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Tank Talks By Ripple Ventures

Tank Talks By Ripple Ventures

By: Ripple Ventures
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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.

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Episodes
  • CRO of Affirm on How “Buy now, pay later” Makes Money

    CRO of Affirm on How “Buy now, pay later” Makes Money
    Aug 7 2026
    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.–A big thanks to our sponsor, Moomoo CanadaThis 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.caFrom Cambridge to Bain to Private Equity (03:10)* The Oxford-Cambridge Boat Race, a broken wrist, and a comeback story* Why he chose Bain over academia and how consulting shaped his career* Joining TorQuest and zeroing in on non-bank financial servicesFinding 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 CEOThe 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 EndyBuilding 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 riskThe 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 foundersStaying 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 jurisdictionsAgentic 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 ShopifyBanning 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 insightFrom 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 pathAI 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 secondsAbout Wayne PommenWayne 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 ...
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    53 mins
  • The Money Behind Money in VC | Julia Maltby

    The Money Behind Money in VC | Julia Maltby
    Jul 30 2026
    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.Inside WeWork’s Hypergrowth Machine (05:11)* Joining WeWork during its explosive expansion and learning from one of startup history’s fastest growth stories.* What Adam Neumann got exceptionally right about building mission-driven teams.* The leadership lessons worth keeping and the scaling mistakes worth avoiding.The Flybridge Investing Framework (10:39)* Why durable venture investing starts with disciplined systems rather than intuition alone.* The importance of pricing integrity and staying focused on core business strengths.* How evaluating customer urgency shaped Julia’s investment philosophy.Becoming a Solo GP (14:14)* Launching Deco Ventures with Flybridge’s support.* The challenges of making investment decisions without partners.* Why every solo GP needs trusted people whose job is to challenge—not validate—their thinking.What Makes a Venture Manager Truly Different? (18:00)* Why there isn’t just one formula for becoming a successful GP.* Understanding your competitive advantage instead of copying other managers.* How LPs think about portfolio fit beyond fund performance.The Data Room Mistakes GPs Keep Making (23:18)* Why withholding information often slows fundraising rather than helping it.* Julia’s advice: send everything instead of drip-feeding documents.* How GPs should reference-check LPs before sharing sensitive materials.Looking Beyond Markups and Valuations (27:16)* Why portfolio KPIs matter more than inflated funding rounds.* How disciplined reserve strategies separate thoughtful investors from reactive ones.* Using follow-on decisions as a measure of investment discipline.The Power of Great References (31:45)* Why founders from failed companies often provide the strongest references.* How LP references reveal governance, transparency, and communication quality.* Why perfect references can actually make LPs more skeptical.Stop Leaving Meetings as a “Maybe” (34:35)* The questions every GP should ask before ending a fundraising meeting.* Understanding the difference between genuine interest and structural misalignment.* How qualifying LPs like a sales pipeline saves months of wasted fundraising.Building Better Co-Investment Relationships (37:06)* How proactive communication makes co-investments move faster.* Why LPs build internal pipelines long before deals officially launch.* The importance of giving institutional investors time to prepare.The Future of Early-Stage Venture (39:27)* Why Julia remains optimistic despite today’s challenging fundraising environment.* The growing divide between mega-funds and smaller venture firms.* Why smaller funds continue delivering meaningful returns that often go unnoticed.Using AI to Build Better LP Portfolios (41:17)* How Fengate uses AI to understand portfolio exposure across hundreds of startups.* Moving beyond broad fund branding into detailed market analysis.* Why better portfolio intelligence leads to better future investment decisions.About Julia MaltbyJulia ...
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    46 mins
  • Why Software Lost Its Moat and Deep Tech Is Winning with Jacob Jackson of Julian Capital

    Why Software Lost Its Moat and Deep Tech Is Winning with Jacob Jackson of Julian Capital
    Jul 23 2026
    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-marketRedefining 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 seededHow AI Accelerates Hardware Development (08:23)* 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 defensibilityBuilding 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 nowThe 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 yearsWhat 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 negotiateFrontier 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 impossibleThe 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 returnsAbout Jacob JacksonJacob 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.Connect with Jacob Jackson on LinkedIn: https://www.linkedin.com/in/jonlovekingsett?originalSubdomain=caVisit Julian Capital’s website: https://www.julian.capital/Submit to Deep Checks: https://www.deepchecks.vc/Connect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1Visit the Ripple Ventures website: https://www.rippleventures.com/ 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
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    45 mins
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