MEET THE COACH
Some people know me as Leigh Sherman, others know me as Coach Leighroy. I founded Hillspeed Group to challenge the fundamentals of leadership engineering and founder coaching.
Hillspeed is a coaching system built on the same principles we use to develop championship athletes in sport, because that's where my story starts.
/ Coach Leighroy /
I went from athlete
Competing at the elite level in triathlon and swimming, my vision was to represent my country at a professional level. But early in my twenties that dream felt out of reach, burnout set in, my training habits changed and I began questioning how my development as an athlete could have been different.
To sport coach
I studied sports science and management at Federation University where I spent half a decade working alongside Australia's top sports scientists, coaches, athletes and administrators.
Back to athlete
Eventually my career shifted from sport to digital and I reinvented myself as an athlete of industry.
- →By 2010, I was winning hackathons and building startups.
- →By 2014, I built a VC-backed tech startup.
- →By 2016, I moved to Berlin as one of the first Australian's to go to Techstars, a tier-1 accelerator.
“I was suffocating under the weight of my own success, stuck in a game I was never prepared to play.”
The crash
Four years into the journey of founder I had exhausted my resources, my team and my mental health. I really had no idea what great looked like at the level of the game I was playing. I had no choice but to stop. And it took 6 months to move customers off the platform because they had nowhere else to go. The frustration was immense and the cost of failure was prolific. I lost my company, my stability, and my identity - life went to 0 in all areas.
Seeing the dark side
In the aftermath of my experience as I was searching for my next role in life, I spoke to hundreds of founders. It became obvious to me that on some level all founders were injured (to use a sport metaphor). In sport, injuries are part of the process, but you address them. Every athlete knows this when you are injured. In the startup world however everyone wants to avoid the tough conversations with founders and share some form of “just run faster” advice. Once I saw this I felt stupid for not trusting what sport taught me. I was completely blinded by the silicon valley mindset of grow at all costs.
Questioning everything
If you are a certified sports coach you have a fiduciary responsibility to prevent your athlete's from injury. In the startup ecosystems I realised nobody held that level of accountability for the founder, not because people didn't care, but because the systematic infrastructure of support needed innovation - the same way athlete development has been innovated over the last 3 decades.
“Founders need feedback systems like athletes, that help them bring into alignment their potential for scale.”
Back to coach
Between 2018 and 2020 I built the Company Model framework while working inside scale-up companies Zwift.com and Booking.com. Then I switched into education and training and worked for industry giants such as Jack Delosa, Dan Martell, and I studied coaching under one of the top 5 life coaches on the planet Benjamin J Harvey. I launched the Hillspeed coaching protocol in 2022 and developed that into a self-coaching system in 2025.
My commitment
Coach Leighroy has been my professional alias since 2022. A reminder to myself and a commitment to you that I'm here to win with you, at speed, without burnout.
I live on the Northern Beaches of Sydney, Australia, with my beautiful family. I work with athletes all around the globe, from North America to India.