For many founders, building a company from the ground up is deeply personal. The business becomes an extension of their identity - their ideas, energy, and long nights transformed into something real. But as growth accelerates and complexity sets in, the question emerges: Should a founder remain CEO forever, or is there a point when stepping aside actually serves the company better?
That’s the dilemma Milind Katti, CEO at DemandFarm, explored in his recent appearance on Wisdom From Wizards, the show where business leaders share hard-earned lessons from their journeys.
Milind believes that the early stages of a company demand a unique kind of leadership: “The initial skills of an entrepreneur - innovation, hustle, and fun - are what get you off the ground.” Founders thrive in chaos, willing ideas into existence with passion and creativity.
But as the business matures, that same chaos can become a constraint. “After a while,” Milind shared, “that scaling needs to be done by a professional CEO.” Growth now requires structure, systems, and scale - not just grit. The qualities that once drove momentum can start to hold the company back if the founder doesn’t evolve or recognize the need for a different kind of leadership.
What struck me most about Milind’s insight was his humility. “We should not have the ego to continue forever,” he said. Many founders wrestle with the idea of stepping aside because it feels like losing control. But Milind reframes it: knowing when to hand over the reins isn’t weakness - it’s wisdom.
It’s about asking, Do I still have the hunger? Do I still want to do this? When that inner fire dims, clinging on can hurt both the leader and the business. Great founders, he suggests, recognize when their company’s next stage requires someone else’s strengths.
Interestingly, Milind also touched on something rarely discussed: founders often evolve personally, too. “At some point, you start developing other interests,” he said. “That gives you more calling than what the business does.” For many, the next chapter might be mentoring, investing, or building something new.
Stepping aside doesn’t mean stepping away from impact - it means channeling your experience toward new opportunities for creation and contribution.
If your company is in the $1M-$5M range, you’re likely approaching this very crossroads. Growth is accelerating, but so are the demands. The systems, people, and pace required to scale may call for a new kind of leadership - whether that’s a COO to complement your strengths or, eventually, a successor to expand your vision.
As Milind’s reflection shows, real leadership isn’t about holding on; it’s about knowing when to let go.
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Key takeaway: The best founders don’t cling to titles - they focus on what the company needs next, even if that means stepping aside so it can soar higher.