Tank Talks By Ripple Ventures

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.com

  1. Bring it Home: Canada's Regulatory Gridlock & Real Estate Recovery with Jon Love of KingSett Capital

    3D AGO

    Bring it Home: Canada's Regulatory Gridlock & Real Estate Recovery with Jon Love of KingSett Capital

    In this episode of Tank Talks, host Matt Cohen sits down with Jon Love, founder and executive chair of KingSett Capital, one of Canada’s largest and most experienced private equity real estate platforms. A seasoned investor who has navigated multiple market cycles, Jon is known for his frank, unfiltered takes on Canadian policy, regulation, and capital deployment, and this conversation is no different. Jon shares his honest assessment of the federal government’s newly announced $25 billion Canada Strong sovereign wealth fund, the push to fast-track major resource projects, and what’s really holding Canada back: not a shortage of capital, but a shortage of permission. He also breaks down where the real estate market stands today across office, retail, industrial, and residential, and why he believes a sharp recovery is coming for those with the balance sheet to wait it out. Whether you’re a developer, investor, policy watcher, or simply trying to understand what’s actually happening in the Canadian economy, Jon Love delivers the kind of straight talk that cuts through the noise. Canada’s $25 Billion Sovereign Wealth Fund: Progress or Déjà Vu? (02:48) * Jon’s honest take on the Canada Strong fund and what’s still missing * Why the real barrier to investment isn’t capital, it’s permission * Lessons from the Heritage Fund and what discipline looks like in practice Resource Fast-Tracking and the Major Projects Office (08:36) * The bull and bear case for Tim Hodgson’s promise of 5–10 shovel-ready projects by spring 2027 * What regulatory bottlenecks remain under the Carney government * Why Shell’s takeover of Arc Resources signals renewed confidence and what still needs to happen next Institutional Capital Coming Home (14:50) * What’s different about this wave of pension fund repatriation * OMERS, the Maple Eight, and why Canadian real estate returns are among the best in the world * The case for Canada as a technology superpower and why Jon is more optimistic than most The Real Estate Cycle: Where We Are and What’s Coming (20:25) * Triple-A office as the surprise strongest asset class in the country * Why for-sale residential is in pain and why a sharp recovery is inevitable * How banks are behaving with stressed borrowers, and the Oxford story from 1992 that defined a strategy Creative Repurposing, Affordable Housing, and the HST Rebate (30:44) * Office-to-hotel conversions in Toronto and why adaptive reuse is just getting started * Why streamlining affordable housing approvals matters more than new funding programs * The HST rebate: right medicine, but the prescription still isn’t written Media, Trade Wars, and What Jon Would Tell Carney (33:24) * Why the Port of Vancouver’s seven-day container turnaround vs. Dubai’s seven hours is a symbol of a much bigger problem * How media fragmentation and social media have made constructive policy debate nearly impossible * The one frank piece of advice Jon would give Prime Minister Carney if he had 15 minutes: give permission About Jon Love Jon Love is the founder and executive chair of KingSett Capital, one of Canada’s leading private equity real estate platforms. With decades of experience across multiple market cycles, Jon has built a reputation for candid, principle‑driven commentary on Canadian policy, regulation, and investment. He is a former CEO of Oxford Properties and has been a key figure in shaping Canada’s institutional real estate landscape. Beyond investing, Jon is known for mentoring young talent, championing affordable housing, and relentlessly advocating for cutting red tape. Connect with Jon Love on LinkedIn: https://www.linkedin.com/in/jonlovekingsett?originalSubdomain=ca Visit KingSett Capital website: https://www.kingsettcapital.com/ 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

    44 min
  2. The Rundown 4/28/26: Canada’s $25B Sovereign Wealth Fund: Genius Move or Political Slush Fund?

    APR 28

    The Rundown 4/28/26: Canada’s $25B Sovereign Wealth Fund: Genius Move or Political Slush Fund?

    In this episode of Tank Talks, Matt Cohen and John Ruffolo break down one of the biggest economic policy announcements in Canada’s innovation economy: Mark Carney’s proposed $25 billion Canada Strong Fund, a sovereign wealth fund designed to invest in nation-building projects, strategic industries, Canadian technology companies, and long-term economic sovereignty. John, who previously argued for this type of fund in his Substack piece Canada’s Missing Pot of Gold, explains why Canada’s biggest structural problem is undercapitalization and why relying on foreign direct investment for critical industries creates serious sovereignty risks. Matt and John dig into the hard questions behind the fund: Where does the money come from? Can Canada borrow at low rates and invest for long-term returns? How should the fund be governed so it does not become a political slush fund? And can this vehicle finally force a more serious conversation around Canadian pension funds, domestic capital formation, and backing companies like Cohere, Kepler, and Xanadu before they are pushed toward foreign capital markets? The episode also covers Cohere’s acquisition of German AI firm Aleph Alpha, the rise of sovereign AI alternatives outside the U.S. and China, Xanadu’s volatile post-SPAC quantum stock run, SpaceX’s reported Cursor acquisition talks, Meta’s 8,000-person AI-driven workforce reduction, and Thoma Bravo’s massive Medallia equity wipeout. From sovereign wealth and AI infrastructure to quantum financing and private equity pain, this episode asks the real question: can Canada build the capital systems needed to own its future? Canada Strong Fund: Carney’s $25B sovereign wealth fund announcement (00:31) Matt opens the episode by laying out the breaking news: Mark Carney has launched the proposed Canada Strong Fund, a $25 billion sovereign wealth fund aimed at giving Canadians a stake in strategic national projects and critical industries. Why John Ruffolo says Canada is dangerously undercapitalized (01:22) John argues that Canada’s core economic problem is not a lack of ideas, talent, or companies, but a lack of domestic capital formation. He explains why foreign-controlled capital in sovereign industries is a bad idea and why Canada needs its own funding mechanism. The biggest risk: governance or political slush fund? (03:14) John explains that the Canada Strong Fund will only work if it is independently governed, similar to CPPIB or CDPQ. Without strong governance, he warns, the fund could collapse into politically motivated pet projects. Can Canada borrow at 3.5% and earn 7% long term? (04:59) John breaks down the financial logic behind using Canada’s strong credit rating to borrow at lower rates and invest through a professionally managed fund targeting long-term returns similar to major pension funds. Why the fund fails if returns do not materialize (08:15) Matt raises concerns about launching a sovereign wealth fund during a deficit environment. John says the idea only works if the fund is independently managed and capable of generating real long-term returns. No more grants: John’s blunt plan for government funding (14:02) John calls for Canada to stop giving grants, especially to foreign-based companies, and instead convert government support into equity investments that create long-term ownership and capital recycling for the country. Cohere acquires Aleph Alpha and makes a sovereign AI play (16:12) Matt breaks down Cohere’s acquisition of German AI firm Aleph Alpha, the new Berlin European headquarters, and the reported $600 million financing commitment from Schwarz Group as part of a broader sovereign AI strategy. Xanadu’s quantum stock surge and post-SPAC volatility (19:59) Matt explains Xanadu’s post-SPAC trading action, including its sharp rise, options activity, and SEC filing registering nearly 300 million Class B shares for sale after the lockup period expires. SpaceX, Cursor, and peak AI paper-deal froth (24:25) Matt and John react to reports that SpaceX could acquire AI coding startup Cursor for $60 billion, with John arguing that SpaceX shareholders should be furious about the growing complexity and governance concerns. Meta layoffs and the real cost of AI capital spending (27:56) Matt highlights Meta’s reported 10% workforce reduction tied to massive AI capital spending. John argues the “AI efficiency” explanation often masks bad capital allocation and failed strategic bets. Thoma Bravo’s $5.1B Medallia equity wipeout (29:55) The episode closes with Thoma Bravo handing Medallia back to creditors after a major private equity software deal collapses, raising questions about SaaS valuations, debt structures, and exit assumptions in the AI era. 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

    33 min
  3. How to Get VC Funding in 2026 with Matt Cohen

    APR 23

    How to Get VC Funding in 2026 with Matt Cohen

    Originally recorded as Matt Cohen’s guest appearance on Mantle Mondays hosted by Amar Varma. In this special episode of Tank Talks, Matt Cohen joins Amar Varma on Mantle Mondays for a candid conversation about how to get VC funding in 2026, what early-stage investors actually look for, and where the next wave of breakout startups is being built. As the Founder and Managing Partner of Ripple Ventures, Matt shares his path from RBC trading desks and public markets to startup operating experience, angel investing, and eventually building one of Canada’s most active early-stage venture firms. He breaks down how founders can stand out in a crowded market, why validated problems and technical execution matter more than hype, and what separates companies that can raise from companies that get left behind. The conversation also dives into how Matt evaluates founders before product-market fit, why recruiting ability and fundraising skill matter as much as product vision, and how AI, deep tech, biotech, aerospace, and software-enabled physical systems are reshaping venture capital. Matt also opens up about Ripple Ventures’ own evolution, the firm’s investment philosophy, and how Ripple OS and internal AI agents are helping portfolio companies move faster. If you want an honest look at startup fundraising, venture capital in Canada, founder-investor fit, AI startup differentiation, and the future of early-stage tech, this Tank Talks episode, originally recorded as Matt Cohen’s appearance on Mantle Mondays with Amar Varma, is packed with practical insights. How Turnstile Pulled Matt Into the Startup World (03:07) The origin story of Turnstile, the wifi marketing and analytics company Matt co-founded, and how building and exiting that business gave him his first real startup education. Why Startup Struggle Matters More Than Investor Talk (05:11) Matt gets real about how hard it was to raise capital, why Turnstile had to grind toward profitability, and why lived operator experience matters when founders pick investors. How Ripple Ventures Started Before the Fund Existed (07:42) Matt explains how he built the Ripple brand before institutional capital was in place, why perception matters in venture, and how his early angel wins created momentum with family offices. The Long-Game Philosophy Behind Fund I (10:51) A great story about raising a first fund, proving commitment to LPs, and why first-time managers need to stop waiting for the “perfect” close and just get moving. What Gets a Founder’s Attention in 2026 (16:44) Matt breaks down what’s changed in venture, why deep tech and frontier ideas are more investable today, and why ambitious founders are tackling much bigger problems than they were a decade ago. The 4 Things Ripple Ventures Looks For in Founders (19:25) Matt lays out Ripple’s core framework: validated problem, technical founding team, recruiting ability, and fundraising skill. The Startup That Blew Matt Away (23:29) Matt shares the story of Clover and why seeing a young team scale to massive early traction changed how he thinks about speed, execution, and modern company building. What a Generational Company Actually Looks Like (33:59) Matt gets honest about what he can and can’t claim to know, then shares the founder traits he believes matter most when building something truly enduring. What Founders Should Look For in an Investor (38:05) A powerful section on support during hard moments, reputation in venture, and why investors are really tested when a company is struggling, selling, or stuck. Tank Talks, Community, and Playing the 25-Year Game (44:24) Matt reflects on building Tank Talks, surrounding himself with younger talent, and why staying close to ambitious founders keeps him sharp. Matt’s Best Advice for Founders and Builders (46:31) A strong closing section on paying it forward, reputation, and why the people you meet on the way up are the same people you’ll see on the way down. Mantle Mondays on YouTube: https://www.youtube.com/@withmantle Connect with Amar Varma on LinkedIn: https://www.linkedin.com/in/amar-varma-8041b9/ 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

    51 min
  4. The Rundown 4/15/26: Canada’s AI Crackdown, the Exit Tax Backlash, Cohere’s Germany Deal, and Hootsuite’s Reset

    APR 15

    The Rundown 4/15/26: Canada’s AI Crackdown, the Exit Tax Backlash, Cohere’s Germany Deal, and Hootsuite’s Reset

    In this episode of Tank Talks, Matt Cohen and John Ruffolo break down the latest developments shaping Canada’s tech landscape, from AI policy and government regulation to talent flight and emerging cybersecurity risks. They discuss proposals to restrict AI chatbot access for minors, the broader implications of tech regulation in a fast-moving market, and the controversial idea of imposing an exit tax on Canadians who leave for the U.S. for work. The conversation then turns to the next wave of AI competition and enterprise transformation. Matt and John unpack Cohere’s reported talks to merge with a German AI company as part of a broader push around sovereign AI, data infrastructure, and enterprise model deployment in Europe. They also debate Anthropic’s Claude Mythos preview and whether its reported ability to uncover zero-day vulnerabilities represents a real cybersecurity breakthrough or clever marketing. From there, they explore the rise of agentic AI inside large enterprises, where token allocation, workflow automation, and AI agents are becoming real boardroom priorities. The episode closes with Hootsuite founder Ryan Holmes returning as interim CEO, prompting a broader discussion about founder-led turnarounds, SaaS disruption, and how AI is reshaping leadership across the tech sector. Tune in for a sharp breakdown of the policy decisions, market shifts, and AI developments that could have a lasting impact on Canada’s innovation economy. The Blanket AI Ban Proposal for Youth in Canada (00:57) John and Matt debate the implications of a blanket ban on AI chatbots for individuals under 16 in Canada, exploring how this could hinder youth innovation and global competitiveness, especially when countries like China are advancing rapidly in AI development. Balancing AI Privacy Concerns with Innovation (01:39) John shares his thoughts on the growing debate around AI privacy laws and whether Canada should follow the EU’s model of regulation or take a more pragmatic approach. The conversation touches on the risks of banning AI technologies without considering the broader impacts on tech development. Patrick Bette’s Proposal for Exit Tax on Canadians Moving to the U.S. (04:56) Matt and John discuss the controversial proposal from Patrick Bette to charge an exit tax on Canadians who leave for the U.S. to work, aiming to recover the public investment in their education. They debate whether this idea is practical and whether it reflects a misunderstanding of the challenges facing Canada’s youth. Cohere’s Strategic Merger with German AI Player (11:12) Matt and John talk about Cohere’s potential merger with a German AI company and its implications for Canada’s AI sovereignty. John examines the strategic motivations behind this move and whether this type of cross-border alliance could position Canada as a leader in AI innovation. AI’s Role in the Corporate World: From Job Replacements to New Capabilities (19:00) A major topic in the episode is how AI is shifting from being seen as a tool for job replacement to one that unlocks new capabilities in various industries, including healthcare, banking, and retail. John and Matt delve into the emerging concept of internal AI agents and the complexities of managing compute resources in organizations. Hootsuite’s CEO Shake-Up: Ryan Holmes Returns (21:56) The episode wraps up with a discussion on Hootsuite’s recent leadership change, where founder Ryan Holmes returns to the helm as interim CEO. Matt and John explore the implications of this shift, especially in the context of the current AI-driven market disruptions. 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

    26 min
  5. Demystifying Venture Debt: Funding Growth with Less Dilution with Marshall Hawks

    APR 9

    Demystifying Venture Debt: Funding Growth with Less Dilution with Marshall Hawks

    Venture debt might be the most misunderstood tool in startup finance. Ask ten founders to explain it, and you will get ten different answers, most of them wrong. In this episode of Tank Talks, Matt Cohen sits down with Marshall Hawks, a 16-year Silicon Valley Bank veteran who structured hundreds of venture debt deals, including for Airbnb, Twitch, and Fitbit. After SVB’s collapse in 2023, Marshall stepped away to write the playbook founders had been missing: Venture Debt Deals: How to Fund Growth with Less Dilution. He breaks down what is actually happening in the 2026 venture debt market, including bigger facilities, new players in private credit, and what terms really look like today. They also get into when debt actually makes sense and when it does not, the biggest mistakes founders make on term sheets, and why the right lending partner matters more than squeezing out the lowest rate. If you want to grow faster without giving up more equity, or just understand how the full capital stack really works, this one is worth your time. Marshall’s Early Lessons in Finance and Entrepreneurship (02:30) * Learning secured lending basics in his grandfather’s Arkansas pawn shop * Reading people, judging value, and knowing what you don’t know, including the cubic zirconia story * Growing up with a venture-backed CEO father who later became a VC, building empathy for founders Life at SVB and the 2023 Collapse (08:24) * 16+ years, nine roles, including helping build SVB Canada * Inside the third-largest bank failure in U.S. history * The power of simply answering the phone during a crisis Venture Debt vs. Private Credit (15:58) * The key differences: venture banking (customer acquisition model) vs. private credit (deployed capital seeking returns) * Why banks offer smaller deals tied to revenue multiples, while private credit writes $50M–$150M+ checks * The role of warrants (equity kickers) in almost every venture debt deal What Lenders Actually Underwrite (20:58) * Why the cap table and investor syndicate matter more than financial models (models are always wrong) * How lenders assess whether a company can raise its next equity round Key Case Studies and Lessons (23:53) * Airbnb: The energy you could feel walking into the office * Subtle signals Marshall looks for: office vibe, founder energy, and the “Airbnb Rhode Island office” effect Clearco: A Cautionary Tale (28:03) * How Clearco used venture debt to scale rapidly and how over-leveraging nearly broke the company * The surprising role SVB’s own failure played in saving Clearco * Why revenue-based financing models can become burdensome when revenue becomes less predictable The State of the Venture Debt Market in 2026 (35:30) * Recorded $62 billion in volumes, recovered faster than expected * More choices than ever, including Stifel, HSBC, J.P. Morgan, BlackRock, Apollo, KKR, and Blue Owl * AI companies largely do not need debt right now Breaking Down Venture Debt Term Sheets for Founders (40:47) * Founders do not understand what motivates venture banks vs. private credit firms * Getting the right partner trumps any term sheet detail * Price and economics matter, but choosing the wrong lender is a disaster * The right lender can be meaningfully impactful as a company ramps up * Most founders think about terms first. They should think about their partner first. When to Start Building Lender Relationships (47:05) * It’s never too early, meet lenders 6–12 months before you need capital * Most venture debt deals happen after an equity round closes (serial, not parallel) * Send regular updates to lenders just like you would to investors Hybrid Rounds: Will Venture Debt and Equity Merge? (49:37) * Traditional SaaS players are stuck. They need to incorporate AI to survive. * Inside rounds with debt and equity stapled together feel like bridge rounds to buy time. * Marshall’s view: this will not become the norm. * Timing is wonky. Getting equity investors and lenders to work together is cumbersome. * Separate events work better: raise equity first, then raise debt. Marshall’s Closing Advice for First-Time Founders (51:22) * Treat venture debt as a tool, not a silver bullet * Prioritize finding the right long-term partner over optimizing every last term About Marshall Hawks Marshall Hawks spent 16 years at Silicon Valley Bank, where he originated and closed hundreds of venture debt deals with companies like Airbnb, Twitch, and Fitbit. Following SVB’s collapse in 2023, he left banking to write Venture Debt Deals: How to Fund Growth with Less Dilution, the practical guide he wished every founder had before opening a term sheet. He now serves as an independent voice on venture debt, helping founders navigate the post-SVB landscape of banks, private credit, and alternative financing. Connect with Marshall Hawks on LinkedIn: https://www.linkedin.com/in/marshallhawks/ Buy Venture Debt Deals: https://www.amazon.com/Venture-Debt-Deals-Growth-Dilution/dp/B0FZYQ53MW 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

    1 hr
  6. What Makes a Startup “Click”, Before it Even Exists? with Matt Cohen

    APR 2

    What Makes a Startup “Click”, Before it Even Exists? with Matt Cohen

    Originally recorded as Matt Cohen’s guest appearance on the Make It Click podcast hosted by Willson Cross. Matt Cohen joins Willson Cross on the Make It Click podcast for a sharp, no-fluff conversation on what actually makes early-stage startups click. As the founder and managing partner of Ripple Ventures, Matt breaks down how he went from Bay Street and Wall Street trading desks to becoming one of Canada’s most active early-stage investors, backing founders at the inception stage, sometimes before incorporation, bank accounts, or even customers exist. Matt shares the real frameworks he uses to evaluate founders before product-market fit: team quality, problem validation, recruiting ability, and fundraising muscle. The conversation dives into how Ripple Ventures helps companies graduate from pre-seed to Series A, why Matt loves pivots (or “evolutions”), how Canadian founders differ from U.S. founders in ambition and risk tolerance, and why AI, deep tech, space tech, and defence are reshaping venture capital in Canada. If you’re a founder thinking about taking the leap, or an investor trying to understand the next wave of Canadian innovation, this episode is packed with practical, brutally honest insight. Matt Cohen’s Unconventional Path Into VC (02:07) From trading on Bay Street and Wall Street during the financial crisis to angel investing after the Turnstile exit, and eventually launching Ripple Ventures. How early wins in angel investing attracted Toronto family offices and became the foundation for Fund I. How Ripple Ventures Was Born Before the Fund Existed (06:04) Why Matt created the Ripple Ventures brand before raising institutional capital, how reputation compounded deal flow, and the early angel investments that became proof points for LPs. The Ripple Ventures Framework: The 4 Things Matt Looks For (16:46) The four-part founder filter: team, problem, recruiting, and raising capital. Why most inception-stage companies don’t need customers yet, and what really matters before the first pilot. The Ideal Founding Team Structure in 2026 (20:56) Why two to three founders is the sweet spot, what breaks when there are four or five, and how AI-native companies are changing the ideal division of roles between technical, research, and business founders. Why Matt Loves Pivots (and Hates the Word Pivot) (24:48) A fascinating story of a database company evolving into consumer healthcare, plus the decision framework Matt uses to pressure-test major product or market changes. Why Canada’s Founder Quality Is Rising Fast (34:18) Matt’s most bullish view yet on Canadian founders, the Build Canada momentum, Shopify and AI spinouts, and why technical founders from Vector, Mila, and DeepMind alumni networks are creating a new wave. The Biggest Difference Between Canadian and U.S. Founders (41:34) A brutally honest comparison around ambition, downside protection, and why U.S. founders often optimize for upside while Canadian capital historically optimized for risk management. The Brutal Truth Every Founder Needs to Hear (48:25) Matt’s best founder advice: don’t believe your own BS, prepare for everything to go wrong, and understand the life cost of building a venture-scale company before you start. Ripple Ventures’ New Startup Studio Thesis (55:20) Matt reveals how Ripple Ventures is evolving from fund + fellowship into a studio model, using AI agents and internal problem discovery to build products before bringing in founding teams. Listen to the Make It Click podcast: https://www.youtube.com/@hireborderless Connect with Willson Cross on LinkedIn: https://www.linkedin.com/in/willsoncross/ 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

    59 min
  7. The Rundown 3/30/26: Ontario’s $4B AI Fund, SpaceX’s IPO, and Why Claude Is Winning Enterprise

    MAR 30

    The Rundown 3/30/26: Ontario’s $4B AI Fund, SpaceX’s IPO, and Why Claude Is Winning Enterprise

    In this episode of Tank Talks, Matt Cohen and John Ruffolo unpack a major week across Canadian venture capital, deep tech liquidity, sovereign investment strategy, and the rapidly shifting AI software stack. The conversation opens with Ontario’s newly announced $4 billion Protect Ontario Account investment fund, designed to back artificial intelligence, defence, manufacturing, and growth-stage businesses while shielding jobs from trade disruption. John breaks down the real strategic question beneath the headline: whether Ontario should centralize capital with one fund manager or use a multi-manager, co-investment model that mirrors the Canada Growth Fund and Quebec’s long-standing institutional playbook. The episode then shifts into a stacked run of liquidity events reshaping tech markets. Xanadu’s public debut becomes a lens into Canada’s capital formation challenges, while the looming SpaceX IPO raises bigger questions about how billions in founder and employee liquidity could flood back into deep tech, defence, and space infrastructure. The discussion sharpens further with CoolIT Systems’ $4.75B acquisition by Ecolab, a staggering private equity outcome fueled by AI data center demand, before closing on a real-time operating lesson from inside the Tank Talks fund: why Claude has overtaken OpenAI for enterprise workflows, coding agents, and operational leverage. From sovereign capital to AI agents, the throughline is clear: infrastructure, liquidity, and execution are redefining where value compounds. Ontario’s $4B Protect Ontario Fund & the Single-Manager Debate (00:44) Ontario unveils a $4 billion investment vehicle targeting AI, defence, manufacturing, and job protection. Matt and John unpack whether concentrating capital under one GP creates governance risk or strategic efficiency. Why Ontario Is Finally Playing Offense in Capital Formation (02:06) John explains why Ontario’s vulnerability to trade shocks and weak co-investment capacity made this move overdue, especially compared to Quebec’s institutional investing model. Xanadu Goes Public: A Canadian Deep Tech Financing Milestone (05:33) Xanadu begins trading on both TSX and Nasdaq, giving Canadian deep tech founders a new case study in alternative financing structures through SPACs. SpaceX’s IPO Could Trigger a Deep Tech Liquidity Supercycle (09:12) SpaceX’s rumored IPO filing and potential $1.75T valuation spark a discussion about how recycled liquidity may turbocharge space, defence, and physical AI startups. CoolIT’s $4.75B Exit & the AI Infrastructure Gold Rush (12:14) CoolIT Systems’ sale to Ecolab highlights how AI data center infrastructure is driving some of the fastest PE returns in Canadian tech history. The 15x Private Equity Return Nobody Saw Coming (13:17) KKR’s three-year hold turns into a stunning 15x equity return, proving that “feature businesses” can become platform-scale winners when AI demand rewrites infrastructure economics. Why Claude Is Beating OpenAI in Enterprise Workflows (15:32) Matt breaks down how Claude-powered agents now run finance audits, subscription cleanup, workflow automation, and internal ops, saving real dollars and flipping AI usage across the portfolio. Consumer AI vs Enterprise AI: The Real Claude vs OpenAI Story (18:20) The closing thesis: OpenAI may dominate consumer mindshare, but Claude is winning where workflows, coding, and high-value enterprise execution matter most. 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

    20 min
  8. Canada’s $35 Billion Arctic Push, the New Cost of War, and Building Sovereign Capability with Glenn Cowan of ONE9

    MAR 26

    Canada’s $35 Billion Arctic Push, the New Cost of War, and Building Sovereign Capability with Glenn Cowan of ONE9

    In this episode of Tank Talks, host Matt Cohen sits down with Glenn Cowan, a former Canadian Special Forces squadron commander, world-record skydiver, and founder of ONE9 Investments, one of Canada’s most focused venture firms in defence, national security, and dual-use tech. He has experienced both sides of the mission, from the field to the boardroom, and brings a perspective you do not hear often when it comes to building serious, sovereign technology in 2026. Glenn opens up about his unexpected shift from military operations into venture capital and what he is seeing firsthand as Canada’s defence landscape rapidly evolves. He breaks down major moves like the federal government’s $35 billion Arctic defence infrastructure push and BDC’s expanded $6 billion defence platform, translating what those headlines actually mean for founders, investors, and the country’s long-term capability. The conversation also digs into bigger questions, including how Canada balances sovereignty with working alongside allies, why the Arctic is becoming strategically critical, and how venture capital is stepping in as a real force in national security. If you are building in defence tech, investing in dual-use innovation, or simply trying to make sense of where Canada is heading globally, this episode offers a grounded, no-nonsense look at what is happening and what it takes to be part of it. Glenn’s Unconventional Path to Venture Capital (01:48) * From infantry officer to JTF2 squadron commander * How 20 years in special operations shaped his investment philosophy * The “wrong end of the trade” moment that led to founding ONE9 The Shift in Canada’s Defence Landscape (05:37) * Why Canada is moving from the “kids’ table” to a relevant middle power * The $35 billion Arctic defence infrastructure announcement * How venture capital is becoming a tool of national security Public-Private Partnerships in Defence (08:37) * Why government end users are no longer the sole owners of critical capability * The democratization of space, surveillance, and intelligence * How founders and VCs can partner with end users to build faster The Future of Conflict: Cost Asymmetry and Contested Domains (21:52) * How $500,000 in drones can destroy $7 billion in strategic bombers * The rise of lasers, kinetic interceptors, and counter-drone technology * Space as a warfighting domain and what happens when Starlink goes down Sovereignty vs. Interoperability (26:55) * What it means for a defence company to be truly Canadian * IP residency, data governance, and Canadian capital stacks * Why Canada needs its own defence primes, not just multinational subsidiaries The Arctic as a Front Line (31:05) * Why the Northwest Passage and critical minerals are strategic flashpoints * Russian and Chinese activity in Canada’s North * Building the first Inuit-led defence company and the importance of local partnership ONE9’s Evolution and the Kensington Partnership (40:57) * Why ONE9 joined forces with Kensington Capital and AGF * Scaling a defence-focused investment platform with institutional backing * What’s next for Canada’s most specialized defence tech fund About Glenn Cowan Glenn Cowan is a former Canadian Special Forces squadron commander, world-record skydiver, and founder of ONE9 Investments, a venture firm focused on defence, national security, and dual-use technology. A 20-year veteran of the Canadian Armed Forces, Glenn spent over a decade conducting strategic missions on behalf of the Government of Canada. He now applies his operational expertise to early-stage investing, backing founders building critical capabilities in autonomy, space, intelligence, and Arctic security. Glenn is also a co-founder of the first Inuit-led defence company and holds multiple world records for skydiving on all seven continents. Connect with Glenn Cowan on LinkedIn: https://www.linkedin.com/in/glenn-cowan-3387b656/ Learn more about ONE9 Investments: https://www.one9.ca/ 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

    54 min
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5
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29 Ratings

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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.com

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