Great founders thrive under pressure. Heaslip acknowledges the mental health burden of leading a company, especially after raising money and facing constant expectations. The "false summit effect" – feeling successful after every milestone, only to find another peak ahead – is a reality he readily confronts.
Chris explains, “What separates good founders from really great ones is being able to take on a lot of pressure and a lot of pain. Something people don't talk about a lot in the space is the mental health aspect of being a founder, having to raise money, having expectations from investors, employees, from customers, and then having to deliver on that. So you feel the weight of pressure that you have to deliver.”
“For us to do it as a public company, added this other level of pressure, which is why we never felt successful, because every single quarter, there was another goal that we had to hit and achieve in order to continue building the company.”
Complementary skills are key. Heaslip credits his success to his partnership with Elliot Crowther, a non-technical co-founder with a fierce drive and sales expertise. Their contrasting backgrounds and shared determination proved a winning combination.
Chris reflects, “Elliot was the absolute perfect person that I could have partnered with because we had very complementary skills. We were both non technical, which is insane, to start a startup without a technical co-founder, but we were both non technical, but we were both equally committed to win. We just had this kind of inherent drive to want to go out and quickly build something meaningful, serve customers, and provide value. His competitive cycling background gave him an intense drive to get on a bicycle and ride for five or six hours a day. So it's like that kind of background, taking pain, then bringing it into the business world, and sales, which is what he was responsible for, really allowed him to deal with the setbacks and the hard knocks that occurred.”
Don't just plan for the next raise. Heaslip advises looking far ahead, ensuring the current funding will propel you towards bigger milestones, paving the way for future fundraising.
He doesn’t overcomplicate it, “The number one thing for an investor is the size of the TAM. The question that you have to ask is are we looking to build a $100m company or not? Because if you are, the question is, where's that TAM? And the answer is probably not in New Zealand.”
“It's just not big enough to even justify raising capital and trying to build all the software. Considering first principles, writing a piece of software once and selling it multiple times is the whole premise of a software business. So you're limiting yourself if you can only sell this piece of software 20 times, versus in a larger market where you can sell it 2000 times. You can be the 10th biggest player in a market like the States and still be a $200 million company. It doesn't matter that there's competition, the question is, on some variable, are you better than the incumbent?”
That said, Heaslip has high praise for NZ-based development teams, “We're really proud we had all our engineering in New Zealand and we're really proud to build software in New Zealand and export it to the world. I think we shouldn't go away from that because New Zealand engineers have that number eight wire mentality of just making things happen. Building things and serving the rest of the world is the kind of mentality that makes New Zealand entrepreneurs really special.”
While stretch goals were the norm at Pushpay, they found that transparency breeds motivation. They cultivated an exceptional level of transparency on the highs and lows of the company. Heaslip's team celebrated every big deal, fostering a sense of shared purpose. Once they realised the importance of celebrating wins, achievements were recognised each quarter, rather than annually like many other companies.
“It wasn't until about four years in that we realised we were grinding people like a meat grinder. We had this mechanism telling us if we were winning every month and every quarter. But when we hit the monthly target, it was like, great – now the next target is this one plus 10%. So people felt like they were just on a treadmill, never stopping to celebrate the successes that we were having.”
They remedied this with quarterly acknowledgements within their teams, and also had an annual awards night. “It was a black tie event. In Seattle, people hate to dress up. But people came and we celebrated individuals who through the last 12 months, had either achieved something, and who were living out our core values, who served customers, and would give them trophies as a way to say thank you. It was people's favourite time of the year.”
Pushpay's story isn't just about building a global company; it's about the mindset and strategies needed to get there. Heaslip's journey, with its candid confessions and hard-won wisdom, offers valuable insights for any entrepreneur aiming to scale their dream.
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