Stephen Hedlund is head of finance at Rillet, an AI-native ERP which has raised over $100million from Sequoia and Andreessen Horowitz. In Steven’s words Rillet is “building the modern NetSuite.” In this episode:

• How Isaac Asimov’s Foundation helped me discover finance
• Experience from enterprise at Walmart to building startups
• Go-to-market (marketing) to Head of Finance Gillet
• The moat for leading ERPs and our strategy
• Being the ICP and marketing voice for Rillet

“To succeed, planning alone is insufficient. One must improvise as well.” ― Isaac Asimov, Foundation

Eddie Reynolds, CEO of UnionSquare Consulting, opens up about the often-fraught relationship between CFOs and CROs. Eddie shares insights from his unique journey—from banking and private equity to being an account executive at Salesforce which forecast within 5% accuracy despite 30%+ growth.

The conversation tackles the critical disconnect between finance and go-to-market teams: Why do CFOs struggle to trust CRM pipelines? What breaks when companies hit $50-100M in revenue?

In this episode:

• How Salesforce was able to forecast with 5% accuracy,
• The role of FP&A and CROs in go to market strategy and efficiency
• The issues with LTV to CAC ratio in SaaS
• Biggest challenges of the CFO/CRO relationship
• Bottoms up annual planning working with finance

Bobby Bray brings his perspective from more than 20 years in banking and consulting with Capital One, Oliver Wyman, and Regions Bank. The retired Navy Captain with four commands talks about strategic decision-making under pressure, working with Fortune 150 C-Suite executives, and the rigor required in FP&A.

He says: “To use an aviation term you need to be able to follow the drop of gas through the engine and understand the different cogs in the engine that turns a drop of gas into thrust, but it also is what turns raw data into usable analytics on the back end.” In this episode

• A Truly Non-Traditional Path to Finance
• Commercial banking as the most educational finance job
• Discipline and rigor in FP&A
• Cloud infrastructure changes in the past 7 years
• The rigor of a capital market stress test
• Explainability of AI in finance

Five-time CFO Rick Smith has led finance at companies including inVentiv Health Communications, Exos, Parchment, Solera Health before founding Bonfire advisory. He is also the author o fDemystifying the Role of the CFO in Venture and Growth Stage Companies, a no-nonsense approach to the topic. Reviews for the book include: “This book is a must-read if you want to understand how to scale a company as a CFO” and “Should be required reading for CEOs and PE people along with CFOs.”

In this episode Smith provides his take on being a CFO and his long background in FP&A, providing insights on:

• The path from FP&A to CFO (without a CPA)
• Why I like being CFO at SMBs (sub $50m)
• Being a dreamer, artist and buildingFP&A
• Audits vs QOEs
• The unspoken challenges working with PE firms
• FP&A and M&A – what you need to know

Link to the book: Demystifying the Role of the CFO in Venture and Growth Stage Companies

Preston Naegle started his career in private equity at Leavitt Equity Partners (founded by Michael Leavitt, the former U.S. Secretary of Health and Human Services. Negale then moved into the operating world and for more than 2 years has led strategic finance and FP&A at a PE-backed Midway Mechanical Services in the HVAC (Heating, Ventilation, and Air Conditioning) industry at the company which has completed 15 acquisitions (3 in 2025 alone) within the mechanical, electrical, and plumbing sector across the Western US region.

In this episode

• An origin story in Private Equity
• Learning from a “firehose” of business models
• Bringing PE thinking to a head of finance role at Midway Mechanical
• Bringing people with you as you create FP&A, budget and forecasting processes
• Choosing an FP&A solution
• Enhancing time to insights that bring long-term business partnering and profit growth

Glenn reconnects with Adam Shilton—who reveals the highs and lows of more than a decade selling to finance teams and what 134 deals in 36 months taught him about CFO challenges. The founder, writer, and speaker has now launched his own venture focused on helping entrepreneurs and solo business owners.

• My Experience selling finance software including SAP
• Bridging the Sales-Finance Divide: Why pipeline forecasts are inherently “fluffy”
• The Deposit Game-Changer: Why commission should only be paid on receipt of deposit, not just signature
• Finance coaching sales on overdue invoices AI and AR automation
• AI Agents workflows

What does it take to be the finance leader behind Hollywood stories? Diya Sagar, CFO of AWA Studios, which produces critically acclaimed, original stories for comics, TV, and movies, joins Glenn Hopper to reveal how she manages the money behind the magic—from funding graphic novels that may not pay off for years to navigating the unpredictable world of graphic novels, film and TV deals.

• How a “creator-first” approach shows up in budgets
• Building a Hits-Driven Portfolio
• The Ultimate Model: From Page to Screen Economics
• The 2-4 year timeline
• What Boards Really Want in a creative industry

With more than 20 years of experience helping startups scale from seed to series B, Maria Azatyan has built architectures for companies across ai, robotics and the new space economy, translating complex technologies into numbers. This is coupled with her frank perspective as a single mother balancing finance leadership and advising startups.

• Sci-fi Dreams Made Real: sharing experiences with Waymo
• Setting up ArmGate, empowering entrepreneurs
• One month to “two minutes” using AI to work with data
• Case study: AI to Automate ERA Filings for Venture Funds
• Role as ex-CFO at DocDoc.ru whose exit was ranked one of Russia’s top five IT & Digital M&A deals.
• Problems with cash flow to 45% year-over-year revenue growth
• Biggest startup challenges for finance teams