Cameron Herold reflects on the difficulties of being a CEO and the untold operational struggles entrepreneurs face (near-bankruptcy, fraud, lawsuits). He describes his move to Dubai and tax-free residency as part of designing his life, outlines a selective approach to paid speaking (strategic/Highly paid engagements or tied to his travel), promotes his book The Second in Command about empowering COOs, and explains his COO-focused podcast (started ~8 years ago, ~500 episodes) which interviews COOs to reveal the operational side of scaling companies.
Questions this video answers
800 paid speaking events
29 countries
Dubai
Started ~8 years ago; about 500 episodes
The Second in Command
Chapters
It's hard as the entrepreneur to talk about almost bankrupting the company or when a CFO is stealing from you or being sued or just the operational. How hard it really is to grow something. It's not a story that people necessarily tell when you're the CEO, but it's a true story that there's a lot of lessons there. I'm now no longer resident of Canada. I'm a resident of Dubai. My company is based in Dubai. So I've now hit kind of an economic free zone that I don't pay tax anymore. Legally, I'm above board, tax free, where I don't pay personal tax, no capital gains tax, no dividend tax, and my corporate tax is now so low because they just introduced corporate for the first time. So I think this kind of like economic trajectory where the compounding is just so massive. So I would tell people to look for ways to and places to have life by design. That many of us ended up where we're living because our great grandparents or our grandparents moved here. But we can live anywhere and be anywhere and be global. You know that that's something to consider. But I think the big one is none of this matters. The death rate is still 100%. Like we're all going to die, right? I actually got a tattoo back in June and it's the Ram Dass quote. This one's in Hindi, but it says walking each other home. And it's just a reminder that none of this stuff matters. This is just what we're doing to make a buck and take care of each other and have fun along the journey. Because at the end of the day, we're all going to die. And I think that many people lose sight of that, that this is just one journey that we get. And let's have the best journey we can. I've done 800 paid speaking events in 29 countries. But I was doing that back in the earlier days to scale my brand and to scale my business. Now I'm saying no to those unless they are very highly paid or unless they're very strategic audiences or unless they're with groups that really I can kind of do some cool stuff in. Like if I can go to Antarctica to speak, I'll say yes. But if it's just another speaking event in Chicago for a normal group, it's going to be a no. But I do a lot of speaking now over zoom too. I have groups that pay me to do 60, 90 minute talks over Zoom. But I did two speaking events in January in Dubai. I had one in February in Peru. I did one in Ibiza last year. But I was going to be in Ibiza anyway. I was going to be in Cairo last December. So I reached out to the Cairo EO and YPO chapters. They said yes, they paid, they booked me. I spoke in two, two events in Melbourne, Australia this year. But I was going to be in Melbourne for all of Fembor anyway. So I think because my grand has gotten big enough now and my connections are big enough, I can strategically reach out to places in advance and land some. That's more of the speaking that I'm doing now than saying yes to the groups that book me. If you haven't read my newest book, the Second in Command, go grab a copy right now on Amazon and you'll learn how to unleash the power of a coo. And if you already are a coo, you'll learn how to really build an incredible partnership with your CEO. My podcast, I started eight years ago. We've had about 500 episodes. Now, we only interview the COO of companies. And I did that because I wanted the rest of the story. I know Guy Raz, who runs How I Built this. We've hung out a bunch of times at the main TED conference, and he interviews these CEOs, entrepreneurs of companies. And I often know the CEO and I know the rest of the story that they're not sharing. It's hard as the entrepreneur to talk about almost bankrupting the company or when a CFO is stealing from you or being sued, or just the operational how hard it really is to grow something. It's not a story that people necessarily tell when you're the CEO, but it's a true story that there's a lot of lessons there. And it's almost like if I asked your mom and dad, how did you raise Kevin? Your mom would have a very true story. Your dad would have a very true story. But they'd be different stories. I just wanted that different story at how to scale an organization. So we started interviewing COOs of some of the world's top brands. You know, I've had the Samac, Kajabi, Trainual, Shopify, Cleveland Indians, like Bumble. I've interviewed the COOs of all these brands to hear their side of scaling up the story and to learn how do we make the CEO iconic. The Sheryl Sandberg. Sheryl Sandberg was the COO to mark Zuckerberg for 15 years. In the early days, she was the adult in the room, you know, and then she became a little bit of the mentor, and then she became a little bit of the guard. What was her role like and how did she continue to grow as a coo? So that's what the Second Command podcast is about.
