Fountain 50
It is Ria’s week here at The Fountain, and I wanted to set the stage for her piece with an idea that has shaped both of our lives - and might help inspire your 2026 goals.
Every major step forward in my life and career came from entering a new environment that forced me to level up.
And whenever Ria and I talk to younger founders, we keep coming back to the same truth. The people who put themselves where the action is, are often luckier.
This edition is about that idea. About using your environment as a lever for growth. About how the choices you make in your twenties and thirties quietly build the foundation for the decades that follow.
And about how opportunity shows up when you move toward it.
If you know anyone looking to shake things up or who this topic might benefit, we hope you share this - in the spirit of that Fountain energy!
Let’s get into it.
⏳️ Estimated Read Time: 6 minutes
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Leadership and Personal Growth
Stacking Decades
My inspiration for this topic started with a simple reflection I had recently:
What you do in your twenties quietly builds the foundation for your thirties. What you do in your thirties sets up your forties.
This isn’t about being “career focused”, it’s that where you put yourself will reflect in the richness of your skillset, network and confidence. In any era, consider:
Traveling or backpacking
Learning a language
Taking courses or lessons
Volunteering
Taking strange or entry level jobs
Saying yes to big and small adventures
Taking on brave challenges embeds skills and perspectives you will draw on for the rest of your life.
Some of the most visionary versions of ourselves lives in our twenties. At that age, we strike an intersection of ability and courage, risk appetite and having nothing to lose (also, we are willing to live on a friend’s couch or eat simple meals to make our dreams come true).
Thinking back on our life, I can see that we are still leveraging the lessons and track record we earned at SAXX and for many people, their most visionary endeavours are during this special period:
Jeff Bezos was at his best in his garage - scrappy and committed to a vision that few people understood;
Mark Zuckerberg was peaking at 19 when he was on campus trying to actualize the power of digital connections amongst peers;
Oprah Winfery’s life began a world-altering trajectory when she moved to Baltimore to host her first TV Chat show “People are Talking”
It’s a Big World After All
When Trent and I talk to younger founders, we often come back to the same idea:
Go where it is happening.
If you are trying to start a business, break into an industry, or level up and it feels like you are running in sand, sometimes the problem is not you. It is your environment. I mean, you can achieve success from almost anywhere these days but your luck is likely better when you put yourself in physcial proximity to your goals (live closer to a gym, plant your garden closer to your house, be around the people you want to learn from).
There are pockets in the world where cool things are happening all the time. Some are obvious, like New York or Hong Kong. Some are tiny and almost secret. Here in California, there is a little town near us called El Segundo. It looks unassuming, but the types of companies setting up shop there has really made it a hub for deep tech and aerospace.
There are versions of that everywhere.
If you have the ability in your twenties or early thirties to visit or move to a place where your goals match the ecosystem, the odds of your goals being achieved goes up exponentially.
You are not guaranteed anything, but your surface area for opportunity multiplies.
We did this with SAXX when we moved to Vancouver. We did it again moving to Los Angeles. Each time, it was uncomfortable and uncertain, but it expanded what we saw as possible.
The Amazon, Bugs, and Becoming Yourself
Trent and I both backpacked on a shoestring budget before we met each other; it helped form and inform our values today.
On one of my adventures, I volunteered at a biological reserve in Ecuador called Hatun Sacha. It was full of bugs, scorpions, tarantulas, and snakes. What I learned was that nature is not out to get us. It is a kind of living harmony. I also learned that the most memorable rewards are earned in discomfort, specifically getting up early to walk through the dark jungle, climb a crazy high tree and enjoy the sunrise above the canopy. Totally scary, totally worth it.

Blurry and tired above the Amazon canopy 🙌🏼
Change can Start Small
It certainly doesn’t have to be the Amazon.
It’s natural to feel a desire for something new, something more, and to break away from the “tribe” - and that feeling can come from smaller changes too:
Go to a new space regularly: a new church, a pottery studio, a community choir, a co-working space
Experiment: say yes to things that you naturally resist, be okay with looking silly, spend time with yourself and without a screen to discover what really lights you up
Learn a skill that forces you into a new community: an instrument, a new sport, a language class
Take a hike or visit a nearby city, town or park that you’ve never checked out
The point is not drama. It is expansion. New people. New perspectives. The belief that you are undefinable and always evolving.
From Twenties to Thirties to Forties
When I look back, my twenties were full of seeds: business degree, backpacking, jobs in hospitality and retail, yoga teaching, meeting Trent and building SAXX.

Yoga Teacher Training in Maharashtra, India - 2008
The year we sold SAXX, I turned 30.
Confidence, Self Reliance, and Seeing People Clearly
The biggest mindset shift from that decade, for me, was confidence. Not the loud type. The quiet kind that says, “I can handle things.”
A few things helped build it:
Doing big things alone like traveling solo.
Volunteering and working entry level jobs in hospitality and retail
Understanding that everyone is human and equal, no matter their status
When you expose yourself to very different lives, your sense of hierarchy starts to dissolve. You see people more clearly. That empathy becomes a superpower in business.
It helps in sales and negotiation. If you can understand what motivates someone, what they fear, and what a win looks like for them, you naturally become better at doing deals where everyone can live with the outcome.
Self reliance plays into this. As Trent often says, the moment you stop being dependent on others financially, your confidence jumps. Self reliance equals self confidence.
Go Where It Is Happening, Even If You Do Not Know The Path
One of the quieter lessons from backpacking was this: You do not always know the exact path. You just need to know the direction.
On my trip, I always knew the broad route. But I did not always know which cities I would stay in or for how long. I stayed open to recommendations and unexpected invitations.

That is how I met Trent. Neither of us were looking for each other. But I knew the direction I wanted my for my life. When someone showed up who was building something interesting, who I connected deeply with, and who truly believed I could help, it would have been strange to ignore that just because it was not part of my rigid plan. I wanted my MBA - I was lucid enough to realize this unexpected turn was the real deal. A street MBA.
I heard a great analogy recently: It’s like crossing a river. You know you want to get to the other side but you must feel your way, one wiggly rock at a time to pick the right path.
Your Move
If you are in your twenties, early thirties, or looking to make a move - this is your window.
Your brain is always plastic.
Find out where the values-aligned action is. That might mean moving cities. It might mean changing your idea of a vacation. It might mean walking into a different room full of people doing the kind of work you aspire to do.
Regardless of whether you change things up or do the same, your choices will have an impact. Slow and steady really does win the race, and even the small chances we take in life help build a rich and interesting tapestry that you can be proud of.


Q&A with League of Innovators Accelerator (PART 2)
LOI is Canada’s biggest accelerator for founders under 30. I speak with their newest cohort every year, here were some of their best questions.

Q: How did SAAX’s brand and visuals change over time? What were the steps?
A: Early days: I focused on seeding product with athletes and influencers (baseball, music, Hollywood). PR agencies were key to getting attention. Packaging and branding were made to fit the “stream” (retail standards) to facilitate in-store adoption, but I still aimed for strong distinction. I targeted international expansion early, adding website localization and distributors. I paid attention to making visual design clean, simple, and effective—don’t overload packaging, keep key info legible.
Q: What do you say when people ask, “Why won’t a big company copy you?” How do you defend your differentiator?
A: It’s all about speed and agility—being the “pirate ship” that can act quickly and reach niche buyers before large incumbents can react. Big companies may not act because a) reputation, b) being busy with bigger revenue, or c) waiting for innovation to prove out. Get on their radar as an acquisition target by building traction and building relationships at potential acquirers.
Fountain Community Progress
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What else we’re paying attention to in the finance world:
Bitcoin plunged after a wave of liquidations, with over $1 billion of positions wiped out in a single day. The speculation is really about investors moving towards “safer” investments like gold and bonds.
Berkshire Hathaway revealed a new ballot of nearly $4.3 billion in Alphabet shares, moving into tech more boldly than usual. The move suggests another company giant sees long-term value in Alphabet’s positioning.
SKIMS raised $225 million, boosting its valuation to $5 billion as the brand expands globally and into product categories beyond shapewear, crazy.



