The Ledger
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Left Lane Capital faced widespread LP rejections at its 2019 launch
“We did not, contrary to popular belief, we did not walk in and sort of get resounding yeses across the board from the world's foremost institutions. In fact, we got a lot of no's. Right. And a lot of rejection. And that was summer of 2019 that we left to start…”
LPs value process adherence as much as investment returns
“Doing what you said you would do, that process and adherence thereof, can be measured in the here and now, and I think that is as, if not more important, right, for allocators”
Deal picking cannot be taught and relies on innate pattern recognition
“You can't teach picking. I think that's something that's innate and comes with pattern recognition.”
Harley Miller fought to invest in HelloFresh when meal kits were dismissed
“I remember pounding my fist to invest in HelloFresh and still not too shabby at a ten billion dollar market cap, right? It was a lot more six months ago, but nonetheless, it's company and it was space that was still nascent.”
Left Lane Capital aims for 4x to 5x net MOIC across funds
“Ownership stake relative to cost base is what ultimately drives and governs a portfolio construction. Otherwise, you have to create two hundred billion dollars of enterprise value aggregate across your portfolio of what you would have as de minimis ownership s…”
Product-market fit is readable earlier in consumer startups than enterprise software
“All the hallmarks of product market fit can actually be ascertained and deduced at a much earlier point in that company's evolution as compared to a infrastructure software enterprise security company that it's at a Million of ARR with half a dozen or a dozen …”
Evaluating consumer startups purely through spreadsheets is definitionally impossible
“There's so much more variability, and I think it can never be plugged into a spreadsheet with like a thumbs up or thumbs out. That just will be definitionally impossible in consumer”
Other VC funds have reused Left Lane's diligence work dozens of times
“We've had our work come back to us with other funds Dozens of times”
Left Lane Capital held 2,500 LP pitch meetings for $630M Fund I
“We earnestly did about 2500 pitch meetings for our first fund, which To get to that fully subscribed fund of six hundred thirty million over the course of a year.”
Every Left Lane investment team member is trained in SQL and Alteryx
“Every single person that works with us at Left Land on the investment team is trained on how to use SQL, how to use Alteryx.”
Many Left Lane investments are bootstrapped, profitable, and do not need capital
“A lot of the deals that we do are proprietary or bootstrap. They don't need money. They're profitable.”
Harley Miller decides whether to back a founder within ten minutes
“In general, I feel like I know within five or 10 minutes of meeting an entrepreneur, whether I would work with him or her.”
Left Lane Capital mandates bottom-up deal generation by junior team members
“It's a prerequisite that we have junior people who push up the curve. It's a bottoms up lead motion.”
Left Lane will not increase check sizes despite raising $1.4B Fund II
“It's not like we're going to all of a sudden start doing investments that are double or triple the size, right? We want to keep doing more of the same.”
Left Lane raised $630M for Fund I and $1.4B for Fund II
“So when I talk about the fund size, our first fund of six hundred thirty million, our second fund at 1.4 billion, it's more than double the size.”
Left Lane Capital targets 15% to 20% initial ownership in deals
“We want to achieve 15 to 20% ownership out of the gate and keep position building from there.”
Insight Partners pioneered institutional analyst programs in venture capital
“And there was this firm Insight Partners who was, I'd say, arguably the group that pioneered this concept of kind of an institutionalized analyst program.”
Left Lane canceled vacations to close proprietary Masterworks deal in ten days
“Masterworks, that deal was proprietary. He wasn't out in market in earnest. This was last summer, July or thereabout of, you have, we dropped everything. We canceled our vacations in sort of early August to drive at this deal before it got out to market. That …”
Left Lane Capital speaks with approximately 1,000 companies per month
“We probably speak with a thousand companies per month, right?”
Left Lane conducts custom consumer demographic and behavioral diligence surveys
“We're running pretty rigorous, robust surveys, tying back self-inputed consumer demographic data with their behavior economically, their self-reported behavior. We're trying to really drive these Third and fourth derivative insights based on above and beyond w…”