The Long Game: How Squire Went from Side Project to $750M
Dave Salvant and Songe LaRon left law and finance, never learned to code, and built Squire to a $750M valuation.
Most tech-founder stories start with a technical co-founder and a clean idea. Squire started with two people who could not code, sneaking into empty Columbia classrooms on weekends to whiteboard their way toward something with real scale.
Dave Salvant was in finance at JPMorgan Chase and a year into business school. Songe LaRon was a corporate M&A associate at Skadden Arps with a Yale Law degree and a partner track ahead of him. They met socially in Harlem in the early 2010s and started spending weekends working through ideas until they landed on the barbershop, an industry they used every week and one technology had largely ignored.
What makes this an Owner Mode story is the two different ways they reasoned themselves out of stable, high-status careers. Songe described the decision as an asymmetry of risk reward.
The downside was a setback, not existential, since a Yale-trained lawyer can always find another firm seat. The upside, in his words, was essentially limitless. Dave’s lens was the golden handcuffs: the spiral where the paycheck grows, the lifestyle expands, and the cost of leaving climbs until it is impossible. He wanted out before that spiral closed.
The path from whiteboard to scale was anything but clean. Squire applied to Y Combinator three times before getting in. During the Series A, the company almost ran out of money, going to sixty meetings and walking away with a single term sheet. Dave’s framing on that stretch was simple: you only need one yes no matter how many no’s you get. The filter that kept them alive through more than a decade was putting the customer first.
By the end of 2019, Squire had closed a Series B with a secondary component. Three and a half years after launch, both co-founders were liquid millionaires, and the company reached a $750M valuation. Songe is CEO. Dave is President. They have been building together since 2015.
Three takeaways from the conversation
Songe priced the downside before he feared it
Songe’s read on leaving Skadden Arps was an asymmetry of risk reward. He capped the worst case, confirmed it was survivable since a Yale-trained lawyer can always find another firm seat, then weighed it against an upside that was essentially limitless. Once he ran the numbers honestly, the leap that looked reckless from the outside became the easy call.
Dave left before the golden handcuffs locked
Dave’s lens was the cost of staying. The longer you stay, he argues, the bigger the paycheck and the heavier the golden handcuffs, until leaving costs too much to ever do. He went all in before that spiral closed, on the logic that you cannot be halfway in it. Plan A, back against the wall, this has to work.
You only need one yes
Squire applied to Y Combinator three times and pulled one term sheet out of sixty Series A meetings while nearly running out of money. Dave’s framing is that the number of no’s is not the signal. You only need one yes, and the filter that told them whether to keep going was always whether customers kept coming back.
Watch the full conversation
About this guest
Dave Salvant is President and Co-Founder of Squire Technologies, the barbershop technology platform that reached a $750 million valuation. Before Squire he worked at JPMorgan Chase. He holds an MBA from the University of Wisconsin-Madison and a BS from SUNY Albany. Songe LaRon is CEO and Co-Founder of Squire, which he co-founded with Dave in 2015. He holds a UCLA undergraduate degree and a Yale Law degree, and practiced corporate law at Skadden Arps. Squire has raised over $200 million from investors including Tiger Global, ICONIQ Capital, Y Combinator, Stephen Curry, and Trevor Noah.
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