The Free to Grow CFO Podcast

Jon Blair
  • 5.0 (10)
  • ENTREPRENEURSHIP

Welcome to the Free to Grow CFO podcast, your guide to scaling a DTC brand with a profit-focused mindset. Join us as we dive into insightful conversations with DTC and E-commerce experts, as well as visionary brand founders, sharing invaluable insights and strategies for success in the dynamic DTC landscape. Whether you're a budding entrepreneur or seasoned brand owner, tune in for actionable advice to elevate your business and achieve sustainable growth.

  1. 2D AGO

    Why Most DTC Brands Get Amazon Wrong

    www.FreeToGrowCFO.com 👇 GET ACCESS TO OUR FREE CASH FLOW 101 COURSE https://mailchi.mp/freetogrowcfo.com/ftg-cash-flow-course-sign-up 👇 GET A FREE CFO ANALYSIS https://freetogrowcfo.com/free-cfo-analysis 📧 JOIN OUR WEEKLY FREE TO GROW CFO NEWSLETTER https://freetogrowcfo.com/newsletter 🧔‍♂️ WHO IS FREE TO GROW CFO Outsourced CFO and Bookkeeping services for profit-focused DTC brands. Scaling a DTC brand is stressful. With messy books and no CFO on your team you run the risk of… -Hiring too quickly -Buying too much inventory -Scaling ad spend unprofitably -Running out of cash And that leads to stressful, sleepless nights. We don’t want that for you. Free to Grow CFO has given hundreds of DTC brands a plan for scaling alongside healthy profit and cash flow. Our plan will work for you too. 📈 WANT TO INCREASE PROFIT AND CASH FLOW AS YOU SCALE? Book a Call Now → https://freetogrowcfo.com/book-a-call 🤝 CONNECT WITH JON BLAIR ON LINKEDIN https://www.linkedin.com/in/jonathon-albert-blair/ 🎥 FOLLOW FREE TO GROW CFO ON YOUTUBE https://www.youtube.com/@FreetoGrowCFO 🎤 EPISODE DESCRIPTION If you’re a DTC founder who’s hesitant to launch on Amazon because you’re afraid it will cannibalize your website sales, this episode will challenge that assumption. In this episode of The Free to Grow CFO Podcast, Jon Blair and Alex Chiru break down what’s actually happening inside Amazon today — from intent-based search and AI-driven personalization to why ranking and momentum matter more than ever. We also unpack one of the biggest mistakes growing brands make: treating Amazon like a keyword game instead of a relevance and conversion engine. And finally, we zoom out to the CFO lens — why scaling too fast on Amazon without understanding your cash flow can put you in a dangerous position. Whether you’re already on Amazon or considering launching, this episode will give you a clearer framework for how to think about the platform strategically — not emotionally. Key Takeaways -Amazon usually adds incremental revenue rather than cannibalizing DTC sales. -Ranking improves when you generate conversions quickly after launch. -External traffic helps, but Amazon still rewards on-platform spend. -Search on Amazon is now intent-based, not just keyword-based. Episode Links Jon Blair - https://www.linkedin.com/in/jonathon-albert-blair/ Alex Chiru- https://www.linkedin.com/in/alexandru-chiru-44315941 Free to Grow CFO - https://freetogrowcfo.com/ Transcript ~~~ 00:00 Introduction to Alex Chiru and Trubuilt Automotive 01:23 Misconceptions About Selling on Amazon 09:36 Impact of Returns on Ranking and Momentum 14:34 Challenges for Established Brands 18:49 Debunking Myths in Amazon Scaling 19:33 The Reality of Running an Amazon Business 22:08 The Value of a Fractional CFO 25:11 Advice for DTC Brands Considering Amazon 27:28 Final Thoughts

    28 min

  2. FEB 12

    Mini Episode: What an Elite DTC CFO Can Do For You

    www.FreeToGrowCFO.com 👇 GET ACCESS TO OUR FREE CASH FLOW 101 COURSE https://mailchi.mp/freetogrowcfo.com/ftg-cash-flow-course-sign-up 👇 GET A FREE CFO ANALYSIS https://freetogrowcfo.com/free-cfo-analysis 📧 JOIN OUR WEEKLY FREE TO GROW CFO NEWSLETTER https://freetogrowcfo.com/newsletter 🧔‍♂️ WHO IS FREE TO GROW CFO Outsourced CFO and Bookkeeping services for profit-focused DTC brands. Scaling a DTC brand is stressful. With messy books and no CFO on your team you run the risk of… -Hiring too quickly -Buying too much inventory -Scaling ad spend unprofitably -Running out of cash And that leads to stressful, sleepless nights. We don’t want that for you. Free to Grow CFO has given hundreds of DTC brands a plan for scaling alongside healthy profit and cash flow. Our plan will work for you too. 📈 WANT TO INCREASE PROFIT AND CASH FLOW AS YOU SCALE? Book a Call Now → https://freetogrowcfo.com/book-a-call 🤝 CONNECT WITH JON BLAIR ON LINKEDIN https://www.linkedin.com/in/jonathon-albert-blair/ 🎥 FOLLOW FREE TO GROW CFO ON YOUTUBE https://www.youtube.com/@FreetoGrowCFO 🎤 EPISODE DESCRIPTION In this mini episode of the Free to Grow CFO podcast, Jon Blair breaks down the critical role of an elite DTC CFO in helping brands scale profit and cash flow. He emphasizes the importance of understanding the specific 'game' a brand is playing—whether it's high LTV, new customer dominant, or high SKU count—and how this influences financial strategies. Jon outlines the different requirements for profitability in each game and stresses that an elite CFO should provide strategic insights rather than just basic accounting services. Key Takeaways: -An elite DTC CFO goes beyond basic accounting tasks. -Identifying the game you're playing is crucial for strategy. -Each game has unique CAC targets and profitability requirements. Episode Links Jon Blair - https://www.linkedin.com/in/jonathon-albert-blair/ Free to Grow CFO - https://freetogrowcfo.com/ Transcript 00:00 Introduction to Elite D2C CFOs 00:20 Understanding the Role of an Elite CFO 01:17 Identifying the Game You're Playing 01:58 Strategies for Different Games 04:29 The Importance of Strategic Thinking in CFOs

    5 min

  3. FEB 5

    The Ultimate DTC Scaling Superpower: EOS

    www.FreeToGrowCFO.com 👇 GET ACCESS TO OUR FREE CASH FLOW 101 COURSE https://mailchi.mp/freetogrowcfo.com/ftg-cash-flow-course-sign-up 👇 GET A FREE CFO ANALYSIS https://freetogrowcfo.com/free-cfo-analysis 📧 JOIN OUR WEEKLY FREE TO GROW CFO NEWSLETTER https://freetogrowcfo.com/newsletter 🧔‍♂️ WHO IS FREE TO GROW CFO Outsourced CFO and Bookkeeping services for profit-focused DTC brands. Scaling a DTC brand is stressful. With messy books and no CFO on your team you run the risk of… -Hiring too quickly -Buying too much inventory -Scaling ad spend unprofitably -Running out of cash And that leads to stressful, sleepless nights. We don’t want that for you. Free to Grow CFO has given hundreds of DTC brands a plan for scaling alongside healthy profit and cash flow. Our plan will work for you too. 📈 WANT TO INCREASE PROFIT AND CASH FLOW AS YOU SCALE? Book a Call Now → https://freetogrowcfo.com/book-a-call 🤝 CONNECT WITH JON BLAIR ON LINKEDIN https://www.linkedin.com/in/jonathon-albert-blair/ 🎥 FOLLOW FREE TO GROW CFO ON YOUTUBE https://www.youtube.com/@FreetoGrowCFO 🎤 EPISODE DESCRIPTION Hypergrowth is exciting — but it also hides broken systems. In this episode of the Free to Grow CFO Podcast, Jon Blair sits down with Doug Schneider, COO of Heart & Soil, to unpack what it really takes to implement EOS (Entrepreneurial Operating System) inside a fast-scaling ecommerce brand. Doug shares how Heart & Soil grew from zero to $70M in annual revenue — and why “successful chaos” eventually becomes operational debt. They break down the EOS tools that created real traction, including Level 10 meetings, scorecards, Rocks, and the IDS issue-solving process that helps companies make problems go away for good. They also discuss the people side of EOS, why broken systems burn out good employees, and what founders should expect when implementing structure and accountability for the first time. If you’re scaling fast and feeling the cracks, this episode is a roadmap for building an operating system that can actually support growth. Key Takeaways -Growth without structure creates hidden operational debt -IDS is the difference between solving issues and recycling them -Meetings should drive decisions, not storytelling -EOS is a multi-year maturity process — not a quick fix Episode Links Jon Blair - https://www.linkedin.com/in/jonathon-albert-blair/ Doug Schneider- https://x.com/DTCDoug Free to Grow CFO - https://freetogrowcfo.com/ Heart & Soil - https://heartandsoil.co/ Transcript ~~~ 00:00 Introduction to EOS and Heart and Soil 04:35 The Importance of Implementing EOS 09:06 Unlocking Potential with L10 Meetings 13:36 The Issues Component of EOS 17:55 People Management in EOS 22:23 Overcoming Implementation Challenges 26:57 Final Thoughts and Advice

    33 min

  4. JAN 29

    *BONUS EPISODE* Ecom Scaling Show Ep10:How To Use A Variable Costing P/L And Why It Matters

    Episode Summary Welcome to the Ecom Scaling Show, brought to you by Free To Grow CFO and Aplo Group! Join hosts Jon Blair (Founder, Free to Grow CFO) and Dylan Byers (Co-founder, Aplo Group) as we dive into the crucial—yet often missing—link between marketing and finance in DTC e-commerce. In Episode 10, Jon and Dylan dive into the critical importance of structuring the chart of accounts for DTC brands. They emphasize the necessity of a variable costing P&L to understand contribution margins by sales channel. Learn about pitfalls related to vertical chart structures and misallocation of fixed costs, and why accurate data tracking and sales channel segmentation are essential. By the end of this episode, you’ll gain key insights into optimizing your P&L for more accurate forecasting and better financial management. Key Takeaways -Overhead allocation can distort profitability assessments. -Contribution margin dollars should be the primary focus. -Multi-channel businesses face unique challenges in profitability analysis. 00:00 Introduction and Importance of Restructuring the Chart of Accounts 00:18 Episode 10 Kickoff and Today’s Topic 00:53 Challenges with Current P&L Structures 03:31 Practical Issues in P&L Analysis 05:17 High-Level Chart of Account Strategy 09:32 Forecasting and Cost Allocation 17:32 Sales Channel Segmentation and Data Tracking 25:11 Final Thoughts on P&L Structure 27:12 Episode Conclusion Episode Links Free To Grow CFO: https://freetogrowcfo.com/ Aplo Group: https://www.aplogroup.com/ Jon Blair on Linkedin: / jonathon-albert-blair Dylan Byers on Linkedin: / dylan-byers-046010149

    27 min

  5. JAN 22

    Mini Episode: The E-commerce Gold Rush is Over

    www.FreeToGrowCFO.com 👇 GET ACCESS TO OUR FREE CASH FLOW 101 COURSE https://mailchi.mp/freetogrowcfo.com/ftg-cash-flow-course-sign-up 👇 GET A FREE CFO ANALYSIS https://freetogrowcfo.com/free-cfo-analysis 📧 JOIN OUR WEEKLY FREE TO GROW CFO NEWSLETTER https://freetogrowcfo.com/newsletter 🧔‍♂️ WHO IS FREE TO GROW CFO Outsourced CFO and Bookkeeping services for profit-focused DTC brands. Scaling a DTC brand is stressful. With messy books and no CFO on your team you run the risk of… -Hiring too quickly -Buying too much inventory -Scaling ad spend unprofitably -Running out of cash And that leads to stressful, sleepless nights. We don’t want that for you. Free to Grow CFO has given hundreds of DTC brands a plan for scaling alongside healthy profit and cash flow. Our plan will work for you too. 📈 WANT TO INCREASE PROFIT AND CASH FLOW AS YOU SCALE? Book a Call Now → https://freetogrowcfo.com/book-a-call 🤝 CONNECT WITH JON BLAIR ON LINKEDIN https://www.linkedin.com/in/jonathon-albert-blair/ 🎥 FOLLOW FREE TO GROW CFO ON YOUTUBE https://www.youtube.com/@FreetoGrowCFO 🎤 EPISODE DESCRIPTION In this mini episode of the Free to Grow CFO podcast, Jon Blair discusses the end of the e-commerce gold rush and the shift towards sustainable business practices for DTC brands. He emphasizes the importance of profitability, the role of a great CFO in executing wealth-building strategies, and the need for control over business operations and personal wealth creation. The conversation highlights the transition from a speculative market to one that rewards discipline and effective execution. Key Takeaways: -Profitability is essential for survival in the current market. -Brands must focus on sustainable growth rather than rapid scaling. -The era of easy money has passed, but disciplined wealth creation is possible. Episode Links Jon Blair - https://www.linkedin.com/in/jonathon-albert-blair/ Free to Grow CFO - https://freetogrowcfo.com/ Transcript 00:00 The End of the E-Commerce Gold Rush 02:17 Building Sustainable DTC Brands 03:58 The Role of a CFO in Modern Business 05:45 Strategic Wealth Creation for Founders

    7 min

  6. JAN 15

    Here Are The Places Your Books Are Broken (And How to Fix It)

    www.FreeToGrowCFO.com 👇 GET ACCESS TO OUR FREE CASH FLOW 101 COURSE https://mailchi.mp/freetogrowcfo.com/ftg-cash-flow-course-sign-up 👇 GET A FREE CFO ANALYSIS https://freetogrowcfo.com/free-cfo-analysis 📧 JOIN OUR WEEKLY FREE TO GROW CFO NEWSLETTER https://freetogrowcfo.com/newsletter 🧔‍♂️ WHO IS FREE TO GROW CFO Outsourced CFO and Bookkeeping services for profit-focused DTC brands. Scaling a DTC brand is stressful. With messy books and no CFO on your team you run the risk of… -Hiring too quickly -Buying too much inventory -Scaling ad spend unprofitably -Running out of cash And that leads to stressful, sleepless nights. We don’t want that for you. Free to Grow CFO has given hundreds of DTC brands a plan for scaling alongside healthy profit and cash flow. Our plan will work for you too. 📈 WANT TO INCREASE PROFIT AND CASH FLOW AS YOU SCALE? Book a Call Now → https://freetogrowcfo.com/book-a-call 🤝 CONNECT WITH JON BLAIR ON LINKEDIN https://www.linkedin.com/in/jonathon-albert-blair/ 🎥 FOLLOW FREE TO GROW CFO ON YOUTUBE https://www.youtube.com/@FreetoGrowCFO 🎤 EPISODE DESCRIPTION Most founders rely on the P&L to run their business. The real risks—and the real truth—live on the balance sheet. In this episode, Jon Blair sits down with AJ Stockwell, founder of Climb CFO, to break down how messy books quietly distort cash flow, margins, and decision-making in growing DTC brands. They unpack the most common red flags they see in cleanup projects—from cash-in-transit and merchant clearing errors to inventory mistakes that make gross margins meaningless. This conversation gives founders a practical framework for knowing when a cleanup is necessary, how to think about the ROI of fixing historical financials, and why accurate balance sheets are non-negotiable once a brand starts scaling or pursuing outside capital. What You'll Learn -The #1 red flag that signals revenue and cash are likely misstated -Why the balance sheet—not the P&L—is the fastest way to spot broken books -Why inventory is the hardest account to clean up (and the most dangerous to ignore) -The difference between light cleanups vs. heavy cleanups—and how to evaluate ROI Episode Links Jon Blair - https://www.linkedin.com/in/jonathon-albert-blair/ AJ Stockwell- https://www.linkedin.com/in/ajstockwell/ Free to Grow CFO - https://freetogrowcfo.com/ Climb CFO - https://climbcfo.com/ Transcript ~~~ 00:00 – Intro: Why Most Founders Miss the Real Financial Problem 02:35 – The #1 Red Flag: Why the Balance Sheet Matters More Than the P&L 05:50 – Merchant Clearing Accounts & Undeposited Funds Explained 07:00 – How Broken Balance Sheets Create Broken P&Ls 12:30 – Inventory Mistake #1: Zero Inventory on the Balance Sheet 13:45 – Inventory Mistake #2: Same Balance All Year Until December 17:45 – How to Rebuild Inventory History When Data Is Incomplete 18:45 – Light Cleanup vs. Heavy Cleanup: How to Think About ROI 20:15 – Why Lenders Start With the Balance Sheet (Not Your Story) 21:35 – What Founders Must Provide for a Successful Cleanup Project 22:50 – AR, AP, and the Working Capital Blind Spot 24:10 – Why “No AP” Is a Bigger Problem Than You Think 25:20 – Final Advice: When It’s Time to Stop Guessing and Clean the Books 26:10 – Where to Find AJ & Closing Thoughts

    27 min

  7. JAN 8

    Real DTC Stories: Scaling Chubbies to $100m+

    www.FreeToGrowCFO.com 👇 GET ACCESS TO OUR FREE CASH FLOW 101 COURSE https://mailchi.mp/freetogrowcfo.com/ftg-cash-flow-course-sign-up 👇 GET A FREE CFO ANALYSIS https://freetogrowcfo.com/free-cfo-analysis 📧 JOIN OUR WEEKLY FREE TO GROW CFO NEWSLETTER https://freetogrowcfo.com/newsletter 🧔‍♂️ WHO IS FREE TO GROW CFO Outsourced CFO and Bookkeeping services for profit-focused DTC brands. Scaling a DTC brand is stressful. With messy books and no CFO on your team you run the risk of… -Hiring too quickly -Buying too much inventory -Scaling ad spend unprofitably -Running out of cash And that leads to stressful, sleepless nights. We don’t want that for you. Free to Grow CFO has given hundreds of DTC brands a plan for scaling alongside healthy profit and cash flow. Our plan will work for you too 📈 WANT TO INCREASE PROFIT AND CASH FLOW AS YOU SCALE? Book a Call Now → https://freetogrowcfo.com/book-a-call 🤝 CONNECT WITH JON BLAIR ON LINKEDIN https://www.linkedin.com/in/jonathon-albert-blair/ 🎥 FOLLOW FREE TO GROW CFO ON YOUTUBE https://www.youtube.com/@FreetoGrowCFO 🎤 EPISODE DESCRIPTION In this episode, Jon Blair interviews Jon-Mark Craddock, the owner and CEO of La Matera, discussing his journey from being the first employee at Chubbies to running his own e-commerce brand. They explore the challenges of scaling businesses, the importance of proactive supply chain management, and the decision-making process behind self-fulfillment versus outsourcing. Jon shares insights on demand planning, financing through SBA loans, and the lessons learned as a business owner. The conversation emphasizes the need for adaptability and strategic thinking in the ever-changing landscape of e-commerce. Key Takeaways -Adaptability is key to surviving as a founder. -Self-fulfillment can save money but requires more time and effort. -The importance of proactive problem-solving in supply chain management. -Building a lean team can lead to operational efficiency. Episode Links Jon Blair - https://www.linkedin.com/in/jonathon-albert-blair/ Jon-Mark Craddock- https://www.linkedin.com/in/jonmarkcraddock/ Free to Grow CFO - https://www.freetogrowcfo.com/ La Matera - https://lamaterashop.com/ Transcript ~~~ 00:00 Introduction to Jon Mark Craddock and His Journey 03:14 Scaling Challenges in E-Commerce 05:58 Proactive Supply Chain Management 09:06 Self-Fulfillment vs. 3PL: Making the Right Choice 12:05 Tech Tools for Fulfillment Operations 14:53 Demand and Replenishment Planning Insights 17:48 The Importance of Flexibility in Business Planning 20:42 Reflections on Lamatera and Future Goals 23:26 The Drive to Entrepreneurship 25:53 Financing the Business Purchase 36:52 Transitioning from Operator to Owner 42:03 Navigating Challenges as a Founder 43:44 Expanding Fulfillment Services

    42 min

  8. JAN 1

    *BONUS EPISODE* Ecom Scaling Show Ep9: Amazon Pitfalls, Scaling Past $10M on Shopify, and Attributio

    Episode Summary Welcome to the Ecom Scaling Show, brought to you by Free To Grow CFO and Aplo Group! Join hosts Jon Blair (Founder, Free to Grow CFO) and Dylan Byers (Co-founder, Aplo Group) as we dive into the crucial—yet often missing—link between marketing and finance in DTC e-commerce. In this episode, Jon and Dylan dive into the complexities of measuring Amazon, ad spend performance across different sales channels, and combining all of it with your DTC strategy. They discuss the challenges of attribution, the importance of considering cross-channel effects, and the strategies for optimizing ad spend to maximize overall contribution margin. Key points include the necessity of having separate KPIs for each channel, the potential pitfalls of launching on Amazon, and how to ensure collaboration between different agencies managing various aspects of a brand’s online presence. Key Takeaways -Attribution is always imperfect, but it's essential to analyze it. -Continuous scrutiny of ad spend can reveal wasteful expenditures. -Effective merchandising strategies can help brands maintain a DTC focus while on Amazon. 00:00 Introduction and Setting the Scene 0:58 Challenges of Attribution in Multi-Channel Marketing 02:04 Importance of Cross-Channel Attribution 03:45 Amazon vs. DTC: Common Scenarios and Strategies 04:16 Financial Insights and Unit Economics 06:52 Measuring Performance Across Channels 09:10 Strategies for Amazon and DTC Integration 17:35 Merchandising Strategies for Amazon 22:20 Scaling Without Repeat Purchases 28:20 Collaboration Between Agencies 30:41 Conclusion and Final Thoughts Episode Links Free To Grow CFO: https://freetogrowcfo.com/ Aplo Group: https://www.aplogroup.com/ Jon Blair on Linkedin: / jonathon-albert-blair Dylan Byers on Linkedin: / dylan-byers-046010149

    33 min
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Ratings & Reviews

5
out of 5
10 Ratings

About

Welcome to the Free to Grow CFO podcast, your guide to scaling a DTC brand with a profit-focused mindset. Join us as we dive into insightful conversations with DTC and E-commerce experts, as well as visionary brand founders, sharing invaluable insights and strategies for success in the dynamic DTC landscape. Whether you're a budding entrepreneur or seasoned brand owner, tune in for actionable advice to elevate your business and achieve sustainable growth.

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