In 2018 the company I co-founded failed. My life went to ground zero all areas.
I'd spent 10 years coaching people in sport before I entered the startup game as a founder, and when it became my turn to be the athlete again (this time in business) I got the help I wanted instead of the help I needed.
In sport, we coach athletes within the context of competition. In business, we just talk to a founders axiom truth, which is the narrative they want to be true.
This gap is everything, and it’s why founders fail.
When I closed my company I started to ask one question. “What would need to be true to develop capable founders in startups, the same way we develop elite athletes in sport?”
This became my obsession. My life's work.
/ Coach Leighroy /
Some people know me as Leigh Sherman, others know me as Coach Leighroy.
I’m the founder of Hillspeed Group, an international coaching company and product lab that merges my background in elite sport with my experience in high growth tech companies and startups.
“Hillspeed is built on the same principles we use to develop elite athletes in sport → because that's where my story starts.”
→ I went from athlete.
I competed at elite level in triathlon and swimming, and my vision was to represent my country.
But at some point, 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 coach.
That led me to study sports science, where I spent years working alongside Australia’s top sports scientists, coaches, and administrators.
→ Then back to athlete.
Eventually, my career shifted from sport to retail, then to digital businesses and startups.
🔶 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 had built something my customers loved, but I was suffocating under the weight of growth → stuck in a game I was never prepared to play”
→ Everything came crashing down
By 2018, I had exhausted my resources, my team and my mental health. I had to stop.
It took 6 months to get the customers off my platform because they were small businesses and relied on our infrastructure.
“I lost my company, my stability, and my identity as a founder → life went to 0 in all areas.”
If you want help mastering your game as a founder
→ The dark side
As I started to support other founders it became obvious to me that everyone was injured on some level (to use a sport metaphor).
In sport, injuries are part of the game, you address them. Pro athletes know this.
In the startup world everyone wants to avoid the tough conversation with founders and their advice is some form of “just run faster”.
“The silicon valley mindset in startups was intoxicating and its negatively impacted a generation of capable athletes.”
Own your game
→ Compelled to act on what I knew
In sport, a certified sports coach has a fiduciary responsibility to prevent your athletes from injury.
In the startup ecosystem I realised nobody held that level of responsibility for founders.
The VC’s, accelerators, advisors, mentors, none of them focused founders on the fundamentals because that conversation doesn’t make you cool in the founders mind.
So we leave it to founders to figure out the fundamentals, and they try → but interpreting mountains of sporadic, biased advice is hard.
Synthesising advice is a learned skill that founders and athlete’s don’t have initially. That’s why in sport we have processes for working with athletes.
“We needed to fundamentally disrupt the way we support founders to step into their potential for scale.”
Let’s build your authentic leadership system for winning
→ 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 now had a long list of coaching and training knowledge in every aspect of human performance from the last 2 decades of experience.
Time to be a coach again!
“Coaching is about caring for an athlete’s performance across a path of growth.”
If you’re ready to own your game
→ Why am I called Coach Leighroy?
Coach Leighroy is my professional alias.
A reminder to myself and a commitment to my athletes 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, and I work with athletes all around the globe.
“High performance is demanding. You need the right approach to your sport or you will get injured.“
Own your game
If you are a high agency founder and subject matter expert at your game, Hillspeed coaching will help you own your path of growth like a founder-CEO professional athlete.
I’d be honoured to work with you.
/ Coach Leighroy /
Own your game