If you've ever thought about selling your business or investing in one that might be sold down the road, this episode is for you.
In this episode of The Compassionate Capitalist Show, I sit down with Rob Levin, Managing Partner at CIS Ventures, to talk about what it really takes to prepare your business for a successful and profitable exit.
Rob brings a wealth of experience from his time at Ernst & Young, his years as a serial entrepreneur, and now as an M&A advisor helping business owners avoid the common pitfalls that tank deals or leave money on the table.
What I love about Rob's approach is how focused he is on intentionality. He doesn’t just help businesses get sold—he helps them get ready to be sold the right way, to the right buyer, for the best possible outcome.
We dig into so much during this conversation, from setting expectations with buyers, to keeping your top talent through a transition, to organizing your books and systems so you’re not scrambling at the last minute. Rob also shares why some companies get premium valuations while others struggle just to close a deal.
💡 Whether you're looking to sell in 12 months or just want to build long-term value, this episode is packed with actionable insights you won’t want to miss.
🎯 What You'll Learn:
- The main reason deals fall apart (and how to avoid it)
- Why early prep (like SOPs and clean financials) is key to a successful exit
- The role of culture, communication, and team retention in driving company value
- How to think like a buyer and present your business like a premium asset
- Why now is actually a great time to sell if you are ready
⏱️ Chapter Highlights:
00:00 – Intro & Rob’s path from CPA to entrepreneur to M&A advisor
06:18 – Why most deals fail: misalignment & poor preparation
14:11 – The power of intentional planning before you sell
23:35 – Communication during change: don’t lose your top people
29:06 – Preparing your business like a buyer is watching
41:34 – Final advice: act like you’re for sale every day
👤 About My Guest:
Rob Levin is Managing Partner at CISVentures, where he helps founder-led companies prepare for and execute successful exits. His firm provides pre-sale planning, deal structuring, and strategic advisory services to help owners maximize value and avoid costly mistakes.
🎁 Grab Rob’s free Pre-Sale Planning Guide at cisventures.net
👩💼 About Me:
I’m Karen Rands, and I help entrepreneurs and investors create wealth through innovation and capital formation. Through this show and my Compassionate Capitalist Movement, I share practical advice and real conversations to help you build, scale, and exit businesses the smart way.
📲Learn more at karenrands.co
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