How to Prepare an Exit Strategy

In an era of constant corporate reinvention, leadership changes are inevitable. When a new CEO takes the helm, you face a critical decision: position yourself as a valuable asset or prepare for a strategic exit. As someone who's navigated both scenarios, here are actionable insights for senior leaders at this crossroads. 🏆 Making Yourself Indispensable to a New CEO 🏆 Be the solution provider, not the problem highlighter. New CEOs are bombarded with challenges. Stand out by bringing well-thought-out solutions with clear ROI and implementation plans rather than just identifying issues. Master the art of executive communication. Adapt quickly to their preferred style—whether they're data-driven, story-focused, or bottom-line oriented. Deliver high-impact, concise updates that respect their time while demonstrating your strategic thinking. Align visibly with their strategic priorities. Study their public statements, early communications, and board presentations. Then demonstrate how your initiatives directly support their vision, using their language and metrics. Build relationships beyond formal meetings. Find authentic ways to connect—whether through shared professional interests or by volunteering for cross-functional initiatives they care about. These informal interactions often shape perception more than official reviews. Own a critical business problem. Identify a significant challenge facing the organization that aligns with your expertise, then create visible momentum in solving it. New CEOs remember those who help them achieve early wins. 💫 Preparing for a Strategic Exit 💫 Strengthen your external network now. Reconnect with former colleagues, actively participate in industry groups, and establish yourself as a thought leader. The strongest transitions happen through warm connections, not cold applications. Document your accomplishments meticulously. Capture quantifiable wins, leadership moments, and innovations you've driven. Update your resume and LinkedIn profile with these specifics before any transition conversations begin. Complete high-visibility projects. Accelerate initiatives that will demonstrate your capabilities and leave a positive legacy. These become powerful talking points in future interviews and strengthen your negotiating position. Secure transferable references. Build relationships with respected board members, key customers, or industry partners who can speak to your value independent of the current CEO. Their endorsements carry substantial weight. Cultivate financial readiness. Review your compensation structure, understand your equity position, and clarify severance terms. Consider consulting an employment attorney to optimize your exit package before negotiations begin. Leadership transitions are career-defining moments that test our strategic agility. Whether you choose to build influence with a new CEO or orchestrate your next move, intentional preparation makes all the difference.

In M&A, most sellers assume diligence begins 𝙖𝙛𝙩𝙚𝙧 the LOI is signed… But by that point, the clock is already ticking, exclusivity is locked in, and any surprises (real or perceived) can become deal-breakers or issues that chip away at price. The truth is, buyers walk in with a very specific checklist. They’re not just verifying financials, they’re looking for risks, for inconsistencies, and sometimes, for anything that gives them leverage, or even a reason to walk away. Here’s the good news: if you’re the seller, you can beat them to it. It starts with understanding what buyers are looking for: 🔎 HR and compliance gaps 🔎 Messy or incomplete contracts 🔎 Unclear financial adjustments or owner add-backs 🔎 Potential unresolved tax liabilities 🔎 Customer concentration risk 🔎 Unresolved litigation or contingent liabilities 🔎 Cap table confusion or unresolved equity promises These aren’t just technical details, they’re signals to the buyer, and in an M&A process, well-prepared diligence wins deals. What can sellers do? ✅ Assemble your own diligence checklist before buyers do. A good M&A advisor will help you do this during the preparation phase ✅ Have your financials reviewed or normalized by a third-party QofE provider ✅ Clean up contracts, org charts, cap tables, and compliance documentation ✅ Identify “gray area” risks early and prepare thoughtful explanations ✅ Think like a buyer, then remove any friction. Make it easy to buy your company. In diligence, the goal isn’t perfection, it’s being able to give the buyer confidence. When a buyer feels like you’ve done your homework, the dynamic shifts. You’re no longer defending surprises. You’re leading the deal with transparency and strengthening the value you’ve worked so hard to build. #mergersandacquisitions #Investmentbanking #MandA #exitplanning

You spent years preparing to sell your business. But how much time did you spend preparing for what comes after? I can’t tell you how many founders say the same thing after the wire hits: “I wish I had built a better team around me before I closed.” Because here’s what happens: You go from having purpose, momentum, identity— To waking up with a large bank balance… and no clear direction. That’s when the cracks show: – Missed tax windows – Conflicting advice – Blind trust in the wrong people – Or worse: paralysis The best exits aren’t just financial wins. They’re smooth transitions into what’s next. And that takes a personal post-exit team. ▸ Wealth Advisor (but not just any) You need someone who understands liquidity events—not just retirement plans. They should ask about your goals, investments, and legacy—not just pitch products. ▸ Tax Strategist (before and after the deal) They should already be at the table when the LOI is signed. Their job: structure the deal, minimize capital gains, and map out Year 1 planning. ▸ Attorney (who stays post-close) Post-exit legal work doesn’t stop. Earn-outs, trust structuring, estate plans—they need ongoing M&A fluency. Optional—but often game-changing: ◦ A performance coach or therapist – for the identity shift. ◦ A philanthropic advisor – if giving back matters. ◦ A family governance expert – if you’re planning wealth transfer. 🚩 Red flag: If an advisor pitches a product before understanding your goals—walk away. Trust is built before the money moves. You don’t assemble your dream team when you’re tired, emotional, and post-close. You build it when you’re clear-headed—before the deal is done. → Want to make sure you're preparing for all sides of your exit? The Sellability Checklist includes the key people, prep questions, and blind spots to cover in advance. (Link in first comment.) #ExitPlanning #Founders #WealthManagement #TaxPlanning #PostExit #SellSide #MergersAndAcquisitions #FounderLife #Entrepreneurship

𝐄𝐱𝐢𝐭 𝐒𝐭𝐫𝐚𝐭𝐞𝐠𝐲 𝐏𝐥𝐚𝐧𝐧𝐢𝐧𝐠: 𝐌𝐚𝐱𝐢𝐦𝐢𝐳𝐢𝐧𝐠 𝐘𝐨𝐮𝐫 𝐅𝐢𝐧𝐚𝐥 𝐌𝐨𝐯𝐞 Every founder exits. The only question is—on your terms or someone else’s? This guide dives into how to plan, structure, and optimize your company’s exit—whether you’re targeting acquisition, succession, or private equity. 𝐊𝐞𝐲 𝐓𝐚𝐤𝐞𝐚𝐰𝐚𝐲𝐬: 1️⃣ Begin with the End in Mind Start exit planning 3–5 years before the transaction. Timing drives valuation, taxes, and deal structure. 2️⃣ Know Your Exit Options From internal succession to third-party sale or ESOP—each path has tradeoffs in control, legacy, and liquidity. 3️⃣ Clean Up the House Buyers discount messy cap tables, weak governance, or personal expenses running through the business. 4️⃣ Get a Valuation Benchmark Early Don’t wait for an offer to learn what your company is worth. Use comps, EBITDA multiples, and market trends. 5️⃣ Assemble Your Exit Team You’ll need M&A advisors, tax strategists, and legal experts—long before LOI. 𝐁𝐨𝐭𝐭𝐨𝐦 𝐋𝐢𝐧𝐞: Exits don’t just happen—they’re engineered. Founders who plan early exit richer, cleaner, and with fewer regrets. PS. check out 🔔 for a winning pitch deck the template created by Silicon Valley legend, Peter Thiel https://lnkd.in/eQFrsUnE

He rejected an $8M acquisition offer. Made $1.4M profit the next year instead. I taught him to think like a holding company: "What would a holding company do with your business?" He'd been excited about a 4x multiple. $2M ARR, $8M offer. Finally, his exit after six years. We pulled up a spreadsheet. "Holding companies don't get emotional. They don't chase unicorns. Hold cos buy businesses and turn them into cash machines." "What do you mean?" "They'd cut 75% of your costs immediately. Install a lean operator. Extract maximum cash flow." His P&L: $2M revenue. $1.8M in expenses. $200K profit. "You're running this like a growth company. But what if you ran it like a holding company? Cut the team from 15 to 4. Eliminate the growth marketing spend. Simplify the roadmap to maintenance mode." "That would destroy my growth trajectory." "Would it? Or would it create a cash machine?" The new numbers: $2M revenue (customers weren't leaving). $600K in lean expenses. $1.4M annual profit. "You'd make more money keeping it than selling it." The honest math: $8M sale price versus $1.4M annual cash flow. His business would pay for itself in under six years. "But I want to start something new." "So start it. Use the cash flow to fund your next venture. Become your own holding company." I could see him processing the idea. Instead of selling to an acquirer, become the acquirer. "This was never going to be a unicorn," I told him. "So treat it like a holding company would. Cut costs, install systems, extract cash." He withdrew the acquisition offer the next day. Cut his team to 5 people. Simplified the product roadmap. Twelve months later: His company generated $1.2M in profit. Funded his new venture. The business he almost sold became his personal holding company. Most founders wait to get acquired, start acting like the acquirer instead. Sometimes the best exit strategy is not exiting at all.

7 steps every CEO must take before selling I’ve coached hundreds of CEOs through exits. The biggest mistake I see? Skipping the prep. Most CEOs jump straight to the offer. Before the business or the CEO is ready. Here’s the process I walk leaders through: 1️⃣ Gather business information If you can’t explain it, you can’t sell it. 2️⃣ Due diligence Clean up every corner. No surprises later. 3️⃣ Final valuation You can’t negotiate what you don’t understand. 4️⃣ Match with the right buyer Don’t chase the highest bid. Find the best fit. 5️⃣ Negotiate the terms This is where value is built or destroyed. 6️⃣ Sign the agreement The real risk is in what’s not written. 7️⃣ Plan the transition If it’s chaotic, the deal won’t last. This is where most leaders go wrong: They try to exit without structure. But if your business can’t run without you, you don’t have a business. You have a job. Build the system before you sell. Because your exit will expose your execution. If you can’t measure it, you can’t improve it. ♻️ Repost to help another CEO exit right. P.S. Which step would slow you down right now?