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/joruffolo

Connect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1

Visit the Ripple Ventures website: https://www.rippleventures.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/joruffolo

Connect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1

Visit the Ripple Ventures website: https://www.rippleventures.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/joruffolo

Connect with Matt Cohen on LinkedIn: https://www.linkedin.com/in/matt-cohen1/

Visit the Ripple Ventures website: https://www.rippleventures.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 wrong

Cloud, 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 cases

Inside 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 deals

Why 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 more

Building 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 scale

How 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 30

What 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 ever

Partnering, 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 era

This 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 Coccari

Adam 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-9932a134

Visit the HubSpot website: https://www.hubspot.com/ventures

Connect with Matt Cohen: https://ca.linkedin.com/in/matt-cohen1

Visit the Ripple Ventures website: https://www.rippleventures.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 community

Cycles 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 entrepreneurship

Why 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 silos

What 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 ideas

The 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 progress

Growth, 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 competitiveness

What'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 movement

As 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 Debow

Dan 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/ddebow

Learn more about Build Canada: https://www.buildcanada.com/

Connect with Matt Cohen: https://ca.linkedin.com/in/matt-cohen1

Visit the Ripple Ventures website: https://www.rippleventures.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 strategy

Scaling 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 one

Going 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 wrong

The 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 software

AI, 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 industry

Life, 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 venture

As 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/villi04

Visit the Category Ventures website: https://www.categoryvc.com/

Follow Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1

Visit the Ripple Ventures website: https://www.rippleventures.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 Canada

Michael 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 funds

The 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 rapidly

Winning 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 investors

The 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 Canada

Michael’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 ever

As 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 Garrity

Michael 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-7a87152

Visit Financeit’s website: https://www.financeit.io/

Subscribe to our YouTube channel: https://www.youtube.com/@thetanktalkspodcast

Follow Matt Cohen on LinkedIn: https://linkedin.com/in/matt-cohen1

Visit the Ripple Ventures website: https://www.rippleventures.com/

Welcome back to another thought-provoking episode of Tank Talks! Matt Cohen sits down with John Ruffolo to dissect the most pressing developments in tech, finance, and AI. From major banking shifts to the evolving landscape of AI-driven SEO, this episode delivers sharp insights and expert analysis you won’t want to miss.

* The Bank of Canada’s latest interest rate cut—will it actually help the economy?

* The power shift in Canadian banking: What CIBC’s CEO transition means for the future.

* Open banking and AI’s role in reshaping the financial landscape.

* The rapid rise of AI-driven SEO—how companies are optimizing for large language models.

* CoreWeave’s massive IPO plans and why John Ruffolo sees echoes of the Nortel bubble.

* The brewing U.S.-EU trade war—why Trump’s tariff threats could hit Canadian businesses harder than expected.

Canada’s Banking Future: CIBC’s Big Shift (00:04:00)

* Victor Dodig steps down as CIBC CEO after 11 years, handing over to Harry Cullum, a capital markets veteran.

* The big question: Can Cullum lead CIBC into the digital era, or will traditional banks struggle to keep up with fintech and AI-powered banking?

* Why open banking is no longer a threat, but an opportunity for Canada’s biggest banks.

John Ruffolo’s Take:

John sees Cullum as a strong leader with deep expertise in digital banking, positioning him well for the transition. However, he warns that legacy banks must move quickly to stay competitive as fintech innovation accelerates, or risk falling behind in a rapidly evolving financial landscape.

AI’s SEO Revolution: The Future of Search (00:10:00)

* Companies are now optimizing for AI models, not just Google Search.

* Mercury and Vercel are already seeing significant growth in inbound leads from large language models.

* The big shift: Instead of backlinks and keywords, companies are feeding training data directly into AI models.

CoreWeave’s Billion-Dollar Bet: Nortel 2.0? (00:14:00)

* CoreWeave, an AI-focused cloud company, is skyrocketing in valuation—going from $16 million in revenue to $1.9 billion in just two years.

* NVIDIA and Microsoft are heavily invested—so what happens if they pull the plug?

* Is CoreWeave truly innovative, or just benefiting from excess GPU capacity?

John Ruffolo’s Take:

"This reminds me way too much of Nortel in the late ‘90s. They pumped up revenue, but it was all based on unsustainable deals. Watch this one carefully."

As AI reshapes industries, banking undergoes major leadership shifts, and companies scramble to adapt to new digital landscapes, the stakes have never been higher. Will traditional banks successfully embrace open banking and digital transformation, or will fintech disruptors take the lead? Can AI-driven SEO remain a competitive advantage, or will regulators step in to level the playing field? And as CoreWeave pushes toward its high-stakes IPO, is this the beginning of a new tech revolution, or a repeat of past market bubbles? The coming months will reveal whether these trends signal long-term shifts—or short-lived hype.

On this episode of Tank Talks, Matt Cohen sits down with Daniel Saks, co-founder of AppDirect and now CEO & co-founder of Landbase, to explore the explosive rise of AI-powered go-to-market strategies. Fresh off a $12.5M seed round, Daniel reveals how Agentic AI is transforming B2B sales and marketing, the key lessons he learned from scaling AppDirect, and what it really takes to build a category-defining company.

* What does it take to build a billion-dollar SaaS company?

* How is AI reshaping the future of sales and marketing?

* Why do some entrepreneurs thrive while others struggle to scale?

The Rise of AI in Sales & Marketing (00:02:00)

* How Landbase is redefining B2B sales with Agentic AI

* Why traditional lead generation is broken—and how AI is fixing it

* The difference between generative AI vs. Agentic AI and why it matters

Scaling a Unicorn: AppDirect’s Journey & Hard Lessons (00:07:00)

* The seven-year journey to profitability at AppDirect

* Why AppDirect’s first major partnership almost failed—and how they pivoted

* How Daniel landed multi-million-dollar contracts with Deutsche Telekom, AT&T, and SoftBank

What Founders Get Wrong About Go-To-Market Strategies (00:15:00)

* The biggest mistakes startups make when scaling sales

* Why trust and relationship-building are the ultimate growth levers

* How AI is eliminating time-wasting manual processes for sales teams

The Future of AI & Business: What’s Next? (00:25:00)

* Why AI-powered tools will reclaim 70-80% of sales teams' time

* How agentic AI can simulate human sales reps and optimize campaigns in real time

* The 100x efficiency gain Landbase customers are already seeing

Daniel’s Advice for Founders & Leaders (00:40:00)

* Why the best founders have an insane vision—plus the ability to adapt

* How Daniel structured his multi-year transition plan out of AppDirect

* Why success is about falling in love with the problem—not the solution

As AI rapidly reshapes sales and marketing, businesses stand at a crossroads—adapt or be left behind. Daniel Saks and Landbase are proving that Agentic AI isn’t just the future—it’s already here, transforming how companies generate leads, build trust, and drive revenue. Will sales teams embrace AI as their most powerful ally, or will they struggle to keep up in an era where machines work smarter, not just harder?

Connect with Daniel Saks:

LinkedIn: https://www.linkedin.com/in/danielsaks

Visit the Landbase website: https://www.landbase.com/

Matt Cohen and John Ruffolo break down the seismic shift in Canadian politics as Mark Carney takes over as Prime Minister, succeeding Justin Trudeau. We explore what this means for Canada’s economy, upcoming elections, and how business leaders are reacting to the change.

* What’s next for Carney and the Liberal Party?

* Could Canada be heading for an April election?

* How will Canada’s economic policies evolve under Carney’s leadership?

Mark Carney Takes Over as Canada’s 24th Prime Minister (00:01:00)

In a widely expected move, Mark Carney won the Liberal leadership race with 86% of the vote, stepping into the role of Prime Minister. Despite having never held elected office, Carney’s deep experience in global finance makes him a powerful force in Canadian politics.

Carney’s Background:

* Former Governor of the Bank of Canada (2008-2013)

* Governor of the Bank of England (2013-2020)

* Economic advisor to Trudeau during COVID-19

* Declined a role in Harper’s Conservative government

What’s Next?With a tight race against Conservative leader Pierre Poilievre, Carney must move quickly to define his platform beyond broad economic promises. His leadership so far has been untested in political debates, raising questions about how he will navigate policy discussions leading up to a potential election.

John Ruffolo’s Take:“This is not a massive shift from Trudeau’s policies—it’s more of a continuation. Expect more government spending and taxation debates, but the big question is: How will Carney perform under real political pressure?”

Will Canada See an April Election? (00:03:00)

An early election could be announced as soon as March 16, with a vote set for April 22.

Key Election Dynamics:

* The Liberal Party is eager to hold elections before Conservative fundraising gains momentum.

* Carney currently lacks a parliamentary seat, which could impact campaign optics.

* A potential coalition between the Liberals, NDP, and Greens could reshape the political landscape.

Projected Outcomes:

* Conservatives still favored to win—but the margin is narrowing.

* A left-wing coalition could prevent a Conservative majority.

* Economic issues, particularly cost of living and taxation, will dominate voter concerns.

John Ruffolo’s Perspective:“With Canada’s economy still under pressure, the Liberals need to move fast. Their best bet is a short campaign before Pierre Poilievre gains further traction. If the Liberals delay too long, it could backfire.”

Canada’s Economic Crossroads: What Carney’s Policies Could Mean (00:07:00)

Carney has hinted at major spending initiatives, but concerns over taxation remain front and center.

Top Concerns:

* Rising debt: More government borrowing could impact inflation.

* Carbon tax shift: The tax isn’t going away—just moving from gas stations to industrial sectors.

* Cost of living crisis: Canadians are struggling with affordability, and tax policy will be a major campaign issue.

What’s Next?Will Carney unveil a bold new economic vision, or will his policies be Trudeau’s agenda rebranded? Investors, business leaders, and everyday Canadians are watching closely.

The Big Picture: What This Means for Canada

With a potential election looming, Canada stands at a political and economic crossroads. Will Carney’s leadership provide stability, or will voters seek a new direction under Pierre Poilievre?