Tank Talks By Ripple Ventures

Ripple Ventures

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. 21h ago

    Claude, GPT or DeepSeek? The Data Behind the Race | Peter Walker

    In this episode of Tank Talks, host Matt Cohen welcomes back Peter Walker, Head of Insights at OpenRouter and formerly of Carta, where his charts on cap tables and fundraising became required reading for founders and VCs. Peter now sits on one of the largest real-world data sets in AI, with roughly 600 trillion tokens a month flowing through a single API that gives access to 500+ models. He explains why OpenRouter is as much about routing between inference providers as between models, and why the same model can feel brilliant or terrible depending on who serves you the token. They also dig into how fast the market has splintered beyond Claude and GPT, why agentic usage was the turning point, and why most teams don’t need the most expensive token for every task. Peter shares his view on open-weight models and the geopolitics behind them, why the AI “bubble” looks different from the dot-com fiber glut, and what stood out to him in Anthropic’s S1, from the non-cancellable compute commitments to the eye-popping growth and net dollar retention. He also covers neo-clouds, fine-tuning versus distillation, why he thinks “model nerfing” is a red herring, and why cultural change, not technology, will slow AI’s spread through the broader economy. Whether you’re building on top of the AI stack, funding it, or just trying to make sense of it, this conversation offers a data-driven view from someone who watches the whole market. From Carta to OpenRouter (03:02) * Peter’s path from a data-visualization nerd at Carta to head of insights at OpenRouter * Why he wanted to get closer to AI, and the FOMO that pulled him there * Why OpenRouter’s cross-lab view is unique: labs only see their own data, while OpenRouter sees which models, tasks, and providers are gaining traction * Joining 10 days before the Stripe acquisition was announced What OpenRouter Actually Does (04:50) * One API key for 500+ models, instead of being “a Claude shop” or “an OpenAI shop” * Why the more important layer is inference provider routing: the same open-weight model can be served by hundreds of providers with very different cost, latency, throughput, and reliability * The marketplace model: more models attract more users, which attract more providers, with a service fee on top * The founding team’s commitment to making as much data public as possible * Why Stripe and OpenRouter fit: both abstract complexity (payments and AI), and AI is now the first or second fastest-growing line item for CFOs Fragmentation and the Agentic Turning Point (10:00) * Why the market is still in early innings, from ChatGPT’s launch in late 2022 to today’s diversity of models * The shift in February 2026 from chatting with AI to agents doing the work, and why it kicked off multi-model usage * Matching models to tasks: security reviews, customer service, and why you may not need a frontier model to review your next email * Why this market, with commodity-like supply and complex demand, has no real precedent Bad Tokens, Good Tokens (12:54) * Why the inference layer is more complex than the model layer * Closed models are served by a handful of places, while open models have hundreds of providers, some excellent and some “super shady” * Speed differences of up to 20x between providers serving the same model * Why people disagree so much about the same model: often it’s the token they were served, not the model * The reputational risk of putting a slow or unreliable provider behind a customer-facing app Subscriptions vs. API Pricing (15:35) * A carnival-token analogy for how tokens work * Why $100-a-month subscriptions are still fantastic deals, and why API bills can become “eye-watering” * Why the best models are still worth it for many use cases, but not for all of them * The geopolitical layer: open-weight models skew Chinese, closed-weight models skew American Open Weights vs. the Frontier (18:41) * Why OpenRouter believes in a multiplicity of winners rather than one open-or-closed champion * New model categories nobody had envisioned weeks ago, such as fast, cheap decision models for classification * Why not everything will happen inside OpenAI or Anthropic Is AI a Bubble? (21:42) * Why this isn’t the dot-com fiber glut: everyone is compute constrained, and more GPUs would be used * How supply and demand can still get out of whack * Why there’s no world where we go back to a pre-AI economy Reading Anthropic’s S1 (22:37) * The scale of the multi-year, largely non-cancellable compute commitments * Why Peter sees Anthropic as highly profitable on inference, with the open question being whether it can fulfill its commitments * 14x growth last year from a base of roughly $780 million, at a company only three years old * The reported 900% net dollar retention, and why it’s remarkable even if it doesn’t repeat * Why using more Anthropic and adding open-weight models to the portfolio aren’t mutually exclusive Neo-Clouds and the GPU Gold Rush (26:24) * Where the next token gets served from when most of Anthropic’s compute is with the hyperscalers * 50+ inference providers apply to join OpenRouter each week, and very few are accepted * What a neo-cloud really is: capital-intensive GPU access plus software that runs models faster and more reliably * Why it’s hard: capital markets, energy supply, infrastructure teams, 100% uptime, and deal-making skills that SaaS never needed * Neo-labs vs. neo-clouds, and why many labs will transition into clouds Fine-Tuning, Distillation, and Model “Nerfing” (31:38) * Fine-tuning: how legal AI companies turn a strong base model plus proprietary data into a specialized product * Distillation: why closed labs forbid it, why the open-weight rules are murkier, and how labs distill their own models into new variants * Why “model degradation” is a red herring: slower or less reliable tokens at the inference layer and the self-cannibalizing release cycle are more likely explanations Models vs. Harnesses (36:00) * How much product and harness matter now that raw intelligence is less differentiating for some use cases * Why Peter thinks model intelligence still matters most for the top labs, and the product is everything for application-layer companies * Personal agents as the first time many people experience powerful AI without knowing which model is behind it The Cultural Gap in AI Adoption (40:56) * Why the biggest divide is generational, including the age of the company * Why diffusion beyond San Francisco and New York will likely disappoint, because it’s a person-to-person problem, not a technological one * How doom-and-gloom messaging causes people to disengage * Why everyone now has “the smartest EA in the world” in their pocket Grieving What You Were Great At (45:49) * Peter’s own experience letting AI build the charts he spent a decade mastering * Accepting the inevitability of the change and moving your expertise to the strategic layer: asking the right questions and providing the right framing * Finding new things to do that the technology enables rather than removes About Peter Walker Peter Walker is Head of Insights at OpenRouter, where he analyzes usage data across hundreds of models and inference providers. Previously, he spent five years at Carta turning cap table, valuation, and fundraising data into widely read charts and research. Connect with Peter Walker: https://www.linkedin.com/in/peterjameswalker Visit the OpenRouter website: https://openrouter.ai/ 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

    Claude, GPT or DeepSeek? The Data Behind the Race | Peter Walker
  2. 6d ago

    The Rundown 10/30/26: Anthropic’s IPO Debate, Canada’s Venture Funding Push & Rising Cyber Risks

    Welcome back to another news roundup on Tank Talks: The Rundown! Matt Cohen and John Ruffolo dig into a question connecting Canadian venture capital, AI infrastructure, and cybersecurity: what does it actually take to sustain the growth everyone is betting on? From Ottawa’s $1.75 billion venture and growth capital plan to the Anthropic IPO numbers discussed in the episode, they look at where fresh capital could make a difference and where financial commitments could become a problem. For Canadian founders, there’s reason for optimism. For investors chasing the AI boom, John has some pointed questions about cash flow, compute costs, and what happens when growth slows. For founders, investors, and business leaders, this episode connects the funding announcements and AI headlines to the decisions that follow. Where will the money come from, what will it build, and how resilient will those businesses be when conditions change? Canada’s $1.75B Venture Capital Push: When Will the Money Arrive? (00:37) Ottawa’s venture and growth capital plan leads the discussion, with funding earmarked for fund of funds, life sciences investors, emerging managers, and companies trying to scale in Canada. Matt and John unpack how the programs could attract pension funds and other institutional investors. They also tackle the practical question behind the announcement: how quickly can fund managers turn those commitments into capital that founders can actually use? Why Canadian Startups Keep Selling Before They Scale (06:12) A promising startup gets traction, attracts a buyer, and sells. Early investors may earn a strong return, but Canada loses another opportunity to build a lasting global company. Matt shares that his firm has already seen three exits from its 2023 vintage fund. That opens a bigger conversation about the shortage of domestic growth capital, especially for companies raising Series C rounds and beyond. Can the new funding help founders keep building here? Canada’s Budget: The Tax Changes John Wants to See (09:03) Ahead of the federal budget, Matt and John discuss what would make a difference for the innovation economy. Incentives for major infrastructure projects have their place, but software companies, startup employees, and early investors face different decisions. The conversation turns to a Canadian approach inspired by U.S. Qualified Small Business Stock rules, commonly known as QSBS, and the potential for broader capital gains exemptions. Anthropic’s IPO Debate: Huge Growth, Huge Compute Commitments (11:06) Matt walks through the Anthropic filing figures discussed in the episode, highlighting rapid revenue growth, enterprise adoption, and substantial compute commitments. John focuses on the relationship between those obligations and the revenue needed to support them. His comparison is WeWork’s financial structure: long-term commitments supported by revenue that could change much faster. The question is how that structure holds up if demand disappoints. CoreWeave, Oracle & the Risk of an AI Infrastructure Squeeze (18:11) The discussion expands to the companies supplying AI’s computing power. Matt raises Elon Musk’s comments about financing pressure on AI infrastructure providers, while John examines how interconnected contracts and circular financing could spread financial stress. If a major provider runs into trouble, how many other businesses are exposed? Cybersecurity, Sovereign AI & the Risks of AI Agents (21:02) Matt and John close with cybersecurity and the growing consequences of giving AI systems access to business tools and sensitive information. They discuss sovereign AI, aging digital infrastructure, and the additional exposure that comes with increasingly capable AI agents. For businesses adopting these tools, security decisions are becoming inseparable from operational decisions. 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

    The Rundown 10/30/26: Anthropic’s IPO Debate, Canada’s Venture Funding Push & Rising Cyber Risks
  3. Oct 29

    How Amazon’s “Best Vendor” Grew 8x | Mike Mahannah

    In this episode of Tank Talks, host Matt Cohen sits down with Mike Mahannah, partner and advisor at Resonance Consulting, to unpack nearly 40 years of building businesses in Western Canada. Mike shares his path from a prairie upbringing and an engineering degree to becoming a partner at Olympic International in Vancouver, a five-person HVAC sales agency above a fish plant that grew into the market leader. He walks through the 10-year internal succession plan he used to sell the company to its employees, and the hard lesson he learned when a formula-based valuation failed in a downturn. They also dig into the second chapter of Mike’s story: buying Scott Springfield, a Calgary sheet metal job shop, for $1 million in 1990 and turning it into a custom air handling manufacturer. After landing Amazon Web Services as a customer, it grew from $20 million to $160 million in revenue in four years and sold to Modine for $260 million (about 10.5x trailing 12-month EBITDA). Mike explains how he earned a trusted-partner relationship with Amazon, why he sold a future instead of a past, and how he built a culture where mistakes are shared, celebrated, and learned from. He also opens up about straight talk in coaching, his biggest blind spot (firing too slowly), and why planning your exit is the thing most owners get wrong. Whether you’re a founder thinking about succession or an exit, an operator chasing enterprise contracts, or a leader trying to build a healthier culture, this conversation is full of practical lessons from someone who has done it twice. From Prairie Boy to Partner at Olympic International (01:00) * Growing up in Alberta, the oil patch, and the pull toward engineering * Moving to Vancouver in 1978 and joining Olympic International in 1985 as the sixth person at the firm * A small HVAC sales agency selling to pulp mills, mines, hospitals, and large office buildings * Why he bought in for the partners and the relationship, not just the business * Early lessons: grunt work, technical credibility, and hiring people who are both competent and a good fit * Growing the firm to 80 people by his exit, and 115 and counting today The 10-Year Succession Plan: Selling to Your Employees (05:09) * Why a sales agency can’t be sold to private equity: if the salespeople leave, there’s nothing left * Selling equity in 5% increments to key employees, many of whom took second mortgages to buy in * Why “a path to ownership” became a powerful pitch for attracting top talent * Why most owners never plan their exit, and why many cling to 51% for control * The “secret sauce”: using the shareholders’ agreement to keep influence over the board while reducing his stake, until the company could buy him out of its own cash * Planning to keep enough cash in the business for the buyback Valuation Lessons and the Culture Reset (09:46) * Why a formula-based valuation backfired: it grossly undervalued the business in a downturn * Moving to a professional valuator, used only when a transaction is pending * Why Mike wouldn’t change anything about how he executed the succession * The culture reset 15–20 years in: strategies kept failing because the culture wasn’t pulling in the same direction * The three pillars of the culture: win-win-win, communication, and integrity * Why choosing a culture attracts some people and ejects others Buying Scott Springfield for $1 Million (14:00) * Acquiring a Calgary sheet metal job shop in 1990 as a defensive move to get into custom air handling * Teaching them to build quality equipment, starting with a first unit for Lions Gate Hospital * Converting the business from a job shop to a custom air handling manufacturer Landing Amazon and the Data Center Boom (16:19) * Spending over a year proving quality and trust before the volume came * Funding a second plant with personal capital in 2015 after the original plant filled with one contract * Roughly $10 million per giga center order, and never missing a delivery date * The setback: the intermediary pulled out after the plant was built, leaving a new plant and no customer, at a cost of around $3 million * Turning that setback into a direct relationship with Amazon Playing the Long Game on Enterprise Contracts (19:46) * Three gates: engineering and quality control, the buyers, and the legal team * Why Amazon’s one-sided contracts were tolerable after three years of working together * Insisting on a partnership instead of a transactional relationship * Listening for what each stakeholder cares about, including internal politics, so they look good too Selling to Modine: Timing, Process, and Culture (23:28) * Growth from $20 million to $160 million in four years, and why a 12-month EBITDA multiple made sense * Selling the Amazon relationship as part of the asset, and how they handled customer concentration * Why now: the shareholders were at retirement age, and a third plant would have cost $15–20 million * Choosing Engel Advisors, a Detroit boutique, after interviewing seven M&A firms * Preferring an industry buyer over a financial one, and why Modine’s commitment to keep the culture and team won out * The call with Amazon and Modine, where Amazon said Scott Springfield was its best supplier * Mike’s advice: hire a good advisor and sell the future, not the past Never Waste a Mistake (30:28) * Why Mike treats every mistake as an ineffective action to examine, not a personal failing * How hidden mistakes were costing the company, and how he shifted the culture by sharing his own first * Putting $20 on the table for the juiciest mistake of the week * Why one mistake shared can educate 25 people * Where the line is: repeating the same mistake, or three strikes Straight Talk, Blind Spots, and Firing Faster (35:00) * Why Mike hired Resonance Consulting while he was still CEO * Coaching founders who hide behind their numbers * An example of two partners who didn’t realize they were talking down to their staff * Why people self-correct once they see their blind spot * Mike’s own recurring mistake: being too slow to fire, and what happened when he finally let his top two salespeople go Life After the Exit (40:24) * Why planning your transition out is the area where owners are weakest * Having a great life while building a business, instead of sacrificing it * Why retirement should be about staying on purpose, not putting your feet up About Mike Mahannah Mike Mahannah is a partner and advisor at Resonance Consulting, where he coaches founders and operators on leadership, culture, and succession. Previously, he was a partner at Olympic International, a Vancouver HVAC sales agency that grew to 80 employees under his ownership and is now the market leader, and owner and president of Scott Springfield, a custom air handling manufacturer with $160 million in revenue and 550 employees that he sold to Modine. He grew up in Alberta, studied engineering, and has lived in Vancouver since 1978. Connect with Mike Mahannah: linkedin.com/in/mike-mahannah Visit the Resonance Consulting website: https://resonanceconsultinginc.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

    How Amazon’s “Best Vendor” Grew 8x | Mike Mahannah
  4. Oct 23

    The Rundown 10/23/26: CoreWeave’s Debt Warning, Anthropic’s $2T IPO Bet & Elon Musk’s SpaceX Pledge

    AI demand is booming. So why is John Ruffolo watching the bond market? Welcome back to another news roundup on Tank Talks! Matt Cohen and John Ruffolo dig into the money behind the artificial intelligence boom, and whether the companies building it can make the numbers work. From Anthropic’s proposed $10 billion Nova Scotia data center campus to CoreWeave’s debt pressures and the race between OpenAI and Anthropic for investor capital, the conversation keeps coming back to one question: when does extraordinary growth turn into actual cash flow? They also unpack Anthropic’s public benefit fund proposal, Elon Musk’s SpaceX share pledge for American children, and what the Alberta referendum discussion reveals about Canada’s unresolved provincial tensions. For founders, investors, and anyone following Canadian business and AI infrastructure, this episode looks at the financial assumptions behind the headlines and what could happen when those assumptions meet reality. Anthropic’s $10 Billion Canada Bet: Who Funds the Build? (00:39) A massive AI infrastructure project in Cape Breton sounds like a win for Canada. Matt unpacks the Anthropic-EverWind data center deal discussed in the episode, including the proposed investment in computing infrastructure and wind power, the ownership behind the project, and its phased expansion plans. But announcing a campus and financing one are two very different milestones. With construction, power, and capital all needing to come together, how much of the headline will become operating capacity? CoreWeave’s Debt Problem: Is the Bond Market Sounding an Alarm? (03:19) Matt walks through the company’s stock decline, rising bond yields, and widening credit default swap spreads, the cost of protection against a borrower failing to pay. The bigger issue is a business model that requires enormous spending today against revenue expected tomorrow. Separating data centers into individual financing structures may reduce some risks, but it doesn’t eliminate expensive borrowing, power constraints, or execution problems. Anthropic’s IPO Ambitions: Incredible Growth, but Where’s the Cash? (09:16) Matt and John turn to Anthropic’s investor presentation and the roughly $2 trillion IPO valuation ambition discussed on the show. The revenue growth is extraordinary. Whether that growth justifies the price is a harder question. They examine compute costs, stock-based compensation, and the gap between adjusted profitability and cash generation. Matt also raises the question of how usage attributed to Chinese model developers could affect the revenue picture. OpenAI vs. Anthropic: Can Investors Fund Both? (12:20) What happens when two of AI’s biggest companies seek enormous amounts of money at roughly the same time? Matt compares the OpenAI fundraising plans and Anthropic IPO ambitions discussed in the episode. Different fundraising routes do not necessarily mean different sources of capital, especially when both companies are courting some of the world’s largest investors. Elon Musk’s SpaceX Share Pledge: A Generation of Shareholders? (14:36) Matt and John discuss Elon Musk’s stated plan to give a SpaceX share to every American child under 18 through Trump accounts. Matt estimates the potential value of the pledge while noting that timing and transfer details remain unresolved. The idea opens up a broader conversation about giving cash versus shares, tax considerations, and what happens when millions of children become shareholders in the same company. Alberta’s Referendum: Why the Ottawa Fight Isn’t Over (17:11) The episode closes with Matt and John discussing preliminary Alberta referendum results described during the recording, including the reported rejection of separation. John shifts attention to the other referendum questions and what they could mean for provincial powers, federal authority, and Alberta’s relationship with Ottawa. They also consider why Quebec’s economic circumstances make comparisons between the two provinces complicated. 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

    The Rundown 10/23/26: CoreWeave’s Debt Warning, Anthropic’s $2T IPO Bet & Elon Musk’s SpaceX Pledge
  5. Oct 22

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

    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 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 more scans to lawyers taking on longer-tail opportunities. * The potential for AI to compress time in healthcare, improving both patient outcomes and leisure time. About Shomik Ghosh Shomik Ghosh is a Partner at Sierra Ventures, a 45-year-old venture firm with a legacy of backing companies like Intuitive Surgical and Intuit. He focuses on early-stage investments in AI, frontier tech, hard tech, and deep tech. Prior to Sierra, Shomik was a Partner at Boldstart Ventures, where he helped build their inception-stage practice. He began his career in fixed income sales and trading before moving into investment banking and then venture capital. He holds a degree from Carnegie Mellon University. Connect with Shomik Ghosh: linkedin.com/in/shomik-ghosh-a5a71319Visit the Sierra Ventures website: https://www.sierraventures.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

    The "Prepared Mind" Investing Strategy Behind Sierra Ventures' Biggest Bets | Shomik Ghosh
  6. Oct 15

    Why Investors are Betting on Canadian Startups | NRTH Conference

    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 start Isaac 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 AI Elizabeth 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 month About Michael Garrity Michael 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 Souweine Isaac 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/en About Elizabeth Yin Elizabeth 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.vc Connect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1 Visit 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

    Why Investors are Betting on Canadian Startups | NRTH Conference
  7. Oct 8

    The Billable Hour is Broken: How Blackletter is Redesigning Law for Startups | Jonathan Rosenbluth (CEO and Co-Founder)

    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 something The 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 world Inside 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 background The 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 too A 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 incentives Why 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-day The 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 task Disrupting 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 retail Building in Canada and Looking Ahead (31:08) * Why Jonathan believes every Canadian founder has an obligation to build at home * Crediting Cohere’s founders for proving it’s possible * The biggest challenge as a first-time founder: prioritization amid constantly ratcheting intensity * The five-year vision: expert lawyers and purpose-built technology working in harmony for clients About Jonathan Rosenbluth Jonathan Rosenbluth is the CEO and co-founder of Blackletter, an AI-native law firm delivering top-tier legal services at a fraction of the cost. Previously, he was employee #20 at Cohere, where he helped scale the company from stealth to a $6.8 billion valuation, leading sales, partnerships, and business operations before transitioning to product. He holds a JD from Harvard Law School and a degree in history from Harvard University, and spent time at McKinsey & Company. Connect with Jonathan Rosenbluth: linkedin.com/in/rosenbluth Visit the Blackletter website: https://blackletterfirm.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

    The Billable Hour is Broken: How Blackletter is Redesigning Law for Startups | Jonathan Rosenbluth (CEO and Co-Founder)
  8. Sep 29

    The Rundown 9/29/26: Quantum Reality Check, AI Risks, and Why Canada Is Missing Its Tech Opportunity

    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/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

    The Rundown 9/29/26: Quantum Reality Check, AI Risks, and Why Canada Is Missing Its Tech Opportunity
5
out of 5
17 Ratings

About

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

You Might Also Like