Matthew Johnson. Prolific Exited Entrepreneur on Work-Life Balance
Episode - 37
Matthew Johnson. Prolific Exited Entrepreneur on Work-Life Balance
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.
What We Discussed:
00:00:00: Introduction and Matthew Johnson's background
00:00:53: Overview of the episode
00:01:15: Transition from investment banking to healthcare software startup
00:01:49: Motivation behind career change
00:02:28: Financial mindset and risk-taking
00:03:29: Acquisition of TrueConnect
00:06:07: Transition to entrepreneurship
00:07:05: Fixing a financially broken company
00:08:00: Investment without outside capital
00:08:51: Possibility of selling TrueConnect
00:09:35: Other business ventures
00:10:10: Lessons from spreading too thin
00:12:08: Leadership challenges and executive hires
00:14:30: Investment banking and company control
00:15:18: Plans for potential exit
00:16:55: Regulatory challenges in telecommunications industry
00:17:59: Reflections on owning a telecom business
00:18:12: Dealing with government involvement in business
00:19:12: Transition to angel investing
00:21:02: Motivation for becoming an entrepreneur
00:24:03: Personal life and entrepreneurial challenges
00:26:08: The value of freedom in entrepreneurship
00:27:56: Balancing financial freedom and fulfillment
00:31:36: Living between Lugano and LA
00:32:48: Measuring fulfillment in life
00:34:04: Proud accomplishments and supporting family
Sure, here are the chapters extracted from the provided transcription:
00:35:27: Personal reflections on entrepreneurial life
00:36:38: Balancing family and work as an entrepreneur
00:37:29: Thoughts on children's career paths and role modeling
00:38:38: Instilling work ethic and financial responsibility in children
00:42:12: Strategies for wealth management after a business exit
00:46:00: Challenges of repeating entrepreneurial success
00:50:46: Key factors to consider when investing in businesses
00:52:24: Finding the right team and betting on the jockey
00:53:06: Motivation behind continued entrepreneurial endeavors
00:53:25: Challenges in business and the value of a good team
00:54:23: Approach to charity and personal fulfillment
00:55:02: Introduction to Momentum Wheels for Humanity
00:59:07: Fundraising efforts and board involvement
01:00:09: Living life in chapters and evolving careers
01:02:32: The importance of time and cautious relationships
01:08:00: Experiences in LA and Switzerland
01:08:22: How do you want to be remembered?
-
Matthew Johnson: [00:00:00 - 00:00:18]
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 the motivation to go do something very entrepreneurial and really take a lot more risk.
Anastasia Koroleva: [00:00:19 - 00:01:09]
Matthew Johnson. He sold his healthcare software company eleven years ago after leading it through three rounds of fundraising in just three years. Alongside his twin brother Nathan, he then acquired and transformed TrueConnect into a telecom powerhouse. Matthew 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.
Matthew Johnson: [00:01:09 - 00:01:10]
Thank you for having me.
Anastasia Koroleva: [00:01:10 - 00:01:12]
Very exciting to hear your story.
Matthew Johnson: [00:01:13 - 00:01:14]
Looking forward to talking about it.
Anastasia Koroleva: [00:01:15 - 00:01:25]
So Matthew, you had this really successful investment banking career in New York, then you suddenly stopped and moved to LA to join a healthcare software startup, correct?
Matthew Johnson: [00:01:25 - 00:01:25]
That's correct.
Anastasia Koroleva: [00:01:26 - 00:01:28]
I'd love to know why.
Matthew Johnson: [00:01:28 - 00:02:20]
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 in investment banking 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 in 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. 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 and 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.
Anastasia Koroleva: [00:02:21 - 00:02:25]
So you wanted to explore, you wanted a sense of adventure and see what else is out there.
Matthew Johnson: [00:02:25 - 00:02:26]
Correct.
Anastasia Koroleva: [00:02:26 - 00:02:42]
What this life is about. Interesting. It is quite fascinating because most people I talk to, they clearly had a financial motivator in there for a startup by necessity or by other reasons, usually thinking about financial freedom, it was the reverse.
Matthew Johnson: [00:02:42 - 00:02:46]
I had money and I said, let me lose money. Which was the exact opposite.
Anastasia Koroleva: [00:02:46 - 00:02:47]
Exactly.
Matthew Johnson: [00:02:47 - 00:02:55]
And things played out just that way. I started with some money, lost the money, going to a startup, and basically started all over again after that.
Anastasia Koroleva: [00:02:55 - 00:03:03]
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.
Matthew Johnson: [00:03:04 - 00:03:29]
Yes, I 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 both had discussions about, hey, let's do our own thing. We both just happened to be in Los Angeles, and so we made a decision to do something together at that point in time.
Anastasia Koroleva: [00:03:29 - 00:03:35]
Yeah. And then you guys bought into what's now called True Connect.
Matthew Johnson: [00:03:35 - 00:03:36]
Correct.
Anastasia Koroleva: [00:03:36 - 00:03:38]
So tell me more about that.
Matthew Johnson: [00:03:39 - 00:04:52]
I like that expression, bought in. Wow. It's been a journey of highs and lows, is the only way I can describe it. But when we, my brother and I, actually, enough. We had started our own kind of advisory investment banking firm in LA, 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.
Anastasia Koroleva: [00:04:52 - 00:04:56]
Yeah, it's quite impressive. So it took you like 14 years?
Matthew Johnson: [00:04:56 - 00:04:58]
14 years. And we never raised outside capital.
Anastasia Koroleva: [00:04:59 - 00:04:59]
Amazing.
Matthew Johnson: [00:04:59 - 00:05:47]
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 make no mistake, I mean, we may be investment bankers and think we're super smart, but we made every mistake that every entrepreneur makes. I 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.
Anastasia Koroleva: [00:05:47 - 00:06:40]
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. And 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 if you do it the other way around, did you find your mindset, this change in the mindset is challenging for you?
Matthew Johnson: [00:06:40 - 00:07:58]
That's a great question. I don't think I've ever been asked that question before. I think, as we discussed a little bit before, I think my, what was great was the background. Investment banking, I think really helped both because he was in investment banking as well. I think it really helped the way we looked at companies and opportunities because we really looked at it financially first, because we weren't, I mean, Kenley, 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. 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 entering into markets you probably should have entered into. 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. And we've never raised outside capital. 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. Anyone outside the business other than myself and my brother. So.
Anastasia Koroleva: [00:07:58 - 00:07:59]
Because you don't have to.
Matthew Johnson: [00:07:59 - 00:08:00]
Because we don't have to.
Anastasia Koroleva: [00:08:00 - 00:08:03]
I mean, because you structured it, you know, cash flow first.
Matthew Johnson: [00:08:03 - 00:08:50]
We did. I mean, there were three times we had to invest again. Not to sound like everything was perfect with this company. Cause it almost went under in 2009. Obviously, because of the financial crisis, we 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 it 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.
Anastasia Koroleva: [00:08:51 - 00:08:54]
So would you sell that company now?
Matthew Johnson: [00:08:54 - 00:08:55]
Would I?
Anastasia Koroleva: [00:08:55 - 00:08:55]
Yeah.
Matthew Johnson: [00:08:55 - 00:09:33]
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'd mentioned, I. You earn 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 challenging in that respect. So it really is more of niche buyers. And there's a couple issues we're dealing with. 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. And I think my brother and I would, at this point, would be very open to that.
Anastasia Koroleva: [00:09:35 - 00:09:42]
Okay, interesting. So you have this amazing cash flow, you own the business, you have the control, but you still wouldn't mind selling. Why is that?
Matthew Johnson: [00:09:42 - 00:10:20]
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 a company in India, we have a company in China, we have a company in Israel, different companies we've acquired with some of the cash flow. Others we've just spent total startups. 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 what 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.
Anastasia Koroleva: [00:10:21 - 00:10:28]
So would you say you're spreading yourself too thin, or you just have this each again to see what else is out there?
Matthew Johnson: [00:10:28 - 00:10:55]
Well, I think in the past, we definitely spread ourselves too thin, because then, in the past, we were doing, as you mentioned before, we're part owners of an investment bank based out of New York. Now I'm just on the board of that company. I pulled back from that. I was trying to do that and run this business and run other companies we'd 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.
Anastasia Koroleva: [00:10:55 - 00:10:55]
Yeah.
Matthew Johnson: [00:10:55 - 00:11:29]
And I was like, I can do all of this. And he was right. I mean, 2009 happened, and that really opened my eyes up. All right? I can't be trying to run 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 really said about my brother and I in private, 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, okay, it's a big company now. We really need to focus all of our time on this.
Anastasia Koroleva: [00:11:29 - 00:11:34]
So you wouldn't consider hiring a CEO, stepping down, focusing on other things you would prefer to sell?
Matthew Johnson: [00:11:34 - 00:11:50]
Ooh, I don't know if I can answer this question. My brother ever watches this, he knows what I'm thinking right now. We did try twice, okay? And it was a miserable failure. So I'm sure many other people might listen, this will have the exact same experience.
Anastasia Koroleva: [00:11:50 - 00:11:52]
Many people in my audience, yes, you.
Matthew Johnson: [00:11:52 - 00:12:41]
Get a resume, you interview them, you're like this. And look, one of my blind spots, frankly, 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 gonna come in and give it 100%. 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're just kick back, take this big salary, tell everyone else what to do, even though they don't really know what they're doing. And we actually recently had a very bad experience with that in 2022. If those individuals ever watch this, you know who I'm talking about. And it was a mess because I was so excited. It was actually three executives that I brought on and I was very excited and it was a mess. So within twelve months, they're all gone.
Anastasia Koroleva: [00:12:41 - 00:12:43]
You don't want to go through that again.
Matthew Johnson: [00:12:43 - 00:13:35]
No, I just feel at this point we brought in a bunch of new executives, and the new team I have right now is great. Very, very happy with them. But my brother and I think are, I think, similar to many natural owners, 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. Yeah. But I think from my perspective, I think my brother and I would love to be take an exit and really do other things because we have a lot of other interests.
Anastasia Koroleva: [00:13:36 - 00:13:43]
So you also in parallel right run, you know, private equity firm, would that be the right name for?
Matthew Johnson: [00:13:43 - 00:14:32]
It's an investment banking firm that my brother and I are part owners of. 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, try to help as the business is growing. The firm is called Drake Star Partners out of New York. They've got a terrific CEO, 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 Wifi, 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 TrueConnect. Yeah, we're spending 100% of our time on that.
Anastasia Koroleva: [00:14:32 - 00:14:37]
And if you sold true connect, you would probably get more involved in the other ones, correct?
Matthew Johnson: [00:14:37 - 00:14:56]
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. Obviously, you can download it both on iOS as well as on the. Wow. Just totally blanked right there for a second.
Anastasia Koroleva: [00:14:56 - 00:14:58]
Sorry. Android?
Matthew Johnson: [00:14:58 - 00:15:02]
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.
Anastasia Koroleva: [00:15:02 - 00:15:15]
If you sold today, what would you do? Because you obviously had an exit from your healthcare software right now. So you've been in this place now on the personal level. Like, what would you do?
Matthew Johnson: [00:15:15 - 00:16:59]
Well, number one, I would control the exit. So, I mean, I think one of the advantages you'd 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 investment banking, both running a business of the size. So, like, I know the game on how to sell a business. No banker is going to come to my office, like, trick me or convince me to do something I don't want to do, because I understand exactly how it works. I think a lot of individuals who, I mean, obviously not private equity backed, but companies they've built without a 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. How do I understand, you know, 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. So 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, wherever we could buy into something and own it, because I really have no interest in being a minority shareholder in something, and I think the first thing I probably do is buy something that's not regulated because that's one of the big reasons I exit. This business is just so sick of working a regulated market.
Anastasia Koroleva: [00:16:59 - 00:17:01]
It's a barrier to enter for others.
Matthew Johnson: [00:17:01 - 00:17:57]
And it's a psychological abuse you have upon yourself. I mean, it's also being in healthcare or telecommunications or some of these industries that are so highly regulated or aerospace. 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 address that issue in the business? This particular part of the telecommunications industry is very nichey 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. And I know if I were to do another business, I'm not doing that again.
Anastasia Koroleva: [00:17:57 - 00:18:14]
So for sure, I can understand that. I had a telecom business, actually. And at some point I got 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.
Matthew Johnson: [00:18:14 - 00:18:14]
Exactly.
Anastasia Koroleva: [00:18:14 - 00:18:21]
So maybe, maybe you had a similar feeling, and we are control freaks, and sharing control with the government is not necessarily.
Matthew Johnson: [00:18:21 - 00:18:22]
That's your worst partner.
Anastasia Koroleva: [00:18:22 - 00:18:25]
Exactly. We always negotiate with.
Matthew Johnson: [00:18:25 - 00:19:11]
Yes, we always joke in our company. 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, it's. 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. I'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 regulate business after this.
Anastasia Koroleva: [00:19:12 - 00:19:23]
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.
Matthew Johnson: [00:19:25 - 00:20:51]
Interesting. Yeah. As we come in a little bit before, I'm not a huge fan of angel investing. Just interesting things is, again, I did it in reverse. Did a lot of things reverse. I was doing angel investing 20 years ago. Again, the classic angel investing in the west coast of the United States is like 50,000, $100,000, and 1015, 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 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. It doesn't get me excited. Having someone have a great idea, I think is amazing. And there's great angel investors, many who are members of Tiger, somewhere in my group as well. I'm not one of them. I don't, I don't think I made any money. I'm angel investments. I think it was like over 15. So, like, yeah, I'm done with this. 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.
Anastasia Koroleva: [00:20:51 - 00:21:22]
So we talked about how you do things differently from everybody else I talked to in the sense that you are an investor first and an entrepreneur second. So 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?
Matthew Johnson: [00:21:22 - 00:22:46]
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, is 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. And 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 of spin out of I think my desire. The more my partner got more and more involved, the more really enjoyed building the company. Because I do think anyone who is an entrepreneur at heart, I'd like to think I'm more of an entrepreneurial person now than I'm a finance person. I feel like it flipped probably twelve years ago where I really enjoy building things. I don't get as excited about being on the financial side of the business. I 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. So I think that's changed.
Anastasia Koroleva: [00:22:46 - 00:22:51]
Do you think that creative builders gene was always in you or you developed over time?
Matthew Johnson: [00:22:51 - 00:22:57]
I mean, I think it was because I think that's the reason I left investment banking. I think I felt something pulling me.
Anastasia Koroleva: [00:22:58 - 00:22:58]
You were in the wrong place.
Matthew Johnson: [00:22:59 - 00:23:56]
Yeah, I was in the wrong place. And I really saw 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 be like, you're just supposed to do this, you don't need to go beyond that. And I'm like, that's not the way I operate. So I think for me, getting, I mean, for some people who've 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. And so I think, 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 end 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.
Anastasia Koroleva: [00:23:57 - 00:23:59]
We talked about it. An expensive lesson.
Matthew Johnson: [00:23:59 - 00:24:00]
An expensive lesson. Yes.
Anastasia Koroleva: [00:24:01 - 00:24:15]
Yeah, it happens. So on the personal side of things, how does your wife feel about your change from the financial industry into business? Were you married at the time?
Matthew Johnson: [00:24:15 - 00:24:40]
We were. We've married for 21 years. I know the date's better than she does. So this is always a joke. We have no, I think she, I think she's always supported whatever she's seen me do that she knows motivates me. I think one of the things always people talk about, like, with good entrepreneurs, this seems like a kind of classic comment that everyone makes. She's like, you have to have grit, but it's true.
Anastasia Koroleva: [00:24:40 - 00:24:41]
Yep.
Matthew Johnson: [00:24:41 - 00:25:14]
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 in investment 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 proponent, even when we were dating, of, like, want to go do something different? This clearly isn't your thing. And. Cause I mean, even though I was doing it and I enjoyed 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.
Anastasia Koroleva: [00:25:14 - 00:25:15]
Yeah.
Matthew Johnson: [00:25:15 - 00:25:28]
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, we did get married. I mean, basically, I was broke, so I was like, all right, now I have to make money.
Anastasia Koroleva: [00:25:28 - 00:25:38]
So, yeah, entrepreneurs have this crazy rate of divorces because often spouses don't, don't understand why somebody behaves that way.
Matthew Johnson: [00:25:38 - 00:25:41]
Yeah, no, I think, actually, I think she's a psychologist.
Anastasia Koroleva: [00:25:41 - 00:25:43]
Your wife, you're married.
Matthew Johnson: [00:25:44 - 00:26:34]
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 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 think there's a comment that I always read about kind of, you know, what does entrepreneurship or running your business or exiting or whatever do for you. And I think it's true. It's not just about the money. It's not just about the control. It's not about kind of feeling good about yourself. At the end of the day, I think it's the freedom.
Anastasia Koroleva: [00:26:34 - 00:26:35]
Yeah.
Matthew Johnson: [00:26:35 - 00:26:58]
I mean, because the day, the ability to sake, 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. 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.
Anastasia Koroleva: [00:26:58 - 00:27:41]
Yeah. 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. 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 or try to hire someone.
Matthew Johnson: [00:27:41 - 00:27:43]
Thinking about that right now. Nathan, this is. You got this.
Anastasia Koroleva: [00:27:44 - 00:28:08]
Okay? Blame me, Nathan, if I see your own idea into your brother's head, but 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?
Matthew Johnson: [00:28:10 - 00:28:11]
We're getting philosophical now.
Anastasia Koroleva: [00:28:11 - 00:28:16]
And whether you're doing it. Yeah, yeah. Challenge your thinking a bit.
Matthew Johnson: [00:28:16 - 00:29:14]
I mean, it's an interesting question, I think. I think you get over a certain age. I mean, I didn't have an ex at young, so it wasn't like I had some exit. Like, in my early thirties, 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 we'd like to live. But I think from that perspective, I think it's really at the end of day for us. 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. But 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.
Anastasia Koroleva: [00:29:14 - 00:29:15]
Enough of what?
Matthew Johnson: [00:29:15 - 00:29:31]
I don't know if it's gonna 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. Like internally it's. And maybe that's a bigger issue that I need a psychologist for.
Anastasia Koroleva: [00:29:31 - 00:29:33]
But is it? Well, you have one at home.
Matthew Johnson: [00:29:34 - 00:29:35]
She doesn't know how to help me with that issue.
Anastasia Koroleva: [00:29:35 - 00:29:38]
I expect you to be quite psychologically advanced.
Matthew Johnson: [00:29:38 - 00:29:43]
Yes. Well, I mean, she doesn't hate that answer. Probably. She's like, oh, it's not enough. Okay, keep going.
Anastasia Koroleva: [00:29:43 - 00:30:01]
So, okay, 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?
Matthew Johnson: [00:30:01 - 00:30:23]
Yeah, maybe it is. A. The driving source is not feeling like you're enough, so you have to keep doing more to be enough. I 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'd be very hard for me to sell a company and go on the golf course. It's just not my thing. I enjoy golf.
Anastasia Koroleva: [00:30:23 - 00:30:23]
That's fun for you.
Matthew Johnson: [00:30:23 - 00:30:44]
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. Some entrepreneurs, I know a couple that are very happy, they were tired, in their early fifties, 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.
Anastasia Koroleva: [00:30:44 - 00:31:06]
I actually find that for most people, it's just a temporary solution. Yes, because you need to feel your growing. You need to feel you meta, that you're contributing something, and that if you get in recognition back from the society for something valuable, I think we all need that on some genetic level.
Matthew Johnson: [00:31:06 - 00:31:34]
No, I think 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 I think at times I'm like, all right, what would I do after I sold this business? And I don't know that I have a great answer. All I know is I don't think I could just say, all right, let me take 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. So.
Anastasia Koroleva: [00:31:34 - 00:31:36]
Yeah. And do you like that?
Matthew Johnson: [00:31:36 - 00:31:37]
I do like that, yes.
Anastasia Koroleva: [00:31:37 - 00:31:42]
Talking about traveling. So you now basically live between Lugano, Switzerland.
Matthew Johnson: [00:31:42 - 00:31:43]
Correct.
Anastasia Koroleva: [00:31:43 - 00:31:49]
And La, which is very far. You travel once a month back and forth. How does that work as a lifestyle?
Matthew Johnson: [00:31:51 - 00:32:47]
I 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 Matt, 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 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, a luxury that, while challenging, I think I'm very lucky to have.
Anastasia Koroleva: [00:32:48 - 00:32:55]
So if you were to rate your level of fulfillment in life from zero to ten. Oh, yeah.
Matthew Johnson: [00:32:55 - 00:32:58]
I didn't know we were going to these questions.
Anastasia Koroleva: [00:32:58 - 00:32:59]
No, we're good.
Matthew Johnson: [00:32:59 - 00:33:01]
Next one are going to be marriage questions.
Anastasia Koroleva: [00:33:01 - 00:33:04]
So, yeah, it just warming up.
Matthew Johnson: [00:33:04 - 00:33:05]
Yeah. So. Oh, boy.
Anastasia Koroleva: [00:33:06 - 00:33:12]
So on a scale from zero to ten, how fulfilled are you overall in life?
Matthew Johnson: [00:33:14 - 00:33:22]
I would say pretty high. I mean, I think. I would say probably. I don't think anyone can say a ten. I mean, so I'd say probably an eight.
Anastasia Koroleva: [00:33:22 - 00:33:23]
Yeah, that's high.
Matthew Johnson: [00:33:24 - 00:33:31]
Yeah. No, I feel like, I think when, if the people specifically, like, around you are happy.
Anastasia Koroleva: [00:33:32 - 00:33:32]
Mm hmm.
Matthew Johnson: [00:33:32 - 00:33:53]
Like, I, at the end of the day, I've got my sister in law, my, my wife, my kids, got a great lifestyle in Gano, 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.
Anastasia Koroleva: [00:33:54 - 00:33:54]
Yeah.
Matthew Johnson: [00:33:55 - 00:33:58]
And so I think from that perspective, that provides a lot of fulfillment.
Anastasia Koroleva: [00:33:58 - 00:34:04]
Of course, yeah. So you must be proud of your achievement that you could do that.
Matthew Johnson: [00:34:04 - 00:34:14]
Right. And you see the lifestyle you give people and extends. My wife and I support a large part of our families on both sides.
Anastasia Koroleva: [00:34:14 - 00:34:14]
Yeah.
Matthew Johnson: [00:34:15 - 00:34:46]
So 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. Not gonna lie. Sometimes they're like, I'm done doing this. But same time, the ability to do it, I think, makes you feel like, all right is, you know, I think you can't, you can't not help feel like, all right. This great sense of accomplishment with being able to do that.
Anastasia Koroleva: [00:34:46 - 00:35:04]
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 play such a crucial role in the family. That makes a lot of sense. Anything else that feeds that high level of fulfillment for you?
Matthew Johnson: [00:35:06 - 00:35:57]
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, and you see that. You see kind of like, the fortune that I have to have all those things. As 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.
Anastasia Koroleva: [00:35:58 - 00:36:02]
That's brilliant, given that you have to fly back and forth a lot, and.
Matthew Johnson: [00:36:02 - 00:36:37]
This is obviously a little older now. When they were younger and I was, like, working my company, I really made a point of spending a ton of time with my kids. So I feel great that I was able to build something at the same time, not always gone. If I'd stayed invested banking, that would have been travel all the world, gone for weeks, months on end on someone else's schedule. And the ability to have a company still spend a lot of time working on it, but then also having the ability to say, all right, hey, I'm spending this weekend with my kids, and I'm gonna coach little league and do other things like that. And so I leaned into that pretty heavily when they were younger.
Anastasia Koroleva: [00:36:38 - 00:36:51]
And now you're saying that you feel happy, that you avoided that very typical regret of people who stay in investment banking and never have that.
Matthew Johnson: [00:36:51 - 00:37:29]
I hear that a lot from my, I have a lot of friends, banker friends. So I hear a lot that, like, I missed out on my kids growing up. You know, I was working 100 hours a week, you know, someone else's schedule. So, yeah, 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, like, 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 daddy. He was always traveling. He was always working. And so I think that's been, that's been great. I think. I like to think I have a really good relationship with all of them.
Anastasia Koroleva: [00:37:29 - 00:37:36]
So would you like your kids to be entrepreneurs and not do have a corporate job?
Matthew Johnson: [00:37:37 - 00:37:38]
Absolutely.
Anastasia Koroleva: [00:37:38 - 00:37:39]
Okay.
Matthew Johnson: [00:37:39 - 00:38:25]
Yeah. I would never tell them, no. I don't tell them anything. I really don't. I mean, my father didn't. I mean, he was, my father was heterodontology at Johns Hopkins for 20 years, a very accomplished doctor, and he never once had gone to 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. Definitely don't be a lawyer. You can hire those guys. Yeah, exactly. 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, I'd be like, great. Like, let me help you with that.
Anastasia Koroleva: [00:38:25 - 00:38:37]
But do you consciously realize 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?
Matthew Johnson: [00:38:38 - 00:39:13]
Well, I think some of the risk, and I'm sure you experiences 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 I think that's one of the challenges, though, trying to balance out of, like, how do I ingrain in them kind of the work ethic while also providing them with kind of a unique situation where they have some financial stability at a very young age. And so it's a difficult.
Anastasia Koroleva: [00:39:13 - 00:39:17]
How do you go about it? Because there are two schools of thought.
Matthew Johnson: [00:39:17 - 00:39:19]
Really give it all away, like Warren.
Anastasia Koroleva: [00:39:19 - 00:39:42]
Buffet or, yeah, either you bring the children in and you train them to manage wealth and you're very open about everything, right? Or you say, no, you guys need to be hungry. I'm not giving you anything. So you make your own mistakes. You're driven to, you need to build your, your wealth yourself. So in that spectrum, where are you in your thinking?
Matthew Johnson: [00:39:43 - 00:41:12]
I think, I mean, I think, I believe I'm probably in the middle because I think it's a little bit of both. I 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, to go to school in Switzerland and do things like that, but those are more experiential. They're nothing, 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, 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, that, and I think I learned that as well for 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'd be nice if I got older, if I had more money that I could spend. So 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 of 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've exited and things like that to really build a relationship with the money at a very early age so you don't do dumb things with it, like get inheritance and go out and buy a Bugatti or something idiotic like that.
Anastasia Koroleva: [00:41:13 - 00:41:19]
Yeah. And there's a big trend now of second generation giving money away, and they mean very well.
Matthew Johnson: [00:41:19 - 00:41:19]
Yes.
Anastasia Koroleva: [00:41:20 - 00:41:28]
They don't necessarily have the financial discipline and understanding how to do it right. It's a huge demand.
Matthew Johnson: [00:41:28 - 00:42:09]
I'm gonna forget the, I know everyone's heard this one. Forget the old concept of, you know, poor man. I'm not gonna 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, because people just find a way just to blow the money in kind of the second and third generation. So I think we're trying to show them how to invest long term and 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.
Anastasia Koroleva: [00:42:12 - 00:42:36]
So if we go, 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.
Matthew Johnson: [00:42:38 - 00:42:45]
Well, I would cover the little bit. I don't know if I've been that successful, but there's definitely been some really bad misses.
Anastasia Koroleva: [00:42:47 - 00:42:48]
But you've learned your lessons.
Matthew Johnson: [00:42:48 - 00:42:52]
Yeah, that's what I'm offering, some lessons. The hard way. I mean, losing money is the best way to learn a lesson.
Anastasia Koroleva: [00:42:52 - 00:42:53]
Exactly.
Matthew Johnson: [00:42:53 - 00:43:13]
But I do think that people have, like, exited business, and then it's, I think it's different strokes for different folks. The old expression of just kind of like, if you're really good at, like, building a business, I think trying to go from that to basically investing in business to try acquire business, I think that's just a total different skill set.
Anastasia Koroleva: [00:43:13 - 00:43:14]
Exactly. It's very hard.
Matthew Johnson: [00:43:14 - 00:44:02]
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 the financial background, actually acquire my first couple businesses I like to think that question asked before, they're actually going to reverse that in the last 15 to 20 years. So 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.
Anastasia Koroleva: [00:44:02 - 00:45:01]
Lots 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, and that 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 and 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 are too arrogant, right? So that is by far number one mistake, because it just eats so much money so fast, and it's very hard to stop. Right. To get out of it. 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.
Matthew Johnson: [00:45:02 - 00:45:02]
Yes.
Anastasia Koroleva: [00:45:02 - 00:45:11]
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.
Matthew Johnson: [00:45:12 - 00:45:27]
Well, it depends on the business. I mean, also the industry, I'm. Plenty of people have gotten very. I mean, I think it's also timing, too. I mean, you've had some exits very young, you've made a lot of money. And I think those who have experiences, you're like, oh, this is gonna happen every time.
Anastasia Koroleva: [00:45:27 - 00:45:27]
Exactly.
Matthew Johnson: [00:45:28 - 00:46:16]
And the fact of the matter is, with a lot of entrepreneurs, lightning only strikes once. So the reality is a lot of people only have one great exit, and then they think it's gonna happen over and over again, and it just doesn't. And one great exit's all you need. Frankly, I think the perception that you can automatically multiply that because you're successful once, I mean, it's unusual for that to happen unless you're someone like Elon Musk or something like that, who's truly kind of broken the mold in terms of being just a repetitive entrepreneur with a high level of success. I 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.
Anastasia Koroleva: [00:46:16 - 00:46:19]
Well, even in software business, it's a whole world.
Matthew Johnson: [00:46:19 - 00:46:58]
It's its own world within the niche of software whatever. It's like SaaS. And you're saying, all right, like, if I'm an investor in other business, it's going to be in the exact vertical that I play it 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. I 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. A lot of them don't have the grit to, if you want to be a successful entrepreneur, you have to suffer.
Anastasia Koroleva: [00:46:58 - 00:47:01]
Yeah, yeah, that sounds like you have to suffer.
Matthew Johnson: [00:47:01 - 00:47:36]
And that is true. Like, I mean, I think, but it's true. 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 Stanford grads was like, you guys had it too easy. You guys really have never suffered. Like, you've got full paid tuition, your parents paid for everything. You've gone to Pasha school. You're gonna make $200,000 a year leaving the school. You've never really suffered. And so I think that is very true in terms of being able to really be successful. Like, a willingness to take on that suffering and power through it.
Anastasia Koroleva: [00:47:36 - 00:47:42]
Well, but this is exactly what Exeter founders hope to avoid by buying stakes in other businesses.
Matthew Johnson: [00:47:42 - 00:48:02]
The problem is you, quite often, you're gonna invest in that person who's not willing to suffer because you're gonna think, oh, this person's like me. They're gonna, no matter what, they will make this successful. The idea is great. They're smart. They want the name, the school. You know, I'm gonna make a gazillion dollars with this person because they have what I had.
Anastasia Koroleva: [00:48:02 - 00:48:02]
Yeah.
Matthew Johnson: [00:48:02 - 00:48:12]
And the fact of matter is, like, you can't, you can't figure out whether they have what you have until you see them do it. And I've seen a lot of how.
Anastasia Koroleva: [00:48:12 - 00:48:15]
Do you avoid this mistake? Because now you have a lot of experience.
Matthew Johnson: [00:48:15 - 00:48:39]
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 psychologist, I should invite her to every interview because, you know, her instincts always like, don't hire that person or don't do that investment. And I'll do it anyway. And I'll be wrong.
Anastasia Koroleva: [00:48:39 - 00:48:40]
Yeah.
Matthew Johnson: [00:48:40 - 00:48:41]
I'll be like, oh, man, I should have listened.
Anastasia Koroleva: [00:48:41 - 00:48:42]
I told you so.
Matthew Johnson: [00:48:42 - 00:48:47]
Yeah, totally. So, so if you have a wife, like my wife, just take her to her meeting and she'll say yes. No, yes.
Anastasia Koroleva: [00:48:47 - 00:48:47]
Perfect.
Matthew Johnson: [00:48:48 - 00:48:53]
But not even has a secret weapon. Yeah, but you have to listen to them. So let's learn by mistake.
Anastasia Koroleva: [00:48:53 - 00:48:55]
You have a secret weapon, but you're not using it.
Matthew Johnson: [00:48:55 - 00:49:25]
Yeah, I haven't been using, 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. And the reality 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.
Anastasia Koroleva: [00:49:25 - 00:49:25]
Yeah.
Matthew Johnson: [00:49:25 - 00:49:36]
I was like, 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 twelve months.
Anastasia Koroleva: [00:49:36 - 00:49:40]
So why do you keep doing it, though? Are there ways to invest money?
Matthew Johnson: [00:49:41 - 00:50:19]
You get something for punishment. Maybe that's it. I mean, in this case, because I mentioned a comment before, by being an angel investor, I hated, for me, doing the little tiny investments where you own very little of a lot and they all fail is no fun. In this case, it was something was kind of a passion project. We had majority control of the structure we put in place, so we felt like, oh, this is a good bet. We're excited. We love the idea, we love the team. And it 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.
Anastasia Koroleva: [00:50:19 - 00:50:25]
Okay, so any other advice or guidelines besides listen to your intuition and intuition?
Matthew Johnson: [00:50:25 - 00:50:27]
Everyone always says that, that's terrible advice.
Anastasia Koroleva: [00:50:28 - 00:50:36]
Do you have, do you have a criteria that's objective when you choose your, your portfolio companies or you really think.
Matthew Johnson: [00:50:36 - 00:50:43]
It doesn't matter, I mean, objective in terms of industry or what's the criteria?
Anastasia Koroleva: [00:50:43 - 00:50:46]
I mean, for me, the revenue, the margin.
Matthew Johnson: [00:50:46 - 00:51:00]
Yeah. I think you talked about like, how an entrepreneur, someone not like me, who'd 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.
Anastasia Koroleva: [00:51:00 - 00:51:04]
That's exactly why I'm asking you that question, because you're a very unique expert.
Matthew Johnson: [00:51:04 - 00:52:08]
For me. Yeah, it's a very different philosophy for me. Like, I think for me, like, I'm very industry agnostic. It's more the opportunity. So it's the exact opposite advice. What I just gave you for someone who came from that industry, like, 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? Because there's always something broken. We've got an opportunity to invest in a company because I don't like to do startups, except for this one example I just gave you. And now you know why I don't like to do them. Number three is, at the end of the day, you've got to find a way to really vet the team that's going to run it. Because it's always the expression of 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. You've always got to bet on the person who's running that business, 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 and solve towards whatever, as.
Anastasia Koroleva: [00:52:08 - 00:52:10]
Long as they have the gene for suffering.
Matthew Johnson: [00:52:10 - 00:52:31]
Yeah, I mean, but I think those would go together. I think when you find a really talented entrepreneur, they've got that 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. Now, finding those people is hard because you really have to see them execute and you're gonna see them executed once you put your money in.
Anastasia Koroleva: [00:52:31 - 00:52:31]
Exactly.
Matthew Johnson: [00:52:31 - 00:52:33]
So that's the trade off.
Anastasia Koroleva: [00:52:33 - 00:52:34]
Otherwise there's no transparency.
Matthew Johnson: [00:52:34 - 00:53:04]
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 skillset, 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. You gotta be like, all right, let me think financially first, and then about the entrepreneurial opportunity.
Anastasia Koroleva: [00:53:06 - 00:53:13]
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.
Matthew Johnson: [00:53:13 - 00:53:13]
Right.
Anastasia Koroleva: [00:53:14 - 00:53:28]
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.
Matthew Johnson: [00:53:28 - 00:53:42]
But I love doing. Hmm. My executive team are watching, laughing. Cause we always joke about, and it's just the regulations make this somewhat painful. As I said before, I think it's more the love of building something.
Anastasia Koroleva: [00:53:42 - 00:53:45]
Yeah. So building anything. So it doesn't have to be this business.
Matthew Johnson: [00:53:46 - 00:53:50]
But I think when you've got a good team and you see it. Me, you've seen it.
Anastasia Koroleva: [00:53:50 - 00:53:50]
Yeah.
Matthew Johnson: [00:53:50 - 00:53:51]
When you've got a good team, it's fun.
Anastasia Koroleva: [00:53:51 - 00:53:52]
It's fun.
Matthew Johnson: [00:53:53 - 00:54:22]
Everyone really rallies around the strategic vision. Everyone gets excited about 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 that iterative process of building something for me, and perhaps for you, is what gets me excited. Just giving someone money and saying, I hope this works, doesn't get me excited at all.
Anastasia Koroleva: [00:54:23 - 00:54:54]
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 the 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 the charity giving wheelchairs to impoverished children. So tell me more about it. What's in it for you?
Matthew Johnson: [00:54:54 - 00:58:06]
What's in it for me? Absolutely nothing. No, it's called. It'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 for a long time involved in the company, and 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 like come to a meeting. I think you'd like this. At the time, frankly, most of our tourists don't have time for charities. Like, I am the charity. I'm a charity case. I have no money. I'm broke. I have no money to give away. Well, think about it in the future. And so he got me involved in this charity quite a long time ago. And then I suddenly 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 his 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 earlier videos were, like, really hard to watch because you're seeing how some of these children are living, unable to move, and you saw the impact of what this had on these kids having an actual wheelchair and be able to move and go to school, being an active person in the society that they live in, you know, 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, if 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. I think it was like, like $0.90 in the dollar was, like, reaching and delivering 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 love, because I traveled over the world growing up. I've seen a lot of poverty in the world growing up, and particular children in poverty, and then just, you know, fortunate not to have. Unfortunate enough not to have any children who are disabled. But seeing these kids who are, like, really unable to live a normal life get really Heather knife completely changed just by wheelchair was a pretty incredible, impactful situation for me. And, I mean, now, as you asked before about where you guess you get to film. 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 to see that impact. And they brought new leaders in the charity. It's now tripled in size in the last, really three or four years. I'm not taking credit for that. I mean, that's really the leadership of the charity that's really done that. But I think that's been great to see. And those types of charities are kind of what really get me interested.
Anastasia Koroleva: [00:58:07 - 00:58:11]
So your involvement is mostly in fundraising? Somebody else's is running it?
Matthew Johnson: [00:58:11 - 00:58:19]
Yes, correct. I'm the classic chair for a board person who tells all the board people, we all need to raise money, we only to put money in.
Anastasia Koroleva: [00:58:19 - 00:58:24]
And so it's important, otherwise it can't function. Right. Somebody has to pay for the wheelchairs.
Matthew Johnson: [00:58:24 - 00:58:32]
Exactly. And it's got to be. I mean, you need a board that's actually involved lots of charities, reports or people on the board, just purely because it's, like, prestigious.
Anastasia Koroleva: [00:58:32 - 00:58:33]
Yeah, vanity.
Matthew Johnson: [00:58:33 - 00:58:49]
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 something that I just felt passionate about. Both my wife and I are both on the board, and so we've been involved.
Anastasia Koroleva: [00:58:49 - 00:58:49]
So you do it together?
Matthew Johnson: [00:58:49 - 00:59:07]
Yeah, do it together for quite some time. And really our core contribution really is raising money for the charity, because at the end of day, I mean, between grants, everything else, I mean, that's the other big piece, just financial donations from sponsors. I bring a lot of corporate sponsors, things like that.
Anastasia Koroleva: [00:59:08 - 00:59:12]
So you basically spend also your energy and your time, not just your money, on the check.
Matthew Johnson: [00:59:12 - 00:59:34]
I do. I mean, I spend a lot of time in the actual fundraising process. It's not just me writing a check, it's me convincing 20 or 30 other people to write checks. And so it's gotten to the point now where it's, you know, it starts building momentum on itself. And hopefully, once I'm off the board in the future, this can just kind of have the momentum just to become a larger and larger charity.
Anastasia Koroleva: [00:59:34 - 00:59:49]
And 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 through connect tomorrow and you have more time to think about it. More liquidity, I assume.
Matthew Johnson: [00:59:49 - 01:00:08]
No, I definitely think I would be more involved in different charities. I also have other things that I enjoy, and, I mean, there's certain some vanity investments out there I'd love to make, but I think 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.
Anastasia Koroleva: [01:00:09 - 01:00:23]
I love how your life seemed to have these chapters. There is a tendency to get tired of what you're doing, and then you're in something else. I gotta find something new today. You keep repeating that through the whole interview. You were ready.
Matthew Johnson: [01:00:23 - 01:00:25]
I'm ready to do the same thing all over again.
Anastasia Koroleva: [01:00:25 - 01:00:28]
So I guess something else. Right.
Matthew Johnson: [01:00:28 - 01:00:30]
I need to suffer some more, so I'm gonna suffer some more.
Anastasia Koroleva: [01:00:30 - 01:00:41]
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.
Matthew Johnson: [01:00:41 - 01:00:50]
I think it's what you had asked me before about, like, how did I start leaving Austin banking. And I think the fact that all the chapters were laid out for you, I was like, oh, I can't live my life that way.
Anastasia Koroleva: [01:00:51 - 01:00:52]
It's someone else's life.
Matthew Johnson: [01:00:52 - 01:01:00]
No, it's someone else. 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 gonna do the exact same thing for the next 30 years.
Anastasia Koroleva: [01:01:00 - 01:01:01]
Yeah.
Matthew Johnson: [01:01:01 - 01:01:03]
Like, I was like, I can't. It's not me.
Anastasia Koroleva: [01:01:03 - 01:01:03]
Yeah.
Matthew Johnson: [01:01:03 - 01:01:09]
I'd rather wake up and be like, I don't know what I'm doing today, but it's not that.
Anastasia Koroleva: [01:01:09 - 01:01:09]
Yeah.
Matthew Johnson: [01:01:09 - 01:01:12]
And I know I'm focused on this and trying to build this.
Anastasia Koroleva: [01:01:12 - 01:01:12]
Yeah.
Matthew Johnson: [01:01:12 - 01:01:26]
And who knows what tomorrow is or next year is? Maybe we sell in six months or a year or two years. Who knows? But I think that unknown, I would think, for a lot of entourage, that's what makes it exciting, because there's the unknown.
Anastasia Koroleva: [01:01:26 - 01:01:27]
Yeah, absolutely.
Matthew Johnson: [01:01:27 - 01:01:30]
Everything's laid out for you. It's like, that's boring.
Anastasia Koroleva: [01:01:30 - 01:01:39]
Yeah, absolutely. So outside of a business, outside of your team that works for you, how do you choose people you spend time with?
Matthew Johnson: [01:01:40 - 01:02:03]
Wow. How do I spend? I would say one thing I'm very well aware of is who I don't spend time with, probably less so than people mad. I think everyone spends time with people they enjoy being around, have fun with, and enjoy their company. I think I really, in the last five, six years have been really cautious about the old adage of don't waste people, waste your time.
Anastasia Koroleva: [01:02:05 - 01:02:06]
What does that mean for me?
Matthew Johnson: [01:02:06 - 01:03:08]
It means, like, really, I spent a lot of time early my career putting way too much trust and time into people who didn't deserve it. And, like, I'm really cautious of my time 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. 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 I learned, but I spent a lot of wasted time with people who weren't gonna help me get to the next place, weren't the people I should have involved myself with to kind of evolve my career. And I learned a lot from that. And 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 a person that is gonna be a good use of my time? Not that I'm gonna get something out of it, but more like, I don't wanna waste time when someone's gonna waste my time, like, trying to figure out what they can get from me.
Anastasia Koroleva: [01:03:08 - 01:03:10]
How exactly do you measure that?
Matthew Johnson: [01:03:11 - 01:04:26]
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 kinda sense, like, all right, this person. And it really gets down. Like, when someone's trying to get something, you. And, like, you know, it's not reciprocal. And it could be anything, not just money, but you're just like, all right, like, I get a sense of where this is headed. I'm out. And I think when I was younger, it always benefit the doubt of, like, oh, this person's bringing this opportunity. Even though there's some red flags, I'm gonna order the red flags. Cause I see the opportunity. And 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 of 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. 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.
Anastasia Koroleva: [01:04:26 - 01:04:52]
Yeah. So, 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 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.
Matthew Johnson: [01:04:53 - 01:04:54]
That'S probably a good design.
Anastasia Koroleva: [01:04:54 - 01:05:01]
But I want this inspiration. Right. That they, they pushed me a little bit somewhere where I feel more excited, more alike.
Matthew Johnson: [01:05:01 - 01:05:02]
Interesting.
Anastasia Koroleva: [01:05:03 - 01:05:39]
So that's kind of my test for it. But it's very much looking at. No, but I think. 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. But, like, for example, for yourself, you can only judge yourself in terms of your intention. Otherwise, it's unfair to.
Matthew Johnson: [01:05:39 - 01:06:11]
Well, I think if you feel like your intentions are, on the whole, as good as they possibly can be, and nobody's perfect. But if you feel like you generally bring good intentions to the table and you sense, then I think I've gotten better now, and you sense intentions. 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.
Anastasia Koroleva: [01:06:11 - 01:06:12]
There are places like that?
Matthew Johnson: [01:06:12 - 01:06:13]
Yes, there are places like that.
Anastasia Koroleva: [01:06:13 - 01:06:14]
Not just LA.
Matthew Johnson: [01:06:15 - 01:06:28]
Not just LA. Southeast New York and other cities around the world. La, a little more in your face than other places. But I think our experience of living in LA in 20 years we've run into people who specifically were looking to try to take advantage.
Anastasia Koroleva: [01:06:28 - 01:06:35]
And that's probably why you're focused on intentions, because you were in an environment when people had wrong intentions and then they wasted your time.
Matthew Johnson: [01:06:35 - 01:07:23]
Yes, but that was 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 am 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 have learned. A lesson we've learned from LA is on the business side and on the personal side, a willingness of people or actually desire some people in Los Angeles, 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?
Anastasia Koroleva: [01:07:24 - 01:07:31]
Yeah, it certainly has a reputation for people with big egos trying to satisfy those egoistic desires.
Matthew Johnson: [01:07:31 - 01:07:52]
It does. I mean, look, it's a beautiful city and 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 unfortunate what's happened in California in the last ten years. It's really. Yeah, it's really not what it used to be. It was kind of sad.
Anastasia Koroleva: [01:07:52 - 01:07:54]
Now you have time in Switzerland.
Matthew Johnson: [01:07:55 - 01:07:57]
That's part of the reason we're there.
Anastasia Koroleva: [01:07:57 - 01:07:58]
I see.
Matthew Johnson: [01:07:58 - 01:08:03]
They would definitely influence that decision. So, yeah, Switzerland's an absolutely gorgeous country.
Anastasia Koroleva: [01:08:04 - 01:08:10]
So, Matthew, I am conscious of the time, so I want to ask you my last question.
Matthew Johnson: [01:08:10 - 01:08:10]
Okay.
Anastasia Koroleva: [01:08:10 - 01:08:12]
It's gonna be philosophical. Get ready.
Matthew Johnson: [01:08:13 - 01:08:16]
I think I need my wife here. She's so much better at these questions than I am.
Anastasia Koroleva: [01:08:16 - 01:08:21]
I actually really like that. Now you're alone, so you have to stand on your own, too. Good.
Matthew Johnson: [01:08:21 - 01:08:22]
Exactly.
Anastasia Koroleva: [01:08:22 - 01:08:24]
So how do you want to be remembered?
Matthew Johnson: [01:08:25 - 01:08:28]
Wow. That is a philosophical question.
Anastasia Koroleva: [01:08:28 - 01:08:28]
Sorry.
Matthew Johnson: [01:08:28 - 01:09:34]
How do you want to be remembered? The only thing you can leave. I see some people are exceptions because they have big lives and so their memories, their fame and everything else and kind of what they left behind, I think it's really just, you know, being someone who's, like a very good provider for those around them. I think if you've done that, I think at the end of day, it's like how that touches how many people? Because I think at the end of day, you've got a ripple effect if you've influenced enough people, young, old, in between. And 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 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 it.
Anastasia Koroleva: [01:09:35 - 01:09:38]
Beautiful. Thank you so much.
Matthew Johnson: [01:09:38 - 01:09:39]
You're welcome.
Anastasia Koroleva: [01:09:39 - 01:09:39]
That was a fascinating.