Oliver’s career backstory
Gaz:
Oli, welcome! Fantastic to dive into the backstory of investors, such as yourself, and I’m particularly interested to get stuck into the aspects of your involvement in tech businesses, on a technical level. Would you like to walk us through your background as we get started?
Oli:
Interestingly or not, I started in music funnily enough, as a DJ producer in London, and everything is a bit of a combo of happenstance, luck and serendipity. I was at a record label which was pre- iTunes, pre-iPod, and the founders said ‘we should start an mp3 downloads store!’
I was the only other employee and they've just said ‘OK, well I guess we have to figure out how to build a music download store.’ And that was the start of my journey into entrepreneurship, but really, into product management in terms of building stuff and figuring out how it would all work for users and customers.
Then, I moved to Sydney. And again, if you want to talk about luck, there was a company down in Melbourne that was trying to acquire a company that I had worked at in the UK just coincidentally. They had the licences to build music download stores for JB Hi-Fi, The Wiggles, Harvey Norman, ABC etc.
So they moved me to Melbourne so that I could work and help them build things because at the time, I was kind of one of the very few people experienced in that line of work.
Plus, a kind of interesting anecdote is my fun fact that every week, The Wiggles store would sell more tracks than every JB Hi-Fi and Harvey Norman track combined. Brittany, Justin, NSYNC, whatever. All of it combined, The Wiggles would sell more.
Gaz:
Fun fact that one!
Oli:
I was coming from the UK and had no idea who they were!
And then, eventually, I progressed into doing BD for MySpace, which became a role in Product for MySpace Australia, which then became a role as Head of Product for MySpace International, which included every region except for the US. I ended up being the Product Manager for 50 million users, I think?
A little while later I moved back to Sydney, and an old friend of mine was trying to take over a traditional finance broker business, and wanted me to get involved, so that ended up being my first foray into running my own business.
After that, my brother in law had figured out some cool ways to optimise cloud usage. So we turned that into a SaaS called GorillaStack, and we grew that into a decent sized company as well, with some really large enterprise customers, and that was acquired just a few years ago by a big Swiss public company.
Onwards to a couple of years as Chief Product Officer at Stake and now I operate as an independent Product & Strategy Advisor, in a somewhat fractional capacity.
Experiencing high growth in tech companies
Gaz:
Let’s talk about a high growth company like Stake and what your predominant role was there?
Oli:
Ah yes, well just like when MySpace came up, Stake was the hot ticket in town and I thought, this would be cool. When I joined, there were about 35 people, and I came on as the Chief Product Officer and built up the whole product team, which ended up being about 30 people by the time I had built it up.
That saw me being in charge of product, user experience and user interface, data, and it had me running the commercials for their SMSF (self-managed super funds) as well. So by the time I was finished there, they were the largest international broker in Australia, and I think the second biggest broker overall behind CommSec.
Product expertise in complex environments
Gaz:
I would love to hone in on the aspect of your main skill set that you bring when it comes to a product perspective, especially within large, dense and complex environments?
Oli:
I think what I've done over the years has worked with kind of subject matter experts who have deep insights and I can help them organise it into product outcomes. By that, I mean help them achieve KPIs, prioritise their roadmaps, translate that vision into clear outcomes, deliver it on time, create a consistent user experience, align stakeholders internal and external etc.
There's obviously a big mentorship piece as well, in trying to support people in growing their careers and then having an impact on the business. So yes - it's multifaceted. It's a framework that I have built and think about applying and it's about working with people through that framework, so they can deliver it as well.
Frameworks in fractional roles
Gaz:
How about if we view you in that fractional context now? It is a buzzword of sorts, but you seem to manage it quite well and it seems to suit your product-focussed working style?
Oli:
I think when I started out, it was very much trying to get the best way to work, but it was very much getting on with it. And flying as I go. But what I've been able to do and kind of realise, is that I have this framework and a way of thinking about things.
As I formalise that, it's made it much more straightforward for me to go in and support multiple organisations, multiple products, multiple outcomes at the same time because it now becomes quite like I’ve productised myself if you like. I can get people to the problem and attack those problems in a thoughtful way.
Oliver’s investment thesis
Gaz:
Fantastic, I love the way you articulated that, productising yourself.
Let’s jump to investing now, what’s led you to personally investing in a more increased fashion of late?
Oli:
Well, my first investment, would you believe, was Tractor! As I had been through the process of exits, I had gotten to know Matt (Allen, Tractor Co-Founder & Co-CEO) quite well, and he had been incredibly helpful with a few somewhat complex financial problems that I needed help navigating.
He mentioned what he was doing with Tractor, which really piqued my interest, as I really love the credit and debt space and that’s what kind of got me over the hump if you like. More generally, I like being involved in the industry, as it’s a great opportunity to stay involved and connected.
I write smaller cheques, but then I like to think, the cheques I write I try to add value to wherever I can, and it's nice to be able to support the ecosystem as well.
Gaz:
Any particular verticals that appeal to you directly, as part of your investment thesis?
Oli:
I really like credit and debt, I have four or five investments, Tractor being one of them. Reliable models, easy to understand, that’s kind of the core of my portfolio.
I see a lot of founders, and a lot of decks where people have built this amazing solution, and I like to ask how focused they are on the problem that it's actually solving. That’s a lot of what I think about when doing the product advisory as well.
How do we pull this back to the pain that people are feeling and their ability or the startup’s ability to cure that pain. So that’s what kind of gets me excited.
Why Tractor?
Gaz:
Is there a particular trait of Tractor that has stuck out to you as a core reason for being involved?
Oli:
Again, it kind of ticks the box in the credit aspect as well, but I have reinvested over time and it became apparent how talented the team is, how thoughtful the team is, and they’re obviously a leader in the field.
Tractor has stood out to me as the vanguard, the flagship player in this space, which is kind of what got me to double down, but it is also the humility displayed. I think at Stake, the brand was always very, very bold. At Tractor, there is a certain authority, but also humility and that drives up through the brand and through the way the team operates, throughout the team.
The best traits in founders
Gaz:
That’s so good to hear from your perspective. What's a particular trait in a founder or in an operator that you really resonate or gel with, Tractor company or otherwise?
Oli:
I think people who do what they say and say what they do. It sounds really simple, people turning up and people turning up on time, people who make it happen when they say they're going to make it happen.
It seems like such a low bar, but actually, that is really an outstanding trait that I think separates a lot of people I think in this industry, in that they can be a lot of talk.
I touched on it before, but also, people who are problem-led and have conviction around their area of subject matter expertise, but not being completely convinced on the way to solve it. Most of the brands that I would see are in the seed, or pre-seed space, and I’m always sceptical of people who have the strongest solution and the most conviction around that. I'm most impressed by people who have conviction around the problem. The fact that there are many possible solutions that could fix that thing, and find the right one to solve it.
The other thing is, my preference is for solid businesses, not moonshots as well. I've had a couple of conversations recently which have really kind of vindicated that as well. I think founders who have a good sense of what it takes to build a good business and not trying to send rockets to space. I think founders who build really solid businesses are a kind of attractive opportunity for me to get involved in as well.
Experiments and MVP’s
Gaz:
Awesome. And what’s personally motivating you currently as well? What’s moving you forward and really lighting up your interest?
Oli:
I've been really trying to experiment and MVP, so taking a leaf out of my own book lately. I’ve just launched out office hours for free for a handful of people to jump in and take time with me, and I want to experiment with what that's like. Just have quick, short, sharp conversations.
I'm really enjoying my coaching at the moment, which is working with founders for an hour or two a week and getting into their problems, and working through them trying to find frameworks or theories. I like to test the mettle of knowledge against a variety of problems or challenges or founders.
Connect with Oliver Berger HERE
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