Start Building a Clear Exit Strategy

This week, we're covering:

• How to start building a clear exit strategy today

• 5 challenging questions that will pressure-test your exit readiness

• 3 actionable steps you can take this week to prepare for your business exit

Let’s dive in.

💡 One Big Idea

How to Start Building a Clear Exit Strategy Today

Most founders and business owners don’t realize they’re already in the middle of an exit, and they have been since day one.

Because contrary to what you might think, your exit doesn't begin the day you decide to sell.

Every decision you make right now is shaping what your future exit looks like — whether you're planning to exit in a matter of months or decades.

I hear far too many stories of founders just like this:

Founders who wait too long to plan, only to end up reacting to inbound offers with no leverage. Founders who assume their business is worth more than it is, without having clarity on the metrics that matter. Founders who could get a premium for their business, but only if they had spent the previous 12 months aligning strategy with outcomes.

At the end of the day, the first (and most overlooked) step in exit planning isn’t your P&L or your buyer list.

It’s getting brutally clear on what you actually want as a founder.

Everything else flows from there.

Your Action Items:

1. Define your “why” and “when” in writing: If you haven't already, clarify your exit timeline, ideal outcome, and personal financial and lifestyle goals. Ambiguity here kills momentum.

2. Align your stakeholders early: Loop in your co-founders, spouse, leadership team — anyone you trust who should know about your plans. Misalignment on timing, valuation, or intent is one of the biggest deal-killers, and it always shows up late if you don’t address it early on.

3. Create a 12-month “exit prep” plan (even if you’re not selling yet): Reverse-engineer from your ideal exit. What needs to be cleaned up? What metrics do you need to track? What story do you want to be able to tell? Write it out and revisit this quarterly.

If you need help with any of this, just reply to this email or contact us here to learn more. I'm happy to walk you through what the process looks like wherever you're at in your journey.

❓ 5 Key Questions to Ask Yourself Today

Before you even think about an exit or talk to a buyer, there are several important questions you should be asking yourself.

The five questions below are anything but easy to answer. In fact, they'll challenge you to think about things you may never have before. But they could be the difference between a clean and confident exit, or one you wish you could take back:

1. If your business sold 18 months from today, who benefits most from the outcome — you, your team, or your investors?

If the answer isn’t clear, how will you make decisions when those priorities inevitably compete with one another?

2. What’s the one outcome you don’t want from your exit, and are you actively designing your exit strategy around that risk?

A few examples of this might be regret, loss of identity, a toxic buyer, misaligned earnouts, etc. These matter more than founders often realize.

3. Who else needs to be emotionally or financially ready for your exit, and have you had those hard conversations yet?

Maybe it's your spouse. Maybe it's your co-founders, partners, or legacy employees. Remember, exit clarity isn’t just about you.

4. If a buyer offered you 80% of your “target number,” but it was a perfect fit on every other term, would you take the deal?

Your answer reveals whether your valuation is your true North Star or just a placeholder.

5. What personal chapter do you want to open after your exit, and are you building the space, skills, and relationships today to make that next chapter possible?

Selling a business without clarity on what’s next is the fastest path to post-exit regret.

📋 3 Action Items For You This Week

1. Block out 30 minutes and write down your exit non-negotiables:

List the 3 things that must be true for your exit to feel like a real success — whether that’s a certain valuation, team retention, buyer type, or personal freedom. Clarity here guides every decision that follows from here on out.

2. Set a personal financial baseline:

Meet with your wealth advisor or CPA and ask them how much you'd need from a sale to fund what’s next for you post-exit. Most founders never calculate this, which is exactly where regret starts to creep in.

3. Sketch your exit timeline:

Take out a piece of paper. Mark today’s date, a realistic exit window, and the milestones you’d need to hit to be ready. This turns a fuzzy goal into a clear plan.

That's all for this week.

Reply to this email if you have any questions or need help with any of the above. I'd be happy to walk you through it.

Until next time,

Brian