Why TechnologyOne founder Adrian Di Marco chose early-stage venture capital
Adrian Di Marco built TechnologyOne and now backs early-stage companies and venture funds. Why he splits his money between funds and direct deals, why he backs early stage, and what the 2027 CGT change adds for advisers.
TL;DR
- Who this is. Adrian Di Marco founded TechnologyOne, which listed on the ASX in 1999, and stepped down as its CEO in 2017.1
- He uses funds and direct deals for different jobs. Funds cover sectors he doesn't know; he invests directly in software, where he does.2
- He is happy to pay fees for expertise. In his words, the funds “handle the heavy lifting”.2
- He backs early stage because the groundwork happens there. Structure and board are set long before Series A.2
- The 2027 CGT change affects investors like him. Individuals lose the 50% CGT discount from 1 July 2027; eligible ESVCLP gains stay exempt.3,4
Why did TechnologyOne's founder choose early-stage venture capital?
Because he has seen what early growth can turn into, and likes opportunities beyond the public markets. Adrian Di Marco founded TechnologyOne, the enterprise software company, and ran it until handing over as CEO in 2017. It has been a public company since December 1999.1
His interview was published in June 2025, when Tall Order was still called Skalata Ventures. He is an investor in our funds, so read his comments about us with that in mind.2
“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.”
By the time of the interview he had invested in more than 30 early-stage tech companies in Australia and overseas, and in several venture funds, including ours.2
Why does he invest through funds as well as directly?
Funds cover sectors he doesn't know, and he invests directly in the one he does.
“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.”
“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.”
How Di Marco splits funds and direct deals
For a client who wants to back startups directly, his split is a useful test: direct deals rely on knowing the industry well enough to judge the company. How a venture fund works covers what a fund's fees pay for.
Why early stage rather than later rounds?
Because he wants to be involved when the foundations go in, which is also how he explained backing us.
“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.”
That is one investor's view of a fund he backs. More generally, seed and pre-seed companies are cheaper to buy into and riskier than later ones, and the range of outcomes is wider. Stage and fund size explains how that shapes a fund's results.
He also argues for growth that a company can sustain.
“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.”
What does he look for in founders?
Character first, then a plan to go global from one market.
“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 short. “Have a strategy to go global, focus on one market, and go deep. Pick one thing and excel at it globally.”
He judges people quickly. “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 wants a culture of accountability in place from the start. “We believe accountability delivers operational excellence, and it's very hard retrofitting an accountability-driven culture when a company grows.”
It is fair to ask a manager the same things: how they judge founders and support them after investing. How to vet a venture fund lists more.
Where does he see the next opportunities?
In AI built for specific industries.
“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.”
That is his view from 2025. Venture returns are uneven and a few companies tend to drive most of them; How venture returns work explains why.
What has changed since 2025?
The tax on gains. From 1 July 2027 the 50% CGT discount ends for individuals, trusts and partnerships, replaced by an inflation adjustment and a 30% minimum tax; growth before that date keeps the discount.3,5
Gains on eligible investments held 12 months or more inside an ESVCLP stay exempt, with a tax offset of up to 10% on eligible contributions.4 For a client who, like Di Marco, mixes funds and direct deals, the way each is held now affects the after-tax result more than before. The 2027 CGT changes has the detail; some rules are still in draft, so confirm with a tax adviser.
What advisers can take from this
- Funds and direct deals do different jobs. A fund covers areas the client doesn't know; direct deals rely on the client's own judgement.
- Fees are the price of the manager's work, so the question is whether the manager earns them.
- Early stage means getting involved while structure and board are set, with more risk and a wider range of outcomes.
- The founder qualities he looks for are a reasonable test of how a manager picks companies.
- After 1 July 2027, how a client holds each venture investment affects the tax they pay on any gain.
Frequently asked questions
He said funds give him simplicity and diversification, with exposure to sectors like fintech and agtech where he has no expertise, and he is willing to pay the fees for that.
Yes, mainly in software-as-a-service businesses, where his experience building TechnologyOne lets him judge the company.
In his view the structure and board are set early, so by Series A much of the groundwork is done. Early stage also carries more risk and a wider range of outcomes.
From 1 July 2027 individuals lose the 50% CGT discount, while gains on eligible ESVCLP investments stay exempt. Confirm details with a tax adviser.
Get client-ready PDFs of every guide
- A clean PDF of any guide to send a client
- An email when the rules change
- Early access to new guides and tools
- Nothing else, and you can unsubscribe any time
Talk to us about Fund III
Tall Order is a Melbourne seed fund. Fund III is a registered ESVCLP for wholesale investors. Justine Lum, our Head of IR, works with advisers and their clients.
Sources
- InnovationAus, TechOne's Di Marco steps down (10 April 2017): Edward Chung takes over as CEO; TechnologyOne public since December 1999. ↩
- Skalata Ventures (now Tall Order), Interview with Adrian Di Marco, first published on skalata.vc in June 2025. All quotes on this page are from it. ↩
- Australian Government, Budget 2026-27, Tax reform: CGT discount, minimum tax, negative gearing, venture capital. ↩
- Australian Taxation Office, ESVCLP tax incentives and concessions. ↩
- Federal Register of Legislation, Treasury Laws Amendment (Tax Reform No. 1) Act 2026, as made 26 June 2026. ↩