My biggest mistake: Jill Berry, co-founder of Adatree

In June 2019, Jill Berry founded consumer data rights company Adatree alongside her colleague Shane Doolan, and by October 2021, Berry was named as the emerging fintech leader of the year at FinTech Australia’s Finnies awards.

It’s clear Berry is no stranger to the world of finance, but just like the rest of us, she’s also no stranger to making mistakes.

As Berry tells SmartCompany Plus, her biggest mistake came to its head about a year into running Adatree. It’s a mistake that not only affected the business, but one that left her “pretty broken” too.

The mistake

Ultimately, Berry says her mistake comes down to “just trying to take on so much”.

At the time, the founders were focused on growing the business and getting clients. And while Adatree did have some software engineers on board, Berry says she was pretty much doing everything other than engineering.

“Often I’m kind of the stoic person; I’ll be like, ‘alright, I’m awfully productive, so I can just kind of do everything’,” Berry admits. This included taking on website development; writing terms and conditions; product development; financial modeling; all the way to accounting and tax returns.

“It was literally everything possible.”

Berry sums up the mistake as “trying to be the hero for way too long”, without getting any help for it.

“And then of course, by the time I did get help, I was pretty broken,” she admits.

The context

Some may assume that if a leader is trying to take on every single role, it’s because they need — and want — to have control over everything. Berry says for her, it definitely wasn’t about that.

Instead, it was because of a “really difficult balance” where startups can only hire people when they have the money to do so.

“You can do so with grants, revenue or a capital raise. And I really wanted to delay a capital raise as long as possible, so that we could dilute the business less,” Berry explains.

There wasn’t a strict timeline to when Adatree wanted to raise capital; it was about “having the product market fit, having something that was really working, having customer acquisition and having revenue”.

“Those are really important things for me to really back myself on,” Berry explains, saying that many companies do raises solely based on a PowerPoint.

“I wanted to be able to say, ‘no, this is actually working; this is what we can do; these are the clients that we signed; and this is who really believes in us’,” she says.

“I didn’t want to just talk; I wanted to show.”

But delaying the capital raise meant delaying new hires, leading to Berry taking on much more than she should have for her own sake and the business.

The impact

The cost benefit of this mistake is that Berry learnt how to do a whole lot of other things that she usually wouldn’t have.

“But the downside of it was ultimately when you’re doing everything, things slip through the cracks,” she says.

It also meant those around her felt the need to push themselves, as they believed it was what was expected; some new hires even admitted to Berry that seeing her work all weekend made them believe they had to as well, but that’s not the precedent Berry was trying to set.

These cracks weren’t just visible at work either. Berry admits she was spread “really, really thin” even in her social life, choosing to miss out on birthday parties or other fun events because she felt like she had to be working.

“At that point you’re thinking ‘there’s no point having way more ownership of a company if I’m not actually living either’,” Berry says.

The fix

Berry admits it all got a lot easier when Adatree started to go down the capital raise route about 18 months after its launch.

“It actually only took us about three weeks, which was a nice reflection of all of the hard work we had put in,” she says.

The $1.2 million seed funding round was oversubscribed nearly three times, and included investments from Tyro Payment (where Berry and Doolan both previously worked) co-founder Peter Haig and chair Kerry Roxburgh, as well as investors at Equity Seed and Eleanor Ventures.

Immediately after the raise, Adatree hired four more people for product development, marketing and sales, and outsourced other responsibilities. Berry says having people purely responsible for other aspects of the business — and taking herself off them — made her think ‘wow, why didn’t I do this sooner?’

While Berry doesn’t show any signs of regretting her decision to delay the capital raise, she does say her life got “noticeably so much better” following it as she was able to delegate.

“I rarely work on weekends now, so I really try to have that work life balance.”

The lesson

Berry says the lesson she takes away from this mistake is that just because she is the leader, it doesn’t mean she has to sacrifice herself.

“I really need to be ruthless about what I delegate and what I outsource as well,” she admits.

Berry also says she needs to be an example for others, and make sure her team are being examples to each other, too.

“If I tell people that they need to relax on the weekend, then I need to take that advice myself.

“It seems so obvious now,” Berry admits, “but it didn’t make me as productive as I wanted to be.”

“And it definitely didn’t make me a better CEO.”