Why Your Ego is Your Enemy (you can end up in Prison) - Riordan Maynard

24 Sep 2026 · 7 min · 5 chapters

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In short

Riordan Maynard argues that ego—especially refusing to accept failure—can drive business leaders into reckless expansion, financial mismanagement, and even prison. He links fear of failure to “keeping it going too long,” ignoring numbers, and moving money around when the business tanks.

Guest backgrounds

Riordan Maynard is a business leader who experienced a high-growth company collapse and later prison; he describes himself as a “vision” and sales/culture builder, not an operator for established businesses.

Key claims

fear sharpens performance but becomes dangerous when it turns into hubris; advice about capitalization and limiting growth was ignored; “build it and they will come” (inspired by Field of Dreams) replaced financial reality.

Notable examples

expanding to 52 offices; global financial crisis freezing budgets; using IRS money; “gambling” behavior of adding risk after small wins.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Fear of Failure and Ego's Role

0:00 to 1:10

Explore how fear of failure and ego can lead to poor business decisions.

“I spent my life fearing failure, which is really probably why I went to prison, because I refused to accept that the company was failing and I didn't want anyone to see me failing.”

Consequences of Ignoring Financial Advice

1:10 to 2:30

Learn about the dangers of ignoring financial advice during rapid growth.

The Illusion of Endless Growth

2:30 to 3:50

Understand the misconceptions around growth and financial management.

“And then you need the mind to actually accept that advice.”

Adrenaline and the Hustle Culture

3:50 to 5:10

Discuss the thrill of the hustle and its impact on business operations.

“When you say physically, what do you mean?”

Leadership and Company Stages

5:10 to 7:10

Examine the different leadership skills needed at various company stages.

“I probably should have a bit more sort of systems in place.”
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Transcript

Automatic transcript. May contain errors.

0:00Riordan Maynard:I spent my life fearing failure, which is really probably why I went to prison, because I refused to accept that the company was failing and I didn't want anyone to see me failing. So I basically kept it going too long. Use money from everywhere to keep it going. And then and then ultimately it did fail. But but I feared failure so much because I didn't want the ego, isn't it? Were you driven more? because I'm driven by a fear of failure more than like a... Oh, much more, yeah. A happiness of success. Yeah, I think most successful people are much more. Yeah, like, do you think you can actually build something without, like...

0:39Riordan Maynard:I don't think you can, actually. Yeah. Well, I don't know that. I don't know that. I mean, different people have different motivations, don't they? But I think fear sharpens the sword. Yeah, and lets you get through the shit. Yeah. But it also is dangerous because it makes you go too far. too far well in my case i i should have stopped and what what so what was why was it why was the business tanking at that point because the global financial crisis hit which was very consequential for well for every business really but we were dealing with a lot of the world's top companies and they froze their budget so a lot of the deals we were working on um just disappeared and we were growing super quickly at the time you know like 30 or 40 percent quarter on quarter and that was great when everything was flowing because you've got the cash flow to support it but when everything stops when the music stops you you notice that you don't have quite enough chairs wow that's what happened and so that's when i started sort of moving money around and that some of that money was irs money and um they weren't happy about that and then so then you've got this was it kind of like ego and hubris you think that you just you wanted just to keep on chugging you just didn't want to be seen to fail yeah it's total ego yeah well to get the the reason we got there in the first place was my ego thinking that we could keep expanding keep expanding keep expanding and you know not really taking any notice of the numbers um thinking that i knew better than everyone else and basically believing i was a i was midas you know i was a business god why not no and i genuinely thought you know when someone said to me actually probably don't need to own 52 offices this this week i would think in my head i think yeah okay okay yeah great yeah fucking idiot you know and you sort of get you develop this which is which but there's evidence to prove that previously what you have done has turned to gold yes but so i understand the hubris yeah you do get yeah it's a bit like i suppose it's a it's like gambling isn't it you you win a little bit and then oh okay i'll put a bit more on you and then oh okay i'll put And what you need is someone to say, hold on, take some off the table or keep it for a rainy day.

3:20Riordan Maynard:And then you need the mind to actually accept that advice. I had a lot of advice. You know, I was working with very capable people. And what was the best advice you ignored? Like in a sentence? Well, anything associated with capitalization. We were totally undercapitalized. and anything associated with growth, physical growth. Because I had an unlimited view of our ability to grow physically. When you say physically, what do you mean? I mean, more people, more locations. I said more offices. Yeah, so that you can support more business. yeah um and i i i had no link between that this is going to sound absolutely ridiculous i had no link between that and the finances right in my head yeah yeah yeah i i worked on the principle that if you build it they will come and that's because i had watched field of dreams with Kevin Costner.

4:32Riordan Maynard:And, and to be fair, it had worked to your point. It had worked. Yeah. But it was always edgy. I mean, we were always on the edge. I was always trying to find money. I feel like that was this. Yeah. Do you? Yeah. Yeah. Yeah. Like I'm constantly just like hustling like a mad fuck. Yeah. Just, but I like the buzz of it. It is like that. It's a fuck. It's adrenaline. It's like death metal. I couldn't do sitting there. My brother's a lawyer, and when he works from home, I see him on these Zoom calls, and I don't have any fucking Monday meetings. I'm like, let's go, right? Get on. And it's like, so how was your weekend?

5:13And so then let's go for this report. And it's just like, it's quite... I probably should have a bit more sort of systems in place. Well, you will. Yeah, I don't know. No, you will.

5:24Riordan Maynard:It was boring, though, isn't it? Well, if you grow, you will. That's one of the downsides of growth. Yes. It is. Yeah, it takes the fun out of it, doesn't it? Yeah, well, it's a different, it's just different. That's the other thing, the other, that's one of the things I've learned, is that there are different people for different stages in a company's life. I'm really good at the beginning and maybe just the little middle bit, but I'm no good once it's established. you should really just fire me there and then because I'm not good at the run you know the the managing of an organization is a real skill you know and I um within touch base we had some really brilliant operators brilliant and they were really responsible for the success of the company um I was just very good at putting a vision together, articulating that vision, getting people to get excited about it, getting clients to buy into it.

6:31Riordan Maynard:Sales. Everything is sales. And leadership and setting the culture of the organization. But I should have, it's always easy to look in retrospect, I should have definitely handed it over to someone who knows, You know who really got joy out of running a business and there's lots of those people you know Those are the people you see running these extraordinary big companies and it's quite unusual for For a starter to be to be able to do the Later bit. Yeah. Yeah. Yeah. Some people can I mean you look I suppose But it's unusual

From the publisher

Did Riordan's ego land him in prison?

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This episode was edited by: G.Thomas Craig (https://www.linkedin.com/in/gthomascraig/) 

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