PE Shut Down Her Business. So She’s Starting Up Again (At 60)
The first time around, Sharon Gillenwater documented how she made more money by bootstrapping her software-as-a-service marketing firm than she would have by taking venture capital.
Good Morning!
Here are today’s highlights:
The job-hugging trend isn’t necessarily a win for employers.
Southwest is introducing a new boarding plan, and it’s a little complicated.
Last year, the now-shuttered SBIR and STTR programs steered $4.7 billion to small businesses.
Walmart shoppers will be able to do their shopping through ChatGPT.
ENTREPRENEURSHIP
Sharon Gillenwater explains why she decided to jump back into “the meat grinder”: “While most people were enjoying the last of the summer, I was sleepless, night after night. Not the good kind—the kind where you’re so excited about an idea that your brain won’t shut off. No, these were the anxiety-ridden, 3 AM, staring-at-the-ceiling kind, where you question everything and wonder if you’re making the biggest mistake of your life. For two months, I wrestled with a decision that seemed completely insane to many people: Should I rebuild my company? I’d already had my exit. I’d already proven I could build and sell a business. I was financially secure. I could travel, invest in other founders, write a book, speak at conferences. I could enjoy the fruits of 14 years of hard work. So why would I even consider jumping back into the meat grinder? The doubt was crushing. I’d lie awake running scenarios, questioning my motivations, wondering if I was about to throw away the peace and security I’d worked so hard to achieve. But then something shifted.”
“After weeks of calls with customers, former colleagues and vendors and industry experts, I made a decision. I was going all in. Not tentatively, not with a bunch of conditions and escape hatches, but fully committed. And just like that, the anxiety disappeared. In its place was something I hadn’t felt in a long time: pure excitement. The kind of energy that makes you jump out of bed in the morning because you can’t wait to get to work. I haven’t been this happy in years.”
“Building a company in 2025 is a completely different ballgame than it was when I started Boardroom Insiders in 2008. The landscape has transformed in ways that make me genuinely excited about the possibilities. Some of the biggest differences: Building is democratized: AI tools, no-code platforms, and cloud infrastructure mean you can build sophisticated products for a fraction of the cost. Information abundance: APIs, web-scraping, and AI can gather and process information and complete tasks at unprecedented scale and speed. Rapid experimentation: Modern tools enable daily iterations. You can test ideas in hours, not months.”
“So I did something that felt both natural and terrifying: I started leaning on the very entrepreneurs I’d been advising. I scheduled regular calls with founder friends who were deep in the trenches of building. During my own office hours (when time allowed—I wasn’t about to monopolize the sessions meant for others), I’d slip in my own questions about today’s tools, strategies, and approaches.”
The backstory: in this remarkably candid 21 Hats Podcast, Sharon explained how she sold her business and exactly how much money she made. READ MORE
