Dana Miranda

The 20-something serial entrepreneur was ready to build something new after growing his fourth company. He tried to sell on a marketplace, but ended up finding the right buyer by reaching out directly.

This founder had years of exit-prep experience, but selling to a public company was a brand-new challenge.

This bootstrapping founder wasn’t seeking a sale, but a fortuitous partnership led to an unexpected offer.

User feedback helped these entrepreneurs pivot toward the employee referrals niche. But then they faced another challenge: the pandemic.

Instead of selling her company, The Fertility Tribe founder Kristyn Hodgdon joined forces with a tech startup to launch Rescripted, a fertility treatment platform and community.

Gabe Murillo scaled PodcastPress, a podcast production service, to 200 clients with the help of startup accelerator grants and paid media.

Founder Grace McBride conceived of TripKit for a class project at Cornell and saw enough demand to build the business. Three years later, she and her co-founder sold the company.

How should you prepare for a personal windfall ahead of selling your business? Here’s what to think about before the money hits your bank account.