What is your Entrepreneurial Appetite?

In this episode of Business Brain, Shannon Jean and Dave Hamilton dig into the hard lessons of selling a business — and how we can protect ourselves when a deal falls apart. Drawing from their own experience with a failed acquisition of Deals on the Web (where they mentally checked out and let a thriving business fade), Dave breaks down the power of a cancellation clause. We learn that when a later buyer offered to cover growth costs during due diligence — with the sellers keeping everything free if the buyer walked — it changed the game entirely. The takeaway: if we’re fielding acquisition offers, we need to bake in protections that keep us motivated and compensated while the deal is in play, because selling a business is a job in itself.

Then Shannon floats an idea he’s been cooking up: an entrepreneurial appetite quiz designed to help aspiring business owners figure out if they’re truly wired for the grind. We’re talking risk tolerance, the need for a guaranteed paycheck, and whether we’d rather ride a roller coaster than bet ten grand on ourselves. It’s not about age or experience — it’s about knowing our own appetite before we jump in. Shannon plans to build it out and share it with listeners, and Dave ties it all together with a reminder to keep living that Charmed Life.

• 00:00:00 Business Brain – The Entrepreneurs’ Podcast #744 for Wednesday, April 15, 2026
  • April 15th: Tax Day
• 00:01:35 The benefits of putting a cancellation payment/clause in your acquisition agreement
  • Incentivizes the deal
  • It’s a litmus test to see if everyone is serious
• 00:11:46 SPONSOR: Whatnot is the largest dedicated live shopping platform and, for a limited time, Whatnot will match your first $150 sold in the first month. Visit https://whatnot.com/sell to start selling.
• 00:13:19 SPONSOR: Fundera from NerdWallet – A free, easy-to-use platform that lets you compare real financing offers from trusted lenders — all in one place. Visit https://NerdWallet.com/BRAIN to learn more and talk to a real person!
• 00:14:43 What’s your entrepreneurial appetite?
  • Finding out your entrepreneurial aptitude and preparedness
  • Workshopping questions:
    • Do you need guaranteed income?
    • Do you mind working on a Sunday night?
    • What’s your risk profile?
    • Rollercoasters vs. a million dollars
• 00:20:31 Business Brain 744 Outtro
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