In hosting my recent event for founders, “The Other Side of the Exit,” I noticed that a high percentage of those who took an interest were actually founders who were working on the second or even third exits. In talking to these founders and my clients, it has become clear that first-time and serial founders are on different journeys. They also have different definitions of success.
1. The First-Time Founder: Managing Stress and Self-Doubt
First-time founders are often overwhelmed. Like a new parent who worries about every little cough, these founders stress over every decision. They wonder if their product is good enough, if their team is right, or if their company is growing fast enough. And they wonder if they are up to the task of growing and potentially selling a company, even when they know their idea is a solid one.
The first journey of the first-time founder is about selling their idea with confidence. To customers, to other employees, to investors.
If they do their work well and find a good product-market fit with a decent TAM, the task shifts from doing more to doing less. The process of scaling a company is about hiring people who are smarter than you and letting them run with less and less guidance from you. For someone who, to this point, has done it all, this can be terrifying.
Success to this founder is simply getting to the point of having a sustainable, perhaps even sellable business. And what they are most looking for isn’t deep personal development, it’s just knowing that others have gone through similar struggles and come out the other side. It’s about staying strong under pressure and having the advice of those who have gone before.
As Founder Michael McAllister pointed out in my event, “The entrepreneurial journey is a personal journey as well.” For the first time founder this journey is about capability, and confidence, and calm in the face of possibly more stress than the founder has ever felt.
2. The Seasoned Founder: Creating with Purpose
The seasoned founder has been through an exit or maybe even two. They know what to expect and not to expect from an exit, and they’ve already experienced the highs and lows of building a business. They’ve learned that success isn’t just about money or public recognition—it’s ultimately about learning what brings them personal fulfillment, and doing more of that.
There’s a saying in the founder world. “Builder’s build.” Meaning that the founders who find out that the money didn’t make them happy are unlikely to go through it again. And the founders who found out that the money DID make them happy are unlikely to go through it again, either.
The founders who do it again are those who learn that for them, the reward, the thrill even, is in the journey of creation. The rewards are incidental.
For these founders, the questions are different:
“How can I create from a sense of purpose rather than need?”
“How do I enroll others in a meaningful vision?”
“How do I create from my unique zone of genius and let others do the same?”
For these founders, the reward is not the money or the sale or the IPO. It’s the joy of creating something of value in every sense of that word.
3. The Journey Beyond Founder
At some point, even a serial founder decides to hang it up. I have had clients who used this time to explore a spiritual path, to advise others, to give back in whatever way makes the most sense to them.
This founder needs support of a different type, while also supporting others. Regardless of their age, these are the “elders” of the founder community, and the source of great wisdom even as they continue to learn.
Which Founder Are You?
I’m creating a community of founders who can help each other no matter where they are in their own founder journey. There will be a place for everyone from those who are still in stealth mode to those who are focused on their post-exit journey.
My event on September 17 was just the beginning and I would love to have other founders help me shape what this community looks like and all the ways that we have of supporting each other.
I’m creating an email list to share ideas and keep people posted on new developments. If you’d like to be included, please comment below or send me a DM.