James Tynan

James helped scale Khan Academy from a YouTube channel to the world’s biggest ed-tech before taking over Startmate, Australia’s best accelerator. He invests widely in climate, education, health, D2C, and the future of software.

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"James has been amazing at shining a light on my blind spots and helping me confront scary or uncomfortable challenges. He cares deeply about our mission and us as founders. We’ve benefited tremendously at Vow from his approach."

Michael Carden
Elad Walach
James Bowe
Natali Tshuva
Michele Ferrario
Jack Zhang
George Peppou
Emma Weston
Get to know

James Tynan

We're one global team but we've got our own stories. Here's what makes us tick.

What advice do you live by?

"A couple of years ago I got quite sick. I couldn’t work for a while and even when I came back I was at a fraction of my former capacity. After raging against the injustice for a while, I started doing the work of finding out how to maximise the capacity I did have. The most impactful thing I learned was how to manage my energy. The basic lesson is that the different ways we motivate ourselves place different levels of strain on our bodies and minds. For most of my career, I motivated myself in very taxing ways. Fear of failure was my particular drug but competitiveness and a need to impress others are similar motivators that take a real toll. I remember working with a great coach (Peter Huynh) who asked me “what gives you energy back?” I had no concept that was even possible. Isn’t work supposed to be taxing and leave you feeling exhausted? If your work feels like running downhill is it really work? This is when I began being much more aware of when I was taxing my body and mind vs when I was renewing it with clean energy. Interestingly this was not about “work-life balance” – a lot of the things I find renewing are in the “work” bucket, like meeting amazing founders, or discussing new, interesting ideas. Growing this awareness made it really clear that the work I was getting the most energy from was investing and that was a big part of me eventually coming to Square Peg."

What did you take away from running Startmate?

"So many things. When I came back to Australia from the US I knew almost nobody. The Startmate community became my work family and were supportive in big and small ways I'll never forget. Before Startmate I thought the biggest high you could get was launching products that help millions of people. At Startmate I realised I got an even bigger buzz from finding and helping an individual founder do their life’s work."

What impresses you in the first meeting with an entrepreneur?

"One thing I actively look for is a growth mindset. The science shows that people with a growth mindset take on harder challenges, accept feedback more readily and are more resilient. It’s also a more accurate picture of the world - our brains really do grow and become more capable with effort. Startup founders don’t have the luxury of walling themselves off from learning. Around every corner is a new challenge in an area where they’re unlikely to have prior knowledge. So when I see someone who has turned themselves into a super learner I’m always excited to be around them."

What makes you excited about the future?

"I'm writing this during a pandemic and a climate crisis - so it's a weird time to be excited. But I've spent the last decade on the edge of multiple revolutions and that are all accelerating at a rapid pace. I'm so excited that Square Peg has an opportunity to help build the world we want to see on the other side of these crises."

What tech do you avoid in your personal life?

"Games. I was an old school PC gamer (Quake 2 anyone?) but these days I don’t have time for that level of obsession."

What was the greatest lesson an early job taught you?

james-tynan-what-was-the-greatest "If there’s one thing you learn at McKinsey it’s how to seek feedback. The ability to healthily and usefully integrate feedback may be the most important professional meta-skill. In the years since I’ve focused more and more on how to deliver feedback in a way that gives the other person the best chance of finding something useful in it. I think of it like a data compression problem. We all only have so much emotional bandwidth and “compressing” your feedback by owning that it’s just your own perspective (not a universal judgment) and anchoring it in specifics means it’s more likely to be received on the other end."

What’s something people outside of Square Peg wouldn’t know about working at Square Peg?

"There's a lot of laughter and silliness at Square Peg. I remember worrying a bit during the recruitment process that I'd detected an aura of seriousness and I wouldn't fit in. I was so wrong. If anything it’s an aura of goofiness and that fits me perfectly."

Where did you learn the most in your career?

"My most accelerated learning was at Khan Academy. I came on board just before we launched our first product when the team was around 25 people. We rapidly grew to over a hundred million users and hundreds of team members. I learned so much: what it feels like to be a leader in a product-led organisation, the challenges of growing a team, the importance of user research and having a clear go-to-market strategy. I also learned about my limitations. I was a firefighter by nature and as my responsibilities grew my calendar became maxed out with what my teams needed everyday. So my biggest realisation was that I needed to better manage myself in order to get the best out of others."

Why should someone build a startup?

"Most people shouldn’t. It’s so hard. Do it if it’s in your bones and you’re obsessed and nobody else sees the world the way you do. If you do make the jump, make sure it’s for something that will make a difference in an area you care about. Going big makes sense for two reasons. First, a big mission can be a motivator for you and your team. Second, you take just as much risk and do just as much work for a small business as a big one – so make the potential reward equal the risk."