From $250k Raised to a $1.25B Exit with Shegun Otulana

A few weeks back, I was the morning speaker at an event hosted by David Senra of FoundersPodcast (one of my favorite podcasts and people). The afternoon speaker was someone I’d never heard of before, Shegun Otulana. The story he told resonated deeply — a Nigerian immigrant who came to study at the University of Alabama. He had the drive to be an entrepreneur and had a few early attempts that ended in a failed partnership and a pile of debt.

Feeling like he was made for more than pushing pixels at a 9-to-5, and at the urging of his wife, Shegun set out to find a problem he could solve and eventually build a business around. A chance encounter led to meeting the head of a mental health clinic in Birmingham, AL. They needed a new system to run their practice but none seemed to fit their unique needs. After failing to find them something he could help them buy, Shegun built them a simple app. That simple app led to feature requests, which led to his first paying customer and then the word of mouth began to spread.

Within 5 years, after only having raised $250,000 from local angel investors and with no experience in the industry, that side project had become a thriving business doing north of $50M in ARR and was valued at hundreds of millions of dollars. Along the way, he has able to bring in PE investors and de-risk his personal finances with several rounds of secondary. He eventually sold the business to KKR in 2021 for $1.25B, making it the largest tech exit in Alabama.

Some takeaways from this one:

— Shegun built a successful healthcare software company through disciplined, customer-obsessed growth. Their approach centered on deeply understanding customer problems at counseling centers and building the initial product based on direct feedback. They found differentiation through an innovative pricing model aligned with customer needs and an SEO forward sales motion.
— Starting with just $250,000 in initial funding, Shegun grew the business to over $50M in revenue within 5 years, eventually selling to KKR for $1.25 billion. Shegun emphasized fundamental business principles rather than chasing fundraising hype. The company maintained strong financials with 30% profit margins and 90% gross margins, growing organically without requiring additional capital on the balance sheet.
— Shegun’s leadership philosophy focused on creating a culture of transparency where team members could be vulnerable while maintaining high standards. He built a distributed team to access talent cost-effectively and gave team members significant autonomy within clear guidelines.

At the conclusion of his talk at Senra's event, we both met in the hallway and gave each other a big hug. It was like finding someone who was a part of your tribe — speaking your same language and sharing your same values.

When we realized we’d both be at the Main Street Summit the following week, we decided then and there to get his story recorded. The MSS organizers were kind enough to turn over their main stage theatre for us to record in after hours and I think the resulting conversation and visuals make this one you can't skip.

I hope you enjoy listening as much as we enjoyed recording it.

As always, if you or someone you know is working on something that could be a fit for indie, don't hesitate to reach out.

Bryce