The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Startups & Founders/Precursa
Precursa artwork

Entrepreneur Experience: Nathan Beckord, Bootstrapping to Investors

Precursa · 2022-08-19 · 46 min

0:00--:--

Key moments - from our scoring

Substance score

47 / 100

Five dimensions, 20 points each

Insight Density9 / 20
Originality7 / 20
Guest Caliber12 / 20
Specificity & Evidence11 / 20
Conversational Craft8 / 20

Nathan Beckord walks through the unglamorous reality of fundraising that most founders discover too late. FounderSuite, his venture-backed SaaS platform launched in 2016, has helped users raise over $3 billion by providing an integrated stack of tools - including investor CRM, a 200,000-investor database, pitch deck hosting, investor update tools, virtual data rooms, and downloadable term sheets. Rather than pitching FounderSuite as a silver bullet, Beckord emphasizes that founders should bootstrap as far as possible, build customer validation before approaching investors, and understand that fundraising requires talking to 100+ investors with only a 5-6% conversion rate (he pitched 200 investors to raise his seed round). He discusses the consulting-to-product path his own company took, running on a two-year cycle of consulting revenue fueling product development, and how the first 2-3 years of any startup are brutal before momentum compounds. For B2B founders considering capital raises, this episode offers practical benchmarks: validated customer traction, market size assessment, and the realization that investors fund relationships and vision, not desperation.

Key takeaways

  • →Most founders pitch 100-200+ investors to close a round, with a typical 5-6% conversion rate, meaning you'll be rejected 95% of the time - this is normal and expected.
  • →Bootstrap as far as possible before raising money; the further you get without capital, the more leverage and ownership you retain, and never raise from a position of desperation.
  • →Customer validation - even without revenue - is more valuable than early-stage ideas; showing traction metrics like user growth and negative churn (users bringing friends) significantly improves fundability.
  • →Approach investors as partners in an interview process where you're assessing fit, not begging for money; frame it as 'I have momentum and I'm interviewing the best partners' rather than 'if only I had capital.'
  • →SaaS is ideal for bootstrapping because you can charge from day one with a landing page and Stripe integration, whereas hardware and physical products typically require early capital raises.

Guests

Nathan Beckord

Topics in this episode

FounderSuiteInvestor CRMPitch deck hostingVirtual data roomsInvestor database (200,000+ investors)Investor update toolsFriends and family roundsSaaS bootstrappingCustomer validation metricsVenture capital conversion rates

Questions this episode answers

How many investors do you need to talk to in order to raise a seed round?

You typically need to pitch 100-200+ investors, with a conversion rate of about 5-6% (meaning 95% will reject you). Beckord pitched roughly 200 investors and closed one seed fund plus 10 angels, illustrating this is normal and expected.

What early-stage indicators show a startup is ready to raise venture capital?

Look for product-market fit signals: a working prototype, customer validation with users returning and using the product repeatedly, traction metrics (like 10,000 users by month three with near-zero churn), and ideally a large addressable market - though the bigger the market, the better the investment case.

How can founders build software products without $200k upfront capital?

Options include: bootstrapping via consulting (working full-time on your day job while saving chunks to pay developers), building it yourself if you're technical and starting with Stripe/landing page SaaS, or raising a friends-and-family round from 10 people willing to write $20k checks each.

What's a common mistake founders make when approaching investors?

Saying 'if I had money, I could do X' frames you as desperate and begging. Instead, position yourself as already in motion with momentum, interviewing investors as potential partners, and suggesting they'd be lucky to get into the deal - this flips the power dynamic.

How long does it typically take before a startup's fundraising effort becomes easier?

The first 2-3 years are brutally hard with constant rejection and setbacks; Beckord reports working 80-hour weeks early on that eventually dropped to 50, then 35 hours - reaching 'easy' took roughly six years of iterating, improving the product, and repeating the cycle.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

9 / 20

There are a handful of genuinely useful data points (5 - 6% investor conversion rate, 50 - 100 hours of research for a target list, two failed raises before the third succeeded), but large stretches of the episode are padded with common startup platitudes, the host's personal anecdotes, and filler reassurance. The insight-to-minute ratio is low.

I pitched about 200 investors and ended up with one seed fund and 10 angels coming in on the round. So, okay, if you do that Math, that's about 5% of the people I pitched came and write a check.
I always feel like I'm contradicting myself because you need to talk to a lot of people, but they need to be highly researched, highly focused

Originality

7 / 20

The episode recycles the most common startup-podcast advice (talk to customers, be passionate, bootstrap before raising, investors as partners not ATMs) with minimal contrarian or first-principles thinking. The equity-to-power-users tactic and the 'dam full of water' VC dry powder framing are the most novel moments.

he's giving a little bit of equity to, and I don't know what the number is called, the top hundred top thousand power users of his product who are then kind of going to be his advocates
I get excited a little bit about a downturn. Like, okay, cool, wow, I might be able to get some better talent now.

Guest Caliber

12 / 20

Nathan Beckord is a genuine practitioner - 10 years as interim CFO for 150+ startups, then bootstrapped and scaled a real SaaS product with verifiable traction ($3B raised on platform, 200k investor database) - which gives his advice grounding. He is not, however, an elite-scale operator or a recognized category-defining figure; he occupies solid mid-tier practitioner territory.

I pitched about 200 investors and ended up with one seed fund and 10 angels coming in on the round
I actually tried to raise Money two times based on what I had, I thought I had enough and both times failed. So it wasn't until the third time that I was actually successful

Specificity & Evidence

11 / 20

The episode has a respectable but uneven level of specificity: the 5% conversion funnel, $30k developer tranches, 200-investor pitch count, and the Crunchbase 42% stat (introduced by the host, not the guest) are concrete anchors. But many claims are approximate, anecdotal, or hedged ('something like that,' 'I'd have to go back and look at my calendars'), and the macro-level advice is largely unquantified.

I pitched about 200 investors and ended up with one seed fund and 10 angels coming in on the round. So, okay, if you do that Math, that's about 5% of the people I pitched came and write a check.
I would wire that cash to some developers in Poland in chunks of like 30k and they would build some stuff for me

Conversational Craft

8 / 20

The host asks serviceable, topically relevant questions and uses a stat-prompt device effectively, but she frequently redirects the conversation to her own story rather than pressing Nathan for deeper specifics, and she never meaningfully challenges a claim or follows up on vague answers. The result is a friendly, unchallenging chat rather than a probing interview.

I want to give you a statistic and then I want you to tell me what you think about it
So this is new for me. I know it's new for, you know, you even talk about yourself. That is it. 98% of founders are raising for the first time, which is why we're all so bad at.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker B62%
  • Speaker A38%

Most-used words

money34investors30back22founders22building21build21founder20start19customers19love16startup15first14market14journey13thank13raise13

Episode notes

Does it really take over 100 conversations in order to raise capital OR are there some secrets? Host Cynthia Del’Aria talks with Nathan Beckord , the CEO of Foundersuite.com a venture-backed company that makes the leading “funding stack” that includes, investor database, CRM, pitch deck hosting, and Investor update tools for startups. On this episode. Nathan shares some insights from his entrepreneurial experience raising capital from investors, tips on whether to start bootstrapping and grow your business versus finding investors plus how entrepreneurs can know they're truly ready for an investor. Listen and enjoy! Resources from this episode How I Raised This podcast - Paul Graham essays - This Week in Startup Hosted by Jason Calacanis & Molly Wood - Be sure to like, share, and

Full transcript

46 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Straight to you from Denver, Colorado. This is Precursa the Startup Journey. We share the ins and outs of building a tech startup from inception to launch to revenue and beyond. If you've ever wondered what building a startup from scratch really looks like, you're in the right place. With full transparency and honesty, we reveal it all about Bricursa on our ride from idea to exit. The wins, the lessons learned, and the unexpected twists and turns. Hello everybody and welcome back. This is precursor the Startup Journey. I'm so excited about my guest today, Nathan Beckord. And Nathan is the CEO of foundersuite.com, which I know we've talked about before, but I'm really excited because he's going to talk about it more. His his company is a venture backed company that makes the leading funding stack for startups raising capital. Since launching in 2016, users have raised over 3 billion in seed and venture capital on the platform. Prior to starting founder suite, Nathan spent 10 years working with over 150 startups as interim CFO, business developer and advisor. Nathan has a ton of fancy degrees and probably some letters behind his name, but. But more importantly, he's climbed the mountain that so many of us entrepreneurs are attempting and he's built excellent products to help other entrepreneurs do it as well. So without further ado, welcome to the show, Nathan.

Speaker B: Thank you very much. That might be the best intro I think I've ever received. So that was great.

Speaker A: Awesome.

Speaker B: I love that.

Speaker A: I love that intros are my favorite part because you and I get to know each other, but you also get to see like how excited I am for my, my audience to get to hear from you. So why don't you just start by telling us little bit about yourself, how you became an entrepreneur and sort of what that journey looked like.

Speaker B: I grew up where you are in Colorado and I was always kind of a little hustler as a kid. Like I, uh, I think I'm sure we did the lemonade stand, but I always had some little side hustles going selling like martial arts stuff out of catalogs to other kids whose parents wouldn't let them have, you know, Chinese throwing stars and stuff like that. Uh, borderline legal, you know, business when you're 14 or 10 or whatever. It's always had a little bit of an entrepreneurial bug. My parents, my dad was a doctor so he really didn't have entrepreneur parents like a lot of founders do. But you know, really just love this idea of making money and creating businesses, but then went away to college and went down a path into investment banking, which I, I thought I wanted to be. It's, you know, it appears very glamorous from the outside and it is actually a pretty glamorous career. But like, I liked investment banking, but I never loved it. And so I wanted to get back to kind of the entrepreneurial path. And it took me a while, took me over a decade, but then finally had this idea. So let me back up. While doing investment banking, I was helping companies raise capital. That's what investment bankers do. And working with later stage companies, taking some public, some of them raising, you know, later stage, like C round, D round, mezzanine round, then went off from investment banking and actually started doing that for earlier stage companies for about a decade through a consulting business. And that was called Venture Archetypes. And then kind of had this idea on the side, like, why don't we build some products for this? Right? We're helping those companies raise capital. You're a customer, you're coming in the door. We're building a pitch deck for you. We're building a financial model. I'm, um, creating a list of investors, putting it all in a fancy spreadsheet to help you track all your conversations with. Why is this in a spreadsheet? Why don't we build some tools for this? So that's kind of, ah, where we started to launch Founder Suite. Really eating our own dog food. And it, you know, it was like a side hustle for two years or so and then spun it out into its own company and the rest is sort of history. So that's awesome.

Speaker A: That's a dream. So tell my audience a little bit more about what Founder Suite does. We've talked about it before because when Precursa was considering doing some fundraising, we actually went on to Founder Suite and kind of poked around a little bit and we were like, okay, this could be an option. And, and my background just so, uh, you know, Nathan is I. I have historically bootstrapped every one of my companies. And so wading into the investment waters is like a little bit overwhelming to me at times. And so, you know, like, three different times we had a lead investor on the hook and then they sort of ghosted us three different times. And I finally was like, you know what? We've got cash flow for my other businesses. Let's just keep doing this in the bootstrapped way. So this is new for me. I know it's new for, you know, you even talk about yourself. That is it. 98% of founders are raising for the first time, which is why we're all so bad at.

Speaker B: Yeah.

Speaker A: So talk about what Founder Suite is and how do entrepreneurs know when they're ready?

Speaker B: Yeah, those are. These are all great questions. So what is it? I'll start with that. We started with basically replacing the spreadsheet, right. That was our first product. We came out and launched an investor CRM, which is really like a tool to manage a pipeline of investors. All the discussions, actions around that. And we've since. And that was six years ago. We're kind of old in startup time, but that was six years ago. Then we've been launching other products ever since. Then we launched a database of investors, about 200,000 investors in our database. Now we launched a, uh, pitch deck hosting tool so you can put up your PowerPoint or PDF and send out your pitch to investors. We launched an investor update tool for doing like follow up stuff with investors. Especially after you raise money. You got to start kind of keeping them, um, in the loop. Email tools, a virtual data room. When you get into due diligence, you really want to be sharing like the confidential information in a really secure way. So we got a product. So to back up a bit, what we've basically done is like taken each step of the fundraising process from A to Z and built products around that and so, and trying to help folks like yourself. Like we just talked about most founders, you know, fundraising is not rocket science, but it is hard. It is actually much harder than people think. It will be a lot of pain involved.

Speaker A: Uh-huh.

Speaker B: We can go off on a tangent on that. But if you think about it, you know, what do you do? First you build a target list of investors. So that's what the database is for. Then you've got to have a way of managing them. You're going to be talking to 200, 300 investors. So that's the CRM. And then the communications are the email tools. The pitch deck hosting the investor updates, that's sort of your marketing tools. And then the data room is for the due diligence. So it's kind of mapping that. And then we also have a collection of like downloadable term sheets, cap tables, things like that for really finishing touch on it. What was the other part of that question? I forget already.

Speaker A: How does an entrepreneur know when they're ready? Right. Or like, you know, because so I work with really early stage founders, right. Like these are people who are like, I have this idea and I'm like, great, let me help you figure out if you have some indicators of early product Market fit. Let me figure out if there is an ROI here and I get them to the point where they have a launch plan, they have a performa, they know where they're going for. Not every entrepreneur is ready at that point to raise money, but some of them are. Right. And so how does it, how does an entrepreneur know when they're ready to raise money and when just to pitch Founder Suite? Like when they're ready for Founder Suite?

Speaker B: Yeah. Um, no, it's a good question. It's. There's not a precise concrete answer to that. Like I think you have to. And this is hard to do when it's your own start, but you have to sort of take an objective step back and look at if you put yourself in the shoes of an investor, what is of value here? What is of interest to this for some people. I just had a guest on our show yesterday, he's a third time founder and he's had success. So don't. For him it almost doesn't matter what the company is, he's had success. So it's purely him as the team. For a lot of first time founders, they don't have that. Right. So taking an objective step back, like what have you got here? If you put all the little pieces on the table, is it a big market that's always good. Is it a working prototype? Have you built something that ideally you've built something and you've got some customer validation on that. Even if you might not have revenue yet, but you've got people using it coming back and using it more and more, that's always a good sign. And then you know around that, what's the market look like? Right. So if you've got something just because you have something that is working and people are using it, if your market's really niche, that might not be a good fundable business.

Speaker A: So yeah, because it's hard to make money doing that. Right. It's hard to, it's hard for an investor to come in and say, yeah, I'm going to put 2 million in when your market cap is 10 million million. Because it's very hard to ever see a return on that money.

Speaker B: So there's no hard and fast answer that. There's also kind of the function of like when do you need the money? Can you like you've done bootstrap it as far as you can. The farther you can bootstrap it, the more control, ownership you're going to have, the more leverage, the more power, right? I mean, that's good to bootstrap it further. The worst time to raising money is when you're like, desperately needing money and you have no leverage. Right. Because it's kind of like a bank, right?

Speaker A: Yeah.

Speaker B: If you don't need the money, that's when they want to lend to you.

Speaker A: Right.

Speaker B: A little bit like that with venture funds, too. So it's hard. I mean, you can raise money on kind of something very early and maybe just beyond the idea stage. But you better have other factors that are really going to investors excited, like your team, like your background. If you don't have that, I really do recommend getting customer validation. The more you can put up a slide. Yeah, that shows. Hey, we launched in October. By December, we had 10,000 users on this and they were coming back. Our churn was almost nothing. It was actually like negative churn. Cause they're telling their friends. And then by April, we had, you know, 50,000. Like, that's exciting. That's going to get someone's interest at least.

Speaker A: So that totally makes sense. And so Founder Suite is a software company. It's a, uh, it's a SaaS company. Talk a little bit about how can you get to that point. Like, what do you have recommendations for entrepreneurs who are maybe. Maybe they're like, I don't have $200,000 to build, you know, an initial software product. Like, how can they get to that point without having a lot of money in the beginning? Because that always feels like the chicken and the egg thing. Right. Which is like, you need to have some kind of proof. But if you don't have 200 grand to put into software, or 50 grand put into an app, or it's sort of like, where is that line where proof is enough that people could legitimately, like, get creative and get scrappy and bootstrap?

Speaker B: It's tough. There's no easy answers to this. You have to. I'll give you. I'll give. Just our story. Like, when I was starting this, and this lasted probably close to two years, where I had the consulting business, and literally I'd go work 60 hours a week doing the consulting, I would save up a little kitty of cash, and then I would wire that cash to some developers in Poland in chunks of like 30k and they would build some stuff for me and then I would be out of money and so I'd have to kind of go back and consult. And we did that for a long time to get something off the ground.

Speaker A: Yeah.

Speaker B: And, you know, I don't always tell the story, but, like, I actually tried to raise Money two times based on what I had, I thought I had enough and both times failed. So it wasn't until the third time that I was actually successful in getting a VC to commit and some angels commit. So there's my journey. Right, then that's, that's one scenario. You bootstrap, you consult, you keep your day job, keeping the rock moving, rolling forward a little bit until it starts to kind of roll on its own, then go start to talk to investors. I mean, there's other ways to do it. There's some businesses like, especially like SaaS businesses, if you're able to develop it yourself. Right. You can get this going and start to set up a, uh, landing page and a stripe integration and you can start to charge basically from day one. So some businesses, basically you can bootstrap from, from nothing. That's obviously harder. If it's like products or hardware, you know, you kind of need to raise money for that. And then of course there's a friends and family. Right. So you just. This is a very, very common thing. Not everyone is comfortable with it, but if you have 10 people in your life that can write you $20,000 check, my dad, full disclosure, did write a $30,000 check. I think like he did invest and no one, no other family member. But, you know, if you've got 10 people that can write $20,000 check, there's your $200,000, um, to get going. And, and yeah, ah, you better make them proud because those Thanksgiving dinners are going to be awkward if you lose their money.

Speaker A: But yeah, so it's interesting because you said you, you did that sort of cycle of like, build up capital, do some building. Build up capital for almost two years, if I heard you correct. Was that, uh, did I get that right?

Speaker B: I had to. Yeah, it's something like that. We started and it took a while until we. I'd have to like go back and look at my calendars. But, but something like that, it took a while until we were able to get off the ground.

Speaker A: Yeah. And, and, and I love that you called out consulting. Right. Because, because the thing that I'm always trying to get entrepreneurs to understand is if you really have something that you think you can productize, you should be able to go do that in exchange for, for money as a consultant or in some kind of consulting capacity. Almost as like another proof point. Right. I mean, that's what we do at Precursor. Like our, our whole business is based on fractional work with founders, coaching and advising startup founders at early stages, helping them build Their ideas. Right? And we're about a year and a few months into our build and experiencing the same thing. So we're just like cash flowing everything we can. Right. And building as much as we can along the way. And we're probably about six months out from actually having the platform done and ready to launch so that then we can start getting early users into the platform, start showing that traction. Right. So talk for a minute about the overnight success myth. I hear this all the time. And the most recent one that sounds the most ridiculous to me is when Sarah Blakely sold the majority stake in her company to Blackstone back in November, December of last year, all these stories started to come out about Sarah Blakely as this overnight success. And I was like, yeah, 21 years later. Yeah, so talk about that a little bit, because entrepreneurs, we get caught up in that. Like, I'm going to build this thing and in a year I'm going to sell it for $1 billion and I'm going to be Elon Musk or, you know, I'm going to be PayPal. Right. That really is extraordinary. What is a more typical founder journey looking like? I mean, you've worked with a lot of founders. You build tools for founders. You have a ton of data on this. What does this really look like?

Speaker B: Yeah, it's a lot. It's a lot messier, a lot less linear, if you will, you know, than. Than it always looks when you're reading TechCrunch. I think I said this. I think I was talking to one of our customers the other day, and I said something to the effect of, um, if entrepreneurs really knew what it was going to be like, they wouldn't even start down that path. They would keep their day job because it is so much harder, more stressful, more pressure, more roadblocks, more just setbacks, rejection than you can possibly imagine. And it is like that for. Usually from my experience, for the first, call it two, two to three years of the journey. And then. And again, I'm using founders, for example, those first two or three years were so hard. We kind of ran out of money a few times. And then finally. But you just keep. That cycle is continuing. We're generating some money. We're putting that right back into the product. We're talking to customers, we're. We're getting what their pain points are, we're improving it. And, uh, this is great for SaaS is why I love software as a service so much, because, like, the product can kind of cumulatively get better.

Speaker A: Yes.

Speaker B: But I think Most products are like that, too. And eventually it gets good enough. There were a few multiple times where I'm like, I think we're good enough now. Like, I think we actually have something, and of course it wouldn't be quite good enough. Then a few, you know, six months later, like, I think we're maybe good enough now. Yeah, yeah. But eventually that just compounds and you keep repeating that cycle day in, day out, 52 weeks a year, and eventually it does kind of get good enough and the thing starts to start to lift on its own. But those first two or three years are going to be brutal. People rejecting you, people, you know, people getting angry at you, customers getting angry because it. The app quit in the middle and you lost all their data or whatever it is. Right. Um, I think we all live in fear, or at least I will, that someone's going to publicly post on Twitter, you know, some horrible story, and we're. We're dead. Yeah. Um, so. So that's. That's one thing. I mean, I think if I could also graph the hours I've worked, especially in those first few years, it was 80 hours a week, then it's 60, and then it's 50, and now it's more like 35 or something like that. Right. It just gets easier. But that's six years for us until it's sort of easy. So I think that's pretty con, you know, to spend too much time on this. But if you hear the origin stories, go back and look up the origin stories about even Airbnb and Twitter and some other ones. You know, Airbnb was like, sleeping on friends couches, printing up cereal boxes to try and, like, generate some revenue, doing all kinds of crazy stuff because they didn't really have a functioning business yet, but they just kept hustling and sleeping on couches and saving money and until it got good enough and obviously the rest becomes history.

Speaker A: History. Yeah. That's awesome. So you mentioned something a minute ago, and I kind of want to come back around to it, which is you said, you know, you have 200, 300 investor contacts, conversations you're having. Does it really take 100 or more conversations in order to raise money? Or are there some secrets you've learned doing what you do?

Speaker B: Yes and no. I mean, the more you spend upfront, doing the research, really doing the research, digging in, going through investors web pages, bios, everything, and really identifying the short list of, uh, people who exactly do your industry, your stage of business, your geographical location. Sometimes that matters, sometimes it doesn't. Really identifying the perfect fit investors, the fewer number of investors you need to go talk to.

Speaker A: This is Sarah Hubbard, host of youf and Me Kid, a podcast about starting and raising a family on your own. We just launched season two and I'm speaking with single moms, those still considering, and experts in relevant fields to give you a real sense of what the day to day experience of solo parenting looks and feels like. Plus, this season I've partnered with California cryobank, the number one sperm bank in the U.S. so wherever you are in the process, this podcast provides some support, humor, and helpful information. Listen to you and me, kid, wherever you get your podcasts.

Speaker B: So, having said that, most startups still need to talk to at least a hundred, often more than that. Um, and one of the metrics I throw around a lot is, and this is true for us, I pitched about 200 investors and ended up with one seed fund and 10 angels coming in on the round. So, okay, if you do that Math, that's about 5% of the people I pitched came and write a check. And so that means I got rejected 95% of the time. And that's actually pretty typical. I've seen that 5 to 6% conversion rate, kind of the funnel, if we think of it like a funnel, 5 to 6% conversion rate between who you pitch and who writes a check is actually pretty typical. So that if you back into it, if you need a certain amount of money and you need a certain number of investors, you can kind of figure out how many you need to talk to to get to that. That amount. So.

Speaker A: Yeah, so what you're telling me is there's no shortcuts and anything worth having takes work.

Speaker B: Yes. And, and people do take shortcuts all the time. People say, okay, well, you just told me I need to talk to lots of investors, so why don't I just send out an email blast to, you know, cold email to 5,000 investors?

Speaker A: That's not gonna work.

Speaker B: That's actually not gonna work. Yes, you need to talk to lots of people, but not that way. And so I always feel like I'm contradicting myself because you need to talk to a lot of people, but they need to be highly researched, highly focused, and then you should start to have success. But not, not any variations from that.

Speaker A: Yeah, because, because investors are about relationships. This is not, hey, I meet you, you're going to give me $5,000 or $10,000 or $20,000 or $100,000 or whatever, and then we're never going to talk Again, this is now becoming your boss as the founder of your company in a lot of ways, where they are now expecting you to deliver on the thing that you said. So it's a relationship. You, you want to take the time to build that, to understand who's the person on the other side of the table. Do I trust them? Do I think they really understand the vision and that's what they're buying into, or do they have some other motive? And this is why I always feel like I'm trying to explain to people, you aren't going to investors begging for money. You're going to investors because there's a, uh, there's a trade that's going to happen. You have something of value, they have something of value. And we want to create a relationship that, that forwards everything. We're both for the future, right?

Speaker B: Yes. I like that. And let's touch on that, because I think if you do go begging for money, and this is another mistake I see folks make is they go say, if I had some money, then I could do xyz. And that's, that's not exactly begging, but it's kind of in the category of begging. And investors just get turned off on that. Really what you want to do is like, hey, I've got this awesome thing that's already in motion and I'm looking for partners to kind of help me take it to the next level. And I'm interviewing folks basically, and you know, I'm going to let in some of the, the best people. Right. Like, in other words, you as the investor. I'd be, you'd be lucky to get in on this deal. That's because I'm coming from a position of strength. I've got something going versus, hey, I really need your money. If you gave me money, I could build something, you know, could you give me some money? It's a terrible position. Yeah. Please.

Speaker A: So, uh, may I have some more?

Speaker B: But, but you also touched on something. I mean, you're absolutely right. This is a five to ten year relationship you're going to have. They can be friendly, but they can also not be your friends. You know, I've seen. Kind of depends on the, the structure. If they have a board seat and stuff like that, but they have influence over your business, they can potentially fire you if, uh, obviously if they control enough of the board and stuff. Like, it's not always a friendly situation. So you need to be choosing partners wisely.

Speaker A: That's good advice. So what would you say that is the most important lesson that you've learned as an entrepreneur throughout your journey.

Speaker B: I think something that has worked pretty well and it wasn't obvious to me at first. Took me a while to kind of discover it, I guess, is like, when in doubt, just spend more time. If you're confused about what you should be doing. When in doubt, spend more time talking to your customers, really just sitting down with them. Um, I still. People get surprised all the time because we use Intercom for our customer support on our app. And I'll be responding to people like, wait, are you the CEO of this? And you're responding to my question about importing my CSV? And I'm like, yeah, yeah, I'm here all the time. Like, in other words, I'm still doing a lot of customer support. And I love it because I'm really understanding where people are getting stuck, what people are doing, what people are trying to do. Going off a little tangent, we're redesigning this metrics dashboard page, all the deal metrics you want to see about your fundraise. And I'm talking very closely to, like, three or four customers who have had requests for things in the past and getting great ideas from them directly from their brains. That's going to feed into our product. Right. And if I was like, four steps removed from. From that process, with a bunch of layers in between me and the customer, I wouldn't be able to do that. That's been really critical to me is like, just keeping a close pulse on the needs and wants of your customers and talking directly to them, meeting them for coffee. If you're. If you're in Denver and you know some great customer power, customers there take them out for lunch and just pick their brain about what they're doing and where they're stuck and stuff like that. So that's always a good default. Yep.

Speaker A: I love that. And I just wanted to. So we talk a ton about talking to customers. Like, it's like the number one thing. And what's funny is, you know, you said earlier, if you're a technical person, you can kind of bootstrap by building something yourself. Those are the people who tend to talk to customers the least. But who would have the most to gain from talking to a customer? Because the problem when you're. When you're a founder sort of in your own silo, you think you know what's most important and you have this vision, but it's actually the customer who has to pay for it and use it. And if they aren't represented in that vision in Fact, the bulk of that vision, then you're going to miss the mark and you're never going to hit that traction point. Right.

Speaker B: That's so true. I'm glad you brought that up because I feel like that's a mistake we made in the early days, is like, oh, I know fundraising, I know how to raise capital. I have all these ideas for what this product should be and I kind of just wanted to build these ideas almost in a vacuum. And we, we did build some stuff that was irrelevant and wasted a lot of time on it. Especially in the early days when resources are so precious, you know, you can't waste engineering or money. That's because I thought I knew what the market should want instead of talking to the customers. So, yeah, reason number 3000, why talking to customers is good.

Speaker A: I love that. So in your opinion, what do you think is the most important personality trait or characteristic that someone needs to have to be a successful founder to play this game?

Speaker B: It's a hard question because you've seen different personality types work in different businesses, Right. You've got like Travis Kalanick, who was probably the only personality who could get something like Uber off the ground, dealing with all the taxis, unions and stuff like that. He's hardcore ruthless, but his personality probably wouldn't work in some other sectors, right?

Speaker A: Yep.

Speaker B: You know, I think, to answer your question, probably the one thing you've got to have is that ability to kind of hustle and sell. That means selling to customers. That means selling to people you're trying to recruit. In other words, selling them on your vision, obviously selling to investors, your vision. It's just that ability to get people selling to journalists, to get them interested and ready about you. That ability to kind of pitch, present, create a, uh, emotional connection to what you're doing and to spread that message out there, because that works across all those layers. Investors, customers, team recruiting, press, everything. So that's pretty important again, that some industries that doesn't matter as much like we have seen some of those technical founders that are really deep in the engineering. You know, they build products that are kind of, I guess, sort of sell themselves. Right. They kind of have a baked in viral model. We had a guest on our podcast, a guy named Richard White, who's a pretty technical guy, and I think he's actually become more of a pitcher, um, than he used to be. But, you know, he's pretty technical and like he actually did something I found interesting where he's giving a little bit of equity to compensate for maybe not being a Natural salesperson he's giving a little bit of equity to, and I don't know what the number is called, the top hundred top thousand power users of his product who are then kind of going to be his advocates and salespeople kind of talking about it, word of mouth. So I thought there was an interesting way to kind of possibly compensate for maybe not a natural salesperson. Like, how can you turn other people into salespeople for you?

Speaker A: Exactly. Because that's, that's really when you start to hit that viral, like you said. Right. Which is not typically something that if you sat down with a marketing company, be like, okay, we're going to make this video and it's going to go viral. Like, you can't really plan that kind of thing.

Speaker B: Yeah.

Speaker A: Uh, but what you can figure out to your point is, can I take the users I do get and turn them into salespeople or advocates or ambassadors or however you want to say that, so that they then tell people and that creates more and then that's how you can create some of that, like building virally. Right. So sales skills are important. If you don't have them, you got to get creative.

Speaker B: Exactly. Perfect summary.

Speaker A: Do you think there is such a thing as products that sell themselves? Is that a thing?

Speaker B: I mean, I'm trying to think of it, right?

Speaker A: Because we hear that all the time, right? Like people say, oh, this thing is so awesome, it's going to sell itself. And in the back of my mind is that, you know, um, this is my sixth startup for. Because I know we don't know each other all that well yet, but I'm like, I've never worked with a company, I've never built anything that actually sold itself. Like, there was always something that had to be done. But that doesn't mean it isn't possible. That doesn't mean that someone isn't like, oh my gosh, I created this thing and it just like blew up. It was like so great. And I don't know how, how I didn't do anything, you know, I mean, like, is that a thing?

Speaker B: So I think founders do underestimate, especially technical founders. They sort of think if I build it, they will come. Right. And. And that often leads to this product standing out there in the universe with crickets chirping around it. People underestimate how much a product will sell itself. However, I think there are, you know, products that have some built in virality. Right. Think about like Zoom or something. I invite you to Zoom. Oh, you just use Zoom. You see, Zoom Branding there, maybe you get a follow up email that kind of sells itself. It has that natural virality built into it. So I guess that's the closest I can think of. You know, things like that.

Speaker A: That's a really good one. All right, I like that. So if you could give other entrepreneurs one piece of advice, what would that be?

Speaker B: Yeah, it's, well, talk to customers. We talked about that already. I won't go back to that one. But I'd say just, uh, pick something you're truly passionate about and hang in there. And those two things are kind of interrelated because, you know, like I said at the beginning of this, it's so much harder, the startup journey is so much harder than you think it's going to be, than any TV show or blog post can indicate to you. It's just going to be exponentially harder. So you have to be doing something that you really are passionate about. Whether or not you get funded. You want to see this thing happen. Whether or not anything happens, you want, you're, you're just committed to this because that will sustain you through those really tough times. And then the corollary to that is just keep plugging away. I mean, I use, I'm really passionate about what we're building and like I, uh, told you, we ran out of money a few times. Had to like scale down to basically zero engineers for a while in the early days, like, but just keep it alive, keep it going and um, pushing forward and you know, sometimes you just have to push through those really hard times and you'll find something on the other side that gets you going. So that's it. Pick the right thing, basically, that you're really passionate about.

Speaker A: Yeah, I love that you are, you're more mature in your journey now. You know, you guys are six years in. You've, you've, you've got revenue for sure. What are your concerns and that other people and how are you handling them might be facing, you know, coming up in this inflationary period. And there's, you know, Sequoia put out this 52 slide deck, basically saying don't try and raise because it's not going to work. You got to make your funds last for the next two years. Like what is going through your thoughts as a more mature founder and what advice would you have for other founders about how to sort of negotiate what's happening right now? Because it is kind of unique, especially if you're a first time founder and you weren't building a company in 2000 or you weren't building a company in 2008 when everything kind of all went. Went to hell in a handbasket.

Speaker B: I love it. There was. I saw this thread on Twitter or on LinkedIn. I'll try and summarize it, but there was a founder that said we're never going to do layoffs, even in a downturn or something. And someone else wrote back, I checked out your bio. You graduated in whatever, 2014 or something. You've never seen anything other than a boom market. Like you're giving advice to other founders, but you've never seen a down market and kind of called him out on that. I thought it was interesting. So I don't know where I'd go with that. I thought it was kind of funny. I mean, I think, uh, you know, we've gone through a few cycles. I think it's always exciting, actually. I'm, in some ways kind of sounds perverse, but I get excited a little bit about a downturn. Like, okay, cool, wow, I might be able to get some better talent now. You know, I might be able to. I've had a couple competitors reach out and like, hey, are you interested in acquiring us? Like, you know, there's opportunity to sort of take some market share from competitors now because we're strong and maybe they're weak. Like I see a lot of opportunity in these sort of downturns, which I get a little bit excited about. My advice though is also like, you know, Sequoia puts out these doom and gloom, winter's coming kind of things. And like I would say don't be super reactionary. Look at your cost structure. Don't just knee jerk, react and slash half your staff because you panic. Don't panic, right? Like take a measured approach and, and keep an eye on it. Like we haven't cut anything yet. I'm watching this, watching very carefully. Like I think June, we actually had sort of a flat month, which is like the first month in a long time we've had a flat month. So I'm m watching. Okay, what's the trend here? Let me see a couple months. Is July, is August also going to be flat to down? September is a fundraising season. So if my revenue isn't in September, then yeah, maybe. Okay, then I need to start really trimming. So you know, don't panic, don't knee jerk, react. Keep an eye on, on the macro environment. And the other reason for not panicking is like we've seen, you know, obviously when Covet hit and the markets crashed in March, April, May of 2020 you know, that was another doom and gloom. Right. Investors said the same exact thing. You need CA sustain you for the next 24 months. And six months later, the startup market was booming again.

Speaker A: Yep.

Speaker B: Even smart people like Sequoia can't always predict the future with, with total accuracy. So again, don't panic. Like, keep an eye on the stuff. Kind of adjust those levers a little more gradually than now. Having said all that, I'm talking about like our business, if your burn rate is really high, you've been like going super hard, spending way more than revenue. You know that's a different scenario. Right. You might have to make more severe cuts if you're going to be out of cash in six months. So that's.

Speaker A: And, and I like that you pointed out that the, the, the fundraising process, it is cyclical. Right. And like I'm seeing this in a couple of my startups that are raising right now where investors are, they check out in the summer just as much as the rest of us do. Right. Like, we've got one. He's like, more. Yeah, even more like, we've got one. We've got one for one company that I'm working with. They're company. And, and he's like, hey, can we hurry up and get like the first conversation in before I leave next week on vacation so that when I come back in September, I have notes to remind me why I wanted to talk to you. And we're like, this is such a weird conversation we're having right now. Right. But, but that's how it is. Like they, they check out in the summer too. And so I'm sure you know that in your business. And so you sort of. I guess what I'm saying is you have to know your market and you have to know the landscape that you work in and live in and play in so that you know what's versus what's actually expected in your business. And, and because that's going to direct you a lot to when you need to panic or not. Right. I mean, we're saying don't panic, but when you need to start getting more aggressive, uh, about action. Actions you're taking.

Speaker B: Exactly. Is the lack of response you're getting from investors because they're all in France on vacation, or is it because, you know, the economy is tanking and going into a recession or combination of both? I think, frankly, I'm hearing that investors are a little watch and wait right now, slowing down in their active. But they still have record. And talking about venture firms have record amounts of cash that they've raised in recent years that they have to put to work.

Speaker A: Yes, they do.

Speaker B: Uh, they don't get to keep it. They don't get it, they don't give it back. They have to invest that money. So it's a little bit of a timing thing, whether that happens immediately in the fall or, you know, more gradually over the next year or so. But if you picture a dam with a lot of water behind it, that water's got to come out. And so it's just a function of timing. Um, so just to riff on that one more, what can you do now? So start to build that target list we talked about. Like, really put in. I used to say to founders, it takes 50 to 100 hours of research to really build a really good target investor list. So start that process now, really putting in the time, searching databases like Founder Suite, like Angellist, Crunchbase, whatever resources you have to identify that, going through your network, you know, searching on LinkedIn to see who you're connected to. Investors, like, there's a lot you can do now to really prepare for either this coming fall or whenever the timing might be right for you.

Speaker A: Yeah, that's awesome. I love that. Okay, I want to give you a statistic and then I want you to tell me what you think about it. Okay? Uh, okay. And the disclaimer is there's no right or wrong answer. It's literally, I want you to just what comes to mind. And what do you think about this statistic? Okay. 42% of startups ultimately fail because no one wants what they're building.

Speaker B: That almost sounds low.

Speaker A: About half of people I tell that to, that's what they say. They're like only 42.

Speaker B: Yeah.

Speaker A: So this, just for context, this comes from Crunchbase and they did a study in 2018, they post mortem to 1,000 startups that failed that year. And of that, about 200 to 300 of them were willing to like, be fully transparent, open their books and all that kind of stuff. And what they found was the number one reason was this, the 42%, because nobody wanted what they're building. A fairly distant second was 33% who ran out of money. So I found that really interesting. More people didn't run out of money. Just they were building really cool stuff. Just nobody wanted it. You know, they had a great team, they had a great vision, they had great founders.

Speaker B: So I think that ties into so much of what we've already talked about. Right. Like, if you, you have a thesis as a founder, you're an entrepreneur, you have an idea of how the world could be different, better, some product that the market needs. I'll, uh, use. I keep going back, but, like, I had this vision, like, we could replace a spreadsheet with a CRM for fundraising. Well, that wasn't necessarily a true statement. That sort of seems somewhat obvious in hindsight. But, like, maybe everyone's happy with using the spreadsheet. Like, that's my thesis is this. But I may not be right with that. You've got to test it out there. And so even though that seems like a high, number two things, one, obviously talk to customers to see if they actually want what you've got. You can do a lot before launching, landing pages, customer research, interviews, focus groups before starting an actual startup. And number two, you know, I think that's. That's fair because you're putting ideas out there and the universe may embrace them or may not, but if you don't try, you won't know. You know? Yeah, I wouldn't be so, like, concerned, like, oh, my gosh, this failed. I'm in that 42% category. At least you tried. Like, I know tons of people who are, like, have been talking about their startup ideas for years, decades, and they haven't done anything. So, like, at least you tried. You got in the ring.

Speaker A: Uh, that's awesome.

Speaker B: I love it.

Speaker A: Do you have any other, like, podcasts or books or resources? I know you have a podcast if you want to talk about that, so that our listeners can go become listeners of yours as well. Like, what other resources would you recommend for people who are interested in learning more about getting investors into their startup or just learning more about building a startup? Our audience is about 40% people who are like, I have this idea. I'd really love to do this, but they haven't pulled the trigger yet. And, like, 60% people who are either in their first journey or their serials, and so they're constantly learning, like, what. What would you recommend for folks? Yeah.

Speaker B: Oh, there's so much out there these days, which is really amazing. Kind of hard to sort through and overwhelming. Overwhelming. Um, yeah. I mean, back in the day, it was much harder. Anyway, I won't talk about. I won't talk about the old days, but the old days I will. Okay, so two things. I'll plug ours just for a sec. We do have a podcast called How I Raised it, and it's kind of a homage to the How I Built this. But it's. It's called How I Raised it. It's on iTunes, Spotify, SoundCloud, YouTube. You should be able to find it on YouTube or just search for founder suite.

Speaker A: Perfect.

Speaker B: But it's basically 240 interviews with founders on how they raise capital for the business. It's very, very niche. But I love it because I thought I knew everything about raising capital. And then I start to interview people like, wow, that's an interesting tactic you took. That worked. And just so much stuff. We really get into the nitty gritty. So look at the list of episodes, Maybe find a company that's similar to yours or same industry, listen to what they did, and you can learn a lot from that. So that's my plug there. Also, Y Cominator has just a really great library of content. Some of the Paul Graham essays he wrote, even the ones from 10 years ago, are still just amazing. Talking to customers, finding product, market fit, all that stuff. Got great videos too. Jason Calacanis puts out a pretty good podcast. It's very frequent, a lot of interviews with founders, but pretty interesting topics. Yeah, those are probably enough to get you started.

Speaker A: Okay, I love that and I, I love that you mentioned stuff that was written 10 years ago. 15 years. So I've been doing this for 25 years. I started my first company at 15. And so I've been doing this a long time. Right. I've, I've been through the dot com and then 2008 and then Covid and like building different startups at various different stages through all that. Right. But there is a lot of wisdom that doesn't change regardless of the circumstance or regardless of what's happening today. Right. And, and just not to beat a dead horse, but because I care about it so much, talking to customers, knowing your market really well and building relationships with people, that is 99% of building any kind of business, any kind of company. And so to your point, when you're reading something where they're talking about how to talk to customers, how to build relationships, how to talk to investors and build those relationships, that's evergreen. Evergreen, right.

Speaker B: Yeah, that doesn't go away. The tools you use to may change, but like that stuff is very fundamental.

Speaker A: Nathan, thank you so so much for taking the time with us today. Thank you for sharing your story. Thank you for building tools for people like us. Because you know, a friend of mine actually used your platform when she was doing her. Her seed raise of about. I think she did 900 and 150,000 of it came from 50 investor she found on founder suite. And so she has. Yeah, just I've heard great things. I loved when I started digging into it. We actually looked into using it before we decided that we weren't quite ready yet. So just thank you for building great tools. Thank you for listening to us entrepreneurs and caring about our journey. Thank you for being someone on the journey with us. And thank you so much for sharing your time and your energy and your story with me today.

Speaker B: Oh, thank you so much for having me. This was a really fun show and I feel like you and I could talk for another three hours.

Speaker A: Oh, we could.

Speaker B: And have fun with it.

Speaker A: Yeah, we totally could. So if people are interested in finding out more, getting in touch with you, following you, any of those kind of things, like, what's the best way for them to do that?

Speaker B: Check out FoundersUite. Www.f o u N-E-R-S-U-I-T e.com founders suite, or as my Polish people say, founders suit. They like to pronounce it like that. Check out foundersuite. Also blog.foundersuite.com, we have a lot of good stuff on there. Articles, interviews with founders, how to stuff about raising money. I would say connect with me on LinkedIn and maybe put a little note that you found me on the precursor podcast or something like that. Just so I kind of know who you are. Because we share a lot of really good stuff on LinkedIn. Like two or three times a week we put out, like, good articles, giveaways of like, here's a term sheet, here's some pitch decks, like, stuff like that. So a lot of really good stuff. I have a team helping me do that. It's not all me, to be awesome.

Speaker A: Uh, honest.

Speaker B: Yeah. Follow me. Follow me or connect with me on LinkedIn and then also Twitter. Just Twitter/founderSuite. And we're not quite as active there, but decent stuff.

Speaker A: Yeah. Funny how, because we have several Twitter accounts as well across my startups and we've just become less and less active and I don't know why. Like, it's weird, right?

Speaker B: I feel like you almost have to, like, the people who are in success on Twitter are like, like on there all day long.

Speaker A: Yeah.

Speaker B: And I don't know how they get their job done because they seem to be on Twitter. Right.

Speaker A: It's so true. It's so true. It's like you have three people who all they do is Twitter.

Speaker B: Yeah. But maybe that's your job. I don't know. I guess that works.

Speaker A: Yeah. Yeah. Maybe. Maybe we just create a new job. That'd be awesome. All right, thank you so much, sir, for being here. We really appreciate you and we appreciate everything that you do for this community.

Speaker B: Thanks, Cynthia. Appreciate it.

Speaker A: All right, y', all, thank you so much for joining us for this episode. I will be with you again soon, but in the meantime, as always, happy entrepreneuring and I will see y' all next time. Thank you for listening to this episode of the Startup Journey. If you have an idea for a startup and you want to explore the proven process of turning your idea into a viable business, check us out@precensa.com make sure to subscribe to this podcast wherever you listen to podcasts, so you never miss an episode. Until next time. Why do 85% of marketers swear by podcast advertising? Podcasts are booming and here are the top three reasons to hop on board with the Plug Podcast agency today. Reason 1 Targeted audience reach listeners who are genuinely interested in your niche. It's like having a room full of potential customers all ears. Reason 2 High Engagement Podcast listeners are loyal and attentive. Your message gets heard, not just skimmed. Reason 3 Authentic Connections Ads are seamlessly integrated by hosts, building trust and authenticity. It feels less like marketing and more like a recommendation from a friend. So, ready to amplify your brand's voice? Join the Plug Podcast Agency and start connecting with your audience in a whole new way. Hit that link and let's get started today.

Speaker B: Thank you for listening to this episode.

Speaker A: If you or your company are looking

Speaker B: to jump into the podcast world, now is the time. The Plug Agency is here to connect you to the full power of podcasting.

Speaker A: You just record and leave the rest to us.

Speaker B: The people are listening and want to hear from you. Theplug-agency.com that's theplugdash agency.com Click the link in the episode description for an exclusive offer.

More from Precursa

All episodes →
  • Entrepreneur Experience: Mark Van Holsbeck Founder of Jukebox Live
  • Entrepreneur Experience: Jack Nguyen, Founder of The Quick Company
  • Entrepreneur Experience: Andy Zurcher Co-Founder & CEO of Kidiosity
  • Entrepreneur Experience: Kelly Kiefer R.S.I.F. Advisors, Principal
  • Entrepreneur Experience: Carlos Gaitan, Co-Founder of Benchmark Labs
Explore the best B2B Startups & Founders podcasts →
All Precursa episodes →