

670 - > Um, so yeah, we we bid off way more than we could chew, but 671 - > we're like, we are doggily determined to prove the market 672 - > that we could do this. 673 - > SPEAKER_02: And are you aware of your how aware are you of the 674 - > competitors, like of Goliath? 675 - > I find sometimes some people are like, you know what, we weren't 676 - > even really aware of our competitors. 677 - > We were sort of just doing our own thing, want to solve this 678 - > problem.

679 - > SPEAKER_05: We looked at the market differently. 680 - > So, like you had Square, you know, uh, but Square is really 681 - > focused on like restaurants, and that's where people kind of see 682 - > it, right? 683 - > Stripe and both have done fantastically well, but Stripe 684 - > is more like tech companies, and they want to find the Shopify's 685 - > and the Uber. 686 - > SPEAKER_02: They wanted to find, yeah, exactly.

687 - > They didn't want to be the front line. 688 - > SPEAKER_05: Yeah, and then for us, we like call it like real 689 - > main street business. 690 - > So like we wanted to help dentists and vets and auto 691 - > mechanics and wholesalers and accountants, and like they're 692 - > not, you know, those those those small businesses were still not 693 - > being like um serviced by the new no by by those new 694 - > processors, they're still stuck with the bank. 695 - > SPEAKER_02: All the old POS systems, yeah, yeah, yeah.

696 - > SPEAKER_05: And there's a lot of them. 697 - > It's a giant to give you a sense of the market. 698 - > Square, which is like fantastically big, right? 699 - > Like$50 billion market cap has two percent of the market.

700 - > SPEAKER_02: Oh, I didn't know that. 701 - > That's that's interesting. 702 - > SPEAKER_05: Stripe is five percent, JP Morgan Chase, which 703 - > is largest. 704 - > Shopify.

705 - > SPEAKER_02: Shopify, yeah, which is the quarter of their 706 - > business. 707 - > Yeah, which is their quarter of their business. 708 - > SPEAKER_05: And then wow. 709 - > And then JP Morgan is nine percent of the business.

710 - > So it gives you this sense of like it's immense, it's infinite 711 - > TAM. 712 - > Um, but it's also massive barriers to entry. 713 - > SPEAKER_04: Yes. 714 - > SPEAKER_05: So we go, okay, we want to do this.

715 - > And you know, to go back to your question, like, no, we I don't 716 - > think we I don't think I was realizing how much I was buying 717 - > at all. 718 - > It was like, I'll be fine. 719 - > SPEAKER_02: Um the naivity of David is what allows him to be 720 - > just illusional enough. 721 - > Yeah, because you wouldn't start it.

722 - > You want to start it. 723 - > Like I think that, but I also think that's why often you see 724 - > startups happen with people in their youth, in the younger 725 - > because it again, the naivety of I can do that, I can pull that 726 - > off. 727 - > We could, you know, like totally. 728 - > SPEAKER_05: And so we we're in this point, so we do a couple of 729 - > things.

730 - > So we think it's gonna take this, we think it's like this is 731 - > gonna take 12 months. 732 - > It did not take 12 months, it took three years. 733 - > Um, so this is like the 2000. 734 - > So we we we launched Hellsome 2.

0, like reinvented ourselves 735 - > in 2020 essentially as a new company. 736 - > What happens between then those three years is a couple of 737 - > things. 738 - > It took us three years to actually convince the banks and 739 - > the regulators to let us do this. 740 - > Yeah, so it it it took a long time and a whole lot of work to 741 - > do that, right?

742 - > Um, it took us three years to uh code and build the hardware and 743 - > like so the the technology was differ but it's brand new. 744 - > SPEAKER_02: Yeah, you you essentially did not have the 745 - > technology before. 746 - > Yeah, we only have we have 10% of it. 747 - > You get 10% of it, yeah.

748 - > SPEAKER_05: And you know, finding manifests. 749 - > Both hardware and software, yeah. 750 - > So like so it took us three years, and and we're like, how 751 - > do we fund this thing? 752 - > Yeah, we have a small boost.

753 - > SPEAKER_02: What about the customers? 754 - > Were you able to keep the same customer? 755 - > SPEAKER_05: Only a small portion of it. 756 - > Okay.

757 - > And I was part of negotiations and everything. 758 - > And we looked at like when we launched the service 2020, there 759 - > was a lot of things that we didn't have that the bank used 760 - > to have, right? 761 - > SPEAKER_02: Um, so we actually So you had a uh a shittier 762 - > product to a smaller market with no capital and uh and less 763 - > technology built up. 764 - > But we were on our own.

765 - > But but you were unshackled, yes. 766 - > And so that is really interesting because so you you 767 - > were no longer capped, but you had bigger barriers. 768 - > Yes. 769 - > SPEAKER_05: That's exactly it.

770 - > And we so what we did is that we the old, you know, like a 771 - > certain like a big portion of our book of business, the bank 772 - > bought from us and that gave us some cash. 773 - > So we kind of became our own kind of seed investor. 774 - > SPEAKER_02: Okay, yeah, you got your initial initial capital 775 - > injection. 776 - > SPEAKER_05: And and so the old kind of we kind of the 777 - > cannibalized the old business.

778 - > Are you comfortable sharing it? 779 - > Like, was there what was the initial capital injection? 780 - > A couple million bucks. 781 - > Yeah, nothing too big, right?

782 - > And um, and then for a business I had built 10 years prior 783 - > building, and then you're like, I'm gambling it all, I'm putting 784 - > all on the line, I've taken no money from myself, and I'm 785 - > starting back at zero. 786 - > And man, I hope this works because the first 10 years was 787 - > literally, you know, there's nothing being taken out for 788 - > yourself. 789 - > It's purely just like a a something that's about to be 790 - > cannibalized to restart from scratch, but to be on your own.

791 - > And I hope it works out. 792 - > Yeah, the risk level, like hindsight, I'm like, oh man, 793 - > like you took it all. 794 - > SPEAKER_02: You took it all, you didn't like and put it back in. 795 - > Like that is, that is, you know, there's a there's a um, I say, 796 - > like you, you know, you want to you make you want to make 797 - > hundreds of thousands, you gotta gamble tens of thousands.

798 - > You want to make millions, you gotta gamble hundreds of 799 - > thousands. 800 - > You want to make tens of millions, you gotta gamble 801 - > millions. 802 - > SPEAKER_05: Yeah. 803 - > And um, so and then we hired a bunch of junior developers out 804 - > of like local Calgary junior developers.

805 - > We hired 15 of them. 806 - > And so I'm a self-top coder, so we just coded for three years 807 - > straight. 808 - > Millions of lines of code, just like day and night, with all 809 - > these junior devs out of college, and and just like but 810 - > no vibe coding. 811 - > No, yeah, no way, no vibe coding.

812 - > You know, what's funny on the you know, now we have a good 813 - > mixture of like different senior and experienced developers that 814 - > help our juniors and everything like that. 815 - > In hindsight, again, I don't know if we would have taken on 816 - > the challenge. 817 - > We could have brought in a couple like experienced like 818 - > Shop 5 folks and be like, there's no way. 819 - > SPEAKER_02: Like it's just like this, this is the it's too 820 - > insurmountable.

821 - > SPEAKER_05: Because we coded this with like 15 junior coders, 822 - > and we just kind of went like but but nobody could tell us 823 - > your tech debt must still be a little bit it's honestly it's a 824 - > whole lot better than you think it would be, but I think we made 825 - > some good decisions early. 826 - > So we got lucky. 827 - > But the yeah, so we we went through this process and in 828 - > 2020, we're like, holy crap, I think it's it's it's ready. 829 - > Um, and it better be because we are now burning our own cash, 830 - > that's seed money.

831 - > Um, we've just sold most of our customers back to the bank. 832 - > We're back, we're essentially we have no investors. 833 - > We're we're burning our own cash, and like we're back at 834 - > almost zero revenue. 835 - > Like, this better work.

836 - > unknown: Wow. 837 - > SPEAKER_02: Um in those three years, in that three years, 838 - > that's where it, yeah. 839 - > SPEAKER_05: Yeah, and then so now it's 2020, the pandemic 840 - > starts, and we're going, we're ready to launch. 841 - > SPEAKER_02: That's a good that's a good wave, is it?

842 - > Is it's a medium for us because like dentists and doctors and 843 - > like there's the all of the front, okay, all of the yes, all 844 - > the brick and mortar is down, online on payments move online. 845 - > SPEAKER_05: So I think call it like a neutral mix. 846 - > Yes, yeah, for us. 847 - > SPEAKER_02: Yeah, yeah, yeah, yeah.

848 - > How does your team how does your team react to that moment? 849 - > What is the what what's the feeling? 850 - > I mean, there's the you know, feeling that we all had of like 851 - > what is going on? 852 - > Is it just two weeks?

853 - > It's four weeks, it's six weeks, okay. 854 - > What you know, is life ending? 855 - > Like there's there's a few existential feelings, I'm sure, 856 - > but what is the feeling in the team in that moment from a 857 - > business perspective? 858 - > SPEAKER_05: I think it's excitement because I think that 859 - > the some of the OGs that were with us like knew knew the 860 - > frustrations of being under the shadow of a big bank.

861 - > Yeah and you know, we were all really eager to go out on our 862 - > own and prove to the world that we're like we could do it on our 863 - > own. 864 - > Um also daunting. 865 - > I think that like I remember that like we we created this 866 - > like war room with the deaths, um where um when new merchants 867 - > signed up, like this is like the first data, first month of 868 - > launch and everything for the new service. 869 - > Like all of a sudden we're responsible for risk and fraud 870 - > and everything.

871 - > Like we've licked, we took on everything. 872 - > Yeah, so we just to like kind of create that that that that 873 - > safety and the group feeling. 874 - > Um, you know, we have our our head of risk. 875 - > It's like we've been preparing and we have policies, we have 876 - > processes, but it's like this is never like happened on our own, 877 - > right?

878 - > It's very different than when you're you're being shadowed by 879 - > a bank versus doing it on your own. 880 - > So for the first month, we literally had this like big 881 - > table, and everybody sat like the executive, my CFO, my CO, 882 - > everybody like we're just sitting around this table and 883 - > we're just making approval and decline decisions together as a 884 - > group. 885 - > Uh, just to like, yeah, we have our process, we have our 886 - > systems, but just to like part of the reason I I did that was 887 - > to try to like make it feel less scary.

888 - > Yes, because everybody was like scared to death. 889 - > Yes, right? 890 - > Yes. 891 - > So it was just like, hey, look, this this this accountant signed 892 - > up.

893 - > How do we feel? 894 - > Okay, let's go through the data, let's go through the credit. 895 - > This feels good. 896 - > Okay, yes, we're good.

897 - > Everybody's good. 898 - > This is not as scary. 899 - > Let's approve it. 900 - > Next one.

901 - > And we start we start just kind of like building that muscle. 902 - > SPEAKER_02: Little momentum, little muscle, little feeling of 903 - > here, we got this. 904 - > One just stacking one after another. 905 - > You're you're in Hellsom 2.

0, the pandemic hits, you're almost 906 - > out of capital. 907 - > What is what does the first early customers look like? 908 - > Do you start gathering some momentum? 909 - > Do you how quickly do you recover some of that gap in 910 - > burn?

911 - > Like, what do you have to make in that first year to not freak 912 - > out from a cash perspective? 913 - > SPEAKER_05: So we uh we were lucky that like the signups 914 - > started coming in pretty quickly. 915 - > Okay, good. 916 - > SPEAKER_02: Um and that's because if some exist like a 917 - > little bit of brand reputation, a little network.

918 - > SPEAKER_05: Because we really essentially it's a new company. 919 - > Do we rename it? 920 - > Do we go, or do we go, do we leverage some of the five stars 921 - > and the reputation we had built already and just clarify the 922 - > market like this is a new service? 923 - > And we decided the latter, and I think that served us well 924 - > because there was already there's already a group of 925 - > customers that that like knew about us and you know.

926 - > You leveraged the brand. 927 - > We were the good guys in the not so great industry, right? 928 - > SPEAKER_02: Um, and now we made it easier to sign up and and the 929 - > fact that you could still use the brand, because I guess you 930 - > sold when you sold, you sold the parts, you didn't really exactly 931 - > we sold the customer base, but we didn't sell the honestly. 932 - > That's that's huge.

933 - > I think that's a that's a huge advantage that you had in those 934 - > early days, right? 935 - > That you had an existing base of people who knew and recognized 936 - > the brand that you could take to that next that next level. 937 - > SPEAKER_05: And that's what we did. 938 - > And like so then the business started growing quickly.

939 - > We realized that there's a lot of stuff that we needed to fix. 940 - > So we had we had bidden off a lot and we had to chew through 941 - > it all, right? 942 - > So, you know, our mission um is to be to be the world's most 943 - > loved payments company, and our customers were like, We love the 944 - > mission, we want you to deliver on it, but it's everything's a 945 - > little bit on fire, kind of thing, right? 946 - > We want you to be lovable, but uh your product needs to work.

947 - > But customers were amazing in giving us the patience through 948 - > it because I think they knew that our heart was in the right 949 - > place, and like we were honest about the pricing and the way we 950 - > delivered the service and like how we built it. 951 - > SPEAKER_02: You know, even as I think about how you did the the 952 - > pricing, like we're talking about transparency and honest, 953 - > but also one of the themes that we we see for the Davids versus 954 - > Goliaths is like the Davids choose hard.

955 - > SPEAKER_05: Yeah. 956 - > SPEAKER_02: The David the Davids choose, we say like when Goliath 957 - > is chasing after you, you run up the stairs, not down. 958 - > A hundred percent. 959 - > Because Goliath can't run up the stairs.

960 - > SPEAKER_05: And and I think that if anything, anything that is 961 - > worth doing should be hard, because then the this you know 962 - > the the reward on the yes side would be better. 963 - > So one of we have four core values, and one of those is we 964 - > choose the harder path. 965 - > Um again, and it's like we always ask ourselves, are we 966 - > taking the easy decision or are we taking the hard decision? 967 - > Because odds are the hard decision will have a better 968 - > payoff and a and a stronger foundation.

969 - > And we are always trying to train ourselves and our team, 970 - > like I do the harder decision. 971 - > That doesn't always line up because like it's sometimes it's 972 - > it's you're so tempted to cut corners. 973 - > SPEAKER_02: Yes, yes, or like this this shorter decision will 974 - > get me to the next one. 975 - > Like you kind of convince yourself it's the right short 976 - > term.

977 - > SPEAKER_05: And you you have to you know, there's still a part 978 - > of it where you have to balance it because you know, as a 979 - > startup, you know, if you have just six months to live or 980 - > whatever it is, is like especially in the early days, 981 - > right? 982 - > Yeah, like sometimes you're like, okay, I'm gonna have to 983 - > figure out but I but I think the decision applies especially to 984 - > like decisions that impact our brand and how we're perceived in 985 - > the market and like our core values, that is 986 - > non-questionable.

987 - > Like you got to you you just you gotta take the harder path. 988 - > Yeah. 989 - > SPEAKER_02: You mentioned you mentioned the the the focus of 990 - > your customers. 991 - > I think it's really interesting because you sort of called them 992 - > before you've got the forgotten middle.

993 - > Sort of this, this, this. 994 - > And I think this is interesting because again, I see it in the 995 - > other David versus Goliath stories. 996 - > So one of the stories that we like to tell is is Jesse Cole's 997 - > Savannah Bananas sort of you know, craze that's happening. 998 - > They're obviously not a software or tech, but it's like this 999 - > little collegiate baseball team out of Savannah, Georgia manages 1000 - > to essentially sell out more than some MLB teams, right?

1001 - > And how do they how do they do that? 1002 - > And Jesse talks about a little bit of the forgotten middle. 1003 - > He goes, most people think you're supposed to build the 1004 - > best baseball team, but that's only the people who the diehard 1005 - > baseball fans who want better baseball. 1006 - > Well, if they want better baseball, they're not coming to 1007 - > the collegiate baseball league.

1008 - > They get right like you want better players and better 1009 - > baseball. 1010 - > It was like, no, actually, it's the families and the kids who 1011 - > are just coming for entertainment. 1012 - > Yeah. 1013 - > And if I served them fun, I can get more people to show up.

1014 - > And so it was this, you know, like sometimes, I mean, it's 1015 - > it's the innovator's dilemma, right? 1016 - > It's it's Clay Christians who says when you chase the best 1017 - > customers constantly, they want bigger and bigger mainframes. 1018 - > So IBM builds bigger and bigger mainframes, and then Apple goes 1019 - > and makes a shittier computer for a smaller market. 1020 - > Yeah.

1021 - > Right. 1022 - > And so you sort of go, we're gonna make transparent but 1023 - > complex pricing for this forgotten middle. 1024 - > SPEAKER_05: I think what's interesting is that you have all 1025 - > these startups that talk about small business, but I don't 1026 - > think I think a lot of times um they haven't spent enough time 1027 - > with what small business is. 1028 - > SPEAKER_01: It starts a small business until like you get big 1029 - > business.

1030 - > That's what it is. 1031 - > You know, it's like wait, small business and then move up 1032 - > market. 1033 - > SPEAKER_05: Or if you think about like what's a small 1034 - > business. 1035 - > So like we get that with when we're educating like investors 1036 - > and about our market and everything like that, we're 1037 - > like, what is small business to you?

1038 - > Yeah. 1039 - > And people say, oh, like the the the the corner store or the the 1040 - > little restaurant or whatever, and it's kind of like, and it's 1041 - > like, what is big business to you? 1042 - > And it's like, well, you know, McDonald's and Fortune 500, 1043 - > whatever. 1044 - > And it's like there is a giant, giant, giant, enormous world in 1045 - > between that nobody seems to like pay attention to, where 1046 - > it's like um the best, you know, I like to say the law firms, the 1047 - > consulting firms, the dentists, or or the like the wholesalers 1048 - > in that industrial part of town that are selling like aviation 1049 - > parts and plumbing.

1050 - > Yeah, we might think about the plumber. 1051 - > That plumber is going to another business and buying their parts 1052 - > from, and that there's a whole supply chain. 1053 - > And there's like this giant, like when you're flying over, 1054 - > you know, like fly over city, it's kind of like you can think 1055 - > about like, you know, the restaurant and the retail shops 1056 - > or at you know at the mall or whatever's the case, right? 1057 - > But it's like, you know, a third of that town is just industrial, 1058 - > and it's just like super interesting.

1059 - > I think they're super interesting. 1060 - > Um, you know, like call them like you know, we like to say 1061 - > like we love unsexy businesses because they're the best, like a 1062 - > Thailand stone distributor, an aviation parts, like specialty 1063 - > manufacturer, like a medical supply wholesaler. 1064 - > Like those are like those are great businesses and they can 1065 - > make like, but they're still in the world of the banks and the 1066 - > world of whatever, they're still small business.

1067 - > Yes, but they're not a coffee shop. 1068 - > SPEAKER_02: No. 1069 - > SPEAKER_05: And and I think that's what people like that. 1070 - > I think that was our insight.

1071 - > Was that I think in the world of even with like Silicon Valley 1072 - > investors and everything like that, it's like it's either 1073 - > like, well, you're making you're either making widgets for coffee 1074 - > shops or you're making widgets for McDonald's, and there's 1075 - > nothing in between. 1076 - > It's like you are so wrong. 1077 - > Yeah, yeah. 1078 - > Um, but but and we're like, okay, fine.

1079 - > They're the the forgotten middle, it's a pretty giant 1080 - > middle. 1081 - > Um, then that's where we're gonna go. 1082 - > SPEAKER_02: Now, there's no startup story without a lot of 1083 - > pain, a lot of suffering. 1084 - > You get you you get you get you get some momentum, you start to 1085 - > get some customers, but this period of 2000 2020, you know, 1086 - > 2021, um and then in between between where you are then and 1087 - > today, what are some of the most kind of painful and difficult 1088 - > parts of trying to build this business of tackling on the 1089 - > Goliath?

1090 - > Because now you officially are playing in their space. 1091 - > Yeah, you're no longer a reseller, you have enough of a 1092 - > product that you're making a dent, you've got a brand, and 1093 - > you're going to this forgotten middle. 1094 - > They've been collecting payments. 1095 - > Yeah.

1096 - > So I can just switch over. 1097 - > You're not gonna just be like, okay, here's our service. 1098 - > Like, take I'm already with the service, I'm already here. 1099 - > Like, I don't know, I'm gonna switch it over.

1100 - > Switching costs with this kind of stuff feels annoying, right? 1101 - > Like, what are the difficult moments of getting these 1102 - > customers, the difficult moments of product, the difficult 1103 - > moments in your leadership with your team? 1104 - > Like, you are now at the like, you're no longer the fun stage 1105 - > of building something new and exciting. 1106 - > You have some customers, but your product's not good enough, 1107 - > your team is likely not good enough, and you don't have 1108 - > enough capital, and your brand's not good enough.

1109 - > Nothing's good enough. 1110 - > SPEAKER_05: You just bring back all the pain. 1111 - > Yeah, exactly. 1112 - > SPEAKER_02: Yeah, what what what give me some of those moments?

1113 - > What's what's happening? 1114 - > SPEAKER_05: Yeah, so um a couple things. 1115 - > So we we see a lot of growth at first, which is which is great, 1116 - > like initial growth, which is wonderful. 1117 - > Um, but everything feels on fire.

1118 - > Yeah. 1119 - > So um I say the first two years, everything was just like 1120 - > finishing, chewing through everything we had bitten off. 1121 - > So, like you want to get into all these like new features and 1122 - > new products, and you're like, we cannot. 1123 - > Yeah, like we just have to like ultimately like deliver on what 1124 - > we're doing.

1125 - > Um, my my CFO Marge, who's wonderful, comes into my office 1126 - > in late 21 and says, This business is growing quite a lot, 1127 - > which is good. 1128 - > We need to find investors like yesterday. 1129 - > And I didn't know what a VC was. 1130 - > It was that investors.

1131 - > And then on top of that, um, we start we launched with like this 1132 - > little hardware. 1133 - > It was like a little calculator, like a little card reader for 1134 - > the chip and pin and everything. 1135 - > And um, this is kind of back to the original of like when we 1136 - > moved away from the shadow to bank, we didn't have as much as 1137 - > data because they had like much more equipment and offerings 1138 - > that we did. 1139 - > So we had kind of we went back to just like this is the only 1140 - > thing square reader.

1141 - > Exactly. 1142 - > That's the only thing we could bring to the market. 1143 - > And the customers are telling us we love the payments, but the 1144 - > hardware it's kind of not what. 1145 - > What like I need, right?

1146 - > I need like a real smart terminal. 1147 - > I need this, I need that, whatever, right? 1148 - > So we are um we had found this manufacturer in Hong Kong that 1149 - > that was helping us build these things, and we were working with 1150 - > them to uh launch a new unit that was more robust and 1151 - > everything like that. 1152 - > And um they I'll get into the story, but essentially, like 1153 - > they uh they ghost us, we don't know what's happening, we're 1154 - > about to run a big manufacturing run.

1155 - > It turns out that Stripe bought them because Stripe was also 1156 - > using them to build their hardware. 1157 - > And uh day one, they tell us, yeah, you you can't use this 1158 - > manufacturer anymore. 1159 - > SPEAKER_02: Talk about Goliath Goliath showing up and saying, 1160 - > I'm gonna buy the supply chain. 1161 - > SPEAKER_05: Yeah, literally.

1162 - > Yeah. 1163 - > And there's not many of these manufacturers in the world. 1164 - > You can't compete with us. 1165 - > SPEAKER_02: That's that's some good defense.

1166 - > Okay. 1167 - > So we uh did you lose did you guys lose you guys lost some 1168 - > money on? 1169 - > I mean, you lost time and resources on that, but the 1170 - > contract, or guess, I guess I don't know. 1171 - > SPEAKER_05: It's more um bring a piece of hardware, like this 1172 - > gets to regulation and compliance and security.

1173 - > It you can bring a piece of hardware to market can take 1174 - > about two years, and so it's a whole lot of like investment and 1175 - > stuff like that, right? 1176 - > So we've got an inventory, enough inventory to carry us for 1177 - > a little bit, but now and um through um I'm jumping ahead a 1178 - > little bit, but like we had just raised capital for the first 1179 - > time. 1180 - > SPEAKER_02: Yeah, in 2020. 1181 - > SPEAKER_05: This is 2022.

1182 - > Okay, right. 1183 - > So we raised our series A, we brought in great investment 1184 - > partners. 1185 - > They saw it's funny because when we were talking, when we were 1186 - > pitching investors, we thought we're like, hey, like we're 1187 - > growing really well, massive market. 1188 - > Um, you know, we we have the bootstrapping experience, like 1189 - > we're just gonna be easy.

1190 - > First of all, fundraising is never easy, or at least for 1191 - > most, uh, it's not. 1192 - > And um, and it's funny because the the most pushback we got 1193 - > from investors, like, oh, there's already like there's 1194 - > square and stripe, no, in the market, like Shopify. 1195 - > Like, you're not, you know, why bother? 1196 - > SPEAKER_02: It was literally like there literally, there are 1197 - > there are new age Goliaths and there's old age Goliath.

1198 - > Yeah, there's the banking of the mirror, and there's these huge 1199 - > guys in tech. 1200 - > What are you doing? 1201 - > Yeah, and who are you? 1202 - > SPEAKER_05: And it took and and it took um some courageous 1203 - > investors that that saw what we're doing, um, and said, you 1204 - > know what?

1205 - > Yeah, these guys are definitely choosing the harder path. 1206 - > And you know, they they they still have told us like, you 1207 - > know, you guys chose a really hard business to get into, but 1208 - > if it works out, we're gonna see something really big, right? 1209 - > And you so you have to find investors that match those 1210 - > values that like believed in the harder path, right? 1211 - > So yeah, we we have we have new investors.

1212 - > We're we we just lost our manufacturer. 1213 - > Um, everything still feels on fire, starting to get better, 1214 - > but there's growth. 1215 - > So it's like as long as there's growth, you can make it work in 1216 - > a startup world. 1217 - > SPEAKER_02: You lost your manufacturer, you got some 1218 - > investment.

1219 - > What do you do when you lose your manufacturer? 1220 - > You just start shopping around. 1221 - > SPEAKER_05: You you start flying around the world. 1222 - > SPEAKER_02: You just start flying around the world.

1223 - > Yeah, and like you've never done manufacturing. 1224 - > So are you just like I'm flying into Hong Kong? 1225 - > SPEAKER_05: Like, I'm yeah, like what you're trying to find, you 1226 - > know, spending time in Taiwan, spending time in other places, 1227 - > going like who can do this for us? 1228 - > And you're yeah, you're just pulling on all the connections 1229 - > that you've made in the payments world, going like, hey, who who 1230 - > manufactures uh PayPal's hardware?

1231 - > Yeah, who's manufacturing squares? 1232 - > Who what about clover? 1233 - > What about toast? 1234 - > Like who's behind who kind of thing?

1235 - > Yeah. 1236 - > And you're trying to get introduced, you're trying to get 1237 - > there. 1238 - > SPEAKER_02: And you're trying to find the two or three factories 1239 - > that make everyone else's things, like because we found 1240 - > it. 1241 - > SPEAKER_05: Yes.

1242 - > And we found a great partner in the end. 1243 - > And we learned some lessons too, which is um, you know, when it 1244 - > comes to manufacturing, I mean, realistically, you're never like 1245 - > if electronics, you're not gonna manufacture it in North America. 1246 - > You have to find a partner in Asia that's gonna manufacture 1247 - > like there's no one manufacturing. 1248 - > Yeah, exactly.

1249 - > Um, but there's some key lessons there, which is um, from a 1250 - > contractual basis, make sure that like you have better 1251 - > structure in place so that if you know they have an exit or 1252 - > whatever kind of thing, like you have some, some, some, some 1253 - > protection there, right? 1254 - > Um, and then but more importantly, build a great 1255 - > relationship. 1256 - > And that's something that we've invested heavily with with our 1257 - > new partners.

1258 - > Um, they are uh invested in our business, like okay. 1259 - > So like we've learned that lesson. 1260 - > SPEAKER_02: That's a really interesting theme. 1261 - > I'm sort of finding in a lot of these David Risk Life stories 1262 - > also.

1263 - > It's like your key institutional partners, you almost you want to 1264 - > increase their skin in the game. 1265 - > SPEAKER_05: Yeah, 100%. 1266 - > Yeah. 1267 - > Because you want them to, like, you need you you you need 1268 - > somebody that can you know support you in pack a punch if 1269 - > you're gonna be able to do that.

1270 - > SPEAKER_02: It's like you're I I also need you to know that my 1271 - > success is your success. 1272 - > Like I need you to here, you know, take a p take a piece of 1273 - > this, right? 1274 - > Like and and help us. 1275 - > And that's sort of this, this like David building his army.

1276 - > Yeah, this is like, okay, right, I'm gonna collect a few uh, you 1277 - > know, lieutenants, I'm gonna collect a few people in order to 1278 - > be able to like effectively take on this battle. 1279 - > SPEAKER_05: And it's thinking about like when you say building 1280 - > that army, it's also thinking about like who, yeah, when 1281 - > there's giant, giant competitors or giant, giant Goliaths in the 1282 - > world that are like dominating the market, who is not getting 1283 - > to participate?

1284 - > SPEAKER_02: Who are they blind to? 1285 - > SPEAKER_05: Yeah, yeah, and and and who is not um who is not 1286 - > part of that, you know, is is being excluded from that 1287 - > success. 1288 - > SPEAKER_02: Okay, okay, that's indifferent. 1289 - > SPEAKER_05: Yeah, who's who is being so who is being excluded 1290 - > from the So there's a couple ones.

1291 - > So um obviously from our like most importantly from our 1292 - > customers, right? 1293 - > Like we felt like we were targeting a portion of market 1294 - > that was not being served well and um was being neglected, 1295 - > right? 1296 - > So it's like you know, they have a skin in the game. 1297 - > And we've actually gotten every time we've done a round of 1298 - > financing, um, we've actually gotten some some customers, some 1299 - > key customers in there to invest into our business.

1300 - > And like just not not a on a on a on a big scale, but like we 1301 - > love having like a key customer come into a round with us and be 1302 - > part of that story. 1303 - > Um, you have so even on the bank side, because you still as a 1304 - > fintech, as a financial you know, technology company, you 1305 - > still need bank partners, right? 1306 - > So it's it's yeah, if you have like Stripe or Square or others, 1307 - > right? 1308 - > Some of they have their own bank partners and they're happy to be 1309 - > there.

1310 - > Well, who's missing out? 1311 - > And maybe they want to be your friend, right? 1312 - > And that's how we've we've continued to kind of partner in 1313 - > that way, right? 1314 - > And same thing on the manufacturing task.

1315 - > It's like you can you can rally a coalition of people that would 1316 - > also be part of that next wave of success that are being 1317 - > excluded from the missed out from the first round or the 1318 - > second round. 1319 - > SPEAKER_02: It's also a good invest a way of fundraising. 1320 - > Yeah. 1321 - > Who felt like they missed out, right?

1322 - > SPEAKER_05: Like who's who's well, we we part of our so we 1323 - > did a series B in 2024. 1324 - > Um, and uh so we we we we 5x'd our business from the A to the 1325 - > B, and that was great. 1326 - > And um part of our pitch was um if you look at if you go to to 1327 - > NerdWallet or Forbes or whatever, and you look for top 1328 - > payment companies, right? 1329 - > We're usually in a top three, and we we would tell investors 1330 - > like two out of those three of those companies are worth$50 1331 - > billion, and one of those is raising a series B.

1332 - > SPEAKER_02: So like So do you want a discount at what the 1333 - > future is exactly, right? 1334 - > SPEAKER_05: Like, do you want to come in because you kind of 1335 - > missed out on the other ones, but we're making this happen 1336 - > again, right? 1337 - > SPEAKER_02: Yeah, I'm I'll write you my check later. 1338 - > Um so so you okay, so you mentioned this.

1339 - > So there's obviously these low moments of like difficulty of 1340 - > manufacturing, difficulty of just like keeping up with the 1341 - > product, the products on fire. 1342 - > There's so much everything's on fire. 1343 - > But then, you know, you raise your you raise your series A, 1344 - > and between your A and your B, 5x growth. 1345 - > So clearly there's there's some momentum and you're really 1346 - > building on this.

1347 - > Talk to me about what's working. 1348 - > What are some of the pieces that you're like, team is starting to 1349 - > work, strategies moving, brand is moving. 1350 - > What are the pieces that are clicking that you start to 1351 - > double down on? 1352 - > It's no longer just putting out fires, but here are leverages 1353 - > that we now start taking advantages of.

1354 - > SPEAKER_05: I think that we I think we knew from the start, I 1355 - > think that insight paid off in terms of like uh the our 1356 - > perspective on the market and who was being underserved and 1357 - > that they needed something else. 1358 - > I think we have so that's one thing. 1359 - > Um I do I do think that all of the success is always a mixture 1360 - > of like strategy, serendipity, serendipity. 1361 - > SPEAKER_02: Well, okay, so so I mean, yeah, that's what we say.

1362 - > It's like right, do you do you ride the wave when it comes or 1363 - > do you fight the wave? 1364 - > SPEAKER_03: Right. 1365 - > SPEAKER_02: Like is your surfboard ready? 1366 - > And like we say, the the Goliaths are sort of sitting and 1367 - > standing on top of the water, and the water is crashing into 1368 - > them while the rest of us are on surfboards that we've either 1369 - > learned to surf or we're drowning.

1370 - > Exactly. 1371 - > So so you're you're you're paddling because you're on the 1372 - > surfboard, you haven't learned to surf for those first few 1373 - > years, you're paddling, but but then you start to learn to surf. 1374 - > Like that, so what is what is that serendipity as this tidal 1375 - > wave of shift in payments? 1376 - > Because there is a there is a wave of shift in the payments 1377 - > industry that you didn't have anything to do with.

1378 - > It's just the reality of the shift in technology. 1379 - > SPEAKER_05: And are we a part of that right wave, which we we 1380 - > which I think we got lucky that we are, because you know, those 1381 - > legacy providers like the Menerases of the world, like the 1382 - > TDE of the world, um, are really starting to kind of spin their 1383 - > wheels and um not keep up from an innovation standpoint. 1384 - > Yeah. 1385 - > And I think customers are starting to really realize it's 1386 - > like when you're thinking about maybe you were with the bank, 1387 - > you know, three years ago, five years ago when you signed up for 1388 - > your bank account and they gave you a machine, whatever, right?

1389 - > But if you're thinking about changing that, you're no longer 1390 - > considering, even considering them as part of the the mix, 1391 - > right? 1392 - > No. 1393 - > So now you're comparing Hellsom with the few kind of new modern 1394 - > ones in the market and seeing who's who's better fit for you. 1395 - > So I think we've been lucky to be able to like obviously it 1396 - > took a lot of work and a lot of risk, but you know, to be on the 1397 - > right side of that, that what's happening in in the market.

1398 - > Um, I think that we are the other thing that's changing in 1399 - > terms of like our business is like we start bringing in uh in 1400 - > the past few years, like some more experienced people. 1401 - > So I think we were we were really dogged about this like 1402 - > bottom up, everybody's gotta be a junior, everybody's gotta be 1403 - > green. 1404 - > And like that came from the right place. 1405 - > I think that came from that like that that defiance, and like we 1406 - > can we can build it right here.

1407 - > We want to be the rebels. 1408 - > We want to be the rebels. 1409 - > We want to be the rebels. 1410 - > SPEAKER_02: We're gonna arm the rebels with the financial tools, 1411 - > you know.

1412 - > SPEAKER_05: But I think that's like me learning as a leader, 1413 - > going, like, yeah, you know what? 1414 - > You don't need to relearn every lesson from scratch. 1415 - > Like, you know, like what if we still have that attitude, but 1416 - > then we also can bring in some people that says, like, hey, 1417 - > like, don't waste your time for six months like learning this 1418 - > lesson. 1419 - > I'm just gonna tell you this lesson.

1420 - > Why don't we go try this instead, right? 1421 - > Um, so we start bringing in some more, uh, especially at like the 1422 - > leadership level, right? 1423 - > Like, I love the mixture of we try to have this three to one 1424 - > ratio at the office, which is um three juniors for every senior. 1425 - > So it's kind of like you have these like really wonderfully 1426 - > driven young people that like want a shot, yeah, but then you 1427 - > have somebody that like been there, done that, that can like 1428 - > be like, hey, don't step on this landmine.

1429 - > Why don't we just walk around this one and like kind of help 1430 - > us accelerate? 1431 - > Um, it took us a while to like really learn that lesson, but in 1432 - > the past few years, we've really kind of started bringing that 1433 - > ratio. 1434 - > SPEAKER_02: I mean, you think about the best sports teams, 1435 - > right? 1436 - > You've got these energetic, brilliant young athletes who 1437 - > need a coach.

1438 - > Yeah, who's just a bit older, a bit of done that, okay, let's do 1439 - > this, let's just focus the team. 1440 - > Come on, guys, right? 1441 - > SPEAKER_05: Like, say, hockey or whatever it's like, the captain 1442 - > is usually a little bit more like you know, a little bit 1443 - > more, more maybe not grays, but a little more experienced. 1444 - > That is like who is setting the tone and helping the team focus, 1445 - > right?

1446 - > SPEAKER_02: So now I love this point selfishly, because we got 1447 - > to work with you guys on leadership development. 1448 - > We got to work with your leaders, we got to help, you 1449 - > know, help them level up, help coach them, help put them 1450 - > through a program, you know, a lot of learning and development 1451 - > there. 1452 - > But I gotta say, like even when we first engaged, I and I think 1453 - > I said this to you, was like, I was really impressed with the 1454 - > intention around culture, the intention around values, the 1455 - > intention around we want to use culture as a differentiator in 1456 - > the in the team that we attract.

1457 - > We want we want to invest in our juniors to help them grow 1458 - > because you were investing in leadership development, you're 1459 - > investing in skill development. 1460 - > And so talk to me about that. 1461 - > Talk to me about this. 1462 - > Where does this um where does this philosophy come from?

1463 - > What is the philosophy around culture that you've held? 1464 - > And where have you seen it pay off? 1465 - > And where have you seen some of it fall short and and and and 1466 - > some difficult moments as you corrected that culture? 1467 - > Because I think the analogy we use for culture is like culture 1468 - > should be like black licorice.

1469 - > Some people love it and some people hate it, right? 1470 - > Like it's it's not for everyone as you start to define what it 1471 - > is. 1472 - > SPEAKER_05: 100%. 1473 - > I I like to compare culture with like uh flavors of ice cream, 1474 - > and like every company is a flavor, and that doesn't mean 1475 - > it's your favorite flavor, but like for the people that love, 1476 - > you know, I don't know, mango peach or whatever, like they're 1477 - > gonna click with you.

1478 - > And what we try to do, and that was our mindset from from early 1479 - > on was let's just make so we made our culture book public. 1480 - > And we we did that four and a bit years ago. 1481 - > So kind of like around the time we relaunched our business. 1482 - > So it's hellsome.

com slash the way. 1483 - > So it's the way of the hellsome. 1484 - > And um the way of the hellsome. 1485 - > SPEAKER_02: That's uh that's what we got here.

1486 - > That's what we got here. 1487 - > We got another show. 1488 - > SPEAKER_05: Zoom in on that. 1489 - > So the the the idea though was really around like we knew 1490 - > pretty early on who we wanted to be and who we didn't want to be.

1491 - > Part of it is because we're trying to be, you know, like I 1492 - > said, the good guys in the not so great industry, like we knew 1493 - > that values and how we made decisions needed to be set like 1494 - > really early on because we were an industry where you could lose 1495 - > that very quickly. 1496 - > And um, the other part why we we did that was around, and I say 1497 - > we, it's like our our our leadership team was around um 1498 - > because we were so junior focused, you had all the entire 1499 - > team was just these like green first job professionals.

1500 - > And we felt like we just had to like give them a guide on how to 1501 - > like operate and like how to like better make decisions. 1502 - > So that kind of forced us to like you know, if we had hired 1503 - > all these super experienced people, I don't know if we would 1504 - > have like this need to like set culture, then it kind of bites 1505 - > you on the other side because you didn't think about it 1506 - > enough. 1507 - > But for us, it came from like you know, we need to give them a 1508 - > handbook, like they're so green, right?

1509 - > Um, that was wonderful because it it kind of really might if we 1510 - > we force ourselves to go through this exercise for a long period 1511 - > of time of like who we are, what do we actually care about? 1512 - > And um, while the culture book has had a couple different 1513 - > iterations, it's actually still pretty um similar to the to the 1514 - > original. 1515 - > Yeah. 1516 - > Um, when we uh after we did our series A, which is in 2022, 1517 - > after you know, you have to you only celebrate like two days 1518 - > after the check cleared, and like you just like um in the 1519 - > bank again.

1520 - > When everything is like solidified and it's real, I 1521 - > actually went to one of our uh our co-leading investors in the 1522 - > series A, who's a longtime uh Rob at Information Venture 1523 - > Partners, IVP in Toronto, who's like an old school VC that's 1524 - > been around the block a a few times and like really knows the 1525 - > space well. 1526 - > And I asked him straight up, why did you invest? 1527 - > Now that the check is clear, now that we're gonna feed back, why 1528 - > did you invest?

1529 - > Right. 1530 - > And like outside of like, you know, the the the market 1531 - > potential and the company, like you know, and um he shared that 1532 - > we were uh really intentful. 1533 - > He saw that we were really intentful um in our culture, and 1534 - > in his experience as a venture capitalist, is companies that 1535 - > are very intentful with their culture have has given them 1536 - > alpha and like disproportionate returns, right? 1537 - > Um, where it's like companies that like they're not just 1538 - > trying to follow like the typical kind of cookbook, 1539 - > they're actually trying to like really be meaningful in like how 1540 - > they want to operate as a company and what makes them 1541 - > unique and everything like that.

1542 - > And I think that just made us kind of double down on like, oh, 1543 - > this actually matters, and it matters to a certain type of 1544 - > investors. 1545 - > And that was, I think, really reaffirming that like we're on 1546 - > the right path. 1547 - > SPEAKER_02: Yeah, I like that. 1548 - > I mean, it it impacted the investors' decision.

1549 - > You you gave your team a set of values that become 1550 - > decision-making parameters. 1551 - > Yeah, and then through this sort of culture building, you built 1552 - > this culture of leadership where this this responsibility for all 1553 - > people to take on the culture. 1554 - > This this sort of leadership is not um a position and you don't 1555 - > wait for permission that everyone owns a part of it. 1556 - > And I think what what I saw in your culture and in your team is 1557 - > is this real sense of empowerment, of giving people 1558 - > the the ability, the ownership of owning their teams, of owning 1559 - > their decisions, of owning a big a part uh quite a bit of that.

1560 - > Talk to me about that. 1561 - > How how what's the what's but like what's the transformation 1562 - > for you as a founder to be able to create this culture that 1563 - > allows for fluidity and leadership, where it's not 1564 - > always just you know, my way or the highway, but there are 1565 - > leaders that are being developed across the organization to to 1566 - > run with things. 1567 - > SPEAKER_05: Yeah, I think if you look at if you're uh I mean you 1568 - > have because you you went through the training with us.

1569 - > When you sit down with our our leadership team and my like my 1570 - > executive team, they're actually really different personalities, 1571 - > like really different personalities. 1572 - > Um and the fact that we're able to like have that, but then 1573 - > still be very value aligned, um, I think is a testament to like 1574 - > just being really straightforward about who we 1575 - > are, who we're not, and where um like our other and and where is 1576 - > there a lot of give, right?

1577 - > So like our our fourth core value. 1578 - > So I'll give you the four core values, right? 1579 - > We are builders, and that's really about that like that that 1580 - > that building coding, everything, building kind of 1581 - > mindset of like we build things and we build things well, and 1582 - > and we invent our way of problems, that's all part of it, 1583 - > right? 1584 - > Uh we choose the the harder path.

1585 - > Um, and we've talked a lot about that. 1586 - > Uh, we are trustworthy. 1587 - > And you know, there's a line in there that says, like, you know, 1588 - > trust isn't yeah, trust is um uh hard to gain, easy to lose, and 1589 - > continuously tested. 1590 - > SPEAKER_03: Right.

1591 - > SPEAKER_05: And that's with our customers, that's with each 1592 - > other, that's everything, right? 1593 - > And then the fourth c the fourth value is like we are a company 1594 - > of many. 1595 - > And that's like about um being mindful that we even say like 1596 - > the most important thing is to us is is our people and then our 1597 - > customers and then our and not because we don't think our 1598 - > customers are like we we live and breathe our mission to be 1599 - > the world's most loved uh payments company, but if you 1600 - > don't treat your people and with the way that you you that you 1601 - > should, they won't take care of your customer.

1602 - > And that's the problem with some of these companies that are 1603 - > like, you know, cus they say they're customer obsessed, and 1604 - > like say Amazon or whatever, right? 1605 - > But if they treat their people like shit, then it's gonna 1606 - > cascade down to the customer. 1607 - > Yeah. 1608 - > Like you see it in customer service, so you see everywhere, 1609 - > right?

1610 - > So you really have to like so the fourth, the fourth core 1611 - > value is we are we are a company of many, and that's really about 1612 - > like acknowledging the fact that's not just about there's a 1613 - > there's a diversity component to that, but there's also like a a 1614 - > a company is just a bunch of people, you know, taking away 1615 - > the titles and the the the walls and everything like that. 1616 - > We're just a bunch of people on a couple floors of a downtown 1617 - > building to try to build something really exciting 1618 - > together.

1619 - > And we have to acknowledge that like it takes a whole lot of 1620 - > humans to like working together and to make that happen. 1621 - > SPEAKER_02: What are some of the best or uh ones that you reflect 1622 - > on? 1623 - > The best sort of cultural people decisions that you've made. 1624 - > And not people decisions in terms of like key hires, but 1625 - > about the culture.

1626 - > So like you made a decision to codify the culture, yeah. 1627 - > That had its its implication and and it helped uh you know civic 1628 - > significantly the team. 1629 - > You say one of the codifications of that culture is you know, 1630 - > really we are a company of many of this idea of taking care of 1631 - > the people. 1632 - > What did some of those stri those decisions look like?

1633 - > What would what did you have to invest in? 1634 - > What did what was some of the trade-offs that you had to that 1635 - > you had to make in order for that value to come to life? 1636 - > SPEAKER_05: There's so obviously publishing a culture book early, 1637 - > which was really like nerve-wracking. 1638 - > We did it originally, was one of the best decisions that we made 1639 - > because it um people to filter out amazingly, and and that 1640 - > people like it's so common that people sit down and interview 1641 - > with us.

1642 - > Like, I read the culture book, I read the Well Hellsome, oh my 1643 - > god, here's what I clicked with, whatever. 1644 - > And like it, it's just such a wonderful like filtering process 1645 - > and and to get the people excited. 1646 - > I think it also helps us attract really talented, great people 1647 - > because they get a you know, they have one opportunity, they 1648 - > know nothing about what that flavor of ice cream is, and then 1649 - > they see our mango peach and they read in depth about it, and 1650 - > they're like, you know what, I like this flavor and I want to 1651 - > work there.

1652 - > And I think that probably gives us access to like better talent 1653 - > because it's gonna filter, but it's also gonna get people more 1654 - > excited about our opportunity, right? 1655 - > Yeah, um, we do a couple things where um I still meet with 1656 - > everybody, and I I I I hired a company with over 2,000 staff 1657 - > that still does this with their CEO. 1658 - > And I'm like, if that company can do it, I can do it. 1659 - > Where I meet with everybody that's new.

1660 - > So like we've now we now lump it every couple weeks where it's 1661 - > like anybody that's new in the room, and I sit down for an hour 1662 - > and I chat with them, and I kind of go through high-level 1663 - > expectations. 1664 - > And one of the early things I talk about is like it's a little 1665 - > bit of like a no assholes policy, which is pretty common, 1666 - > but I it's common stated, it's not common practice, practice, 1667 - > yeah. 1668 - > Yeah, um, and one of the ways that we explain that is we go, 1669 - > my expectation of you, you're new today.

1670 - > There's gonna be somebody new next to you in a you know a 1671 - > week, a month or whatever, right? 1672 - > Um, and every single person has heard me say this as this 1673 - > company, and now you are hearing me say this, which is my 1674 - > expectation is that we should be able to take any person of any 1675 - > background, any technical background, any experience, it 1676 - > doesn't matter. 1677 - > And we should be able to like drop them into a team, and the 1678 - > gut reaction of that team has to be spin their chair, how can I 1679 - > help you?

1680 - > How can I make you successful? 1681 - > And if you don't experience that, please let me know 1682 - > immediately. 1683 - > And then my expectation of you is that you carry that tradition 1684 - > because there's gonna be a new person next to you soon, and 1685 - > then you better spin your chair and be like, How can I help you? 1686 - > How can I make you successful?

1687 - > And the fact that they hear that from the CEO, you know, day one 1688 - > or week one or month one, whatever, right? 1689 - > I think is like just setting that ground early. 1690 - > My other executives do. 1691 - > Um They go through core values together.

1692 - > We love a book, um, uh Five Dysfunctions as a team. 1693 - > Everybody gets that book day one. 1694 - > And then at month one, um, the executives will sit down and 1695 - > like go through the book, like do a little book club with them, 1696 - > be like, what did you learn? 1697 - > What are the keep takeaways?

1698 - > SPEAKER_02: So I think we're just eventually the David versus 1699 - > Goliath book is gonna be the the next one on their on their list, 1700 - > right? 1701 - > Like I agree. 1702 - > I agree. 1703 - > SPEAKER_05: So um, and then you what the the main thing though 1704 - > is that like we are being purposeful in establishing it 1705 - > almost like obviously what you say matters, but more 1706 - > importantly, you are making a point that this is real, culture 1707 - > matters, our decision making matters, and um we are setting 1708 - > that tone day one.

1709 - > Yeah, and I think we're setting a clear tone that like this 1710 - > isn't just posters on the wall with slogans or whatever. 1711 - > It's like we live and breathe this stuff, and it and and this 1712 - > ethical and and kind of like character, call it character 1713 - > like matters day one. 1714 - > SPEAKER_02: Yeah. 1715 - > The intentionality, how you bring it to life, how you speak 1716 - > about it, how you teach it, how you bring it out.

1717 - > Um has there been a moment where you feel you faltered on it? 1718 - > SPEAKER_05: Yeah, I mean many. 1719 - > Um it's you know, nobody, nobody's nobody's perfect. 1720 - > I think that we had a really we we evolved our culture.

1721 - > Um, and this is the time that you came in and and helped us 1722 - > with our with our leadership and our kind of next level training, 1723 - > is we went through this transition where we realized 1724 - > that like, yes, we want to create a wonderful, happy place 1725 - > and where people feel appreciated and trusted and all 1726 - > that, but we also want to be this really like high 1727 - > performance company. 1728 - > And I think a lot of companies go through this, especially like 1729 - > you know, we raised our Series B, we're we continue to grow, 1730 - > we're now servicing tens of thousands of customers, you 1731 - > know, we're tens of millions in revenue, and all of a sudden, 1732 - > like the stakes are higher.

1733 - > We're we really want to be this big giant success. 1734 - > And like it's kind of like being moved to the next league in 1735 - > sports and going like, oh, we need to set a higher bar. 1736 - > SPEAKER_04: Yeah. 1737 - > SPEAKER_05: And how does that how does that integrate with our 1738 - > culture?

1739 - > And I think we we struggled for a bit, and ultimately we landed 1740 - > on like, let's be honest with ourselves. 1741 - > What do we really, what, what do we want? 1742 - > What do I want when I get up? 1743 - > What kind of company do I want to go?

1744 - > And I want to, and I I landed on, I want a talent-dense 1745 - > company. 1746 - > SPEAKER_04: Yes. 1747 - > SPEAKER_05: And I want a company where performance management 1748 - > matters and where um you you know you hold people to a high 1749 - > standard. 1750 - > And like, I think we're really good at like creating really 1751 - > healthy, like honesty and dialogue and and like a great 1752 - > happy culture, but I don't know if we're creating as much of 1753 - > like a performant culture.

1754 - > And so we went through this cycle and we updated the culture 1755 - > book, and we were really intentful to the team of like, 1756 - > here's what's the same, here's what's changed, here where it's 1757 - > coming from. 1758 - > And um, and that was a difficult period. 1759 - > That took like a year and a half to really go through, and like 1760 - > there's a lot of people that um what we found is that um the 1761 - > promises that we were kind of making as a leadership team in 1762 - > terms of like this is the expectation, because I think 1763 - > unofficially we always set that expectation and that reflected 1764 - > in the people we hired, was not necessarily the same at all 1765 - > levels.

1766 - > And then we had leadership that was making promises that um 1767 - > about oh no, this is more of a lifestyle job, or this is more 1768 - > this, or this is more that. 1769 - > And we saw a lot of conflict with that because they're like, 1770 - > well, that was never our intent, yeah, but now you're creating 1771 - > you've you've created a subculture standards diluted as 1772 - > you went further, and completely kind of like it expectations are 1773 - > dive, you know, being divergent.

1774 - > Yeah, and we had to kind of bring that back and just had to 1775 - > hit a reset in the culture. 1776 - > And I was really that was that was bruising. 1777 - > That's tough. 1778 - > SPEAKER_02: Because when you're yeah, you're resetting a 1779 - > culture.

1780 - > There's people that are gonna be unhappy about it, some people 1781 - > are gonna leave. 1782 - > Some people are gonna um fight it for a while, like there's and 1783 - > it's you know, depending on how your leadership teams, you know, 1784 - > whether they take that mantle and they take that flag and and 1785 - > and run with it, or if they're also reluctant on that, on that 1786 - > culture change. 1787 - > SPEAKER_05: And you also go through this, I mean, you see it 1788 - > in the startup world where um the people that got you from 1789 - > zero to one are not as they are the people are gonna get you 1790 - > from one to two.

1791 - > Yeah. 1792 - > And that's really, really hard because obviously on one side, 1793 - > like there's there's a loyalty and there's a lot of things. 1794 - > Do you want to reward loyalty? 1795 - > Or do you reward loyalty or performance?

1796 - > Exactly, right? 1797 - > And so you you struggle with that because then ultimately um 1798 - > you have to have an honest conversation with everybody, 1799 - > which is like at some point everybody like like we are like 1800 - > this company is gonna keep evolving, and like you have to 1801 - > continue earning your place on the team, right? 1802 - > And it's it's really hard. 1803 - > And I think that we've learned we learnt better ways to like 1804 - > what to have those tough conversations, yeah, and to be 1805 - > more honest about like hey, like um there's a lot of influence 1806 - > for I think in that Netflix culture around like the keeper 1807 - > tests and around those kind of structures, which is just like 1808 - > you can still make people leave with dignity.

1809 - > Um, and that's a hard skill that took you know a while to learn. 1810 - > We're saying like that doesn't take away from everything that 1811 - > you did to get us here. 1812 - > Yeah, and but like now the the team is in a position where it 1813 - > can't grow unless you grow. 1814 - > Yeah.

1815 - > And we have to have an honest conversation about whether or 1816 - > not you can grow. 1817 - > SPEAKER_02: If the team outgrows you and your pace in which 1818 - > you're improving, right? 1819 - > That's that's part of it. 1820 - > It's like hi, you know, I think that employees sometimes 1821 - > struggle with.

1822 - > I would say that one of the things is as a founder, as an 1823 - > entrepreneur, as as the David in the story, you uh you hit your 1824 - > the in your face, you hit your limitations constantly. 1825 - > Yeah, you were constantly like hit by your limitations. 1826 - > And I remember a younger version of me was pretty upset, like a 1827 - > couple things not working out. 1828 - > Like, and and I went to my mentor and I'm like, man, I'm 1829 - > like, I'm trying my best.

1830 - > And he's he looked at me and he's like, Well, your best is 1831 - > not good enough. 1832 - > Yeah, yeah. 1833 - > You're like, ouch, what do you what do you mean? 1834 - > Because you want to feel like your best is good enough.

1835 - > He goes, Your best is not good enough. 1836 - > What made you and it was a tough level? 1837 - > He's like, What makes you think your your current best should be 1838 - > good enough? 1839 - > Just because it's your best.

1840 - > So find another best. 1841 - > Find like what does that next level look like? 1842 - > And I think that's interesting. 1843 - > As an entrepreneur, you're constantly faced with that 1844 - > because you realize that my company is not gonna grow if I 1845 - > don't grow.

1846 - > SPEAKER_00: Yeah. 1847 - > SPEAKER_02: Um, but sometimes when you're in the machine, you 1848 - > don't always come face to face with that. 1849 - > And that's sort of what you're facing was like, how do I 1850 - > increase the skin in the game to an individual employee who might 1851 - > not be seeing the impact of their lack of growth? 1852 - > SPEAKER_05: Yeah.

1853 - > And I think it's funny because as a as a founder, especially as 1854 - > like a venture back founder now, you have you have a pretty 1855 - > constant scoreboard in front of you. 1856 - > Um, where it's just like, are you grading growing at the right 1857 - > rate? 1858 - > Is your business, you know, the all the metrics of your 1859 - > business? 1860 - > Are you able to successfully fundraise?

1861 - > How are you doing compared to your competitors? 1862 - > Like, you know, the the the the investment world and will will 1863 - > let you know pretty quickly when you're gonna be able to do it 1864 - > and it's results. 1865 - > SPEAKER_02: I don't care how hard you're trying, I don't care 1866 - > about effort. 1867 - > Great.

1868 - > Um you're not sleeping, you're not working every weekend. 1869 - > Okay, what are your numbers? 1870 - > SPEAKER_05: And that's all I care about. 1871 - > Exactly.

1872 - > So so then you have to go, okay, how do I how do I merge that 1873 - > with um knowing that a startup is ultimately about like 1874 - > experimentation and failure is is part of that process, but 1875 - > then it's still expecting performance. 1876 - > What does performance mean? 1877 - > Is performance just about delivering on the numbers, or is 1878 - > it about taking risk? 1879 - > Is it a mixture of the two?

1880 - > And it's like, I think that's the really tough part about like 1881 - > uh at C Ona Founders that like you have to you are constantly 1882 - > faced with that immediate scoreboard, yeah, but then you 1883 - > have to like find a way to like set the right expectation, but 1884 - > also give enough room for the magic to happen, that 1885 - > experimentation to happen. 1886 - > So um, not that the the market will give you that, but you have 1887 - > to find a way to give that to your team.

1888 - > SPEAKER_02: Yes, yeah. 1889 - > I think I think you I mean, you know, you you make a great case 1890 - > here for for culture, you make a great case for teamwork, but you 1891 - > also make a great case for your leadership team had to level up. 1892 - > Now, you had to level up as a leader. 1893 - > So what were what was what was what were some leadership like 1894 - > growth moments for Nick?

1895 - > Like that, you know, the the boy Nick that had to the 23-year-old 1896 - > Nick that had to like grow out of, you know, certain habits 1897 - > that he formed earlier. 1898 - > What were some some like hard leadership moments for you in 1899 - > your own growth? 1900 - > SPEAKER_05: I think that I mean there's a few. 1901 - > There, one of them was like learning to let go of the 1902 - > keyboard, even from the coding standpoint.

1903 - > That was definitely a bit of a. 1904 - > SPEAKER_01: Yeah, exactly. 1905 - > Because we're builders, yeah. 1906 - > SPEAKER_05: And you have to learn to like um get that 1907 - > vicariously through the teams that you've empowered to go 1908 - > build as opposed to you trying to build it yourself.

1909 - > That's a lot lesson. 1910 - > I've kind of fumbled a few times on that one because it's so 1911 - > hard, right? 1912 - > Um, the the you know, I've I've brought in some executives 1913 - > lately that like have challenged me straight up going, like, you 1914 - > know, come back to my office after a big leadership meeting 1915 - > and be like, how useful do you think that meeting went? 1916 - > And like when you hear that from your subordinate, you're just 1917 - > like, oh shit, okay, let's talk about this.

1918 - > Yeah. 1919 - > And being open to that, um, you know, I think I've created a uh 1920 - > a culture that like we can we can give each other that pretty 1921 - > raw feedback, which is good. 1922 - > Um, I mean, you hear it all the way time from your investors and 1923 - > your board and things like that, right? 1924 - > Um, it's it's it's a it's a it's a tough gig.

1925 - > Um, but then you have to decide like everybody is replaceable, 1926 - > and do I still want this job? 1927 - > And I'd like I don't, you know, I can be a different role. 1928 - > I can be, you know, innovation person, I could be a developer. 1929 - > It's like if I want to be CEO, then I better, like, this is not 1930 - > um this I'm not entitled to this job regardless if I'm a 1931 - > shareholder or not.

1932 - > Like they are separate. 1933 - > And I better like show that I am learning and growing, or like 1934 - > this job will no longer be mine. 1935 - > SPEAKER_02: I I think that's a I mean it shows the level of 1936 - > humility you have to understand that. 1937 - > Genuinely, because I uh you know, we sometimes in this world 1938 - > mythologize the the Steve Jobs and Elon Musk's and Bay.

1939 - > He lost his job. 1940 - > Right. 1941 - > Steve Jobs got fired for being a bad leader. 1942 - > Musk got a five.

1943 - > And musk fire for being a bad leader. 1944 - > Now, Jobs, I think, learned the lesson because Ad Catmull in his 1945 - > book talk about talks about how in Pixar days, Jobs sort of 1946 - > eases up and learns to have some some people skills. 1947 - > And then, you know, when he comes back to Apple for round 1948 - > two, he does a bit better. 1949 - > Elon Musk, I don't think, learned the the lesson.

1950 - > I think the lesson he learned was retain 51% so they can never 1951 - > remove you. 1952 - > SPEAKER_05: Wrong lesson. 1953 - > SPEAKER_02: Wrong lesson. 1954 - > Uh Bezos gets an executive coach at uh in in I think it was in 1955 - > his it was in his book, but I think in in 2010 kind of period 1956 - > where they start seeing growth, he he realizes he's not people 1957 - > managing, he hasn't grown past certain limitations of his own, 1958 - > right?

1959 - > Like there is this this sort of like the team that got you here 1960 - > won't get you there, but the leader you are that got you here 1961 - > won't get you there either. 1962 - > And and and there's there's a part of that, like, does do you 1963 - > grow into that next phase of leadership? 1964 - > We got to series B, you 5X from Series A to Series B, ride in a 1965 - > pretty good way, got some new team members in. 1966 - > That's 2003.

1967 - > We're today, we're 2005, near the end, getting into 2006. 1968 - > Yeah, yeah, 2005, geez, 2025 going into 26. 1969 - > Um how are things looking? 1970 - > What's what's the future?

1971 - > What where where are where are we in this David versus Goliath 1972 - > battle? 1973 - > Because obviously it's still happening. 1974 - > What's what's what's the current where are you currently? 1975 - > What you know, what numbers are you uh comfortable sharing with 1976 - > us?

1977 - > Like what are some of the milestones? 1978 - > What's some of the growth rate? 1979 - > And what's what's to come? 1980 - > SPEAKER_05: So I say we've tens of thousands of customers, tens 1981 - > of millions in revenue.

1982 - > So we've definitely like reinvented ourselves and are 1983 - > doing pretty well. 1984 - > Um, I think that how about this? 1985 - > What used to keep me up at night, certainly like in the 1986 - > kind of reinvention phase and five years ago, was like, can we 1987 - > survive? 1988 - > Can we, you know, we bid off a lot, can we get to the other 1989 - > side?

1990 - > What keeps me up at night now is can I capture the opportunity 1991 - > that we've created for ourselves? 1992 - > And that's a funner, like it is it is better. 1993 - > Like I have like, don't wrong, I I I live and breathe and think 1994 - > about this nonstop, but it's more fun to think about like to 1995 - > be focused on the upside as opposed to like, will we survive 1996 - > another day? 1997 - > It's really nice to be out of the way.

1998 - > SPEAKER_02: You were you were swinging for first base, yeah. 1999 - > And now you feel like you can swing for some home runs. 2000 - > You can exactly take the bet. 2001 - > SPEAKER_05: So um, I think for us it's really about like when 2002 - > we think about our country expansions, our product 2003 - > expansions, like we have a lot of exciting things coming out, 2004 - > and that's a lot, you know.

2005 - > It's funny because in the moment you're still thinking, well, you 2006 - > know, we're still tiny compared to to Square, and we could be so 2007 - > much bigger, and there's all this bigger stuff coming, and 2008 - > like that's good. 2009 - > That fire keeps you keeps you going. 2010 - > But then you have to catch yourself and be like, yeah, but 2011 - > like first of all, we've grown a fantastic amount in the past 2012 - > couple of years. 2013 - > We continue to grow really well, we've all this fun stuff coming.

2014 - > Like, just enjoy it for a second. 2015 - > Enjoy it. 2016 - > I think that's the main point of of focus right now. 2017 - > Yeah, and I think what's tough is that like you have to have 2018 - > this like endless paranoia in order for you to even get to 2019 - > this point and survive.

2020 - > The only the paranoid survive, right? 2021 - > Exactly, right? 2022 - > So then you get you get a little bit scared of putting down that 2023 - > paranoia because you also got really good at it. 2024 - > Right.

2025 - > SPEAKER_02: It's become your skill. 2026 - > Yeah, I think like one of the challenges that uh the one of 2027 - > the founders' uh typical David's base best skills is the ability 2028 - > to see where they are, see where they want to be, identify the 2029 - > gap and tackle it. 2030 - > But if you're always in the gap, then you're never looking at the 2031 - > reverse gap of like where where'd you come from? 2032 - > Can you be happy for a moment, right?

2033 - > SPEAKER_05: And I'm I'm I'm I'm bad at that as a leader in terms 2034 - > of like the team has to remind me, like, why don't we do a 2035 - > celebration about this milestone? 2036 - > And why don't we do a pizza party? 2037 - > Why don't we do this? 2038 - > What is it?

2039 - > And I'm like, but tomorrow, like it's just like this next 2040 - > challenge, this next hill to climb, right? 2041 - > SPEAKER_02: So yeah, that's a that's a skill that's was there 2042 - > was there a moment moment for you to sit back where you were 2043 - > like, okay, yeah, like I'm I'm no longer in survival mode. 2044 - > Was there was there an was there maybe the big partnership with 2045 - > Verizon? 2046 - > Did that feel like uh did that feel like a moment?

2047 - > Was there a leadership moment? 2048 - > Any any moment where you you know a moment in the beach on 2049 - > vacation where you didn't have to answer everyone's question as 2050 - > CEO? 2051 - > SPEAKER_05: I don't know. 2052 - > I just I I you have moments, but they're so fleeting where it's 2053 - > just like, yeah, you we we announce a big partnership with 2054 - > Verizon, and or you you have this day where you have like 2055 - > everything clicks and and you have great talks and great talks 2056 - > with investors, great talks with your team, great talks with 2057 - > customers, and you're like, oh, we got this, right?

2058 - > And then the next day everything's on fire again, and 2059 - > you're just like that, it's fleeting and you're back at it. 2060 - > So I don't know if there's any um, you know, people talk about 2061 - > like that that that letting go, and I've never experienced an 2062 - > exit. 2063 - > And obviously, we're focused on just building a big, big, 2064 - > fantastic business, and we have got so much more of this 2065 - > business in us, though it's not that's not our focus.

2066 - > But then you have founders that talk about, you know, that like 2067 - > catalyst of like okay. 2068 - > But then you also see like I remember seeing a business 2069 - > hardware review that says, like, uh, you've sold your business, 2070 - > congratulations, get ready for depression. 2071 - > SPEAKER_02: And it's like because the adrenaline of what 2072 - > you've been running on from fire to fire to like goal to goal, 2073 - > you've been fueled by goals, and now there is no gap, there is no 2074 - > goal, which is why you go, okay, so when's this next startup?

2075 - > Like, when's the what's the next game to play? 2076 - > SPEAKER_05: So, what I try to remember is like if I'm when I'm 2077 - > 80 years old and I looking back, like I got to find a way to like 2078 - > enjoy the moment right now, regardless of how many fires, 2079 - > how many what's you know, what's working, what's not, because if 2080 - > not, um you can't just look for that that it it has to be now. 2081 - > Yeah, it has to be. 2082 - > And I look back, it's funny, I look back at the the 20s and the 2083 - > craziness and all that, and I look at it pretty fondly.

2084 - > Yeah, but in the moment it doesn't feel that way. 2085 - > SPEAKER_02: In the moment. 2086 - > So, okay, looking back at some of this story, when we when we 2087 - > were analyzing David versus Goliath stories, we sort of 2088 - > identified that there's there are some things and 2089 - > characteristics and behaviors about the David, the leaders 2090 - > that are interesting and unique and sort of we can learn from. 2091 - > But then there are things that we can learn from the team, kind 2092 - > of how the team works together, what the teamwork looks like.

2093 - > And then there's sort of the strategy that they use, right? 2094 - > What are some of the pieces? 2095 - > And so we've talked about that, like, you know, um uh re they 2096 - > rewrite the rules of the game. 2097 - > David doesn't play the can't David can't fight Goliath in his 2098 - > own battle.

2099 - > He's gonna lose it. 2100 - > They build their own surfboards and learn to ride it. 2101 - > They run up the stairs, they swing for they they have less to 2102 - > lose, so they swing for the fence more often because like uh 2103 - > what am I gonna lose? 2104 - > Just let me do, right?

2105 - > That was you taking on the license. 2106 - > Like it's like less to lose, so I'll just take on a license. 2107 - > I'll try this out, right? 2108 - > So we we've got these, some of these strategies.

2109 - > Those are some of my terms, right? 2110 - > But I'd like you to reflect on these three buckets. 2111 - > What is um, what were some of the key characteristics of your 2112 - > yourself as a founder or other leadership teams that you go, 2113 - > you know what? 2114 - > These are a few characteristics or behaviors that I think are 2115 - > essential for founders to succeed.

2116 - > Some of the teamwork pieces, we obviously focused on culture uh 2117 - > for you, but what are some of the teamwork pieces that really 2118 - > made the difference? 2119 - > And then were there any other strategy pieces that come to 2120 - > mind? 2121 - > Obviously, that we've talked about that that middle, we've 2122 - > talked about the transparency, but those are the kind of three 2123 - > buckets. 2124 - > So I'll get you to reflect on kind of all three here as one of 2125 - > our final big, big questions.

2126 - > SPEAKER_05: All right. 2127 - > So on the maybe on the personal sound, the founder side, like I 2128 - > mean, this is a bit of a cliche, but um like perseverance. 2129 - > I'll take it a step further and say perseverance. 2130 - > I'd say like dogged, maybe a little bit of anti-authority.

2131 - > I will prove you wrong no matter how much logic you throw at me, 2132 - > kind of thing, right? 2133 - > Yeah. 2134 - > Like I think that um rebellious, yeah, rebellious, like slightly 2135 - > stubborn enough to I think for me that came from like there's a 2136 - > counterculture in computers in the 90s. 2137 - > It's about like hacking, and it was about um you weren't cool 2138 - > when you got into computers.

2139 - > You weren't, but like, but but to the world in there, like it 2140 - > was your world, right? 2141 - > And you like techno and and all that stuff. 2142 - > It was just like there's a counterculture to it all that I 2143 - > jived with really, really well. 2144 - > Like all your friends were getting real jobs at the banks 2145 - > or no and gas or whatever.

2146 - > SPEAKER_02: No, it's non-conformist. 2147 - > Yeah, you have to like you have you have to have contrarian 2148 - > opinions. 2149 - > If you have opinions that everyone else has and then 2150 - > you're right about those, great, you don't you don't exactly it 2151 - > doesn't change anything. 2152 - > SPEAKER_05: Exactly.

2153 - > SPEAKER_02: If you have contrarian opinion, you're most 2154 - > likely wrong, usually in contrarian opinions. 2155 - > But when you're right, yeah, there's a moment. 2156 - > SPEAKER_05: Exactly. 2157 - > You get you get all the upside, right?

2158 - > Um, so I think that that is I think that the founders have 2159 - > that in them. 2160 - > Um, but I mean, exact i the thing to remember is like for 2161 - > every successful founder, there's like thousands that 2162 - > haven't found it. 2163 - > Yeah, probably because they were wrong, or they just they 2164 - > couldn't get lecturing. 2165 - > The timing wasn't right, you know, you know, the way the wave 2166 - > didn't show up.

2167 - > SPEAKER_02: They built a surfboard and they were just too 2168 - > early or too late to to the wave. 2169 - > Yeah, yeah. 2170 - > SPEAKER_05: I think in terms of okay, so let's let's go to the 2171 - > the team and culture. 2172 - > I think uh I mean honesty, you know, like we are trustworthy.

2173 - > That gets into honesty, that just gets into um if you just 2174 - > need to be able to get the team to like especially your media 2175 - > team is like to just to just trust you. 2176 - > Like you just can't play games, you can't, you just have to be 2177 - > brutally I I do that with um I say not brutally honest, Mr. 2178 - > Ronta, but just like completely honest and like candor, 2179 - > radically candid. 2180 - > SPEAKER_02: Yeah, you can use it, yeah.

2181 - > SPEAKER_05: And I I think I'm like I'm an oversharer, but it's 2182 - > part of like how I build trust, where it's just like I'm sending 2183 - > pictures of of of of of my kid and like here's what I do. 2184 - > And like I'm just like I'm like oversharing everything with with 2185 - > with my team all the time. 2186 - > Like I kind of let them into my life quite a lot, but it's just 2187 - > like it's it's just like letting them, it's building a certain 2188 - > level of trust, like this who I am, this is who I am through and 2189 - > through.

2190 - > And like they they know me pretty well at this point, so it 2191 - > it builds that confidence for them to be able to have honest 2192 - > conversations with me and and just to be themselves too, 2193 - > right? 2194 - > Um, and then finally, last one is on on the mark strategy. 2195 - > SPEAKER_02: On the strategy, like the positioning, the 2196 - > strategy, what you focused on, what you didn't, yeah. 2197 - > Could be product, could be market.

2198 - > SPEAKER_05: I so I'm I'm biased, and this kind of goes back to 2199 - > first point. 2200 - > Like, I love a contrarian viewpoint. 2201 - > It's like it's it's just like it's funny, you see that in the 2202 - > in the investment world, the startup world, whatever. 2203 - > It's just like they all talk about disruption, but man, do 2204 - > they like their like boxed models?

2205 - > Is our model that we know works? 2206 - > This is best practice. 2207 - > We exactly right. 2208 - > It's like it's that's like we build vertical software for 2209 - > this, and then we're gonna do this sale, this and and and 2210 - > investors love that, and then and it's just like, yeah, but 2211 - > everybody else is doing that.

2212 - > I think that goes to like the harder path where it's like do 2213 - > something that's really hard and like because then there'll be 2214 - > less people trying it. 2215 - > SPEAKER_01: Like it's just less competition, yeah. 2216 - > SPEAKER_05: And it's like for us, it's like we went into the 2217 - > we try to build a payments company from scratch, and it's 2218 - > like, yeah, it's brutal, but I think it's paying off. 2219 - > Yeah, and I love startups, like I love startups with hardware.

2220 - > I mean, there's the word hard in there. 2221 - > Yeah, I just love when I talk to founders and I had this 2222 - > privilege now of like um I get you'd be a bit more prominent uh 2223 - > uh founder in in our market, so I get to meet lots of other 2224 - > founders and young people, and it's like, and and when the ones 2225 - > that bore me are the ones that are just like uh we're making a 2226 - > CRM for this and this and that, and you're just like that's 2227 - > fine, like go.

2228 - > You'll make some money, go yeah, yeah, but it's the ones that are 2229 - > just like we are doing X, and it's just like, and you're just 2230 - > like you look at them sideways and you're just like it might 2231 - > not work, but like yeah, good on you for trying. 2232 - > Yeah, but if it but if it does and they're trying something 2233 - > that like very little other people are trying to solve, and 2234 - > I love that. 2235 - > SPEAKER_02: Yeah, yeah. 2236 - > Well, Nick, we've had a wonderful conversation here.

2237 - > Um, what's next for Hellsome? 2238 - > Just take me into the future. 2239 - > What's uh what is 2025 and beyond? 2240 - > What's the next three years, four years?

2241 - > What are you excited about? 2242 - > What are you most looking forward to? 2243 - > What battles, what battles, other Goliath, are you looking 2244 - > forward to? 2245 - > Give me a pitch into the future to to to end our episode.

2246 - > SPEAKER_05: Um I'll leave you with this. 2247 - > So um it's just part of 26. 2248 - > So like we are really liking this concept of something we're 2249 - > calling open payments, which is around like you hear about open 2250 - > banking and what what's open banking about? 2251 - > Open banking is really about like giving um optionality to to 2252 - > customers about like their data and who they they they get 2253 - > service and portability, and uh and and we're taking a similar 2254 - > approach to payments, and we're about to hit that in a very big 2255 - > way uh in the market where um we are we've really looked at like 2256 - > how we're operating in a market.

2257 - > If you think about like say a square, square really makes a 2258 - > like a little walled ecosystem, little walled garden all in one, 2259 - > like here you use our stuff and and so on, right? 2260 - > And what we've realized in part because we're servicing so many 2261 - > different types of businesses, way more businesses than the 2262 - > average. 2263 - > So, like like you know, I was describing like it's like 2264 - > whether it's like a wholesaler or a or a vet or plastic surgeon 2265 - > or like an auto dealer or whatever, right?

2266 - > It's kind of like we're never gonna be able to make all the 2267 - > different software that they need. 2268 - > And there's gonna be people that could specialize in that. 2269 - > But what we want to do is meet them where they are and be the 2270 - > absolute best payments and financial services company that 2271 - > we can be for them. 2272 - > And this is gets into the idea of like there's still a lot of 2273 - > walled gardens in the industry, yeah, and we're about to like 2274 - > drive right through those walled gardens.

2275 - > You want to tear down the walls, and and I think that's my that's 2276 - > the next, the next David and the Goliath. 2277 - > I like it. 2278 - > SPEAKER_02: I love it because I think the the theme that goes 2279 - > into that is that the Davids often arm the rebels. 2280 - > SPEAKER_05: Yeah, so you want to tear down the walls and arm the 2281 - > rebels, you know, like the and and ultimately serve there's 2282 - > really like one thing driving us, which is ultimately like be 2283 - > the world's most loved payments company and and serve small 2284 - > business customers that are you know being taken advantage of or 2285 - > not being well serviced like every day.

2286 - > And anything that gets in our way of that, we will headbutt 2287 - > until we get there. 2288 - > SPEAKER_02: So that's amazing. 2289 - > Well, Nick, I'm rooting for you. 2290 - > We're excited to have been part of your journey to continue to 2291 - > help support your leadership team and their growth and their 2292 - > learning.

2293 - > And uh let's see, we're excited to see the next this next 2294 - > chapter. 2295 - > So thank you for being part of our show. 2296 - > Thank you for giving us a story to our audience and uh and being 2297 - > here today. 2298 - > SPEAKER_05: Thanks for hearing the story.

2299 - > Appreciate it. 2300 - > SPEAKER_02: Awesome.