24: Think You’re Exit Ready? Neil Schaffer’s 1,000-Day Rule Will Change Your Mind

Written By Bruce Eckfeldt
Neil Schaffer

Neil Schaffer, CEO of Carlton Advisors

In this episode of From Angel to Exit, host Bruce Eckfeldt sits down with Neil Schaffer, CEO of Carlton Advisors, to unpack the real-life complexities behind mergers, acquisitions, and exits for founder-led businesses. Neil brings decades of experience—from starting at Pricewaterhouse to leading a paper distribution company through 5x growth, to a game-changing food company acquisition that scaled from $7 million to $50 million and paved the way for a $2 billion valuation. Neil has co-founded, scaled and sold several successful businesses across five business sectors including financial services, big data, ad-tech, and enterprise software.

Neil explains how strategic, not just financial, intent should drive M&A decisions. He emphasizes the importance of storytelling when raising capital, the power of timing exit decisions around business cycles, and why founders must emotionally and operationally detach before they sell.

A core theme? Preparation. Neil outlines a “1,000-day rule” for exit readiness and offers a checklist covering leadership succession, financial visibility, playbook documentation, and strategic market awareness. He also shares how to spot the right buyer, why deal terms matter more than price, and the traps founders fall into when approached with unsolicited offers.

Whether you’re scaling to sell, considering a roll-up strategy, or deciding if you're truly ready to exit, this episode provides actionable insights grounded in real transactions. Neil’s strategic mindset and hard-earned wisdom are invaluable for founder-CEOs aiming to maximize value and navigate successful exits.

Key Takeaways

  • Exits require emotional readiness—ask what you want from the transaction.

  • Strategic buyers often pay more than financial buyers—understand their value drivers.

  • The 1,000-day exit plan ensures time for operational and financial preparation.

  • Valuation ≠ buyability—culture and competitive advantage often seal the deal.

  • Raising capital? Your story, not just your spreadsheet, sells the investment.

  • Equity vs. debt: Choose based on market conditions, cash flow, and growth stage.

  • Founders must systematize knowledge—buyers don’t pay for what's only in your head.
    Treat exit strategy as a quarterly strategic planning item, not a one-time event.

Contact Information:

Bruce Eckfeldt
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23: How Robert Heil Doubled Growth by Rebuilding Strategy Around Client Value Creation