If you’re building with a potential exit in mind, one of the smartest things you can do is flip your perspective. Think like a buyer. What signals value? What builds trust? What makes an acquisition not just possible, but compelling?
In this article, we explore the firsthand experiences of two founders; Jason Leeson of Squirrel Systems (Acquired by Valoris Group) and Kris Hartvigsen of Dooly (Acquired by Mediafly), who each took very different paths when it came to selling their companies. Jason led the exit of a decades-old legacy business, while Kris navigated the sale of a high-growth AI startup in an everchanging tech market.
While each story is different, the lessons are surprisingly aligned.
Key takeaways:
- Buyers are looking for long-term value and proof that it’s durable.
- Founders who get acquired build relationships early and show up with clarity, consistency, and intent.
- Alignment, trust, and transparent communication matter more than any single metric.
It’s not just about performance; it’s about preparation and founders who achieve strong exits don’t stumble into them; they shape them deliberately over time.
Put simply; great exits are rooted in trust, timing, and strategy. Whether you’re just starting to consider selling or already taking early steps, the decisions you make today directly impact the opportunities available tomorrow.
Here’s how two founders navigated the complexities of selling and what they believe every founder should be doing to set up a successful outcome.
1. Know Why You’re Selling & When To Start
Every smart exit begins with alignment. Why are you selling? What outcome are you aiming for and when?
Jason Leeson’s sale of Squirrel Systems was triggered by succession planning, he said “the principal at the family office that owned Squirrel was looking to retire… it was about repositioning the portfolio.”
For Kris Hartvigsen at Dooly, it was a perfect storm; “My co-founder needed to leave. My father passed away. AI was gaining steam, SaaS was tightening, and we had raised more cash than we could effectively deploy.”
In both cases, the founders had a clear understanding of why they were selling. That clarity shaped their approach and timeline. The takeaway: don’t wait for crisis or burnout, you need to start planning early, emotionally and strategically.
2. Prepare Like You’re Already In Due Diligence
Buyers won’t just look at your metrics, they’ll leave no stone unturned. From IP to employment contracts to data security, due diligence is both comprehensive and time-consuming.
At Dooly, recent fundraising meant some of the groundwork was done; “The data room was mostly there. But we still had to do a huge lift on finance, legal, and IP transfer. Especially with our cross-border structure.”
Meanwhile, for Squirrel, it was about cleaning up decades of operational history; “Squirrel’s been around 40 years. Cleaning up employment agreements, contracts (some going back decades) was a massive job.”
Despite their differences, the overarching theme is this; don’t wait until a buyer is at the door, get ahead of the process and clean up your legal stack. This means standardizing contracts and documenting your IP because a well-organized data room is a signal in itself, showing that you’re serious, prepared, and credible.
3. Manage The Stress, Silence, & Stakeholders
There’s no disputing that M&A is emotionally intense, with founders often juggling a full-time deal process while still running the company and keeping it all confidential.
Kris shared how “you’re playing this real cryptic role within your business. You feel kind of dishonest with your team because you can’t fully explain your absence.”
Jason added that “there’s a misconception that your advisor will run the process. That’s not true. If you want a successful deal, you have to be all-in and hands-on.”
Both emphasized the importance of support systems. Internally, you need leaders who can absorb operational responsibilities. Externally, you need advisors who can steer legal and financial pieces of the deal.
Then, when the time is right, honest communication with your team becomes critical to preserving trust.
4. Understand That Relationships Make (Or Break) The Deal
Ultimately, trust is what gets deals done. From the first conversation to the final signature, the strength of your relationships (internal and external) is what matters most.
Kris put it plainly; “Evidence that [a buyer] can actually close matters. Past performance really is key.”
Jason echoed the point, saying how “conversations earlier between management and shareholders would’ve helped. You need alignment on when to sell and why.”
And when markets tighten, relationships are stress-tested. As Kris said; “we were the bell of the ball for two years. But when things got tighter, the way people showed up changed. True colors come out.”
Both Jason and Kris epitomize how a great exit isn’t just luck, it’s something built on clarity, preparation, and trusted relationships that are formed long before you’re ready to sell.
If acquisition is part of your plan, don’t wait and hope. Start building a business someone wants to buy. That means starting early, knowing your why, cleaning up your house, building real trust and then when the right buyer shows up, you’ll be ready.
TechExit.io is the M&A ready event for tech entrepreneurs. Learn from the biggest acquisition success stories and connect with the players that made them happen at TechExit.io.