James Tynan: from cleaning car parks to Principal at Square Peg Capital.

"You’ve got to cultivate an inner compass. I naturally look outward and react to what other people think. The best move is to spend time working out what I think."

Short Cuts is an interview series in which Upside faculty and participants answer eight quick questions about their background, ambitions, and the superpower they’ve always wanted.

Multifaceted, James started his professional life as a debating coach and car-park cleaner.

Having moved on to become a founder and operator, he then decided to take on the role of CEO at Startmate. Unfortunately, he became ill and was unable to work for a time. 

After realising that what was helping him get his energy back was working with founders, he decided to dedicate himself to that all the time.

James confesses that he had considered himself to be pretty awesome as a founder and operator, but he came to realise that he is best as a cheerleader on the sidelines.

He currently lives in Sydney with his wife and two young sons.

James, who did you look up to when you were younger?

Aragorn, Eddie Vedder, and the Wachowskis.

And who do you look up to now?

Abraham Lincoln, parents with careers and complicated kids, Peter Attia, and Esther Perel.

Tell us about the most valuable life lesson you’ve learned so far.

You’ve got to cultivate an inner compass. I naturally look outward and react to what other people think. The best move is to spend time working out what I think.

Describe what success looks like to you.

Being healthy, with a happy, thriving family and close friends. Having work that I love and am good at. Working with people I really like in a place where I can be my best self.

Tell us about something that you’re curious about at the moment.

Psychedelics and direct brain stimulation as tools for mental health.

What brings you joy?

Talking to an awesome person and grokking a cool idea they’re working on. 

And when kids do cute stuff.

How would you describe your leadership style?

Look at this amazing thing we can do over here, let’s gooooooooo…

If you could have one superpower, what would it be?

The ability to quantum split myself and live multiple lives doing different things. Ideally, being able to somehow draw on the experience of those other lives in this one.

---

We’re all a work in progress.

Upside Founder Programs help founders become the very best leaders for their businesses as they grow from late Seed stage and Series A to Series B, and beyond. Applications for the 2022 program have closed. Join the waitlist for 2023 now and you’ll be the first to know when applications open.

Upside Founder Programs are proudly supported by KPMG High Growth Ventures and Microsoft Australia.