Tank Talks By Ripple Ventures

Welcome back to another episode of Tank Talks! Host Matt Cohen is joined once again by John Ruffolo to dissect the major headlines shaping the tech and political landscapes. From Google’s surprising search decline to Alberta's political maneuvers and OpenAI's evolving partnership with Microsoft, this episode delivers in-depth analysis and thought-provoking insights.Alberta’s Exit Threat: Political Reality or Empty Rhetoric? (00:04:20)* In a passionate speech, Alberta Premier Danielle Smith called for significant changes, including scrapping Bill C-69 and easing pipeline restrictions. While her stance highlights Alberta’s grievances over federal policies, talk of a potential referendum on separation looms large.John’s take: Alberta’s frustrations are rooted in a decade of feeling undervalued, but the talk of separation could harm Canada’s stability on the global stage. Is this a legitimate political movement or a pressure tactic to get Ottawa’s attention?OpenAI’s Partnership Drama: Can Microsoft Keep Control? (00:09:36)* OpenAI’s revenue-sharing deal with Microsoft faces renegotiation, as the AI giant’s financial projections for 2030 are far lower than initially expected. With Microsoft holding critical infrastructure leverage, how will OpenAI balance growth aspirations with strategic partnerships?John’s take: The entry of a new executive at OpenAI may signal a strategic pivot as the organization navigates both its nonprofit roots and commercial ambitions.Apple vs. Google: The Browser Battle Intensifies (00:13:45)* Apple’s decision to challenge Google’s default search dominance has sent shockwaves through the tech world. As the DOJ moves to bar Google from maintaining exclusivity on third-party browsers, could this spark a major shift in browser market dynamics?John’s take: Apple’s track record with AI has been inconsistent, but disrupting Google’s foothold might be a game-changer in the long run.Is Google Losing Its Search Dominance? (00:15:09)* Google’s recent sell-off raised eyebrows, fueled by statements hinting at a decline in search usage. John Ruffolo dives into the implications of Google's search being “under attack” and the strategic shifts at play. Is the rise of AI-powered alternatives like ChatGPT fundamentally altering how people search for information?John’s take: Google’s maneuver might be an attempt to alleviate DOJ antitrust pressure. If Google’s dominance in search truly falters, what could this mean for the future of the tech giant?Education Disrupted: The AI Cheating Debate (00:16:52)* A viral article from New York Magazine claims students are increasingly using AI tools like ChatGPT to bypass traditional academic tasks. Is this cheating, or a natural evolution of how technology reshapes education?John’s take: Comparing the rise of AI tools to the introduction of calculators in schools, John questions whether the educational system needs a fundamental rethink to adapt to the digital age.Investing Evolution: CO2 Opens the Doors to Smaller Investors (00:19:27)* A new fund from CO2, backed by Bezos and Dell, allows investors to contribute as little as $50,000. Is this democratization of venture capital a positive trend, or a risky dilution of strategic investment?John’s take: This could signal a growing divide between massive investment conglomerates and boutique, specialized investors. Is the barbell approach to investment here to stay?Tune in to hear Matt and John’s nuanced perspectives on these unfolding stories, and stay ahead in the ever-evolving world of business, technology, and policy.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

In this episode of Tank Talks, host Matt Cohen sits down with Mayuran Yogarajah, the visionary behind Index Exchange, one of Canada's most successful ad tech companies. From the early days of Casale Media to growing Index Exchange into a global powerhouse, Mayuran shares the remarkable journey of scaling a bootstrapped business in an industry dominated by tech giants. We also dive deep into his expansion into venture capital with IX Labs and the latest innovations in ad tech.The Genesis of Index Exchange (00:02:10)* How Mayuran’s journey at Index Exchange started and the pivotal moments that shaped its success.* The early days of Casale Media, their transition to Index Exchange, and the world of programmatic advertising.* Overcoming the challenge of real-time bidding and how they reshaped the ad tech industry.Building a Global Ad Tech Leader (00:10:45)* From a small team to 600 employees across 16 global offices.* The growth of Index Exchange and its mission to remain independent in a highly consolidated ad tech market.* The development of header bidding technology and how it revolutionized publisher revenue generation.The Power of Transparency & Trust (00:17:30)* Mayuran’s approach to maintaining trust in a highly competitive industry and the company's commitment to transparency with their Client Audit Logs.* Why clients trust Index Exchange to keep their data safe and their processes transparent, unlike larger platforms like Google and Facebook.The Rise of AI in Ad Tech (00:22:15)* How AI is reshaping the ad tech space and what it means for the future of digital advertising.* The integration of machine learning and neural nets in improving data filtering and ad serving.* How AI tools are empowering ad tech companies to scale operations with efficiency.A Bold Move into Venture Capital with IX Labs (00:30:30)* The story behind the launch of IX Labs and how it aligns with Index Exchange’s mission to diversify.* Mayuran’s approach to backing early-stage companies and helping scale innovation in hardware and deep tech.* The importance of building a business with solid leadership, not just solid technology.Ad Tech and the Changing Market Landscape (00:38:00)* Why Index Exchange hasn’t gone public yet and how they’ve managed to remain agile and successful without external investment.* The impact of changing global economics, how tariffs, recession fears, and rising interest rates influence ad tech budgets and strategies.As businesses in ad tech and beyond continue to navigate the shifting landscape, they must adapt or risk falling behind. Mayuran Yogarajah and Index Exchange are leading the charge, proving that with the right mix of innovation, transparency, and a commitment to scaling sustainably, success is within reach. Will companies in the ad tech world rise to meet the challenges of an evolving digital landscape, or will they struggle to stay ahead in an era where agility, transparency, and technology define the future of advertising?About Mayuran YogarajahMayuran Yogarajah is the co-founder and leader behind Index Exchange, one of the world's leading independent ad exchanges. With over 20 years of experience in the ad tech industry, Mayuran has been pivotal in transforming Index Exchange from its humble beginnings as Casale Media to a global leader in programmatic advertising. Under his leadership, the company has pioneered industry-shifting technologies like header bidding and continues to scale globally with offices in 16 cities worldwide. Mayuran is also the driving force behind IX Labs, where he is helping venture into the world of venture capital, supporting early-stage startups in hardware and deep tech.Connect with Mayuran Yogarajah on LinkedIn: https://www.linkedin.com/in/mayuran-yogarajah/Visit the Index Exchange website: https://www.indexexchange.com/Connect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1Visit the Ripple Ventures website: https://www.rippleventures.com/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit tanktalks.substack.com

Welcome back to another power-packed episode of Tank Talks! Matt Cohen is once again joined by John Ruffolo to break down one of the most divisive and impactful elections in Canadian history. From Alberta’s fury and NDP’s collapse to the growing political alignment on tech policy, this episode peels back the layers on what just happened and what’s coming next.* The shocking downfall of Jagmeet Singh and the NDP* Mark Carney’s debut win and what it means for national unity* Alberta’s boiling anger and the risk of Western alienation* The truth behind Microsoft’s AI revenue surge and whether it’s smoke and mirrors* Why tech leaders are finally seeing political alignment in OttawaElection Earthquake: Liberals Win, But is it Really a Minority? (00:02:00)Canada’s 2025 federal election saw Mark Carney’s Liberals clinch 169 seats, just three short of a majority. But is this really a minority government?John’s take: Treat it like a majority. No one wants another election, and Carney may hold power longer than expected, possibly 12 to 24 months of clear runway. But the NDP collapse and talk of MP defections are setting the stage for high-stakes political bargaining.The NDP Implodes: Jagmeet Singh Steps Down (00:02:43)The New Democratic Party faces political extinction, just 6% of the vote and seven seats, losing official party status for the first time in decades.John’s take: Expect backroom deals. Whether it's extending party status or poaching MPs, the Liberals may offer the NDP a lifeline in exchange for quiet support. But it’s a risky game and could backfire with voters.Alberta's Fury: Is Western Alienation Back? (00:07:52)Premier Danielle Smith is fuming, warning that Alberta may escalate demands if its economic interests aren’t prioritized. With 34 out of 37 seats going Conservative, Alberta feels ignored, again.John’s take: Their frustration is justified. Ottawa’s refusal to discuss pipelines or LNG is alienating a province that bankrolls the nation. If Alberta walks, Canada loses its economic engine.Tech’s Policy Wish List: Capital Gains, AI, and Procurement (00:11:26)Canadian tech leaders wasted no time, issuing a post-election call to action: reform capital gains, support Canadian-built tech, and invest in AI infrastructure.John’s take: The time for polite advocacy is over. With both Liberals and Conservatives aligning on major innovation policy, the opportunity for real progress has never been better, if egos don’t get in the way.Surprise Unity: Liberals & Conservatives Align on Innovation (00:12:24)Despite the heated rhetoric, the two leading parties are shockingly aligned on digital strategy, immigration reform, and even open banking.John’s take: There’s nearly 80% overlap. Both parties want economic growth through tax relief, fast-tracked infrastructure, and internal free trade. Entrepreneurs are leading the charge, it’s time politicians caught up.Microsoft’s AI Playbook: Real Money or Recycled Revenue? (00:15:24)Microsoft’s stock jumps as AI revenues appear to surge, but is it genuine growth or just a repackaged Office 365 price hike?John’s take: Be skeptical. Most of the new revenue might just be legacy SaaS customers forced into higher prices. Until there’s clear evidence of fresh, net-new AI revenue, it’s mostly smart marketing.The AI Gold Rush: Are Startups Actually Winning? (00:18:12)John questions whether AI startups are truly reaping rewards or just helping Big Tech inflate its margins. And with hyperscalers spending tens of billions, pressure is mounting to prove the returns are real.John’s take: Don’t confuse exploratory pilot projects with actual adoption. Many corporates are still in “test mode,” and unless startups can prove long-term value, they risk getting left behind in an AI bubble.As Canada redefines its political and economic future, this episode offers unfiltered insights into what’s really going on in Ottawa, Alberta, and Silicon Valley North. If you’re a founder, investor, or policy leader, this is essential listening.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

Welcome back to Tank Talks! Host Matt Cohen is back with the one and only John Ruffolo in another no-holds-barred news rundown from the frontlines of business, tech, and politics. With Canada barreling toward an election that could reshape its economic future, and global giants like Google facing legal evisceration, this episode is packed with jaw-dropping insights.* Why the Canadian election might deliver another political deadlock and why that terrifies investors.* The secret behind Google’s looming breakup and OpenAI’s wild move to snag Chrome.* Inside the AI shell game: How Ottawa’s $2B bet could be more smoke than fire.* Rising gold, crashing confidence: Is Bitcoin back or are the gold bugs winning?Platforms vs. Reality: Are Politicians Just Rearranging Deck Chairs? (00:03:25)Matt and John break down the policy platforms with brutal honesty, from fantasyland deficit projections to a tax-and-build housing bonanza that may never materialize.John’s take: Liberal spending assumptions are based on fantasy GDP projections. Meanwhile, conservative tax relief and entrepreneurial support feel more grounded but still beg the question, “Where’s the execution?”AI Reallocations or Just a Shell Game? (00:08:04)The $2 billion AI investment promised by the Liberals is under scrutiny. The Conservatives say it’s a reallocation, not a cut, but John isn’t sold on the ROI.John’s take: Ottawa’s indiscriminate tech funding might be helping foreign giants more than Canadian innovators. Real results will only come from supporting homegrown ecosystems, not flashy line items.Google Breakup Incoming? OpenAI Eyes Chrome (00:14:00)A U.S. court just found Google guilty again, this time for monopolizing ad tech. The breakup buzz is real, and OpenAI is already circling Chrome like a hawk.John’s take: This antitrust reckoning is 10 years late. Chrome is key to Google’s dominance, but the real threat may now be Gen Z’s shift to LLM-powered search. The disruption has already begun.Sell Everything U.S.? Global Rotation or False Alarm? (00:17:25)Markets are jittery. U.S. equities are underperforming. International funds are surging. Is this the start of a broader retreat from the American financial engine?John’s take: If the U.S. wobbles, where do you go? The answer might be gold, Bitcoin, or both. As fiat faith erodes, the store-of-value debate is back with a vengeance.Gold vs. Bitcoin: The Great Store-of-Value Showdown (00:18:37)Gold is soaring. Bitcoin bugs are stirring. With the U.S. dollar under pressure and investors fleeing uncertainty, we might be entering a new age of alternative assets.John’s take: Gold’s silent resilience is paying off again. Meanwhile, Bitcoin maxis are rallying, but in the debate? Gold is taking the lead.In a world of broken platforms, fiscal illusions, and rising geopolitical chaos, this episode is a crash course in the new rules of money, tech, and power.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

Welcome back to Tank Talks! In this episode, host Matt Cohen is joined by John Ruffolo for another high-voltage rundown of the most urgent headlines at the intersection of business, politics, and innovation. As Canada stares down the barrel of a snap federal election and the U.S. economy teeters on a razor’s edge, this episode is all about decoding the chaos.* Can Canada avoid a recession as political gridlock looms?* Will U.S. economic volatility derail global investment?* What happens when tech titans like Musk and Dorsey call for the end of intellectual property law?From capital gains clashes and cross-border tax traps to TikTok-fueled counterfeits and China's IP free-for-all, this conversation goes deep into the geopolitical and economic fault lines shaping our future.Election Whiplash: Personality Over Policy (00:01:00)With Canada’s snap election just days away, John and Matt unpack the shift from hard policy debate to emotional brand politics. Despite mounting economic concerns like productivity slumps, unaffordable housing, and rising interest rates, voters seem more fixated on the personalities of frontrunners Mark Carney and Pierre Poilievre.John’s take: We may be headed toward a minority government, but the real issue is voter apathy. If younger voters don’t turn up, expect unpredictable outcomes. Meanwhile, the debates are muddying policy distinctions, making this more of a popularity contest than a strategic vote.Tax Turbulence: Capital Gains and Cross-Border Chaos (00:04:00)Capital gains are back in the spotlight on both sides of the border. In Canada, competing parties offer conflicting visions on taxation. But south of the border, new U.S. proposals could triple taxes on Canadian investors holding U.S. assets.John’s take: Canada’s assumption that U.S. Democrats would win and raise capital gains taxes might backfire. If Republicans take over and slash taxes instead, Canada’s competitiveness could tank. The stakes? Talent flight, diminished foreign investment, and a harsh wake-up call for young Canadians evaluating life abroad.Trump, Tariffs, and the Trade War Ripple Effect (00:07:31)Trump’s tariff spree continues to rattle markets. Mixed signals and shifting policies have left Canada and much of the world scrambling for economic footing.John’s take: Canada has been over-indexing on Trump rather than addressing its domestic weaknesses. Blaming external forces won’t fix structural problems like low productivity and weak innovation infrastructure.Recession Realities: Brace for Impact (00:11:50)With interest rates climbing and the bond market flashing red, John paints a sobering picture: a Canadian recession is not just likely, it’s imminent. But not all is doom and gloom.John’s take: Recessions are where great companies are made. The key is balance sheet strength and a strategy to gain market share, even at the cost of short-term profits. It’s survival of the most prepared.Fear vs. Opportunity: Investing Amid Uncertainty (00:13:00)Despite market jitters, John’s firm is busier than ever. He sees opportunity in volatility, just not for the faint of heart.John’s take: Most people freeze in a downturn. That’s a mistake. Investors and founders need to think like race car drivers, slow down strategically, but stay ready to accelerate when the track clears.The IP Debate Goes Nuclear: Musk & Dorsey Speak Out (00:17:00)In a viral exchange, Jack Dorsey and Elon Musk call for the abolishing of intellectual property laws. They argue IP stifles creativity and prioritizes lawsuits over innovation.John’s take: While the system needs reform, scrapping IP entirely is extreme. Protection encourages R&D, especially for startups. The real threat? Patent trolls and uneven enforcement that favors deep-pocketed players.The Counterfeit Tsunami and China’s Rule-of-Law Rebellion (00:20:50)From luxury bags to Tesla knockoffs, China’s casual relationship with IP law is costing Western economies over $600 billion annually. And the stakes are rising.John’s take: The U.S. once stood as a beacon for rule-based trade. Now, it's playing the same unpredictable game as China. Without global cooperation, the IP battlefield could become a free-for-all, and that’s dangerous for everyone, especially startups.As elections, tariffs, and tech wars reshape the global economy, this episode is your essential guide to what’s coming and how to prepare. Whether you're a founder, policymaker, or investor trying to read the tea leaves, John and Matt deliver the no-nonsense insight you won't find anywhere else.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

Welcome back to another hard-hitting news roundup on Tank Talks! Host Matt Cohen is joined once again by John Ruffolo to unpack the economic tremors shaking North America. From Trump’s tariff war and its looming consequences for Canada, to Toby Lutke’s bold AI ultimatum at Shopify, this episode is a masterclass in high-stakes business, politics, and innovation.* Will Trump’s economic war trigger a global market meltdown?* Why John Ruffolo says stagflation is now a real and terrifying threat for the U.S.* Canada’s recession warning: Why this election may determine its economic fate.* The open letter shaking up Ottawa: What 150 Canadian tech leaders want to see from party leaders.* Toby Lutke’s AI revolution at Shopify and why it’s a wake-up call for every CEO.* The dark side of AI hype: How one founder allegedly duped investors with fake automation.U.S. on the Brink: Trump’s Trade War Fallout (00:02:00)* Trump’s reciprocal tariffs are back, and global markets are reacting with volatility.* China appears to be offloading U.S. assets, triggering a bond market selloff and pushing interest rates higher.* The big fear: stagflation, as inflation rises while growth slows and debt becomes harder to manage.John Ruffolo’s Take:John sees this move as poorly executed and dangerously short-sighted. What could’ve been a calculated economic strategy has turned into global chaos. The lack of nuance and timing has undermined investor confidence, and John believes this could accelerate a stagflation crisis with long-lasting damage to U.S. economic credibility.Canada’s Economic Crossroads: Recession Ahead? (00:09:00)* The Bank of Canada is expected to cut interest rates again to ease mounting pressure on consumers and businesses.* Ontario’s auto sector is at serious risk, with ripple effects across the broader Canadian economy.* 75% of Canada’s exports go to the U.S., making the country highly vulnerable to Trump’s tariffs.John Ruffolo’s Take:John believes Canada is headed straight for a recession and warns that the country has ignored economic fragility for far too long. He argues that domestic production has been hollowed out, and the only way forward is to embrace economic nationalism, support Canadian entrepreneurship, and build self-reliant industries, starting with our natural resources.Canada’s Innovation Wake-Up Call: 150 Tech CEOs Demand Action (00:18:00)* The Council of Canadian Innovators released an open letter signed by 150 CEOs demanding action on economic sovereignty and innovation policy.* Key demands: protect Canadian data, support domestic tech companies through procurement, and end subsidies to foreign-owned competitors.* Political leaders are finally listening, but will it translate into post-election results?John Ruffolo’s Take:John has been calling for these reforms for nearly a decade, and for the first time, he feels there’s real momentum. He credits growing public awareness for the shift but stresses that this can’t just be a campaign talking point. Real action, especially around digital sovereignty and government procurement, is long overdue.Shopify’s AI Mandate: Innovate or Get Left Behind (00:22:00)* Shopify CEO Toby Lutke announces a bold internal policy: AI adoption is now mandatory for all employees.* Workers must prove that AI can’t solve their problems before requesting additional resources.* Performance reviews will include AI usage as a key metric.John Ruffolo’s Take:John applauds Shopify’s move as the kind of leadership every company needs to adopt. With shrinking workforces and rising expectations, he says companies must shift from growing headcount to growing productivity. AI isn’t just a competitive advantage, it’s a survival requirement, and Shopify is setting the new standard.AI Smoke & Mirrors: Startup Scandal Exposes Industry Hype (00:25:00)* Fintech startup Nate raised $50M pitching an AI-powered shopping app, but it was secretly powered by manual labor in the Philippines.* The founder is now facing fraud charges after misleading investors about automation levels.* This may be the tip of the iceberg as AI hype continues to outpace reality.John Ruffolo’s Take:John isn’t surprised and believes this is just the beginning. In the rush to back anything labeled “AI,” many investors skipped proper diligence. He warns that more AI fraud cases are likely to emerge, especially in startups that overpromise automation without the infrastructure to deliver it.As global markets face volatility, Canada wrestles with recession fears, and AI adoption accelerates across industries, this episode lays bare the urgent challenges and opportunities ahead. Whether you're an investor, founder, or policymaker, this is a must-listen deep dive into the forces reshaping our economic future.Connect with John Ruffolo on LinkedIn: https://ca.linkedin.com/in/joruffoloConnect with Matt Cohen on LinkedIn: https://www.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

In this episode of Tank Talks, we dive into one of the most significant shifts happening in tech right now: the rise of AI agents.Our guest, Adam Coccari, has a front-row seat to the AI transformation as the Managing Director of HubSpot Ventures. But what makes Adam’s story so compelling is how it began, not in boardrooms, but in a classroom, teaching 4th-grade math. From building an educational gaming app with no tech background to helping launch Microsoft’s venture fund, Adam’s journey is anything but typical.We explore why agentic AI is reshaping how work gets done, which sectors are already feeling the shift, and how founders can build winning SaaS companies without bloated teams or massive rounds. Adam breaks down what separates lasting startups from hype-fueled flashes and shares tactical advice for early-stage founders navigating the AI-powered future of business.From Teacher to Tech: Adam’s Unusual Path to Venture (00:01:54)* Why building a math app for kids led Adam into tech* Lessons from the classroom that still shape his leadership today* How “Math Evolve” became a top-ranked game and what went wrongCloud, AI & Lessons from Microsoft (00:09:07)* What Adam learned working on Azure before it was cool* How B2B sales, marketing ops, and funnels really work* The early power of machine learning in enterprise use casesInside Corporate VC and the M12 Playbook (00:11:59)* What most corporate venture arms get wrong* Why being “just strategic” isn't enough anymore* How M12’s independent structure helped them win dealsWhy Agentic AI Is Having Its Moment (00:21:46)* What makes AI agents different from traditional automation* Why back-office work is ground zero for agentic disruption* Real examples in bookkeeping, AR, customer service, and moreBuilding AI SaaS in 2025: What Founders Need to Know (00:24:31)* The rise of vertical SaaS powered by AI* What “experimental ARR” means and how to see through it* Why speed, execution, and domain knowledge beat scaleHow Startups Should Think About Go-To-Market (00:27:10)* Why PLG-first startups may scale to enterprise better than top-down players* What metrics actually matter in early-stage AI SaaS* Why a 3-person team can now do what used to take 30What Investors Are Looking For Now (00:34:08)* What Adam really looks for in AI founders* How he spots resilience, vision, and product intuition early* Why founder-market fit is more important than everPartnering, Platforms & Navigating Corp Dev (00:41:28)* The truth about working with big platforms as a startup* How to think about M&A as a long-term signal, not a strategy* Why transparency and trust still matter in the AI eraThis isn’t just another AI hype episode. It’s a real look into how work, software, and venture are changing fast. As AI rapidly reshapes how businesses operate, startups and incumbents alike stand at a crossroads: adapt or fall behind. Adam Coccari makes it clear: Agentic AI isn’t on the horizon; it’s already here, transforming how teams handle back-office tasks, optimize workflows, and scale faster with less. The question is: will companies embrace AI as a force multiplier, or get left behind in an era where agents don’t just assist, they execute?About Adam CoccariAdam Coccari is the Managing Director of HubSpot Ventures, where he leads investments in early-stage SaaS and AI startups. He was previously a founding member of Microsoft’s M12 venture arm and led venture efforts at Intuit. Adam began his career as a math and technology teacher, where he created the hit educational app Math Evolve, featured globally by Apple.Today, he focuses on backing bold founders building AI-native applications, with a special eye on agentic workflows, vertical SaaS, and B2B automation. His mix of product intuition, startup empathy, and platform strategy makes him one of the most thoughtful voices at the intersection of SaaS and AI.Connect with Adam Coccari: https://www.linkedin.com/in/adam-coccari-9932a134Visit the HubSpot website: https://www.hubspot.com/venturesConnect with Matt Cohen: 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

In this episode of Tank Talks, we sit down with Dan Debow, serial entrepreneur and former Shopify executive, along with returning guest and venture powerhouse John Ruffolo, for an unfiltered conversation about the intersection of innovation, public policy, and Canada's economic future.Fresh off his launch of Build Canada, Dan opens up about the real reasons he left Shopify, why Canadian entrepreneurs are stepping into the policy arena, and what it’s really going to take to grow GDP and national prosperity in a fast-changing world. Along the way, he reflects on his journey building Workbrain, Rypple, and Helpful, and scaling inside giants like Salesforce and Shopify.Is Canada ready to compete in the next wave of global innovation? What’s broken in our approach to growth—and how do we fix it? What’s driving entrepreneurs to dive into politics and policy?Canada’s Innovation Journey: From Workbrain to Build Canada (00:02:00)* Dan’s origin story: law school, business school, and falling into entrepreneurship with David Ossip* The early days of Toronto tech—from suburban enterprise software to downtown demo camps* How mesh conference, StartupNorth, and CDL shaped Canada’s tech communityCycles of Tech: Hype, Troughs, and the Next Big Shift (00:08:00)* Where we are in the AI, crypto, and innovation hype cycles* Why downturns are fertile ground for builders—not just tourists* The rise of low-cost tools, global access, and the democratization of entrepreneurshipWhy Entrepreneurs Are Entering the Policy Arena (00:14:00)* The real story behind Dan’s departure from Shopify* What sparked Build Canada—and why it’s more than a “tech bro” think tank* Why policy and entrepreneurship can no longer live in separate silosWhat Is Build Canada, Really? (00:20:00)* The memo process: how ideas turn into actionable policy* Why it’s not just for tech—housing, energy, and pipelines are in the mix* How entrepreneurs are pushing to shift the Overton window with bold, constructive ideasThe False Divide: Tech vs. Everyone Else (00:23:00)* Why the concept of a “tech industry” is outdated* Every sector is becoming a tech-enabled sector—Canada needs to catch up* How entrepreneurs can bring startup-style thinking into national progressGrowth, GDP, and the Real Incentives Behind Build Canada (00:29:00)* No hidden agendas: why patriotism—not profit—is driving this movement* The connection between economic growth and social progress* Why now is a defining moment for Canada's future competitivenessWhat's Next for Canada’s Innovation Economy? (00:36:00)* The upcoming election and why it matters for builders* How Build Canada is influencing real policy conversations already* Tools, debates, and what you can do to join the movementAs Canada's economic future hangs in the balance, Dan Debow and John Ruffolo make a powerful case: it’s time for the builders to step up—not just in startups, but in shaping the very fabric of our country. Growth isn’t a dirty word. It’s the foundation for everything else we care about. Will Canada embrace a new generation of entrepreneur-led leadership, or keep playing by old rules in a new world?About Dan DebowDan Debow is a serial entrepreneur, investor, and tech executive who’s played a pivotal role in shaping Canada’s innovation ecosystem. He was a founder of Workbrain (acquired for $227M), co-founder of Rypple (acquired by Salesforce), and co-founder of Helpful (acquired by Shopify), where he went on to serve as a senior executive for six years. He’s also an active early-stage investor, mentor, and policy advocate.Now, Dan is one of the driving forces behind Build Canada—a grassroots policy initiative aimed at reimagining how Canada can unlock its growth potential by putting builders at the heart of national decision-making. Beyond tech and policy, Dan is also a passionate musician and co-founder of Bonfire Collective, a non-profit supporting Canada’s creative communities.Connect with Dan Debow: https://ca.linkedin.com/in/ddebowLearn more about Build Canada: https://www.buildcanada.com/Connect with Matt Cohen: 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

On this episode of Tank Talks, we welcome back Villi Iltchev, founder and managing partner of Category Ventures, for an unfiltered deep dive into the evolving venture capital landscape. From his early days at Salesforce Ventures to launching his solo $160M fund, Villi unpacks the seismic shifts happening in enterprise software, how AI is reshaping startup economics, and what today’s founders need most from their investors.We get tactical about startup pricing models, founder-investor trust, and what it takes to build truly category-defining companies. Villi also shares what he learned from backing GitLab, why transparency builds long-term trust, and how he thinks about firm design as a solo GP.Whether you're an aspiring founder, current operator, or an emerging VC, this episode is a masterclass in strategic thinking and building with purpose.Inside the Mind of a Modern VC (00:01:00)* Villi’s journey from tech banking to Salesforce Ventures* Why Salesforce’s transformation into a platform company changed everything* The parallels between Salesforce and NVIDIA’s ecosystem dominance* How being early at Salesforce shaped Villi’s thesis around go-to-market and platform strategyScaling GitLab: Lessons from the Frontlines (00:15:00)* The inside story of GitLab’s infamous database failure—and why live-streaming the crisis built trust* Why Villi pushed GitLab to sunset unscalable SKUs and simplify pricing* The power of bundling and setting an “aspirational” price point from day oneGoing Solo: Building Category Ventures (00:25:00)* Why Villi finally felt ready to start his own fund—and what changed* The biggest surprises (and reliefs) in raising as a solo GP* How LPs are getting more sophisticated and what they want from fund managers* Why venture needs a reset and what legacy firms are getting wrongThe New Rules of Early-Stage Investing (00:32:00)* Why founder/firm misalignment leads to orphaned startups* The real impact of mega-funds dabbling at seed and pre-seed* Why Category Ventures is built to be flexible—and fiercely focused on enterprise softwareAI, Startups & the Future of Enterprise (00:38:00)* Villi’s hot take on AI-powered lean startups: “It’s not the norm—and won’t be.”* Why AI is a second-order unlock for vertical SaaS and back-office automation* The coming wave of software replacing the BPO industryLife, Adrenaline, and VC Energy (00:45:00)* What gets Villi’s adrenaline pumping as a VC* Why endless internal meetings kill his vibe—and founder calls fuel him* How skiing and extreme adventure balance the chaos of ventureAs the venture landscape shifts under our feet, Villi Iltchev is proving that thoughtful investing, deep expertise, and founder-first empathy are more vital than ever. From GitLab board rooms to building Category VC, his journey is a blueprint for those looking to lead with clarity—and conviction.About Villi Iltchev:Villi Iltchev is the founder and managing partner of Category Ventures, a $160M early-stage venture firm focused exclusively on enterprise software. With a career spanning both operating and investing, Villi brings a rare blend of empathy and edge to the startups he backs—having sat on both sides of the table.He began his career in tech investment banking before transitioning into operating roles at companies like Hewlett-Packard, LifeLock, and Box. He later joined Salesforce Ventures at its inception, helping to build one of the most influential corporate venture arms in the world. During his time there, he led investments in category-defining companies like GitLab and HubSpot.Prior to launching Category Ventures, Villi was a partner at August Capital and Two Sigma Ventures, where he built a strong track record backing developer tools, infrastructure, and vertical SaaS startups. His investments are grounded in deep enterprise domain expertise, a keen sense for go-to-market strategy, and a relentless focus on founder empathy.A lifelong learner and backcountry skiing enthusiast, Villi draws creative energy from the outdoors and adrenaline-fueled adventures. He holds degrees in finance and philosophy and is driven by a singular belief: the best founders don’t just build products—they redefine categories.Follow Villi Iltchev on LinkedIn: https://www.linkedin.com/in/villi04Visit the Category Ventures website: https://www.categoryvc.com/Follow 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

On this episode of Tank Talks, Matt Cohen sits down with Michael Garrity, Executive Chair and Founder of Financeit, alongside recurring guest, John Ruffolo. Michael shares his unconventional journey—from growing up in remote Canada to navigating the world of venture capital, fintech, and regulatory battles. He reveals how he pivoted CommunityLend after facing regulatory roadblocks, ultimately transforming it into Financeit, which became Canada’s largest point-of-sale lender for home improvement.We also dive into:* The hard lessons of scaling a fintech company* How Goldman Sachs’ investment changed Financeit's trajectory (and the tough call that put the company up for sale)* Why Canada needs better fintech regulations and open banking policies* How tariffs, economic shifts, and political uncertainty are reshaping the fintech industry* The resilience required to build and scale a successful business in CanadaMichael Garrity’s Journey from Politics to Fintech (00:01:00)* How growing up in Northern Canada shaped his entrepreneurial mindset* His unexpected path into venture capital and fintech* What he learned from early-stage investing and Canada’s labor-sponsored fundsThe CommunityLend Pivot: How Failure Led to a Billion-Dollar Business (00:05:00)* Why Canada’s financial regulators blocked his first fintech startup* The painful decision to pivot away from peer-to-peer lending* How FinanceIt found product-market fit and scaled rapidlyWinning in Fintech: What It Takes to Build a Market Leader (00:12:00)* The strategic acquisition of TD’s home improvement lending business* How partnering with Goldman Sachs helped Financeit scale* The biggest mistakes founders make when raising capital from big-name investorsThe Future of Fintech & Canada’s Economic Challenges (00:25:00)* Why Canada’s regulatory environment is stifling innovation* How tariffs, inflation, and deglobalization are impacting Canadian businesses* Why open banking is critical for fintech growth in CanadaMichael’s Advice for Founders & Leaders (00:40:00)* Why the best founders have grit and adaptability* How to navigate industry shakeups and market downturns* Why trust, relationships, and strategic pivots matter more than everAs Canada navigates economic uncertainty, fintech disruption, and regulatory battles, founders must adapt or risk being left behind. Michael Garrity’s story proves that persistence, strategic thinking, and a willingness to pivot are the keys to building a billion-dollar business. Will Canada’s fintech ecosystem rise to the challenge, or will regulatory roadblocks continue to hold it back?About Michael GarrityMichael Garrity is the Executive Chair and Founder of Financeit, a leading point-of-sale financing platform for home improvement projects in Canada.Michael is a seasoned fintech entrepreneur who has built and scaled multiple financial technology businesses. His journey began in venture capital and early-stage investing, where he worked on Canada’s early labor-sponsored investment funds. He later co-founded CommunityLend, a peer-to-peer lending marketplace that faced regulatory challenges—leading to a high-stakes pivot that ultimately resulted in FinanceIt.Under Michael’s leadership, FinanceIt grew into Canada’s dominant home improvement lender, with billions in loan originations and major financial backers, including Goldman Sachs. Today, he continues to shape the industry while advocating for open banking and smarter fintech regulations.Follow Michael Garrity on LinkedIn: https://linkedin.com/in/michael-garrity-7a87152Visit Financeit’s website: https://www.financeit.io/Subscribe to our YouTube channel: https://www.youtube.com/@thetanktalkspodcastFollow Matt Cohen on LinkedIn: https://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