The venture capital sector has traditionally displayed an uneven relationship with the American Midwest, stepping in enthusiastically during prosperous economic cycles only to recede rapidly toward coastal centers when times become challenging. For Columbus, Ohio-based Drive Capital, navigating this fluctuating tide of interest coincided directly with its own period of significant internal strife several years ago—a potentially disastrous split between the firm’s co-founders. Yet, instead of unraveling the firm, the departure may have actually enhanced its resilience and sharpened its focus.
Earlier this year in May, Drive made headlines in the venture community, distributing a remarkable $500 million to its investors within a single week. This extensive payout included nearly $140 million worth of shares from Root Insurance, following its successful exits from companies such as Austin-based Thoughtful Automation and another undisclosed investment.
The move, while eye-catching, wasn’t merely for show. Limited partner investors were understandably pleased, given the rarity of such rapid liquidity in current market conditions. Chris Olsen, the co-founder who now leads Drive Capital as its sole managing partner, characterized the event as highly unusual in today’s environment.
This outcome marks a dramatic resurgence for a firm that just three years earlier was confronting existential uncertainty as Olsen parted ways with fellow founder Mark Kvamme, both of whom previously held partner roles at Sequoia Capital. Their split, which caught the firm’s investors off-guard, ultimately resulted in Kvamme launching the Ohio Fund—an investment initiative that extends beyond traditional technology strategy toward regional economic development, inclusive of real estate, infrastructure, and manufacturing investments.
Olsen attributes Drive Capital’s current position largely to a contrarian approach, eschewing Silicon Valley’s fixation on enormous “unicorn” or “decacorn” valuations in favor of predictable, steady returns. He notes that billion-dollar outcomes are exceptionally uncommon, whereas more modest yet still substantial exits occur regularly—making Drive’s targeted returns both attainable and dependable. Olsen cites over a hundred IPOs and numerous mergers and acquisitions priced around the three-billion-dollar threshold as proof of a consistently fertile opportunity space.
The exit of Thoughtful Automation epitomizes this pragmatic strategy. The AI healthcare automation startup, while not a billion-dollar “home run,” still provided multiples above typical returns, largely thanks to Drive holding a significant 30% ownership stake—far higher than Silicon Valley’s more typical 10% average holding per investment. Olsen says roughly a fifth of their portfolio investments position Drive as the sole venture investor, reflecting the firm’s hands-on, value-driven approach.
Drive’s portfolio tells the story of wins and notable challenges alike. The investments in Duolingo and data platform Vast Data, now valued at around $18 billion and $9 billion respectively, have provided solid returns, along with the recent Root Insurance transaction. But the company also experienced setbacks—most notably, Olive AI, a Columbus-based healthcare automation company that raised over $900 million and was valued at $4 billion before eventually undergoing a piecemeal sell-off.
This mixed record underscores Olsen’s belief that a healthy venture strategy demands returns integrity even in difficult economic climates, rather than exclusively during market peaks. He also makes clear that Drive aims chiefly to identify promising ventures outside the hypercompetitive confines of Silicon Valley. Today, Drive occupies offices across six cities—Columbus, Austin, Boulder, Chicago, Atlanta, and Toronto—enabling it to partner closely with entrepreneurs who may otherwise feel pressured to choose between proximity to their investors or their customer base. For Olsen, this strategic positioning represents the key to the firm’s sustained growth.
Moreover, Drive actively invests in enterprises integrating technology into legacy industries commonly overlooked by coastal investors, including autonomous welding technology and advanced dental insurance solutions—sectors that nevertheless represent large segments of America’s expansive economy far beyond high-profile tech businesses.
Looking forward, Drive still has approximately 30% left to invest within its latest $1 billion fund announced when Kvamme was still on board in mid-2022. Olsen confirms the firm manages around $2.2 billion in total assets across all its funds, emphasizing that Drive has consistently achieved top-tier performance with their earliest funds returning a net multiple upwards of four times the invested capital.
Further validation of Drive’s longstanding belief in Columbus as an emerging technology hub arrived recently, with news that tech billionaires such as Palmer Luckey and Peter Thiel are establishing Erebor, a cryptocurrency-focused banking institution, in the city.
Reflecting on the evolution since founding Drive in 2012, Olsen remarked on the striking shift in perception. What was then considered a radical strategy—basing a prominent venture operation in Columbus—has now transitioned into a farsighted model that industry icons are actively embracing, highlighting a broader geographic shift underway within the American technology and innovation landscape.
