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A
Foreign. Hey, this is Keith with Liftoff. I have a really fun, exciting guest for you today. I mean, look, this is all talk about the startup ecosystem. We're talking about founders. And one thing we know is founders know how to start. Fewer know how to scale, almost none know how to finish. Today's guest did build a global economy company to 200 employees, 12 countries, and sold it for a nice chunk of change. I think it was like $4 billion to a competitor. He also competed in 17 Ironman triathlons and summited Everest. So is that not a goal oriented, heat seeking startup founder leader? Yep. Stephen Pipnick, my guest today doesn't separate endurance from leadership. He builds companies the way he climbs mountains. Intentionally successful, systematically, and with the finish line in mind. The startup journey is about discipline and exits and what it takes to finish strong. Stephen Pivnick, welcome to the Liftoff.
B
Keith, thank you so much for having me. I, I love that introduction. That's fantastic. Thank you.
A
I, I like your story, man. It's, it's sort of analogous. I kept thinking, look, my show's called Liftoff. It's the startup journey. We love talking about what it takes to be a founder. And, and the, the comparison to climbing Everest or running triathlons is, is a good representation, is it not?
B
Oh, absolutely. I mean, I, I'm a firm believer that entrepreneurship is an endurance sport. And endurance sports just have so many similarities to entrepreneurship. And I'm, I'm happy to share all of them and go into details.
A
Well, let's go into some details. What started first, the athlete or the entrepreneur?
B
The entrepreneur started first, for sure. I got bitten by the entrepreneurial bug early on because I, I think I inherited it from my father. And then my midlife crisis. When I turned 40 is when I picked up endurance sports and became addicted to those.
A
Wow, you picked an interesting time to go pick up 40s of my, my knees started to, to, to crack.
B
No, I'm just living proof that it's never too late. Yeah, I mean, I do. I wish I hadn't started endurance sports earlier, of course. I mean, I would have been much more competitive than I am now, meaning I would have placed higher. But I, I don't, I don't care. I enjoyed the preparation for these events and I enjoy participating in these events, and my finishing time and place don't matter.
A
Awesome. I love that approach as well. Now, of course, entrepreneurship, it does matter how we finish. And you had an excellent finish. Give us a little bit of the backstory.
B
Sure. So, yeah, it's Funny, I just, I actually wrote a book called Built to Finish. So the entire story is available in my book. But the backstory is I started a computer consulting company back in the early 90s. This is when there was a huge need for application development expertise. Just like we all have apps on our, on our phones right now. Well, back in the day there weren't applications that companies could buy. If a business needed to automate a business process, they would hire consultants like us to, to write these applications from scratch for them. So we started writing applications. An application that we wrote which was really, really niche and unique for a large bank, turned into a line of software products for us. And then we ballooned that little custom application development project into a suite of software products and we became an internationally well known software company like you mentioned, which we expanded to have employees in 12 states, service, you know, many, I'm sorry, 12 countries, 35 states in the U.S. and service the 90% of the global 5,000 customer base.
A
Wow. So a lot of this was I'm going to build and build to last. But did you have a exit in mind? Did you have a thought about how you were going to finish?
B
I wish, I wish I was, I was a smart then as I am now and a lot of advice I love to give is, you know, build now with the end in mind. I definitely did not build with the end in mind. I build because I built because I thought it would be a better career choice for me, it would be more beneficial for me financially and for me and my family. And I just, I felt that we can make a difference in the markets that we served.
A
So with, with that comment, it leads me to think, well, what if you were to start it today? How much of it would you build with the end in mind versus just recommending, hey, build to do the best you can each day, each month, each quarter.
B
Yeah, there's nothing wrong with it with, with the latter of what you just said. You know, we call them, you know, lifestyle companies. There's absolutely nothing wrong with building without an end in mind. You know, just building to, you know, service customers have an impact, you know, to, to the marketplace and to run it for years. And if not gener, that's definitely a strategy or you can build it with the end in mind and know exactly, you know, what revenue size you want to get to, who your potential acquirers are, whether they be strategic or financial in the future and do all the necessary things from the very get go in order to maximize that, that exit at the end.
A
Yeah, Beautiful. Okay, so you've scaled to 200 employees, 12 countries. What breaks first in companies that scale fast?
B
Oh, my God. People break first. And you quickly outgrow the individuals that you've started with, and eventually you'll outgrow yourself, which definitely happened to me. It took me a long time to realize that there's somebody that I'm better served, that my business is better served by having a professional CEO run it. I'm not taking any credit away from what I built and the progress that me and the company made. But there came a time, and for me, it took forever because I was really young by the time the company was about 24. 20. Yeah, about 23, 24 years old. I said, you know what, to my answer earlier. I'm breaking and this company is going to be better served.
A
Your realization or your partner's realization, or did your company shake you up one day and say, hey,
B
I had brought on a group of advisors called Acrisis, and their recommendation to me, part of, you know, many recommendations was to look at the executive team and to make sure I was surrounded by the right people on my senior leadership team. Right. So we, we went through individuals almost on a run, a roll by roll basis. And we, you know, some people, we, we were able to, you know, to move around the company, you know, others we had to, you know, part ways with and bring on some, you know, professional leadership in that specific area. That's inevitable. That's going to happen on everybody's journey. And during that process, I finally looked in the mirror and I said, well, if I did, if I did, if I felt that I needed a, a different talent in this specific role, maybe I should, I, I can, I should consider going through that process with me personally. And I did.
A
That's modest of you. Now look, I mean, founders are, can be brittle. As tough as they are on the outside, they can be brittle on the inside. I find there's a way they can sabotage themselves.
B
Yes.
A
And, and during scale. Right. So there's emotional issues, there's business issues. How do you, how do you find that?
B
Yeah, I mean, I think a lot of founders, myself included, are really, their identity is wrapped up in their business. Right. They can't, they can, they really can't separate their identity from being the leader of what, and the founder and the CEO of what they started. And that's fine. And, but I'm saying. And there's some limits to that. Not in all, there's, there's plenty of examples where a founder has taken a Company from zero knowing as little as I did when I started mine to over $100 million, if not $1 billion in revenue. That can definitely happen. But when you realize that the company, there's a possibility for the company to be in better hands, that's something that's, you know, worth pursuing. And if you find the right person, then you go down that route or you can, you may come to the realization, you know what, I tried. I'm still the best person to run this company. And that's great too.
A
These personnel challenges are never ending. What's, what's the Ironman equivalent to scaling a company, Stephen?
B
The Ironman equivalent, I guess getting to the world championship, right, because it's a, first of all, an Ironman race in and of itself is an incredibly, incredibly complex endeavor to go after. It's a ridiculously long distance of swimming, biking and running, um, 2.4 mile swim, 112 mile bike, followed by a full blown marathon with a 17 hour, you know, cutoff to do all those three things. Right. So there's planning, there's preparation, there's execution, there's pivots during a race, there's setbacks during a race. And all of those things that I just mentioned are, are, are, are elements of entrepreneurship as well. You know, you need to plan, you need to prepare, you need to pivot, you need to deal with setbacks. There's going to be times where you're banging your head against the wall and you're going to want to quit. I've had that moment in both sports and in running my company. And that's why I love comparing the two because they feed on each other.
A
Right. What's, what's the equivalent to finishing strong in business and in, you know, maybe your personal example.
B
Yeah, I mean, finishing strong in business is finally, you know, realizing the value of what you created. I mean, a lot of entrepreneurs put in a ton of blood, sweat and tears into their business and they find themselves, you know, in 10 years or in 15 years that they have 90% if not 100% of their net worth tied up in this illiquid asset called their company. Right. So finishing strong, in my opinion, is finally realizing that you want your family, yourself and the stakeholders in the company to benefit from all these hard years of effort via a strategic exit or an investor majority recapitalization. So obviously in a race you want to get to the finish line if you have a certain, you know, place in mind, you want to be on the podium first, second or third. Great. Go for that, or sometimes, like in my case, I just want to finish because I, I do these events just so I can participate, stay super, super healthy and train to get there, finish strong so that I can walk home without being, you know, carried in a wheelchair, which happens to some.
A
Yeah, so what, I mean, this is kind of an interesting thought we, we're discussing here. When's the right time to think about an exit? Now I'm going at it from the standpoint of, okay, I'm done with this, to two, I have people knocking on my door offering me insane amounts of, of money that gives me, you know, generational wealth. Or three, man, it's all crumbling down. I got to get out of here
B
before it all falls off on me.
A
And all of those scenarios can be true. I'm not sure they can be true at the same time. Maybe they can. But what are your thoughts about when's the right time to be thinking about these things?
B
Yeah, the right time is different for everybody. And obviously there's a huge financial component which I'm a strong believer in, that needs to be evaluated many, many times. And we can pick a time frame in the business. You know, a five year mark is a good time to start. You know, definitely by the 10 year where you need to find, kind of realize from a financial perspective, what is the right number for me personally? Right? I mean, everybody wants that unicorn $1 billion valuation, but very few people are going to get that. But the right number is easy to calculate and there's multiple methodologies to utilize. Like in my case, I said, you know what, if I can sustain the lifestyle that I have right now after 26 years of running my business, I, then I'll be, I'll be happy. So we went through, we, we went through this calculation. It's called a proceeds waterfall. It's a, it's a pretty sophisticated spreadsheet where you start at the end, right? How much money do I need after everybody's paid? All the equity holders, all the stock option holders, the lawyers, accountants, Uncle Sam, state and local taxes, et cetera, et cetera, et cetera. What's that bottom line number that I need, if invested conservatively, without a significant amount of risk, that'll throw off enough cash flow for me to have my current lifestyle. So then you work your way back, you work your way backwards from that. So to get that number, what does my enterprise value or sales price need to be? And then, then you, then you talk with investment bankers and you figure out, well, is my company, you know, worth that Money today or is there a gap and then you put together a plan on how to, you know, on how to fill that gap.
A
How did anything shock you during that process? The exiting process?
B
Oh my God. There was a lot of surprises. The amount of taxes that needed to be paid surprise me. One of my biggest advice to entrepreneurs that are building companies right now is to start tax planning and estate planning way ahead of the exit. If you think, you know, my exit is not. Not till five years from now. Five years will go by in a blink. And there's a lot of tax strategies that you could put into place that are necessary to be put in way ahead of the actual exit event.
A
Yeah. And just to double click on that, Stephen, give me an example because I know when because I've started a few myself. You know, there are times you want to take your options and pay for them early. What are some of the things that you found is as just helpful to hints.
B
Sure. There's a lot of, you know, QSB stock, QSB type of offerings are available. Moving shares of your company into much more tax friendlier states from the state that you may be incorporated in. You know, those are all processes that can be done and are 100% legal
A
as long as starting a trust is another option.
B
Starting trust and putting shares of your company, you know, in that trust. But again these are very important to do way ahead of the transaction because if it's too close to the transaction, you will be audited and everything that you've saved you will pay back with penalties.
A
Oh my gosh. There's some stuff going on. Right.
B
And, and yeah. And there's no downside to doing these things. Even if you're, you're doing this. These stra. Tax strategies for an exit in the future, if that exit never occurs, there's, there's no harm in doing a lot of these things. Why?
A
What's the sound of an exit anyways? Kidding aside, you went through a lot in terms of building a business and ultimately selling a business. Did you have any post exit regrets? Like I really wish I didn't sell it at that price or I wish I left earlier. I should. I mean what was your major like realization? And maybe it wasn't even specific, maybe just general.
B
It was interesting. My best friend and I, we, we have a lot of things in common and one of the many things that we agree on and he sold multiple businesses as well. We, we could have dreamed the bigger right. We, we and there's. We're very proud of the level that we Got our companies to. And the transactions that happened, the. The exits per se. But we look at ourselves like, you know what, we could have gone bigger
A
instead of getting a little bit more about that. Stephen, what do you mean by that?
B
Just from a pure revenue perspective. Right. In my specific case, we. We grew to again, from nothing, totally bootstrapped without any outside investment to over $40 million in sales. And looking back at it, I'm like, you know, what if I put. And I put together a strategy to exit on my terms, which I can get into. I wanted to make sure that I wasn't part of the deal. A lot of founders want to continue working with their company post exit. In my case, it was. It was just time.
A
Right.
B
It was 26 years.
A
You made most of the right decision. Dreaming bigger is what I didn't expect to hear.
B
Yeah. So we, looking back at it, you know, could have gone bigger, you know, could have done a lot of things from a product side, from a development side.
A
What does that say? So I've got a couple of founders listening to this. They're in that early stage. Maybe 5 million in ARR. Maybe 10. What are the things they need to be thinking about short term, maybe a little bit with long term besides what we've spoken about.
B
Yeah. I mean you really have to weigh the risk. Right. So. And the risk of, you know, going bigger versus taking chips off table today. And you know, sometimes you can do both if you really want to accomplish both. There's definitely a strategy to be put in place where you can take a lot, as many chips as you want off the table. You can find the private financial partner and let's say a private equity firm that can either do a minority recapitalization or a majority recapitalization, allowing you to take chips off the table to there kind of de. Risking this value that you've built. And then you, you get to go along for the proverbial second and third bite of the apple when that, when the comp. When the newly formed company, now private equity backed, you know, continues to grow. So if you want to take 100% of the chips off the table. No, nothing wrong with that. Or you can take a partial chips off the table.
A
I've been involved in a few deals where private shares have become more liquid through different types of transactions. Secondary. Right. Secondary market.
B
Right.
A
And other opportunities. I think that's spreading besides the CEO level or the board level or the C level on down. I think that's healthy. Do you agree?
B
Definitely. I mean any form of Liquidity is definitely a good thing and it helps everybody involved, especially the folks that are participating in the day to day grind. If there's a way for them to achieve some sort of liquidity before that final change of control occurs. I'm, I'm all for that. And I agree with you. I'm seeing a lot more of that these days.
A
I mean, I can buy stock in anything. Except some of them have a pretty high minimum for that. Not everyone's going to enjoy. Hey Steven, so you're involved in a lot of exit consulting and some other work. Tell us, what else are you up to today?
B
A lot of exit consulting, you know, working with a lot of entrepreneurs that really don't understand if they're ready or not or if their company is ready or not for a maximum that exit from a valuation perspective. I really, you know, I've had my eyes opened when I was going through the process as far as what the valuation killers are. And it's really rewarding for me to help open an entrepreneur's eyes into, you know, what some of the possible valuations, valuation killers are for individuals. So I work with founders in that capacity. And I'm also really, as we mentioned, I'm huge in endurance sports and building an endurance mindset. So I like to take founders on retreats, whether they be, you know, mountain based with no, no prior experience necessary, just, you know, entry level mountaineering where they get to learn some of the concepts of, you know, high altitude climbing or triathlon training, which, you know, I, I love to do both. So I, I, I, I, I, I love to, you know, share the knowledge of both of those types of endeavors and then relate that back to their business. And again, the planning, the preparation and execution that's involved in all of the above to help them get to wherever they want to bring their company next for, for the next chapter.
A
Fantastic. Steven, tell me, as you're meeting with these founders, with these CEOs, what's the thing that you're most interested in, like interviewing for and not really to hire, but to say this is somebody who I really think would get it and then what is it that you don't think is that important?
B
Yeah, I mean, I really like and this is a really tough subject to cover with a lot of founders. You know, we're incredibly loyal to folks that have started with us. So I like to have, you know, sacred cow conversations early on around, you know, leadership team and other folks within the organization because unfortunately a lot of again, and this is for a little, a little Bit past the starting line. When you're talking about maybe like the 5 to 10, 10 year time frame. There's folks that have been, you know, in positions from the get go that really aren't, aren't the best suited, you know, to be in those positions moving forward. So those are really hard conversations to get to have and to get buy in from. But oh my God, does action against this topic actually move the needle? When you get the right professional head of sales, when you get the right professional CFO in place, when you get the right head of product development or you know, customer service in place, these things, you know, move, move the needle tremendously.
A
Okay, I'm going to bounce over to the lightning round to kind of amplify some of the questions I've asked you, but also just keep it kind of on the short answer time because you know, we joked around our ADD society today. Anyways, people like sure quick answers. But for you, talent or discipline?
B
Discipline.
A
Yeah, I think so. It's becoming more common, right, to have the tap.
B
Absolutely.
A
Grow fast or grow right.
B
Grow, grow right. Nine times out of 10. Times out of 10.
A
I'll leave that one up. Everest or Exit?
B
Since I've already exited, I want to do Everest again was a whole nother story.
A
We'll talk about that on our next chat. What's harder? Mile 20 or finishing due diligence?
B
Oh boy. Holy cow. The diligence process will be the most complex and nerve wracking and stressful situation you'll ever find yourself in. So that's I and I've been through many, many mile 20s. Due diligence is harder.
A
Um, you've got a great book built to finish. What's the other bookend that you would recommend every founder read?
B
I'm reading a book right now which I really love. It's called Turning Pro and it has nothing to, nothing to do with, you know, being professional at any given sport, but it's just about, you know, leveling up your performance in whatever you may be participating in currently. I really, really love it. Turning Pro.
A
All right. I like it. Give me one other one because I know you're a big reader then.
B
One of my favorites to recommend is the One Thing. It's one of my favorite books and I'll summarize it really quickly. What is the one thing that you can do that'll make everything else either unnecessary or significantly easier? And you can apply that question to anything. Hey, I'm trying to expand into Europe. I'm trying to grow this product line. I'M trying to, you know, increase my profitability. What is the one thing that you can do that'll make everything else unnecessary or a lot easier?
A
It's also a great line in City Slickers from Billy Crystal and.
B
Oh, is it?
A
Come on. You don't remember that line? I.
B
You know what? I can't believe I've only seen that movie one time. I need to put that on.
A
You're a Long Islander. Come on, you. Okay, so even cheat a little bit. Go to YouTube. City slickers. I think it was Jack Palance, the famous actor, who gave the line to Billy Crystal. The one thing. And I'll read the book.
B
Oh, that's fantastic. Now that I know, hey, I'm definitely gonna go watch this, and then I'm gonna play. I'm gonna play this for a lot of people.
A
You're gonna love it. Okay, so listen, most founders build to grow the elite build to finish. Discipline isn't sexy. Systems aren't flashy. Endurance wins in sports and business. That's my way of saying, stephen, thank you for showing us how to build companies and lives that finish strong.
B
Thank you, Keith. You summarized it perfectly. Amen.
A
Amen. Great tab.
Date: May 12, 2026
Host: Keith Newman
Guest: Steven Pivnik (Founder, Entrepreneur, Endurance Athlete, Author of "Built to Finish")
In this episode, Keith Newman welcomes Steven Pivnik, a founder who scaled his software company to 200 employees across 12 countries and ultimately exited for a reported $4 billion. Beyond the business realm, Steven is an endurance athlete—17-time Ironman triathlete and Everest summit finisher. The conversation draws deep parallels between entrepreneurship and endurance sports, focusing on how discipline, preparation, and finishing mindset are essential for founders—not just starting or scaling, but finishing strong and extracting value from their journeys.
"I’m a firm believer that entrepreneurship is an endurance sport." — Steven (01:31)
"I definitely did not build with the end in mind. I built because I thought it would be a better career choice..." — Steven (04:00)
What Breaks First When You Scale?
Identity and Self-Sabotage
The Ironman Equivalent to Scaling a Company
Finishing Strong in Business and Life
Timing an Exit
Surprises in the Exit Process
Practical Tax & Structure Tips
Regrets & What Could Have Been
Advice for Founders at $5-10M ARR
Starting Late, Achieving Big
On Scaling
On Founder Identity
Endurance x Entrepreneurship
Exiting Strategically
Tax Surprises
Dreaming Bigger (Regret)
Valuation Killers
Keith’s Summary:
"Most founders build to grow; the elite build to finish. Discipline isn’t sexy. Systems aren’t flashy. Endurance wins in sports and business."
Steven’s Agreement:
"You summarized it perfectly. Amen." (24:12)
— Powerful, humble validation of the episode’s thesis.
Want more? Find 80+ episodes at The Look Back Podcast on Apple Podcasts.