Joe Montana may never have expected to find a second career that felt as natural and invigorating as football, but venture capital surprised him. The pace, the pressure, the need to evaluate people were skills he had spent his entire life sharpening. So, when he stepped away from the NFL, Montana began exploring early-stage tech investing with the same discipline that led him to four Super Bowl victories. What he discovered wasn’t a hobby or a retirement diversion, it was a world where leadership, preparation, and instinct mattered just as much as they did on the field. And as in football, the team around him would prove just as important as the talent that suited up for the game.
Montana reconnected with Ron Conway, one of Silicon Valley’s most influential early-stage investors, not long after retiring. They had known each other for years as their kids attended school together, but never expected that they’d be working together. Joe was fascinated by the way Ron built SV Angel and how he worked side-by-side with family to identify and support ambitious founders. “Joe was watching what I was doing with my son,” Conway says, “and he said one day, I would love to do that too.” Rather than treat Montana as a curious celebrity, Conway invited him into the trenches.
Montana joined Conway at start-up demo days, sitting quietly on the sidelines, absorbing how founders pitched, how investors probed, and how decisions were made with imperfect information. “He started going to the Y Combinator demo days with us,” Conway recalls, “and absolutely loved it.” Watching Conway operate alongside his son sparked Montana’s desire to build something multigenerational and meaningful. Teamwork had always been at the center of his success, and if he was going to build a venture firm, he wanted to do it with the mindset and the people who would give it the best chance at long-term impact.
Paul Graham and Jessica Livingston, co-founders of Y Combinator, also stepped in to help. They introduced Montana to Michael Ma and Michael Miller, two founders with serious credentials: Ma had built TalkBin, acquired by Google; Miller founded Cloudant, later acquired by IBM. Both brought the technical insight and operating experience that Montana needed to round out the partnership.
Montana credits his time with the San Francisco 49ers and coach Bill Walsh for teaching him how to identify talent and build a high-performing organization. “One thing I learned early from Bill Walsh was how to assemble a good team. It’s about finding the right people who are the best at what they do.” In Ma, Miller, and eventually his son Nathaniel, who had developed his own track record inside tech companies, Montana found the mix of technical diversity and founder empathy he wanted. “All three had exits to major corporations and understood how to build and scale a business,” Montana says. “I don’t believe that there’s a better team in the seed stage or earlier venture community than what’s here at Liquid 2.”
Liquid 2 launched in 2015 and Conway watched the early progress with a sense of pride and familiarity. “They started their first fund, started small,” he says, “and now they’re as big as SV Angel. We now collaborate and invest a lot together.” What impressed Conway most, though, was that Montana insisted the firm not be defined by his athletic fame. “I did not want to be recognized as a sports fund,” Montana says. “It took us a little while to get past that, but I was determined not to have that label on the fund.”
Part of Liquid 2’s success stems from Montana’s ability to relate to founders in a way few investors can. He brings the perspective of someone who has navigated pressure, expectations, and setbacks on the biggest stages in the world. “I basically speak to the founders about the basics,” he says. “Walsh’s philosophy always was to look at your fundamentals and see if you’ve lost sight of what got you that early success.” Montana recognized early that great founders and great athletes share something essential. “There are definitely a lot of similarities between great founders and great players,” he says. “It all stems from what’s inside them and their drive to succeed.”
That sensibility has become a core part of Liquid 2’s investing approach. And Conway sees the same leadership qualities translating naturally. “Joe’s a champion,” Conway says. “He loves and respects founders. He wants to help them on their journey.”
Montana’s presence also boosts the firm’s ability to work alongside top-tier investors. “Because of his affable personality and his brand,” Conway adds, “he is able to get into really good syndicates and have lasting relationships.” Those relationships helped Liquid 2 become an early backer of GitLab, Rappi, Anduril, Pipe, and a portfolio of fast-growing companies.
As the firm matured, so did the partnership between Montana and his son. The dynamic mirrored what had inspired Montana years earlier when he watched Conway work with his own children. For Conway, that father–son collaboration is one of the most gratifying aspects of his work. “It’s the most exciting and rewarding thing a parent could ever do, and I’m proud that it happened with Joe and Nate as well,” he says. “It’s a beautiful thing that our kids are shepherding it.”
Montana agrees and remembers well the skepticism he once heard about family-run venture funds. “There was one person who said he would not invest in a family-operated fund,” Montana says. “And I ended up sending him an email that we now had 20+ unicorns in that first fund and either eight or nine of them belonged to Nathaniel!”
For Montana, Liquid 2 has become a new kind of arena where the stakes are high, the competition fierce, and the reward comes from building something that lasts. It’s also a place where his leadership philosophy, rooted in fundamentals, teamwork, and relentless drive, finds new expression. In the long run, his legacy may extend just as far off the field as it did on it.
Image courtesy of PR Newswire
Having made investments in over 800 companies, Liquid 2 continues to deploy capital across its various funds and back the next generation of founders. Montana spent his football career guiding teams through high-pressure moments now guides founders through theirs. What began as a post-NFL curiosity has matured into a long-term evolution built on preparation, humility, and service to others. Montana and his team are shaping a legacy that stretches beyond trophies and titles. In the end, his greatest victories may not be measured in championships, but in the companies he and his son help support and grow together.
