Jon Blair
The Free to Grow CFO Podcast
Welcome to The Free to Grow CFO Podcast, where we dive deep into conversations about scaling a profitable DTC brand. Join us as we talk with DTC and Ecommerce experts, operators, and brand founders to uncover the strategies, financial insights, and real-world lessons behind sustainable growth. Whether you’re building toward your first million or scaling beyond eight figures, each episode is packed with practical advice to help you grow smarter and more profitably.
Where to listen?
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Episodes
Here Are The Places Your Books Are Broken (And How to Fix It) 15.01.2026 27:04
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...
Real DTC Stories: Scaling Chubbies to $100m+ 08.01.2026 41:43
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...
BONUS EPISODE: Ecom Scaling Show: Amazon Pitfalls, Scaling Past $10M on Shopify, and Attribution Challenges (Ep. 9) 01.01.2026 33:01
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 di...
BONUS EPISODE: Ecom Scaling Show: Fixed Costs & Hiring Mistakes To Avoid as an E-Commerce Brand(Ep. 8) 26.12.2025 41:26
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 of the Ecom Scaling Show, we’re diving into the biggest mistakes brands make when approaching hiring and fixe...
Scaling a Bootstrapped Brand - The Hulken Story 18.12.2025 25:10
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 Founder's True Story: Scaling and Selling a DTC Brand 11.12.2025 35:45
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...
Wealth Building and Tax Strategy for eComm Brand Founders 04.12.2025 40:32
Episode Summary In this episode of the Free to Grow CFO podcast, host Jon Blair speaks with Rolando and Raul Lopez of CFO Associates about the intersection of tax strategy and wealth building for e-commerce brand founders. They discuss the importance of proactive tax planning, the benefits of real estate investment, and the nuances of various retirement accounts. The conversation also covers entit...
BONUS EPISODE: Ecom Scaling Show: How To Plan & Budget For Growth In DTC (Ep. 7) 27.11.2025 37:01
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 delve into the intricacies of growth planning over a multi-year timeframe, emphasizing the imp...
Can An SBA Loan Help Your DTC Brand Scale? 20.11.2025 50:42
Episode Summary In this episode of the Free to Grow CFO Podcast, Jon Blair and Roxann Burns delve into the intricacies of SBA loans, exploring their benefits, criteria, and common misconceptions. Roxann shares her extensive experience in SBA lending, emphasizing the importance of understanding cash flow and structuring debt appropriately for business growth. They discuss the nuances of using SBA l...
Mini Episode: The Biggest Failure I See in Business Planning - Don't Make This Mistake 13.11.2025 4:43
Episode Summary In this mini episode of the Free to Grow CFO Podcast, Jon Blair discusses the critical importance of effective business planning, emphasizing that planning should not be an exercise in prediction but rather in understanding the cause and effect relationships between inputs and outputs. He highlights the risks associated with aligning business inputs around predicted outputs and adv...
How AI Is Changing DTC Forever - Are You Ready? 06.11.2025 47:56
Episode Summary In this episode, Jon Blair interviews Justin Mitchell, a seasoned content creator and entrepreneur, discussing the transformative impact of AI on e-commerce and content creation. They explore misconceptions about AI, practical applications for e-commerce brands, and the importance of data in understanding customer behavior. Justin shares insights on content strategies, the long-ter...
BONUS EPISODE: Ecom Scaling Show: Marketing Metrics and Their Relationship To Debt (Ep. 6) 30.10.2025 34:24
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 delve into the intricate relationship between marketing metrics and debt in the context of DTC...
What’s Working & What’s Flopping in DTC - 2025 23.10.2025 43:14
Episode Summary In this episode of the Free to Grow CFO podcast, Jon Blair and KC Holiday discuss the current trends in e-commerce, emphasizing the importance of product quality, effective offer testing, and understanding customer needs. They explore the dynamics between first-order dominant brands and those with high lifetime value (LTV), as well as the significance of leadership and company cult...
From Family Farm to 8-Figure DTC Brand 16.10.2025 38:56
Episode Summary In this episode of the Free to Grow CFO podcast, Jon Blair interviews Anna Brakefield, founder of Red Land Cotton, discussing the challenges and triumphs of scaling a direct-to-consumer brand while managing manufacturing in the U.S. They explore the importance of storytelling in marketing, the complexities of supply chain management, and the balance between family life and entrepre...
Mini Episode: What an Elite Finance Team Can Do For Your Brand 09.10.2025 6:40
Episode Summary In this mini episode of the Free to Grow CFO Podcast, Jon Blair discusses the essential functions of a finance team for DTC brands, emphasizing the importance of providing value in the scaling journey. He outlines the key monthly processes that finance teams should implement, including a 15-day close, monthly financial reviews, and strategic meetings with the CFO to ensure informed...
The True Cost of Fulfillment: How to Protect Margins Amid Rising Carrier Rates 02.10.2025 31:12
Episode Summary In this episode of the Free to Grow CFO podcast, Jon Blair and Tony Runyan discuss the current challenges in the logistics and e-commerce sectors, focusing on tariffs, mid-year carrier rate changes, and strategies for managing cash flow and inventory. They explore the implications of bonded warehousing and the importance of understanding the total cost of fulfillment. The discussio...
BONUS EPISODE: Ecom Scaling Show: How Much Should You Pay Yourself As An E-Commerce Brand Owner? (Ep. 5) 25.09.2025 28:45
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 of the Ecom Scaling Show, Jon and Dylan discuss how much money business owners should pull out of their e-com...
The Leadership Practices of Elite DTC Brands 18.09.2025 36:41
Episode Summary In this episode of the Free to Grow CFO podcast, Jon Blair and Dusty Holcomb discuss the critical role of leadership in scaling businesses profitably. They explore the chaos that often accompanies growth and the importance of clarity and purpose in navigating this chaos. Dusty shares insights on self-leadership, the significance of delegating outcomes rather than tasks, and the nec...
Mini Episode: Why 13 Week Cash Planning is a Waste of Time 11.09.2025 4:39
Episode Summary In this mini episode of the Free to Grow CFO Podcast, Jon Blair challenges the dogma surrounding 13-week cash forecasts for DTC brands. While most fractional CFOs swear by them, Jon argues that they’re often unnecessary and waste valuable time. Instead, he shares a more efficient, decision-driven approach to cash forecasting that prioritizes practicality over tradition. Whether you...
The Burnout Trap of Success (And How to Escape It) 04.09.2025 37:09
Episode Summary In this episode of the Free To Grow CFO podcast, Jon Blair and Matt Kyser discuss the intersection of business growth, leadership, and holistic health. They explore the importance of balancing various aspects of life, including work, family, and spiritual well-being, to achieve success and fulfillment. Matt shares his entrepreneurial journey and a framework for effective leadership...
BONUS EPISODE: Ecom Scaling Show: Merchandising Your Ad Account For DTC Brands (Ep. 4) 28.08.2025 37:21
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 of the Ecom Scaling Show, Jon and Dylan delve into the intricacies of merchandising in e-commerce, focusing o...
Why Your Ads May Not Be as Profitable As You Think 21.08.2025 39:47
Episode Summary In this episode of the Free to Grow CFO podcast, Jon Blair and Karl O'Brien discuss the common misconceptions surrounding the profitability of advertising in e-commerce. They explore the importance of understanding unit economics, the distinction between new and returning customer profitability, and the critical role of customer lifetime value (LTV). The conversation highlights the...
Mini Episode: A Million Dollar Secret That Only the DTC Scaling Elite Know About 14.08.2025 5:28
Episode Summary In this mini episode of the Free to Grow CFO podcast, Jon Blair discusses the concept of risk-adjusted bets in the context of scaling Direct-to-Consumer (DTC) brands. He emphasizes the importance of having a great CFO who can help businesses make calculated risks that limit downside while maximizing potential upside. The conversation covers how CFOs can assist in sizing bets, struc...
Should Your Brand Be Using an ERP? 07.08.2025 34:04
Episode Summary In this episode of the Free to Grow CFO podcast, host Jon Blair speaks with Kyle Hency, co-founder and CEO of Good Day, about his journey from finance to building successful consumer brands and software solutions. They discuss the challenges of scaling DTC brands, the importance of product development, and the unique approach Good Day takes in providing ERP solutions tailored for e...
How to Find Cash Hidden in Your DTC Brand 31.07.2025 42:27
Episode Summary In this episode of the Free to Grow CFO podcast, Jon Blair and Ben Tregoe discuss the importance of extracting cash from DTC brands to build wealth. They explore performance finance, the significance of margins and capital cycles, and the complexities of inventory management. The conversation emphasizes the role of repeat purchases in scaling businesses and the necessity of effecti...
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