When Matt Schmeltz and his partners acquired CloudCraze, it was a simple software application helping businesses that use Salesforce.com manage their customer relationships. CloudCraze generated $2 million in annual recurring revenue, but Schmeltz & Co. figured it could do much more.

In 1995, with just $5,000 in start-up capital, Ashok Vasudevan launched Tasty Bite offering ready-to-eat Indian entrees to American consumers.

Twenty-five years later, Tasty Bite is America's largest brand of prepared Indian food sold everywhere, from Walmart to Whole Foods. In 2017, Vasudevan announced he had sold the company to Mars, which has a portfolio of beloved brands including everything from Uncle Ben's to Skittles.

Peter Demangos has started two businesses in the Human Resources sector. One was a bootstrapped insurance brokerage where they sold employee benefits programs to large clients. The other was an HR software company called Collage, where Demangos and his co-founders raised $3.5 million of investment capital and sold three years later for $15 million. 

Debbie King was running on a treadmill so familiar to service company owners. Her company, Association Analytics, helped associations make sense of their member data, and she was wasting time on proposals that often did not get accepted. Then, when King did win a project, she was creating a custom solution for every job that required her to hire senior-level staff and personally get involved in client work. The model put a cap on her business, and when she reached 20 employees, she decided it was time to get out.

Lee Gregory built Sir Lines-A-Lot, a company that paints lines on highways, to 40 employees. It was blue-collar work, so when Gregory learned his company could be worth north of eight figures, he decided it was time to sell. During this interview, Gregory