How to Navigate Challenges After an Exit

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

”Life After the Deal  5 uncommon moves that made the transition work” What No One Tells You About Selling Your Business After 25 years building an engineering firm, the founder was ready to sell But not ready to let go. His identity was welded to the business. The spreadsheets said “retirement.” His gut said “panic.” Here’s what actually worked: Not just for maximizing the exit, But for surviving it with clarity and peace: 1️⃣ Reclaim Time Before You Exit → One full day each week spent away from work → Not hobbies. Experiments in identity The benefit: Create space to explore who you are without the business before the deal closes. 2️⃣ Build a Framework for What’s Next → Tested post-exit paths: mentoring, advising, teaching → Each got a trial phase before becoming a commitment The benefit: Confidence in your next chapter comes from experiments, not assumptions 3️⃣ Redesign Your Power Circles → Shifted key relationships from “boss” to “peer” → Built boundaries that preserved influence without control ➕ The benefit: Stay relevant and respected without needing a title 4️⃣ Create Freedom With Structure → Crafted a weekly schedule template, flexible but intentional → Anchored time to purpose, not tasks The benefit: Prevents post-exit drift and decision fatigue while still feeling free 5️⃣ Build Financial Clarity Before the Wire Transfer → Modeled life goals against the exit deal, down to the dollar → No vague budgets. Only tested projections  The benefit: Peace of mind to enjoy the exit without money anxiety The Result? When the deal closed, he didn’t crash. He transitioned with purpose, peace, and a plan. This is what real exit readiness looks like. Not just earnings and deal terms but identity work, tested systems, and a redesigned life.

The most confusing part of selling our company? Everything that came after. This is my most vivid memory of it: The acquirer wired us the money, we paid our banker, and our banker just... left. That was it. No manual or scheduled meetings for what came next. I remember sharing the news with my family, barely able to show them the number. Then sitting alone in my office, staring at my screen, wondering: what now? The questions started piling up: Do I need umbrella insurance? How much should I put in my kids' 529s? Should I superfund them? What does "superfund" even mean? Who handles my trust and estate planning? Do I need a trust now? These logistics were challenging, but they weren't the heart of the struggle. The deeper challenge was psychological: → shifting from a decade of sprinting to suddenly having a boss at Fortune 500 company → realizing my identity was wrapped up in being a founder → wrestling with the pressure to do something "important" with this opportunity while my peers were still building It was confusing. Here's what I learned, though: exits aren't endpoints. They're transitions that require an entirely new set of skills, mindsets, and support systems. My framework for navigating post-exit life: 1. Find peers who understand (but aren't trying to sell you something) 2. Set clear personal boundaries around spending and stick to them 3. Learn to measure success beyond your bank balance 4. Focus on time and impact rather than accumulation 5. Get comfortable being uncomfortable - you're learning an entirely new way of living The banks prepare you for the exit. Nobody prepares you for what comes after. That's one of the WHYs behind Long Angle, though: We wanted to start a community for people navigating wealth. It’s not JUST for founders, but it’s turned out to be an excellent landing pad for post-exit founders navigating this same transition (many of our members). Because sometimes the hardest part isn't getting there - it's figuring out what to do once you arrive.

Recently, I asked an entrepreneur who sold his business for $80 million: How did such a huge success feel like? His answer was eye-opening. The successful exit created a sense of invincibility, making them believe they had the midas touch to turn everything into gold. Became too adventurous, took on risky investments, and ended up losing millions. This is one BIG mistake founders make after their first exit: Thinking they are King Midas. They think they know-it-all. But here’s the reality check: 👉 Windfalls don’t make you bulletproof—discipline does. When founders focus solely on the exit, they often overlook what comes next. Plan ahead for life after the exit. Financial freedom is a gift—use it wisely. Focus on new goals: personal growth, impact-driven ventures, or prioritizing family. Those are your new KPIs. 👉 Burnout doesn’t disappear when the grind stops. You’ve worked tirelessly, hit that massive payday, and now you feel entitled to do it all. But jumping too quickly into new ventures can lead to burnout—one driven by over-commitment, aimlessness, or feeling the need to prove yourself again. The biggest takeaway? Remember, an exit isn’t the endgame—it’s a pivot point. Your opportunity to redefine success and start again. . . Interested in more productivity frameworks, insights about entrepreneurship, and success stories? Subscribe to my newsletter: https://t2m.io/OUvcJ5gL #entrepreneurship #venturecapital #startup #mergers #acquisitions Serial Entrepreneur & Investor Helping Startups Become Unstoppable – David Hauser

Being an exited founder is not always what it seems. Many of us who made it to exit worked ourselves to exhaustion. Left our families on a weekly basis for travel. Delayed having children...Spent holidays cranking out decks...were constantly ill with something that we ignored, arguing if we were not in the hospital it must not be so bad. Or maybe that was just me. After exit, during my "earnout period", I was numb. I had learned the hard way that no PE or acquiring firm cares about you or how hard you worked the day after you've signed over your company. Those on the outside assume you are set for life. Why are you complaining? Other founders ask you for investment and think you are being selfish when you probe into their companies, offering not investment but advice. Recruiters think you are probably not a team player and won't work as hard at something that is not your company. What's the term one used with me? "Founderitis." You don't really want to talk about it because you see your post-exit struggles as failure. And nobody wants to talk to a failure, let alone hire one. So you spend your post-exit life doing one of several things (I've witnessed among many of my ex-founder peers): 1. Launching new companies with abandon, hoping to redeem oneself but refusing to do it differently this time, burning through capital and relationships. 2. Stop taking chances entirely. Finding a job or gig with health insurance and reconstructing one's career history in ways that suggest that whole startup thing never happened. 3. Becoming obsessed with sustainable growth and work models and helping others avoid the pitfalls of startup founderdom. This is why I appreciated Bob Gilbreath's essays on life after exit. We met MANY years ago, when he was in what I now understand was a fairly grueling earnout period -- one he learned from. I put his latest piece in the comments. It's a reminder of a past I both celebrate and struggle with. I just wish we'd talked about this back when we worked together. #startups #founders #startupexits

If you think the hardest part of building a company is the hustle, you are in for a rude awakening. Because when you’re in it, you imagine the exit is the finish line. That once the wire hits, the pressure fades. That the finish line brings peace, clarity, and freedom. Let me tell you something no one else will: The real mess starts after the exit. I sold my company for 9-figures. And 24 hours later, I felt like a ghost in my own life. No more daily stand-ups. No more Slack pings. No one needed me. I was finally free. And I had no idea what to do with it. I had optimized every part of my identity around one thing: building. So when that chapter closed, I didn’t know who I was without the work. Here’s what no one talks about: → You don’t just lose the company. You lose the rhythm of your life. → Everyone around you wants to celebrate but you feel disconnected. → You have money but lose momentum. → You think you should feel gratitude. Instead, you feel guilt. → You want to rest but feel an urgent pressure to prove you can do it again. It’s a quiet identity crisis that hits harder than you expect. So if you’re on the road to an exit - or just dreaming about it - ask yourself this: Who will I be when I no longer have something to prove? Build the company, yes. Chase the outcome, if you must. But don’t lose yourself in the process. Because if you do… the check clears, the inbox slows, the noise fades… and what you’re left with is you. Make sure that person is someone you recognize.

A close friend exited his company and called me. I congratulated him on a successful exit and amazing value creation but he was depressed. We had a long chat after that. A common topic amongst our entrepreneur friends. “Life post exit”. One of the hardest adjustments that an entrepreneur has to make is their life post an exit. You know that you sold the company that you took years to build. It took loads of emotion, passion, hard work and sacrifice to build this. It was your love and life’s work. It takes a tremendous amount of mental adjustment to accept the fact that you crossed the line, it is no longer your company and life will be different (at least for sometime.) Some make that transition successfully. But most cannot because entrepreneurs fundamentally never work to just make money. They do it because of the passion and the sense of creative freedom they enjoyed in the process. It was the journey which was the reward. Post exit depression is a common thing for many. Reach out and talk to people. And your circle of close friends and advisors. And most importantly don’t be in a rush to find your new gig. Take your time. And doing nothing is also good sometimes. If you do this chances are you will end up doing the right thing for your next gig.

Building a company to a huge exit is fulfilling… But there’s a dark side most people don’t talk about: The exit blues. — You’ve been building a company for years, It was taking most of your: • Agenda • Schedule • Meetings Even your mind space. People were associating you with the company. Every time they saw you, they were asking about your company. Then over time, you begin to identify yourself with the company. You don’t realize it at the time, but this is a dangerous place to be. A similar thing happens with parenthood. For +20 years of your life you build your life around kids. You take them to school, the doctors, to sports events etc. They are in your house 24-7 and your life revolves around them. Then one day they leave to college. After you maybe see them once a year, twice a year. Now you have no kids, no agenda, almost no responsibilities. So now what? It's been +20 years that you built a life around that. Most of your identification was as a parent. OR perhaps in your case, as a business owner. We could call it “The Founder’s Empty Nest”. My advice to deal with this ‘emptiness’ or ‘exit blues’? There’s tons of support that you can get in order to guide you through this challenge and be able to enjoy what you’ve achieved, while designing this new phase of your life. Find purpose for the chapter after selling your company. Dedicate your time and energy on building something new you’re truly passionate about. Aim your focus on something centered around your values. This new hunt needs to be grounded in your core purpose. It’s the only way to fill the hole in your life and more importantly… Sustain it. — P.S. My passion is helping high performing founders and CEOs navigate crucial transitions with natural confidence and ease. DM me for more info.