Finding the Perfect “Match”: How Business Acquisitions Are Just Like Kelce and Swift’s Engagement
When Travis Kelce recently proposed to Taylor Swift, the world went into a frenzy. But behind the glittering ring and the millions of Instagram posts, there’s a simple truth: they’re a fit. They complement each other, share values, and see a future together.
Selling your business isn’t all that different. After years—often decades—of building something you’re proud of, the question isn’t just who will pay the most for it. The real question is: who will remember the details “all too well” and carry those pieces of your business into the future?
The Coming Wave of Boomer Transitions
Here in Canada, we’re about to see one of the largest business handovers in history. Baby Boomers own the majority of small and medium-sized businesses, and thousands are preparing to retire in the next decade. Studies estimate that more than three-quarters of business owners expect to exit in the next 10 years, but most still don’t have a formal succession plan in place.
That means many business owners are facing the possibility of closing their doors—not because their business isn’t strong, but because the right buyer wasn’t found. That’s a tragedy not just for the owner, but for employees, customers, and communities who rely on these businesses every day.
Legacy Matters
For most owners, selling a business isn’t like selling a car. It’s a lifetime of early mornings, tough decisions, loyal customers, and maybe even kids who grew up helping out after school. There’s pride attached to it—and that pride deserves to live on.
That’s why legacy matters. The right buyer isn’t just someone with a chequebook—they’re someone who understands what you’ve built and wants to nurture it. Choosing the wrong buyer? Well, that’s when your hard work risks turning into a “Blank Space”—and not in the chart-topping kind of way.
Why Fit Between Buyer and Seller Is Critical
Think about Kelce and Swift: different worlds—football and pop superstardom—but they’ve found common ground. That’s exactly what makes a business handoff successful.
- Shared vision: A buyer who understands where the business has been and where it can go will build on your foundation instead of tearing it down.
- Respect for culture: Businesses develop personalities over time—how employees are treated, how customers are welcomed. Preserving that culture makes transitions smoother.
- Community ties: Just as Kelce shows up in the Swiftie universe, the right buyer shows up in your business’s community.
Of course, only time will tell if Kelce and Swift make it “forever and always.” But here’s the good news for business owners: you can structure your deal, put the right protections in place, and avoid your legacy going “down in flames.”
Employees: The Unsung Heroes
Employees are the backbone of any transition. They’ve helped carry the business to where it is today, and they’ll be the ones making sure it succeeds tomorrow. Yet too often, they’re left out of succession conversations until the last minute.
The right buyer recognizes the value of your people. They see employees not as overhead, but as experience and continuity. Keeping staff engaged and confident through the process means customers keep receiving the service they know and trust. Without that, even the smoothest sale can stumble.
A Seller’s Guide to Finding “The One”
Selling your business may not involve a stadium proposal and a pop superstar—but it does require some thoughtful matchmaking. Here are a few ways to improve the odds of finding the right fit:
- Start early. Planning five to ten years in advance gives you time to prepare your business and identify the right buyer.
- Look beyond the cheque. The highest offer isn’t always the best one. Consider how the buyer plans to treat your employees, customers, and legacy.
- Talk openly. Just like in a marriage, communication matters. Be candid with potential buyers about your goals and concerns.
- Include employees. Whether it’s through profit-sharing, ownership opportunities, or simply involving them in the transition, they need to know they’re part of the future.
- Seek advice. Advisors, brokers, and accountants can help separate emotion from strategy—and keep you from making hasty decisions.
Passing the Torch With Confidence
Travis Kelce and Taylor Swift didn’t just say “yes” because the timing felt right; they believed in what they could build together. The same goes for selling your business.
As the Boomer generation begins this unprecedented wave of transitions, the best outcomes will come from owners who treat succession as more than a transaction. It’s about finding the buyer who will honor your years of effort, value your employees, and carry your legacy forward.
Because in the end, it isn’t only about who buys your business. It’s about who says “yes” to carrying your life’s work into the future. And unlike celebrity marriages, you don’t have to wonder if it will last—you can plan it, protect it, and shake it off knowing your legacy is in safe hands.
How Alberta Business Sales Can Help
At Alberta Business Sales, we understand that selling your business is one of life’s biggest milestones. Our role is to guide you through the process, ensure your business is properly valued, and—most importantly—help you find the right buyer who fits your vision, respects your employees, and preserves your legacy.
Because while we can’t guarantee Travis and Taylor will make it to their silver anniversary, we can help you write a business “Love Story” with the right match—one that stands the test of time.
Heather Miller General Manager, Alberta Business Sales and Commercial Ventures