Ironman Triathlon to Raising Funds for Toronto’s Homeless

Ironman Triathlon to Raising Funds for Toronto’s Homeless

From the Road to the Cause: How Jake Shipman Is Turning His Ironman Journey Into a Mission for Good.

Training for an Ironman triathlon isn’t just about physical endurance; it’s about mindset, motivation, and sometimes a deeper sense of purpose. For Toronto resident Jake Shipman, that purpose is supporting his community through a meaningful cause. This year, as he trains for a 70.3 Ironman, Jake is using his athletic journey to raise funds for Homes First!

In this candid conversation, Jake shares what pushed him to take on the challenge of an Ironman race, why he chose to support Homes First, and what keeps him going day after day.


Q&A with Jake Shipman

Q: What inspired you to take on the incredible challenge of an Ironman triathlon?
Jake: I started to get serious about running in my adult life, competing in a few races a year. I’ve always been very competitive with myself, so it became more than just a hobby. I was constantly upping the ante: longer races, beating my times, striving to be in the top percentile, etc. 

Eventually, I wanted to challenge myself in a new way mentally and physically by doing triathlons. I wasn’t actively biking or swimming, but I knew how to do these things, so it was just a means of getting the right equipment and getting to work. 

I participated in my first ever triathlon, an Olympic distance Ironman event, in Quebec about three years ago. Despite challenging moments like unintentionally swallowing lake water (classic) and having muscle cramps towards the end of the race, I was totally hooked after this experience. Just as with running, any improvement in my performance has been met with my ever-growing ambitions.  

Q: Why did you choose to support Homes First through your Ironman training?
Jake: I’ve been living in Toronto for the last ten years, and homelessness has always been a pervasive issue, but it’s become even more visible since the pandemic. By the numbers, I was shocked to learn there are as many as 12,000 people homeless on any given day. And I see it for myself in my own neighbourhood and across the city, whether I’m walking my dog or out training.  

Often it looks like these folks are just your average person who may be living on the edge and just needs a helping hand to get back on track. It just doesn’t seem right, especially for a place like Canada, so it was time step up and do something about it. 

I discovered Homes First by Googling different organizations in Toronto that were addressing homelessness. I wanted to understand who was making a real impact. I came across a Reddit thread where someone laid out the case for Homes First, and I loved the holistic approach that Homes First takes getting people into stable housing, providing meals, mental health support, employment help. It all just resonated with me. It felt meaningful and legitimate. So the rest is history. 

Q: When you think about the thousands of people experiencing homelessness in Toronto, what goes through your mind? And what do you hope the future holds for them?
Jake: It feels like there’s a duty to help but I’ve often felt powerless, like I alone can’t make a difference. I was fortunate to visit Sydney, Australia recently, a city of similar size, which to my surprise, has almost no homeless population. This was a real ah-ha for me to realize this issue isn’t insurmountable – it’s solvable. And discovering Homes First has honestly provided me a renewed sense of hope and agency about making an impact.  

What do I hope the future looks like? I’d love to walk through the streets of Toronto and not see people unhoused anymore, to know that we live in a city where everyone has access to stable housing. That’s what I want. 

Q: Training for an Ironman is no small feat. What does your preparation look like, and how do you stay motivated?
Jake: A big part of it is having goals. Signing up for the race is a good start and even getting more specific. For me, I want to complete this upcoming race in under five hours and possibly even crack the top 10 in my age group. 

Being disciplined has been essential. Having a structured plan that tells me what I’m doing each day, like a 60-minute bike ride followed by a 30-minute run, which makes all the difference when you’re juggling three different disciplines: swimming, biking, and running. It also has to fit around everything else in life like work, relationships, and other passions. 

Nutrition is a big piece of that planning too. I try to be very intentional about how I fuel myself: 

  • Pre-activity is mostly carbs, low in fibre and fat. 
  • During training, it’s still carbs and electrolytes to replace what I’m sweating out. 
  • Post-activity is mostly protein to repair muscles, plus getting back to the basics like vegetables. 

While my motivation mostly comes from my competitive nature when I set a goal, there are other intrinsic rewards. For instance, I love sharing the experience with others, like my speedy wife who I often run with or my friend who’s also taking part in this race.  

I also find endurance sports highly therapeutic. When out in the sun, working hard, you’re not thinking about work or what’s on TV, you’re just thinking about your next breath. Training also opens you up to new experiences – you find hidden gems like a cool coffee shop on a bike ride or you connect with others on a similar journey. And the best part is, you can do it almost anywhere. One of my favourite things to do when I’m travelling is to bust out my running shoes or find the local watering hole.   

The only thing missing has been a sense of shared purpose, so tying this into Homes First’s cause will make this even more rewarding. 

Q: What would you say to others who are thinking about using their passions, athletic or otherwise, to support a cause they care about?
Jake: Just do it. Honestly, I could even kick myself in the pants for not starting sooner. I’ve been thinking about doing something like this, fundraising around my personal passions, for a couple of years now. 

It just took time to do the work of actually finding an organization and a cause that I felt equally passionate about. But once I did, I took the plunge and started fundraising. And now I keep thinking, “Man, I wish I had done this earlier.” Maybe instead of raising my first thousand dollars, I’d be at ten or twenty thousand by now, which is a really cool thing to think about. 

But at the same time, that’s what will motivate me to keep doing this kind of thing going forward. 

I think a lot of people probably feel that sense of fear, like what if only a few people donate. But that’s okay. In charitable work, it’s so true that every dollar counts. Even raising awareness makes a difference. 


Want to support Jake’s Ironman fundraiser for Homes First?
Visit https://homesfirst.on.ca/jakes-fundraiser/ to donate and follow his journey. Every contribution helps and shows that homelessness is not an insurmountable challenge.

To learn more about the Ironman 70.3 Triathlon visit https://www.ironman.com/

Other Stories