After a founder sells their company, how long does it take before they can work on their next startup adventure? This depends on how they sold their company.
If they sold a majority stake to private equity buyers, they would still retain some ownership and likely continue running the company. These transitions take years.
If they sold the whole company to a strategic buyer, they might help in the transition, but they usually make a clean start in months, not years.
Shailesh Hegde is the CEO of Hubilo, a Bangalore-based webinar software company that initially started during COVID as virtual events tech and raised $150 million in VC funding before the market shifted.
Initially joining Hubilo as head of product, Shailesh stepped into the CEO role after returning all remaining capital to investors.
When the virtual events boom collapsed, Shailesh and the team rebuilt Hubilo into a mid-market webinar platform serving B2B marketing teams.
They shifted from large in-person event organizers to marketers running frequent webinars, emphasizing differentiated AI-driven content repurposing.
Hubilo stabilized revenue, rebuilt its GTM motion, and achieved a 50/50 split between new webinar revenue and legacy customer revenue.
Earlier this year, Hubilo was acquired by BrandLive, a U.S. enterprise video platform seeking a complementary webinar product.
About 80% of Hubilo’s team moved over, and Shailesh now leads product integration and customer continuity during the transition.
Like most founders who successfully exit, he’s already starting to think about his next startup adventure:
“Now that I just sold our company, I’m thinking about what’s next for me. It comes down to: will I be able to find a viable problem that people are willing to pay for, and will I be able to use all of this experience to solve it really well and kick a company off the ground?
“Now is probably the best time to start a company where there’s so much action, there’s so much happening in AI, and it’s super exciting to be in this space. It’s also a great time not to have all the revenue pressure on your shoulders, to think out loud, have open conversations, and just be free before you really dive in and choose a focus.
“The same types of business pressures will come back as you start a company. But now is a great time to help with our transition, make sure the team is good, but at the same time, start thinking about the types of problems I want to solve in the future with a new startup.”
Shailesh is excited to find the right problem to solve now that the AI revolution is underway.
Founder-market fit + timing. Both matter a lot.
Check out this practical interview with Shailesh Hegde on the Practical Founders Podcast.
