Aaron sits down with Kim Whitaker, a seasoned entrepreneur and hospitality innovator, to unpack her journey from building Once in Cape Town into a thriving hospitality brand to executing a successful exit. In this episode, Kim shares the realities of growing a business, structuring an investment deal, and navigating the sale of a hospitality company—during COVID, no less.
She discusses the pivotal moments that shaped her exit strategy, the value of strategic lease negotiations, and key learnings from the sale process. Kim also reflects on the emotional journey post-exit and the identity shift that comes with stepping away from a business.
KEY TAKEAWAYS:
- Negotiation Strategy Wins – How Kim leveraged multiple offers and structured a lease extension to maximize exit value.
- The Texas Auction Clause – A lesser-known but powerful contractual safeguard that ensures buyout offers remain fair and competitive
- Avoiding Costly Legal Oversights – The single word buried in her contract that cost her significant value—and how AI or a sharp legal team could have caught it.
- Life After Exit – The unexpected challenges of finding purpose post-exit and the importance of preparing for what comes next.
BEST MOMENTS:
- “The Texas auction clause was a game-changer—it ensured any buyout offer had to be fair.”
- “Our lease was the most valuable asset in the deal. Extending it added millions to the sale price.”
- “I underestimated the emotional impact of exiting. You spend years building an identity around your business—what happens when it’s gone?”
- “Your exit is won or lost in negotiation. If you don’t create competition, you’re just a price taker.”
- “Post-exit, I realized there’s a gap—founders aren’t prepared for what happens next. That’s what I’m researching now.”
FIND US ON:
