Courtesy of Gokul Rajaram, Ava Horton/BI
Gokul Rajaram’s approach as an angel investor starts with finding exceptional founding teams who can go the distance.
“At the earliest stages, it’s truly all about the founder,” he explained. “Great founders can take mediocre ideas and mediocre markets and either pivot or change the market and do the right thing to change the company trajectory.”
Rajaram said working in product at companies like Alphabet, Meta, and DoorDash during his formative years provided him with a deep bench of expertise and a powerful network that’s useful for startup founders in his portfolio.
“Whatever a founder’s situation, I can connect them to an expert that I’ve worked with at a great company who has solved that problem,” he said.
Rajaram has invested his own money in companies like Deel, BetterUp, Figma, Printify, Boon, and Atlas. After a successful track record as an angel investor, he will manage outside capital through Marathon Management Partners, “a venture capital firm that invests in founders who are obsessed with defining their categories.”
The firm’s name reflects the patience that Rajaram believes an early investor needs to have.
“Building a generational company is an exercise in grit, perseverance, and endurance, not dissimilar to running a marathon,” he wrote on X in March.
Rajaram has learned to value authenticity and depth of understanding. “You have to build something. You don’t just have to solve a problem — you’ll solve a problem better than anything else out there. You’ve got to truly spend the time to understand why,” he said.
Rather than getting wowed by shiny résumés or tenure at big-name companies, Rajaram looks deeper.
“I pay very little attention to where the founder has worked,” he said. “I don’t think there’s any correlation between being a star at a medium-sized or large company and being a seed-stage founder because it’s such a different dynamic.”
Looking for a ‘complete founding team’
While plenty of investors mythologize a single founder like Mark Zuckerberg or Elon Musk, Rajaram looks more for a “complete founding team.”
That means a builder and a seller, a balance of product execution and go-to-market savvy.
“There are a lot of builders who don’t know how to go to market, don’t have the commercial instinct,” he said. “The idea is you have both the commercial and the builder side represented on the founding team.”
He also looks for “first-principles thinking,” the ability of a founder to reason through a problem from the ground up, rather than following conventional wisdom.
That approach led him to write one of the first checks to Printify founder James Berdigans in 2016. The company merged with its competitor, Printful, last year.
“Everyone passed on James in the pre-seed, but I was excited by the founder’s depth of understanding and how much he knew about the failures of past attempts,” Rajaram recalled.
Rajaram is generous with his advice. On his website, he writes blog posts on product development, company culture, and strategy, among other topics.
As seed investing became more competitive over the past few years, Rajaram has tried to remain disciplined and avoid a sense of FOMO.
“Rounds were moving really fast, happening without any diligence,” he said. “You’ve got to be very thoughtful. I might miss a few great companies, but I also think a lot will flame out.”
Rajaram has learned from experience that angel investing requires a great deal of fortitude because you’re investing money in ideas with a high failure rate. Even the few who succeed against all odds can take over a decade to pay off.
“If you focus too much on the financial returns, you’ll be disappointed,” he said. “You’re truly planting a seed.”
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