Siding with Success
Jamie Elliott, founder at Upside Ventures, on blending capital, content and community
Jamie Elliott, founder at Upside Ventures, has always followed a unique path. He started his first company while at university, giving him his first real taste of entrepreneurship. Since then, it’s been a circuitous but advantageous path, and one that is currently taking a very interesting turn.
“I’ve known from early on that I needed to do something different,” he says. “When I set out to create Upside in 2023, I saw the macro situation. The market was going one way, and I’ve always been quite contrarian. I figured this was my opportunity to create far more value than I ever could have done back in 2021 or 2020. Right now we have a clean slate to do good deals, create value for our peers, and in turn generate strong returns, creating a self-perpetuating cycle where we can launch more funds and scale up on the basis of solid results, rather than simply market momentum.”
He’s the first to say that he has the good fortune to be working with some of the best partners a solo GP could ask for, including a co-founder of Arcade Media, who runs the platform end of the business. Then there’s the high-profile partnership that sets Upside apart: the Sidemen, the seven-strong British group that publishes viral content including sketches, travel challenges and video game commentaries on a YouTube channel with more than 20m followers. Their business interests include the Sidemen clothing brand, drinks, and restaurants, and they have now moved to Netflix with their latest show, widening their global audience even further.
“The Sidemen wanted to do more investments,” says Jamie who was introduced to them via his network. “They were moving away from traditional brand deals on their YouTube channels and social media, and instead wanted to invest in companies where they could leverage their platforms to drive growth. They wanted to keep more of the upside for themselves—hence the name of the firm.”
But executing that strategy required more structure. “They had built companies, made some great investments, but there’s a difference between doing a bit here and there versus creating long-term systematic value. We looked at models such as Knight Ventures, Mantis, Wheelhouse, even Kim Kardashian’s Skky Partners. The advantage of not being first is you can take the best parts of what others have done.”
The result is a hybrid model that combines venture capital with media influence, setting a precedent for the next generation of investor-operators. “Just having access to the Sidemen network, their media platforms, their channels—it’s phenomenal. It opens doors that would usually take years of strong returns to unlock,” he says.
Upside and Sturgeon Ventures
The US venture ecosystem is known for its dynamism, but Europe presents different challenges. Upside VC Limited is an Appointed Representative Firm of Sturgeon Ventures LLP which advises the self-managed board of the fund Upside Ventures Fund LP in Guernsey.
“For an emerging manager, it’s easy to get started in the US, but not so much in Europe,” Jamie says. “The UK is somewhere in the middle, but still closer to Europe in terms of regulatory hurdles, so working with Seonaid and Sturgeon is an absolute treat. It is extremely valuable knowing we have that safety net, not only of people but experience, where they can give you a gut feel or a take on something, and you can trust that it’s actually better than 10,000 previous decisions.”
For Jamie, one of the most important things is to continue learning while building the fund, honing perspectives on what’s good and what’s not. “We’re going to be judged the end of the day by the success of our investment decisions,” he says. “Gut is going to give you the initial feel but, of course, every fund’s strategy is different and it evolves over time. You will meet different founders of different businesses and you’ll get insights into different spaces that you did not have when you started your strategy. You hone your gut by making decisions many thousands of times and that defines you. Seonaid and her team have had those many years of decision making, and that’s a gut sense that I trust.
“Since we started working with Sturgeon, I’ve always had a lot of comfort that we’re covered. As long as I continue communicating with Sturgeon, they will make sure that I’m not taking any missteps – which means I can focus on core issues of fundraising, deploying, and backing the best founders to focus on getting this business off the ground.”
When he’s not working 24/7 Jamie stays active with The Ireland Funds. “Coming from a country that was a developing economy until the late ‘90s, it’s incredible how far we’ve come,” he says. “Using that advantage to benefit others is something I’d be remiss not to do.”
