Matthew Johnson. Prolific Exited Entrepreneur on Work-Life Balance

30 Aug 2024 · 1 h 10 min

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Exit Paradox Podcast Episode Notes

Episode Title

Matthew Johnson. Prolific Exited Entrepreneur on Work-Life Balance

Host

Anastasia Koroleva

  • Background: A 4x exited founder, Anastasia explores post-exit life with remarkable entrepreneurs.
  • Objective: To share insights on purpose, success, investing, and fulfilling lives after business sales.

Guest

Matthew Johnson

  • Career Overview:
  • Sold a healthcare software company 11 years ago after three rounds of fundraising.
  • Acquired and transformed TruConnect into a telecom powerhouse with his twin brother, Nathan.
  • Co-founded Drake Star Partners, a technology investment bank.
  • Balances life between LA and Switzerland while leading a nonprofit providing wheelchairs to disabled children.

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Episode Content Breakdown Introduction & Career Transition (00:00:00 - 00:02:34)

  • Matthew discusses his shift from a successful investment banking career to entrepreneurship, motivated by a desire for adventure over a stable, predictable path.

First Startup Experience (00:02:34 - 00:03:23)

  • Transitioned to the healthcare software startup, experiencing financial ups and downs before parting ways.

Building TruConnect (00:03:23 - 00:06:33)

  • Acquired a poorly managed telecom company (originally Telscape) with Nathan, leading it through multiple acquisitions and significant growth.

Financial Discipline and Management Philosophy (00:06:33 - 00:07:50)

  • Emphasizes financial discipline over seeking external capital, building profitability through internal reinvestment.

Transitioning from Finance to Entrepreneurship (00:07:50 - 00:12:42)

  • Discussed the mindset shift from an employee in finance to an entrepreneurial leader, focusing on managing teams and making strategic decisions.

Balancing Multiple Ventures (00:12:42 - 00:15:08)

  • Shares insights on balancing TruConnect with other entrepreneurial pursuits, including an investment bank and various international ventures.

Considering Exiting TruConnect (00:15:08 - 00:19:05)

  • Matthew discusses the potential challenges of selling a highly regulated telecommunications business.

Lessons in Hiring and Management (00:19:05 - 00:23:28)

  • Reflects on hiring mistakes, learning to identify the right people, and the importance of a strong team culture.

Managing Investments and Personal Fulfillment (00:23:28 - 00:33:05)

  • Insight into balancing investments with personal satisfaction and the challenges of maintaining fulfillment post-exit.

Impact of Entrepreneurship on Family and Personal Life (00:33:05 - 00:37:21)

  • Discusses the effects of entrepreneurship on family life, emphasizing the importance of time spent with family.

Raising Entrepreneurial Children (00:37:21 - 00:41:06)

  • Shares thoughts on guiding his children to understand the value of money and work ethic without spoiling them.

Reflecting on Angel Investing (00:41:06 - 00:50:02)

  • Critiques angel investing as a less favorable avenue compared to direct business ownership and the unique challenges it presents.

Charity Work and Personal Fulfillment (00:50:02 - 00:58:59)

  • Outlines involvement with Momentum Wheels for Humanity and the joy derived from impactful charitable work.

Life Philosophy and Future Goals (00:58:59 - 01:08:21)

  • Discusses the ongoing search for purpose, the need for challenges, and the balance between work and personal life.

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Key Concepts and Takeaways

  • Entrepreneurial Drive: Matthew emphasizes that the motivation for entrepreneurship often extends beyond financial gain; it includes personal fulfillment and the pursuit of passion.
  • Investment Philosophy: Advocates for understanding the financial landscape thoroughly before making investments and emphasizes the importance of betting on capable entrepreneurs.
  • Work-Life Balance: Balancing multiple ventures while ensuring quality time with family is crucial for personal happiness and fulfillment.
  • Charitable Impact: Engaging in meaningful charitable work can bring immense satisfaction, beyond financial contributions.
  • Life Lessons: Acknowledges the importance of learning from failures, both in business and personal relationships, as integral to growth.

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Conclusion

  • The episode concludes with Matthew reflecting on the importance of legacy, aiming to be remembered for positively impacting the lives of those around him. He expresses a desire to continue building and exploring new opportunities while contributing to charitable causes.

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This episode of Exit Paradox provides valuable insights into the intricacies of entrepreneurial life post-exit, emphasizing the balance between personal fulfillment, family life, and the pursuit of meaningful endeavors.

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Transcript

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0:00To me, I looked at that and wasn't like, oh, this is great. I've got a path to make a lot of money. I just felt like, all right, I'm locked into one thing. I'll be doing this one thing for the next 30 years. To me, that sounded incredibly boring. So I just felt the motivation to go do something very entrepreneurial and really take a lot more risk. Matthew Johnson. He sold his healthcare software company 11 years ago after leading it through three rounds of fundraising. In just three years, alongside his twin brother Nathan, he then acquired and transformed True Connect into a telecom powerhouse.

0:36Matthew also co-founded the technology investment bank Drake Star Partners, leveraging his early investment banking career in New York City. Balancing life between LA and Switzerland, he also leads a non-profit providing wheelchairs to disabled children. Today, we discuss Matthew's truly precious post-exit lessons on staying motivated through multiple ventures while fully enjoying life and raising entrepreneurial children. So Matthew, thank you so much for joining me today. Thank you for having me. Very exciting to hear your story. Looking forward to talking about it. So Matthew, you had this really successful investment banking career in New York.

1:19then you suddenly stopped and moved to LA to join a healthcare software startup correct that's correct I'd love to know why similar to other people who are in finance who decided to do something different it was really about wanting to do something more entrepreneurial even though I was making very good money investment banking yeah and was getting great experience I just got to a point in my career where I said either I stay and I do this forever and that's just the way I thought back then of like I'm locked in to be investment banking for the rest of my life and the thought of that frankly terrified me so I was like I can't despite the money being as good as it was particularly back then I just couldn't bring myself to do that for the rest of my career it just wasn't to me I looked at that and wasn't like oh this is great I've got a path to make a lot of money I just felt like all right I'm locked into one thing I'll be doing this one thing for the next 30 years to me that sounded incredibly boring so I just felt a motivation to go do something very entrepreneurial and and really take a lot more risk so you wanted to explore you wanted a sense of adventure and see what else is out there correct what's this life is about interesting it is quite fascinating because most people I talked to they clearly had a financial motivator in there for startup by necessity or by other reasons usually you know thinking about financial freedom uh that was the reverse i had money and i said let me lose money exactly exact opposite exactly and things played out just that way so i started with some money lost the money going to a startup and basically started all over again after that so so i really want to hear all the details about that three-year relationship you had with the startup because you raised the money for them three times yes raised a fair amount of money for the company during the process of when I was there and then ultimately didn't see eye to eye with the owner of the business and finally just parted ways with the business after I think about three years and that's really my brother I have an identical twin brother as my partner and we we would both had discussions about hey let's do our own thing we were both both just happened to be in Los Angeles and so we made a decision to do something together at that point in time Yeah.

3:30And then you guys bought into what's now called True Connect. Correct. So tell me more about that. I like that expression bought in. Wow. I mean, it's been a journey of highs and lows is the only way I can describe it. But when we, my brother and I, interestingly enough, we had started our own kind of advisory investment banking firm in L.A. And when we did that, we really did it with the eye of, all right, this is something we know. let's do this but let's look for opportunities to buy a business invest in a business so we invested and invested in a variety of businesses over the next probably four or five years and that's when we ran across a telecommunications company originally called Telscape and the two of us thought interesting business not particularly well run what if we buy it and so we approached the board of directors we put the money together somehow and we made an offer by the company the board accepted it and we ended up buying the company I think in 2006 feels like forever ago now so a long time ago and really over the span of the next 15 years the two of us ended up acquiring three or four other companies merging them all together and then building up the company from there and I mean last year the company was the largest private company in this segment of telecommunications market in the United States yeah it's quite impressive so it took you like 14 years 14 years and we never raised outside capital so we did it with our own money our own really just driving profitability taking the profitability from the business and putting the money back into the company and thinking of ways how can we diversify revenues how can we streamline costs and so really took a very as I mentioned to you before I mean a very financial approach to the way we ran the business from the beginning and I mean make no mistake I I mean, we may be investment bankers and think we're super smart, but we made every mistake that every entrepreneur makes.

5:27I mean, bad hires, terrible decisions, not getting rid of divisions quickly enough, keeping people longer than you should keep them. I mean, every mistake you can think of we made. And so I think we wrote a lot of highs, a lot of lows. But certainly in the last two to three years, the business has just done better and better year after year. Yeah, it's really impressive what you've done to the company. So I've mentioned it to you in a different conversation that one of the reasons I found your story so fascinating and really wanted you on this podcast is because it's very unusual how you went from the financial industry into running a business, into entrepreneurship.

6:07And then we'll also be talking about the technology investment bank you're running now. But you basically went from the financial industry into entrepreneurship. You mentioned that you made all these different mistakes. most of the people I talk to do the opposite and they find investing really really hard in terms of the mindset how you how you think so differently so right if you do it the other way around did you find your mindset this change in the mindset is it was challenging for you that's a great question I think I've ever been asked a question before I think is we discussed a little bit before him, I think my, what was great was the background investment banking, I think really helped both because he was in investment banking as well.

6:55I think really helped the way we looked at companies and opportunities because we really looked at it financially first because we weren't, I mean, can't really, we weren't doing just a complete startup. We were looking at a company that effectively had a broken balance sheet and we understood financially what needed to be done to fix it. And so when we saw that, we saw a huge opportunity of, oh, this management team doesn't know how to fix it financially we know how to fix it let's buy it fix it bring a new management we then made all the typical startup mistakes after that yeah so we did a great job getting it financially structured and the business making money and then we made the classic mistakes of hiring wrong people and you know entering into markets you probably shouldn't have entered into um but i think that background i think was very very helpful and it has been since then as i mentioned before i think one of the things we take a tremendous amount of pride with this company is the fact that we've never raised outside capital yeah and I mean last year we did about half a billion in revenue and we haven't raised we have not raised equity from anyone in the company anyone outside the business other than myself and my brother so because you don't have to because we don't have to I mean there's you structured it you know cash flow first we did I mean there were three times we had to invest again not to sound like everything was perfect with this company because it almost went under in 2009, obviously because of the financial crisis.

8:14We had to reinvest then. We did a leverage buyout of another company. We had to reinvest again then. So it wasn't all just purely cash flow because we did invest several times. We just elected that we really didn't want to bring in outside investors because we knew the pitfalls of doing that because we'd both been at venture-backed companies. We both obviously work a lot with private equity investment banking and just had no desire to have someone tell us how to run the business. because we felt like we knew, even though I said we made mistakes. We learned, and I think in the long run it's been great because obviously we have complete control of business currently.

8:51So would you sell that company now? Would I? Yeah. I mean, if any buyers are listening, I'm selling. I mean, we've looked at selling. It is a highly regulated market we're in, which makes it more challenging. Obviously, as you mentioned, you're in software. I mean, that's the beauty of software. It's not regulated. and there's lots of buyers. Everyone knows the multiples. This industry is a little more challenged in that respect. So it really is more of niche buyers. And there's a couple issues we're dealing on the regulatory side right now. There's some wood I can knock on, and I'll knock on it now, that if we get through those issues that should be resolved this year, then it really opens up an opportunity to sell the business.

9:29And I think my brother and I, at this point, would be very open to that. Okay, interesting. So you have this amazing cash flow on the business. you have the control but you still wouldn't mind selling yeah i mean it's why is that yeah again a good question i think part of it's from this business my brother and i have started other businesses so we have uh we have a company in india we have a company in china we have a company in israel um different companies we've acquired with some of the cash flow others we've just been total startups um as i mentioned there's a fitness company i recently took over in los Angeles so we have other interests and I've been doing this so long I mean if I put my financial hat on no one's in a deal for 15 years I mean it's the exact example you don't do so I think for us we would welcome the opportunity to be able to actually exit the business and focus on other things so would you say you're spreading yourself too thin or you just have this itch again to see what else is out there well I think I think in the past we definitely spread ourselves is too thin because then we in the past we were doing as you mentioned before like we're part owners of an investment bank that's out of new york now i'm just on the board of that company i've pulled back from that i was trying to do that and run this business and run other companies we invested in all at the same time and i had a mentor of mine at the time say like you know i think you're spreading yourself too thin yeah and i was like i can do all of this yeah and he was right i mean 2009 happened and that really opened my eyes up all right i can't be trying to run an investment bank trying to run a small credit fund trying to invest in all these different companies and run this business as well so i think i learned a lot from that mistake and um really said about my brother and i in probably about 20 2012 where we just committed 100 of our time to this one business because at that point the size was getting to the point where it was yeah okay it's a big company now we really need to focus all of our time on this so you wouldn't consider hiring a CEO stepping down focusing on other things you would prefer to sell oh I don't know if I can answer this question my brother ever watches this he knows what I'm thinking right now um we did try twice okay and it was a miserable failure yeah so I'm sure many other people who live with might listen to this will have the exact same experience many people in my audience yes you get the resume you interview them you're like this and look one of my blind spots frankly um is hiring people like i have a blind spot i tend to trust people too much i tend to expect the best this person's going to come in and give it a hundred percent it doesn't dawn on the fact that someone could get a job and basically view that was the whole mission of getting the job and now they'll just kick back take this big salary tell everyone else what to do even though they don't really know what they're doing um and we we actually recently had a very bad experience with that in 2022 um if those individuals ever watch this you know who i'm talking about and it was uh it was a mess because i was so excited it was actually three executives that i brought on i was very excited and it was a mess so within 12 months they're all gone you don't want to go through that again no i just feel at this point i'm we brought in a bunch of new executives and the new team i have right now is great.

12:48Very, very happy with them. But my brother and I think are, I think similar to many natural owners, a little bit control freaks. We really want to be in control. I gave it a shot at letting someone else more or less run the company. And there was a path from president, the CEO for this individual that we laid out and it just didn't work. And I think, I think from my perspective, you know, at this point with where the business is now, I really want to shepherd it to its final destination and as you said I mean I don't have to sell I mean I could just cash flow the business for the next 10 15 20 years and never sell but I think from my perspective I think my brother I would love to be take an exit and we'll do other things because we have a lot of other interests so you also in parallel right run you you know private equity firm would that be the right name for it it's more than investment banking it's an investment banking firm that my brother and i are part owners of yeah we're minority owners of that business i'm on the board as an independent director now so it's really just a way to stay involved in that world but not actively i mean honestly i'm just at board meetings i try to help as the business is growing the firm is called drake start partners out of new york they've got a terrific ceo he's a good friend of mine running the business day to day so my involvement with that is very much just from a board level so the way i view that is we have drake star we have cloud mobile we have upverse we have true connect we have we fi we have these different businesses where we're either minority or majority owners of the business but we're not actively running any of the business other than true connect yeah we're spending kind of 100 of our time on that and if you sold true connect you would probably get more involved in in the other ones correct or i mean as i mentioned i just got involved in a fitness app that i really i personally use it and i love it it's called shred if anyone else likes to work out you can download it on you know obviously um you can download it both uh on ios as well as on um wow just totally blank right there for a second it's all right android yeah android thank you i was like i don't know why i'm blank on android because I deal with Android all day long.

15:02If you sold today, what would you do? Because you obviously had an exit from your healthcare software business. So you've been in this place. Now on a personal level, what would you do? Well, number one, I would control the exit. I think one of the advantages that you alluded to before is the fact that my brother and I do have an investment banking background. It's very unusual to have two executives, both in investment banking, both running a business of this size. So I know the game on how to sell a business. No banker is going to come to my office and trick me or convince me to do something I don't want to do because I understand exactly how it works.

15:42I think a lot of individuals who, I mean, obviously not private equity backed, but companies they've built without really bringing outside capital don't have that experience. And I've seen it firsthand as a banker, watching these people kind of struggle with like, what all this means? Like, what do multiples mean? How do I understand the leverage that they want to put on the business to buy it? And do I want them to do that? Whereas with me and my brother, I know how the game's played. I totally understand it. I know the type of exit I would like, which is probably just a strategic buyer. Obviously, all cash, I mentioned stock.

16:15So I think from that perspective, we have had some other smaller exits along the way, like smaller companies we bought and sold and things like that. But this exit would be a substantial one, just given the size of the business. so it would be very hard for me and my brother not to be very very actively involved in exactly how that exit occurred what i would do after that i mean i'm not totally sure i think i mean it'd probably be more of what i'm doing right now it's looking for kind of unique companies where we could buy into something um and own it because i really have no interest in being a minority shareholder in something um and i think the first thing i'd probably do is buy something that's not regulated okay because that's one of the big reasons i've exit this business is just so sick of working in a regulated market it's a barrier to enter for it is and it's a psychological abuse you have upon yourself i mean it's also being in health care or telecommunications or some of these industries that are so highly regulated or aerospace yeah we're dealing with these different things that are beyond your control in terms of how you're able to run the business without having to think about like oh what if this regulator decides they want to do something stupid and now suddenly I've got to run around try to like address that issue in the business this particular part of the telecommunications industry is very niche and very odd because the regulations are extensive and so from that perspective it gets really frustrating year after year and each state has their own rules as well as federal rules and we're very good about following all the rules, but I literally have an entire group dedicated just to following the rules of the industry.

17:54And I know if I were to do another business, I'm not doing that again. Yeah. So, for sure. I can understand that. I had a telecom business, actually, and at some point I caught myself thinking that I don't own it. I own it together with the government because the government was so involved in my business, almost like I had a partner, but that partner had the majority stake in my business because it could tell me what to do. Exactly. So maybe you had a similar feeling. And we are control freaks. and sharing control with the government is not necessarily... That's your worst partner. Exactly, the worst partner.

18:24Part to negotiate with. Yes, we always joke in our company. Like, it's a famous Ronald Reagan comment where he said, you know, I'm here from the government, I'm here to help. That's like the worst eight words you ever want to hear in your life. That was exactly eight words, I didn't add it up, but it's true. I mean, I hate to say it, but, you know, state regulators and federal regulators, they're there to regulate, but I think, you know, The problem is that you quite often deal with individuals who feel empowered because of regulators versus just doing their job. So it's really frustrating. So you're like, this shouldn't be this difficult.

18:58I'm trying to get a service. You're hiring me to get a service out to a certain population. That's what I'm doing. Just eliminate all the red tape so I can do what I'm supposed to do. So I think for sure I would not get in regulated business after this. So, Matthew, you and I had a conversation about angel investing. And I'd love you to share with my audience how you see angel investing versus the kind of private equity investing that you're doing. Interesting. Yeah, as we've commented a little bit before, I'm not a huge fan of angel investing. The interesting thing is, again, I did it in reverse.

19:32I did a lot of things in reverse. I was doing angel investing 20 years ago. So again, the classic angel investing in the West Coast of the United States is like$50 ,000,$100 ,000 in 10, 15, 20 different companies. And I don't enjoy it because it's just you have no control. It's all just a bet. I mean, quite often everyone, there's lots of good salespeople out there. You hear all kinds of great stories. I recently lost some money on another investment that my wife and I made. So I think we I learned my lessons a little bit, but not completely But I think from our perspective and mine and my brothers in particular the angel investing part Just doesn't excite me.

20:13It doesn't get me excited Having someone have a great idea. I think it's amazing and there's great angel investors many who are members of Tiger Some are in my group as well. I'm not one of them. I don't I don't think I made any money on my angel investments It was like over 15 So I was like yeah, I'm done with this yeah so i just i like i mean probably similar to you and other people who have built and grown a company really having and not just the control but having more ability to influence a business to me is way more exciting than oh let me put a little money here here here and here and let's hope this works so just not something i enjoy so we talked about how you do things differently from everybody else I talk to in the sense that you are an investor first and an entrepreneur second.

21:02So your motivation to start a company wasn't financial. It was more about exploring life. Would you say you've achieved what you were hoping for by starting a business and run or at least joining the business and running it successfully for 14 years? Yeah, I would say I had, but I had no idea I would take this path. So, I mean, I don't think my brother and I ever intended to be in this industry. This opportunity just found us. And then, I mean, candidly, originally as a financial person, our goal was to streamline costs and sell it. Buy it, streamline it, and as they used to call it, flip it. And that was really our whole goal.

21:46and I like to tell people at this point I'm 15 years into a five year plan which was to buy the company streamline, sell, move on to the next thing and I mean I think some of it has been out of just necessity and I think other part has been out of I think my desire the more my partner got more and more involved the more I really enjoyed building the company because I do think anyone who is an entrepreneur I like to think I'm more of an an entrepreneur person now that I'm a finance person. I feel like it flipped probably 12 years ago. Yeah. Where, like, I really enjoy building things. Like, I don't get as excited about being on the financial side of the business.

22:25I really like finding the right people, getting a team together, focusing on a strategic goal, executing that goal, and then getting the financial performance to follow that execution. To me, at this point in my career, that's way more interesting than just, like, oh, this business looks interesting. Let's find a way to structure a way to buy it. Yeah. So I think that's changed. Do you think that creative builders gene was always in you or developed over time? I mean, I think it was because I think that's the reason I left investment banking. I think I felt something pulling me. You were in the wrong place.

22:59Yeah, I was in the wrong place. And I really suck at working for other people. I mean, it's a fact. Asking the people I used to work for in New York. Like, I was terrible at working for other people. I just always felt like I couldn't fit in a box. and I'd have people I reported to being like, you're just supposed to do this. You don't need to go beyond that. I'm like, that's not the way I operate. So I think for me getting, I mean, for some people who have been wildly successful in that industry, hats off. Like it takes a real ability to deal with all the politics of that industry. Not only the hard work, but a lot of politics just wasn't something I could do well.

23:34And so I think that entrepreneurial bent in me finally just forced me to say, all right I'd rather like lose millions of dollars and leave this job and go do something making zero because the company I joined actually ended up effectively being bankrupt when I joined it so I got there and we didn't get paid for like I don't know 18 months or something like that so good experience not a good financial one but a good experience yeah we talked about it an expensive lesson an expensive lesson yes yeah it happens so on the personal side of things how does your wife feel about your uh change from the financial industry into into business were you married at the time um we were we've been married for 21 years i know the date i know the date's better than she does so this is always a joke we have but um no i think she i think she's always supported whatever she's seen me do that she knows motivates me um i think one of the things always people talk about like with good entrepreneurs this seems like a kind of classic comment everyone makes just like you have to have grit but it's true yeah like you have to have a certain kind of relentless drive to get things done and I think both my brother and I have that and I think my wife always knew I had that so even when I was investing banking I think she used to think like why are you doing this like this isn't you like she used to be kind of my biggest um proponent even when we were dating of like, why don't you go do something different?

25:03This clearly isn't your thing. And because I mean, even though I was doing it and I enjoyed it at times, I actually kind of deep down kind of hated it. And she was like, why are you doing this? You're working 100 hours a week. Go work for yourself. Yeah. And so I think when I made that move, she was very, very supportive. I mean, obviously she was nervous because when we did get married, I think, yeah, I mean, when we did get married, I mean, basically I was broke. So I was like, all right, now I have to make money. so yeah entrepreneurs have this crazy rate of divorces because you know often spouses don't don't understand um why somebody behaves that way yeah no i think actually i think she's a psychologist your wife so you're lucky you married yes she understands all my issues but i do think she has always been very supportive and i think she knows i mean she sees how hard I work and she jokes as well as some of her family members about kind of the relentlessness that I think every entrepreneur has it but I certainly have it as well just every day just kind of doing what you have to do to make things work and I think for her I mean obviously the lifestyle that we have now it's worked so like we're able to do I mean I think there's a comment that I always read about kind of, you know, what does entrepreneurship or running a business or exiting or whatever do for you?

26:25And I think it's true. It's not just about the money. It's not just about the control. It's not about the kind of feeling good about yourself. At the end of the day, I think it's the freedom. Yeah. I mean, because at the end of the day, the ability to say, I can do what I want to do. And if I want to live in Switzerland or I want to work in LA part-time, I can do that. And there's so many other people in this world that never are able to do that. Yeah. They're down to a desk or they've got some of the job or some of the commitments or other things are going on financially just to give them that freedom.

26:58Yeah. Though I have to say that at some point I felt that having too much freedom is actually very stressful after my first exit. And I then realized that freedom is such a beautiful thing, but it's only a resource like money, like energy, like everything else. We can have it, But then it doesn't translate into happiness necessarily right away. We still need to use that resource very wisely to get ourselves to a happy place. Right. So I wonder how you think about it. You have financial freedom. You can basically do whatever you want. I know you're running a business, but you could basically maybe tell your brother you don't want to do it anymore.

27:39Or try to hire someone else again. I'm thinking about that right now, Nathan. You got this. Okay, blame me, Nathan. if I seeded their own idea into your brother's head. But like if you, you basically have all this freedom. You can do whatever you want. You can live whatever you want. How do you feel about it in terms of how you can translate it into a more fulfilling life, a more purposeful life? We're getting philosophical now. And whether you're doing it. Yeah. Yeah. Challenge your thinking. a bit. I mean, it's an interesting question. I think you get over a certain age. I mean, I didn't have an exit young.

28:23So it wasn't like I had some exit like in my early 30s. I was like, oh, I've got all this freedom and all this money. And that might have been a disaster. So it took me and my brother a long time to get to this point where we do have the financial freedom to kind of do some things we want to do and live a lifestyle how we'd like to live. But I think from that perspective, I think it's really, you know, at the end of the day, for us, you know, ultimately my goal is to find a way to exit this business and then find a way to do other things that are fulfilling, whether it's like charitable work or, you know, my brother and I are fairly involved in a lot of different charities and donating money and things like that.

29:03But I think just spending more time doing things like that probably would be more fulfilling. But I'm not philosophically part of the issue for me is like even if i sold this business i don't know if it's going to be enough and it's just the way i'm built enough of what i don't know i don't know if it's going to be enough like i'll need to do something else like yeah even if it's a lot of money it won't be like enough money and maybe that's the wrong way to look at it but that's kind of the way i feel of like internally it's and maybe that's a bigger issue that i need a psychologist for but is it well you have one at home she doesn't know how to help me with that i expect you to be quite psychologically advanced well I mean she doesn't hate that answer probably she's like oh it's not enough okay keep going so okay but but would you say that if you don't feel satisfied if you don't feel you have enough that affects your level of happiness or you actually embrace that feeling you don't have enough because you feel this is the source of your drive yeah maybe maybe Maybe it's the driving source is not feeling like you're enough, so you have to keep doing more to be enough.

30:09I don't know. Maybe that's part of it. But I think for me, now that I've really discovered I like building things, I think it would be very hard for me to sell a company and go on a golf course. It's just not my thing. I enjoy golf. It's not fun for you. But after a week, I'd be bored out of my mind. So I think I need a challenge and the adrenaline of doing something. and I mean so much more is very I know a couple that are very happy they were tired in their early 50s and you know doing pretty much nothing and they're good and for me I just I look at that I'm like I could never do that I actually find that for most people it's just a temporary solution because you need to feel you're growing you need to feel you matter right you're contributing change something right that if you're getting recognition back from the society it's for something valuable i think we all need that on on some you know genetic level no it's true i mean i wish i had a better answer there because i mean it's actually i'm going to think about this question after this interview but um i i think at times i'm like all right like what would i do ever sold this business and like i don't know that i have a great answer all i know is like i don't think i could just say all right let me take like five years off and travel the world and do nothing I can do all that now I can travel as much as I want I can go where I want and still be involved in doing things with the business Yeah, and you like that I do like that, yes Talking about traveling So you now basically live between Lugano, Switzerland Correct And LA, which is very far You travel once a month back and forth How does that work as a lifestyle?

31:51I mean, it's not easy especially the first year was challenging as hell but I think over time I've you know I've grown to like and appreciate it the fact that I think I look at it more even though I'm tired and sometimes a little bit worn out by it I think I just have a grind mentality with a routine that I know what my routine is when I get to Los Angeles I know my routine when I'm in Switzerland and so I just stick to the routine get up early work out if I fly in the night before I'm up early the next day working out just doing my routine as if I never left and for me that's very helpful because it just gives me the mindset of all right I'm in LA I'm here to do this or I'm in Switzerland I'm here to do this and it's and it's a luxury to be able to say okay I can live in Switzerland and live in Los Angeles and have the ability to kind of go back and forth really whenever I want and so that's I think I think a luxury that while challenging I think I'm very lucky to have.

32:47So if you were to rate your level of fulfillment in life from zero to ten oh yeah I didn't know we're going to these questions no we're good very good next one we're getting marriage questions so yeah we're just warming up yeah so oh boy so so on a scale from zero to ten how fulfilled are you overall in life hmm I mean I would say pretty high I mean I think I would say probably I don't think anyone can say a 10 I mean so I'd say probably like an 8 yeah that's high yeah and I feel like I think when if the people specifically like around you are happy like I at the end of the day I've got my sister-in-law my my wife my kids um got a great lifestyle Lugano and everyone's very happy like I think at the end of the day you look at that and you basically get a sense of like all right like I helped make this happen yeah and so I think from that perspective that provides a lot of fulfillment of course yeah so you must be proud of your own achievement that you you could do that right you see the lifestyle you give people and and extends my wife and i support a large part of our families on both sides yeah so i think i think the ability to do that and kind of financial freedom and flexibility to be able to do that i think that provides i think a great sense of accomplishment like all right here's others who you're related to or maybe need help or need support and you don't always love giving it i'm not gonna lie at times they're like i'm done doing this but at the same time the ability to do it i think makes you feel like all right this is you know i think you can't you can't not help feel like all right this is great sense of accomplishment being able to do that of course of course and i can totally see how it also feeds into you know the sense of love love and belonging to them in the family and you you play such a crucial role in the family that makes a lot of sense um anything else that feeds that high level of fulfillment for you um i mean i would say obviously i mean i think the obvious things outside of the kind of contentment that's around you is obviously the i think having a really great marriage having three great kids we're all healthy smart doing well um and you see that you see kind of like the fortune that I have to have all those things.

35:32As you said, like quite often entrepreneurs' marriages don't work for different reasons. And I think I'm lucky in that regard that I've been married 21 years. She's been incredibly supportive throughout the entire process. My kids are great. And I think one of the things I didn't mention before is I think the fact that you get the opportunity, and at least I did as an entrepreneur, like spend a lot of time with my kids. That's brilliant given that you have to fly back and forth a lot. I mean this is obviously a little older now. When they were younger and I was like working at my company, I really made a point of spending a ton of time with my kids.

36:09So like I feel great that I was able to build something at the same time, not like always gone. If I had said investment banking, I mean that would have been traveling all the world, gone for weeks, months on end, on someone else's schedule. Yeah. And the ability to like have a company still spend a lot of time working on it, but then And also having the ability to say, all right, hey, I'm spending this weekend with my kids. And I'm going to coach Little League and do other things like that. And so I leaned into that pretty heavily when they were younger. And now you're saying that you feel happy that you avoided that very typical regret of people who stay, say, in investment banking.

36:50And never have that luxury. I hear that a lot from my, I have a lot of banker friends. So I hear a lot that I missed out on my kids growing up. I was working 100 hours a week. I'm on someone else's schedule. So my life is not my own. And I think in that regard, my kids have to back me up on this one. I spent a lot of time with them when they were growing up. So I was probably a little bit psycho because I very much wanted to be an active part of their life growing up. So it wasn't like, oh, I never saw dad. He was always traveling. He was always working. and so I think that's been great. I think I'd like to think I have a really good relationship with all of them.

37:29Would you like your kids to be entrepreneurs and not have a corporate job? Absolutely. Okay. Yeah, I would never. Do you tell them? No, I don't tell them anything. I really don't. I mean, my father didn't. My father was head of neurology at Johns Hopkins for 20 years, a very accomplished doctor, and he never once said go into medicine. So I think from that perspective, I would never tell them, you should be an entrepreneur, you should be a doctor, you should be a lawyer. Don't be a lawyer. You can hire those guys. I got lots of them. But I think from that perspective, I think I would never tell them what to do if they came to me and said, hey, Dad, I did this as an experience to work at this company and I want to quit and start my own company.

38:21be like great like let me help you with that but do you consciously realize that that you are a role model and you're probably affecting their thinking by doing what you do and that's how you deliver that idea to them well i think i mean some of the risk and i'm sure you experience this as well as i mean financially none of our children necessarily would have to work again if you really take a step back and be like all right my kids can do nothing if they wanted to i wouldn't be happy with that at all but um i think that's one of the challenges though trying to balance out of like how do i ingrain in them kind of a work ethic while also providing them with kind of a unique situation where like they have some financial stability at a very young age and so it's it's a difficult how do you go about it because there are two school schools of thought really give it all away like Warren Buffett or yeah either either either you bring the children in and you train them to manage wealth and you're very open about everything right or you're saying no you guys need to be hungry I'm not giving you anything so you make your own mistakes you you you're driven you need to build your your wealth yourself so in that spectrum where are you in your thinking um I think I mean I think I believe I'm probably in the middle because I think it's a little bit of both.

39:48I certainly think we're not the type of parents to like lavish things on our children. And yes, they've had unique opportunities to live in Switzerland, go to school in Switzerland and do things like that. But those are more experiential. They're not just about like, let's spend money on stupid things. So I think from that perspective, they've seen that. They know that we're not so frugal that there's like, why don't you spend any money? But at the same time, I think they've learned from that. And I think I learned that as well from my parents. My parents actually were very frugal. And I learned kind of like the value of money and kind of like, all right, well, it would be nice if I got older if I had more money that I could spend.

40:26So I think we have instilled in them that sense of the value of hard work and getting money. At the same time, we are starting that process of really introducing our two oldest because they're 16 and 17 to the concept of you will have money. and by most measures a substantial amount of money at a fairly young age, like how do you manage it? And so there's actually a lot of great firms out there. I've just moved to one of them on the wealth and management side that's helping. They actually put together courses specifically for children of business owners who have exited and things like that to really build a relationship with the money at a very early age so that you don't do dumb things with it, get an inheritance and go out and buy a Bugatti or something idiotic like that.

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41:13And there's a big trend now of second generation giving money away and they mean very well. But they don't necessarily have the financial discipline and understanding how to do it right. It's a huge trend. I'm going to forget the old concept of poor man, I'm not going to get this right. You start out poor and then you get rich And then by the time you get to the third generation, like basically you're back to being poor. Being poor, yeah. Because people just find a way just to blow the money in kind of the second and third generation. So I think it's, we're trying to show them how to invest long term.

41:51And using this financial wealth management group that we're using now to kind of have this class to show them, hey, we're investing for the long term, not just for you, but for generations going forward on how to basically preserve capital and not just waste it on things that cause you to deplete your resources.

42:12So if you imagine that I just sold a business and for the first time I have wealth to manage and I don't know how, but I theoretically would like to invest into other businesses the way you do and I came to you for advice, Like, you know, tell me the basic rules of doing what you're doing so successfully. Hmm. Well, I would caveat that a little bit. I don't know if I've been that successful, but there's definitely been some really bad misses. But you've learned your lessons. That's what I'm after. Yeah, I've learned some lessons the hard way. I mean, losing money is the best way to learn a lesson.

42:52Exactly. But I do think that people who have exited business, I think it's different strokes for different folks. The whole expression of just kind of like, if you're really good at building a business, I think trying to go from that to basically investing in business to acquire business, I think that's just a total different skill set. Exactly. It's very hard. It's very hard to do. And I've seen people try to do it and be awful at it. I think I started young enough with a financial background focusing on using that financial background to actually acquire my first couple of businesses. I like to think that question asked before that actually going to reverse that in the last 15 to 20 years.

43:33So I feel like if you start really, really young from a financial perspective, doing that investment and then learning from those mistakes on small things, because we made a lot of mistakes on small companies, and then build that and then grow your own business, whatever it is, I think then maybe it's a little bit different. I think someone being just a pure entrepreneur, cashing out for whatever,$100 million, and then you're like, you know what? I'm going to go into buying companies. I think you're better off just investing that money because I think you'll learn the hard way how to lose money.

44:02Lots of people do that, and they do lose money. Like my observation, I've been talking to executive founders for 13 years. My personal observation is that number one way for people to lose money is to start a new business right away before they actually understood what made them successful before. Yes, that's a common one. And that combined with the desire to not have outside investors means that they put their... All their money in. Before doing proper exercise in capital preservation, they put too much money in. They're too optimistic. They're too, I should say we because I made this mistake, we're too arrogant, right?

44:42So that is by far number one mistake because it's so much money so fast and it's very hard to stop, right? To get out of it. But the second one is buying into other businesses, thinking that, you know, expecting that you cannot work as hard as before, but yet get the upside. Get the upside, yes. So tell me how you think about it and whether if I were this person asking for your advice, whether you would tell me, go for it. Well, it depends on the business. I mean, also the industry. I know plenty of people have gotten very, I mean, I think it's also timing too. I mean, you've had some exits very young.

45:22You've made a lot of money. And I think those who have experiences are like, oh, this is going to happen every time. And the fact of the matter is, is that a lot of chores lightning only strikes once. So the reality is, there's a lot of people only have one great exit. And then they think it's going to happen over and over again. And it just doesn't. And one great exit's all you need, frankly. But I think the perception that you can automatically multiply that because you're successful at once, I mean, it's unusual for that to happen unless you're someone like Elon Musk or someone like that who's truly kind of broken the mold in terms of being just a repetitive entrepreneur with a high level of success.

45:59I think you're better off if you're going to invest and you've had a successful exit, invest in something you know. like the one thing you cannot do is exit a software business and then get in like movie production or exit software business and go to consumer products well even in software business it's a whole world it's its own world but like yeah within a niche of software whatever it's like sass and you're saying all right like if i'm gonna invest in another business it's going to be in the exact vertical that i played in because i know that vertical cold and it's going to be in a CEO that I've met and I know from a previous life who can execute.

46:38I think it's, I mean, there's so many earlier stage businesses out there you may invest in, terrific salespeople. I mean, we've all seen them. Frankly, a lot of them, I mean, I think I'm a little biased on this comment, but a lot of them don't have the grit to, if you want to be a successful entrepreneur, you have to suffer. Yeah. Yeah. That sounds like you have to suffer. None is true. I mean, I think anyone who's done this and been successful at it, like, you have to suffer and you have to keep going. And his comment to this class, I think with Stanford grads, was like, you guys have had it too easy.

47:14You guys really have never suffered. Like, you've got full paid tuition. Your parents paid for everything. You've gone to Pashi school. You're going to make$200 ,000 a year leaving the school. You've never really suffered. And so I think that is very true in terms of, like, being able to really be successful. like a willingness to take on that suffering and power through it well but this is exactly what exited founders hope to avoid by buying stakes in other businesses you quite often you're going to invest in that person who's not willing to suffer because you're going to think oh this person's like me they're going to no matter what they will make this successful the idea is great they're smart they want to name the school you know i'm going to make a gazillion dollars with this person because they have what I had.

48:02And the fact of the matter is you can't figure out whether they have what you have until you see them do it. And I've seen a lot of CEOs... How do you avoid this mistake? Because now you have a lot of experience doing that. How do you avoid that mistake? I mean, trust your instinct. I mean, I think that's the only thing you can do. Like, I've recently had a very bad experience where my and my wife had... Actually, if you're lucky enough, My wife is a psychologist. I should invite her to every interview because, you know, her instinct is always like don't hire that person or don't do that investment.

48:37And I'll do it anyway and I'll be wrong. I'll be like, oh, man, I should have listened to her. I told you so. Yeah, totally so. So if you have a wife like my wife, just take her to every meeting and she'll say yes, no, yes, no. Perfect. But not everyone has that. Your secret weapon. Yeah, but you have to listen to them. So let's learn by mistake. So you have a secret weapon, but you're not using it. Yeah, I haven't been using it. I'm using it now. But we both learned a lesson on this one company because we both ignored, in this case, we both ignored our instinct. And we thought the idea was great, loved the fiery drive of young 20-year-old entrepreneurs.

49:09And the reality is, is once we got involved in business, it was obvious that neither one of them had, I hate to keep saying it, but they kind of had the gene of willing to suffer and really work hard. The whole, for them, it ended up being, oh, we got the investment. We're successful entrepreneurs because we got an investment. I was like, no, that game just started. That's just the start, exactly. We just started. It's not the finish line. And I mean, that company failed so fast, it wasn't even funny. It was, I think, inside of 12 months. So why do you keep doing it, though? Are there better ways to invest money?

49:41You get something else out of it. Like glutton for punishment, I think. Maybe that's it. I mean, in this case, because I mentioned a comment before about being an angel investor, like I hated, for me, doing the little tiny investments where like you own very little of a lot and they all fail is no fun. in this case it was something it was kind of a passion project we had majority control of the structure we put in place um so we felt like oh this is a good bet it's we're excited um we love the idea we love the team and i failed so quickly it was actually kind of embarrassing so you know i won't mention who they are but you know it was it was not a particularly good investment okay so any other advice or guidelines besides listen to your intuition intuition everyone who says that no like that's terrible advice do you have do you have a criteria that that's objective uh when you choose your your portfolio companies or you really think it doesn't matter um i mean objective in terms of industry or like what what's the criteria i mean for me the revenue the margin yeah i think it is you talk about like how an entrepreneur is someone not like me who sold their business and that's all they'd ever done and that's what they know and now they say, hey, I'm going to go invest in companies, is a little bit different than someone like me, who's always kind of done this and then grew a company.

51:00That's exactly why I'm asking you that question, because you're a very unique expert for me. It's a very different philosophy for me. I think for me, I'm very industry agnostic. It's more the opportunity, which is the exact opposite of what I just gave you for someone who came from that industry. Don't do what I'm doing, because that's not what you do. I look at the financial opportunity first. look at the industry the size of it what's broken with the company there's always something broken we've got an opportunity to invest in a company in my because I don't like to do startups except this one example I just gave you and I know why I don't like doing number three is is at the end of the day you've got to find a way to really vet the team that's gonna run it because it's always the expression betting on the jockey not on the horse is I think my Kellogg professor told me that like 20 years ago and that's so true like That is one thing.

51:53You've always got to bet on the person who's running that business, not the idea or the concept. Because if you'll find a really gifted entrepreneur and you can invest in them, they'll figure out a way to make it work. They'll change strategy. They'll adjust the plan, the software, whatever. As long as they have the gene for suffering. Yeah. I mean, but I think those would go together. I think when you find a really talented entrepreneur, they've got the gene for suffering, the ability to make things work no matter what, and kind of unwillingness to quit. So I think you put those three things together.

52:24Now, finding those people is hard. It's like you really have to see them execute. And you're going to see them execute once you put your money in. Exactly. So that's the trade-off. Otherwise, there's no transparency. I think this person is the right person. But I think over time, I think for me and my brother, it's really just looking specifically at opportunity of like, is there something very unique about this business which we think we can take advantage of, given our skill set, which is totally different from someone who's coming from a very specific industry. That's all they've ever done because it's just a different way of thinking.

52:59You've got to be like, all right, let me think financially first and then about the entrepreneurial opportunity. So going back to what motivates you, why you're doing it, because years ago you decided it's not really about the money for you. Right. But it's very interesting for me to understand it. Would you say it's the love for the game? Do you really want to keep doing what you're doing because you love doing it? Obviously, you said it's never enough money. Do I love doing it? My executive team are watching this. It's our laughing. We always joke about the regulations make this somewhat painful.

53:38As I said before, I think it's more the love of building something. Yeah. So building anything. So it doesn't have to be this business. It's building anything. I think when you've got a good team and you see it, I mean, you've seen it. Yeah. When you've got a really good team, it's fun. It's fun. Everyone really rallies around the strategic vision. Everyone gets excited about what you're doing. They're like, even in the hard industry, they're like, we're better than everyone else. And you consistently prove you're better than everyone else. And you feel even better about yourself. So I think that kind of that iterative process of building something for me and perhaps for you is what gets me excited.

54:16Yeah. Just giving someone money and saying, I hope this works, doesn't get me excited at all. Yeah. Which brings us to charity. Because I think lots of people, when they're honest, would say just giving money to charity doesn't actually give me much satisfaction on a personal level. I may still do it because I think it's the right thing to do, but in terms of getting a bit of that fulfillment, that's not the source of that for me. And I know you're involved in a charity giving wheelchairs to impoverished children. So tell me more about it. What's in it for you? What's in it for me? Absolutely nothing.

54:58It's a great charity called Momentum Wheels for Humanity. It's based in Los Angeles. I've been the chairman of the board for eight years. I've been a long time involved in the company. It's a terrific charity. When I first got introduced to the charity from a good friend of mine, he had said, oh, I think you'd come to a meeting. I think you'd like this. At the time, frankly, most of our tourists don't have time for charities. I am the charity. I'm a charity case. I have no money. I'm broke. I have no money to give away. We'll think about it in the future. And so he got me involved in this charity quite a long time ago.

55:35And then I saw something he became the chairman of the board of the charity. And what I liked about it, as soon as I saw it, was it was global. It was immediately impactful. And it was for children. And the fact that you can basically deliver these wheelchairs around the world to third world countries and make an amazing impact on the lives of not only these kids, but their family and everyone else around them in the community. And some of the early videos I saw, we've toned them down since. Some of the early videos were really hard to watch because you're seeing how some of these children are living unable to move.

56:14And you saw the impact of what this had on these kids, having an actual wheelchair and being able to move and go to school and being an active person in the society that they live in. You're like, wow, this is an amazing charity. Because more often, like, and there's some great charities out there, like UNICEF and things like that, that do amazing things around the world. But, like, you're so removed from the impact. And there's so much administrative and cost, frankly, of every dollar comes in just to administer whatever service they're providing. And what I thought was unique about this is, I think, at the time, it's gotten better.

56:46I think it was, like, 90 cents in the dollar was, like, reaching and delivering an actual product to these people most in need. So I thought that was really impactful. And I thought the group and the way they were organized and the way they're focused globally. So just, I mean, it touched a bunch of key points for me. Like the global impact. I loved to travel over the world growing up. I'd actually seen a lot of poverty in the world growing up. And particularly with children in poverty. And then just, you know, I'm fortunate enough not to have any children who are disabled. but seeing these kids who were like really unable to live a normal life get really had their life completely changed just by wheelchair was a pretty incredible impactful situation for me and I mean now as you asked before about where you get fulfillment I mean my wife and I are both fortunate enough now to actually be in a position to donate more money to the charity and you know I raised a ton of money for the charity over the last three or four years so um to see that impact and they brought new leaders in the charity it's now tripled in size in the last um in the last really three or four years i'm not taking credit for that i mean that's really the leadership of the of the charity that's really done that but i think that that's been great to see and that's those types of charities are kind of what really get me interested so your involvement is mostly in fundraising somebody else is running it yes That's correct.

58:12I'm the classic chair board person who tells all the board people, we all need to raise money, we all need to put money in. It's important. Otherwise, it can't function, right? Somebody has to pay for their wheelchairs. Exactly. And it's got to be, I mean, you need a board that's actually involved. There's lots of charities where boards are, people are on the board just purely because it's like prestigious. Vanity. Yes, vanity. Exactly. And this is a smaller charity that is kind of less known than it should be. and so it's definitely not vanity and it's it's something that i just felt passionate about because both my wife and i are both on the board and so we've been involved so you do it together yeah we do it together quite some time and we really are our core contribution really is raising money for the charity because at the end of the day i mean between grants and everything else i mean that's the other big piece is just financial donations from sponsors i bring in a lot of corporate sponsors things like that so so you basically spend also your energy and your time not just your money on the charity yeah i do i mean i spend a lot of time in the actual fundraising process it's not it's not just me writing a check it's me convincing 20 or 30 other people write checks and so it's gotten to the point now where it's you know it starts building momentum on itself and you know hopefully you know once i'm off the board in the future like this can just kind of have the momentum just to become a larger and larger charity.

59:34And how do you see your charitable activities in the future? Would you like to spend more on this one, or would you like to diversify? Again, for example, you sell True Connect tomorrow, and you have more time to think about it. Right. More liquidity, I assume. No, I definitely think I would be more involved in different charities. And I also have other things that I enjoy. I mean, there's certainly some vanity investments out there I'd love to make, But I think on the charity side, I would definitely look to do other things. Because I've been doing this for a while. And I think my wife and I would love to find other things that we could do on the charitable side that are a little bit different.

1:00:09I love how your life seems to have these chapters. There is a tendency to get tired of what you're doing and then you're in something else. I've got to find something new to do. You keep repeating that sort of the whole interview. It is a repetition. I'm ready to do the same thing all over again. I guess something else. right that's i need to suffer some more so i'm gonna suffer some more but i like that i like to live life in chapters and know okay i think this is how you make your life feel longer that you close one chapter you go to the next one you learn again i think it's what you asked me before about like how i started leaving us in banking i think the fact that all the chapters are laid out for you i was like oh i can't live my life that way like i can't someone else's life no it's someone I can't sit here and look forward and be like, even though I'd make a lot of money, being like, all right, I know I'm going to do the exact same thing for the next 30 years.

1:01:01Like I was like, I can't, it's not me. I'd rather wake up and be like, I don't know what I'm doing today, but it's not that. And I know I'm focused on this and trying to build this. And who knows what tomorrow is or next year is. Maybe we still in six months or a year or two years. Who knows? But I think that unknown, I would think for a lot of entrepreneurs, that's what makes it exciting, because there's the unknown. Yeah, absolutely. When everything's laid out for you, it's like, that's boring. Yeah, absolutely. So outside of a business, outside of your team that works for you, how do you choose people you spend time with?

1:01:40Wow. how do I spend and I would say one thing I'm very well aware of is who I don't spend time with probably less so than people like I think everyone spends time with people enjoy being around have fun with and enjoy their company um I think I really in the last five six years I've been really cautious about the old adage like don't waste people waste your time what does that mean for me it means like really I spent a lot of time early in my career putting way too much trust and time into people who didn't deserve it and like I'm really cautious my times at the end of the day I mean to find a resource more valuable at this point than money I think once you get over 50 like what do you have would you give more money to be younger I think the answer is yes um so I think you know it's a finite resource and I waste a lot of time with people I look back on it and it was I learned but I spent a lot of wasted time with people who weren't going to help me get to the next place weren't going to weren't the people I should have involved myself with to kind of evolve my career and I learned a lot from that I think that to me only recently have I come to realization I think it's similar with the hiring thing that kind of blind spot and now that I've admitted that I've got it is to take the time really when I'm assessing a relationship be like all right is this the person that is going to be a good use of my time not that I'm going to get something out of it but more like I don't want to waste time I'm just going to waste my time trying to figure out what they can get from me.

1:03:08How exactly do you measure that? That's a good question. I'm still working on that. I think you can sense it. I mean, I think I've gotten at least you get a certain age where you kind of sense, like, all right, this person. And it really gets on when someone's trying to get something from you. And you know it's not reciprocal. And it can be anything, not just money. But you're just like, all right, I get a sense of where this is headed. I'm out. And I think when I was younger, I always benefited the doubt of, like, oh, well, this person's bringing this opportunity. Even though there's some red flags, I'm going to ignore the red flags because I see the opportunity.

1:03:43And I did a lot of that early in my career. And I think that bled into some personal relationships as well. And I think my wife and I talk about this a fair bit. I'm just like, hey, let's, like, really. I mean, I think, again, when you also have a certain amount of success, like, you need to be careful with the people you surround yourself with. Because at the end of the day, I mean, there are people looking to take advantage because they see you have something, they want it. And they're like, I'll do whatever I can to kind of maneuver my way into your life to get it. And so you just have to be, I think, a lot more cautious.

1:04:16And I think early in my career, that actually helped me now. Because I'm very, very aware of like when I feel like I'm getting a red flag here on kind of what this person's intentions are. Yeah. Very interesting. So you're looking, you're focusing on intentions. because you know my litmus test is whether I left the conversation and I felt inspired or actually during the conversation if I feel inspired that that word works for me in a way it's energy right but it's a particular kind of energy like you want you know to be a better person you want to do more interesting things you want to go and explore something inspiration that's probably a good sign Yeah, but I want this inspiration, right?

1:04:56That they pushed me a little bit somewhere where I feel more excited, more alive. So that's kind of my test for it. But it's very interesting that you're looking at it. No, but I think it's very rational because you're like, okay, what's the intention? Which is beautiful. I think intentions actually is the only thing we can judge. The problem is that we don't necessarily always know the intention of another. Actually, we never know the true intention of another person. we can only guess. But we can't really judge actions because actions can be influenced by so many things outside of our control.

1:05:32For example, for yourself, you can only judge yourself in terms of your intention. Otherwise, it's unfair. I think if you feel like your intentions are on the whole as good as they possibly can be, nobody's perfect. But if you feel like you generally bring good intentions to the table and you sense, I think I've gotten better now and you sense all right these intentions of this person are not good it could be anything I mean I think it's also somewhat geographically based in my opinion because in LA frankly I mean there's a lot of people who just looking to basically try to get one over on you in my opinion just my experience in Los Angeles and so I there are places like that yes there are places like that not just LA it's not just LA it's not just LA it's definitely New York and other cities around the world LA a little more in your face than other places but I think in our experience of living in LA in 20 years, we've run into people who specifically were looking to try to take advantage.

1:06:28And that's probably why you focused on intentions because you were in an environment when people had wrong intentions and then they wasted your time. Yes. But I mean, that's business and personal. It wasn't just one or the other. I mean, so at the end of the day, the only thing I can do is reflect on myself. Like, all right, what am I doing wrong? Because, you know, if their intentions are bad or whatever, like I'm letting that person into my sphere. So it's my fault. so and I think that's one thing I think both my wife and I've learned of a lesson we've learned from LA is on the business side and on the personal side like a willingness of people or actually a desire some people must say just because it's such a strange place in terms of just like I think the industry and everyone kind of being out there to kind of find themselves that I think you know at the end of day you get some people who are desperate and desperate people do desperate things and then you end up in situations where it's like all right how do I get into this situation yeah it certainly has a reputation for people with big egos trying to satisfy those egoistic desires I mean look it's a beautiful city in a beautiful state one of the most beautiful states in the country of course unfortunately I would argue not politically run particularly well but I don't want to get into politics but it's it's unfortunate what's happened in California in the last like 10 years it's really yeah it's really not what it used to be it's kind of sad now you have time in Switzerland that's part of the reason we're there I see it definitely influenced that decision so yeah no Switzerland's an absolutely gorgeous country so Matthew I am conscious of uh the time so I want to ask you my last question okay it's be philosophical get ready i think i need my wife here she's so much better at these questions than i am no i actually really like that now you're alone so you have to stand on your own two feet exactly so how do you want to be remembered wow that is a philosophical question sorry how do you want to be remembered um the only thing you can leave i see some people are exceptions because they have big lives and so their their memories are fame and everything else and kind of what they left behind um i think it's really just you know being someone who's like a very good provider for those around them i would think if you've done that um i think at the end of the day it's like how that touches how many people because i think at At the end of the day, you've got a ripple effect if you've influenced enough people, young, old, in between.

1:09:12And I think that, you know, through my good fortune, I think I've had the luck to do that with a lot of people. And so I think, you know, that at the end of the day, I think can be the best legacy is you've had a positive impact, both directly and indirectly, on prospectively thousands of people. And I think that's the best way to remember. beautiful thank you so much you're welcome that was a fascinating conversation

From the publisher

Matthew Johnson sold his healthcare software company 11 years ago, after leading it through three rounds of fundraising in just three years.


Alongside his twin brother Nathan, he then acquired and transformed TruConnect into a telecom powerhouse. Matthew also co-founded the technology investment bank Drake Star Partners, leveraging his earlier investment banking experience in NYC.


Balancing life between LA and Switzerland, he also leads a nonprofit providing wheelchairs to disabled children. Let’s dive into his unique post-exit lessons on staying motivated, enjoying life, and raising entrepreneurial children.


TIME STAMPS:

00:00:00 - 00:02:34 - Introduction and Career Transition

00:02:34 - 00:03:23 - The First Startup Experience

00:03:23 - 00:06:33 - Building True Connect

00:06:33 - 00:07:50 - Financial Discipline and Management Philosophy

00:07:50 - 00:12:42 - Transitioning from Finance to Entrepreneurship

00:12:42 - 00:15:08 - Balancing Multiple Ventures

00:15:08 - 00:19:05 - Considering Exiting True Connect

00:19:05 - 00:23:28 - Lessons in Hiring and Management

00:23:28 - 00:33:05 - Managing Investments and Personal Fulfilment

00:33:05 - 00:37:21 - Impact of Entrepreneurship on Family and Personal Life

00:37:21 - 00:41:06 - Raising Entrepreneurial Children

00:41:06 - 00:50:02 - Reflecting on Angel Investing

00:50:02 - 00:58:59 - Charity Work and Personal Fulfilment

00:58:59 - 01:08:21 - Life Philosophy and Future Goals

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