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Tank Talks By Ripple Ventures

Tank Talks 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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  • The "Prepared Mind" Investing Strategy Behind Sierra Ventures' Biggest Bets | Shomik Ghosh

    The "Prepared Mind" Investing Strategy Behind Sierra Ventures' Biggest Bets | Shomik Ghosh
    Oct 22 2026
    In this episode of Tank Talks, host Matt Cohen sits down with Shomik Ghosh, Partner at Sierra Ventures, to explore his unique path from the fixed income trading floor to the forefront of deep tech and hard tech investing. Shomik shares his journey from a liberal arts education to Wall Street, his pivotal role at Top Tier Capital, and his nearly six-year tenure at Boldstart Ventures, where he learned the craft of inception-stage investing.They break down why a “generalist approach with a prepared mind” is a venture superpower, how to build and maintain long-term LP relationships, and the crucial difference between “deep tech” and “hard tech.” Shomik opens up about the art of using public market research to gain an edge in private markets, the future of AI and robotics, and why the biggest threat to the AI industry isn’t regulation, but “token maxing.” He also shares his insights on leadership, the value of a non-traditional information diet, and his personal philosophy on health, presence, and family.Whether you’re exploring research-driven deep tech, complex hard tech systems, or the increasingly blurred line between the two, this conversation offers a thoughtful look at how to spot emerging signals, build conviction early, and invest with a broader perspective.The Generalist Advantage: From Fixed Income to Venture Capital (02:15)* How a background in fixed income sales and trading provides a unique lens for understanding cash flow and leverage in venture.* Why the world needs more generalists, not just specialists, and how being curious across industries creates the strongest returns.* The unexpected parallels between structuring complex debt and untangling today’s private credit markets for AI data centers.Lessons from the LP Side: Top Tier Capital and the Long Game (04:57)* Why Top Tier’s fund-to-fund model gives them an edge in backing emerging managers.* The critical importance of a regular cadence of communication with LPs, beyond the annual AGM.* Understanding what different LPs want, why fund-of-funds chase co-investments while pension funds prioritize macro allocation.* The value of treating LPs as human relationships, not just transactional ones.The Art of the 180: Transitioning from Growth to Inception at Boldstart (10:46)* How a shared investment in Snyk led to a deep professional relationship with Boldstart’s Ed Sim.* The mental shift from seeing companies with $5M+ ARR to pre-product startups.* Why getting “a few layers below the C-suite” is essential for building deep, lasting relationships and understanding a company’s true health.The Three C’s of Venture: Cheer, Chill, and Challenge (15:03)* Ed Sim’s “3 C’s” framework for supporting founders: Cheer when things are down, Challenge when things are good, and Chill to let them cook.* The importance of knowing when to course-correct if a team is building in a silo.* Witnessing the power law in action: Snyk’s journey from <$2M to $300M ARR.The Move to Sierra Ventures: Flexibility, People, and Prepared Minds (19:17)* Why the move from a focused inception fund to a multi-stage firm like Sierra was the right fit for long-term flexibility.* The importance of “clicking” with the team, from Mark Fernandes to Tim and Ben.* How Sierra’s “all hands on deck” approach to pitch meetings, including non-investment roles, differentiates them from founders.Deep Tech vs. Hard Tech: Navigating Frontier Investments (25:51)* Shomik’s distinction between “deep tech”, research-driven, like silicon carbide for AR glasses, and “hard tech”, complex systems integration, like maritime defense.* How to assess demand signals for each category, from clear market needs to observing geopolitical shifts.* The crucial role of public markets in understanding supply chains for private companies in robotics and defense.Using Public Markets to Sharpen Private Market Bets (30:00)* How listening to investor days for companies like Waste Management and ATI provides unique insights into bottlenecks in turbines and superalloys.* The power of “Qurater” and other tools to distill first-party information from public companies.* Why having a base of first-party knowledge is essential for using AI effectively, or you just get “AI slop.”AI, Robotics, and the Future of Compute (36:56)* The three sub-trends in robotics: humanoids, foundation models, and vertical robotics.* The critical shortage of munitions and propulsion systems, and the need for advanced materials.* Why photonics is a massive area with exploding backlogs, and how companies are betting on co-packaged optics.* Debunking the “open vs. closed” source debate, why both will coexist and push the frontier.Underhyped Productivity and the “Token Maxing” Trap (48:35)* Why the recent pullback in “token maxing” is bullish for the long-term health of the AI industry.* Concrete signs of AI productivity in traditional verticals, from radiologists doing ...
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    56 min
  • Why Investors are Betting on Canadian Startups | NRTH Conference

    Why Investors are Betting on Canadian Startups | NRTH Conference
    Oct 15 2026
    In this special episode of Tank Talks, recorded at NRTH Festival (formerly Elevate) in downtown Toronto, host Matt Cohen chats with three prominent investors and operators to explore the state of the Canadian tech ecosystem. Michael Garrity, retired CEO of FinanceIt and co-chair of the C100, discusses why Canadian founders need to get better at telling their stories and how the Canada Investment Summit signals growing global interest. Isaac Souweine (Venture Science Fund at Mila) breaks down how Canada’s AI research institutions are pivoting toward commercialization and why we need to calibrate globally, not locally. Elizabeth Yin of Hustle Fund shares why Toronto is her favorite place to scout, the importance of hustle over hype, and how community-building creates lasting founder networks.They explore why there’s never been a better time to build or join early-stage companies, the public markets gap for Canadian startups, how Mila and Vector are responding to talent poaching from big labs, and what it takes to get non-tech capital off the sidelines. Whether you’re a founder, investor, or someone working in a Bay Street tower wondering if you should make the leap, this conversation offers a rare window into where the Canadian ecosystem is headed.Michael Garrity: Telling Canadian Stories and the C100 Mission (03:15)* The C100’s role in keeping Canadian companies in Canada by connecting them to Silicon Valley networks* Why Canadian founders are “crap at telling our stories” and the need to celebrate success* The Canada Investment Summit and why global investors are paying attention* Why the government’s job is to open regulatory spigots, not close deals* The public markets gap: why Canada needs better IPO infrastructure for early-stage companies* The cost of building has dropped to the lowest level ever, so why there’s never been a better time to startIsaac Souweine and the Venture Science Fund: Commercializing Canada’s AI Advantage (09:20)* Mila as the largest collection of AI researchers in the world* The cultural pivot at Mila: from pure research to supporting startups* How external pressure from OpenAI, Anthropic, and Amazon triggered internal change* The 15-person incubation group at Mila providing programs and services* Why Canadian founders need to calibrate globally, not locally* Playing offense by mobilizing Mila and Vector alumni in the Valley to do deals on their turf* What’s coming next: GPU optimization, AI intersection with biotech and material science, robotics, and physical AIElizabeth Yin and Hustle Fund: The Vibe, The Hippocorn, and Global Pre-Seed Investing (16:00)* Hustle Fund’s nine-year history and 700-company portfolio* Why Toronto is Elizabeth’s favorite place to scout: talent, maturity, and less competition than SF* How less capital forces founders to become better business people* The Hustle Fund approach: pre-revenue, under $10M post, and no thesis, just listening to founders* Maintaining community through Hustle Camp and the importance of kindness* AI in the pitch review process (yes, they use it) and how they see 1,000 companies a monthAbout Michael GarrityMichael Garrity is the retired CEO and current Executive Chair of FinanceIt, one of Canada’s leading fintech success stories. He is co-chair of the C100 alongside Mike Wessinger, focused on helping Canadian companies scale globally while staying rooted in Canada.Connect with Michael Garrity: https://www.linkedin.com/in/michael-garrity-7a87152/About Isaac SouweineIsaac is a partner at the Venture Science Fund, part of the Mila Institute in Montreal. With 10 years in the Canadian VC game at Real Ventures and Pender, he previously ran FounderFuel, one of Canada’s leading accelerators. He holds a background as a product manager and is focused on commercializing Canada’s world-class AI research.Connect with Isaac on LinkedIn: https://www.linkedin.com/in/isaacsouweine/Learn more about Mila: https://mila.quebec/enAbout Elizabeth YinElizabeth Yin is a co-founder and General Partner at Hustle Fund, a pre-seed venture fund that invests globally in early-stage companies. With a portfolio of over 700 companies, Hustle Fund is known for its founder-friendly approach and vibrant community. Elizabeth is based in San Francisco and is an active scout in the Toronto ecosystem.Connect with Elizabeth Yin: https://www.linkedin.com/in/elizabethyin/Learn more about Hustle Fund: hustlefund.vcConnect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1Visit the Ripple Ventures website: 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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    22 min
  • The Billable Hour is Broken: How Blackletter is Redesigning Law for Startups | Jonathan Rosenbluth (CEO and Co-Founder)

    The Billable Hour is Broken: How Blackletter is Redesigning Law for Startups | Jonathan Rosenbluth (CEO and Co-Founder)
    Oct 8 2026
    In this episode of Tank Talks, host Matt Cohen sits down with Jonathan Rosenbluth, co-founder of Blackletter, to trace his path from a Harvard JD and McKinsey consultant to employee number 20 at Cohere, and finally to building an AI-native law firm from the ground up. Jonathan shares how a chance networking call led him to Cohere’s founders, why he chose to bet on an unproven startup over a legal career, and how nearly five years scaling go-to-market, partnerships, and product functions shaped his conviction that law itself needed to be rebuilt, not just tooled up.They dig into why the billable hour exists in the first place, how its incentives quietly shape lawyer and client behavior, and why Jonathan believes the only way to fix legal services is to become the law firm rather than sell software to one. He explains Blackletter’s wedge into venture financing and commercial contract work, how fixed-fee pricing and a “harness” built around foundation models let the firm move at startup speed, and why he thinks the shift coming to law firms will rival what e-commerce did to retail.Whether you’re a founder tired of unpredictable legal bills, an investor watching the AI-native services wave, or just curious what it takes to leave law only to end up building a law firm, this conversation offers a founder’s-eye view of an industry on the edge of structural change.Finding Consulting, Then Entrepreneurship (01:36)* Splitting a 2L summer between a law firm and McKinsey, and why consulting “lit him up”* Early McKinsey projects with financial institutions across Canada, the US, and Jamaica* McKinsey’s culture of feedback and investment in people’s growth* Founding Campus Coupon in undergrad as a non-technical first stab at building somethingThe Accidental Path to Cohere (02:59)* Moving back to Toronto and deciding to jump into a startup* A pandemic-era virtual networking night, his wife’s insistence, and meeting a Cohere investor* Getting connected to the founders after the first business-hire candidate called AI “magic”* A walk with Aidan and Nick debating AI vs. nuclear as the most exciting problem in the worldInside Cohere: From “Everything Guy” to Product Lead (05:16)* Joining as employee number 20, doing “everything outside of training models”* Leading sales, partnerships, and biz ops before making the jump to product* Why he advises consultants and lawyers eyeing startups to “go early”* Early hypergrowth lessons: raising the Series A, launching early access, landing a Google partnership* Overcoming imposter syndrome moving into product with no technical backgroundThe Problem That Pulled Him Back to Law (09:38)* Nearly five years at Cohere and why leaving still felt like “being pulled toward” the next problem* Diagnosing what’s broken in law: unpredictable bills, slow turnarounds, misaligned incentives, unhappy lawyers, inaccessible top-tier services* Why the technology is finally capable of solving it, if the incentive problems get solved tooA Brief History of the Billable Hour (12:03)* The 1950s American Bar Association push to bill by the hour, tied to lawyer earnings falling behind doctors’* How billing by the hour incentivizes time spent over client outcomes* Parallels to real estate commissions and misaligned transaction incentivesWhy Build a Firm, Not a Copilot (13:19)* The limits of giving lawyers tools without redesigning the underlying workflow* Why becoming the law firm, not a vendor to law firms, is the only way to make top-tier legal services abundant* The founding team: David (frontier technology, ex-Cohere), Avi (top-tier lawyer and former Blue Jay Legal COO), and Jonathan (product, go-to-market, and scaling experience)Blackletter’s Wedge: Venture Financing and Commercial Contracts (16:55)* Why client pain in fundraising and commercial deal delays made the natural starting point* Real founder horror stories: six-figure legal bills, wrong currencies on closing documents, deals stalled by unnecessary aggression* Fixed, upfront pricing sheets instead of hourly billing* Working inside clients’ Slack channels and turning work around same-dayThe Harness: Building Technology Around Frontier Models (23:52)* What a “harness” means and why foundation models alone aren’t enough* Being model-agnostic and riding the wave of improving frontier models* Where Blackletter’s proprietary IP actually lives: the system around the model, not the model itself* How lawyers become the judgment layer rather than the bottleneck that kicks off every taskDisrupting Big Law: Trust, Talent, and the Coming Shift (26:56)* Why top-tier lawyers want to practice at the highest level, not defend billable hours* The widening gap between rising expectations and slower paths to partnership* Why Jonathan sees law as fundamentally “a trust business,” not a relationships business* Predicting a shift for law firms as large as e-commerce’s disruption of retailBuilding in ...
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    37 min
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