A Silicon Valley Bootstrapper Tells All

Even Sharon Gillenwater, who sold a relatively small business, was surprised to learn that she fared better than many venture-backed founders.

Good Morning!

Here are today’s highlights:            

• Salary budgets are expected to grow by 3.9 percent in 2025.

• The predatory pricing of many lifestyle brands may be coming to an end.

• Here’s how to get a grip on company expenses before things go awry.

• On the 21 Hats Sounding Board, owners discuss how a falling stock market affects their businesses.

THE 21 HATS PODCAST

This week, special guest Sharon Gillenwater lets us in on some dirty little secrets about Silicon Valley: She’s the founder of two businesses. The first one was backed by venture capital and then destroyed by venture capital. Despite that experience, Sharon tried to raise capital for her second business, Boardroom Insiders, a software-as-a-service marketing tool that helps businesses sell to the top decision-makers at big corporations. But this time, the VCs weren’t interested. So she bootstrapped the business with the help of an angel investor—and proceeded to learn some surprising lessons, many of which she shares in her book, Scaling with Soul.

• Perhaps the biggest surprise came when she sold her business and learned the happy lesson that the founder of a relatively small bootstrapped business can walk away with more money than the founder of a venture-backed business that sells for far more. 

• In our conversation, Sharon is unusually candid about what it took to build her business, what she learned about B2B marketing, and precisely how much money she made along the way.

• You can subscribe to the 21 Hats Podcast wherever you get podcasts.