Most successful tech entrepreneurs retire to philanthropy or golf. Adrian Di Marco chose a different path.
After stepping down as TechnologyOne's CEO in 2017, Di Marco could have called it a career. He'd built Australia's largest enterprise software company from scratch and earned his place in the country's technology hall of fame. Instead, he doubled down on early-stage investing.
“I've personally witnessed the cycle of growth and can see the immense possibilities.”
“TechnologyOne was one of the first tech companies to list on the ASX 25 years ago, and its returns have been exceptional. That's why I'm passionate about innovation – it's refreshing to explore opportunities beyond the public markets.”
Today, Di Marco has invested in over 30 early-stage tech companies across Australia and overseas, plus several venture capital funds including Skalata.
The fund plus direct strategy
Di Marco's venture capital approach mirrors how savvy investors think about any asset class: get broad exposure through funds, then make targeted bets where you have an edge.
“I invest through VC funds because they offer simplicity, ease, and diversification, exposing me to various sectors such as FinTech and AgTech where I have no expertise. They handle the heavy lifting, and I'm willing to pay the fees for that expertise.”
But the real opportunity comes through co-investment. His fund investments provide deal flow access, letting him make direct investments where his operational experience matters most.
“I also like to invest directly in SaaS businesses because that's where my knowledge lies. SaaS is a domain I understand well, having lived the journey myself with TechnologyOne. I know what it takes to succeed, including having the right structure and board.”
Through his Skalata investment, Di Marco has worked closely with portfolio company Restoplus, applying four decades of enterprise software experience to help the hospitality tech startup expand into new markets.
Why early stage makes sense
Di Marco's choice to focus on early-stage funds like Skalata reflects his understanding of where the greatest opportunity exists today. While TechnologyOne's public market success was exceptional, he recognises that today's investment landscape has shifted, with explosive growth now happening in private markets before companies reach the ASX.
"“I invested in Skalata because it's an early-stage investment opportunity with diversity. They get involved early on, ensuring the right structure and board are in place. By the time a company reaches Series A, a lot has already been done.”
Early-stage investing also aligns with Di Marco's philosophy on sustainable growth.
“We believe that sustainable growth is the key to success. It's important to raise capital and use it sensibly, focusing on sustained growth rather than aiming for explosive growth followed by a bust. It's a marathon, not a sprint.”
This mirrors Skalata's model of capital-efficient growth, where startups get the resources they need without pressure to scale prematurely.
The human element
What sets Di Marco apart is his hands-on approach to founder development. Having built TechnologyOne from zero employees to thousands, he understands the lonely reality of entrepreneurship.
“I enjoy working with passionate founders and recognise that their journey can be lonely with limited support from the board. Being a mentor and creating a mentor network for them is something I find fulfilling.”
His advice to founders is direct: "Have a strategy to go global, focus on one market, and go deep. Pick one thing and excel at it globally.”
Beyond strategy, Di Marco looks for character. "I always ask myself if they are coachable, good listeners, and possess honesty and integrity. These qualities can often be assessed in just a half-hour conversation.”
He particularly emphasises building what he calls an "accountability driven" culture from day one. "We believe accountability delivers operational excellence, and it's very hard retrofitting an accountability-driven culture when a company grows.”
Spotting the next wave
Di Marco's continued enthusiasm for Australian startups reflects what he sees as a structural shift still in its early innings.
“There's an abundance of opportunities as vertical AI revolutionises industries. We are just seeing the tip of the iceberg, and the opportunities for VC will only increase dramatically in the coming years.”
This conviction, backed by real money across 30+ investments, suggests Di Marco sees today's early-stage market as similar to where enterprise software was when he started TechnologyOne: a massive opportunity most people haven't recognised yet.
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Disclaimer
This article is for informational purposes only and does not constitute financial advice or an offer to invest. Investments in venture capital carry significant risks and are suitable only for sophisticated investors. For more information, please request our Information Memorandum. This offer is not available to retail investors.
