Join your host, Matt Cohen, Founder & Managing Partner at Ripple Ventures for weekly conversations with leaders in the startup ecosystem discussing the truth about investing, building and running startups.
How Biossil is Rescuing Billion-Dollar Drugs Big Pharma Abandoned | Anthony Mouchantaf
Épisode 340
jeudi 17 septembre 2026 • Durée 58:42
In this episode of Tank Talks, host Matt Cohen sits down with Anthony Mouchantaf, co-founder and CEO of Biossil, a biotech company on a mission to resurrect orphaned drugs using AI and a hedge fund–inspired operating model. Anthony takes us through his unconventional journey: from a law school student obsessed with Alexander Hamilton, to founding his first startup, Rthm (acquired), to investing at OMERS and RBC, and finally returning to the founder seat with Biossil.
They dive into the mindset shift required to leave a stable legal career for the uncertainty of startups, why Anthony views entrepreneurship as a “drug,” and how his time as an LP shaped his view of what separates great VCs from mediocre ones. Anthony opens up about the early days of Biossil, the “too cute” capital-efficient strategy, and how a serendipitous dinner intro to Founders Fund changed everything.
He also breaks down the real-world mechanics of acquiring off-the-shelf drugs, the brutal reality of biotech timelines, and why regulatory reform is the hidden bottleneck to AI-driven medicine. From the partnership with OpenAI to the company’s operating philosophy (hedging beta, maximizing catalyst density, and isolating alpha), Anthony offers a blueprint for building a resilient, mission-driven biotech for the AI era.
Whether you’re a founder, investor, or just someone curious about the intersection of AI and life sciences, this episode is packed with hard-earned wisdom on risk, identity, and the art of controlling what you can control.
From Law School to Startup Life (02:24)
* Growing up in Toronto as the child of immigrant parents, chasing constitutional law
* The Alexander Hamilton obsession that started in high school
* Teaching a course at U of T law without ever practicing
* How a late-night conversation at Massey College with co-founder Alex led to Rthm
What Founding Rthm Taught Him About Himself (06:14)
* Getting comfortable with structural uncertainty as almost “a drug”
* Why you can take the individual out of the startup, but never the startup out of the individual
* The itch that never fully goes away after founding something
From Founder to Investor: OMERS and RBCX (07:11)
* What separates great investors from destructive ones
* “Extremely hard to kill”: what he saw early in Matt and Ripple Ventures
* Why most VCs cluster around mediocrity, and what the outliers do differently
* The poker-chip analogy: how capital position shapes VC risk appetite
* Why good LPs need to “thumb the scale” for good VCs, just as good VCs do for founders
The Idea Behind Biossil (15:05)
* Reuniting with Alex, an MD-PhD, after years on separate paths
* The core problem: drug development should be recursive, but biotechs can’t afford to make it so
* Why promising drugs get stranded in “regulatory limbo” when the data is equivocal, not failed
* The insight: using technology to systematize what was historically a relationship-driven, human-scale rescue effort
Biossil 1.0 vs. the Bigger Vision (20:43)
* Launching in 2023 on a lean seed round with no capital to acquire drugs outright
* Getting “too cute” trying to solve the problem at a fraction of the necessary cost
* Why most VCs evaluate founders cross-sectionally instead of longitudinally
Hunting for Orphaned Drugs (26:03)
* Why data is a cost of admission in biotech, not a moat like in tech
* How Biossil structures deals to share economics with original rights holders
* Why inbound interest rarely meets their bar
Running Biossil Like an Operating Hedge Fund (30:50)
* Isolating alpha, or execution, from beta, or market and biotech cycle risk
* Why traditional biotech investing is “binary risk you can’t underwrite” without a portfolio
* Building resilience through catalyst density instead of just runway
* The “epsilon” factor: surviving long enough for unexplained outcomes to work in your favor
Building Lean with AI (34:12)
* Running a hyper-efficient, eight-person core team
* Why Biossil takes on regulatory and commercial risk, not manufacturing risk
* The pipeline today: $70M raised, 11 drugs, 5 open clinical trials across the US, Canada, and Europe
* What makes manufacturing the most underestimated cost in biotech
The Next 5-10 Years for Biossil (49:47)
* The long-term vision: an approved-drug pipeline, deeper trials, more disease areas
* Bringing new mechanisms of action to market as a category-defining goal
Advice to His Past Self (51:15)
* Why he’s hesitant to just tell people to “go do entrepreneurship”
* Motivation matters more than the identity of being a founder
* The Steve Jobs commencement speech that reframed how he thinks about risk
About Anthony Mouchantaf
Anthony Mouchantaf is the co-founder and CEO of Biossil, a biotech company that uses AI to systematically identify, acquire, and advance orphaned drugs left behind by failed clinical trials. With a background in law (U of T), startup founding (Rthm, acquired), and venture investing (OMERS, RBC), Anthony brings a rare blend of legal, financial, and operational discipline to the high-stakes world of drug development. Biossil is backed by Founders Fund and OpenAI, and is on a mission to turn industrial-scale drug resurrection into a new category of biotech innovation.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit tanktalks.substack.com
The Rundown 9/14/26: Canada-U.S. Trade Talks Collapse, Anthropic’s AI War, and Miro’s $16B Fall
Épisode 339
lundi 14 septembre 2026 • Durée 23:35
Matt Cohen and John Ruffolo break down the collapse of Canada-U.S. trade negotiations, the unanswered questions surrounding the failed deal, and whether Canada is protecting legacy industries at the expense of technology and long-term economic growth.
They also examine Prime Minister Mark Carney’s ambitious pitch to bring international capital back to Canada, including billions of dollars in proposed energy, transportation, infrastructure, and technology projects. But can a polished deal book convince investors to fund projects that have struggled to attract capital for years?
Finally, Matt and John unpack the political battle forming around Anthropic’s anticipated IPO, the growing influence of AI regulation campaigns, and Miro’s dramatic fall from a $17.5 billion valuation.
As Canada searches for a way out of its trade crisis, global investors are being asked to reconsider the country’s economic potential. At the same time, AI companies are entering a political and regulatory battle that could determine who controls the industry’s future.
If you are a founder, investor, policymaker, or anyone trying to understand where capital and technology are heading next, this episode is worth your time.
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A big thanks to our sponsor, Moomoo Canada
This is the kind of tooling that used to live on a Bloomberg terminal, but now it is on your phone, just a few taps away. They offer real-time data, full options chains, and an AI assistant that actually explains trading strategies.
Moomoo is the perfect place for people who want to take their money seriously. Open an account today at moomoo.ca
Why Canada-U.S. Trade Talks Fell Apart (01:31)
The latest Canada-U.S. trade negotiations appeared close to producing an agreement until everything suddenly unraveled. John argues that the biggest problem is not simply the failed deal, but the Canadian government’s refusal to clearly define what success was supposed to look like.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit
How Rock Bottom Turned Chris Pronger Into an NHL Legend
Épisode 338
jeudi 10 septembre 2026 • Durée 59:18
In this episode of Tank Talks, host Matt Cohen sits down with Chris Pronger, Hockey Hall of Famer, Norris and Hart Trophy winner, Stanley Cup champion, two-time Olympic gold medalist, and one of the NHL’s 100 greatest players. Chris takes us inside the mindset that transformed him from a booed 21-year-old in St. Louis into one of the most dominant defensemen of his generation.
They break down what it really takes to bet on yourself, why delayed gratification is the secret to sustained excellence, and how Chris rebuilt his entire training protocol from the studs after already being nominated for a Norris Trophy. Chris opens up about the early-career failures that forced him to look in the mirror, the veterans who shaped him, from Brad McCrimmon to Wayne Gretzky and Al MacInnis, and the 4-pound muscle between his ears that changed everything.
He also shares hard-won lessons on leadership, managing teammates with different personalities, the importance of culture in championship runs, and why the best leaders lead by example, not just by talking. From the 2007 Stanley Cup run with Anaheim to the scary commotio cordis incident in 1998 and the eye injury that ultimately ended his career, Chris delivers a raw, unfiltered look at the true cost of greatness.
Whether you’re an athlete, a founder, a leader, or simply someone trying to earn your way forward, Chris offers practical wisdom on resilience, identity, and the art of controlling what you can control.
A big thanks to our sponsor, Moomoo Canada
This is the kind of tooling that used to live on a Bloomberg terminal, but now it is on your phone, just a few taps away. They offer real-time data, full options chains, and an AI assistant that actually explains trading strategies.
Moomoo is the perfect place for people who want to take their money seriously. Open an account today at moomoo.ca
Why Multi-Sport Athletes Have an Edge (04:33)
* The physical and mental benefits of playing multiple sports
* Proprioception, hand-eye coordination, and learning how to learn
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit
The infrastructure behind the next wave of interactive AI | Keegan McCallum (uRun, ex-Luma AI)
Épisode 337
jeudi 3 septembre 2026 • Durée 52:20
In this episode of Tank Talks, host Matt Cohen sits down with Keegan McCallum, co-founder and CEO of uRUN, an inference provider built for persistent, steerable, interactive AI experiences. Keegan’s path took him from jailbreaking iPods in Thunder Bay, Ontario, to building the infrastructure that powered Luma AI’s viral Dream Machine launch, scaling from 500 to 9,000 H100s in six hours to process over half a million videos.
They break down why the industry is wrong to shoehorn interactive AI into old request-response systems and why the future belongs to persistent, stateful, real-time experiences. Keegan explains the technical differences between LLMs and video models, why infrastructure is the biggest bottleneck for the next wave of AI, and what it takes to recruit top engineering talent.
He also shares hard-won lessons on selling to developers, the Canadian AI talent landscape, and his bold, contrary views on the AI supply chain. From avatars and steerable video to coding agents generating 1,000 tokens per second, this episode is packed with frontline insights.
Whether you are a founder building in AI, an infrastructure engineer, or simply curious about where human-computer interaction is headed, Keegan delivers a clear-eyed look at the future of interactive AI.
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A big thanks to our sponsor, Moomoo Canada
This is the kind of tooling that used to live on a Bloomberg terminal, but now it is on your phone, just a few taps away. They offer real-time data, full options chains, and an AI assistant that actually explains trading strategies.
Moomoo is the perfect place for people who want to take their money seriously. Open an account today at moomoo.ca
The Luma AI Experience: From 500 to 9,000 H100s (04:18)
* Joining Luma after building an early LLM infrastructure startup
* The Sora demo and the pitch to build and release a competing video model
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit
The Rundown 8/24/26: Canada’s Hidden Leverage in America’s AI Race
Épisode 336
lundi 24 août 2026 • Durée 23:41
Canada is back at the negotiating table with the U.S., looking for relief from tariffs on autos, steel, aluminum, forestry, and other goods. Matt Cohen and John Ruffolo break down the latest developments, including the possibility of a revived Keystone XL project and the concessions Canada may have to make to get a deal across the line.
But John’s bigger concern is what Canada could give up in the process. He argues that digital services and technology are becoming the new economic battleground, and Canada risks protecting traditional industries while giving away ground in the sectors that could drive future growth. Matt and John also question why Canada is negotiating from a fragmented position while the U.S. approaches the talks as a unified front.
The episode delves into Ontario’s new rules for AI data centers, the growing debate over who should pay for the massive infrastructure needed to power AI, and Anthropic’s unusual founder-control structure ahead of a potential IPO. Matt and John also look at Stripe’s decision to remain private while making a major AI acquisition, Clearco’s unexpected comeback after securing new financing, and why Canada may be falling behind the U.S. on blockchain despite having some of the strongest talent in the space.
If you want a sharper read on where the U.S.-Canada trade, AI infrastructure, and digital sovereignty are heading next, this episode is a must-listen.
–
A big thanks to our sponsor, Moomoo Canada
This is the kind of tooling that used to live on a Bloomberg terminal, but now it is on your phone, just a few taps away. They offer real-time data, full options chains, and an AI assistant that actually explains trading strategies.
Moomoo is the perfect place for people who want to take their money seriously. Open an account today at moomoo.ca
Canada’s Trade Gamble (03:05)
John warns Canada may trade digital sovereignty for short-term wins on oil and agriculture, calling it “solidifying the past and giving up the future.” He explains how U.S. statecraft has cleverly undermined Canada’s domestic tech industry through data and content restrictions.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit
What 30 years inside critical infrastructure teaches you about security | Karl Holmqvist, CEO of Lastwall
Épisode 335
vendredi 21 août 2026 • Durée 51:43
In this episode of Tank Talks, host Matt Cohen sits down with Karl Holmqvist, co-founder and CEO of Lastwall, a FedRAMP-certified identity security platform built for the highest-risk use cases. Karl has been deep in cybersecurity since the 1990s, with early experience building critical infrastructure, including Canada’s first high-speed mobile data network, and a recent focus on identity security at the forefront of making systems quantum-resilient. In this conversation, they explore the evolution of Lastwall from early behavioral biometrics and cognitive signals to today’s hybrid post-quantum cryptography.
They also dig into the journey to FedRAMP approval and what it really takes to sell to the hardest customers on the planet, from the DOD’s Innovation Unit to critical infrastructure operators globally. Karl shares his view on why hybrid cryptography is the only responsible path right now, the magnified risk of the AI agent era, and his strongly held belief that when it comes to quantum resiliency, you’re either going to be too early or too late.
Whether you’re a founder navigating a path into regulated markets, a security leader thinking about the agentic AI era, or just curious about what it takes to protect critical infrastructure, Karl delivers a grounded, technical, and occasionally unsettling look at where identity security is headed.
–
A big thanks to our sponsor, Moomoo Canada
This is the kind of tooling that used to live on a Bloomberg terminal, but now it is on your phone, just a few taps away. They offer real-time data, full options chains, and an AI assistant that actually explains trading strategies.
Moomoo is the perfect place for people who want to take their money seriously. Open an account today at moomoo.ca
Growing Up in Dubai During the Gulf War (03:50)
* Karl’s childhood in Dubai as an expat during the Gulf War
* Visiting the USS Nimitz and seeing 5,000 people living on an aircraft carrier
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit
The Rundown 8/13/26: AI’s Infrastructure Problem Is Bigger Than We Think
Épisode 334
jeudi 13 août 2026 • Durée 23:22
Canada’s venture capital market is showing signs of life, but the recovery comes with a catch: more money is flowing into fewer companies. Matt Cohen and John Ruffolo unpack what that means for Canadian founders, why promising tech companies keep getting acquired before they reach scale, and whether Canada is at risk of becoming the world’s R&D shop instead of building lasting global champions.
They also dig into Canada’s $2.3 billion Telesat sovereignty bet, the growing backlash against AI data centers over energy and water use, and Mark Zuckerberg’s push for a more decentralized AI future. John agrees with parts of Zuckerberg’s argument, but questions whether the Meta founder is really the right person to lecture the world about distributing power.
Finally, Matt and John break down Ontario Teachers’ massive SpaceX win and what it could mean for how Canadian pension funds think about venture capital. If you want a sharper read on where Canadian tech, AI infrastructure, venture capital, and economic sovereignty are heading next, this episode is a must-listen.
–
A big thanks to our sponsor, Moomoo Canada
This is the kind of tooling that used to live on a Bloomberg terminal, but now it is on your phone, just a few taps away. They offer real-time data, full options chains, and an AI assistant that actually explains trading strategies.
Moomoo is the perfect place for people who want to take their money seriously. Open an account today at moomoo.ca
Canada’s VC Rebound Comes With a Catch (01:53)
Canadian venture funding is rising, but deal volume keeps falling as more capital concentrates around a smaller group of companies.
John explains why this “flight to quality” could create huge winners while making life much harder for strong startups outside the hottest deals.
Canada’s $2.3B Sovereignty Bet (06:15)
Canada’s major investment in Telesat and secure satellite communications is about much more than competing with Starlink.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit
CRO of Affirm on How “Buy now, pay later” Makes Money
Épisode 333
vendredi 7 août 2026 • Durée 53:19
In this episode of Tank Talks, host Matt Cohen sits down with Wayne Pommen, Chief Revenue Officer at Affirm and founder of PayBright, Canada’s first e-commerce buy now, pay later platform. Wayne shares his unlikely journey from competitive rowing, including the Oxford-Cambridge Boat Race, to a PhD in international relations, Bain Consulting, and private equity at TorQuest, where a failed deal set him on the path to building a fintech unicorn.
Wayne pulls back the curtain on PayBright’s early days, from spinning out a tiny 5-person division called HealthSmart Financial Services to pivoting into e-commerce and landing Casper and Endy as launch partners. He offers a practical breakdown of running a successful M&A process, sharing the dos and don’ts that led to Affirm’s acquisition of PayBright in 2020.
Now a senior executive at a public fintech giant, Wayne reflects on what he’s learned from working alongside Max Levchin, why Affirm refuses to charge late fees or deferred interest, and how AI is transforming everything from underwriting to go-to-market. He also shares his views on agentic commerce, the Canadian consumer credit landscape, and why “don’t quit” is his favorite life lesson.
Whether you’re a founder navigating a pivot, an operator scaling through acquisition, or just curious about the future of payments and AI, Wayne Pommen delivers the kind of straight talk that comes from building and scaling one of Canada’s most successful fintech stories.
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A big thanks to our sponsor, Moomoo Canada
This is the kind of tooling that used to live on a Bloomberg terminal, but now it is on your phone, just a few taps away. They offer real-time data, full options chains, and an AI assistant that actually explains trading strategies.
Moomoo is the perfect place for people who want to take their money seriously. Open an account today at moomoo.ca
From Cambridge to Bain to Private Equity (03:10)
* The Oxford-Cambridge Boat Race, a broken wrist, and a comeback story
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit
The Money Behind Money in VC | Julia Maltby
Épisode 332
jeudi 30 juillet 2026 • Durée 45:36
In this episode of Tank Talks, host Matt Cohen sits down with Julia Maltby, a Principal at Fengate Asset Management who has lived the full venture capital lifecycle. Julia started as the first employee at Plum Alley Investments, ran partnerships at WeWork during its hyper-growth phase, spent over five years rising from Associate to Principal at Flybridge Capital, and even ran her own seed fund, Deco Ventures, before moving to the LP side at Fengate in 2025. Today, she invests in early-stage VC funds and direct opportunities across North America.
Julia offers a brutally honest perspective on what she wishes every emerging manager knew about fundraising. She explains why LPs value process over outputs, why founder references from failed companies are more valuable than those from winners, and how GPs can stop leaving first meetings as a “polite maybe” and start qualifying LPs like a sales funnel. She also pulls back the curtain on LP-to-LP communication (which she says is 10X stronger than GP gossip), shares tactical advice on building data rooms that actually get read, and reveals how Fengate pre-approves co-investments to move at startup speed.
Whether you’re a GP in the middle of a raise, an LP sorting through an endless stack of emerging manager pitches, or just curious what venture looks like from every seat at the table, this episode is for you.
From Liberal Arts to Venture Capital (02:07)
* Julia’s unconventional path from studying architecture and social inequality to becoming one of venture’s most respected emerging investors.
* How a cold LinkedIn message landed her first job in venture capital.
* Why having no finance background became an advantage instead of a limitation.
Learning Venture from the Ground Up (04:13)
* Building crowdfunding platforms and SPVs before venture became mainstream.
* Why early-stage investing means wearing product, operations, and fundraising hats.
* Lessons learned from saying “yes” before knowing exactly how to do the work.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit
Why Software Lost Its Moat and Deep Tech Is Winning with Jacob Jackson of Julian Capital
Épisode 331
jeudi 23 juillet 2026 • Durée 44:44
Everyone Has the Same AI Tools Now. So where’s the Moat?
In this episode of Tank Talks, host Matt Cohen sits down with Jacob Jackson, partner at Julian Capital and founder of Deep Checks. A physicist turned SaaS founder turned deep tech investor, Jacob brings a unique perspective on the shifting landscape of venture capital. He shares his personal journey from developing MRI techniques at UBC to founding MedStack, and why he made the full-circle pivot back to backing companies building real, hard technology.
Jacob offers a frank assessment of the defensibility crisis in software, explains why AI is democratizing superpowers across every industry, and makes the case that deep tech offers faster exits and higher unicorn density than its reputation suggests. He also breaks down how Julian Capital supports founders with growth and go-to-market muscle, and why the team behind the idea matters more than ever in today’s market.
Whether you’re a founder building hardware, an investor looking for the next generation of venture returns, or just trying to understand where technology is headed, Jacob Jackson delivers the kind of straight talk that cuts through the hype.
Why Software’s Moat Is Gone (04:00)
* Jacob’s firsthand experience building MedStack, where Amazon, Google, and Azure built competing products almost overnight
* Why the defensibility crisis in SaaS is making it harder than ever for new companies to get off the ground
* The shift from competing on product to competing on capital and go-to-market
Redefining Deep Tech: What Everyone Gets Wrong (06:44)
* The biggest misconception: that deep tech requires 20-year fund cycles
* How SpaceX-style private market liquidity proves milestone-based exits work
* Why the hottest sector of the year is never where the biggest company gets seeded
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit
With provinces reportedly objecting to parts of the proposed agreement and conflicting stories emerging from both sides, Canadians are left guessing about what happened. John asks the uncomfortable question: Is Canada protecting dairy and other legacy interests while sacrificing its technology economy?
The Real Cost of Walking Away From the U.S. (07:43)
Many Canadians support ending the negotiations, but that support begins to disappear when higher taxes, rising unemployment, and slower economic growth enter the conversation. John warns that Canada cannot reduce its dependence on its largest trading partner without experiencing real financial pain.
That burden will not be shared equally. Older Canadians with homes, pensions, and U.S. investments may be able to absorb the disruption, while younger Canadians already struggling with housing and affordability have much more to lose.
Carney’s Plan to Bring Investment Back to Canada (10:18)
The Canada Investment Summit is presenting more than 160 opportunities across energy, critical minerals, transportation, manufacturing, digital technology, and infrastructure. The goal is to reintroduce Canada to international investors after a decade in which global capital largely looked elsewhere.
John supports the strategy but tempers expectations. The summit may not produce immediate checks, but it could rebuild the relationships Canada needs to finance major projects and reverse its reputation as an undercapitalized market.
Anthropic’s IPO Enters the AI Political War (16:15)
A former Anthropic researcher’s warning about self-improving superintelligence quickly spread across the internet, creating fresh questions about AI safety and the company’s anticipated IPO. Matt examines whether the viral backlash emerged organically or was amplified by politically connected organizations pushing for tighter AI regulation.
John believes there is no neutral position in the AI debate anymore. Competing groups are funding optimistic and catastrophic narratives, turning data centers, employment, regulation, and AI safety into deeply political issues. Despite the controversy, he does not expect the backlash to derail Anthropic’s IPO.
Miro’s Collapse and the Continuing SaaSpocalypse (21:11)
Miro was valued at $17.5 billion at the height of the software boom. Its reported acquisition by Bending Spoons at a fraction of that valuation shows how brutally the market has repriced venture-backed SaaS companies.
Miro remains a substantial business with hundreds of millions in recurring revenue and a strong enterprise customer base. The problem was not the product; it was the inflated valuation and financing structure built around it. John expects more overfunded unicorns to face similar outcomes.
* Why parents are stealing their kids’ childhoods with early specialization
* The truth about peewee superstars: 99 out of 100 aren’t the best at 18
The Veterans Who Shaped a Hall of Famer (07:28)
* Brad McCrimmon as a mentor and “woobie” in Hartford
* Learning consistency, preparation, and professionalism from the ground up
* Walking into a locker room with Gretzky, Hull, MacInnis, and Fuhr
* Watching how the greats handle media, scrutiny, and the grind
Getting Booed, Hitting Rock Bottom, and the Aha Moment (10:33)
* Being traded for Brendan Shanahan and getting booed relentlessly in St. Louis
* The dark hole of not being prepared and the wake-up call that changed everything
* Why Gretzky’s arrival was a blessing that took the spotlight off him
* The summer that launched his ascent: training, preparation, and the 4-pound muscle
The Magical 1999-2000 Season (13:27)
* Winning the Hart and Norris in the same year, first defenseman since Bobby Orr
* Staying healthy through proper training and offseason dedication
* How Al MacInnis’ injury forced him to carry more weight
* The magical regular season that fell apart in the playoffs
Delayed Gratification and the 2007 Stanley Cup Win (16:15)
* Compounding summers of training with Charles Poliquin
* Scrapping his entire training protocol after a Norris nomination
* Getting twice as strong in one summer and feeling the difference on the ice
* Winning the Cup with Anaheim, and why the mission was winning for everyone else
Outlasting Opponents and Battling Peter Forsberg (19:46)
* Taking pride in being the best-conditioned athlete on the ice
* The battle of attrition and grinding guys down
* Why Forsberg was one of the toughest players he ever faced
* The physical toll of playing a heavy game
Leading by Example vs. Talking About Standards (24:01)
* Holding teammates to a high standard, and showing them why
* Why teammates need to see your work ethic every single day
* Managing different personalities and knowing how to reach each player
* The evolving nature of culture in a locker room
The 2007 Ducks Run and Championship Culture (29:46)
* A veteran core with different leadership styles: Scotty Niedermayer, Teemu Selanne, Rob Niedermayer
* The self-policing group that didn’t need one person grinding all the time
* Winning for Teemu, winning for Jiggy, winning for each other
The Heart-Stopping Incident and Ripping the Band-Aid Off (32:05)
* Blocking a shot that hit him in the heart, commotio cordis
* Stopping breathing for 25-30 seconds and the surreal aftermath
* Playing two days later to avoid the stigma and the questions
* Comparing his experience to Damar Hamlin’s
The Eye Injury, Losing His Sixth Sense, and Forced Retirement (37:45)
* The stick to the eye that ended his career
* Losing the spatial awareness that made him elite
* Watching the game from the outside and realizing at 40 it was too fast
* Evolving from “what if I was playing” to “how can I help players get better?”
Controlling What You Can Control (44:24)
* Learning to park the game at the door and not stew on mistakes
* The maturity to separate performance from identity
* Sleeping better, recovering faster, and playing longer
The Year Off and Avoiding Post-Career Pitfalls (46:42)
* The best advice he ever received: take meetings, listen, wait a year
* Retraining his eye and healing his head for 18 months
* Why jumping into the next thing too fast is a trap
Investment Mistakes and Lessons Learned (51:03)
* Prioritizing people over the deal itself
* The red flags, last-minute asks, rushed timelines, and fine print
* Sleeping on every decision and never committing on the spot
Writing Earned and Taking Off the Armor (54:17)
* The hardest truths to put on the page
* Why hockey stories alone weren’t enough: mistakes, growth, and evolution
* The message that everything in life is earned, no shortcuts, no handouts
Parenting, Legacy, and the No-”What-If” Rule (57:21)
* No what-if games in the Pronger household
* You can’t cherry-pick moments; everything changes with every fork in the road
* No rearview mirrors, learn, grow, evolve, and keep moving forward
About Chris Pronger
Chris Pronger is a Hockey Hall of Famer, Norris Trophy winner, Hart Trophy winner, Stanley Cup champion, and two-time Olympic gold medalist. Over a 20-year NHL career, he played for the Hartford Whalers, St. Louis Blues, Edmonton Oilers, Anaheim Ducks, and Philadelphia Flyers. Known for his physical dominance, elite hockey sense, and relentless conditioning, Pronger was named one of the NHL’s 100 greatest players. Since retiring, he has focused on his family, his wife Lauren’s luxury travel company, Inspired Travels, and sharing the hard-earned lessons of his career through his 2026 book, Earned: The True Cost of Greatness from One of Hockey’s Fiercest Competitors.
* Building the inference infrastructure for Luma’s launch
* Scaling from roughly 500 to 9,000 H100s in six hours as Dream Machine went viral
What a Viral AI Launch Actually Looks Like (06:03)
* The request queue hitting 100,000 during the Dream Machine launch
* Processing half a million videos in 12 hours and reaching one million users in four days
* Why having a queue protected the user experience during the surge
* Building infrastructure that could run across raw VMs, Slurm, Kubernetes, and different GPU providers
* Why founders need to plan for success before the product takes off
Why AI Production Infrastructure Is Being Left Behind (10:50)
* The tension between training the next model and supporting production workloads
* Why infrastructure teams can lose talent to model research
* The opportunity Keegan saw in building a dedicated ML infrastructure team
* Creating infrastructure that model labs across different modalities can use instead of rebuilding it themselves
Why Video AI Needs a Different Infrastructure Stack (12:32)
* The limitations of moving media through traditional object storage
* The latency problems that make real-time previews and interaction difficult
* Streaming audio, video, images, and text as continuous inputs and outputs
* uRUN’s focus on making persistent, interactive AI experiences easier to build
* Moving AI from something you message toward something that feels present with you
The Shift Toward Omnimodal and Interactive AI (19:01)
* What Keegan learned working closely with Luma’s research team
* Why understanding the research direction matters when building infrastructure
* The move toward AI that can understand vision, audio, language, reasoning, and sensor data
* How AI has evolved from single prompts to conversations, agents, and interactive systems
* Why highly interactive, real-time AI experiences could become the next major interface
Small Models, Specialized AI, and the Future of Inference (26:31)
* Keegan’s previous startup thesis around smaller models and delegated inference
* Why continual learning remains a difficult problem
* Running capable smaller models locally and knowing when to delegate to larger models
* Why enterprises may increasingly want differentiated models running in-house
* The potential shift toward using large models for the hardest problems rather than every task
Where uRUN Is Seeing Early Demand (30:38)
* AI avatars for customer support and sales
* Steerable video generation that lets users intervene while content is being created
* Video transformation for creators, avatars, and live experiences
* Real-time visual effects for music festivals and live events
* Why world models could eventually have applications in open-world gaming
The Infrastructure Problem Holding Back World Models (00:32:54)
* Companies developing world models without the infrastructure to serve them
* Why scaling world models remains difficult
* The enormous context requirements involved in tracking everything happening in a simulated environment
* The need for distributed infrastructure as these models become more capable
Building a Team Around Hard Problems (35:18)
* Finding engineers with deep experience in infrastructure and low-latency inference
* Bringing together expertise from New Relic, AWS, Superorbital, and other infrastructure environments
* Why Keegan looks for engineers who can work across multiple areas
* Building a small team of high-leverage people instead of optimizing for headcount
The Trait Keegan Looks for in Exceptional Engineers (37:47)
* Why culture and quality matter more than quantity
* Looking for people who take ownership and solve problems without waiting for instructions
* The importance of urgency and experience operating under pressure
* Why hard problems can attract customers, investors, and exceptional talent
* Hiring people who can wear multiple hats and produce at a high level
Building AI Companies in Canada (41:29)
* Why Keegan keeps finding Canadians throughout Silicon Valley
* The advantages of building a strong team in Canada at a lower cost
* Government funding and the opportunity to build ambitious companies with smaller teams
* The challenge of Canadian companies and talent being pulled toward Silicon Valley
* Why Canada needs more ways for companies to grow instead of selling early
Selling Infrastructure to Developers (44:23)
* Why developers want to try the product rather than hear a list of performance claims
* Giving technical users something they can get their hands on and test
* Why open-source surfaces can help developers understand how a product works
* Documentation and developer experience as a core part of selling infrastructure
* Why developers have a very high tolerance bar for technical errors
The Infrastructure Shift Coming Next (46:43)
* Why persistent streaming infrastructure could become standard
* Moving away from request-response systems toward long-running streams
* The importance of maintaining state across continuous interactions
* Potential applications in real-time video, virtual try-on, image editing, and coding agents
* The infrastructure required for AI systems that can generate and respond almost instantly
About Keegan McCallum
Keegan McCallum is the co-founder and CEO of uRUN, an inference provider built to handle persistent, steerable, and interactive AI experiences. A self-taught engineer who started by jailbreaking iPods in Thunder Bay, Keegan has built a career on tackling the hardest infrastructure problems in Canada. He has held leadership roles at Colony Networks and served as the Head of Engineering at Luma AI, where he led the infrastructure team that scaled the viral Dream Machine launch from 500 to 9,000 GPUs in a single day. His deep technical expertise spans ML infrastructure, cloud-native systems, and low-latency edge computing.
Ontario rolls out new rules forcing AI data centers to pay higher electricity rates and cover infrastructure costs. John says the move was inevitable and raises legitimate questions about whether AI’s benefits will be widely shared.
Anthropic’s Super-Voting Share Plan (12:52)
Anthropic plans super-voting shares and a trust to insulate its founders, who own only about 2% each, ahead of a potential $2 trillion IPO. John calls it bad governance but admits the public likely won’t care given the company’s explosive growth.
Stripe Stays Private and Buys Big (17:24)
Stripe acquires OpenRouter for $8 billion in stock while staying private, with revenues up 41% and free cash flow rising 43%. John asks why they’d ever go public if secondary markets provide liquidity and they can avoid quarterly scrutiny.
Clearco’s Comeback (19:48)
Clearco secures a $100 million Macquarie facility, cutting its cost of capital by 50% in a stunning turnaround. The chairman describes it as rebuilding an airplane mid-flight, and they’ve pulled it off.
Is Canada Losing the Blockchain Race? (20:56)
With U.S. crypto rules advancing and Canada stalled since the Stablecoin Act, John warns the real opportunity is in unified ledgers, not currencies. He notes Canada’s best blockchain talent is building for American companies, not Canadian ones.
* How jets overhead and allied ships shaped his early view of technology and defense
* The BBS era and the thrill of finding information that wasn’t available to everyone
From Mobile Data Skepticism to Building Canada’s First High-Speed Network (05:31)
* Why people thought mobile internet was “the stupidest thing” in the early 2000s
* Building a data-only carrier when no one believed you’d want internet everywhere
* The Nokia Communicator as his favorite tech gadget and early glimpse of mobile data
* Connecting critical infrastructure and discovering default credentials left wide open
The Wake-Up Call: Wastewater Plants and Unsecured Dams (12:58)
* Finding a wastewater flow control valve dangling on the internet with admin/admin credentials
* The “air-gapped” power plant where an engineer plugged his BlackBerry in to charge
* How Shodan and friends revealed dams and power facilities publicly accessible
* The founding of Lastwall: “Hackers will be everywhere. We’ve got to do something.”
From Behavioral Biometrics to Quantum Resilience (19:11)
* Why 85% of hacks still use valid stolen credentials, the same as the 1990s
* Early experiments with keyboard dynamics, mouse movements, and cognitive biometrics
* Tracking Peter Shor’s algorithm since university and the IBM factorization of 15 in 2001
* The 2017 to 2018 decision to embed quantum resiliency natively into Lastwall
Selling to the Pentagon: DIU and the “Hard Mode First” Strategy (26:07)
* Landing the first major deployment with the U.S. Department of Defense Innovation Unit
* How DIU pioneered procurement that matches innovation cycles, months instead of years
* The advice from Carbon Black founders: build the regulated stack first
* Why defense tech used to shut VC doors and how times have changed
FedRAMP, Canada, and the Case for Harmonization (33:25)
* FedRAMP as the gold standard: do compliance once, reuse everywhere
* The Canadian challenge: every agency doing its own security review
* Why Canada should base its program on NIST 800 and harmonize with the U.S.
* The reality of the integrated North American power grid and shared defense
AI Agents and the Blast Radius of Credential Theft (37:44)
* Why 50 to 100 agents per human in 2 to 3 years will magnify damage exponentially
* The OpenClaw lesson: agents do what agents do, not what you expect
* The “YOLO” approach to AI deployment and why enterprises aren’t calling enough
* Advice for founders: sandbox first, don’t connect your whole drive, go slowly
The $60M Series A Extension and the Path Forward (43:13)
* Raising BDC Capital’s Strong North Fund led by Major General (Ret.) Peter Dawe
* The milestone of FedRAMP certification and opening the floodgates to U.S. agencies
* Deploying in disconnected environments: field containers for critical infrastructure
* Why defense is ultimately about protecting the economy
About Karl Holmqvist
Karl Holmqvist is co-founder and CEO of Lastwall, an identity-as-a-service platform built on Zero Trust principles and public key infrastructure, hardened with post-quantum cryptographic resilience. Lastwall serves the U.S. Department of Defense and a growing number of civilian government agencies and critical infrastructure operators. Karl has been a cybersecurity enthusiast since the 1990s, with a background spanning telecommunications infrastructure (including building one of Canada’s first high-speed mobile data networks), renewable energy infrastructure across the Middle East, North Africa, and Southern Europe, and international investing. He studied at Mount Allison University and is based in Vancouver, BC.
John argues that defence and other sensitive infrastructure cannot depend entirely on foreign providers, making sovereign technology a strategic necessity.
The AI Data Center Backlash Is Getting Political (09:19)
AI data centers are running into growing resistance over electricity demand, water use, and the strain they place on local infrastructure.
John believes the issue could become much more political in Canada if rising AI demand starts pushing up energy costs for everyday consumers.
Zuckerberg Wants to Decentralize AI Power. Really? (14:48)
Mark Zuckerberg is pushing a vision of personal superintelligence that puts powerful AI tools into the hands of individuals and small businesses.
John agrees with some of the open-source philosophy, but calls out the contradiction of hearing a message about decentralizing power from the founder of Meta.
Can One SpaceX Bet Change How Pension Funds Think? (18:55)
Ontario Teachers’ SpaceX investment shows how a single exceptional venture bet can have a meaningful impact even inside a massive pension portfolio.
John explains why pension funds should remain disciplined, but says wins like SpaceX and Shopify prove that venture capital absolutely can move the dial.
* Why he chose Bain over academia and how consulting shaped his career
* Joining TorQuest and zeroing in on non-bank financial services
Finding the Kernel: HealthSmart Financial Services (05:18)
* The summer of 2013, losing a deal but falling in love with the point-of-sale lending model
* Why banks ignored this niche and how technology was changing the game
* Spinning out a tiny five-person division with no CEO
The Pivot to E-Commerce (10:14)
* Doubling the health business in 2016 and realizing it would take forever
* The epiphany: Canada had no point-of-sale financing for e-commerce
* Mapping out the user experience over Christmas 2016 and pre-selling Casper and Endy
Building PayBright: Scrappy, Fast, and Capital Efficient (15:00)
* Running a “double-headed monster,” healthcare and e-commerce side by side
* Advice for founders navigating platform shifts, from legacy platforms to AI-native products
* The economics of buy now, pay later, merchant fees, interest rates, and cost of risk
The Affirm Acquisition (21:02)
* Growing annual loan volume from $6 million to $220 million in five years
* The COVID boom and inbound interest from Klarna, RBC, TD, and Affirm
* Running a mini process, dos and don’ts for founders
Staying On: Becoming CRO at Affirm (27:34)
* Why he stayed past the earnout and has now been there for more than three years
* Lessons from Max Levchin and the “dog on a bone” approach to going deeper
* How to stay focused across multiple products and jurisdictions
Agentic Commerce and the Future of Shopping (33:09)
* What agentic commerce really means and what it doesn’t
* Why agents will read the fine print and guide consumers to better choices
* The partnerships with Google, Stripe, and Shopify
Banning Deferred Interest and Late Fees (36:04)
* Why deferred interest is “borderline abusive” and hard to defend
* Affirm’s no-late-fee, no-compounding, transaction-level underwriting model
* Aligning lender and consumer interests, the Max Levchin insight
From Private to Public: Lessons in Discipline (40:32)
* How being public forces discipline without over-dictating the quarter
* Advice for CROs on timing the public markets
* Why Stripe staying private proves there’s no one-size-fits-all path
AI at Affirm: Supercharging Revenue and Underwriting (44:11)
* The proliferation of AI tools internally and the excitement of experimentation
* How transformer-based models are improving underwriting
* The future of work, querying Slack for tribal knowledge in seconds
About Wayne Pommen
Wayne Pommen is Chief Revenue Officer at Affirm, where he oversees the company’s revenue-generating teams and products. He joined Affirm in January 2021 through its acquisition of PayBright, Canada’s leading buy now, pay later provider, which he founded and led as President and CEO starting in 2015, growing it from 5 to 250 employees with retail partners including Apple, Hudson’s Bay, Wayfair, Samsung, and Sephora. Before PayBright, Wayne was a Principal at TorQuest Partners and a consultant at Bain & Company. A former competitive rower for Canada’s national team, he holds a degree from Harvard and a PhD from Cambridge.
Julia Maltby is a Principal at Fengate Asset Management, where she invests in early-stage VC funds and direct opportunities across North America. She has lived the full VC lifecycle: she was the first employee at Plum Alley Investments, ran partnerships at WeWork, spent 5+ years rising from Associate to Principal at Flybridge Capital, and founded her own seed fund, Deco Ventures. She holds an MBA from Harvard Business School and writes about her LP experiences on her Substack, Julia’s Field Notes.
* AI as a democratizing force that makes everything faster and more competitive
* From CAD design to patent strategy: how AI is becoming a founder’s essential tool
* The commoditization of vertical robotics and what it means for defensibility
Building Moat in Deep Tech: Talent, Networks, and Network Effects (10:30)
* Why network effects and talent density matter more than patents alone
* How to pull the “ladder up” behind you as you scale
* Incumbents vs. upstarts: why everyone has access to the same tools now
The Rise of Deep Checks (18:01)
* How Deep Checks became the world’s largest network of deep tech founders and VCs
* The platform that helps founders run a tight, accelerated fundraising process
* Over $100 million deployed and 5,000+ founders submitted in just two years
What Jacob Looks for in Founders (24:50)
* The 50/50 split between team and idea
* Why obsession and speed matter more than business experience
* How to spot the founders who will learn to sell, recruit, and negotiate
Frontier Tech vs. Deep Tech (29:20)
* Why Julian Capital backs “picks and shovels” companies in spaces like fusion and quantum
* The importance of market pull and meaningful near-term milestones
* Why a 20-year fund cycle makes financial math nearly impossible
The Data That Surprised Everyone (32:58)
* Deep tech exits are 25% faster with more unicorns per dollar invested
* Why historical data shows deep tech outperforming software
* The role of capital flooding and dilution in venture returns
About Jacob Jackson
Jacob Jackson is a partner at Julian Capital and the founder of Deep Checks, the world’s largest network of deep tech founders and VCs. A physicist by training, Jacob pivoted from academic research to founding MedStack, a privacy and security SaaS platform, before returning to his engineering roots as an investor. He now backs founders building hardware and tackling the world’s hardest problems. Jacob is known for his data-driven approach, obsession with team quality, and candid takes on the future of venture capital.
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