Less than two years after closing its first $630 million fund, internet and consumer technology investor Left Lane Capital has raised a much larger $1.4 billion vehicle.
These are impressive amounts for an emerging VC executive, especially a company run by four investors in their early thirties. But Left Lane managing partners Harley Miller, Dan Ahrens, Jason Fiedler and Vinny Pujji are far from new to venture capital. They spent much of their careers as investors with Powerhouse for venture capital and growth capital Insight partners.
“I’m a career VC. It’s the only profession I’ve ever known,” said Miller, who joined Insight Partners in 2010 after earning his undergraduate degree from the University of Pennsylvania’s Wharton School of Business. “I knew from a young age that I was addicted to this industry, and I knew that at some point I would start my own business.”
At Insight, Miller invested in a number of European consumer-facing companies, including DeliveryHero, HelloFresh, Trivago and N26. The founders of these companies became LPs and advisors to Left Lane.
Miller and Left Lane’s other partners aren’t the only investors to leave Insight Partners and start their own businesses. Scott Maxwell was a senior managing director at Insight before launching OpenView Venture Partners in 2006. Similarly, Ben Levin and George McCulloch worked at the New York-based fund before starting Level Equity in 2009.
Miller acknowledged that New York-based Left Lane is unique compared to other successful companies with roots in Insight Partners.
“I don’t think, historically before Left Lane, Insight has ever formally blessed a group’s departure, whether that be in the form of attribution of a track record, or [to] support [it] economically,” said Miller. Insight Partners is a Left Lane LP, Insider reported in 2019.
Left Lane’s focus on consumer technology is complementary to Insight’s core business of investing in enterprise software. “Why would they sponsor people to leave to do exactly what they do, only smaller and probably less well than Insight could ever do?” said Miller.
Despite the track record of Miller and other partners and the support of Insight Partner, raising the first fund from Left Lane was no small feat. “This is no exaggeration. We’ve had about 2,000 pitch meetings over the course of a year to get our first fund on its hard cap,” Miller said.
When Left Lane returned to the market with its second vehicle last year, existing and new limited partners, including an Ivy League endowment, were ready to write bigger checks. Investors were particularly impressed with the company’s investments in high-growth companies such as M1 Finance, an investment and advisory platform, and GoStudent, a Vienna-based online tutoring startup.
For its latest vehicle, Left Lane will continue to support businesses, primarily in the Series A and Series B phases, writing checks ranging from $5 million to $100 million.
The company’s 25 investment professionals seek deals in North America, Europe and Israel, including companies that aren’t actively raising money, Miller said.
One such company is iTrustCapital, a profitable bootstrapped platform that allows people to invest in cryptocurrencies from their 401(k) or individual retirement accounts. Left Lane led the Irvine, California-based startup’s $125 million Series A in January with a valuation of more than $1.3 billion.
When Left Lane approached iTrustCapital, the startup founders had never heard of them or Insight Partners, Miller said. He added: “It just shows you how vast and vast the world of entrepreneurship is if you look hard enough, and I think we’re proud of that.”
Featured image courtesy of Left Lane Capital (left to right: Harley Miller, Vinny Pujji, Dan Ahrens and Jason Fiedler)