Coach Leighroy: Thriving Through Growth, Structure, and Overcoming Burnout - Insights from Peak Performance Sport

Jun 2023

Coach Leighroy is an elite athlete, a tech founder and a startup coach helping founders build a more efficient path to growth and reach scale-up before running out of steam.

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“Burnout is the reason every startup company fails.”
Coach Leighroy: Thriving Through Growth, Structure, and Overcoming Burnout - Insights from Peak Performance Sport
“You can't force your will on people. If you want them to act differently, you need to inspire them to change themselves.”
by Phil Jackson, a former professional basketball player and coach of the Chicago Bulls

About The Episode

Given today’s tough economic environment, many startups are now struggling to survive after having raised record amounts of capital. In this episode of The Founder Spirit Podcast, we'll take a deep dive into Coach Leighroy's story as an elite triathlete turned tech founder and startup coach, and uncover how he leverages his athletic background to assist entrepreneurs in achieving their goals.

At Hillspeed Group, a coaching platform for early-stage technology, Coach treats founders like athletes and empowers them for success by pursuing a more efficient path to growth and offering tech founders a more supportive, performance-focused environment.

TUNE IN now as we explore his distinctive approach to coaching while emphasizing the importance of commitment in both sports and business.


Coach Leighroy is the Founder and Managing Director of Hillspeed Group, a coaching platform for early-stage technology companies. As an elite athlete, he trained under some of Australia's best sports scientists and performance coaches, and also worked as a coach himself, training professional athletes across triathlon, cycling, swimming and different football codes. 

Having worked in growth companies from scale-up to enterprise, Leigh founded PantreeCo, a business-to-business software platform for the hospitality supply chain. When he closed it down a few years later due to burnout, he knew that it was time to get back into coaching and help improve the way that we train and advise founders. 

Leigh wrote curriculums for coaching and mentoring programs globally, ran master classes at tier 1 accelerators, and has personally worked with thousands of founders around the world since 2018. His coaching philosophy is to treat founders like athletes and look at growth through the lens of velocity, risk, and trajectory.

At Hillspeed Group, Leigh developed a new methodology to help founders build a more efficient path to growth, and reach scale-up before running out of steam. These days, he is training digital athletes and offering tech founders a more supportive, performance-focused environment.

Coach holds a Bachelor’s degree in sports management and marketing from the Federation University in Australia. 

Episode Transcript

[00:04] Jennifer Wu: Hi, everyone, thanks for listening to The Founder Spirit Podcast. I'm your host, Jennifer Wu.  In this podcast series, I interview exceptional individuals from all over the world with the founder spirit, ranging from social entrepreneurs, tech founders, to philanthropists, elite athletes, and more. Together, we'll uncover not only how they manage to succeed in face of multiple challenges, but also who they are as people and their human story. 

You can find us on Apple, Spotify and Google Podcasts, as well as social media and our website at

Given today’s tough economic environment, many startups are now struggling to survive after having raised record amounts of capital, so joining us today is Leigh Sherman, a triathlete, a tech founder and a startup coach, to talk about his journey of entrepreneurship and coaching startups.

Leigh is the Founder and Managing Director of Hillspeed Group, a coaching platform for early-stage technology companies. As an elite athlete, he also worked as a coach himself, training professional athletes across triathlon, cycling, swimming and different football codes. 

Having worked in growth companies from scale-up to enterprise, Leigh founded PantreeCo, a business-to-business software platform for the hospitality supply chain. When he closed it down a few years later due to burnout, he knew that it was time to get back into coaching and help improve the way that we train and advise tech founders. 

Leigh wrote curriculums for coaching and mentoring programs globally, ran master classes at tier-one accelerators, and has personally worked with thousands of founders around the world. His coaching philosophy is to treat founders like athletes and look at growth through the lens of velocity, risk and trajectory.

At Hillspeed Group, Leigh developed a new methodology to help founders build a more efficient path to growth, and reach scale-up before running out of steam. These days, he is known as Coach Leighroy, training digital athletes and offering tech founders a more supportive, performance-focused environment.

Hello Coach, welcome to The Founder Spirit podcast! And thank you for taking the time to join us today.

[02:26] Coach Leighroy: Hey Jennifer, what an intro, thank you very much. It's an absolute pleasure to be here. 

[02:31] Jennifer: Growing up in Australia, what motivated you to become an elite triathlete?

[02:36] Coach: The answer's pretty simple, it was my Dad. And I remember the exact moment he dropped the idea of enjoying the feeling of greatness in the arena of sport. And we were on a camping trip, I must have been nine years old. 

And sport is obviously a big part of our life. I'm one of four kids, I'm the eldest, so we were always doing sport as activities. But on this particular camping trip, Dad told me about his experience as a swimmer in the school team at high school. And the way that he described it, I felt like I was there. And that was the moment when I started to identify as an athlete, not just a person who enjoyed sports. My life became very different from that moment. 

The story that my dad told me was about being on the blocks in a team relay in swimming, and relays in any sport are really exciting. And I remember that vividly, so much so that I made it my mission to become the swimming captain. And I was the first person in my school to become a senior swimming captain before I was a senior.

I capped out in swimming early, I had a lot of success in events I was doing, and I started to do open water swimming, and this sport called triathlon was on TV. I remember looking at these athletes that would get out of the water, jump on a bike and then run. I just thought that was the next level that I craved. 

And so I got into triathlons, and if you're good at swimming in triathlons, you come out of the water first, and it's a really good feeling because you're in front. And I was fit enough to hold the front on the bike, and then eventually, the good runners would catch me. 

But I really enjoyed the idea of being at the front of the sport for so long. And as great athletes developed around me, I was part of their training team, it just became a mission in life that I really liked. And triathlon wasn't big in the late 90s, these days it's much more popular. 

Becoming a swimmer graduating into a triathlon was a natural flow of events. But I'm sure we'll get into this, but how I handle that transition, I would do it differently if I had to mentor my son going through the same thing next time.

[04:57] Jennifer: And speaking of the three disciplines: swimming, cycling, and running in  triathlon, how do you train for the triathlon races, both physically and mentally?

[05:06] Coach: Well, I did it the wrong way. So an elite swimmer's calendar will look something like, you wake up at 4am, you are in the pool by 5am, you swim for maybe 2.5 hours, depending on what age you're at. Then you'll go to school, or if you're professional, you just go home and sleep, then you'll come back in the afternoon, and you'll do two sessions, and you'll be swimming somewhere between 8-15 kilometers a day in the pool. And you do that 6 days a week, so I built up to that level of training work. 

And when I started to get into triathlon, I added essentially cycling and running onto that. Now, I took out a few swim sessions, but that's the wrong way to go about trying to advance into a new sport. You can't add onto what is already a peak performance program. And I didn't realize this was a mistake until I was past burnout. 

And that's why I became a coach because many people around me during that time didn't advise me otherwise, because I was a good swimmer. They just allowed me to continue to be a great swimmer, to also try and develop as a cyclist and run. And that kind of workload will kill any 19-year-old.

And I didn't realize that I had 5 years to develop into a good runner because, as a young athlete, you want to be the best in the world. But the great athletes, they really make a difference once they get to about 25 and they're on the world stage from 25 to 30.

So I didn't have great advisors around me, and I handled it the wrong way, and that's ultimately why I became a coach. 

[06:40] Jennifer: When you decided to become a coach, you had trained under some of the top scientists and sports administrators. And what did you learn about programming growth?

[06:52] Coach: I remember at first I paid to do a subject at Deakin University, and Sports Management was one of their pinnacle courses, it was called Coaching Principles.

And so here's me, I just represented my state in this particular year, I'd qualified for the world champs in my age group for Australia. I thought I was doing pretty well, and I sit in this room, and it's full of world Australian champions. And that was the moment when I realized, okay, once you get to the top of any sport, there's a whole new level again. 

The way that I saw the professionals play the professional game was very different to how I thought I played getting to the professional level. And that particular subject taught me how you step into that professional game over a series of years.

Growth has to be earned at a foundational level, and you have to stack it. And what's important about stacking something is… think of a stack, like a house of cards. If you get the foundations wrong in one area, it's obviously gonna fall once there's too much weight on one part of the stack of cards. And so as you build your stack of cards, you have to step back and look and make sure it's evenly built. This is just a process of being intentional, that’s what I learned in that very subject. 

And then over the next couple of years, working under different coaches, I was able to understand that in practice, in different sports, how does that look like in football versus when you're working with a swimmer or a runner, how you move someone through a series of growth efforts and allow them to recover.

It's really different at the professional level than what it is getting from an enthusiast to the professional. And I just found that so enticing and for the rest of my life, I was like, I wanna play at the top of whatever field I'm in because it's hard to understand it until you're there.

[08:47] Jennifer: Interesting. And looking back now, what other lessons do you think you took away from peak-performance athleticism? 

[08:56] Coach: Sport is a really great activity because it teaches somebody about commitment. You can interpret what you want commitment to be in any way you want, right? Just showing up every week is commitment, that level of commitment has an impact on people. 

And this is why sport is such a beautiful thing in many parts of our world because it creates community. Community requires commitment. So if you can commit, you start to get the benefit of community, and then that reward gives you this reinforcement to commit more, which then you get the benefit of personal growth.

So commitment is this really awesome thing. The more you lean into it, the more it rewards you, and it's this upward cycle of growth. That's how you get into high performance in any area of life. You just commit for an extended period of time. Sport teaches you that, and it rewards you for the longer you commit.

And, like I said, you don't realize how much commitment is required to play at the top of a sport. And I think having had that level of exposure at an elite level and professional level in sport, when I came to business, I knew business is a low barrier to entry like sport, but it's gonna get tough at the top.

And I think a lot of people underestimate what it takes to be great in business because they haven't been great in other areas. They haven't committed long enough to understand that greatness is just about showing up, it’s just commitment, and that's applicable to anything. 

[10:24] Jennifer: And while you were training professionally, you had also worked a number of odd jobs to support yourself. One of these jobs was critical in forming your understanding of entrepreneurship. Can you tell us what that job was and what you learned from it?

[10:40] Coach: Absolutely. I've always worked odd jobs. When I moved back to my hometown in Melbourne after graduating from college, I got into retail and selling jeans and t-shirts, and it wasn't where I was expecting to be, but the roles that I wanted in my profession weren't available at that time. And this was a good way to bring in some cash over the summer period.

But I got from that experience many things I didn't expect. And I recommend anybody, particularly if you have kids, to push your kids into an environment where they can learn to sell. Retail's really great because people walk into the store, so you have a captive moment with them, and you have things to sell.

And so it's a good environment to learn how to interact with people, but you realize that businesses do not work unless that sale can happen, so it's a really important function to how the world works. And if you want to make some extra money or you want to build a company, go learn to sell first before you start the business. Go, get a job in retail. It's very rewarding, but it's also challenging. 

[12:03] Jennifer: You founded PantreeCo, which is a B2B SaaS platform serving small and medium-sized businesses in the hospitality supply chain. What motivated you to make the change from the world of elite sports to tech entrepreneurship?

[12:24] Coach: Well, when I was at college, this new service on the Internet came about, it was called Facebook, it was 2005. When Facebook came to my campus, it was the first time I realized the potential of digital. The product changed so quickly and that took me down this road of learning digital marketing at the time. 

And then I found myself doing hackathons and then learning about startups. And that just blew my mind at the time. But the more I was around it, the more I understood it. I built a couple of projects, and I understood what it might take.

And one day, I was talking to a friend who is in hospitality. He just had a very clear problem to solve. And we kind of joked around that, Hey, I could build an app for that. So we did. But the more that I looked at this, the more I realized, oh, there's some interesting dynamics about the business model around this app.

And so I just kept thinking about it, and playing around with it over two years, that's when I met my co-founders, and we decided to turn that into a business in 2014. 

[13:38] Jennifer: And what was fundraising like for you as a first-time founder?

[13:44] Coach: Fundraising for me is pretty easy because what a good fundraising round requires are the things that I do really well. I talk to the investible vision, and I move quickly, which is what an investor wants to see. So it's easy to get the first dollars, but the follow-on raises become a lot more challenging, and I didn't understand enough back then how much you should be preparing for the future, always. 

It's 2014. Silicon Valley is all about “move fast, break things, get as much money as you can, and change the world.” And it was an infectious culture. And there's a generation of us, as founders, who all were defined in some way by that. 

It comes with consequences, and I learned those consequences the hard way. But there certainly wasn't people, and this still isn't today - this is why I'm a coach. People don't tell you as a founder, ‘That could get yourself in some trouble if you keep going down that path or your model isn't quite right’.

No one tells you this - you are the head of the business. It's like life, no one tells you how to do life, it takes you a while to realize I've gotta own it.

[14:57] Jennifer: That's right - you realize how hard it is to actually build a startup, even though you have $10 million in the bank. 

[15:04] Coach: The money in the bank makes it even harder once you've had that experience. Because it just then comes with this pressure to figure it out quicker. And if you felt pressure before that, now you feel this crazy sense of squeeze, and you're in the middle as a founder and the team members.

And I think one thing I didn't understand, and I really wish someone had just said, ‘Leigh, stand back and just look at this’, is I allowed the pressure to permeate into my team. And so they became stressed. If there's one role of a founder, you have to protect your team so they can do the work for you. And I just didn't understand that at that point. 

[15:45] Jennifer: How important do you think investor recognition is to a startup? This idea of taking venture capital money versus bootstrapping or getting other sources of capital…

[15:55] Coach: Yeah, this is such a good question. I'm gonna say something here, and to whoever's listening in the audience, you're gonna interpret this the way you want to interpret it, not what I'm about to say, because if you've got this idea that you want funding as a founder, it's gonna be very difficult for you to hear any other storyline.

But I would say this, you really want to understand what VCs expect because what they say to you what they want is very different to what they need. And the good VCs will balance that relationship, what they need and what the founder needs. But at the end of the day, they're giving you money, and they need that money back in an order of multiples.

And if you give them a signal at any point on the journey that you aren't gonna return their money back multiple times, not only will they become disinterested, they may start to find a way to get the money back somehow to de-risk their world. Now, I didn't experience this, but a lot of founders do.

I had incredible investors, like incredible investors. Most of them were angel investors, so it was their own money. And then we had some commercial, venture-backed funds, like Techstars was one, and they all gave me space to build and crash the business. And I was terrified when I had to say, we have to close, most of the investors were like, ‘Well, we thought you were gonna close about a year ago, so you went longer than we anticipated.’

But I was really petrified, because when you say it's over, that's the moment when everything becomes real. I was terrified. And I'd say to anybody, go and understand the VC world a little bit more. Building a bootstrap business in the early days is so much more rewarding. It's actually probably no harder than raising VC capital, but get to a point where it is a business and then assess what would be the value of taking VC capital now; what could we do with it? Then you're in a great place to go. 

The great businesses now are all bootstrapped to start with, all the really good investible ones, and it's because it forces you to be a great founder from the start. And so VCs are looking at these businesses now, and they've been going for 2-3 years, and they're actually profitable, founders have got great work ethic, there's good structure. Give them 10 million, and they'll actually grow versus trying to figure it out.

So I think the landscape is changing for VC monthly. But if you are out there and you wanna raise capital, understand what you're paying for on that capital. 

[18:29] Jennifer: Yes, and also understand the personal motivations of the person that's gonna be sitting on your board.

[18:37] Coach: One of my athletes, he's about to raise a round of capital, but it also could just be really great as a bootstrapped, profitable small to medium enterprise vehicle. But he wants to go down the VC track. And I said, think of it this way. You own 80% of your business, and your co-founder owns 20%. Here's what's gonna happen - when you take investment, you will now own zero, and you'll have to vest your ownership over the next 4-5 years.

So you'll go back to owning nothing, basically. You'll be required to vest, and you're probably gonna be stuck with this for the next 10 years. You have to get real with that. And if you're comfortable with that, okay. 

But I think most people take the money and it's easy. You go back to zero, you don't have anything that's truly vested in most cases. It's an insane ride, so you gotta look at it from all angles. 

[19:32] Jennifer: It's a good way to think about it. On the business side of PantreeCo, what are some of the tough challenges that you've had?  

[19:40] Coach: That's a good question. I think it's easy in hindsight to answer this, but the real tough part was managing relationships and your own energy. The more you find yourself feeling burnt out and fallen into a burnt-out state, the energy you give to relationships is harder to manage, and therefore you get less from those relationships.

And then you can very easily start to feel resentment within those relationships. As soon as resentment creeps in, it's game over for that relationship. And this typically happens with co-founders, and it certainly happened in our case. We were just really burnt out individuals, and our default was to look at the things that we resented in each other.

This is a really common story between co-founders, but you see this then happen at an investor level. You have to manage your own energy - that's the hard part because then you can't do anything else in business. 

[20:41] Jennifer: So, in terms of managing relationships, managing your energy level, what would you have done differently?

[20:49] Coach: Well, I wish I existed to help me as a founder. And what I mean by that is, I really wanted a coach or an advisor around me who understood what I was building. I got introduced to quite a few coaches and advisors, and everybody who worked around me were phenomenal, but I never felt like someone truly understood what myself and my co-founder were building. It was just us two. We always felt like there was nobody we could truly rely on for help. And so I wasn't coachable for that reason. 

So, to answer your question, I really wish I had a coach that could understand what we're building and turn that into a set of structure and numbers. With structure and numbers, it's now a game, it's a sport. And now I can go back into that athlete persona, and I can play the sport, and I'm very competitive. But I need to know the structure, and I need to know the scoreboard. Without that, you can't play the game. 

So I wish I had turned business into a structured sport and reevaluated what game needed to be played at different stages as PantreeCo evolved.

And I just didn't understand that this is how you succeed at business. That's what I do with founders now. 

[22:05] Jennifer: I think it's difficult because you're a first-time founder, everybody gives you advice, whether or not you want it. They wanna help you, but they don't actually really know how to help in a sense. That's at least my experience.

[22:20] Coach: Yeah, absolutely. From my perspective, it's less that they don't know how to help. It's more that there's just no structure for them to help consistently. This is why sport is such a good environment because if you bring a coach into a sports team, that coach will know how to operate immediately without even having met any of the other staff.

In startups, particularly in these accelerator environments, which I've been around. I was one of the first Australian founders to go to Techstars, which is a tier-one accelerator. And so I've seen inside of these environments, and they've changed. But you get these mentors around founders, and it's like this. 

If you wanna run 5K, and you've got three of the best coaches on the planet, now all these three coaches have very different training methodologies. I know this because I've watched them. Now you're getting three different pieces of advice on the same goal, and then those coaches go off and do their own world. 

And in the startup world, it's like, we've just given the founder value. One, you have to decide which coach do I believe in. And even if you choose a coach, that's just the start part. Now you actually have to go do the training, you have to implement what they said, and the coaching changes based on your implementation. This is really well understood in the sport. 

But in the startup world, this is actually what we do, and we do it with VCs and advisors, and the founders are sitting there going, 'I don't know how to interpret this'. So what the founders end up doing is trying to make it comfortable for the people that are helping them, because you're grateful. So you're trying to help the advisor feel a sense of connection and meaningfulness, and so you start doing some work together, but is the work the right work? Well, there's no system for founders to look at this. 

It's actually crazy how we build startups. Let's put a lot of ideas and people, and energy in a room and hope a business comes up out of it. That's kind of like how we're still building companies. Hopefully, we're not gonna be doing that in 5-10 years, but that's the state of startups.

[24:19] Jennifer: Especially the first few years, when you're building a product, and a team, you're bombarded with so many different challenges, whether it's HR, or keeping the company afloat by raising enough capital, so it's all just a bit of a chaos. And then there's different people giving you different types of advice. 

You mentioned that you had participated in Techstars. How valuable do you think accelerators are in general in terms of personal and business development?

[24:49] Coach: If you wanna raise capital and you are at a stage where you're investment-ready, they're great vehicles, particularly if you're a new founder, because the accelerator will write you, usually, an investment on a note, a SAFE (Simple Agreement for Future Equity). And so that is very easy then to get a bunch of other investors and close the round.

It removes a lot of the friction for getting your first $500,000, $1-2 million. But you've gotta be ready, you've gotta be investible during that accelerator, because if your investment window is too far after the accelerator, you've lost the momentum.

But that's really all an accelerator is these days. If you go back to arguably the first accelerator, which was Y Combinator in Stanford, Paul Graham was just creating an environment for creatives to make something. Essentially, if I was to paraphrase what he was doing well is he took some people who had potential to build, write code, design, talk to people, customers, and he said, ‘I'm gonna create a space for you to do this, and I'm gonna shield you from the world.’

I'll give you a little capital, enough to have your ramen and survive, but I'm gonna protect you from everybody over here who thinks this is crazy, and you just go build something and let's see if a company comes out of this. Yes, some great companies came out of it, and he kept creating a space for founders to launch new ventures.

Now this model has expanded. Techstars was probably the next most obvious model. It's a bit different in how it's run as an accelerator, but essentially it's still, 'Let's give a founder a space to create something.' These days it's less about that because when I went there in 2016, at that point, accelerators were hitting maturity anyway, and you really had to be in the top 1% of founders in your niche to get in.

So it’s becoming a recruitment drive, like selecting athletes into an academy - that's kind of what an accelerator is now. But if you are not gonna learn to be an athlete in these environments. So, unfortunately, it's not breeding better and different founders. It's just accelerating what exists today. So I think I'm less excited by the accelerator environments these days, and it's certainly my motivation to create more growth-focused environments for founders. 

[27:09] Jennifer: What do you think the accelerators and the startup coaches are missing today, when it comes to nurturing founders?

[27:18] Coach: We don't have a consistent system and structure to have a dialogue with founders. That's what I've built by default in my world, so I can talk with my athletes, have a dialogue about growth. So we are aligned but on a broader ecosystem, not just in accelerators.

And we don't have an environment to look at undeniable metrics. I refer to this concept called Axiom Truth. And Axiom Truth is essentially, if I say it, it’s truth. And if you think about the pitch deck that a founder creates, this is a great example of an axiom truth.

Here's a deck that represents what I'm building, and I give it to an investor, and their only way to interpret me is what they're reading. And so, to them, that's their understanding the founder through that investment deck. Now obviously, they'll make their decision up on what is real and what's not real, but they can only judge the founder based on what's in that deck. And the founder's only gonna put in the investment deck things that make them look good. 

So this is the problem with startups. You have to move away from an axiom truth to more of an undeniable truth. Like let's agree on a structure, and then you tell me where you sit on that structure. And now I've got a measurement or baseline measurement for where you're at.

The hard part about this is it's really raw. Because when you pinpoint someone's real fitness level, let's call it on a map. It's often a lot more beneath where they think they're at. And that can feel really emotionally defeating. My role as a coach is to make people feel amazing about that because now that's real, and we can build on what's real versus being deluded about maybe being more advanced than we thought we were.

[29:06] Jennifer: When you are doing a startup, many times we have our own hypotheses of what we think the market looks like, especially in b2b. You have a set of assumptions when you build a startup, and then you go out there in the real world. If you're lucky enough, you get to talk to some people. People give you different feedback depending on the company. And it's very difficult for founders to actually go through this process because this process can take years.

And then also, your first set of 10 buyers who are your early adopters are not necessarily a signal for your sustained market either. So it's always testing out your hypothesis. Who's buying my product when I'm into my second year of the startup, who's going to buy my product three years from now? It's constant R&D, trial and error, and trying to figure it out. So I feel like the challenge is to sort through the noise to find the signal.

[30:06] Coach: It's such a good point. You're reminding me that there is just so many variables in building a startup, isn't there? And our role is to eliminate the variables. 

Elon Musk has this really, really great quote. I think about it daily because it keeps me focused, and I say it to every person I work with. He says, 'Look, we build rockets. And when we build the rockets, we don't think we are right. We know we are wrong. It's just a question, to what degree are we wrong? And every time we move forward, we're trying to be less wrong'.

That's the game. And to your point, there's so many questions. We might understand something today, but then in six months time, it's gonna change. So long as you are playing the game of looking at how do we be less wrong the more we grow, that forces us to build on what we know.

And I see a lot of founders grow, and you see them 2-3 years later, and they haven't leveraged what they knew. They're just constantly chasing versus building on what things they did prove out, or they didn't prove out. But there's no foundational strength. 

And yeah it's a very, very complex game. You're right, it’s ridiculous. You should never start a startup unless you're crazy. 

[31:18] Jennifer: It's true. It's hard to be a founder, and that's why not everybody can do it, right? 

I wanna take us back a little bit to PantreeCo. PantreeCo had facilitated over $26 millions in orders, and that's roughly 5% of the market in Australia, in your niche market. Yet in 2018, you had to close it down.Can you tell us what is the story behind that?

[31:45] Coach: Yeah, some context. The platform was a commerce platform in the supply chain of hospitality. So essentially, we just took an order from a cafe and or a restaurant and got it to their supplier, like the coffee roaster or the milk supplier, via a digital channel. So orders were on phone, fax, and email and SMS.

And every cafe has about 10 suppliers. And so there's this crazy network effect and everyone was on their own communication channels. So the idea that I had back in 2012 was like, what if everyone was just on one platform? Wouldn't that make sense, right? 

To your point, though, once we started to get in, and that was the reason I went from it being a hobby because I looked at the potential of this business and it had a network effect. If I could get one cafe, they would send orders to 10 suppliers. Now I've got 10 suppliers who are seeing PantreeCo and they probably have 50-100 cafes each.  And I said, if we could tap into the network effect, this will work.

The second hypothesis was not only should we tap into the network effect, we have to turn a supplier into a customer in under 30 days. For example, if they got an order from a cafe and they have 50 other cafes, we have to figure out how to get those 50 cafes on our platform. And we've got a 30-day period, which is four ordering weeks.

If we couldn't do it in four ordering weeks, they would stay on their traditional channels, phone, fax, email, cuz they didn't wanna change. Nobody wants to change behaviors - this is the hardest part about tech. We're not in the game of building products and features, we're in the game of helping people break habits so they can use our product and features.

So they were the two hypotheses that we proved out. What happened as a result of that came a lot of requests for our product to go on certain directions. I didn't know this at the time, but looking back, I didn't understand the game we were playing. We are in the game of orders, getting orders from one side of the marketplace to the other efficiently and reliably, and our game was to increase the volume of orders.

Now what levers do we have to do that we can bring on more buyers, we can bring on more suppliers, or we can increase the volume of the already existing orders. They're the only three things that would increase the volume of orders. If I had known that that was the game, I would've been a lot more structured about how I built and brought new buyers into the network and new suppliers.

But instead, as a young co-founder CEO with very little product management experience, I was focused on the feature set that the suppliers wanted. And there was a lot of variability; it just pulled us in a direction of serving big customers and small customers. And we weren't focused and we burnt out because, well actually, I thought we didn't have the capital to build out the team necessary. But in actual fact, if I had the capital, I would've wasted it anyway because I didn't know how to product-manage growth. 

So growth made us founders burn out and once we were burnt out, we started focusing on the problems and not the company. And it's eventual game over at some point.

Burnout is the reason every startup company fails. Everyone says there's reasons, it's burnout because if you're not burnt out, you keep going. And most people stop for a reason, but it's because they just can't or don't have the energy to go find another reason to keep going. That's the definition of burnout. 

[35:13] Jennifer: While we're on the subject of burnout, as mentioned, having already dealt with it earlier as an athlete, why do you think burnouts happen?

[35:23] Coach: I know exactly why burnouts happen. Burnouts happen because how our mind thinks about the future is different to the reality we're living in. So when our expectations are noticeably different to the reality, this starts to become a strain on us as humans. 

And think about this in your own life, it could be a financial situation or fitness. I want to be fit, but I feel like I'm just stuck here at the moment. If your mind can see a vision in the future, but your reality doesn't feel like you're moving in that direction, you feel strain in the body. Now, what the body needs is a system to get from where we are today to that future.

If you can find that system and you can start building momentum, the feeling of stress is under control or subsided. If you can't, if your body doesn't have a system, you start to produce chemicals that you just don't want excess of, cortisol in the body. This is how you lead to then bad decisions, bad decisions get you further away from the reality. I'm just not gonna get the million-dollar raises, right?

And at some point, you give up, and that's what burnout is. It's the point where you stop. 

[36:43] Jennifer:  It's really interesting because I went through my own burnout, when you are used to getting your way and succeeding, and all of a sudden you are faced with multiple failures and the fear then creeps in, and that fear becomes stress on the body and in your brain. 

And when you're stressed and when you're tired, those are not good times to make decisions. So I feel like with sufficient rest, you can always recover. And then when your mind and your body feels good, that's always a good indicator to go on.

[37:16] Coach: Yes, it’s not like we as individuals give up because we can't keep going. What often ends up happening is you realize what it will take to get there and you already feel spent or like, ‘I don't have the energy.’ 

And so from my example with PantreeCo, I realized when I lost my co-founder, and then I tried to rebuild the team without him, we partially did it, but then I realized we had a lot more work to go to get it to a place of stability. I am physically and mentally not ready for that, I'm not in a great state. So what I would need to do is go away and rest, and then I'd need to come back. And I looked at that as an option. And at that point, I was like, ‘I'm not motivated to come back.’

I wasn't passionate about the customer's problem. Because when I came into the startup, I was really passionate about network effect and the product we were creating to activate that network effect. That brought me alive as an entrepreneur solving that problem.

But as we had to deal with the problems of the industry, I felt a lot of weight dealing with the industry itself. And so I wasn't motivated to keep going to serve the end customer. And that's a really great reason to stop because you're not gonna do much, be of value. Yes. That's why we called it quits.

[38:37] Jennifer:  And what can founders do to avoid burnouts? 

[38:41] Coach: You need a model for growth, and that's the foundation. In sport, you have a training model for whatever sport you're creating. In business, you have to have that. Now, this is not something a lot of people talk about, so most founders be like, ‘Well, I don't need that.’

But you do. You need a model, and you need a team around you. It could be a board, it could be just close advisors, people who can keep you accountable playing to the model. And if you're playing outside the model, they should tell you, and they're there for you. You need to know that there's people who care about your capacity to play the sport because it's hard.

I think today we are very good at going off and doing life by ourselves and taking on our own problems. We've gotta be a great parent and we've gotta act like we've got it all under control. We shouldn't be that hard on ourselves. 

So founders need a model for growth, and you need a team and change that team out. You are gonna be doing your business for 5-10 years, make sure your team around you are fresh and let them know that you appreciate their support.

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[41:18] Jennifer: Leigh, speaking of that model, you came up with the Company Model at Hillspeed Group, which is the structure that you've developed in terms of helping startups to grow. Can you tell us what it is and how you came up with it?

[41:38] Coach: Yeah, absolutely. So, I'm gonna run you through visual, and the visual will help you understand how the model came about. 

So, growth is movement and there are lots of things that move, so we have to decide what's important. Now, the thing that moves in a business that's important is the customer, it’s the market. How a customer finds you and then makes a decision to purchase from you, and then hang around and continue as a repeat customer. Think of that journey as a timeline for that individual. 

So a really great exercise that anybody can do. You can do this whether you're in a job for a company, or you are a founder of a company. You get a piece of paper, and you put yourself in the shoes of the customer who's around the business you're in.

And you write out their name, so you adopt that persona. You write out Jennifer, And then you list the interactions Jennifer's gonna have - finding your business, becoming a buyer in your business - a customer, and then adopting the product and staying around. So I arrive at the website, I book a demo call, I discuss with the technical pre-sales. And these are just not an exhaustive list, but a list that the next customer might take. Now think about that journey, and we chalk that up into a start, a middle, and an end.

And this is what we call a growth engine. And now, our goal is to get more Jennifers to the start of this growth engine and through this to the end. And once a Jennifer's at the end of this growth engine, we wanna keep her. And that's the game we're playing in the world of tech startups. Find Jennifers, bring them into our world, and then don't let go of them. Don't let them churn and stack more Jennifers on top. And over time, we get this compounding effect. So this is the market, that's the game. 

There are only three things now that us, as the founder or the business, have to manipulate that game. We have people; we have the products and systems within the company; and we have finance, revenue, money, capital, whatever you want to call that.

They're the three things that's all a business is. And you use those three things to move the market. So now we've got two pillars. We've got a market pillar that moves, that’s what drives growth. We've got a business pillar, that's what enables growth. Now who makes the decisions? Well, it's the leaders.

And in my case, working with founders, it's the founder, they're the first leader. So a founder has these three things that I can work with to make sure that they're using the business assets in the right way to move the market. And those three things are their strategy, so how they think. 

I just ask them, show me Jennifer's customer journey, and they'll show me it. And I'll go, okay, cool, what part of this is true today? Can Jennifer do all of this? Yes. Okay, cool, so that's today's marker. Show me what Jennifer would be doing in six months. Does the piece of paper change? Ah, yeah. She would be doing this and this and we would make more money off her.

Now we've got two pieces of paper, this is now base camp. How are you gonna get from here to here? What's important about how you use your business, your people, your finance, and your product? That's called strategy. How we're gonna climb up the mountain and get from base camp to base camp.

The thing that keeps you on track to the base camp is the numbers you're reporting. So we have to make sure that there's some numbers that represent how well we are moving from that reality to the future reality, so strategy reporting.

And what's the one thing that I can influence as a coach? It's the founder's environment, internally in their head. How they're thinking through this, their confidence, their internal capacity and self-belief, and their external environment. That's the most obvious one, and that's why accelerators exist - put a founder in an environment conducive to growth, and by default, they'll grow.

And I'm working with those nine levers within the three different growth pillars to always assess: where is the founder now? What's true about now? Where does the founder think they're going? What's true about that? And how are they moving?

And where I used to do this wrong and the reason I came up with the Company Model, because I was just like a lot of the investors that I found frustrating who would just tell me advice - I started out giving founders advice. And what I realized I was doing is I was commenting on a founder's business through my lens of the world.

And let's go back to our example before, we have three running coaches giving you advice; they're commenting on what you want through their lens of the world. The way that we are gonna help this generation of founders and the next, is we have to get really good at commenting on the founder's view of the world.

And that requires us to first articulate their Company Model because then we can talk to that. It's neither wrong or right. It's just what the founder is. And now you're talking to the capacity of a founder. 

So you can have two founders in the same industry. One's got very different skill set and aptitude for building, so you would talk to them in a very different way. But right now we talk to both businesses the same way because they're the same business. This is the missed opportunity of performance coaching in founders, but it requires a model. 

[46:54] Jennifer: Interesting. How do you know when it's a business problem versus a human problem?

[47:02] Coach: That is a great question. The leader pillar, leadership, it's usually seen in reporting stops. 

How common, Jennifer, is a founder who has investors and doesn't send an investment update at the end of the month? It's just so common, isn't it? It's one of the most common things in the VC world, no matter what an investor will say. A majority of founders, I would say, end up not sending the update. 

And the reason they do this is because the update doesn't reflect the work that they feel they've put in. The numbers aren't usually going up. And they know judgment's gonna come from the other side of the table, so they don't send the investment update because they're already in a tough place. I don't need any more judgment. I'm already a fragile state. 

So you usually see reporting drop off, and if reporting isn't dropping off, then you wanna make sure that how the founder thinks about the numbers, the people around them are aligned to that. So there's an undeniability when we say that number is X, it's undeniable to the group.

And that's why I say if the founder needs somebody around them, but those people around you are only important if the way that you read the numbers is the way they read it. If there's two interpretations, then you may as well not have people around you, because they're only distracting you. 

[48:28] Jennifer:  In my own experience, it's very difficult for a startup to find really good board members and really good investors because once the VC has invested money in you, you've sold them on this big vision and what your 3-year financial projections are, and usually you miss those projections even if the VCs take a haircut, let's say 50%. So you go from a collaborative relationship to an “interesting” relationship with your own investors. And these are the people who believe in you, they put in the money, but it's very, very difficult. 

And then everybody plays that game actually, like everyone in the company has a persona, even the board members and the investors have a persona and they know that they have to play that persona to get you to the direction where they want you to go, even if they're a minority shareholder and may not have much effect on the company at the end of the day.

[49:30] Coach: Absolutely. this is one of the dangers right now. We've seen the last 5-10 years, the growth in funds, Venture capital and angel investing funds has gone crazy, and accelerators, there's a lot of capital available. 

One of the unspoken dangers about this expansion is that you have a lot of people now in investment roles who have not experienced either the founder journey or the high growth journey. 

I didn't understand high growth until I worked at Zwift, which is a virtual cycling platform, and with scale. That was when I was like, oh, right, okay. idea of getting to the professional level in sport and realizing, okay, now there's a whole new game.

A lot of the people in  investment are inspired by that early traction. But then as soon as a business starts to form, you start to see a P&L that you can read consistently. These investment characters start to influence, like they wanna flex their muscles and be like, great, we've got a business here, and they start treating it like a business.

Now that's okay if you're building a small or a medium or even a large size enterprise, but if you're looking for investment grade returns, the outliers, as soon as you started treating the business like a business, it was game over. These are not businesses, these are vehicles for discovery. And the reason there's so few great founders on the planet is because this is really difficult.

It's very difficult to ignore value today and keep exploring for more value, at risk that you might lose it all. But, VCs  want 1000 times returns. And I'm seeing a lot of people around early stage companies, and just as the founder starts to get a signal from the market that they could be doing something special, everyone starts to get into formality mode.

And, more founder dreams are being killed than made. And, what it's doing is everyone in the startup ecosystem, not everyone but it's become the new job. Startups now are, general career path. And if you want to be a great founder, you have to navigate this, and now that's even more tough. 

When you and I were building startups, founders were the crazy ones. And now you're getting a lot more structured people coming into leadership roles. This is good, but sometimes you are turning businesses into too much structure too early on it. They need to be able to run fast and uncover interesting value. It's hard.

[51:58] Jennifer: You talked about treating the trajectory of growth in terms of different base camps. And you also treat founders like athletes and help them develop the foundational strength to scale. What foundations are we talking about here?

[52:17] Coach: Well, the three foundations are always your leadership pillar, your market pillar, and your business pillar. And you can look at those three growth levers in each to figure out an equation that might give you the best sense of stability in those pillars. And that changes at every stage, from 0 revenue to 10K. 

But when you have a prescription for what to do - we think we need to do this, we don't know whether it's right or wrong, but we think this is the best use of our time. When you've got that, you work on velocity, run fast in that pointed direction. This is different to speed; velocity is about force of movement in a specific direction versus covering ground over time. 

But when you get signals that your direction needs to be reevaluated, or we need to stop and we need to learn what just happened. This is the point where you can increase your trajectory and it's often done by bringing new skillsets or new perspective to own the things that you've just learned.

So if you can move quickly in a direction and then have people own the foundational learnings, you get these beautiful trajectory uplifts and then an extreme force forward as a unit, as a company, and then this uplift. You've got velocity and trajectory and you're playing this. 

The real game you're playing when do we move from moving fast to learning is a game of resilience. You're always trying to figure out how resilient do we need to be today so that we're light enough to move quick, but we're not frail enough to be crushed. And every time you grow, you need a new level of resilience. So resilience is how you look at velocity and trajectory, but really you're just looking at, am I managing the business assets and to effectively manipulate the market for where I want to be. 

Now I work with a seed stage startup at Christmas who had 2 million in the bank, no customers, no revenue, and they were optimizing in market for a certain usage pattern. So they wanted to bring people to their product and use it in a certain way. How we would look at the business assets is very different to a founder that I'm working with who wants to drive revenue now. 

And so there's no standard rule book for this, there's only a standard structure. We're asking, well, what's important to you as a founder? Do you want a volume of people in market moving towards this? Or do we want one person? We charge them, we learn, we charge two, and we grow slowly. It's all comes down to what the leader wants. And that's influenced by, unfortunately or fortunately, capital they've taken.

Because if you've taken VC capital, we've gotta play a quick game in market; we can't be slow, at the same time we've gotta learn. So to answer your question the long way, there's only ever three things that are moving: market, business and leadership, and we're just managing that movement in context to what we want to achieve today.

And what you said before is we are always looking at what might be needed in the future, the deals that need to be closed. So it's this very interesting game of dancing between reality today and a future state that we'd like to create. But this is what we do with athletes in sport.

It's actually really, well, it's proven. I mean, if a 16-year old, middle distance runner presents themselves to a coach and says, I wanna win an Olympic gold medal in seven years, there's a structure on how we take that athlete. We move them through development stages of growth, qualify them into the world rankings, get them the experience they need, get them into Olympic qualifying, get them to Olympics, and give them a chance of success.

By no means do we guarantee that that athlete a gold medal, but we can put them on a path that's optimized for that result. So it's easy to apply this into a startup world. We just, for some reason, we're not doing it enough. 

[56:09] Jennifer: This is why I find it so interesting. You found this more structured approach to putting startups on a path of growth. 

Speaking of resilience, how do you work with that human element? How do you work with founders to improve their own resilience? Because at the end of the day, that's why they burn out is that they lack the resilience to continue. And that's mental strength.

[56:36] Coach: That's a good question, I like your questions. That part is about compassion. And that's actually been the journey for me, caring about that before you care about the business. 

When I lost my company and I started advising and mentoring, I was just about the business. Like I would come into a founder's world and I'd start helping them see their business and sure, everyone else was trying to do that too. But what I realized over time, because you can break relationships really quickly when you are pushing in a direction that they don’t know if they should go.

You've gotta start from that human. Originally my Company Model was just market and business, it didn't have the leadership pillar. And I realized I was finding it very difficult to translate my model to somebody else. Everyone looked at the model and was like, it's really amazing, thank you. 

But I looked at the way that they used it, and it was very different to how I used it. And I realized when I talked to a founder, I was imprinting into the conversation an analysis of what I saw their leadership traits to be. And because I had a bunch of experience I could lean on, I could fill the gaps.

Now a less experienced person couldn't fill the gaps, therefore they weren't able to get the same results from the Company Model. So I was like, there's something missing. That's why it was a leadership pillar, but the leadership pillar doesn't mean anything unless you care about the leader.

And I've really enjoyed (it) over the last couple of years. I feel super grateful for when I work with the founder. Other than my family, like I'll do anything for founders who trust me with their business. And I think when I come from that place, it makes the conversation about resilience on a whole new level because we trust each other, we can really push boundaries. 

[58:22] Jennifer: So give you an example, there's a founder that I know he's really burnt out. He's been working on his startup, it's been three or four years now, his choice is either to shut it down or keep going.

But his wife's not really very supportive of his startup at this point. And, he came to me a couple of weeks ago. What would you advise him to do?

[58:47] Coach: Well, I'd ask him what he wants to do, have you asked that question to him? not what he thinks he should do, but what he wants to do. 

[58:53] Jennifer: I think he wants to keep going. He really believes in it. 

[58:56] Coach: Then I would just help him understand what keeping going looks like from how he thinks about it now, because it'll be a certain way and he won't be seeing all possibilities. 

And from that conversation you extract what's undeniably true. If you did that, what would then be true in the future? Let's see if we could reverse engineer a different way to get to that result, because it's the result you care about. And is there different ways? And you just start looking at this from a different perspective. 

The part you mentioned, which would be the red flag for me is that his support network, primarily his family, are a resistance. He has to solve for that resistance because that's his environment. You have to address that as part of the leadership model. And if it's unaddressable, unfortunately the environment is saying that he can't keep going. So unless you change the environment, which when it's a significant other, it's really difficult. 

It's always just a set of questioning and the founders always get to the answer that's right for them. 

[59:59] Jennifer: These days as you see it, what are the common mistakes made by startup founders?

[01:00:04] Coach: I'm gonna answer it a different way. I believe you should only be a founder if you understand the problem you're solving. Now, a lot of people will say, I understand the problem. All right? I'm not talking about the surface level problem that your product addresses, I'm talking about why that problem exists.

The way I phrase it is, you need to know the problem beneath the problem. Why is the industry that you're serving stuck there? Why does it happen that way? Do you know the history of this? Have you been inside this industry for long enough to see why it's stuck? And therefore your solution will be considerate of that. 

If you don't understand the problem beneath the problem, what you'll end up doing is first understanding that before you end up truly landing on something great. Sure, you might have luck and build something and get your first even $1 million in revenue, but you'll really stall between $1-3 million if you don't understand the macro events.

I'd say just don't be a founder unless that is true. And if it is true, you'll usually get pulled into being a founder. It will be a calling. you won't be able to stop thinking about the problem. And then one day you'll be like, I've just gotta do this. That is a really great entry point into being a founder.

Having said that, go and start a startup or a project. Sure if you're passionate about it, absolutely. These things teach you a lot, but treat it as a learning project rather than a big business. Because I think a lot of founders still think that you can come up with an idea then build the solution and that'll be a great company. I just very rarely see that play out in history. 

[01:01:41] Jennifer: And what do you wish to shake out of every founder in the first five minutes of coaching?

[01:01:48] Coach: The truth, the undeniable truth of their position. What I've learned over the years is that they have to shake me out too. We have to both get extremely vulnerable around their world. They have to know that I got their back because I'm not judging them based on where they're at. I'm judging them on how quickly we can get to an honest, undeniable truth of where they're at. 

And if they let me in and see that, I have to step it up now and I have to show them, now I have to figure out what intelligent things could I say that would actually help this founder. Not just give ideas like Hey, you should do this, but what do they want in terms of moving forward?

So I have to shake out the undeniable truth. And with that, I've gotta be a reliable person to them. I've gotta show up to another meeting. If anybody is listening to this, this is the one thing that we can all improve the startup ecosystem. If we all just do this, we will uplift the ecosystem together, and it is a follow-up meeting. 

If you have one meeting with a founder, you must have a follow-up because they can only implement what you say between the dots. So the interactions are the dots, go let them do the line between the dots, follow up with them. (It) doesn't even matter what you say in that follow-up meeting, but you'll be a person in their world that they feel they can trust and that will bring them alive like nothing else. 

[01:03:10] Jennifer: And how do you differentiate what you do with startups, vis-a-vis other startup mentors or advisors?

[01:03:20] Coach: That's a good question. Well, at the end of the day, I'm just another human passionate about this space. That's what I do love about the startup ecosystem is there's a lot of passion and the more people that come in, the more perspective and diversity. But there definitely is a place now for a structured role, and that's how I'm different to most people. 

There are a lot of other people like me, they're not easy to find and when I meet them, I feel they're very different. And we are different in that we can bring structure to the table that would benefit everybody else. It brings out the other advisor's core skills at the right time, in the right way. It brings out the founder's desire and commitment in the right moments, in the right way. 

I'm a good person to have in the room or a person like me who can work at the fundamentals. That's how I differentiate myself, but I'm by no means the only person doing this. 

[01:04:12] Jennifer: And tell us some of your success stories at Hillspeed.

[01:04:16] Coach: Well, I haven't yet had a founder that isn't happy, and sometimes the engagements with founders are short, sometimes they're long. I used to think that it was all about playing the long game with them. What I've realized is it’s different to sport.

When you find a 16-year-old athlete, and they wanna go to the Olympics, well you want to be with them for 7 years, right? And a lot of great coaches in sport are with athletes for an extended period of time because you can build on that. I think one thing that I've come to terms with as I've learned more about this coaching space is that it’s not gonna be true in startups ever. 

Investors stay around, but I think it's actually healthy for advisors and coaches to sub in and out at certain stages. It helps the founder stay fresh. And so I'm learning this, and I think one of my successes is learning that. 

We're building some technology now to take this to a whole new level so we can replicate my coaching style without me being there. And founders can control growth with a performance dashboard exactly like an athlete would when their data downloads from their wearables. 

There's a lot of small wins we've had, but I'm doing this for the rest of my life, so I feel like we're just getting started at Hillspeed Group.

[01:05:30] Jennifer: That's great. So you have your own scaling challenges, and you can build another software company around that. How do you think you have evolved over the years personally?

[01:05:39] Coach: I think I got sucked into the Silicon Valley way of building businesses. I still love a lot of the elements of that, the disruptive nature of bringing ideas into the world and making them commercial. 

But I think one thing that's always been inside me, which I didn't acknowledge enough when I was a founder, was I like caring for people. I want people to be better off. I like business as a vehicle to help people. But when I found myself in the founder role, I looked at the market as opportunity, not as people, and that wore me down. 

So I guess the more I build my career in the world of business, I'm really just eager to make the journey exciting on a people level. If I can be more human to them, maybe they can be more human with their businesses. And then hopefully the next 10 years of companies, we'll be emotionally more mature. 

And look, if there's one thing that I just feel really excited about, it's the fact that we have more female leaders coming through. Man, I just obsess over working under females. I think that the greatest leaders on the planet because they're predictable, you know what is expected of you generally. And I'm talking about the female, feminine style of leadership - I don't wanna generalize too much. But there are new types of leaders, and we've got more diverse minds coming into the workforce than what we had certainly 20 years ago.

So I think we need to make sure that these businesses that they're creating are fundamentally different. And so I'm enjoying this space to explore that with people as this tall, privileged white guy. Sometimes I feel like I shouldn't be here, but at the end of the day, well, I've been given the chance to do that. So I'll support as many people who need support because I've got the tools and resources to do that. 

[01:07:34] Jennifer: And to those struggling entrepreneurs out there who may be listening, what is your best advice to them?

[01:07:41] Coach: Don't give up, just keep going. It's all a journey, and the journey changes, but just don't give up on yourself. You will look back in five years and think whatever problem that you've got now, it will really feel insignificant. 

And I don't know how you feel Jennifer, but I feel the most satisfaction looking back at my life, at the things that were hard, not just in business. So yeah, startups are rewarding in that you do feel like you've lived a good life or you've given your all. So don't give up. 

[01:08:14] Jennifer: Absolutely. Now I look at all the stress that I put myself under five years ago, they came from me, didn't come from anyone else, I put myself under that stress. So, they do seem quite insignificant. 

So whenever I talk to founders, I always tell them not to be so hard on themselves and even if they're gonna fold the company. So to this guy, I basically told him if you have to fold the company, then close it down, but don't let it define you because you will encounter many failures in life and this is not the only thing. And I hope that that's not going to define him. 

What do you hope to accomplish in the next 10 years?

[01:08:52] Coach: To make a difference in the way we coach people in business. And what I mean by that is I don't want it to be about me, I want to create a set of frameworks and tools that can help others be their version of a coach. And I'm hoping other people will do that too. So I want coaching to become more valuable in business like it is in sport. That's what I'm committed to.

[01:09:15] Jennifer: And who's your favorite coach?

[01:09:17] Coach: My wife, (chuckles) my wife is my favorite coach. She's the one that made me realize that the next generation of coaches aren't people who are defined by coaches. And if we can unlock these people, the people who believe in the people around them and have skill sets to just keep them moving forward, holy shit. Business is gonna be incredible.

Another favorite coach, my coach, Benjamin J. Harvey, I think is one of the most phenomenal humans on the planet. Not only does he know coaching across all different disciplines, his story is nuts. So yeah, I tend to hang around him a lot because it makes me a better coach. 

I think that a coach creates a space for the athlete to be their best self. Now the parts of sport where I get really excited is if you go to the little league on a Saturday, you go to the local park and you see all the kids. Those coaches are phenomenal because they're creating a space for those kids to just be their best self.

And it is no different at the professional level and the junior level as a coach, it's always about creating space for the individual. 

[01:10:27] Jennifer: It's about creating that space for the individual to flourish, to be the best version of themselves, absolutely. 

Tell us what your favorite books are over the years.       

[01:10:41] Coach: Books are a funny tool in life. They're definitely where you find out parts of the world that you didn't understand. And so they're your gateway to just developing as a human, but they're important or influential in your life, at different times. So there's two defining books for me.

The first one was Think and Grow Rich, which is just a classic personal development book by Napoleon Hill. I read that at a right time when I was working in retail. And that helped me envision the world of business like I did as an athlete. You've gotta be able to see the play as an athlete and see the game the way that you want to create. That book allowed me to just go, wow, that principle applies in business too. 

Then when I crashed my company 10 years later, I had been given a book a couple of years earlier by Jocko Willink called Extreme Ownership. And it sat at my bedside table and basically the day that I announced my company, it was over. I picked up that book and it helped me handle the stress as a founder because I really just wanted to blame the world. I wanted to blame everything, I just couldn't believe that I failed. And that book helped me take extreme ownership for keeping going as a leader, not letting the startup define me. 

I really like those two books, but they would only be meaningful to somebody else if they're at the right time.

[01:12:04] Jennifer: And where can people find you and Hillspeed Group online? 

[01:12:08] Coach: Yeah, Just go to Or just follow me on Instagram or Twitter. I'm coach_leighroy, and don't be afraid to reach out and say, hi, I'm a human. I love to connect with people. And, if you're a founder and you are building something and that thing's important to you and I would love to chat to you about coaching. 

[01:12:30] Jennifer: Last but not least, what does the Founder Spirit mean to you?

[01:12:33] Coach: It means commitment.

[01:12:35] Jennifer: Seeing it through.

We're now coming to the end of our interview, and as you know, we end every episode with a quote, and for this episode we have a quote from Phil Jackson, a former professional basketball player and coach of the Chicago Bulls: 

“You can't force your will on people. If you want them to act differently, you need to inspire them to change themselves.”

Coach Leighroy, I wanted to thank you very much for being very open about your journey and sharing with us your mission to create more resilient founders and more sustainable companies in the long run. Thank you so much.

[01:13:12] Coach: Thanks, Jennifer. 

You can find us on Apple, Spotify and Google Podcasts, as well as our website at

[01:13:24] END OF AUDIO

Show Notes

(02:28) Coach Leighroy’s Journey as an Elite Triathlete

(06:34) When did Leigh Decide to Become a Coach?

(10:19) Things He learned in Holding Odd Jobs

(11:27) Transition from Peak Performance Sport to Tech Entrepreneurship 

(12:48) The Importance of Fundraising and Name Recognition for startups

(18:35) Challenges at PantreeCo

(23:21) Everything You Need To Know About Business Accelerators

(30:20) Closing Down PantreeCo

(34:16) Why Do Burnouts Happen and How To Avoid Them?

(40:21) The Creation of Hillspeed Group

(46:00) Business Problem versus Human Problem

(51:00) Foundations to Scale

(59:00) Common Mistakes Made by Startup Founders 

(62:13) Differentiating Himself in the Startup Ecosystem 

(66:37) Coach's Advice to Struggling Entrepreneurs

(71:29) What the Founder Spirit Means to Coach

Social Media Links:


LinkedIn: Coach Leighroy

Instagram:  Coach Leighroy

Twitter: Coach Leighroy

Coach’s Favorite Books:

- Think and Grow Rich, by Napoleon Hill

- Extreme Ownership: How U.S. Navy SEALs Lead and Win, by Jocko Willink and Leif Babin

- Beyond Possible, by Nimsdai Purja

- Breaking The Habit Of Yourself, by Dr. Joe Dispenza

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