Left Lane’s first fund weighed in at $630 million. Today, the team is back with $1.4 billion to deploy into growth capital for consumer and internet tech companies across the globe from its offices in New York and London. I spoke with Harley Miller, CEO and managing partner of Left Lane, who closed the $1.4 billion on his 33rd birthday.
“I’m the oldest person on the investment team at the firm — by about a year — but I’ve been doing this for 13 years. It’s the only professional discipline I’ve ever known and I have been working at honing and perfecting that craft,” says Miller. “It’s sort of a rare vantage point because VC was not a traditional asset class or industry that lends itself to an institutionalized Analyst Program where people come right out of school. Typically, there was more of a circuitous path to get there in the past. Maybe you were a banker or consultant and you went to business school. Something that we take to heart is ‘how do you breed professional investors from the ground up and help shape them.’”
Left Lane has made 36 investments into internet and consumer technology companies spanning a dozen countries. The firm targets businesses at key growth inflection points, and leads deals at the Series A to C stage. The firm invests across fintech, edtech, SMB tech, software, food tech, e-commerce, health and wellness, gaming and entertainment, and beyond.
When challenged on the young team — most venture funds tend to be run by people with significant operational or financial experience — Miller pushes back enthusiastically.
“We have a high regard for the human condition — not being a flyover board member. It’s a privilege to be there, as opposed to a duty that where you show up once a quarter and you pontificate just to have your fucking voice be heard. It’s the classic archetype of word vomit,” Miller says, airing his frustrations. “[I’m frustrated with] the VC who doesn’t do jack in diligence, who outsources it to his or her mid-level junior people, and then shows up to the board meeting and for the first six months, asking elementary rudimentary questions. It’s like, ‘Hey, did you not do an iota of diligence? Like these are basic business model questions? Why?’”
Miller encourages founders to be cautious about who to choose as their investors.
“Notably over the last few years, there have been a lot of new tourists coming into the asset class of venture or growth equity. They are all ‘we’re super entrepreneur friendly, we don’t need to take board seats’,” Miller explains. “We don’t do that. It’s not a job for us. It’s a way of life. I think if you come at it with that intentionality, you’re by definition going to be doing better than the vast majority. Just showing up and caring ain’t enough. A lot of funds have this concept of former operators that turn VC, and I think it can be really powerful, but again, make no mistake, it takes years to hone your craft as an investor who has had the pattern recognition across hundreds of deals. You have to have a regard for the human condition. You have to be able to navigate and have a lot of surface area and range of different archetypes and personas of founders that you can work with, whether that’s someone of a different background, religion, creed, race, age, for that matter, geography.”
As the investment community became better and better at investing in SaaS companies, Left Lane decided to go after the spaces that were left behind, in particular internet-enabled consumer tech with recurring business models.
“Amidst a world of generalists mimicking enterprise software, SaaS investors, we saw that whitespace. We are so blessed to have 60 or 70 high-profile CEOs or C-suite operators of internet and consumer technology companies as LPs and advisors,” Miller says, explaining why a lack of operational experience in the firm’s investment ranks isn’t as big of an issue as I was trying to make of it. “We really bring that work to bear on behalf of our existing and future portfolio.”
The company invests in the Series A-C range, and it likes to lead the rounds it is involved in. The team suggests that the sweet spot for its investments ranges from $5 million on the lower end of the scale, up to $75 million checks for the higher end.
