By Olivia DeWan 
Peter O’Callaghan is the Managing Director of Square Root, a B Corp-certified fund backing founders fixing industries from the inside, across food, technology and agritech. As former CFO of Strong Roots, he was part of the team that grew an Irish challenger into a brand acquired by McCain Foods in 2024.
What are your main priorities and goals in your role?
My role comes down to two things: finding founders worth backing, and helping them win once we’re in.
The part I find most energising is working alongside founders rather than watching from a board seat.
We make fewer bets than most funds and go deeper on each, supporting companies on strategy, supply chain, financing and market entry. The value we’re proudest of is the introduction that unlocks more for our founders.
What are your biggest challenges as Managing Director?
The most interesting challenge is saying ‘no’ well.
Strong founders find their way to people who have built and sold companies, so we see more good opportunities than we back.
The discipline is separating a great story from a great business, staying open to conviction while holding the commercial line.
When something is excellent but outside our expertise, the right move is to point the founder to a better-suited partner.
How do you keep your team motivated?
We’re a lean team by design, so this is really about keeping founders motivated through the full arc of building a company.
The harder moments are the difficult stretches, when we add the most through perspective, practical help and the right introduction.
Having been through the same lows ourselves, we earn their trust by being genuinely alongside them.
What are the challenges facing the industry going forward?
Technology and globalised supply chains have made it far easier to build a product and reach a market, producing a steady flow of challenger brands.
The harder reality is breaking through as shelf space and attention are finite, and most categories are still dominated by larger players.
The ones that succeed have real distribution, rate of sale and a reason to exist beyond the launch.
What new trends are emerging in your industry?
The obvious answer is AI, but not for the reason most give.
What matters isn’t the technology, it’s how far it’s cut the cost and time to build. What once took months now takes days.
For talented founders, that’s a gift as they can test, learn and reach customers faster than any generation before, and we’re seeing capable people across food, technology and other industries build credible businesses with lean teams.
Are there any major changes you would like to see in your sector?
Many modern businesses are capital-light and global from day one, and the current support framework wasn’t built for them.
From an Irish perspective, I’d like to see state support that’s easier to access.
The criteria often assume a traditional model, with fixed local headcount and a set export path, when our most ambitious founders are international from week one.
As an employer, are you finding any skill gaps in the market?
The most consistent gap is commercially experienced operators who can do both, build a brand and run the operational engine behind it.
Early-stage teams often have brilliant product vision but haven’t yet scaled internationally. Part of how we add value is closing that gap directly, pairing founders with operators from our network and stepping in alongside them.
How did your strategy develop in the context of the banking and economic crisis?
Square Root was established well after the crisis, but its lessons shape how we invest.
The operators we back came of age in an era of disciplined capital and sustainable growth over growth at all costs, building businesses that stand on their own fundamentals.
How do you define success, and what drives you to succeed?
Success means proving that strong financial returns and meaningful impact can coexist at scale, whether we’re backing a food business or a technology company.
The common thread isn’t sector, it’s founders for whom doing right and doing well aren’t a trade-off.
What’s the best advice you’ve been given in business?
One piece of advice has stayed with me: a gap in the market does not always mean a market in the gap.
We’ve reviewed products that solved a clear gap, but on closer look, the real size of the market didn’t support the projections.
What advice would you give to others starting in business?
Very few careers or businesses follow a straight line, so don’t be afraid to fail early and learn quickly.
The best founders treat setbacks as information, not verdicts. And while many look straight to the US, there are real, under-appreciated opportunities in Central and Eastern Europe.
What have been your highlights in business over the past year?
Two things stand out. Becoming a certified B Corp was a real milestone, validating our belief that investment can create value beyond financial return.
But the highlights I enjoy most are the founders’ wins, seeing portfolio companies reach their next stage of growth, because we’d been on the journey right there with them. LOVE CORN is a good example of this; we worked with them on their Series B fundraising process.
What’s next for your company?
We’re deploying larger pools of capital while keeping the disciplined philosophy and B Corp principles that got us here.
What’s exciting is the quality of founders coming across the table now, and several portfolio companies are gearing up for their next phase – be that new markets, new rounds, or new products.
Where do you want your brand to be this time next year?
A portfolio that visibly proves our point, that doing right and doing well aren’t a trade-off, more founders backed, and capital deployed into businesses solving meaningful problems.
What is the best book you’ve ever read (non-business) and why?
Most of my reading is business or sports biographies, drawn to how people perform under pressure, not far from backing founders.
In fiction, the one that stayed with me is A Gentleman in Moscow, which explores how relationships, curiosity and purpose can overcome obstacles.
What is your favourite hobby and why?
Golf, though my handicap suggests significant upside potential.
I enjoy that it’s completely absorbing, a few hours where the only problem to solve is the next shot, and it’s where a lot of good conversations happen.
What is your mantra for life?
I want to open more doors than I close, staying open to new experiences through new relationships, travel and food.
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