🧠 Founders, Play Your Own Game

Hi. Hello. Hello. 👋

Today’s guest is a dear friend, a repeat podcast guest, and someone I respect enormously for his deep thinking and straight talk: Brice Scheschuk.

If you know Brice, you already know he’s built, scaled, exited, and reinvested with wisdom. If you don’t, here’s the gist: he’s an operator turned investor with a rare lens—130 direct startup investments, 50+ VC fund LP positions, and most importantly, no one to please but the truth.

We ran into each other recently over drinks, and Brice shared his latest keynote: "Founders, Play Your Own Game."
It’s part tough love, part strategic blueprint. And it resonated with me on every level. You can find the link to his presentation here.

Here’s what we explored—and why every founder, funder, and advisor in the innovation ecosystem should read this.

🚨 The Most Consequential—and Irreversible—Decision a Founder Makes

Brice calls it out plainly: raising capital is not just a milestone—it’s a turning point.

Once you take money, especially VC money, you commit to a set of expectations that can change your culture, control, governance, and trajectory. The math changes. The growth expectations accelerate. The room for error shrinks.

My take: “It’s like a favor with the mafia. Once you’ve shaken that hand, you’re in the game.” ;-)

His core argument? Most founders don’t understand the rules of the game they’re entering. And worse, the ecosystem’s conventional wisdom makes it sound like VC is the only game in town.

📉 The VC Narrative: High Valuation, High Velocity… High Risk

Brice breaks down the past decade of venture into three chapters:

  • 2016–2019: Risk-on boom and valuation creep

  • 2020–2021: Pandemic stimulus, zero rates, digital hype—and a bubble that rivals Dotcom 1.0

  • 2022–today: Reality check, capital contraction, and now… the AI frenzy

Most companies that raised big during the hype years are now struggling, gone, or playing catch-up. The capital created a treadmill they weren’t ready to run.

“99.9% of the oxygen in the ecosystem is about why to raise VC. But 99.9% of companies shouldn’t raise it.”

Oof. Let that sink in.

Share

🧭 Raising Capital (or Not) Is a Strategic Identity Question

So how do you know if raising capital is right for you?

Brice’s checklist is as nuanced as it is practical:

✅ Do you deeply understand your market, product, customer, and go-to-market math?
✅ Are you building something truly venture-scale—or just using the wrong financing for your actual growth model?
✅ Are you ready to lose some control to gain some capital?
✅ And most importantly: Who are you building for—and what kind of entrepreneur do you want to be?

He uses Shopify’s Tobi Lütke as a model: six years of patient exploration, only $1M raised, and a culture defined before VC ever entered the picture.

Contrast that with the standard: Demo Day, deck, $3M on $30M valuation, little customer insight, and a power-law investor expecting a billion-dollar exit. That’s a mismatch—and a slow-motion car crash.

🧠 Invert, Always Invert: The Power of Counter-Narratives

Brice is a fan of Charlie Munger, and his advice follows Munger’s “inversion” principle: figure out where failure lives and avoid it.

That means:

  • Model your business as if you had to bootstrap it.

  • Build in plateaus. Assume the hype fades.

  • Explore non-dilutive capital: consulting, grants, debt (when rational).

  • Cut the clutter. Funded startups often spend because they have to, not because it makes sense.

In short: raise less, learn more, grow cleaner.

🧘‍♂️ Mindset Wins: Entrepreneurial Resilience Isn’t Optional

Brice also teaches a workshop on entrepreneurial resilience, rooted in 100+ expert interviews and years of observing founders under pressure. He breaks resilience down into:

  • Personal: self-awareness, stress recovery, habits

  • Team: decision hygiene, communication, cognitive load

  • Organizational: governance, culture, structure that supports—not drains

“The 81st hour of the week might be better spent outside your business. It could save your next 80.”

This isn’t fluff. It’s a corrective to hustle culture, which has done real psychological and financial damage to founders.

Share

🔁 Conventional Wisdom? Strike It Out.

Brice’s final mic drop?

He wears a T-shirt that says:
“Conventional Wisdom” (with a red strike-through).

Everything you’ve been told—do the accelerator, avoid services revenue, raise fast and big—deserves a second look. The better path? One that fits your business, your goals, and your life.

Subscribed

🧩 Takeaways for Founders (and Funders)

  1. VC is a tool, not a destiny. Use it if and when it fits. Not before.

  2. Founders must own their financing strategy. Don’t abdicate to what’s fashionable.

  3. Building lean is not a bug—it’s a Canadian superpower.

  4. Control is underrated. Dilution is forever.

  5. The right capital, at the right time, for the right reasons. That’s the game.

And that’s the message we need to amplify across the Canadian tech ecosystem.

Share

Thanks again to Brice Scheschuk for bringing such clarity, candor, and courage to this conversation.

🎤 We'll definitely have him back in the fall—for a deep dive into resilience and the founder psyche.

Until then: Play your own game.

Peggy Van de Plassche is a seasoned advisor with over 20 years of experience in financial services, healthcare, and technology. She specializes in guiding boards and C-suite executives through transformational change, leveraging technology and capital allocation to drive growth and innovation. A founding board member of Invest in Canada, Peggy also brings unique expertise in navigating complex issues and fostering public-private partnerships—key elements in shaping the Future of Business. Her skill set includes strategic leadership, capital allocation, transaction advisory, technology integration, and governance. Notable clients include BMO, CI Financial, HOOPP, OMERS, GreenShield Canada, Nicola Wealth, and Power Financial. For more information, visit peggyvandeplassche.com.

peggy vandeplassche