Modern Wisdom - #242 - John Roa - The Dark Side Of The Startup World

Episode Date: November 7, 2020

John Roa is an entrepreneur and an author. We often hear about the galactic successes of high growth startups, but what is the price that the founders pay to enable it? Expect to learn what the real culture of silicon valley is, how your business can cause a psychotic breakdown, what John realised is truly valuable in life, how market sentiment and true value have become detached and much more... Sponsor: Get 50% discount on your FitBook Membership at https://fitbook.co.uk/join-fitbook/ (use code MODERNWISDOM) Extra Stuff: Buy How To Get Rich & Die Trying - https://amzn.to/38aNh8s Follow John on Twitter - https://twitter.com/johnroa  Get my free Ultimate Life Hacks List to 10x your daily productivity → https://chriswillx.com/lifehacks/ To support me on Patreon (thank you): https://www.patreon.com/modernwisdom - Get in touch. Join the discussion with me and other like minded listeners in the episode comments on the MW YouTube Channel or message me... Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx YouTube: https://www.youtube.com/ModernWisdomPodcast Email: https://www.chriswillx.com/contact  Learn more about your ad choices. Visit megaphone.fm/adchoices

Hi friends, welcome back. I guess today is John Roer and we're talking about the dark side of being an entrepreneur. We often hear about the galactic success stories coming out of Silicon Valley, how much money can be made by angel investors and startups. We don't actually hear about what sort of an effect that has on the sanity of the people who are running the company. And today we get a really stark, honest, and open insight into just what that world is.

John had a dissociative psychotic breakdown halfway through running one of the fastest growing companies in America's history. And that particular episode resented his view on what matters in life. And this is a really unique opportunity to see exactly what it's like to be operating at kind of the highest levels of growth. And the price that people need to pay for that.

I've been talking a lot recently about, you do not get to take part of someone's life, you have to take the whole. What is the price for being Elon Musk? What is the price for being Conor McGregor? And a lot of the time we can look at these founders and investors and think, oh, I'd love that life. That sounds fantastic to me. And in reality, the price that they need to pay is one that we wouldn't even consider. So, yes, hopefully this helps to give us all a little bit of perspective. And also we talk about the culture of Silicon Valley and just how completely detached from the real value in the world, a lot of the market sentiment around the valuations of these companies has become. But for now, it's time for the wise and wonderful John Rower.

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? Yeah, so I'm a pretty lifeer entrepreneur. I've been in the tech world since I was technically 11 years old when I learned a program, code, hack, game, build computers. And then my first company, I started when I was 14. So I'm now 36, so two know, two thirds of my life almost I've been running tech companies.

And it's just been, you know, it goes without saying a passion of mine forever. And you know, kind of before it was invoked like it is today. I really just had a knack for computers and 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 that journey led to a number of tough lessons, 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 was kind of down on my luck. It was not a great time

personally and professionally. It was in the midst of the recession globally, but obviously, a lot of that was happening here in the US. I was out of work. My parents were out of work. The family wasn't doing great, and I was not really present with a lot of options on what to do to 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 get out of debt and those kind of things. So of course, I did the entrepreneurial thing and I created a company called Aqta. And you know, for those of the listeners that might know a company called IDO, that's the best way to describe Aqta is that we were an innovation and design consultancy and companies like IDO have been around for decades and they've been helping everybody 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. Because the ideas of the world were all kind of old industrial designers and print designers who would kind of move 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. market. And that's what we did. Created the company in 2010, bootstrapped, no investors, no partners, no investors, no anything, I mean, no board, no mentors, like truly a one-man band. And just kind of right place, right time, a lot of luck, perseverance, good fortune, grinding, and two years later, it was the single fastest growing innovation in UX agency in America, one of the fastest growing companies of any kind in America.

Two years after that, we had acquired companies, we were growing nationally and internationally. We were doing work for incredible companies. Our clients were BMW and United Airlines and others. And ultimately, 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 doing TED Talks and being photographed from magazine covers, who was kind of this very lamerous success story on one side. And the other side is what no one knew what was going on, which is also a classic story

that I was really struggling personally. 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 mechanisms for any kind of support. And I started to struggle, I mean, at a worse and worse level throughout those years, really deep mental illness and mental episodes of depression and anxiety, those kinds of things as I was dealing with the company, 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, it all collided with itself, and that took the form of a pretty

severe mental breakdown. I ended up in the hospital, suffered disassociative amnesia, didn't know who I was, where I was, had no recollection of any part of my life, could you tell you my own name? And it was in a hospital in that state for a number of days. They weren't sure if I would come back, if what state I'd be in, if my brain didn't have fully recovered, it was a very scary time of my life. And this is all still when the company is you know, quote unquote, crushing it in the public. And no one knew except one person to company. My parents didn't know my siblings didn't know, no one knew. one person at the company. My parents didn't know, my siblings didn't know, no one knew.

I hit it for everybody. Got back to work whenever I was released from the hospital 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 have to end of this before it ends. And I went and hired to invest in bank.

We ran a managed auction and very fortunately sold that business outright to Salesforce. I was the biggest company in San Francisco about a little under a year after that whole episode. And obviously a very fort two it is exit. It was the best case, you know, best result I could have ever asked for, given 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 on everything. It changed how I think about success, what is success. It changes how I think about what, you know, what risk is worth risking and what parts of our lives we should be betting on and trading for that chance at success. It's chained by perception on what matters in life going forward. It was a pretty wild journey. That all happened five years ago. And so in the last five years, I've actually been on

your side of the world, Chris. I lived in London for half a year, each year, and then in Greece, via the other half the year. So I was doing very little, except in Joing Life and just trying to reset after what I had endured. And ultimately, you know, trying to reframe what it all meant. And 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. And it's everything I just shared in excruciating detail, maybe too much detail in some parts. But I wanted to get across the real story that we don't often talk about.

People are rightfully afraid to talk about. 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 exciting. Yeah.

What a journey, man. Congratulations. It really, it really sounds like you're in a significantly better, more awakened, more aligned position than you were. To say the least. Yes. It's, you know

It's um, it's difficult to describe how different because you know I think that there's this this this Illicun-seed notion that we change as people. I don't believe that's true at all and most most People smarter than me don't believe it either is that but we can what I can't 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, mostly mentally, but also physically. But yes, it is a very different place in mindset today, thankfully. 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're talking about this incredible success that you had with your company, very, very fast growing in, you know, in 2010, the early 2010s, that period was, I would imagine, incredibly competitive for tech companies, 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 that you had any success in business? You mentioned about work rate and timing and stuff.

Could you dig into that a little bit? Definitely. So the one thing that we did that was most intelligent, that we did not realize we were doing, was being a support structure to that tail when that you're talking about. You know, this is the era when all of these now more billion dollar tech companies were coming out. The Uber's the world everybody else. 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 Aqta

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 could do 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.

I will not pretend to say that was some grand plan that we had concocted. That's just the way it worked. And the second thing is that, I mean, it's funny I actually have the Apple presentation on, and my other monitor here, because they just debuted the 5G iPhone. But Apple had done 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 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 blackberries, and we had our palm pilots, 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 blackberries and we had our palm pilots 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 needed device to do. At the time, it could send a text message, and an email, you could serve the web, you could listen to music. 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 in its other 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 media consumption patterns, way better than we do.

And if you remember when the iPad was debuted in 2011, everyone made fun of it. They're like, why do we need this big fucking iPhone, right? And there was like these memes people holding the iPad to their head. Like it was a joke. And now it's revolutionizing industry and changing everything. Apple, this is their ability. This is why they're a trillion dollar, now a multi-tillion dollar company. This is 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, innovation, and user experience, and user needs, and heuristics, and all those aspects, they could also create a competitive advantage like Apple. And so that's what we basically did. We would go to companies and we would say hiring us or hiring Octa is kind of like if you could hire Apple to build your product for you, which 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 back tailwind and also the design tailwind. And again, no grand plan that was that was a lot of luck in happenstance. But it worked for us perfectly. And it positioned us to become what we were. How about you? What made you the person that was able to spearhead anything and actually get ahead of competition? Desperation is where it started Not even being pleased. I had so few options at that point Chris I was it was pretty much like you know At best get like a minimum-way job and 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 and none of not doing things is wrong with that best get a minimum-of-way job and sales for a tech company at worst go potentially blooper food or make coffee or something. That's where I was. None of the things is wrong with that, but that was my set of options. 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 lucrative internships. I didn't have a lot to stand on.

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 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. It wasn't the most educated guy in the room. I had only had failed startups. I'm not even a designer. And room. It 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 created what became one of the most prestigious Designations in America and I'm not a damn 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 when we're desperate enough and. 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 that company. I actually found three companies in the same damn day. Octo was one of three. I found it 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 person to what I'm still talking to. And so 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.

And then I'm also a natural born entrepreneur, meaning that I'm pretty persuasive and I can sell and I can motivate people in those aspects. But that comes way after just the mindset for success. That must have been, I think back to 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 until the right tailwind. We've pretty much had either linear or exponential growth, however you wanna say it, between now and back to then.

It's been 20, 20 has been the first year that we've seen that blip start to fall. So yeah, I really imagine that that was a crazy, crazy roller coaster. How would you define the culture in start ups and in Silicon Valley? Well, it's changed quite a bit. And I actually think that it's a pretty, I don't want to use the wrong word here. It's becoming harder and harder to defend the culture.

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 an absolute insane asylum. But there was a few winners, a lot of losers. And then it all dissolves about 10 years later. And so, you know, 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, off the back of the recession, in the era when we started the Octa and when a lot of the greatest companies today were really becoming their own, from even though the Googles and such had been around for a while, they were just really, and Amazon to the world were all really figuring out their business model then. You also had, you know, like the, the, the Ubers of the world, the Grubhub is 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. People were a little bit more cautious with their capital, given that the World Head recently had a financial collapse. I think it was a more responsible era. Then you started to see this success. Everyone got greedy on both sides. The entrepreneurial side and the investor side. I think that has led to the culture of today, which is frankly, it's disheartening to me as an entrepreneur.

The amount of disaster stories that we're having, the fire festivals and the Theranos' and the Nicolas, you know, it's like every week is a new company, the we works every week is a new company. It's just build on false something. Either at best, false proclamations to at worst, like, full, lonious fraud. And I think that stems from a level of greed on both sides, right?

It's entrepreneurs who are trying to kind of get to that three-coma club, and it's all about excess, and it's never about anything that's healthy and about growth, and then investors who are facilitating that, the soft banks 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 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 statistics around this are haunting. I mean, the entrepreneurs of today in kind of this high growth world have 60% more mental health issues in the average public. This

is in America. Eight times rated bipolar, six times oppression, four times suicide, four times substance abuse, we are melting down as the kind of race forces behind these companies, yet we don't ever hear that story until a horrific headline, like the Aaron Schwartz is the world and other folks who have even taken their own lives when they can't handle the pressure. And so, I think that it's becoming somewhat toxic, especially when you look at the biggest companies and how they all have black eyes now, the Facebooks and the WeWorks, and it's like, who can win this game clean and more?

And I'm not sure that that's a good trend, nor do I know where it's going to go from here, and it worries me a little bit, you know, to be in this industry quite frankly. 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 learned with Reeves Wydomen who wrote a billion dollar loser about Adam Newman and about the we work saga that's going on. I learned the other day, the term deca corn, which is a unicorn with a private valuation of 10 billion or over. And briefly, we work was one of those, Airbnb is one of those. And as you taught you using terminology, like the three comma club and all this sort of stuff, like in no normal, like my dad,

or you know, 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 start up angel investing world thinks about this stuff. It is so unhinged from the reality of pretty much everyone. And the elephant in the room is that 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. You know, all of this sort of like Silicon speak that lens, how would you say? It lends a level of consideration and thoroughness and thought outness to an industry which to me seems to still be very fledgling. Do you think that's fair? Yeah, that's more than fair. And I think the problem is that you have both sides of facilitating this. There should be a checks and balance kind of system somewhere. Like one side should prevent some happening. And if you were to ask me, it should be the fiduciary side.

It should be the investors, because entrepreneurs are going to be ambitious as you let us be, right? But if these investors are like, slow down, like, how do you come to profit or whatever. But instead, what they do is they value companies through the roof and they dice this behavior and they reward it. I forget how many billions Adam Newman left with, but he's a billionaire after tanking we were.

That is not a good model to speak about, you know, what you shouldn't should not do. And then you have like, I don't know if you followed Nicola, which is my new favorite company. And I say that incredibly facetiously, but Nicola, you know, they're calling themselves Nicola because they want to be like Tesla, which is just a ridiculous thing. But didn't they claim that the truck company? Yeah, just a ridiculous thing. Oh, didn't they claim? Didn't they claim that they... This is the truck company. Yeah, the Iveco. Didn't they say they had a partnership with Iveco? Iveco.

I'm not sure about your side. It's over here. It's a GM partnership. And so what they've done is they debuted a truck. It's a freight truck, and it's very similar to Teslas. And I forget the... There's a certain kind of battery, if it was... Whatever it was.

They have a certain kind of battery pat if it was, whatever it was. They have a certain kind of battery patented and then to that can create the most, you know, effective and efficient EVs in the world, et cetera. They debut this truck and they should have this beautifully produced video, this truck flying down the road and whatever. And then they received some billions and pre-orders off the video. And then they never released the truck and they say it's in development development. And then a year later they debut a car, very similar to the Tesla car.

I think it, I hope it wasn't called. It's a maybe called the Cougar. It's a so horrible name. But they now have a sedan coming. And again, there's not a single product in the market. They now 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,

very smart people like in Elon Musk are like, yeah, 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 it's James 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. They put a report out, they're actually called Hindenburg Research, which I think is brilliant. And they put a report out claiming that every claim Nicola has made as false.

And that 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, Nicola defense themselves by saying, well, we never said it worked. We just showed that we have an idea for a truck.

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 market cap, as we speak right now, is 9.18 billion still. And this is where I'm just like, this is where I, there's just a problem. Like, this is a problem. A company is now on the public stock market giving investor updates to the public that is worth $10 billion after it's getting caught in a massive act of fraud that is now being federally

investigated led to the CEO resigning. And it's like, okay, there is a problem right now. And this stuff worries me. So yeah. I spoke to Reeves about this. Will you privy to the insane uplift that was seen when the electric scooter companies first came out? Of course. I mean, at least they had products, but even that, even that the market sentiment and the valuation, I remember because I was in America at the time, and they were doubling the valuation of lime and bird and the other ones.

They were doubling every month. It was like 100,200,400,800,000, and that was the period of time I was in America. Like, I ventured into America and there were worth like 100 million. I left America and there were 800 million. Well, and this is the worrisome part is like, is you wonder how this is facilitated? Because it was on the public market, it could be market manipulation, whatever.

But it's on the private market. Someone is facilitating this. And it's, and what's scary is that it appears to be these investors. Like the soft bank is a great one to do it. I mean, they looked at Adam Newman and said, how much money do you need? He's like a billion dollar. They're like, right, here's 20. And what's scary is that it appears to be these investors. Like the soft bank is a great one to do it. I mean, they looked at Adam Newman and said, how much money do you need? He's like a billion dollars.

They're like, right, here's 20. And it's like, what? Like, no, I needed one. And then they're like, well, how do you have 20? And so you better use this to do completely unrealistic things and create unrealistic sense of scale and growth. And then they wonder why he creates an unsustainable model. And so it's no mystery why this is happening, but it certainly is a mystery to me that

it continues to happen. And this is still happening every single day right now. It just blows my mind. Is this house of invisible emperor clothes cards gonna come crashing down at some point? The thing is there's too much money behind the soft banks in the world. The reason that they're cutting these checks,

they don't know what else to do with it. And this is all Saudi wealth fund or sovereign fund backed capital, right? So there's hundreds and hundreds of billions of dollars that they're trying to deploy. And so well, and they're just one of them. And so well, those kind of funds are out there of literally limitless capital.

They're gonna continue to make ridiculous bets and find a way out of them, which is the craziest part. Like, when they kicked out Adam, they brought in, you know, their own, I think it's a former GP of the fund to now be the CEO of we work. So they just kind of like hyper scale, let it crash to the ground, put their own people in,

probably take the majority of the equity, and then build them up and they'll probably have a fortuitous exit, which is, which is obscene that they're gonna actually win on that deal, probably, at some point. It's happening with Uber, it's happening with all these companies. So, until the entire paradigm changes and investors actually worry about making their money back with any kind of practicality, it's hard to say how this will change because who's

going to turn down that money and that opportunity. It's like an entire industry that is a golden goose. In fact, no, it's an entire paradigm, a whole structure where people are just able to print money. I've had Jason Callicanis on here a little while ago, and I just, I tried to get him to explain to me about how Angel Investing works, but I think fundamentally, because I'm a small medium-sized enterprise entrepreneur, the fact that market sentiment and valuation is completely decoupled from what the service that the business can actually produce, for me, it's a logical step that I am unable to take. It's like I haven't had that module loaded into my brain from the matrix And I just can't get how it works.

And then we've seen, even with companies that are operating this year, let's look at Tesla. Like what is it? Five X, or five X, it's stock price. Way, way, way above companies like Nissan and Ford. And I'm sure you saw these graphs about the volume of cars that Tesla produces versus the volume of cars that Tesla produces versus the volume of cars that Ford produces

is like the same differential as the stock valuation between the two of them, but in reverse. That was the whole piece going. It's crazy. And this is where you have to wonder, again, a lot of the massive tech bubble of 2020 right at the back of the pandemic kicking in was soft bank, right? It was revealed that soft bank was actually buying all these equities to drive these prices

through the roof. So, it's kind of all part and parcel. It's all working together in the same systems, but it's a scary thing. And, you know, the fact that you can become a billionaire by tanking a company is scary. I was speaking to David Rubenstein, who is the founder of a Carlisle group. One of the most successful businessmen in America, unequivocally. He creates one of the biggest private equity companies in the world. He is revered amongst that world.

He is in the same category as the Bill Gates and those kind of folks. He lives in DC,'s highly politically connected. He's also the chairman of the Smithsonian of Duke University. I mean, it's like, this guy is, is literally one of the biggest power brokers in the world and has earned it over the last 36 years of doing what he's done. He's worth 2.3 billion. And I, and I look at that and I'm like, so you're talking that the guy who tanked the company that everyone now hates and then lost investors billions

of dollars who's now living in the Hampton in a compound alone is worth, I think he's worth like six billion dollars. And David Rubenstein who has done everything right for 36 years and created true and you true and the generational companies and Developments worth two billion dollars and that's what I'm just like. There's something really really wrong here Do you think that you were overpaid for your company when you exit it? No I think that Unlike the businesses that we're talking about, we had an incredible, well,

we carried an incredible amount of value in our discipline. And we had incredibly high profit margins. We were a bootstrap through and through. I never took a dollar in capital ever. Can you just explain what bootstrap means, please? Yes. So, absolutely no investors or outside capital. So, I started the company with about $800 net investment.

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 for none. So you cannot, all the examples we've been giving from the, you know, Teslas and the Glows and the Proof works, 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 cash flow management and stuff to do my business, where else it would have failed. And so, you know, we had an incredible amount of value, we did an extraordinary work and Salesforce was incredibly intelligent on how they saw the value proposition of a business like mine fitting into their consulting group. And it was, you know, portoued as on both sides. The majority of my employees that they acquired are still at Salesforce, you know, five years later, you know, inside fantastic long-term careers. And, and, you know,

and they're also one of the fastest growing Silicon Valley stocks since then. That's awesome, man. That's proper legacy shit. Yeah, I mean, listen, it was a small business by all intents. We were a small company when you compare two sales force or even most of the businesses they acquired. They do a lot of multi-billion dollar acquisitions, et cetera, et cetera. That wasn't us. We were a small kind of going on medium-sized company, but it obviously, it was a lot more, I would say, real than who we're talking about. It was a

real business with a real cash flow and real people, and that's what they wanted to acquire, and we're happy they did, And I think everyone is very satisfied how that all went down. Awesome. Talk us through the craziest year that you had in business then personally. What was going on? What was a typical day? What was some of the big incidents which occurred? Yeah, 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 had just experienced 1100% organic growth in almost per 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 a thousand percent and it's, you know,

it's just scaling software. When you scale in agency, you're scaling human beings who are incredibly difficult to hire. They are very expensive. And so that was the growth we were experiencing. We were, I think, the 400th give or take fastest growing company in America of any kind. And I think the only fast growing agency in that caliber of our type and our specific

niche. And so things are going well. 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 experienced anything like that. And people care about who you are and what you're up to and you're invited to all kinds of crazy stuff. You've got to see to the table with the governors. And it's that world. And all of a sudden you're then making money.

I became a millionaire the day before I turned 30. And I had this stretch goal as a teenager of being a millionaire by 30. And I literally got there the day before I turned 30. That's not even like, that's not being prestigious. Literally my last day of 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 so you have these diametrically opposed kind of positions where as one side, the kind

of public side, if you will, is going about as well as it can. And then seemingly just continuing to get better, everything that people can't see, which is systematically getting worse and worse and worse and worse and worse. And no one knew I was dealing with lawsuits from an old business partner. No one knew that I was battling every day to win certain accounts that if we had not got or we had lost certain clients, we could have had a down year or whatever. No one knew I was dealing with the mental health issues that I was. No one knew that I was escaping to Las Vegas or another degenerate playground three times

a month and having very bad behavior, because that's what allowed me to stop thinking about all my issues for a day or two. And so, it was, you know, and work was so busy, it was like, it was almost being managed to the minute. I remember I'd have, you know, my system would be like, you have a call, I'm going to start at 916 and at 922, I'm going to grab a used, you can go to this, it was like, that was my day. And it was just, it was truly crazy.

And so far as there was 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 that was a truly, truly crazy year. I mean, we, I don't know how many people we hired that year, we're opening up offices in London and then in the West Coast. And we, um, God, we opened up a massive gorgeous office in Chicago that we designed. Like, I designed every square into that place. And it was just. We had signed all our major accounts, like the BMWs of the world.

We designed the interior of one of their cars, like crazy stuff. So that was, that was the coolest period of my life ever, well also being the worst. One, which I think is often a worship in a nutshell. Absolutely. So here's something that I learned 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, I remember when we had to pull three all night, is in a row to get the project finished.

And we all did dominoes and you slept under the desk and this, like even the people listening who aren't an entrepreneur, you can remember completing an assignment for school or college or something. And 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, the goal of that or the, yeah, the proposed, the best outcome of that is to avoid going completely broke in one way or another, broke physically, broke spiritually, broke mentally, broke financially, you know, broke to jail, like judicially. Yeah. It's, yeah, you're spot on with that. And 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 in my mind first is not the money,

not like the day I became a millionaire, I barely recall it. I, some of 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 should have been, I think, a memorable day or maybe it was a big milestone. It's a big milestone, right? Yeah, you think so, except it was highly forgetful, forgettable for me compared to some of the tragic fucked up times that we had.

And there's this quote by my favorite author, Chuck Palinick, 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 actually, in those times, I think we're just great and things are happy. You don't learn a lot.

You're not really progressing. It really is those battles that you hopefully win when you really are in the best position you can be in. What are some of the lowest points that you can remember from that year? Well, the mental breakdown is pretty low. That was not right. Were you in the office? Was that a, you need to ring 911?

No, I was, I had just come back from a weekend in Las Vegas. That was highly inappropriate. That is also detailed in the first chapter. It's the intro to the book, yeah, exactly. The intro to the book. I came back from a bad behavior weekend, and anybody who's had that kind of weekend knows that you're in a fragile state, to say the least. And I proceeded to attempt to continue the weekend.

So I come straight back from weekend to parting to throw a party at my house. I had this ridiculous penthouse high rise in Chicago. It was towards the end of that, most people had left and I was there with a woman. We were getting ready to wind down. The best I can recall, and this has been filled in by her actually later on, but from what I recalled,

everything just kinda got kinda matrix-y. I kind of lost a sense of reality and the world kinda started to get kinda folding in on me. I'm like a little inception kind of perspective. And the last thing I was able to do was open my phone and call Kevin, who was my COO with the company. And as I, as it was ringing, I blacked out.

And according to her, I just felt like in the movies, just straight faint forward, slam my head on the ground. And she called 911. And I woke up in the hospital. My, I consciously woke up in the hospital three days later. Now I had been awake in the meantime, but I had no memory of that. I was in a completely disassociative state, which is not a place you want to be. And so it was a horrific time, and it was the first time I'd ever really confronted my

own existence, my own humanity. You know, there was a better than, you know, in ill-zero chance that I was never going to recover from that fully, and they didn't know with that many. It could have been severe brain damage. It could have been severe memory loss, some of which I do have. It could have been a stroke, they weren't sure at first. You know, it was a horrific thing to consider, you have, it could have been a stroke, they weren't sure at first. It was a horrific thing to consider that you almost died at age 30 after all of this

quantum-cote success, and it was awful. It was really awful. What did they diagnose as the contribution to that? Obviously, a bunch of substances and a high heart rate and a lack of sleep is going to contribute to that, but is it chronic long-term stress? Is it something else? Yeah, it's all of the above. And effectively, it's like a damn breaking in your brain. At some point, you've just put too much, you know, volatility, too much, you know, just pressure. And it's actually kind of fascinating. Like Like it wasn't at the time, but in reflection,

when it was explained to me, your brain, it's kind of a defense mechanism. So your brain is like, you know what, this isn't going well. And we're kind of, you know, we're feeling the damage of all this. And so we're gonna kind of just like, hit the reset.

And this is why it's called this is socially amnesia. Because when you disassociate, you're having a personality fugue state. And so your brain's kind of like this, this current state is damaging us. So we're just going to kind of put that off the side and almost start a new. And that's why, you know, a person in my state,

I didn't know my own name, didn't know what city I was in. I knew what a name was. I knew what a city was. I could list 10 cities. I just didn't have a clue which one mine was because I was learning a new identity for a few days. And that was the brain's way of forcing me to stop, which is somewhat incredible that your brain can do so. That is in space. That is so crazy. Yeah. And you'll see it, you know, I've obviously done quite a bit of research. And so if you

research like Fugue states, if you research dissociation amnesia, you can read, you know, and it's all at the back of a mental break of some kind, you know, and for me, it was a psychotic break, meeting out of suffering psychosis. And so for the weeks leading up to it, the one time I remember clearly, which is always weird to talk about, is I was watching television in my living room. For some period of time, I don't know if it's an hour, two hours, it's kind of mindlessly doing what we do, it's watching television. And then I realized the TV was off and had been the entire time. And I kind of was like, that is not good. And then you're like, did I turn it off? And you realize it was never wrong.

I was staring at a blank television, thinking I was watching TV for hours. And the most things that happened, and normally before a psychotic break, you have these moments of psychosis as you lead up to it. So there usually is some indicators. We generally don't notice them because it's just kind of like, it's so surreal.

But one of the reflected on it was I was like, yeah, there were a few warning signs. Were there? So, yeah. So looking back, obviously, we can armchair philosophies about the beauty of the newly awakened 36 years old understanding aligned genre. But would he, would the person sat in that chair today have been able to do what was needed 10 years ago?

Yes and no. If somebody had given me a crystal ball and they had said, as you start this company, here's where you'll be in five years. You'll be a rich man who almost died and you'll be pretty screwed up from the whole thing, but you will have technically succeeded. That would have obviously been shocking, but I don't think I would have had the wear with all to not 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 for instance, I was dating this wonderful woman named Courtney when the whole company started. I broke up with her in the second year because I convinced myself that I could not be a good partner 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 going to choose being an entrepreneur. And I now realize that's ridiculous. That's hogwash. Like 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. But with that said, if I were 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 used that as an anchor, maybe I wouldn't have worked as hard, maybe I would have been distracted. 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. 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 tech company, but secondly, it would just ways to be mentally acute, ways to stay attuned to your mind and body

throughout the entire journey to find methods of support, to have a good structure around, you need to be honest what you're dealing with, to seek therapy, I would do all those things now. And that, but that's looking forward. It's very difficult to say with looking back because at the end of the day, it worked. Who might have said that I should have done it differently

if it worked? So it's a that I should have done it differently if it worked. So it's a weird kind of place to reflect from. I understand. You think the ends justified the means by that logic? A little bit. And again, this is where it's hard to admit that because, you know, I had some pretty bad behavior and I'm not proud of what I did. And it was a pretty wild few years. I wasn't a very good son or brother or a friend of people. And so like, it's not that it justifies it, but at the same time, if you were going to go redo it, wouldn't you want the same result? And so it's kind of hard to say, like, you know, I would have, I would have been a better

friend, but I would happily have gone bankrupt. It's like, yeah, probably not. You know, like, so it's hard. It's very difficult to reflect on it from that way. And that's why for folks who have read the book or are gonna read the book, I worked very hard while writing it to not judge. I didn't want to say, like, oh, I wish I hadn't done this

or I saw 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, no pun intended. It's not a practical guide for what to do or what not to do. Yeah.

I think that's a really reassuringly unique viewpoint as stands that you've taken that very often it would be easy for someone to polarise their opinion for it to be, yeah, it was absolutely worth it. I know I definitely wouldn't have done it that way. I would have totally changed things around. I think that it's very reassuring to know that there's someone who's prepared to sort of go to that uncomfortable place of truth. 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, do you think on balance that more entrepreneurs are successful with or without partners if you take a normal distribution of entrepreneurs? More successful with partners, for sure. Based on stories I've heard, conversations that I've had, people are more successful with partners.

Why do you think that? I think it's quite obvious. I think it creates, assuming the relationship is healthy, right? I think that people can find themselves in some what talks through 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 living with every day. It forces you to not isolate, which is a very common characteristic of entrepreneurs. We lock ourselves in a room and hope for the best. If you're with somebody, you're not going to let you do that likely, at least not constantly. And so you're going to be pulled out of your element and forced to talk and forced to realize there's more going on than your little tech company. And I think that there's going to be a sense of compassion that you forget people will have

for you. One thing that I experience in my journey, and I've heard a lot from entrepreneurs, is that we kind of find ourselves in this like a shame spiral, kind of environment, where we're shameful for what we're doing and how we're spending our time, and we don't want to admit 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 a lot of hard decisions to make, and it's okay. And I would, you know, I would do the same thing. Even silly as it sounds, just hearing that would have done a lot for me. And I'm no 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, if there's some single entrepreneur, I can't be like, go find a find yourself a relationship. Yeah. That's hard. And then find, you know, that's ridiculous, but I can say off a lot of discussions with incredibly successful people that is more often than not a key. That's really interesting. I think that you are correct with that as well.

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, 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. And, you know, even stuff, even stupid things like

owning a dog, you know, like if you own a dog, you have to project that, you dissolve your sense of self-importance because there is something else and it's beholden to you. You need to look after it, right? So I think that's a really, really interesting insight. So, okay, we've had this crazy career. We've done also the learning and the reflection. Hopefully sufficient time for you to be able to 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? Honestly, this is going to sound... this is a horrible answer to your question, but I don't really have too many.

And the reason is because going back to the earlier point that you made, kind of of that 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 it's ridiculous. Like, you know, 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 and wrong ways, do things that other people do, because we generally have 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 I If I speak to an individual, if Chris and I, if we're having a pint in London and you're saying, hey, here's my situation.

Can you give me some advice based on yours? I'd happily do so. But I'm speaking to a room of entrepreneurs. And I say, here's three things you should do. Maybe 5% of those could be perfect for. 80% of it's irrelevant. And 15% I'm going to damage by them following my advice because everyone is so different. And so my lessons are purely my experience. That's why I wrote the book How I Wrote It.

It was very purposeful to not have takeaways, to not have lessons, to not have advice. It's just, here's what happened. And based on who you are and who every reader is, they're going to take away their own anecdotes from them. I think again, man, I'm really, really impressed with the anti-five steps to 10X your business like the... Thank you so much. Well, everyone that's listening will know that I have very strong opinions about Gary Vee and about Grant Cardone and about this like hustle porn,

a kind of success by any means mentality that we have going on at the moment. And again, like we spoke at the beginning about the fact that the Emperor kind of does have no clothes with regards to company valuations in Silicon Valley. I think that there is an intellectual cerebral equivalent, which is going on within motivation and success gurus at the moment as well. We could talk another hour about this topic. I actually think that that movement is quite

dangerous. And I think that it's probably not too dissimilar to the startups we talked about earlier. This quest for financial success and whatever else is driving a paradigm that is literally toxic and dangerous people who are listening and who are taking it quite seriously. Because again, you're speaking to a room of toxic and dangerous people who are listening and who are taking it quite seriously. Because again, you're speaking to a room of 2,000 people who are struggling to find their avenue forward. There's no such thing as blanket advice. There's literally no such thing.

And it's not just advice at that point. It's sometimes cultish level following. And I struggle with it a lot. And I talk out against it. And I actually did in the book. I think I won't repeat the line, but I am quite forward about my thoughts on the topic. And so, yeah, and that's why I try to do the exact opposite.

You know, I only know what I know. I've had one experience in my life, which is my life. I've had one timeline, done some things right, and things wrong. I'll continue to make mistakes. I'll continue to do stupid things. But at the end of the day, you day, I would embrace all of that and it would be very foolish of

me to try to cast any of that down as some unjust wisdom to somebody else. You are aware that that's a much more subtle approach though, and that in a world where absolute and polarisation is what seduces a lot of people that you are potentially sacrificing cloud and status and notoriety for this particular message. Sure. You know, the nice part about being where I am, and I apologize because I have to jump

for another podcast here in a second, but I'd love to continue it as well as at some point, if you wanna do a second part of this, but you know, one of the things that I'm very fortunate I'd love to continue it as well at some point if you want to do a second part of this, but one of the things that I'm very fortunate to have is I don't have the need for cloud and these kind of things. If I was worried about people loving me, I wouldn't have written the book I wrote because no one looks worse in this book than me.

I'm not exactly a quest for, let's say this is not an ego play, to say the least. And so I don't need to try to say the same things everyone else is to get more, you know, people re quoting me or something stupid. I believe in what I believe in. People who care to hear that and have that nuance will hear it, you know, from me. And those who need to be able to, you know, walk over coals and that's going to make them good a business can go do that. So dude, I love it. I really, really enjoy a much more subtle and nuanced approach to this. This sort of messaging, hopefully, is what we're going to see coming out of Silicon Valley more over the over the next decade. So a practical

way to get rich and die-triening, a memoir about risking it all will be linked in the show notes below. Anywhere else that people should go and check out, John? Yeah, my social is just John Roa, my name on Instagram and Twitter, don't use Facebook. And the book is available at all booksellers, I think across Europe as well as here in America. And then I have a podcast, it's currently called the John Roa show.

We're actually relaunching it with a really cool pivot in the next couple of weeks here. So you can currently follow the John Roa show. We're actually relaunching it with a really cool pivot in the next couple of weeks here. So you can currently follow the John Roa show and then when it pivots, you'll then have that feed. But yeah, and that's it. So Chris, I appreciate your time. you