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EP004 — Charles Cormier on Systems, Cold Email, and Why Most Founders Get Fundraising Wrong 

Charles Cormier is a founder who doesn’t wait for permission. As CEO of RaasRocket and founder of GTM Ventures and the Podbuyer podcast network, he’s learned that fundraising today is just as much about the systems you build as the people you know. In this episode, he sits down with Maxim Atanassov to unpack why traditional approaches like warm intros and VC lunches often fall flat—and what to do instead. His take is simple, practical, and grounded in real outcomes, all shaped by a first-principles, energy-efficient way of working. 

We dig into how capital markets have shifted: hype alone is no longer enough to get you funded, and a lot of founders haven’t caught up. Charles has worked with hundreds of founders on fundraising and go-to-market strategy and keeps seeing the same patterns show up again and again. 

Here are a few of the most interesting things we cover: 

1. Systems-Based Fundraising: Charles explains why a well-built cold email outreach system—something you can turn on, measure, and keep improving—often beats traditional networking for most founders who don’t already have decades of relationships. 
2. What Makes a Company Investible: At the end of the day, investors want proof—not just a polished pitch deck. They’re looking for traction, real revenue, and a financial model that clearly shows meaningful upside, plus risks they can understand and live with. 
3. Podcasting as a Strategic Weapon: A podcast isn’t just about downloads or exposure. When you treat it like a system, it becomes a source of data, a credibility signal, and a structured way to regularly earn 30 minutes with investors who might never otherwise take a meeting with you. 
4. Why Founders Shouldn’t Romanticize Fundraising: Raising capital is a milestone—not the finish line. The real win is building a profitable, durable company, but lots of founders still confuse raising money with actually succeeding. 
5. AGI and the Future of Entrepreneurship: After surveying more than 2,000 founders, Charles found that only about 1% have a solid grip on what’s coming with AI. He calls this a “fundamental sin” for anyone serious about building a company today. 

3 Key Insights 

These are some of the key insights from our talk: 

1. Put your energy where it actually counts. Systems—like email campaigns, podcast workflows, or AI tools— help turn effort into real and repeatable results. Burnout usually shows up when you’re stuck doing high-effort, low-reward work without enough support or leverage. 
2. Investor fit is harder than most founders think. It's not about check size — it's about understanding what actually drives someone to write that check. Sometimes it's pure thesis alignment. Sometimes it's personal. Charles talked about biotech investors who got involved because they lost someone to cancer. You don't find that out from a CRM. You find it out by doing the work — conversations, follow-ups, actually paying attention to what people tell you. 
3. And on the AI front, Charles is blunt about where this is heading. Agents are already handling chunks of the work inside their company. The founders who'll thrive aren't the ones doing more. They're the ones figuring out what only they can do: closing, setting direction, making the calls that machines can't. Everything else is getting automated, whether you're ready or not. 

About Charles Cormier 

Charles Cormier is a serial entrepreneur, CEO of RaasRocket, and founder of GTM Ventures and the Podbuyer podcast network. He helps founders raise capital and speed up their go-to-market efforts through systems-driven cold outreach, strategic podcasting, and first-principles thinking. 

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Guest: Paul Anthony Claxton, Managing Partner, Digerati Investments

About This Episode

Paul Anthony Claxton didn't follow the usual route into venture capital. He served four combat tours in Iraq as a United States Marine — including leading a command intelligence center where he observed the early days of drone warfare — before enduring six years of corporate layoffs, building a bootstrapped company to $20K MRR in three months, and eventually moving into early-stage investing. Today, he manages Digerati Investments, a $60 million AI-focused seed and Series A fund based in Southern California.

This conversation is worth your time because Paul operates at a rare intersection: operator empathy, military-grade discipline, and a genuine sophistication around capital strategy that most early-stage investors don't bring to the table. He's not interested in hype. He's interested in founders who understand what they're building, why they're raising, and whether venture capital is even the right tool for their business — a conversation most of the industry is still too afraid to have.

Key Topics Covered

1. From the Marine Corps to venture capital — how four combat tours, a father who was a drill instructor, and six years of corporate volatility shaped Paul's worldview as an investor and operator.
2. What investors actually seek — and what destroys deals — Paul's three Ds framework: data rooms, diligence, and disclosure, and why most founders fail before the conversation even begins.
3. The issue with how founders approach fundraising — Why creating a pitch deck and jumping straight to VCs is the wrong first step, and what founders should know about capital markets before raising any money.
4. The SAFE note — what it gets wrong — A direct critique of the industry's most popular early-stage instrument, including why the absence of a valuation floor signals what Paul interprets as a lack of founder conviction.
5. The Reloadable Note — Paul's proprietary financing instrument designed to protect founders from early dilution while providing early-stage investors with real-time liquidity options at specified trigger events.

Key Insights:

1. Mental toughness is the true competitive advantage. The Marine Corps taught Paul that the toughest challenges are conquered brick by brick — with speed, intensity, and relentless focus on the smallest details. That same approach guides how he evaluates founders today.

2. Venture capital is not the default answer. Many founders assume that starting a company requires raising VC. Paul argues that understanding the complete capital stack — debt, ARR financing, venture debt, angel investment — and knowing why you're choosing VC is one of the most crucial hard skills a founder can develop.

3. AI is in its foundation-building phase — and most of what's out there won't survive it. Paul's view: the companies being built between now and roughly 2030 will serve as the foundational layer of the AI era — the next Googles and PayPals. Everything else driven by hype, lacking genuine utility or real-world impact, will fade away.

Links & Resources

• Paul Anthony Claxton on LinkedIn: https://www.linkedin.com/in/businessmanathletemarine
• Paul's website: https://www.paulclaxton.io/
• Digerati Investments: https://www.digeratiinvestments.com/
• Future Ventures Corp: https://www.futureventures.ca/

Guest B

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Ray Fitzpatrick, Founder & CEO, Profitual 

Ray Fitzpatrick spent ten years writing checks to startups as Director of Investments at NBIF — New Brunswick's pre-seed venture capital fund — and observed the same issue recurring across hundreds of companies. Founders excelled at developing products but struggled to grasp their own finances. This wasn’t due to laziness, but because no accessible tool existed for non-finance professionals to use effectively. That's the challenge Profitual aims to address. 

This discussion extends far beyond the product itself. Ray is a CPA and a serial entrepreneur managing three businesses at once, with firsthand experience on both sides of the investor table. His insights into fundraising, co-founder relationships, cap table design, and what financial literacy truly means for a scaling founder are rooted in real-world experience — not just theory. If you're building a company and have ever felt nervous when your investor asked about burn rate or runway, this is for you. 

Key Topics Covered 

1. The origin of Profitual — how a decade of observing non-finance founders grapple with investor reporting inspired Ray to create the "Canva for finance." 
2. Fundraising in Canada — Ray's honest breakdown of what works, what doesn't, and why building a snowball of early validation beats chasing a big lead investor. 
3. Cap table philosophy — Why Ray intentionally maintains conservative valuations, prefers common stock over preferred shares, and emphasizes timeliness of returns over headline valuation. 

3 Key Insights 

• A financial forecast that your founders can't explain is worthless. Ray's entire product philosophy revolves around this idea: it's not enough to produce impressive numbers; the business owner must understand what drives them. A polished AI-generated report filled with unsupported assumptions, especially one that can't be defended in an investor meeting, is worse than having no model at all. 
• Begin with validation rather than a pitch deck. During Ray’s time at NBIF, less than 2% of the companies that participated had any revenue or signed letters of intent. That small group immediately caught our attention. Securing written commitments from even one person — whether a customer, investor, or grant provider — can change the entire conversation. 
• The co-founder you rush into partnering with is the one who could cause your downfall. Ray lost his original Profitual co-founder early on because their visions weren't aligned. Since then, every successful partnership he's formed has been with someone he's worked closely with for years before ever considering going into business together. 

Links & Resources 

• Profitual website: https://profitual.ai/
• Ray Fitzpatrick on LinkedIn: https://ca.linkedin.com/in/raymond-fitzpatrick-66761263 
• Devil's Keep Distillery 
• NBIF (New Brunswick Innovation Foundation) 

About Ray Fitzpatrick 

Ray Fitzpatrick is the Founder and CEO of Profitual, a financial forecasting and reporting platform for startup founders and SME operators without a finance background. A CPA, Ray spent a decade as Director of Investments at NBIF, participating in over 200 financings and helping build a portfolio of 75 startups in New Brunswick. He's also a co-founder of Quantified Accounting and Devil's Keep Distillery, dedicating his time to developing Profitual and mentoring future founders. 

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From EdTech Exit to AI Agents: Scaling on Your Own Terms with David Kofoed Wind 

Guest: David Kofoed Wind ·(Founder of Agentwork) 

David Kofoed Wind has accomplished what most founders only talk about — building two companies from scratch, taking them through Y Combinator, scaling them responsibly without overextending on headcount, and selling one of them. He's a mathematician with a PhD in machine learning, a former CERN collaborator, and someone who has been seriously considering AI since he was thirteen. Now he's back in the game with Agentwork, a company rethinking how work gets done when AI and humans work together side by side. 

This conversation is valuable for founders trying to understand where AI genuinely fits into their operations — not just the hype, but the real substance. David speaks plainly about what has changed, what stays the same, and why pursuing headcount growth was never a smart move. He has been working at the forefront of this shift longer than most, and his insights on distribution, moats, and the future of digital work are based on hard-earned experience rather than speculation. 

Topics covered 

1. Engineering is no longer the bottleneck — building has become cheap and fast, which means the real constraint has shifted entirely to distribution. 
2. The audience moat — in a world where anyone can build a product overnight, founders who already own an audience have a structural advantage that compounds. 
3. What actually survives as a moat — features are dead as a competitive advantage; brand, switching costs, data, and network effects are what hold. 
4. How Agentwork works — a human-in-the-loop model that handles complex, open-ended work tasks for non-technical business teams, with tiered assurance levels built in. 
5. The future of work — David's honest take — a techno-optimist view on why this shift is different from the Industrial Revolution, and what it means for labor, hiring, and unit economics. 

Key insights from the Episode 

• Niche down until you can genuinely be the best in the world at something — not just the best book on negotiation, but the top resource on selling electric cars in a specific market. A smaller scope means less competition and a real chance to own the category. 
• The SaaS disruption will appear slow at first, then suddenly accelerate. Established players won't collapse overnight, but lean new entrants who build with AI and avoid hiring will slowly outperform them on unit economics until the gap becomes impossible to bridge. 
• Zero hallucinations are impossible philosophically, not just a product feature — humans hallucinate too. The smarter approach is to build systems where AI and human verification work together, because that combo is truly best-in-class. 

About David Kofoed Wind 

David Kofoed Wind is the founder of Agentwork, a human-in-the-loop AI platform designed for business teams that need complex work done reliably and at scale. He previously co-founded Peergrade and Eduflow, both Y Combinator companies that grew through product-led growth and were ultimately acquired by Mountiverse. David holds a PhD in machine learning and brings a rare combination of deep technical fluency and operator experience to every problem he addresses.