Last week, I attended the first partner event of a startup I’ve been involved with for over a year—as one of its very first angel investors. During one of the discussions, someone said a sentence that stopped me in my tracks:
“Founding a company is less risky than joining one.”
At first, it sounded completely counterintuitive. How could starting something from scratch—with no customers, no product, no certainty—be less risky than stepping into an already operational business?
But the more I’ve reflected on that statement, the more I’ve realized how much truth is packed into it.
The Illusion of Stability
When people consider joining a company—especially one that’s already up and running—there’s a natural tendency to equate it with stability. There are existing clients, revenue streams, team members, perhaps even processes and policies. On the surface, it seems safer.
But safety is an illusion if you don’t have the power to influence key decisions, shift direction when necessary, or design the system you’re operating in. Joining a company means stepping into a structure built by others. Even if you’re brought in at the top—say, as CEO—you still inherit a complex web of existing dynamics, culture, relationships, and often, constraints.
And that’s where the risk quietly resides: in the limitations you didn’t choose but must now navigate.
The Founder’s Paradox
Founding a company, on the other hand, is often perceived as the riskiest move. You’re responsible for everything—strategy, hiring, product, funding, and execution. You build from zero. You face a thousand unknowns.
But here’s the flip side: you also have full agency.
You choose your co-founders and your team. You shape the culture. You set the course. You can pivot when something isn’t working. You’re not bound by legacy decisions or outdated systems. The risk is undeniable—but it’s a calculated risk because you’re the one doing the calculating.
And that’s the essence of why it can be less risky. You’re in control.
Adaptation vs. Autonomy
Even the most capable leaders, when joining an existing organization, face the same challenge: adaptation.
You have to understand the unwritten rules, navigate the established power structures, and often compromise your vision to align with what’s already in place. That’s not necessarily a bad thing—it’s just the reality of stepping into someone else’s world.
The higher your role, the more responsibility you carry—but paradoxically, that doesn’t always come with more freedom. You might be hired to lead transformation, yet find yourself constrained by invisible guardrails.
And that’s the distinction: founders operate with autonomy, joiners operate within adaptation.
A Personal Reflection
As someone who’s been a founder, a CEO, an advisor, and an investor—I’ve lived both sides of this. I’ve felt the adrenaline of launching something new and the complexity of stepping into leadership within existing organizations. Both journeys demand courage. But only one gives you a blank canvas.
That quote—“Founding a company is less risky than joining one”—has stayed with me, not just because of its boldness, but because it reframes how we think about risk itself.
Final Thought
Risk isn’t about the unknown. It’s about how much power you have to shape what happens next.
That’s the kind of risk I’ll choose, every time.