Every entrepreneur dreams of building a business that lasts forever. But what happens when the smartest move is to sell? Brian Kelly, founder of The Points Guy (TPG), talked about that exact dilemma in an appearance on Founder’s Story with Daniel Robbins. In just a few short years, he turned a passion for credit card points into a multi-million-dollar business. Yet, at the height of its success, he made the surprising decision to sell.
Why would he walk away from a thriving company that was generating $400,000 a month? More importantly, what can other entrepreneurs learn from his strategic exit? Let’s dive into the key factors behind Kelly’s decision and the lessons founders can apply when considering their own exit strategies.
1. From Side Hustle to Travel Empire
Before The Points Guy became a household name, it was just a side hustle. Kelly started in the 1990s, helping his dad book flights using travel points. His expertise grew, and by 2010, he turned his passion into a small business—offering personalized help to people who didn’t know how to use their travel rewards effectively.
A friend encouraged him to start a blog, and The Points Guy was born. He committed to writing one blog post a day, every day, at the same time—a discipline that quickly grew his audience. Within six months, his blog traffic exploded, and within two years, he was making serious money through affiliate marketing—earning commissions from credit card companies when readers signed up through his site.
It wasn’t long before The Points Guy became the leading authority in travel rewards, raking in millions annually.
2. The Boom and the Bubble: Why Kelly Sold Early
Kelly was riding high, but he saw warning signs that made him rethink his future.
✅ Flood of Competition – Once people realized how much money he was making, hundreds of similar blogs emerged. Many of them cut corners, giving questionable advice and pushing credit card churn strategies that risked alienating the banks.
✅ Affiliate Market Instability – Credit card companies were starting to take note of the aggressive affiliate marketing landscape. Kelly, coming from the corporate world, saw the writing on the wall: the golden era of easy credit card affiliate commissions wouldn’t last forever.
✅ Advice from Mentors – Seasoned entrepreneurs around him said: “Take the deal. Take it yesterday.” Selling when the business was at its peak was far wiser than waiting for unpredictable shifts in the industry.
Faced with these realities, Kelly made a bold decision—he sold The Points Guy to Bankrate, a publicly traded company.
3. Negotiating the Right Exit (And Keeping Control)
Many founders fear selling their business means losing control. But Kelly negotiated strategically to ensure a smooth transition. Here’s how he did it:
📌 He structured a three-and-a-half-year earnout. Rather than receiving all the money upfront, he stayed on board to guide the company, ensuring a steady payout and continued growth.
📌 He retained autonomy. Bankrate allowed him to keep running The Points Guy with creative freedom, ensuring the brand’s vision remained intact.
📌 He protected his employees. He made sure the acquisition terms allowed him to continue hiring top talent and keeping incentives strong.
By setting clear expectations, Kelly sold the company without sacrificing its future.
4. The Truth About Staying On After an Exit
For many founders, post-sale life can be frustrating. Some regret staying on after an acquisition, feeling handcuffed by corporate red tape. But Kelly had a different experience.
🔹 “You have to trust the people you’re selling to. A contract won’t cover everything.” He ensured he was partnering with a company that aligned with his vision.
🔹 Later, Bankrate was acquired by Red Ventures, giving The Points Guy even more resources and marketing firepower. Instead of feeling stuck, Kelly found himself leading a brand that continued to thrive under new ownership.
His ability to adapt and evolve within the company post-sale kept The Points Guy growing, even after multiple ownership changes.
5. Kelly’s Advice for Founders Considering an Exit
If you’re thinking about selling your business, Kelly’s experience offers key lessons:
✅ Sell when things are great, not when they start declining. Waiting too long could mean a lower valuation or tougher negotiations.
✅ Think beyond the paycheck—negotiate for your team and long-term vision. The right deal isn’t just about money; it’s about continuity and growth.
✅ Only sell to people you trust. No contract can account for everything—trust matters more than paperwork.
✅ Expect industry shifts. If your business is booming, competitors and market changes are inevitable. Get ahead of the curve.
✅ This won’t be your last success. Kelly admitted that at first, he thought The Points Guy was a one-time stroke of luck. But his dad reminded him: “This will just be your first deal.” Selling doesn’t mean the end of your entrepreneurial journey—it’s often just the beginning.
Conclusion: The Smart Founder’s Exit Strategy
Selling a thriving business isn’t easy. But as Brian Kelly’s story shows, timing and strategy matter more than emotion. By selling at the high point, protecting his employees, and ensuring a smooth transition, he didn’t just secure a major financial win—he set up The Points Guy for continued success.
For founders, the takeaway is clear: The best time to sell is before you think you need to.
