Should You Plan for the Exit When You Start Your SaaS Company?

When you start your SaaS business that you eventually want to sell, should you have a theory about who will buy your company?

Most tech investors will tell you not to think about your eventual exit so specifically. Just take the funding and grow big fast.

But some SaaS startup advice is designed just for companies with big outside funding. Their advice, particularly about fast growth, funding, and exits, can be misguided or dangerous for bootstrappers and practically-funded SaaS companies.

I discussed this important question last week with Gregory Shepard, a serial entrepreneur who has created and sold 12 companies, including marketing software and ad technology companies.

In 2016, he sold two of his bootstrapped software companies, AffiliateTraction and AdAssured, to eBay for an undisclosed “huge” amount of money, as he describes it.

Gregory’s advice for practical SaaS founders often contradicts the advice from startup advisors and funders:

“If you’re going to sell your business, you have to know who’s going to buy it and plan for that exit. Investors say, ‘Oh, no. That’s later on you can’t do that.’

“I think that’s ridiculous. Because an acquirer is another business with a specific synergy. A synergy, which is the reason why an acquirer would buy you, is either to save or make money.

“If that’s the case, then your whole business is just a product to your acquirer. Not planning your acquirer when you build your business is like building a business without having a customer.“

That’s one way to do It that worked for Gregory–12 times successfully. In every business he grew up.

This unusual advice comes from an unusual entrepreneur. Gregory faced monumental challenges as a child growing up in poverty with a rare combination of autism, dyslexia, synesthesia, savant syndrome, and other neurodivergent conditions.

He learned to develop himself and overcome big challenges, including creating, growing, and running many software companies over three decades.

Gregory sees patterns in data that nobody else can see. It’s a superpower that helped him create some massive businesses with these insights.

Gregory shares his incredible entrepreneurial journey and more insights on the Practical Founders Podcast this week.

It’s an amazing personal story with great insights and advice for practical founders. Thanks for sharing your story, Gregory!


Get the weekly Practical Founders email and podcast update.

Share Practical Founders


Win the Startup Game Without VC Funding

Learn how all 75 founders on the Practical Founders Podcast created an average founder equity value of $50 million.