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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.

tanktalks.substack.comMatt Cohen
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Episodes
  • The Rundown 1/29/26: Garry Tan's Controversial Move: Y Combinator's New Rules for Canadian Companies
    Jan 29 2026

    In this episode of Tank Talks, Matt Cohen and John Ruffolo unpack the ripple effects of Y Combinator’s decision to exclude Canadian startups from their investment portfolio unless they’re incorporated in the U.S. or other tax-friendly jurisdictions. This move has sent shockwaves through the Canadian tech ecosystem, and Matt and John break down exactly why this matters for founders and investors alike.

    The conversation explores the myth of U.S. incorporation being the golden ticket for capital-raising and the rise of a narrative that Canadian entrepreneurs must leave their home country to achieve success. Matt and John challenge this narrative head-on, providing deep insights into why Canadian tech companies can still thrive domestically and refuting the data that YC used to justify their decision.

    Y Combinator Shakes Up Canadian Startups (01:09)

    YC has revised its investment criteria to exclude Canadian companies unless they’re incorporated in the U.S. or certain tax havens. The duo debates the implications of this shift and how it impacts Canadian founders who are now questioning their incorporation choices.

    The False Narrative of U.S. Incorporation (03:09)

    John breaks down the myth that U.S.-incorporated companies raise more capital than their Canadian counterparts, calling out misleading data points used by YC’s Garry Tan to justify the shift. The conversation digs into why this narrative is misleading and what Canadian entrepreneurs can do to counter it.

    Why YC’s Data Doesn’t Tell the Full Story (05:35)

    John explains how some of Canada’s most successful tech companies didn’t follow the YC path and still thrived, refuting the idea that incorporation in the U.S. is always the best move for Canadian startups.

    The Ripple Effect on Early-Stage Founders (06:25)

    The discussion turns to the younger generation of founders who now believe they must incorporate in the U.S. to succeed, potentially setting them up for unnecessary challenges.

    The Shift from PE to VC: Innovator’s Dilemma (14:07)

    Matt and John shift gears to discuss private equity’s struggle with legacy enterprise software companies in the wake of AI disruption. They explore how PE firms are transforming into venture funds to keep up with market changes, creating a new kind of investment landscape.

    The AI Crisis for Private Equity (15:10)

    As AI-native startups disrupt traditional software models, private equity firms face extended hold periods on their investments. Matt and John explore how firms like Thoma Bravo are adjusting their strategies to deal with these changes.

    CGI Partners with OpenAI: The Changing Consulting Landscape (18:54)

    The episode wraps up with a discussion on CGI’s new global alliance with OpenAI. This partnership marks a major shift in the IT consulting world, with CGI aiming to integrate AI at scale. Matt and John speculate on the future of AI in enterprise consulting and what this means for legacy players like CGI.

    Connect with John Ruffolo on LinkedIn: https://ca.linkedin.com/in/joruffolo

    Connect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1

    Visit 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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    21 mins
  • The Rundown 1/23/25: Truth Bombs at Davos, Chaos in Markets, Big IPOs Ahead
    Jan 23 2026

    In this episode of Tank Talks, Matt Cohen and John Ruffolo unpack Prime Minister Mark Carney’s China agreement and his Davos speech, calling out the collapse of the rules-based international order and pushing “middle powers” to coordinate against coercion. John and Matt agree the speech was sharp, but they hammer the real issue: Canada has to build leverage at home (resources, infrastructure, internal trade, and actual execution) or “diversifying” becomes a vibes-only strategy.

    The conversation then pivots to Trump’s Greenland framework, rare earth realities, and why the real choke point is processing, not just “owning minerals.” Finally, they switch lanes into markets, covering the biggest anticipated IPOs of 2026 (SpaceX, OpenAI, Databricks, Stripe, Revolut, Canva), why liquidity could snap back for LPs, and why SPACs are creeping back as a funding path for deep tech, including General Fusion’s SPAC and the emergence of the Canadian Rocket Company as Canada tries to repatriate space talent.

    Canada–China trade reset and what it actually means (02:13)

    Matt tees up the January 16 China agreement and the idea of trade diversification under U.S. tariff uncertainty. John frames it as a fix for specific trade pain (not a full political pivot) and warns against treating China as a “safe alternative.”

    Davos speech: “truth bombs” vs real-world action (04:11)

    They break down Carney’s Davos message on coercion, great power tactics, and middle-power coalitions. John calls it “spectacular,” but both stress the gap between rhetoric and measurable outcomes.

    Canada’s leverage problem: “build Canada first” (06:39)

    John argues Canada can’t diversify trade if it has nothing competitive and scalable to trade. The conversation turns into a blunt call for domestic execution: resources, pipelines, and the hard stuff that moves GDP.

    Matt’s frustration: Why no national address to Canadians? (08:06)

    Matt goes off on the lack of direct, plainspoken communication to Canadians about what has to change, what’s coming, and what tradeoffs might be required.

    Trump and Greenland: Bond markets, politics, and power (12:32)

    John calls Trump’s posture performative and points to constraints that actually matter, including internal GOP pressure and market reactions (he highlights the bond market as the real “adult in the room”).

    Top anticipated IPOs of 2026: the mega list (19:12)

    They run through what’s being floated as the monster class of potential offerings: SpaceX, OpenAI, Databricks, Stripe, Revolut, Canva (and more speculation). The bigger point: it’s not number of IPOs, it’s dollar value and liquidity unlock.

    Canada’s space bets: Canadian Rocket Company emerges (21:15)

    Matt shares CRC’s emergence from stealth with $6.2M funding (all Canadian investors including BDC and Garage). Focus: repatriating SpaceX/Blue Origin talent and pushing Canada deeper into the space industrial base.

    Connect with John Ruffolo on LinkedIn: https://ca.linkedin.com/in/joruffolo

    Connect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1

    Visit 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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    24 mins
  • Building a Solo GP Fund with Timothy Chen of Essence VC
    Jan 22 2026
    In this episode of Tank Talks, Matt Cohen sits down with Timothy Chen, the sole General Partner at Essence VC. Tim shares his remarkable journey from being a “nerdy, geeky kid” who hacked open-source projects to becoming one of the most respected early-stage infrastructure investors, backing breakout companies like Tabular (acquired by Databricks for $2.2 billion). A former engineer at Microsoft and VMware, co-founder of Hyperpilot (acquired by Cloudera), and now a solo GP who quietly raised over $41 million for his latest fund, Tim offers a unique, no-BS perspective on spotting technical founders, navigating the idea maze, and rethinking sales and traction in the world of AI and infrastructure.We dive deep into his unconventional path into VC, rejected by traditional Sand Hill Road firms, only to build a powerhouse reputation through sheer technical credibility and founder empathy. Tim reveals the patterns behind disruptive infra companies, why most VCs can’t help with product-market fit, and how he leverages his engineering background to win competitive deals.Whether you’re a founder building the next foundational layer or an investor trying to understand the infra and AI boom, this conversation is packed with hard-won insights.The Open Source Resume (00:03:44)* How contributing to Apache projects (Drill, Cloud Foundry) built his career when a CS degree couldn’t.* The moment he realized open source was a path to industry influence, not just a hobby.* Why the open source model is more “vertical than horizontal”, allowing deep contribution without corporate red tape.From Engineer to Founder: The Hyperpilot Journey (00:13:24)* Leaving Docker to start Hyperpilot and raising seed funding from NEA and Bessemer.* The harsh reality of founder responsibility: “It’s not about the effort hard, it’s about all the other things that has to go right.”* Learning from being “way too early to market” and the acquisition by Cloudera.The Unlikely Path into Venture Capital (00:26:07)* Rejected by top-tier VC firms for a job, then prompted to start his own fund via AngelList.* Starting with a $1M “Tim Chen Angel Fund” focused solely on infrastructure.* How Bain Capital’s small anchor investment gave him the initial credibility.Building a Brand Through Focus & Reputation (00:30:42)* Why focusing exclusively on infrastructure was his “best blessing” creating a standout identity in a sparse field.* The reputation flywheel: Founders praising his help led to introductions from top-tier GPs and LPs.* StepStone reaching out for a commitment before he even had fund documents ready.The Essence VC Investment Philosophy (00:44:34)* Pattern Recognition: What he learned from witnessing the early days of Confluent, Databricks, and Docker.* Seeking Disruptors, Not Incrementalists: Backing founders who have a “non-common belief” that leads to a 10x better product (e.g., Modal Labs, Cursor, Warp).* Rethinking Sales & Traction: Why revenue-first playbooks don’t apply in early-stage infra; comfort comes from technical co-building and roadmap planning.* The “Superpower”: Using his engineering background to pressure-test technical assumptions and timelines with founders.The Future of Infra & AI (00:52:09)* Infrastructure as an “enabler” for new application paradigms (real-time video, multimodal apps).* The coming democratization of building complex systems (the “next Netflix” built by smaller teams).* The shift from generalist backend engineers to specialists, enabled by new stacks and AI.Solo GP Life & Staying Relevant (00:54:55)* Why being a solo GP doesn’t mean being a lone wolf; 20-30% of his time is spent syncing with other investors to learn.* The importance of continuous learning and adaptation in a fast-moving tech landscape.* His toolkit: Using portfolio company Clerky (a CRM) to manage workflow.About Timothy ChenFounder and Sole General Partner, Essence VCTimothy Chen is the Sole General Partner at Essence VC, a fund focused on early-stage infrastructure, AI, and open-source innovation. A three-time founder with an exit, his journey from Microsoft engineer to sought-after investor is a masterclass in building credibility through technical depth and founder-centric support. He has backed companies like Tabular, Iteratively, and Warp, and his insights are shaped by hundreds of conversations at the bleeding edge of infrastructure.Connect with Timothy Chen on LinkedIn: linkedin.com/in/timchenVisit the Essence VC Website: https://www.essencevc.fund/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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    1 hr and 5 mins
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