The Dark Side Of The Startup World | John Roa | Modern Wisdom Podcast 242

1. 0:00 – 15:00

   At some point, it's…

   1. JRJohn Roa0:00

      At some point, it's just insane what's going on. And what we don't talk about is the downside of all that, of how the entrepreneurs who are taking these bets and running these companies are struggling. And the, the s- statistics around this are haunting. The entrepreneurs of today in kind of this high growth world have 60% more mental health issues than the average public. This is, um, in America. Um, eight times the rate of bipolar, six times depression, four times suicide, four times substance abuse. We are melting down (laughs) as the kind of race horses behind these companies, yet we don't ever hear that story until, until it's a, a horrific headline, like the Aaron Swartzs of the world and, and other folks who have even taken their own lives when they can't handle the pressure.

   2. CWChris Williamson0:42

      For the people who are listening that don't know who you are, what's your background? How did you end up speaking to me here?

   3. JRJohn Roa0:50

      Yeah. So I'm a, I'm a pretty lifer entrepreneur. Um, I've been in the tech world since I was technically 11 years old when I learned to program, you know, code, hack, game, build computers. And then s- my first company I started when I was 14, so I'm now 36, so you know, two thirds of my life almost I've been running tech companies. And it's just been, you know, uh, goes without saying, a passion of mine, um, forever. And you know, kind of before it was en vogue like it is today, um, I really just had a knack for computers, an interest in being a self-starter and being an entrepreneur, even though I really didn't know that's what I was for a lot of that time. And, um, you know, that journey led to a number of tough lessons, you know, a lot of early failures, all the stuff that you generally hear about when people go through a lifetime of entrepreneurship. And then when I was 26, so 10 years ago, I was in Chicago and, um, was kind of down on my (laughs) , on my luck. It was not a great time personally and professionally. Um, it was in the midst of the r- the recession, you know, globally, but obviously, you know, a lot of that was happening here in the US. Uh, I was out of work, my parents were out of work, um, the family wasn't doing great, and I was not really, uh, you know, present with a lot of options on what to do to kind of get my life back in order. And in the way I saw it, I could either continue to persist trying to make something work that I could self-generate or go get a job and probably work some crappy role for a number of years and try to, you know, get out of debt and those kind of things. So of course, I did the entrepreneurial thing and I created a company called Okta. And, um, you know, for those of, of listeners that might know a company called IDEO, that's the best way to describe Okta, is that we were an innovation and design consultancy. And, and companies like IDEO have been around for decades and they've been helping everybody in the world design and innovate on amazing stuff. And I kind of figured there's a room in the market for a pure play digital version of that. 'Cause the ideas of the world were all kind of old industrial designers and print designers who had kind of moved to digital somewhat begrudgingly, and I figured if we had a team of kind of thrifty digital only innovation folks that we could succeed in that market. And that's what we did. Um, created the company in 2010, uh, bootstrapped, no investors, no partners, no investor, no anything. I mean, no board, no mentors, (laughs) like truly a one man band. And just kind of right place, right time, lot of luck, perseverance, you know, good fortune, grinding, and two years later it was the single fastest growing, uh, innovation and UX agency in America, uh, one of the fastest growing companies of any kind in America. Um, two years after that, we had acquired companies, we were growing nationally and internationally, um, we were doing work for incredible companies, you know, our clients were BMW and United Airlines and others. Um, and ultimately, um, it was the epitome of that entrepreneurial success story, kind of that just like grind it out till it works kind of thing. And then, you know, we were making money, I'm, I'm, (laughs) I'm doing TED Talks and being photographed for magazine covers, it was kind of this very glamorous success story on one side. On the other side is, it's this, is what no one knew what was going on, which is also a classic story that I was really struggling personally, uh, I didn't know how to handle the risk and stress and pressure that I was enduring. I didn't have a lot of healthy, uh, mechanisms for any kind of support. And, um, and I started to struggle, I mean, at a, at a, at a worse and worse level throughout those, uh, those years, um, really deep kind of mental illness and mental, uh, episodes of depression, anxiety, those kind of things, as I was dealing with the, the company. Um, it then turned into a life of kind of excess and partying and substance abuse and all the things that kind of come along with trying to balance out this incredibly kind of ferocious lifestyle. And so in our fourth year, um, it all, (laughs) it all collided with itself and, and that took the form of a pretty severe mental breakdown. Um, I ended up in the hospital, suffered dissociative amnesia, didn't know who or, or who I was, where I was, um, had no recollection of any part of my life, couldn't even tell you my own name. And was in a hospital in that state for a number of days. Um, they weren't sure if I would come back, if, what state I'd be in, if my brain would ever fully recover. It was a very scary time in my life. And this is all still when the company is, you know, quote unquote crushing it in the public world.

   4. CWChris Williamson5:21

      (laughs)

   5. JRJohn Roa5:22

      And, um-And, uh, no one knew except one person at the company. My parents didn't know, my, my siblings didn't know, no one knew. I hid it from everybody, got back to work whenever I was released from the hospital and, and it changed my perspective on what was important because I kind of realized that I was literally trading my life and safety and sanity for this business, which is a ridiculous thing to do. And so I said, "We, we have to end this before it ends me." And, um, I went and, and hired an investment bank, we ran a managed auction and very fortunately sold that business outright to Salesforce, um, it's the biggest company in San Francisco, abou- about a y- about a little under a year after that whole episode. And, um, obviously a very fortuitous exit. I- it was the best case, you know, best result I could've ever asked for given (laughs) how bad the journey had gone for me personally, but how good it had gone for the company. And it really just changed my perspective about everything. It changed how I think about success, what is success, it changes how I think about, um, what, you know, what risk is, is worth risking and, and what parts of our lives we should be betting on and trading for that chance at success. Um, it's changed my perception on what matters in life going forward. It was a pretty wild journey, um, that all happened five years ago. And so in the last five years, I, I've actually been on your side of the world, Chris, I lived in London for half the year each year and then in Greece the other half of the year. So, I was doing very little except enjoying life and just trying to reset after what I had endured and, and ultimately, you know, trying to ph- reframe what it all meant. And, um, the way I found to do that was to write a book about it. And so the book that you previously referenced, it's called A Practical Way to Get Rich and Die Trying, is my memoir. A- and it's everything I just shared in excruciating detail, (laughs) uh, may- maybe, maybe too much detail in some parts, um, but I wanted to get across the real story that we, we don't often talk about, people are s- are, are rightfully afraid to talk about, um, and I'm in a position now where I can do it and I can facilitate more of that. And so that was the point of the book and it came out a little over a month ago now, and it's been going great. So it's, it's exciting. Yeah.

   6. CWChris Williamson7:31

      What a journey, man. Congratulations-

   7. JRJohn Roa7:33

      Yeah.

   8. CWChris Williamson7:33

      ... it really, it really-

   9. JRJohn Roa7:34

      Thank you.

   10. CWChris Williamson7:34

       ... sounds like you're in a significantly better, more awakened, more aligned position than you were.

   11. JRJohn Roa7:42

       To say the least. (laughs)

   12. CWChris Williamson7:44

       (laughs)

   13. JRJohn Roa7:44

       Yes. It's, uh, you know, it's, um, it, it's difficult to describe how different, because, you know, I think that there's this, this, this ill-conceived notion that we change as people. I don't believe that's true at all and, and most, most people smarter than me don't believe it either, is that but we can ch- what I, what can change is our mindset, our priorities, those kind of things. I was always the same person, I just had totally lost the sense of what matters and what's worth it and what risk is and how to manage myself. And so I've done a excruciating amount of work in the last five years to recover from all of that, you know, mostly mentally, but also physically. Um, but yes, it, it is a very different place and mindset today, thankfully.

   14. CWChris Williamson8:24

       Yeah, very thankfully. I don't know how much longer you would have been able to keep going like that. Why do you think... so obviously you, you're talking about this incredible success that you had with your company, very, very fast growing in, you know, I mean 2010, the early 2010s, that period was, I would imagine, incredibly competitive for tech companies, um-

   15. JRJohn Roa8:45

       Yeah.

   16. CWChris Williamson8:45

       ... perhaps even more so than now in that a lot of the low-hanging fruit and a lot of that first mover advantage has probably gone from back then. So why do you think-

   17. JRJohn Roa8:55

       Yeah.

   18. CWChris Williamson8:55

       ... that you had any success in business? You mentioned about work rate and timing and stuff. Could you dig into that a little bit?

   19. JRJohn Roa9:03

       Definitely. So the one thing that we did that was most intelligent that we did not realize we were doing, (laughs) um, was being a support structure to that tailwind that you're talking about. You know, the, this is the era when all of these now multi-billion dollar tech companies were coming out, the Ubers of the world and everybody else. Um, and we were designed to be an agency for those companies. So we were here to help them design beautiful products, to understand their customers better, to innovate, et cetera. And so our entire set of clients at the beginning of Okta were other startups. And so they were normally pretty well-funded, they normally needed a lot of help, they couldn't hire fast enough, they couldn't have the disciplines that we did. So we were a support structure to that movement. And so we supplemented it instead of getting caught in the competitive wave, which was fortuitous. Uh, I, I will not pretend to say that was some man- you know, some grand plan that we had concocted, (laughs) that's just the way it worked. And, but the second thing is, is that... I, I made... it's funny, I actually have the Apple presentation on in my other s- monitor here because they're, they're, they just, uh, debuted the 5G iPhone. Um, but Apple had done us a tremendous favor and that was releasing the iPhone and then the iPad right in that generation. And what Apple did... because the iPhone was in 2007, and so we had come off a couple years of being introduced to what great digital design is, because until the iPhone, we had our BlackBerrys and we had our PalmPilots and we had our Microsoft devices and they were perfectly usable. There was nothing wrong with any of the devices and they did functionally what we all need a device to do. At the time it could send a text message and an email, you could surf the web, you could listen to music. It, it did not... you know, the iPhone did not actually perform a single function that those phones did not perform. What Apple did and what they continued to do and what they're doing as we speak, and it's on their monitor, is to understand us, their customers, frankly better than we understand ourselves. And they have an incredible ability to kind of crystal ball into the future of market needs, but also into our psyches. And they understand our behaviors, our, our media consumption patterns way better than we do. And if you remember when the i- when the iPad was debuted in 2011, everyone made fun of it. They're like, "Why do we need this big fucking iPhone?" Right? Like, and there was, like, these memes, people holding the iPad to their head, like it was a joke.And, and now, it's, you know, it's (laughs) revolutionized the industry and changed everything. And so Apple, this is their ability, this is why they're a trillion doll- you know, now a multi-trillion dollar company, this is their, their magic. And companies, a lot of companies, started to realize that if they could do some of that, if they could lead with design and innovation and user experience and user needs and heuristics and all of those aspects, they could also create a competitive advantage like Apple. And so that's what we basically did. W- we would go to companies and we would say, "Hiring us or hiring Okta is kind of like if you could hire Apple to build your product for you," which, you know, you can't do, but if you could, that's kind of like hiring us. And so we had this tailwind in two capacities that was the huge kind of coming out of the recession, you know, tech up into the right, venture-backed tailwind, and also the design tailwind. And again, no grand plan, that was (laughs) that was a lot of luck and happenstance, um, but it, it worked for us perfectly and it positioned us to, to become what we were.

   20. CWChris Williamson12:18

       How about you? What made you the person that was able to spearhead anything and actually g- get ahead of competition?

   21. JRJohn Roa12:28

       Desperation-

   22. CWChris Williamson12:29

       (laughs)

   23. JRJohn Roa12:29

       ... is where it started. Um, (laughs) not even being facetious. I, I had so few options at that point, Chris. I was... It was pretty much like, you know, at best, get like, a minimum wage job in like, sales for a tech company. At worst, go, you know, potentially, you know, deliver food or make coffee or something, and that's where I was. A- and none of, not anything's wrong with that, but that was, that was my set of options. You know, I had, I had fumbled through both high school and college, I had no resume to show, I had spent more of my 20s backpacking around the world than I did getting, you know, lucrative internships. And so I didn't have a lot to stand on. And for me, if I didn't make it myself, I was gonna be slogging probably for the rest of my life to just make paychecks and pay rent and things, and I didn't want that life, and so I was desperate. I was very desperate to, to achieve success. And so that was the biggest thing, because I didn't have much else. I'm not the smartest guy in the room, I wasn't the most educated guy in the room. I had only had failed startups. I'm not even a designer, and that's one of the craziest parts. Like, I, I created what would... became one of the most prestigious design agencies in America and I'm not a damned designer. And I think that that speaks to, first, the desperation, but also as an entrepreneur, we are really designed to be kind of a Swiss army knife. We can kind of do anything, you know, when, when tasked and, and when we're (laughs) desperate enough. And that's what it was. I mean, I tell people all the time, I would have created any company ever that you... that could make money. I didn't care what the company was, it did not matter. I am not passionate about (laughs) that company. I actually founded three companies in the same damn day. Um, Okta was one of three I founded on literally the same day and just, I'd go to events and depending on how the conversation went, I'd like, give a different business card to the person I was talking to. You know? And so it... I just wanted to succeed, and so that's why I was the right person, is that I would do anything to succeed at that point. Um, and then, you know, I'm also a natural born entrepreneur, meaning that I'm pretty persuasive and I can sell and I can motivate people in, in those aspects but that comes way after kind of just the mindset for success.

   24. CWChris Williamson14:29

       That must've been... I, I, I just, I, I think back to the, the period that you're talking about, that early 2010s and how much of a golden era it was for, as you called it, the up and to the right tailwind. Uh, and we've-

   25. JRJohn Roa14:41

       Yeah.

   26. CWChris Williamson14:41

       ... pretty much had either linear or exponential growth, however you wanna say it, between now and back to then. It's been... 2020 has been the first year-

   27. JRJohn Roa14:51

       Yeah.

   28. CWChris Williamson14:51

       ... that we've seen that blip start to fall, so yeah, I, I really imagine that that was a crazy, crazy rollercoaster. How would you define the culture

2. 15:00 – 30:00

   Well, it, it's changed…

   1. CWChris Williamson15:00

      in startups and in Silicon Valley?

   2. JRJohn Roa15:05

      Well, it, it's changed quite a bit and, and I actually think that it's, it's a pretty... (sighs) I don't wanna use the wrong word here. It, it, it's becoming harder and harder to defend the culture. Um, in the late '90s, it was the gold rush, the literal gold rush. No one knew what the hell was going on. Everyone is just hoping for the best and throwing money at anything that breathes and just like, it was a, an absolute (laughs) insane asylum. But there was a few winners, a lot of losers, and then it all dissolved about 10 years later. (laughs) And so, you know, so, so that was the first kind of era and I'm not sure there was a culture. It was just... The culture was chaos. And then in, you know, off the back of the recession, in, in the era when we started Okta and when a lot of the greatest companies today were really, you know, becoming their own, um, from, you know... E- even though like, the, the, the Googles and such had been around for a while, they were just really, you know, kind of... And the Amazon's of the world were all really figuring out their business model then. You also had, um, you know, like the, the, um, the Ubers of the world and Grubhubs of the world, the whole gig economy. That was all that era. And so I would say the culture then was somewhat healthy. You, you had big bets being made on legitimate companies, but they demanded legitimate success. It wasn't that insane see what sticks period like it had been 10 years prior. Um, and people were a little bit more cautious with their capital given that the world had recently had a financial collapse, and so I think it was a s- a more responsible era. And then you started to see the success and everyone got greedy on both sides, the entrepreneurial side and the investor side, and I think that has led to the culture of today which is frankly... It, it's disheartening to me as an entrepreneur. Um, the, the amount of disaster stories that we're having, the Fyre Festivals and the Theranoses and the, the Nikolas and all (laughs) you know? It's like every-

   3. CWChris Williamson17:00

      WeWorks.

   4. JRJohn Roa17:00

      ... week is a new company... The WeWorks. Every week is a new company that just build on false something. E- either at best, like, you know, false proclamations to, at worst, like, felonious fraud.And, and I think-

   5. CWChris Williamson17:15

      (laughs)

   6. JRJohn Roa17:15

      ... that, that, that stems from a, a, a, a level of greed on both sides, right? It's, it's entrepreneurs who are trying to kind of get to that three-comma club and, and it's all about excess and, and it's never about anything that's healthy and about growth. And then investors who are facilitating that, the, the SoftBanks of the world who just throw billion-dollar checks around, you know, like they're, like they're crisps. And so it's like, at some point, it's just insane what's going on. And, and what we don't talk about is the downside of all that, of, of what... of how the entrepreneurs who are taking these bets and running these companies a- are struggling. And the, the sta- statistics around this are haunting. I mean, the entrepreneurs of today, in kind of this high-growth world, have 60% more mental health issues than the average public. This is, um, in America. Um, eight times rated bipolar, six times depression, four times suicide, four times substance abuse. We are melting down (laughs) as the kind of racehorses behind these companies, yet we don't ever hear that story until, until it's a, uh, a horrific headline, like the Aaron Swartzs of the world and, and other folks who've even taken their own lives when they can't handle the pressure. And so, you know, I, I think that it's, it's becoming, you know, somewhat toxic, especially when you look at the biggest companies and how there's just... they all have kind of black eyes now, the Facebooks and the WeWorks, and it's like, "Who can win this game clean anymore?" And I'm not sure that that's a good trend, nor do I know what's... where it's gonna go from here. A- and it worries me a little bit, you know, to be in this industry, quite frankly.

   7. CWChris Williamson18:44

      Do you think that's just a function of the returns becoming decoupled from the value that the companies add? I mean, you know, I, I, I learned with Reves Weideman, who wrote Billion-Dollar Loser about Adam Neumann and about the WeWork saga that's going on-

   8. JRJohn Roa19:03

      Yeah.

   9. CWChris Williamson19:03

      ... I learned the other day the term decacorn, which is a unicorn with a private valuation of 10 billion or over. And briefly, WeWork was one of those.

   10. JRJohn Roa19:14

       Yeah.

   11. CWChris Williamson19:14

       Airbnb is one of those. Uh, a- as you're ta- you're using terminology like the three-comma club and all this sort of stuff, like, in no normal... Like, my dad or, you know, s- your, your uncle, like, they don't think about monetary value in these sorts of terms the way that Silicon Valley does, the way that sort of startup angel investing world thinks about this stuff. It is so unhinged from the reality of-

   12. JRJohn Roa19:45

       Yes.

   13. CWChris Williamson19:45

       ... pretty much everyone. And-

   14. JRJohn Roa19:47

       Yeah.

   15. CWChris Williamson19:48

       ... the, the elephant in the room is that it, it seems to me that the only people keeping this game going are the ones who are there to benefit from it. And from the outside looking in, you can see a ton of businesses that could add more value, but because we have unlimited leverage, unlimited scalability with the internet, you can use the entire world as your potential market, the upside is limitless and the downsides are only negligible.

   16. JRJohn Roa20:15

       Yeah.

   17. CWChris Williamson20:15

       You know, all of this sort of, like, Silicon Valley startup speak that lends... How would you say? It lends a level of consideration and thoroughness and thought-out-ness to an industry which, to me, seems to still be very fledgling. Do you think that's fair?

   18. JRJohn Roa20:36

       (laughs) Yeah, I would say that, that's more than fair. And, and I think the problem is, is that you have both sides facilitating this. There should be a checks and balance kind of system somewhere, like one side should prevent this from happening. A- and if, if you were to ask me, it, it should be the fiduciary side. It should be (laughs) the investors, 'cause entrepreneurs are gonna be ambitious as you let us be, right? But if these investors are like, "Slow down."

   19. CWChris Williamson21:01

       (laughs)

   20. JRJohn Roa21:01

       Like, "How about becoming profitable-

   21. CWChris Williamson21:02

       "Chill out, John."

   22. JRJohn Roa21:03

       ... or whatever." But instead what they do is they, they value companies through the roof and, and they entice this behavior and then they reward it. You know, you... I, I forget how many billions Adam Neumann left with, but it was... he's a billionaire after tanking WeWork.

   23. CWChris Williamson21:19

       (laughs)

   24. JRJohn Roa21:20

       That is not a good model (laughs) to speak about, you know, what you should and should not do. And then you have, like... I don't know if you follow Nikola, which is my new favorite company name, and I say that incredibly facetiously, but Nikola, uh, you know, they're, they're calling themselves Nikola because they want to be like Tesla, which is just a ridiculous thing.

   25. CWChris Williamson21:41

       Oh, didn't they claim... Didn't they claim-

   26. JRJohn Roa21:43

       This is the truck company?

   27. CWChris Williamson21:44

       Yeah, the Iveco. Didn't they say they had a partnership with Iveco? Iveco.

   28. JRJohn Roa21:48

       I'm not sure about your side. So over here, it's, it's a GM partnership. And, and so what they've done is they... they, they, they debuted a truck and it's a, it's a freight truck and, and it's very similar to Tesla's. And, and I forget the... there's a certain kind of battery, if it was... whatever it was. They have a certain kind of battery patented, invented, that can create the most, you know, effective and efficient EVs in the world, et cetera. They debut this truck and they shou- they have this beautifully produced video of this truck flying down the road and whatever. And then they received some billions in pre-orders off the video. And then they never released the truck and they, they say it's in development, development, development. And then a year later they debut a car very similar to the Tesla car. I think it... I, I hope it wasn't called this. It may have been called the Cougar. It's, it's just... it's some horrible name. And, but it's, it's... they, they've developed... they, they now have a, a sedan coming. And again, there's not a single product in the market. They, they now have, have announced a truck and they've announced a car and they've announced this patent that they hold about this battery technology, which people... (laughs) very smart people like an Elon Musk are like, "Yeah, that, that's not a thing. That doesn't exist." Anyway, so then they take the company public in the midst of this tailwind. And at one point, I think the company had a valuation of like $15 or $18 billion. And this is before they have shipped a single product or anybody's even seen a single product. And their CEO, I think his name is Trevor Milton, was out there doing the game and doing the talks and it was very, you know, whatever.And then a short selling firm, which is hilarious, uh, they put a report out, um, th- they, they're actually called Hindenburg Research, which I think is just brilliant.

   29. CWChris Williamson23:32

       Amazing.

   30. JRJohn Roa23:32

       And they, they put a, a, they put a report out claiming that every claim Nikola has made is false and that the, even the video of the truck flying down the road was actually being rolled down a hill and they just turned the tilting of the camera to make it look like it was driving and the truck never even worked. Well, Nikola defends themselves by saying, "Well, we never said it worked. We just s- showed that we have an idea for a truck." And, and then within a week, there's, you know, fraud allegations and Trevor Milton resigns as CEO, he's kicked off the board, the whole dance. Fast-forward a month, their valuation or their market cap as we speak right now is 9.18 billion still. And this is where I'm just like, this is where I, uh, there's just a problem. (laughs) Like, this is a problem is like a company is now on the public stock market giving, you know, investor updates to, to the public-
3. 30:00 – 45:00

   Do you think that…

   1. JRJohn Roa30:00

      He's worth 2.3 billion. And I... And I look at that, and I'm like... (laughs) So, so you're talking about the guy who tanked the company that everyone now hates and then lost investors billions of dollars, who's now living in the Hamptons in a compound alone, is worth... I think he's worth like $6 billion. And David Rubenstein, who has done everything right for 36 years and created true and, you know, and generational companies and, and development, is worth $2 billion. And that's when I'm just like, "There's something really, really wrong here."

   2. CWChris Williamson30:32

      Do you think that you were overpaid for your company when you exited?

   3. JRJohn Roa30:37

      No. Um, uh, I, I think that unlike the businesses that we're talking about, we had, um, an incredible... Well, we, we carried an incredible amount of value in, in our discipline. And, and we... You know, we had incredibly high profit margins. We were bootstrapped through and through. I never took a dollar in capital ever.

   4. CWChris Williamson30:56

      Can you just-

   5. JRJohn Roa30:57

      And so, we-

   6. CWChris Williamson30:57

      ... explain what boo- bootstrapped means, please?

   7. JRJohn Roa31:00

      Yes. So, so absolutely no investors or outside capital. So I s- I started the company with about $800 net investment, um, that was on the back of a credit card, and I used the revenue and then profit from the first client to facilitate growth and did that from then on. So, you know, you cannot... All the examples we've been giving from the, you know, Teslas and the Nicolas and the Fruitworks, you can't do any of those relying on your own profit because they don't have any. So for us, I had to run an incredibly value-based business with high margins and high throughput and great cashflow management and stuff to do my business, or else it would have failed. And so, you know, we had an incredible amount of value, we did extraordinary work, and Salesforce, um, was incredibly intelligent on how they saw the value proposition of a business like mine fitting into, uh, to their consulting group, and it was, you know, fortuitous on, on both sides. The majority of my employees that they acquired are still at Salesforce, you know, five years later, w- you know, inside fantastic long-term careers. And, and, um, you know, and they're also one of the fastest-growing Silicon Valley stocks since then, so...

   8. CWChris Williamson32:07

      That's awesome, man. That's proper like leg- legacy shit.

   9. JRJohn Roa32:12

      Yeah, I mean, listen, I... It was a small business by all intents. You know, we were, we were a small company when it com- when you compare it to Salesforce or even most of the businesses they acquire. They do a lot of, you know, multi-billion dollar acquisitions, et cetera, et cetera, um, that, you know, wasn't us. We were a small, kind of going on medium-sized company, but it obviously... you know, it was a lot more, um, I would say real than who we're talking about. It was a real business with real cashflow and real people in it. And, and that's what they wanted to acquire, and, and we're happy they did, and, uh, and I think everyone is very satisfied with how that all went down.

   10. CWChris Williamson32:45

       Awesome. Talk us through the craziest year that you had in business then, personally. What, what was going on? What was a typical day? What were some of the big incidents which occurred?

   11. JRJohn Roa32:57

       Yeah. It, it was the year... It was the last year of the company that I alluded to earlier, and it kind of... You know, the reason it was so crazy is because, you know, I'm managing a company that, that had just experienced 1100% organic growth-

   12. CWChris Williamson33:09

       (laughs)

   13. JRJohn Roa33:09

       ... in 12 months for an agency. This is an agency. Like, you know, it's one thing to scale a software company because you can hire a few more people but then grow 1000%, and it's... you know, it's just scaling software. When you scale an agency, you're, you're scaling human beings who are incredibly difficult to hire. They are very expensive. And so, um, we had exp-... That, that was the growth we were experiencing. We were, we were, I think, the 400th, give or take, fastest growing company in America of any kind, and I, I think the, the only... the only fast-growing agency in that caliber of our, of our type in our specific niche. And, um... So things are going well, a- and I am in a position where I am being recognized for that success. I am being asked to do interviews and TED Talks, and I'm on magazine covers, and this is a new world for me. I have never (laughs) experienced anything like that. And people care about who you are and what you're up to, and you... you're invited to all kinds of crazy stuff. You have a seat at the table with, you know, the, the, the governors, and it- it's, it's that world. And, and all of a sudden, you're then making money. I, I became a millionaire the day before I turned 30. And, you know, I, I had this stretch goal as a teenager of being a millionaire by 30, and I literally got there the day (laughs) before I turned 30. Um, and that's not even like a... That's not even facetious. Literally, my last day being 29, I became a millionaire. And so from all of that, things were going very well. And it was a bit surreal. It was going so well. But at the same time, this is when personally I was struggling more and more and more and more and more. And so you had these diametrically opposed kind of positions where as one side, the kind of public side if you will, is, is, uh, going about as well as it can and then seemingly just continuing to get better, everything that people can't see was just systematically getting worse and worse and worse and worse and worse. And p- you know, no one knew I was dealing with lawsuits from another... you know, from an old business partner. No one knew that, you know, I was battling every day to, you know, to, to win certain accounts that if we had not got or we had lost certain clients, we could have, you know, had a down year or whatever. Um, no one knew I was dealing with the mental health issues that I was. No one knew that I was, you know, escaping to, you know, Las Vegas or another degenerate playground, you know, three times a month and, and, and having very bad behavior, 'cause that's what... uh, that's what allowed me to stop thinking about all my issues for a day or two. And so it was... You know, and, and work was so busy, it was like... It was almost being managed to the minute. I remember I'd have a... you know, my assistant would be like, "You have a call. I'm gonna start it at 9:16, and at 9:22, I'm gonna grab you so you can go do this." It was like that was my day. And...... it, you know, it was just, it was truly crazy in so far as there were incredible parts, there were very dire parts. And it was such, it was where I always wanted to be. I was succeeding for the first time ever, but it didn't really feel like it because there was all this other stuff I was dealing with. And so, th- that was a truly, truly crazy year. I mean, we, I don't know how many people we hired that year. We were tr- we were op- opening up offices in London and then in the West Coast. And we, um, God, we, we opened up a massive gorgeous office in Chicago that we designed, like I designed every s- square inch of that place and it was just incredible. Uh, we had signed all of our major cl- accounts, like the BMWs of the world. We, you know, designed the interior of one of their cars, like crazy stuff. And so that was, that was the coolest period of my life ever, while also being the worst period ever.

   14. CWChris Williamson36:35

       (laughs) Man, y-

   15. JRJohn Roa36:37

       Which I think is entrepreneurship in a nutshell.

   16. CWChris Williamson36:39

       Oh, absolutely. So, here's something that I learned, uh, from Ben Bergeron's Chasing Excellence, which is that when we look back on a lot of the experiences that we have in life, especially to do with sort of business and discomfort and stuff like that, we don't ever look back and find any glory or really any interest in the times when things were easy. What we find as the real exciting times is, "Oh, do you remember when we had to pull three all-nighters in a row to get the project finished?"

   17. JRJohn Roa37:06

       Yeah.

   18. CWChris Williamson37:06

       "And we all did dominoes and you slept under the desk," and this, this and... Like, ev- you know, even the people listening who aren't an entrepreneur, you can remember, um, completing an assignment for school or college or something-

   19. JRJohn Roa37:16

       Yeah, yeah, yeah.

   20. CWChris Williamson37:16

       ... and you, you had to pull, you had to get a case of Red Bull in and you and your friends didn't leave the library for three days. You know, that's where the glory is associated with it. But obviously-

   21. JRJohn Roa37:26

       Yeah.

   22. CWChris Williamson37:26

       ... the, the goal of that or the, um, yeah, the proposed, the best outcome of that is to avoid going completely broke in one way or another. Broke physically, broke-

   23. JRJohn Roa37:39

       Yeah.

   24. CWChris Williamson37:39

       ... spiritually, broke mentally, broke financially. You know, broke to jail (laughs) like, uh, judicially.

   25. JRJohn Roa37:44

       Yeah. Y- it's, it's, yeah, and you're spot on with that and I, I resonate with that a lot because when I think back of my journey, I rarely think about the, quote unquote, "great times". Like what comes to my mind first is not the money, not like, the, the, the day I became a millionaire, I barely recall it. I, I saw my bank account, I was like, "Oh, a million dollars." And I called my mom to tell her and she's like, "Nice, John." Like, no one gave a shit, it was very uneventful. Even though that was a somewhat, I don't know, that was, that was a, that should've been, I think, a memorable day or maybe is for some people.

   26. CWChris Williamson38:18

       It's a m- it's a big milestone, right?

   27. JRJohn Roa38:20

       Yeah, y- you'd think so, except it was highly forgetful-

   28. CWChris Williamson38:24

       (laughs)

   29. JRJohn Roa38:24

       ... you know, forgettable for me compared to some of the tragic, fucked up times that we had. And, and there's this quote by my favorite author, Chuck Palahniuk, and, and he says, "It's so hard to forget pain but it's even harder to remember sweetness. We have no scars to show for happiness. We learn so little from peace." And I think that that really speaks to entrepreneurship in a big way, is that we, we actually, i- in, in those times where things were just great and things were happy, you don't learn a lot, you're not really progressing. It really is those battles that you hopefully win when, when you really are in the best position you can be in.

   30. CWChris Williamson39:01

       What are some of the lowest points that you can remember from that year?
4. 45:00 – 57:09

   I understand. You think…

   1. JRJohn Roa45:00

      I would've had the wherewithal to not... to, to do anything different. I still don't know if I had just known the result, what I possibly would have done different. And the reason I say that, and this is kind of a weird thing that people don't always expect I would say, is because it worked. So had I changed anything, like, like for instance, I was dating this wonderful woman named Courtney when the, when the whole company started. I broke up with her in the second year 'cause I convinced myself that I could not be a good partner and, and give attention to somebody while being a great entrepreneur and CEO. I said, "There's not enough bandwidth to do both, so I'm gonna choose being an entrepreneur." And I now realize that's ridiculous. That's hogwash. Like you, you can... There's a lot of people who not only are great partners in the process, but they attribute their success to that partner. And so, but with that said, if I were to, to go back and let's say I could do it all again, but this time, instead of becoming a degenerate, I stayed with my lovely girlfriend and, and used that as an anchor, maybe I wouldn't have worked as hard. Maybe I would have been distracted. M- so it's... So I can't reasonably say that there are things that I would actually change, because I don't know what the result would have been. Um, looking forward, which is all we can really do, if I was to start a company right now, obviously I would do everything differently. The first would be not to bet my entire life and existence on a damn tech company, but secondly would just ways to, to be mentally, you know, a- acute, you know, ways to, um, stay attuned to your, you know, m- your mind and body throughout the entire journey to find methods of support, to have a good structure around you, to be honest what you're dealing with, to seek therapy. I would do all of those things now and that... But that's looking forward. It's very difficult to say wh- looking back, because at the end of the day, it worked. Wh- who am I to say that I should have done it differently if it worked? So it's a, it's a weird kind of place to, to reflect from.

   2. CWChris Williamson46:49

      I understand. You think the ends justified the means by that logic?

   3. JRJohn Roa46:55

      Uh, a little bit. And, and again, this is where it's hard to admit that, because, you know, I, I had some pretty bad behavior and I'm not proud of a lot of what I did, and, and it was a pretty wild few years. I wasn't a very good son or brother or friend to people. And so, like, it's not that it justifies it, but at the same time, if you were gonna go redo it, wouldn't you want the same result? (laughs) And so it's kind of hard to say like, you know, I would've, I would have been a better friend, um, but I would happily have, you know, gone bankrupt. It's like-

   4. CWChris Williamson47:24

      Yeah. Yeah.

   5. JRJohn Roa47:24

      ... yeah, probably not. (laughs) You know? Like-

   6. CWChris Williamson47:26

      Yeah.

   7. JRJohn Roa47:26

      So it, it's, it's hard... It's very difficult to reflect on it from that way, and that's why for folks who, who have read the book or are going to read the book, I, I worked very hard while writing it to not judge. I, I didn't want to say like, "Oh, I wish I hadn't done this," or, "I so regret this," or, "Man, look how brilliant I was." It's all just what happened. It's just a story that we can now look back on for some high level indicators, but it's not a practical...

   8. CWChris Williamson47:53

      (laughs)

   9. JRJohn Roa47:53

      No pun intended. It's not a practical guide for what to do or what not to do.

   10. CWChris Williamson47:57

       Yeah. I think that's a really, um, reassuringly unique-... viewpoint, a stance that you've taken that very often it would be easy for someone to polarize their opinion for it to be, "Yeah, it was absolutely worth it," or, "No, I, I, I definitely wouldn't have done it that way. I would have totally changed things around."

   11. JRJohn Roa48:17

       Right.

   12. CWChris Williamson48:18

       Um, I think that it's w- very reassuring to know that there's someone who is prepared to sort of go to that uncomfortable place of truth. Uh, and, and, and also to deliver it with a little bit of subtlety and nuance. I think that is interesting. Just to bookend the girlfriend discussion, we've spoken about this on the show before.

   13. JRJohn Roa48:36

       Mmm.

   14. CWChris Williamson48:36

       Do you think, on balance, that more entrepreneurs are successful with or without partners, if you take a normal distribution of entrepreneurs?

   15. JRJohn Roa48:45

       More are successful with partners, for sure. Based on, based on stories that I've heard, conversations that I've had, people are more successful with partners.

   16. CWChris Williamson48:53

       Why do you think that is?

   17. JRJohn Roa48:53

       Um, and, and I think I may... Well, I think it's, it's quite obvious. I think it creates... A- assuming the relationship is healthy, right? I think that, uh, you know, people can find themselves in somewhat toxic relationships in those journeys because it can feel comforting at first. It's kind of disguised comfort. But I think if you're in a secure, healthy relationship, you have an automatic support system, which is something we normally lack as entrepreneurs is any kind of support system, much less one who you're literally with every day. It forces you to not isolate, which is a very common, you know, characteristic of entrepreneurs. We lock ourselves in a room and hope for the best. Um, if you're with somebody, they're not gonna let you do that, likely, or at least not constantly. And so you're gonna be pulled out of your element and forced to talk and forced to, to realize there's more going on than your little tech company. Um, and I think that there's gonna be a sense of compassion that you forget people will have for you. One thing that I, I experienced in my journey, and I've h- heard a lot from entrepreneurs, is that we kind of find ourselves in, in this, like, um, like a shame spiral kind of environment, where we're, we're shameful for what we're doing and how we're spending our time and we don't want to admit the decisions that we've made. And so that's where a lot of that inner turmoil comes from, and I think if somebody's saying to you, you know, "Listen, I understand you have a lot of hard decisions to make and it's okay and I, you know, I would do the same thing," even, as silly as it sounds, just hearing that would have done a lot for me and I know for other people. So, um, so yeah, I, I, I think, you know, again, I can't call it a rule. I can't tell somebody who's like (laughs) ... If there's some single entrepreneur, I can't be like, "Go find a partner-"

   18. CWChris Williamson50:19

       (laughs) "Find yourself a relationship." Stat.

   19. JRJohn Roa50:22

       "... and then (inaudible) and then find..." You know, that, that's ridiculous, but I can say off a lot of discussions with incredibly successful people, that is more often than not a key.

   20. CWChris Williamson50:32

       That's really interesting. I think, I think that you are correct with that as well. I, I know my experience as an entrepreneur for 14 years, that the rumination and the amount of time that you spend inside of your own head... I mean, what, uh, uh, think about what you were doing. You said it before, why were you going to Vegas? Why were you partying hard? It was in an effort to force yourself out of that head.

   21. JRJohn Roa50:52

       (laughs)

   22. CWChris Williamson50:52

       And, you know, even stuff, even stupid things like owning a dog, you know? Like, if you own a dog-

   23. JRJohn Roa50:58

       Yeah. Yeah.

   24. CWChris Williamson50:58

       ... you have to project that... You, you, you dissolve your sense of s- self-important because there is something else and it's beholden to you. You need to look after it.

   25. JRJohn Roa51:09

       Yeah.

   26. CWChris Williamson51:09

       Right? So I think-

   27. JRJohn Roa51:10

       Yeah.

   28. CWChris Williamson51:10

       ... that is a... That's a really, really interesting insight. So, okay, we've had this, we've had this crazy career. We've, w- we've done also the learning and the reflection, hopefully sufficient time for you to be able to at, at least begin to normalize what it was that you went through. What are the high level lessons? What can we take away from it and try and implement into our own lives or avoid or... Strategies and everything.

   29. JRJohn Roa51:35

       H- honestly, this is gonna sound... This is a horrible answer to your question, but I don't really have too many. A- and the reason is, is because, it, i- uh, going back to the earlier point that you made, kind of about nuance is, I made a lot of mistakes, and so for me to try to tell people what they should do or what the lessons are, I think is ridiculous. Like, uh, you know, a- and it's... I hate that successful people believe that they have more sense of what is good and bad, right and wrong, the right or wrong ways to do things, than other people do, because we generally have our, our timeline, right? And so I can speak to some personal things that I've experienced, but they don't translate into blanket advice or lessons or any of those things. Because if, if I, if, if I speak to an individual, and Chris and I... If we're having a, a pint in London and you, you're saying to me, "Hey, here's my situation, can you give me some advice based on yours?" I would happily do so. But if I'm speaking to a room of entrepreneurs and I say, "Here's three things you should do," maybe 5% of those it could be perfect for, 80% of it's irrelevant, and 15% I'm gonna damage by them following my advice.

   30. CWChris Williamson52:34

       (laughs)

Episode duration: 57:09