Diversity, tenacity and the School of Hard Knocks: Lessons from Dom Pym after serial startup success
Up co-founder Dom Pym reflects on his founding journey, shares key advice, and reveals what he’d do differently a second time around.
It was easy to find Dom Pym. He was the one drawing a crowd side-stage at Southstart, long after the end of his panel concluded. He was the man on the coach back to Adelaide, freely sharing startup wisdom with other conference attendees. They craned their necks and hunched into the aisle, just to hear him a little better.
And for a few moments, he was the serial founder and investor sitting across from me on the sidelines of South Australia’s growing tech conference.
Speaking to SmartCompany, Pym looked back on his history as a founder and co-founder in the local startup scene — a legacy that includes Up Bank, Pin Payments, Ferocia and his own investment vehicle, Euphemia, along with a director role at FinTech Australia.
That history brings a lot of recognition. So it was fascinating to hear that, if he could go back in time, Pym would seek founders and business partners who don’t resemble himself.
“All the businesses that I’ve started, that started off with half a dozen blokes in their 20s from university dorms and stuff like that, because that’s who I was at the time, they have all now progressed far beyond that,” said Pym.
“Looking back, I wish that we had done that earlier.”
Below is a transcript of our conversation, lightly edited for length and clarity.
Five key lessons from Dom Pym
- Don’t think you can do everything yourself
- Acknowledge your biases and hire beyond one degree of separation
- STEM education is good… So is the School of Hard Knocks
- Embrace diverse thinking
- Prepare the next generation for success
SmartCompany: What are you looking for in founders today? What makes you think, “This person has something I believe in?”
Dom Pym: I think it’s going to be different for every investor. For me, I back people, so I’m very interested in their journey.
I always ask people what they do outside of work. What are their other interests? What are their passions? What are they good at?
And I try and assess their moral compass, the ethical reason why they’re doing what they’re doing. How committed are they to the cause? Are they just doing something for a quick exit and to make money?
Or are they actually trying to change the way people interact with something, or introduce a new technology that helps feed the planet?
Then I think humbleness is another really big one. Selflessness, where people are able to recognise, sort of self-referentially, what it is about them that they can’t do.
A lot of the time I’ll be mentoring or introducing early-stage founders to other co-founders, or to senior employees, or their first employee. And a lot of the time that is to fill a gap.
If you want to be the leader of this new startup, you shouldn’t always think that you can do everything yourself.
Now, as a startup founder, you do do everything yourself, and that’s fine — like clean the toilet, wash the dishes, buy the computers, set up the operating system — you’ve got to sort of do everything. That’s okay.
But there’s certain things that you’re very good at, that you have experience at, or you studied at university, or you just have a natural aptitude for.
And then there’s other things that you don’t.
For example, at the moment, we’re working with a young founder who’s 26 and doesn’t have a lot of real-world experience after coming out of university.
What they need is a chief operating officer, or they need a chief financial officer, or they need a co-founder, maybe a technical co-founder, because they’ve come up with the idea.
We’re always very happy to back the person regardless of what the idea is.
If they’re a well-rounded, smart person, with a moral compass headed in the right direction, and they’re interested in disrupting, then oftentimes we’ll see them pivot their idea several times before they get it to market — and even potentially pivot it again before it scales.
So those little identification of gaps, and identification of the things that you’re really good at, are what I try to understand about people before making an investment.
Are there any moments in your own journey as a founder that you look back on and think, “maybe I would do things differently if I had my time again?” And how does that experience colour your interaction with new founders?
Not everything in all the startups that I’ve ever had has been perfect. I’m an advocate of lifelong learning, and I’ve made mistakes, and I’ve done things not as well as I could have.
I actually think that attending the School of Hard Knocks, the School of Perpetual Learning for Life, is something that is really important as an attribute of any founder. I mean any human, let’s be honest, but particularly a founder.
When I first started some of my companies, and I was in my 20s, I would have hired my mates, the people that I went to university with, or the people that I know, the people that I’ve worked with before, or the people that you don’t need to see their resume because you already know them. It’s easy to bring them in.
What I would say, looking back, is don’t have that bias, don’t hire with one degree to separation, try and meet with a broader array of people.
Diverse thinking covers all bounds. So if you can find the right type of people just through meeting lots of different types of people, then that puts you on a good path to be able to hire the right people.
All the businesses that I’ve started, started off with half a dozen blokes in their 20s from university dorms and stuff like that, because that’s who I was at the time. They have all now progressed far beyond that. Looking back, I wish that we had done that earlier.
My advice to young founders would be to try and be more diverse in the people that you’re meeting, the people that you’re interviewing, the people that you’re doing partnerships with, and if you’re outsourcing your technology, the people that you’re outsourcing to, so that you can just skip that whole era where you’re just working with your mates.
Sure, it worked very well, I would say, in early-stage companies, whether it be PayPal, or whether it be Tesla, or whether it be my companies for Ferocia, Pin Payments, Zepto, so on and so forth.
It worked very well in those companies, because we did have a rapport, and we knew each other very well. So working together in those very early stages was easy.
But I would say to people, don’t do easy, do hard, because hard is better.
Euphemia invests in women-led startups. Do you think there is a tendency among women founders to downplay their achievements when pitching their idea, as opposed to men?
I think it’s the same for men and women, anybody across the gender spectrum. I don’t think that makes any difference.
The ingredients you need to be successful are curiosity and confidence.
And it doesn’t matter whether you’re a man or a woman, you have a certain level of confidence and a certain level of curiosity.
What you need to do is, if you don’t have one or you have a little bit of one, then you need to work on that.
So a lot of founders, by the very nature of being a founder, will have confidence, but sometimes they don’t.
Sometimes I meet founders who are very shy, or don’t believe in themselves, or sort of have tall poppy syndrome or imposter syndrome, or they’re a little bit worried about whether or not they can do it.
I think that’s universal across men and women, and I think that you have to work on those skills.
Being curious in itself — to come up with the idea and to think that you can do something better than incumbents, or better than the big multinationals or whatever it is — demonstrates a certain level of sort of tenacity.
The saying ‘You need curiosity and confidence’ comes from Dr Karl, from on the radio when I was a kid. I’ve added to that: you need the ability to be tenacious.
In life, it’s ups and downs, peaks and troughs, and so you need the tenacity, the fortitude, the resilience to be able to actually get through that.
I would not differentiate the ability to be tenacious between men and women.
For many women, life gets in the way of being a founder, rather than their idea or their business. But you can say exactly the same thing for men.
On a recent panel, you described top-tier tech companies recruiting 18-year-olds while still in university. For older founders with a killer idea — those who have been to the ‘School of Hard Knocks’ — is it too late to get ahead?
The average age of a startup founder is in the 40s, I think it’s 46 or something like that. I would say it’s never too late.
The best type of founders to back are the ones that have been through the School of Hard Knocks, that have the experience, the ones that have sort of had to deal with those pitfalls and those challenges before.
I started by telling a story about a young founder that we’re helping who’s 26 and a little bit inexperienced, and we’re trying to fill the gaps for them.
There’s a lot fewer gaps to fill in older people, more experienced people, or they recognise what those gaps are, and I don’t have to dig for them. They just tell me right up front.
More mature founders in their 40s or even 50s, are in some ways the future of the startup ecosystem, not only because of the influence that they espouse.
What they can do is similar to what we’ve done, is that we can make millionaires, we can sell the company, we can do an IPO, and we can make sure we’ve got a good Employee Share Option Plan (ESOP).
ESOPs are pretty new in Australia. I’d say in the last 10 years, it’s sort of become a more commonplace thing. Airtree have open source VC. They have ESOP templates on their website. Any founder should just grab that template, give it to their lawyer, or fill in the yellow gaps, and make sure every single one of their employees is on an ESOP program, so they have equity in the company.
When that liquidity event happens in the future, you’re making future startup founders that can self-fund, that can sort of take time off a full-time job in order to fund themselves for six months or a year, because they’ve got the capital behind them.
I think that’s the only way that we see a multi-generational improvement in the current startup ecosystem.
Now, we didn’t have that, for example, when we sold Ferocia, the parent company. We didn’t have an ESOP program. We didn’t have all staff having shares.
What we did instead was when we sold the company, we made sure that there was a component of the sale that went to all the staff, including our fitness coach, masseuse, admin, reception, everybody.
Every single person in the company had an opportunity to share in the sale. And I think that that is what I would recommend to companies that don’t currently have an ESOP — or to just implement an ESOP.
There is a funding gap between capital that goes to male founders, compared to women founders and mixed founding teams. What are the most important steps we could take to meaningfully address that in the long term?
I think there’s two areas that I would advocate for. One is young females in STEM. Having a pathway for young kids to be able to become founders in the first place. And that’s an easy one that everybody says.
But I think the harder one is actually just the existing venture ecosystem is very male-dominated, and it’ll take generations to change that.
We actually back female general partners (GPs) in female-led funds, as well as funds that invest in women. And I think that that is an area in which we’ve seen an enormous amount of improvement.
About eight or so years ago, I could count on one hand, maybe just barely two hands, the number of female GPs in Australia. Now, the last time I saw the numbers, they were in the 30s.
But we need to see a hell of a lot more of that, because it’s just human nature to be drawn to yourself.
If you’re a middle-aged white guy with a beard, running a fund, and you’re meeting with people like that, there’s an inherent bias.
If we have more women leading funds, and more women partners in funds, and more women as investors, then I think that’s a really good way to improve the flow of capital to female founders.
And again, it’s not revolutionary. It’s not anything that people haven’t said before, but we try to practically make a difference by literally backing female GPs.
So whether it’s Flying Fox, Co Ventures, ALIAVIA, or Scale, we back them, because we’re trying to make that difference, and it’s a practical difference that can be made.
You’ve also thrown down the gauntlet and challenged Australian founders to build their own large language model (LLM) instead of relying on international LLMs in the AI race. Does Australia need its own LLM company?
It’s really more to illustrate the point that if you want to work at the core of AI with a generative LLM, then you’re going to be going off and working with Microsoft, or Google, or OpenAI, or DeepSeek, or whatever it is. You’re going to be going and doing that, which means you’re necessarily leaving Australia.
It doesn’t mean that you can’t work remotely, but you’re working for a foreign company anyway. So I think it’s more philosophical.
It was an example — not necessarily saying that people should do LLM. It could be blockchain, it could be the next Google Maps, it could be some new technology that’s disruptive. It could be fintech, for that matter.
Look at fintech as a sector, compared to all the other sectors in terms of capital deployed each year. The Early Stage Venture Capital Limited Partnerships (ESVCLP) restrictions and the tax incentives have just thwarted fintechs from being able to get access to capital.
Afterpay is not only the largest fintech, but the largest acquisition in Australian history. We’ve got Airwallex, and we’ve got Up, for example. We’ve got these great fintechs that are being built in Australia, and they just can’t raise venture capital. We did not raise a single cent for Up. It was bootstrapped. And we went out to try and raise capital, and we could not do it.
There’s nobody prepared to lead the round, and nobody prepared to provide that level of capital that we sought. We were going to do a $70 million seed round, and that would have been the biggest in Australian history, and there was no one to do it, right?
You necessarily need to go overseas, and that’s part of the motivation for us.
On the one hand, I’m on the board of FinTech Australia, trying to lobby the government and work with the Friends of FinTech, which is a bipartisan group in Canberra, and try and get them to change policy.
On the other hand, we’re actually just going ahead and doing things differently. For example, we created this new fintech fund, Triple Bubble, with an entirely new structure, which is an investment trust, rather than being set up as ESVCLP.
And my challenge to the industry, and existing venture funds, and the government, is that if you need tax incentives to run a successful fund, you’re not a very good investor. You shouldn’t have to rely on tax incentives to be successful. So forget about the tax incentives. Forget about the ESVCLP and the Venture Capital Limited Partnership.
Try and find new structures, new ways of doing it, where you don’t care so much about the tax incentive. Sure, tax incentives are good; they’re a good catalyst for momentum and growth. But I’m just saying you shouldn’t have to rely on them.
From our perspective, we want to be able to fuel the industry and provide a source of capital for fintechs in Australia, to help keep that talent, that entrepreneurial spirit, and that disruption alive here in Australia.
The author travelled to Southstart as a guest of the conference.
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