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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.

tanktalks.substack.comMatt Cohen Direction Economie Finances privées Management et direction
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  • 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
  • The Rundown 9/29/26: Quantum Reality Check, AI Risks, and Why Canada Is Missing Its Tech Opportunity

    The Rundown 9/29/26: Quantum Reality Check, AI Risks, and Why Canada Is Missing Its Tech Opportunity
    Sep 29 2026
    Welcome back to another thought-provoking episode of Tank Talks! Matt Cohen is joined once again by John Ruffolo to break down the biggest stories shaping the future of technology, investing, and Canada’s economy.From the market reaction following Xanadu’s SPAC lockup expiration to the growing debate around whether Canadian pension funds are investing enough in homegrown innovation, this episode explores the opportunities and risks facing investors, founders, and policymakers.John also shares his concerns around AI privacy, Meta’s personal AI agents, the massive infrastructure demands behind AI adoption, and the future liability risks that come with increasingly powerful technology.Plus, Matt and John dive into Canada’s budget debate and question whether accounting strategies are masking the true scale of government spending.As AI reshapes industries, investors rethink risk, and governments navigate economic uncertainty, the decisions being made today will define the next decade.Xanadu’s Market Reality: AI Opportunity or Overhyped Valuation? (04:45)After Xanadu’s SPAC lockup expired, the quantum computing company’s stock faced significant selling pressure, dropping sharply as early investors and shareholders gained the ability to sell.Matt and John discuss founder Christian Weedbrook’s decision to sell a portion of his shares while maintaining a majority stake, and why John views the move as a strategic step rather than a negative signal.Why Aren’t Canadian Pension Funds Backing More Canadian Innovation? (09:29)Matt and John examine a recent investment by a Canadian pension fund into Harvey Legal, an AI legal technology company, and question why similar-sized investments are not flowing into more Canadian startups.John argues that Canadian pension funds have the capital and ability to support domestic venture and growth-stage companies, but many remain underweight in Canadian innovation.The conversation explores whether institutions are doing enough to support companies like Clio, Float Financial, and other Canadian technology businesses that are building globally competitive products.Meta AI, Personal Agents, and the Privacy Trade-Off (12:04)Meta’s new AI assistant has created excitement across the technology world, but John raises a major question: how much personal information should consumers be willing to hand over to AI platforms?The discussion explores the growing popularity of AI agents that connect to email, calendars, and personal data, and whether convenience is worth the potential privacy risks.While Matt highlights the power and usefulness of personal AI assistants, John remains cautious about giving technology companies access to sensitive personal information.The Hidden Cost of AI Growth: Compute, Capital, and Liability (14:10)As AI adoption accelerates, Matt and John discuss the enormous infrastructure requirements needed to support these systems.From computing power and capital expenditures to potential legal liabilities, the next phase of AI growth may depend on whether companies can continue scaling while managing the costs behind the scenes.The conversation also touches on Anthropic’s upcoming IPO concerns and the unanswered questions surrounding liability when AI systems make mistakes or operate unpredictably.Canada’s Budget Debate: Are The Numbers Telling The Full Story? (16:06)Matt and John close the episode by examining Canada’s deficit projections and the government’s approach to separating operating expenses from capital spending.John challenges the idea that certain spending categories should be treated differently when evaluating the country’s financial position, comparing it to how companies can manipulate profitability by changing accounting treatment.The discussion raises a broader question: are governments presenting a clearer picture of their finances, or are accounting methods making the numbers harder to understand?Connect with John Ruffolo on LinkedIn: https://ca.linkedin.com/in/joruffoloConnect 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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    19 min
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