171 - How this Founder Navigates Ownership - Chris Sacchinelli

Chris Sacchinelli: I typically land with trust the process, commit to the journey. I think you can control your process. You can't guarantee outcomes. And if you kind of put the pedestal or whatever, you know, however you want to frame it as, uh, or you benchmark yourself against the outcomes, then you're setting yourself up for failure. But if you benchmark yourself against your ability to control process and commit to it with consistency, then then you can hold yourself accountable to that. And for words of advice it would be don't compare yourself to others or others journeys. It's identify what it is that you want for yourself, identify what it is that's going to get you there, and then hold yourself accountable to doing that.

Nancy Nash: Our featured speaker today is the founder of uh, Bootstrapper AI, a platform designed to help founders measure ownership risk, strengthen equity durability and improve exit readiness. He's the author of two books, Ownable and Exit with Ownership, hosts the Bootstrapping to Billions podcast and puts out a newsletter called Simple Profits. In everything he does, he operates with the focus of helping founders transition from trapped operators into true owners. Chris, it's a great pleasure to have you joining us as our featured guest today. Thank you so much for taking this time to share your journey with us.

Chris Sacchinelli: Yeah, absolutely. Nancy, thank you for having us on the show and beautiful intro.

Nancy Nash: Well, I don't know if we included everything that you do, but we'll get there. So I was wondering if you could kind of kick us off telling us about some of your experience growing up, if there were any early life events or people that came into your life that you feel like have really shaped who you've become.

Chris Sacchinelli: Yeah, no, that's a fantastic question and something that we've gotten to a couple of times on the podcast in the past. And it wasn't intentional. It just came through conversation and speaking with some guests who had, had built and exited some businesses and in those moments of time and conversation and vulnerability, kind of shared why and what got them there and purpose driven. And for me it gave an opportunity to be reflective. And my, my story started early, like relatively early. And you hear it, you know, today and it's, you know, you kind of sit back and you, uh, it feels like this is like common space. But back in the day it was a little bit different. Before the interwebs, I just became really interested in this concept of investing early. I found out and learned about the concept of, uh, a stock early when I was in elementary school. And it just became fascinating to me that you could just own a company and I was like, what is that and how does that work? So I ended up walking to Edward Jones, which was a few neighborhoods over from me, and, and my dad at the time was an automotive teacher in Connecticut. He was actually the last industrial arts teacher in the state of Connecticut. I did that for like 35 years. And he had a passion for his students, pretty intense passion for his students, and he would try to get them exposure to a lot of different stuff. So a lot of the kids that came to his class were folks that weren't necessarily like super academic and they weren't doing great in school. And he kind of gave them a pathway to figure out that they could do other things and be good at other things and give them kind of like personal inspiration to do that. I still to this day have kids come up to me. Not kids anymore. They're grown, grown folks with families and successful businesses, quite literally like running multi million dollar plumbing companies. And they're like, your dad literally changed my life, like saved my life. If he didn't give me purpose, then I would have went and thought that I would have been nothing. And here they're successful. One of the things he did for his kids was invited somebody from Edward Jones into the class. Her name was Lori, and she taught about financial literacy. And I remember him talking about that. So when I learned about this concept of a stock, I walked over to that office and spoke to Lori and was like, I want to start investing. I was like 9 years old. And she looked at me and she was like, okay, let's figure this out. Which was cool because not a lot of people take time to invest in kids and take them serious. And I was dead serious because I had this kind of passion and purpose. And I was always a little bit nerdy about this concept of, I don't know, maybe it was watching too much Scrooge McDuck or something as a kid or whatever the case is. But I would have balled up little dollar bills in my closet and stuff, squirreling away money. And I was just, always was just really interested in the concept of it. I don't know why. Maybe there's something deeper there in terms of the security and stuff that it could bring and stuff like that. But, uh, she took me serious and she took out a piece of paper and she was like, okay, if you start investing now. And she took an 8 by 11 and she extended it and she was like, if you started investing now, by the time you're 30, you'll be a millionaire and you just have to put $50 away every couple of weeks. And I was like, sold. I'm gonna do that. But then I had to figure out how to get the money. And figuring out how to get the money for me at that point in time, it was, uh, fifth grade was, go get a job. And I ended up knocking on the door of my neighbors, and I pretty much was like, can I work for you? Does anybody have a job for me? And one of them actually said, yes. His name was Dan, and he ran an insurance business. And he was like, sure, come on in and start taking out the trash and shredding some papers, and I'll pay you every couple of weeks this $50 that you need. And sure enough, I did it. But he also saw something in me that other folks didn't. And I appreciate for him because literally probably put me on this path of entrepreneurship early on, changed my life. I would share ideas, and he would take them serious, too. And he would do a little bit of angel investing, which, you know, now, you know, but at that time, didn't. And he would, like, do little things with me. Like, we would buy domain names and we would bundle them with 1, 800 numbers and sell them to local businesses because he would had clients that were local business owners. And we were able to figure out ways to just kind of make money, which was crazy because it was empowering because, like, you could just do things. And then, you know, he figured out, like, he's. I think he bought like a. A locker of, um, like, you know, like where people store things and stuff like that. There's like a gumball. There's like, gumball machines inside of it. And we put that into, like, some of his local clients. And he would drive me around on the weekends and we would collect the coins. And one thing led to the next, and we ended up building a personalized baby album, um, company. And that was my first kind of real business. And it eventually.

Nancy Nash: How did. How did you come to that idea?

Chris Sacchinelli: Yeah, so honestly, I don't even know how we came to the idea. I think it was because we had found, like, the materials cheap online. We had bought a. Yeah, we had bought in one of the domains. And he was always looking at ebay and finding things that people were interested in buying and seeing where the market was. And we ended up, uh, conducting his

Nancy Nash: market research on ebay. Interesting.

Chris Sacchinelli: Yeah, so we ended up doing this thing and it became a business. And I would build these personalized baby albums in as, like, a middle schooler by hand assembly line. We'd Ship them out. And in the end that kept going. So we kept doing that and that stayed from middle school to high school and it ended up becoming my first exit. So before, before right around when I exited. Right, right around when I exited high school, we had sold the business and that then brought me to college. And in college I had the opportunity to kind of have some capital and I found this purpose and this interest that I, you know, was able to invest in and that was investing at the time. And that led to building successful young investor which was the first social network for young investors. And then I ended up scaling that up and we sold that before we exited college and then that brought me to Boston up in Cambridge and that's where we bootstrapped another business and then eventually exited that in 2012. But when I think about the reflection of uh, why and kind of like what caught me into that moment in time, which was a very opportunity in time to be able to. It was very developmental years and the effort to be able to put in and commit and grind through a lot of things the same moment. My mom was going through a battle with cancer. So she was diagnosed when I was very, when I was younger and quite literally that exact stretch she was diagnosed and they did not give her like a good outlook and they did not give her a long time, but she ended up surviving and she fought for 12 years when she was not supposed to be able to last that long. And when I look back and I reflect, I think a lot of the time in that moment in time in terms of putting so much commitment into the businesses and the entrepreneurial journey, it was trying to do something that on the outside I was getting positive praise and accolades for because these cool things were happening. Oh, you're building this social network. Oh, you're getting pressed for that and these positive things. But it was also something I could control and I feel like in hindsight it was me taking control of something in a moment in time where I felt like I didn't have any.

Nancy Nash: Mhm. That's a wise reflection.

Chris Sacchinelli: And to answer m your question, that was a very long witten answer to your question. Oh no, that's the real actual route.

Nancy Nash: Yeah. And I'm so sorry, you know, that that's something that you were facing as a kid. Unfortunately you actually had that in common with our co anchor Spencer, who's not here. But I also appreciate that like you took that opportunity, you know, to create something positive and find purpose in other areas too. But yeah, no kid should have to deal with Their parents going through cancer. So I am really sorry to hear that.

Chris Sacchinelli: Yeah, it was definitely a developmental force for sure. And it's been a while now. It's been a long time, 20 something years. So you try to reflect back on all these moments and you have these glimpses of memories, for sure, the things that plant in the mind. But yeah, without a doubt. I think that a lot of my journey started then. It started really young, at 9, because I had the opportunity, fortunate enough to learn what a stock was. And then my father reinforced it with his students. And then I found somebody who was willing to kind of, you know, humor me to a certain extent and put me on this path and gave me a purpose and a reason to actually go out and get a job and make money. And the person that I ended up connecting with saw something and was willing to invest and humor me again.

Nancy Nash: That's wonderful.

Chris Sacchinelli: And um, yeah, everything kind of happens and it's like one foot in front of the next. And throughout all that stuff. Yeah, life is a real thing, so it's not always going to be perfect.

Nancy Nash: No, but that makes a lot of sense. And I think I kind of know some of the answer to this question already based on what you've told us. But what led you to want to really get into the space of helping founders?

Chris Sacchinelli: Yeah, so to be perfectly honest, it was probably a chip on my shoulder because those three things happened. It was uh, an exit, which I didn't even really realize wasn't an actual exit. It was the social network, which I didn't know what a startup was. And then it was exiting from the business up in Cambridge. They were six, seven, eight figure bootstrap businesses. And all of these things were happening. And I was being told that I was successful and that all this stuff was good, but I didn't really actually feel it. And at that moment in time, like Silicon Valley and startups and building big tech businesses and Facebook and all this stuff was like a trend, it was an upward trend. And I was like not living that life. So I was doing, doing all these things. Young, really young, 20 something. And it's like everyone around me is like, oh, like you're like that. But I'm like, I don't feel like that. So after it happened, I came back home from Boston and we leased out a ton of space in my hometown. Cause I want to be closer to my mom. And it was like 35,000 square feet or something like that. Don't 100%, don't quote me to that, but it Was a lot of space. And we launched an accelerator program and the whole goal became, let's now invest in other companies, because that's what you're supposed to do. And if you're living this life and all of these things are true, then you need to do this next. And I started to literally, with my own money, invest in companies, feeling like that's what was going to give me the level of, you know, accolade or stamp of approval or, you know, you've been on this journey, so this is the right next thing to do. Hindsight, Hindsight, uh, not a great decision. So, you know, when you're running these programs and you're launching these things, especially, you know, the hubris of being young and ego and all this stuff. Like, a lot of the things that I did early in I feel like, were lucky. Like, I just found, like, I was in the right place at the right time, and something happened that was lucky. And then I just had the passion and grit and determination to stick to it. Like, for example, the business up in Boston. I was up in Boston for a totally different reason. I went up to Mass Challenge. So I had just exited with success wing investor. And I had a little bit of money, not a lot of money, but a little bit of money, enough money to do something next. And I went up because when I was in college, so I. I was like, um, entrepreneurial. I had to get folks to work with me without the ability to pay folks. And I was younger. I knew I was going to graduate college before I was gonna be 21. So I wanted to bars and stuff like that. So, like, while I was building success for your investor and building the team, I built this lifestyle card. And we worked with bars and clubs, and it was like a discount card for college kids. Pretty much like you showed the card. But I gave it to my team. And folks would sell these cards to make money on campus, and that's how we got distribution. But we would also use it to get into bars and stuff. You know, okay, I built that, and it was like a little side thing and it was profitable and I wanted to do something more with it. At that moment in time, Groupon was coming up. Like, that was the big next big thing, and there's something with trends there and all this stuff. I was like, oh, there's something to this card. I wonder if I could take this card and turn it into something. So when I went to Mass Challenge, it was like, instead of having a Groupon 8 by 11 and you're on a Date or something. You're taking out this piece of paper to go pay for the dinner and your date knows you're cheap. I was like, let's just put it on a card and then turn that into, uh, a lifestyle card. And that's what I went to Mass Challenge for. I was self funding, it bootstrapped. And I brought a bunch of my friends and stuff and buddies and we're living together. And on the t one day I was talking very loud because I was a excited young founder and somebody from Google had overheard me and they came up to me and took me aside. I was like, let's go get a coffee and essentially told me like, don't do this. We're working on something similar. Turns out that they were tied to the Mass Challenge program and in that direction brought me into a totally different business. And at that moment in time I had, um, a blog that was set up. It was a content syndication network. And again, I did it because we were trying to get into concerts and I was trying to make things fun for the kids that were working for me as like an extra benefit because I wasn't paying everybody. And it was like. So we had like this lifestyle blog going and it became this music network so kids would like. Frat rap was a big thing at that point in time. Like college campuses had little. Everyone had their own, um, little rappers and stuff and they would release their music with us. So we would get into concerts and they would drop their music on our site. And then we found that other sites started to copy our site and post our content because we were getting first releases. So we were like, let's just lean with it. So we started sending a newsletter and we would just do a roundup of the most popular things and send it out to all these other blogs and realize, okay, they would post it. The guy at Google essentially told me they were working on something else on the ad side of the network and they needed a guinea pig, like somebody who had a network but was willing to kind of take a little bit of a risk. And we ended up going in and we partnered and we ended up building a ad, uh, network. So we partnered to build a programmatic ad network and we built one of the first programmatic ad networks and we helped co develop one of the like, first holistic ad servers. So we were able to build out a programmatic ad network model that ended up scaling. So we went from like 30 million impressions a month to like 1.2 billion impressions a month, like really, really fast. And that became A very profitable thing. Happenstance though, because I was just, I happened to be on the T that day. I happen to speak speaking louder enough for somebody to overhear.

Nancy Nash: I mean, I'm part of it too though, right? Yeah. Wow.

Chris Sacchinelli: Uh-huh. So all of it. Yeah. At the end of the day, it just happens to be all the stars

Nancy Nash: align, but you are always, you are always working on something, you know, and I think that like, if you're going to be in the right place at the right time, you have to continually, you know, kind of be in the thick of it, which it sounds like you are, you hit on something kind of interesting. Talking about, I mean, several interesting things. But something that caught my ear was when you were talking about, you know, getting people on board with working for very little or no money. And I mean, that is like the crux of a successful nonprofit, but it's also like at the heart of a successful company culture. And it sounds like you figured out how to build that, that momentum, that motivation really early on, which is excellent. What do you think, reflectively, having done all these projects and companies are the elements of like a successful startup culture?

Chris Sacchinelli: Yeah, I think that culture, people, like a, uh, business is only good as the people that are involved with it. And culture is the heart of the business because it's what drives the people. And I just, I learned that really young because I had to, I just had no money. I bootstrapped everything. So like when I went to college, I knew I was paying for college myself and so I went to Tampa. And I went to Tampa because they paid me to go to Tampa. And like all of these things, happenstance just I kind of created and it was one foot in front of the next. And you know, you're trying to get folks involved and help you because you need the help. And if you're not able to pay them with one thing, you need to figure out another way to compensate them. And for us it was always, uh, for me it was always figuring that out. But, uh, you folks need to essentially have a purpose and believe in what they're doing. So money's a short term motivator for sure, it's important and you need to compensate fairly. But compensation is more than just money. It's everything. It's total comp, it's involvement, it's purpose, it's the ability to create, it's the ability to have freedom, make good, timely decisions. Ownership. And I think early in my career I didn't understand any of those things. It was a, uh, level of Necessity. And as I started to develop, so we did the startup accelerator that was like 2012 to 2015 and I was trying to help other businesses kind of repeat what I did, feeling like at that moment in time with ego that I could. Turns out I couldn't. Because I think again, luck happenstance, like just happened to be on the T, just happen to have these things happen and you have to be in the right place, right time and then the willingness to open to it, it's hard to replicate. So when we opened up the accelerator and we tried to build out the programs and invite folks in a very limited talent pool as well, which is not a great investment model either to have. Uh, and you're trying to like, with the hubris of like, all right, let's go repeat this success because that's what you're supposed to do once you're successful. Yeah, it turns out not great. Uh, but started learning things. And in that moment in time I realized kind of like, simple works. Like, simple is not easy, but simple definitely works. So that's when we started to lean into this concept of like simple profitable. And simple profitable led us from 2012 to 2015 to then launch Blue Collar Capital, which became the focus. So like in 2012 when we exited, we set up simple holdings, which became like a whole co model. So paid like a, uh, handful of folks a ton of money to give me some decent advice. And, and that's the byproduct of it, which became, you know, my whole, yeah, like, my moment of like Scrooge McDuck moment was, you know, coming to fruition because it's like now you got this baby Berkshire and you have a Hoko and you could do all these things and everything. So I was bought into it from that lens. But then you had to make it work. So I learned in this process, simple definitely works. Blue collar became the byproduct of just finding what was working locally and doing deals. And I found like some of these simple blue collar and probably back to the roots with my dad doing automotives and just like having a blue collar, kind of like a blue collar upbringing to a certain extent, realizing that these businesses were just good businesses and it was a lot easier to make those businesses work than something that was trying to chase the startup dream. I kind of had to have this realization and self check that, like, you know, it's not, it's what you feel like it's supposed to be because everyone's telling you, but at the end of the day you just gotta kind of do what's the right movements. So that's when we did blue, uh, collar. We shut down the first accelerator. And then hubris kicked in again. And I felt like there was gonna be something huge in terms of helping these small businesses because that's where I found solace, in a space and a sense of ownership and success again. Because we started to be successful with that portfolio doing just home service and real estate stuff, simple stuff. And I'm like, man, there's gotta be a way to bring technology to these like simple businesses. And I over complicated it again, like with hubris, I was like, oh, here's a moonshot opportunity. And I ended up pitching IBM and I was able to convince them because at that moment they were like marketing Watson. Like Watson was on Jeopardy. And they had like a Watson super bowl commercial and everything. So this is like 2015, 16. And I was like, man, there's something, there's gonna be something here. Like we're gonna bring AI to small business. So I pitched IBM and I ended up launching Connecticut's first AI accelerator program. And we converted a firehouse in Bridgeport, Connecticut, which Bridgeport is like a place in Connecticut a lot of folks don't wanna go. And we're like, no, there's a lot of opportunity there. Let' something cool. We converted a firehouse to an accelerator and we tried to open it up again. I tried to repeat the hubris of 2012 and do something big. And the goal was like, let's bring AI to small business. And as we were helping other folks build things, we were building ourselves and that became a economic development organization. I built helpgro ct and then that became Help Grow usa. And then we were trying to scale and we got to like 30,000 small business owners across the country. And the goal at that moment in time 10 years ago was like trying to educate that AI could help a small business, which at that point 10 years ago was a very hard thing to do.

Nancy Nash: Yes, you're climbing a big mountain.

Spencer Walker-Fooks: Yeah.

Chris Sacchinelli: So, you know, 10 years later, now we're on the other side of it with Bootstrapper AI. And what we're trying to do is help small businesses not just survive in this moment in time, but thrive. Because fundamentally, AI, uh, uh, is a very real thing. Back in 2016, it was kind of vaporware and things fell apart for us because it was vaporware. It was a lot more marketing and say than what it is today, which is just something that could be transformational and is going to be the case. I saw it then, which is Why I went all in on this accelerator and trying to build this footprint. It's just the tech wasn't where it needed to be. So where we are right now, though, it's definitely very much so the case. Like every business, everybody is going to be transformed and there's a knowledge transfer that needs to take place. There's a transfer of knowledge that's going to have to take place from the human into a protocol. And that protocol is going to need to be something that could be delegated to either human or AI. And I think every business period, if you want to survive, is going to have to ultimately do that. If you want to thrive, you want to do it well. And then there's a real reality that probably 6 to 9 million small businesses aren't going to survive. So then the other challenge that we're trying to figure out is what's the future of work like, what jobs will be created in this moment in time? And because it's farm to factory, and each of these moments in time you have, you know, web pages, yellow pages, the web pages, you have, you know, farm to, to factory. And every moment in time there is job creation. So for anybody who's going to be displaced, there's also new opportunity. And a lot of the work that we're trying to do today, 10 years into this game, because we've been fortunate enough to be working on this one problem for a very long time, we're trying to figure out what is the actual economic impact and shift in this AI, uh, economy to help businesses survive it and then also create new jobs within it. So that's a big portion of the work from a ownable perspective in 2020,

Nancy Nash: more like a business consultant type perspective.

Chris Sacchinelli: Um, well, so we're building. So with Bootstrapper AI, we're trying to build the protocol, we're trying to build the infrastructure to help that knowledge transfer take place. So we want to be able to help small businesses transfer the knowledge of the processes, proven profitable processes inside their business, into a protocol that can then be delegated to AI agents in the future or even today. Just people. And the reason why we got there and the way that we got There is in 2020 we started Bootstrapper Capital, which became our B2B service and B2B SaaS, uh, portfolio. So we've been doing. We started Blue Collar capital back in 2015, 2020, which was all home service and real estate. In 2020 was B2B service and SaaS with bootstrapper. And this is after being in the Journey now, uh, with the AI stuff for about five years. And we're looking at again, simple, profitable and how you could identify simple profitable models that work. Because in all of this experience, it complexity ultimately became degradation of success and outcomes for most of the things that we saw and the folks that survived and then ultimately built meaningful, profitable businesses were just simple. So we wanted to just focus on simplicity. That's why we ended up launching Simple Profits as the newsletter and we wanted to anchor it to that.

Nancy Nash: Gotcha.

Chris Sacchinelli: And we also kind of grew up in this moment in time because this is now 10 years from the exit and building the holding company. And in the holding company the goal became how do you just not just build something or buy something, but how do you maintain something? And a lot of what I became obsessive over for the past decade was building ownable assets. Something that my kids, I didn't have kids at the time, but now I do. And that's all I think about. Something that, you know, carries forward with legacy, something that's not going to degrade. And my belief system is that equity in a business naturally degrades over time. So either it's naturally degrading over time because you're building something that's too reliant on you. So we use Sally sue in our book as the example. My daughter drew the character Sally sue. Uh, this is audio, so I won't show it, but Sally sue runs Sally Sue's lemonade stand and Sally sue sells lemonade. And in the book we go through this journey with her and we break things down to five exits of ownership. So we think that every business is going to exit at some moment in time. Right. Whether it's an exit you want or an exit you don't want when you decide or you don't, everyone eventually exits, but we only talk about that final exit. The reality is it's like how you eat a cake one slice at a time. The first exit is exit your day job and make your business your job. Right? So it's like we're all going through exits at all moments in time and ah, a business shifts and transforms at each stage in terms of different things that it needs to accomplish. So when we're looking at a business, we're looking at an asset and we're looking at the equity of that asset. And what we believe is that the equity to grow grades, whether you're building something like Sally sue, who's maybe building a successful business because she's selling lemonade on Saturdays and she's making 100k. But if she doesn't show up, there's no money. So it's not a transferable asset. And then you have legacy business owners, like folks that have maybe, you know, family owned businesses that two, three year, uh, second, third generation successful businesses. They've been around for a long time. So you think that there's a lot of equitable value in them, but the reality is they haven't transformed and kept up with the times. And the transferability of that asset has degraded. So the equity is degraded. So equity is constantly degrading unless you take ownership of it, unless you're proactive into it. That's a big function of what we believe. So when we're looking at, uh, the market and we're looking at businesses and we're building the platform, what we're trying to essentially do is identify how we can help folks build assets that are durable and transferable. And because they're durable and transferable, they're valuable. And because they're valuable, anybody would want to buy them. But you probably will never want to sell because they're actually truly ownable businesses. They're ownable assets. All of that fundamentally is like the core of just, you know, commerce capitalism, the business.

Nancy Nash: Well, and also I can see that, you know, when you're selling your clients on that premise, like it makes so much sense for them to work with you. Um, can you take me into your books a little bit more? How did you decide on the content for your books? Because I'm thinking that you're putting out this, um, great newsletter a couple times a week. Did you decide that certain newsletters were just taking off and this really needs to become a book? But I just know the time, energy and money that goes into the bookmaking process is a lot more than, um, some of the other things that you're doing. How did you decide on the content?

Chris Sacchinelli: Yeah, so all of it started with just do for yourself and then do for others. So in 2012, we started the holding company and the function of the holding company became how do you accumulate assets worth, worth accumulating and how do you continue to own them? So the principle of just building an ownable business kind of became ingrained by the time we got to blue collar capital. It was fundamental. So I went through this lesson period, learning period of like four or five years doing the accelerator stuff to get to blue collar, making mistakes there. And by the time we got to blue collar, it was just doting, really simple, profitable businesses, ownable businesses. How do you maintain ownable assets, operational excellence within that. And these are just internal learnings. So this was just narrating out at this point in time. The newsletter really was actually a byproduct of kind of like a simple bet. It was an experience. So we identified or identified the trend of newsletters popping up. I thought that distribution was going to become very valuable as we were doing the Bootstrapper portfolio and we started launching Bootstrapper, which was more digital B2B service and SaaS side of things. And we looked at the market and we did a, uh, buy and build in public. So I went out and I acquired newsletters and we actually did that in our community that we were running at the time. And we identified newsletters to acquire. We then integrated them and we started running them. And we did that for like, I don't, uh, know, maybe three, six months, something of that nature. And what started as a simple bet, and I just wanted to see if you could do it and kind of, you know, do it for the audience, ended up becoming something I enjoyed. And I started to enjoy the cadence of accountability that was required to actually run the newsletter. And some three years later now we still keep doing it weekly and bi weekly because of the podcast. Uh, so yeah, it started as a simple bet. It quite literally started as a buy and build in public. And we took our audience along on that journey, acquiring newsletters, integrating newsletters, running the newsletter model, seeing if you could figure out distribution with it. And then eventually it just became something I enjoyed doing. Uh, the books and stuff, that's a function and a byproduct of having to put process in place to build the software. So we've been doing long term equity management as a firm for a long time. The core Bootstrapper Capital was long term equity management because we were doing it for ourselves, which is essentially just building an ownable asset, an asset that's going to continue to be durable, transferable and valuable. And when we're working with folks, it's just putting it on paper, makes it tangible and makes it real. And you're putting the processes in place and the frameworks. So it was more probably honestly doing it for myself and then doing it for others. And then eventually, uh, it became with the frameworks and that became the software. And by building the software, the goal became to do it at scale. And when we're looking at Bootstrapper AI right now, the platform, when you come in, you build an ownable operating system, you're running to a cadence of accountability. It's how we believe you Build an ownable business from doing it for, for 10 years and the goal becomes, you know, keeping it simple for sure, which is hard. It's easier said than done for sure. Simple works, but it's not easy. And getting it to a cadence. We wanted to create a reward system, a mechanism of incentivizing somebody. So if you run on the ownable operating system, every week you do a weekly retrospective. You're closing out your business. Most business owners don't. We kind of incentivize you to do it. And we incentivize with a valuation of the company. So once a week we kind of give a valuation of what the business could be worth and we show you through risk and readiness scores what it could be potentially worth. So that shows the wedge. That shows the difference of what the business is worth. Where it could be worth is the wedge, the wedge equity that could be built. And it kind of gives you uh, a big, a basic, simple framework to just keep it simple and focus and just do one next thing that can make the business worth more. And we just wanted to make it kind of like a game to build a durable ownable asset. And a function of valuable becomes transferable. The function of transferable becomes knowledge transfer, which is proven profitable processes. And most business owners don't want to do that type of work because it's like boring and painful and then nobody uses it. So we wanted to try to figure out how to make it fun. And then the reality is in this moment in time, in this age of AI, in this shift that's happening, we are going to become more agentic businesses. Everyone's going to eventually have to adopt it. So we're also trying to create kind of this capture moment in order to build a valuable business, regardless, it needs to be transferable. So uh, at its core, because you're looking at the other side of the market, we are business buyers as well, and we invest in businesses and all this stuff. So we kind of have a sense of what it takes to due diligence and acquire an asset and not a liability. So we took all that stuff and we built it in and we wanted to get somebody proactive into taking action. So we created this concept of a profit flow, which is just documentation of a proving profitable process in a business. And what we think is going to end up happening is moving forward, every business owner is going to have to transfer knowledge from their brain and they're going to have to put it into a protocol that can be managed agentically. And having worked on this for the past 10 years, we just know that there's two things that are gonna ultimately take place. One, AI is only gonna get better, for sure. But humans are humans, and there's a human function to all of this. And when you're delegating authority and delegating ownership and you're giving control of what you have to something else, there's an action that needs to take place. And whether in two years or five years from now, AI is gonna need a protocol or a framework to actually guide it. Maybe close out your books, for example, like a proven profit. A job to be done in your business, okay, may not need it. But the reality is, is for a business owner to actually transfer that authority and actually provide it, you're probably going to have to have a process. So in our software, what we created was a protocol where humans can transfer their knowledge into the software and then that can be delegated to another human so the jobs can get done, which is just building again, a transferable asset, regardless of AI or something that agentically can be followed and used. And where we think things are going to go in the future is if we do end up building agentic first companies, the job, the future job, it may not be bookkeeping, doing tasks like those jobs may go away in the 6 to 9 million that get displaced, but there's probably going to be a new job that's created in terms of like workforce management. And workforce management may become agentic workforce management. So the platform that we're building is built to support that. We also know, because we're plugged into the ecosystem and we've been building buying and selling companies for 10 years, that companies are only valuable if other people can buy them. And a function of buying a business is buying an asset and not a liability. And a function of buying an asset is the ability to buy an asset, which means that it needs to be fundable. And fundable means bankable. So it means capital ready. And I also think that there's going to be a problem in the future, like relatively soon, that when a bank or a financial institution or a financial partner or capital partner is coming in to help you underwrite a business to acquire it, which is a function of the work that we do. We help businesses transfer and transact is diligence into it. And we think that moving forward there's going to need to be a level of risk and diligence readiness for the ability to finance and fund a capital transaction of a business in the age of AI. So we also think that not only Is there the need for a protocol to transfer knowledge from a human to AI to then run a business and keep it simple? We also think that on the back end of it there's going to be a need for financial institutions to be able to underwrite and do real diligence on these assets. And there needs to be a protocol that can help facilitate that. Okay, so in our.

Nancy Nash: Is that, is that where you see your business going? Maybe in the next decade?

Chris Sacchinelli: Yeah. Like what we're building today is with Bootstrapper AI is you can come in and you can join a local chapter. So we're launching 500 small business chapters, kind of rinsing and repeating what we did with Help Care USA and we want to get to all 36.2 million small businesses. For sure you can run a chapter, you can get and launch your own os, your operating system, you can get your financial engine, your profit engine, your value engine, your people engine, which is probably gonna be a workforce engine up and running and you can unlock capital so you can get capital ready and then you can exit with ownership so you can exit through the marketplace. And we wanna have a full life cycle from start to finish of uh, building a business, starting a business to exiting a business, supporting the life cycle. And we wanna do it in a way that supports agentic first companies. Cause we think that that's gonna be. And we wanna do it in a way that can help businesses, especially small businesses, become agentic and, and support them. And that's why we're doing the local chapters. So like we think that people will ultimately need to do it. If we think about yellow pages to web pages, it was like AOL sending CDs, physical CDs and it's like getting folks online with iPhone. It was like Apple in the app store, you know, hosting workshops. Physically we think that with AI it's going to be probably a function of some level of boots on ground people supporting small businesses. Because it's a very scary thing. And we know this because 10 years ago we did this at scale and we had the feedback of trying to introduce this concept of AI to small businesses then. So we have a little bit of experience into it right now. We think that it's going to be a very scary thing for most small businesses. We think that there's going to be a level of local community support. There's likely going to be local community heroes that help facilitate it. So we want our chapter to be potentially that and it's going to be simple. Like we just want to help Folks transfer a that knowledge, it's going to build a more durable, transferable, valuable asset regardless. So it's the right things to do regardless. And if you can do the right things in a way that also supports the future, which would be the adoption of agents and the ability to then support a workforce that could maybe manage your agentic workforce for you. Like, you know, not everybody learned how to build websites. There was a job that was created. So we think we can create jobs for folks that are maybe going to lose jobs because the transactional work is going to be lost, I think.

Nancy Nash: I mean that's a huge, uh. Yeah, that's a huge value add. Uh, that's a huge honestly question that keeps coming up in our discussions with people across industries. So I really appreciate that you're thinking about that and I definitely think there's a future for your company in that space. When I was looking at your website, I really liked, you know, what you had to say about the founder fellowship aspect of the business. And it does stand out to me as kind of like unique in this space and a real kind of value add as entrepreneurship is quite lonely for a lot of people. Can you talk about how that works a little bit?

Chris Sacchinelli: Yeah, entrepreneurship can be lonely, especially for bootstrappers. Most bootstrappers are smaller than five teams on average. Most business owners on average are solopreneurs. So by definition it is a lonely thing. And since COVID a lot of folks have gone remote and that's become more of a thing, so even more lonely and siloed. And the reality is life is a real thing and not everything's easy, not everything's perfect. Even though you go on social media and stuff and everything looks good and simple and works and great reality is most of it's very hard. That's why I wanted to lead with the story with like luck, you know, a lot of the things that we're fortunate enough to be able to do with like luck and a lot of it came from like very real hardship type moments. And just like it is just what it is. Like things don't just tend to work out. You just have to kind of keep going at it. But you know, it's not easy and it's not perfect. And for, you know, the sad truth is because it's not great most of the time if you're alone or you're building a business, oftentimes don't want to share the bad things. So like that's even more isolating. And it's like if I don't feel comfortable sharing what's actually going on. I'm not going to say anything at all because I don't think that it's good enough or things aren't perfect or whatever the case. And then folks don't actually get help and things just stay the same or get worse, which is degradation of equity.

Nancy Nash: Yeah, absolutely. I think it was, you know, what you keep saying about luck? I'm pretty sure it was in uh, Mark Cuban's book, the uh, one and only business book he ever wrote where he was saying, you just keep working at it. You keep working at it, keep working at it. So that um, someday someone can say, hey, look at this overnight success over here. You know, like that you're just, you are in the right place at the right time because you've continued to seek those opportunities. So I do think like you're very hard worker and that is why, you know, you've had been in the right place at the right time.

Chris Sacchinelli: Yeah, like I think we're absolutely going to change the landscape for small business. The Bootstrapper AI or some variation of it, it may not be that, but I think it's the brand because the name is in the, the like the ICP is in the name. It's a dictionary level word to be a booster.

Nancy Nash: It's also something that you clearly deeply want. You've tried it in a couple different forms, right?

Chris Sacchinelli: Mhm.

Nancy Nash: That drive is very deep in you. I think that that's so important too because one of the things I wanted to ask you about was, um, how you feel about serial entrepreneurs that have no emotional attachment to any of their projects. Because clearly you have such an emotional attachment to this.

Chris Sacchinelli: Yeah, no, this is like quite literally it's a continuation because yeah, it takes 10 years. Like everything. Even if you have a simple profitable business and it's a painting business and you're painting a wall the same way every day for 10 years. Like it takes time to just have things mature. Like so we have different levels of the surface of our portfolio. We have like very basic businesses that we get to see every day. And then we have like the moonshot at the tip, the spear, something like Bootstrapper AI. Bootstrapper AI. I mean, yeah, it's the second, quite literally, like we went really big 10 years ago to do this and we learned a ton from it falling on our face. And there's just a real need at the end of the day so we have the opportunity. We're fortunate enough to be able to go back at it and Figure it out and do the blocking and tackling the right way. But yeah, nothing's easy, right? It's absolutely not. And then to figure out the right pieces, the simplest pieces to put together and then put them together in the right possible way. Like you could have all the blocks in a kit, but if you just start trying to mash them together, you're not going to build the thing on the front, on the front cover. You're just going to have a mess. Even though you have all the parts, some people don't have all the parts, right. So you just have to kind of think about it from a disconnect of passion and purpose and then just trying to figure out a productized thing. It depends on the type of entrepreneur and what you want to do, right? So if you're trying to build something for capital, cash flow money, then there's different ways to build businesses. Like you can absolutely just identify a need in a market and fix that need, fill that need, right? Like business is super dead simple at its core. If you're trying to just legitimately do something to build a nice lifestyle, bootstrap business or uh, just you know, uh, something to, to make money, it's dead simple to make money. It's find a problem, validate the problem, sell it, make it, exit it. It like sell it, make sure people want to buy it, then invest in making it right, which is the heaviest possible part. And then exit it is like, don't, I'm not saying exit, like sell it again, it's like exit, get to the next exit. Exit. It could be like delegate it to somebody else, right? Put systems, processes in place to be able to keep it simple, right? Get to operational exit. So it depends on your goal. And if your goal is like, let me validate the fact that I can build a business and make money with my business, that could be disconnected. You're just finding a problem in the market and you're serving that problem. But what you're end up going to find is like, yeah, everything takes time. You're going to need to invest at least 5 years, 10 years especially to build something that's maybe sellable. Like that's changing slightly right now. Like folks are definitely exiting faster but like you're going to assume like you're on a five year journey at least it should be five to ten years before something matures. And you know, unless you, you know, just doing it for the sake of doing it, but to do it to get to somewhere and whether that somewhere is like an operational exit or it's an exit to somebody else, or it's just something to keep going and doing, you're going to eventually get bored. So if you're doing like businesses that work are super boring because you're just doing the same things over and over and over and over and over and over and again once you figure out what works. So like that's repetition, that's super boring. A lot of folks like, especially now it's like we want shiny object and all that stuff. Like that's how you break businesses, especially profitable businesses. So it's like if you're just going after that, to fall in love with

Nancy Nash: the process as they say.

Spencer Walker-Fooks: Mhm.

Chris Sacchinelli: Yeah. Which is so hard. It's so hard to do. That's why realistically getting to an operational exit is probably the best thing somebody could do fast. Because getting to an operational exit allows you to get out of the risk of that, of the bore, the boring, which gets you to potentially the point of sustainability, durability, transferability, value.

Spencer Walker-Fooks: Right.

Chris Sacchinelli: But yeah, finding something that you're passionate about and that you have purpose towards, that's a privilege. I think like, I think like you have to because it's hard. It's also, it's harder to do that because you have to make decisions that aren't necessarily like the lowest common denominator of let's make money.

Nancy Nash: Sure.

Chris Sacchinelli: You know, and that's hard to build a business like that. It's definitely hard to bootstrap. That's probably why most businesses are VC backed that go that route. I've never done that, so I don't, I don't have that lens.

Nancy Nash: Sure. I mean, I appreciate though like that you have so much bootstrapping experience. Like, you know, uh, when I first read your profile I was like, why? You know, my first question is, you know, why do people come to this person for advice? But understanding your journey, I completely understand like how you are such a good fit for your business, if that makes sense. Thanks. We're close to the end of the hour, but I do have two more questions I wanna get to if that's okay with you.

Chris Sacchinelli: Yeah.

Nancy Nash: How do you define success for yourself at this point in your journey and is that kind of one in the same personally and professionally, or do you think it's different?

Chris Sacchinelli: How do I define success for myself at this point in the journey? I think that I define success for myself based off of. Oh, that's a good question. So I, I find I define success for myself. Honest answer. I define success for myself based off the goals in which I actually set and then achieve. So I do define success and hold myself to that level of standard of setting a goal out and then figuring goal out and achieving that goal. But on a broader sense, I would like to say that I define success based off of lifestyle balance and the freedom to decide and have flexibility and not necessarily be obsessive over one thing, but find balance, balance in all things. Specifically with my, my kiddos, with my children. Like I, I essentially five years ago made a decision to take a complete hiatus for the most part and step back. And that's probably the evolution of Bootstrapper Capital because I was trying to find the simplest possible deals to do and essentially a model that would create flexibility for time with my kids. And I also now see this moment in time and that's the kind of the precipice for Bootstrapper AI. I'm like, I also don't want my kids to look at me in 10 years and be like, dad, you were there, you saw this happened. Why didn't you at least take a shot? And that's been hard. It's been kind of hard to get off the sidelines and get back into it. It's taken me about 18 months or so to just get to the point where we are right now, to really push hard again. But yeah, I would define success. I think it's essentially your ability to set goals, create simple bets around it, and then keep consistent to it. So having discipline within the framework of the experiment, I think that some folks, I think for me, success is defining the experiment and then accepting when the experiment doesn't work and knowing to shut it down versus identifying when it does work and going and doubling down.

Spencer Walker-Fooks: Mhm.

Chris Sacchinelli: I think the ability to set goals and then achieve it in that type of framework is the definition of doing it successfully in a broader sense. I definitely think that it's the ability to invest time with the, you know, the right level of balance. Yeah, I think achieving freedom to decide is a very powerful thing that's very well said.

Nancy Nash: Achieving the freedom to decide. And along those lines, we like to end our interviews by asking you what words of wisdom you'd like to leave with our audience today.

Chris Sacchinelli: I think the words of wisdom to leave are probably best suited for themselves to decide. I typically land with trust the process, commit to the journey. I think you can control your process. You can't guarantee outcomes. And if you kind of put the pedestal or whatever, however you want to frame it as, or you benchmark yourself against the outcomes, then you're setting yourself up for failure. But if you benchmark yourself against your ability to control process and commit to it with consistency, then you can hold yourself accountable to that. And for words of advice it would be don't compare yourself to others or others journeys. It's identify what it is that you want for yourself, identify what it is that's gonna get you there, and then hold yourself accountable to doing that. And that's what I mean when I say trust the process, commit to the journey.

Nancy Nash: Wonderful. Thank you so much. I feel like you've given us so much today. I really appreciate your time and the energy that you put into this interview. Um, if people want to learn more about what you do, if they want to, um, buy your books, how should they go about that? How would you like them to contact you?

Chris Sacchinelli: Yeah, the absolute best place would be bootstrapper AI and signing up and joining a local chapter. It's 100% free to find and join a local chapter. The goal of the chapter is to just essentially a created a community where there's local folks boots on ground. We create paint by numbers boot camps that we provide to each community once a month. And the goal of the boot camp is to get to your next operational exit. It and eventually over time, we're hoping that operational exit is the ability to again, just get yourself out of a job, which means being able to delegate to somebody else. And right now it's human. So keep it simple. But the reality is probably going to be in the future AI. So skate to where the puck's going to be and meet people where they are. So join a chapter, get to an operational exit. We try to make it dead simple and then hopefully from there, trust the process, commit to the journey.

Nancy Nash: Wonderful. Well, thank you so much again, Chris. We wish you well in your journey. And Spencer and I and the team behind Founders Voyage feel really fortunate to be part of this community with you and with the others that joined us today and to bring you cooperative learning experiences. This like this one each week. Um, we do invite your nominations for future interview guests if you do know someone else you think would benefit from this experience. And in the meantime, you can listen to, uh, our edited podcast under Founders Voyage on your favorite podcast platform or directly on our website, founders voyage.org so thank you so much again, Chris, and we look forward to staying in touch with you and continuing to hear about your journey.

Chris Sacchinelli: Nancy, thank you for having me.

Nancy Nash: All right, take care. Have a great weekend ahead.

Spencer Walker-Fooks: M. You've just finished another episode of Founders Voyage. The podcast for Entrepreneurs by entrepreneurs. The team at Founders Voyage wants to thank you from the bottom of our hearts. We hope you enjoyed your time with us and if so, please share this with someone else who might enjoy this podcast. You can also support us by leaving a review on Apple Podcasts and Spotify, and by donating to our Patreon Patreon Outro Music Today is Something for Nothing by Reverend Peyton's Big Damn Band.