How this founder took legal tech startup Dispute Buddy from zero to $2 million ARR in just 9 months

Dispute Buddy finds patterns of coercive control and other abuse in years of text messages so you can build your case.

This isn’t an instruction manual to grow to $2 million in annual recurring revenue (ARR). These are the things that worked for us as a team. Take what works for you and ditch the rest.

I’ll caveat these ‘Look what great decisions we made!’ by saying that a HUGE part of our success is down to privilege and luck.

My privilege comes in the form of being white, privately educated, fairly tall, and deeply loved and encouraged by my parents. I didn’t earn any of those things, but they do make a difference to how people treat me and the opportunities afforded to me.

And luck can’t be underestimated either. There are some market conditions (coercive control is being made illegal round the world, and we’re a tool to help people prove it) that are hugely in our favour.

Before we built, though, we wanted to understand not just the market timing, but what it was actually like to engage a tech startup.

Observing before doing

Chat to a few pre-revenue tech startup founders, and pretty soon you realise they have lots of experience in the problem they’re solving, and next-to-none in building profitable tech businesses from scratch.

Then lob a million bucks of pre-seed investment at them, and they’ll burn through most of the cash learning ‘how startups work’.

That seemed inefficient to me, so before starting Dispute Buddy I spent a good two years learning how startups work, and figuring out which factors increased the chances of being successful.

I started off by joining my local angel investment group Enterprise Angels. I didn’t have pots of cash, but I had other skills, like the fact I’d built and sold a magazine publishing business. And I gave lots of my time.

I even won a trophy: New Member of the Year Award 2021. I was so excited! My teenage son looked at the trophy and said “That’s just a participation certificate”, then drifted off to eat the snacks I’d paid for.

Through Enterprise Angels, I learned how to do due diligence and made 14 (tiny) investments. I got voted onto their board and invited to be a mentor at Startmate and Techstars Sydney accelerators where I read over 1,000 pitch decks, joined investment committees and mentored over 25 startups.

In January 2024, on the back of this experience, I took a six-month contract at Workzilla, a Sydney-based legal-tech startup doing product and operations when they were pre-revenue and a team of four. One of the co-founders, employment lawyer Danny King, ended up investing in Dispute Buddy.

It cost a fair whack of time and money to do all this research and learning; two years, plus thousands of dollars on flights between New Zealand and Australia to mentor founders, membership fees to angel groups, and let’s not forget the 14 investments; I’ve had a total of nones of dollars return on those so far.

By the time I graduated from my self-designed startup school and went full time on Dispute Buddy, I knew how I wanted to build our platform:

• A very narrow set of features, done really well
• Using jobs-to-be-done principles, so that we only build what customers were telling us they wanted
• And we’d raise capital as late as possible, staying focused on earning revenue from customers, not filling our bank account with investment dollars.

Speaking of investment…

VCs are not the only fruit

There are no venture capital funds on my cap table. In late 2025 we raised an over-subscribed A$765k pre-seed round from angel investors from US, UK, Australia, Singapore, and New Zealand plus Techstars Sydney.

We’re about to open our next round (late seed/early series-A) in October. We already have a lead, and I am planning to fill the round from angel investors again.

During the two years of pre-Dispute Buddy learning, I observed that founders who took venture capital unwittingly stepped onto a path that’s very, very hard to get off. It added more complications than they’d ever imagined, and often didn’t end up well for them.

A huge problem is that the only people educating founders about what’s involved on that VC path, are venture capital funds. Not a particularly neutral education.

Despite the whole ‘We’re founder-friendly!’ vibe the VC industry markets so convincingly (using the bulging budgets that 2% of every fund affords them), I largely observed the opposite when mentoring venture-backed founders. But you’ll rarely hear founders talking publicly about how VC funds behave, because the power imbalance is so uncomfortably disparate.

Of three successfully exited founders I spoke to recently, two of them said ‘I wish I’d never taken VC investment’, as it made it very costly (legal fees) to exit. The other person has a terrible story about what a VC did to them in their raise and exit, but wouldn’t allow me to recount it in this article.

For the unvarnished truth about taking venture capital, read Rand Fishkin’s Lost and Founder. He was the founder of Moz Marketing, and took it to $30m revenue before exiting. They’d raised venture capital in a few rounds, and he explains exactly how it works in his book.

I have found, on the other hand, that angel investors offer genuine support when things go wrong; which they always do.

During that pre-Dispute Buddy two years, I got to know lots of Australia and New Zealand’s angel investors. They mentored alongside me at Startmate and Techstars, were on the board at Enterprise Angels, and in the due diligence teams I was on.

I’d built a fantastic network of investors by the time I was ready to raise capital in Dispute Buddy. They perceived me as a peer, and had already seen how I worked.

VCs are not some kind of genius investors with a secret special formula to pick winners. They have absolutely no idea which startups will have outsize success. There’s way more luck involved than any of them admit. And just remember, they are not on your side, regardless of what they say.

Search for ways you are wrong

I am constantly looking for evidence that I’m wrong or have missed the mark, then very quickly acting on it.

A good way to do this is to ask yourself after every decision “What’s my rationale for this?” You should be able to articulate, even just to yourself, why you’re choosing a direction. The answer might be vibes in the absence of data, which is important to know, too. What’s influenced the vibes? Is it five conversations with customers that’s made you feel something you can’t put your finger on, or is it just what you’ve already seen work in the market?

When we raised our pre-seed round in 2025, I applied to Epic Angels, the world’s largest women-only investment group. The syndicate receives 100 applications every month. Ten are put to the investment committee, who select four startups to pitch to the angel investors.

Maaike Doyer, CEO, emailed to say that we’d made it through to pitch night. I emailed back asking for the un-edited feedback notes from the investor committee. I wasn’t so much interested in what they liked, I was only interested in where they thought Dispute Buddy’s weaknesses were.

Maaike told me I was the first founder ever to ask for that information. I was able to read the feedback, and address their concerns head-on in the pitch. There were lots of comments about defensibility. So I built a slide showing how we were building a moat.

There was one comment that described me as a bit annoying and overbearing. Fantastic! Good to know I was staying on brand.

Epic Angels ended up investing. As well as being able to address their worries head on, it showed them I can take and filter feedback and act on it, fast.

I’m comfortable being wrong. Every time I can iterate my product to be less wrong, that means I’m closer to helping our users to prove coercive control, access the justice they deserve and move on with their life.

At some point, everyone rebuilds their tech from scratch

While Dispute Buddy was going through the Techstars Sydney Accelerator in September 2024, I booked user tests with three people who’d been through awful separations. We’d built some code, and I was hoping we’d be able to launch into the market with that prototype.

All three cancelled. They had legit reasons; a child was sick, the dog died. Disappointed, I tried to rebook. They dragged their feet. But my gut told me why they’d cancelled. They couldn’t face reading the painful messages. Because I’d felt it too, years earlier when I had to gather texts as evidence for court.

They hadn’t actually said that to me. No one had. It felt like a huge risk to ditch the tens of thousands of dollars’ worth of tech and rebuild from scratch, but I just knew it was the right thing to do.

The day after Techstars Sydney demo day on 7 December, 2024, where I’d presented Dispute Buddy to a roomful of investors and founders, I sat down with Seth (who I’d only recently met, but is now our tech lead), a pack of felt tips, an A3 pad, and we sketched out the UI screens of a desktop app.

It was a completely different approach, one where the user could collate their text-message evidence without rereading a single painful word. It took about a year to re-build and test. Our earliest users came from a partnership with Australia’s biggest divorce-tech platform, The Separation Guide, in August 2025.

The re-build paid off. This is the product that’s taken us to $2m annualised revenue in nine months.

It felt pretty daunting to start again. What if the desktop app was the wrong solution too, and what if we run out of money before we could get into market?

Since then, I’ve watched all my founder friends rebuild from scratch at some stage. It’s expensive, it feels terrible at the time, and you may have to do it more than once.

And yes, we nearly ran out of money!

• Jenny Rudd is the founder of Dispute Buddy.