Building a company takes focus. Exiting one demands a different kind of discipline. The shift from founder to wealth steward is about building the structure to handle whatever comes next. Markets turn. Opportunities appear and sometimes, the five Ds (death, disability, divorce, dispute, and distress) force decisions on someone else’s timeline. The founders who stay ahead are the ones who plan for change long before it arrives.

The path to a successful exit looks different in 2025. In the age of AI, building a strong engineering team or a slick feature set isn’t always enough. Valuations are shaped by what surrounds your product, distribution, data, trust, and deals are structured with new metrics and risks in mind. These five shifts offer a real-time snapshot of how tech M&A is evolving and what builders and buyers alike will need to know to stay ahead.

Copperleaf’s path to a $1B exit wasn’t easy (or typical). Under Judi Hess, with support from early backers like Pender Ventures, the team turned tough markets, early setbacks, and complex customer challenges into a foundation for long-term growth. Their story offers practical, lived experiences and insights for founders on building a business that’s truly exit-ready. Here’s how they did it and what you can apply to your own journey.

Greg Malpass didn’t set out to sell. He set out to solve customer problems and that mindset turned a solo consultancy into one of the largest Salesforce partners in the world, 1,100 employees, 1,800+ clients, and multiple product spinouts, culminating in a 2022 acquisition by Salesforce and a $100M+ exit for Traction Guest. Greg’s story is a case study of how exits aren’t events; they’re the result of continuous strategic choices. From customer-led growth to reclaiming product IP during acquisition, Greg built a company that was both resilient and highly acquirable.

Most founders think about their exit as a final chapter, a moment of payoff, or transition. But what if it’s not a moment at all? At TechExit.io, Jack Newton shared how Clio redefined the concept of an exit by treating liquidity as a continuous strategy and not just a one-time event. What followed wasn’t just a record-breaking $1.2 billion CAD financing round but rather a masterclass in secondaries, partner selection, and long-range planning. If you’re building a SaaS company with ambitions beyond the next round, this is the blueprint.

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.

It’s not just about having a world-changing product or a compelling pitch. The most effective founders develop something deeper: the ability to endure setbacks, make tough people-based decisions, and continue inspiring others when things don’t go as planned. Whether you’re prepping for an acquisition or have just raised a round, your mindset and leadership approach can shape your company’s trajectory and its ultimate exit. Here’s what we learned from two founders who’ve lived the full cycle.

It’s not just about having strong financials or flashy growth metrics. The founders who land great outcomes know how to play the long game—building trust, staying top of mind, and aligning with a buyer’s bigger picture. They understand that timing, positioning, and preparation matter just as much as performance. Whether you’re actively exploring a sale or just starting to think about what an exit could look like, the steps you take now will shape the opportunities available to you later. These seasoned founders and acquirers have been through it—and they’re sharing exactly what you should focus on to make your company not just sellable, but sought-after.

There’s no shortage of hype around AI—but for founders and business leaders, the real challenge is cutting through the noise to find what actually works. How do you avoid falling behind—or investing blindly? At TechExit.io Vancouver 2025, Nathan Yeung, founder of Find Your Audience, shared a practical, strategy-first view of how AI is reshaping business growth. Drawing from his experience with companies like Constellation Software, Procom, and Robert Herjavec’s team, Nathan offered a clear framework for making AI a real driver of value—not just a buzzword.