A D.C. Homecoming and Harnessing Tech for Good

Whether we acknowledge it or not, we are all shaped by our childhoods — in one way or another. Our lived experience profoundly influences our worldview, how we prefer to spend our time, who we spend our time with, and more.

DMV-raised, former CEO of Caribou, Kevin Bennett, has turned adversity into motivation, and never wasted an opportunity to allow his career to compound.

This is a window into his journey.

Kevin's Childhood: A Glimpse into Entrepreneurship

In the heart of Great Falls, VA, a young Kevin Bennett absorbed the world of entrepreneurship through his father's business endeavors. Those endeavors — from real estate development to talent representation to financial investments — gave Kevin an under-the-hood look at the inner workings of building a business. As a child, he remembers watching his dad study papers and run numbers at the dining room table, always working on the next deal. But when Kevin was just 14, his father passed away at 42 — an event that instilled in him the uncertainty of life. "I learned to always be intentional and do your best work, because you never know how much time you have."

Encouraged by his parents to pursue his passions with grit and purpose, Kevin was often reminded, "You are doing this for you, not us." This principle guided Kevin through school, his early professional career, and eventually into the D.C. tech world, where he sought to make a tangible impact.

Formative Years: Education, Public Service, and a Tech Awakening

Kevin went from Brown University to internships on Capitol Hill to a job as a speechwriter for Virginia Senator Mark Warner. He was then admitted to Georgetown Law School, where he went with the intent of becoming a non-practicing lawyer like his dad. "I basically just went to learn. I've always been curious, and this was a way for me to get smarter in areas I found interesting."

Following Georgetown Law, Kevin began working on the National Broadband Plan for the Obama Administration. The experience marked a turning point, deepening his appreciation for technology's potential to effect change. "I saw how tech + 'x' could change the world, and knew I needed to go deeper on the operations of business," he said. "So I went to business school to learn to take the engine apart and put it back together." Kevin enrolled at UVA's Darden School of Business, a period during which he interned at both Facebook and D.C.-based Opower.

Return to D.C.: Learning, Networking, and Founding HomeZen

"I always knew I wanted to come home." And following Kevin's homecoming, he held marketing roles at DC-based Personal, Opower, and LiveSafe — experiences that allowed him to build a deep startup network in the city. In particular, Kevin's relationship with Mike Spainhower, a talented engineer, compounded over time. The two had complementary skills, worked together for more than five years, and constantly talked about founding their own company. They just needed to find the right problem to solve. "I was never going to be a B2B SaaS entrepreneur; I loved the human impact of technology too much," Kevin recalled.

In 2015, Kevin and Mike settled on a simple idea: help homeowners make more money by allowing them to sell without an agent. Applying lessons from his time in public service (how to run the "enterprise" of Virginia from Mark Warner and how to harness technology to drive impact from the Obama Admin) and at startups (time management, metric tracking, direct communication), Kevin got to work with Mike on HomeZen. The duo raised some money and built a product that delivered for customers, but couldn't figure out efficient distribution. They quickly recognized that the company wouldn't hit venture scale, and sold in early 2018.

Not fulfilling his vision motivated Kevin even more. He was determined to find a livelihood that leveraged technology to improve lives. He believed, and still believes, that pain and failure could be a superpower if channeled purposefully. So he got back in the saddle for his next adventure.

Mission Alignment: Joining Caribou

Kevin's deep D.C. network allowed him to build a relationship with QED Investors, a local VC. The firm had incubated a business, then called MotoRefi, that helped individuals refinance their car loans. "I don't care about cars and never have," Kevin told me. "But I cared about helping people. And this had all the ingredients to be a mission-driven company."

Kevin saw the opportunity to help customers save an average of $100 per month on their car payments, which he felt could meaningfully improve the lives of countless Americans. That "why" hooked him. After a breakfast with QED's Managing Partner, Nigel Morris, the two agreed that Kevin would be the company's next CEO. He started in June 2018.

Caribou's Early Days: Recruiting Talent, Cultivating Culture, and Selling a Pivot

Again leveraging his relationships, Kevin tapped into the "family tree of D.C. startups," including Opower, and rapidly built a talent-rich team. He was already seeing his early network-building work pay dividends.

Kevin had witnessed what a high-performing startup culture could look like and began to plant the seeds at Caribou, where he operationalized the idea through initiatives like Hackathons. This approach helped Caribou not just in hiring but also in building camaraderie and creating a compelling environment for a highly mission-driven, motivated segment of the talent market. "They weren't coming for the office space, that's for sure. Our first conference room had a shower curtain as a door, and our second was a server room," Kevin wryly recalled. He emphasized that there is no "one size fits all" approach to startup culture, but spending time shoulder-to-shoulder never hurts. Following those first few hires, Caribou went on to raise a Seed round led by Accomplice Ventures.

Scaling Up, Hyper-Growth, and Never Wasting a Crisis

That Seed round, followed by a successful Series A fundraise, kicked off a period of rapid growth at Caribou. "The nice thing about consumer marketplace is that when you find equilibrium and understand what levers to pull, it can start going pretty fast." And it did. The company went from two to three regional lenders to a whole cadre across the country. A strategic partnership with CreditKarma helped build efficient demand acquisition, and direct mail campaigns started driving significant conversion. "We grew 30%, 40%, 50% month-over-month — it was crazy." Product-market fit happened fast, and the company's valuation grew accordingly.

Over the next three years, Caribou raised more than $180M from investors, including Quiet Capital, Goldman Sachs Asset Management, Link Ventures, Moderne Ventures, Motley Fool Ventures, TrueStage, and IA Capital, and officially became a unicorn in May 2022.

But the path was not perfectly linear, and COVID briefly tempered growth. However, the team quickly recognized the opportunity a low-interest rate environment offered. Psychologically, the uncertainty of the pandemic also influenced people to save money however they could. Accordingly, what was first a headwind became the wind in Caribou's sails.

Embracing D.C.'s Tech Scene

Kevin believes the ability to navigate nuanced and evolving policy issues is a unique advantage for startups. "Successfully maneuvering in a complex regulatory environment is a superpower," he noted, underscoring the D.C. ecosystem's potential to outcompete other regions in the arena.

Kevin also argues that D.C. has the diverse and skilled talent pool to support a strong startup community. "The best people here are as good as the best people anywhere," he asserted. He highlighted Rachel Holt, specifically, as a force multiplier at Uber who built some of the company's most sophisticated operations. "We have talent density; we just need to leverage it."

What's Next for Kevin

Kevin officially left his role as CEO of Caribou in September 2023. "My wife and I both decided to go off the grid as far as work was concerned to focus 100% of our energy on the baby we had coming." Now, six months later, Kevin and his wife are getting their parenting sea legs under them — and he may just be feeling the itch to set sail on another entrepreneurial adventure.

Kevin's Lessons Learned

• Negotiate Deals Fairly: Kevin's Dad taught him that "you can cut too good of a deal." To make the relationship sustainable, all parties need to benefit.
• Equity Generosity: Being greedy with equity is a mistake. Everyone at Caribou had equity, which helped foster a driven, united team.
• Understand Your Customer: You can never know your target audience or their motivations too well; empathy is key.
• Vision vs. Execution: While having a grand vision is crucial, more startups fail in the early stages ("mile 2") than in the later ones ("mile 26"). Know how to scale from initial idea to traction by listening to what the market tells you.
• Company Survival: As Sam Altman says, "Companies die from suicide, not homicide." Focus on culture and delivering value, not your competitors.

My Takeaways

• Never Waste a Crisis: Kevin never allowed adversity in his personal or professional life to remain a roadblock for long. He has an optimistic outlook and positive attitude that he uses as an advantage.
• Strategic Partnerships: One of the many lesson's that I've learned from my boss, Steve Case, is: "if you want to go fast, go alone, if you want to go far, go together." He never fails to remind us about the importance of strategic partnership, and aligning incentives. This can be especially useful as efficient acquisition channels. Caribou has been quite successful leveraging channel partnerships.
• Intrinsic Motivation: The best founders, employees, professionals are motivated by something that can never truly be accomplished. They have a fire that burns deep inside them that motivates them to get out of bed every morning.
• Learn Something From Everyone: Kevin's career has clearly compounded. While at Caribou, he used something he learned from every one of his jobs. Going deeper, I believe that you can learn something from everyone — and every interaction.