Why Risk Takers Build the Most with Doug Holladay, Author of Rethinking Success

The most accomplished who have actually done so much better than their parents, and they're sitting on some, however you measure success, some kind of success, what they wanna do is protect their children from the very things-

100%. [laughs]

... that, that made them amazing. Everything in modern society now is creating guardrails so our kids can't figure out life. So we are protecting them from the very pain, setback, hurt that could make them a LeBron James or could make them a Howard Schultz.

[upbeat music] Welcome to the Revenue Builders Podcast, a weekly show featuring B2B sales leaders and executives, hosted by five-time CRO John McMahon and Force Management co-founder John Kaplan. The show takes guests in the barrel, behind the scenes with the people who've been there, done that, and seen the results. Revenue Builders covers best practices for scaling and growing your business while sharing the pitfalls to avoid.

Today's guest is Doug Holladay, who's back with us for the next installment in our series on his book, Rethinking Success. In our last conversation, we explored humility and the art of letting go. This time, we're looking at two practices that build directly on each other: defining success and failure for yourself, and inviting risk into your life. If you're just joining the series, Doug has had one of the most varied careers out there: public service, international finance, private equity, and now he's the founder of an organization called Path North, where he helps CEOs and business owners broaden their definition of success. In this conversation, we ask the question most sales leaders never stop to ask: whose scorecard are you actually playing by? And why do the sales leaders who take real risk, not reckless ones, but real ones, end up building the most? These conversations with Doug are so good. Let's take a listen. So Doug, it's so great to have you back. Um, today we're gonna continue with thoughts on the incredible book that you, that you provided, you know, the world in Rethinking Success, and we're gonna talk about chapter six and seven today, which is around defining success and, and then failure for yourself, and also the concept of how risk plays-

Yeah

... a, uh, plays a, uh, uh, a significant, a significant role in that. What I, I've alwa- you're such a amazingly [laughs] talented individual with an incredible story. You know, I don't know if I've ever asked you this, but, like, when you were growing up, I know what you've done.

Yeah.

When you were growing up, how was, uh, success defined for you when you were growing up? And, and how did that manifest itself into what happened for you?

Well, it's interesting. My sister and I, if you met her, we're almost bookends. I mean, she's been in fashion with Vogue and raised her family in San Francisco, and she, but she's definitely out of the box and like me. And I think we've talked about it. We had a father who was a finance guy. He was a trained-

Yeah

... uh, accountant, all that, really in the box, but he had a creative streak. But my mother was kind of this magical, you know, visionary dreamer, just believed that anything is possible. Every breath I took was the greatest breath