Shegun Otulana is a seasoned entrepreneur, advisor, mentor and investor. Drawing from his experience as a bootstrapped startup founder who found incredible success, his mission is to empower the next generation of builders by sharing his lessons learned to guide their entrepreneurial journeys. In addition to mentoring founders in his community – many of whom have gone on to launch successful companies – he also enjoys sharing his insight with startup leaders, business associations, academic institutions and other growth-minded groups.
In 2013, Shegun founded TheraNest and its parent company, Therapy Brands, a software platform for mental, behavioral, substance and physical rehab providers and organizations. In 2021, he exited the business for $1.25 billion, the largest software exit on record in the state of Alabama.
Prior to establishing Therapy Brands, Shegun founded Zertis Technologies, a computer software consultancy company. Today, he continues his “idea lab” approach as the Founder of Harmony Venture Labs (HVL), an idea and growth studio that owns and operates a family of technology companies.
In this powerful episode of From Start-Up to Grown-Up, I sit down with Shegun Otulana, who bootstrapped his way from Nigeria to building a $1.25B healthcare tech company in Birmingham, Alabama.
What struck me most about Shegun's journey?
➡️ The power of constraints as blessings - limited funding forced profitable growth from day one
➡️ Culture needs rituals - it's not enough to have values, you must memorialize and celebrate them
➡️ Leadership growth requires vulnerability - others see you differently than you see yourself
One of my favorite insights: "Your nature is your nature, but you need to find people who complement what you don't bring to the table."
Shegun openly shared how he learned to build strong remote teams by finding cultural champions when that wasn't his natural strength.
When Shegun could only raise $250,000 in 10 months for his healthcare SaaS company, he turned that constraint into motivation.
Without the luxury of burning cash, he had to build profitably from day one.
Rather than seeing limited capital as a barrier, he viewed it as a blessing that forced disciplined growth - a mindset that ultimately led to a billion-dollar exit.
It's about intentionally designing incentive structures that make your team feel safe to experiment and learn.
Learn more about Shegun | Website
https://shegunotulana.com/
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