Welcome back to another edition of The Wise Exit newsletter. This week, we’re covering:
Why what you do before going to market matters more than the process itself
The 5 pre-sale considerations every founder needs to work through
3 things you can do this week to start getting your business ready for a sale
Let’s get to it.
This Week’s Podcast
This Founder Sold 5 Companies in EdTech, SaaS, and eCommerce
Tommaso Trionfi is a serial SaaS founder and operator who has sold five companies across EdTech, marketplace infrastructure, and ecommerce. He co-founded and ran Wimba, the leading virtual classroom platform that grew to 180 employees and over $20M in ARR before Blackboard acquired it in 2010. He then led Merchantry through an all-stock sale to Tradeshift for $30M, and as CEO of Oak Hill Capital portfolio company Monsoon, he divested Alibris, Monsoon Commerce, and Stone Edge over an 18-month stretch.
Today, he’s the co-founder of Noro, an immersive video conferencing portal that bets on local hardware intelligence in an AI-driven future, and works with founders through the Exitwise Exited Founder Marketplace.
In this episode, Tommaso walks through each of his deals, what he’d do differently, and the lessons learned along the way.
If you're a founder thinking about a future sale, weighing cash versus stock, or trying to understand how to read M&A timing, Tommaso has been on both sides of the table and shares what actually matters.
Check out the episode above!
💡 This Week’s Big Idea
5 Things Every Founder Needs to Do Before Selling Their Business
Most founders think the exit process begins only when they decide to sell. But it doesn’t. It happens long before you actually take your business to market.
By the time you're fielding offers, sitting across from buyers, and working through due diligence, a lot of the most important work should already be done.
The reality is, buyers are smart. They're going to look under the hood of your business. And what they find (or don't find) in those first few weeks of a sale process sets the tone for everything that follows. Price, terms, timeline, trust. All of it gets shaped by how prepared you are before you ever reach the negotiating table.
Here are the five things we work through with every founder before they even think about starting a sale process:
Know what your business is actually worth today
If you haven’t already, get a valuation based on your financials, market, and how a serious buyer would evaluate your business. This number matters for two reasons. First, it tells you whether you're actually ready to go to market or whether you need more time to build value. Second, it gives you a defensible anchor going into negotiations. Founders who skip this step almost always leave money on the table.
Get the right professionals around you early
One of the most consistent mistakes I see is founders waiting until they're deep in a process to bring in the right M&A team. But by then, they're already playing catch-up. Because these aren't people you call when things get complicated. They're people you want at the table before any problems arise. Yes, the right team will help you close the deal. But more importantly, they’ll help you structure it in a way that actually maximizes what you walk away with.
Get your financial records in order
If a serious buyer showed up tomorrow and asked for three to five years of clean financials, could you produce them quickly and confidently? For a lot of founders, the honest answer is no. And that's a problem because messy or incomplete financials don't just slow down due diligence. They create doubt and give buyers ammunition to renegotiate. Start cleaning your financials up long before you need to.
Think carefully about timing
The timing around when you go to market matters. Things like market conditions, industry trends, tax environment, your own business trajectory, it all affects the offer you'll receive. If your business is growing, your sector is hot, and the conditions are favorable, that's a window worth paying attention to. While there’s no such thing as the “perfect” time, there are signals that can be a good indication of the right time for you.
Keep running your business like there's no sale happening
This one sounds obvious, but it's actually a lot harder than it sounds. A sale process is distracting. It takes time, energy, and focus, all things you were previously putting into your business. But the moment your performance dips mid-process, buyers notice. It raises questions, creates leverage on their side, and can unravel deals that should have closed. The best thing you can do for your negotiation is show up with momentum, not a business that's been on cruise control for six months while you waited to get to the finish line.
The bottom line is, the work that wins your exit doesn't happen at the negotiating table. It happens in the months and years leading up to it. Start earlier than you think you need to, get the right people around you, and treat exit preparation like the priority it is.
If you're thinking about an exit and want help working through any of these steps, reply to this email or reach out to us here. We're always happy to help you figure out where to start.
❓ 5 Key Questions to Ask Yourself This Week
1️⃣ Do I have a current, professional read on what my business is actually worth to a buyer today?
2️⃣ Have I identified the right M&A advisors, attorneys, and financial professionals for my industry, or am I planning to figure that out later?
3️⃣ If a buyer asked for five years of clean financials tomorrow, how quickly and confidently could I produce them?
4️⃣ Am I going to market at a time when my business story is at its strongest, or am I letting timing work against me?
5️⃣ Am I able to stay focused on running and growing my business while a sale process is happening in parallel?
📋 3 Action Items for This Week
☑️ Get a professional valuation or, at minimum, a directional read on your number: Don't go into this process guessing. Understand what your business is worth today, what's driving that number, and what factors would increase it. That conversation alone is worth having well before you're ready to sell.
☑️ Start organizing your financial records now: Pull your last three to five years of financials and honestly assess how clean and complete they are. If there are any gaps, inconsistencies, or personal expenses running through your business, start addressing them today, not six months from now when a buyer is asking questions.
☑️ Identify one advisor you should already have in your corner: Whether that's an M&A attorney, a transaction-experienced accountant, or an industry-specific advisor who's been through this process before (reach out to us if you want to connect with any of these), figure out who's missing from your team and start that conversation now.
That's all for this week.
Remember, the founders who walk away with the best exit outcomes didn’t get lucky. They walked into the process prepared and started earlier than they thought they needed to.
Whenever you're ready to talk through what exit prep looks like for your specific situation, reach out to us. We're always happy to help.
Talk next week,
Brian Dukes
Managing Partner at Exitwise
Whenever You're Ready, Here Are 3 Ways We Can Help You:
1. Get a free read on the value of your business
How do you determine what a business is worth? Take the guesswork out of your business's value with our free valuation calculator, based on 1000's of private sales and industry insights:
2. Add an Exited Founder to your M&A team
Search from 100+ Exited Founders on our marketplace and add one to your M&A team to enhance credibility, attract top strategic buyers, and leverage their personal relationships to maximize your exit.™
3. Need help preparing your business for a sale within the next 12-18 months?
If you’re preparing to sell your business within the next 12-18 months, we’ll help you build the right plan and connect you with the right buyers.

