The Free to Grow CFO Podcast

Episode SummaryIn this episode of the Free to Grow CFO podcast, Jon Blair and Melissa Cafagna discuss the critical aspects of scaling a DTC brand with a focus on bookkeeping, accounts payable, and inventory management. They explore the challenges brands face in financial management, the importance of accurate financials for capital acquisition, and the common pitfalls in bookkeeping practices. The conversation also delves into the significance of understanding landed costs, the integration of AP with inventory management systems, and the impact of tariffs on DTC brands. A case study highlights how effective profitability analysis can lead to smarter business decisions.Key Takeaways-Integrating AP with inventory management systems improves accuracy.-Accurate financials are crucial for capital acquisition.-Effective financial management can alleviate stress for brand founders.-Landed costs must be tracked accurately to understand true profitability.Episode LinksJon Blair - https://www.linkedin.com/in/jonathon-albert-blair/Melissa Cafagna- https://www.linkedin.com/in/melissacafagna/ Free to Grow CFO - https://freetogrowcfo.com/Settle - https://www.settle.com/Meet Melissa CafagnaMelissa Cafagna is a passionate advocate for mission-driven brands, known for her customer-focused approach and her role as a 'financing fairy godmother.' With extensive experience in the financial industry, she is dedicated to helping small businesses grow through innovative and personalized financing solutions. While living in Europe for three years, Melissa transitioned from finance and accounting to sales, gaining cultural insights and developing a dynamic empathy that shapes her approach to building relationships. In her free time, she enjoys spending time with her family, exploring Chicago’s beautiful parks and city centers, and immersing herself in hip-hop and R&B music. About Settle Settle is the best way to power up your brand’s cash flow and operations—designed specifically for consumer brands ready to grow. With a unified platform tailored for 'finventory' management, you can seamlessly plan, purchase, manage, and pay for inventory, all in one place. Automate payments, 3-way match purchase orders, and real time accurate landed costs. For businesses that qualify, Settle Working Capital offers founder-friendly financing, so you can Settle now, pay later, and scale confidently. Join brands like Thread Wallets, Truvani, and Olipop to confidently scale for what's next. Learn more about Settle today.Transcript ~~~00:00 Introduction to the Free to Grow CFO Podcast02:03 The Importance of Bookkeeping in Scaling Brands07:58 Challenges in Financial Management for Emerging Brands13:59 Common Bookkeeping Issues Found in Brands19:56 Integrating Inventory Management with Financial Processes26:00 Streamlining Accounts Payable for Better Control27:20 Segregation of Duties in Accounting28:31 Understanding Landed Costs and Inventory Management Systems33:30 The Importance of Accurate Profitability Analysis39:29 Integrating AP with Inventory Management for Better Insights44:00 Navigating Tariffs and Their Impact on DTC Brands48:01 Case Study: Improving Profitability Through Data Analysis

Episode SummaryIn this mini-episode of The Free to Grow CFO Podcast, Jon Blair challenges a common misconception among DTC brand founders: that a profitable, cash-rich brand doesn’t need a CFO. Jon breaks down why these types of brands often need even more strategic financial support—especially if the goal is to build long-term wealth. It’s not just about managing ad spend and inventory. It’s about turning profits into smart capital allocation and sustainable wealth creation—both inside and outside the business.Key Takeaways:-Just because your brand is profitable and sitting on cash doesn’t mean you’re set. It may actually mean you’re flying blind without strategic guidance.-Wealth doesn’t just come from exits. It’s about using your brand’s cash to buy assets—stocks, real estate, maybe even other brands.-Profit is only powerful when it’s used well. A CFO helps you determine how much to reinvest in the business vs. how much to pull out to diversify your wealth.Episode LinksJon Blair - https://www.linkedin.com/in/jonathon-albert-blair/Free to Grow CFO - https://freetogrowcfo.com/

In this engaging discussion, Izzy Rosenzweig, Founder and CEO of Portless, shares insights on the evolving landscape of cross-border e-commerce. He highlights the significance of the Section 321 exemption and the challenges brands face with new import tax regulations. Izzy discusses strategies for maintaining cash flow and optimizing operations amidst changing tariffs, emphasizing the importance of adapting to global markets. He also delves into the role of trade lawyers and regulatory compliance, offering practical advice for brands looking to thrive in a competitive environment.

Episode SummaryIn this mini-episode of The Free to Grow CFO Podcast, Jon Blair breaks down a common mistake he sees in DTC brand financial strategy: relying on a blended ROAS target to guide monthly ad spend. While a blended ROAS might appear to show healthy contribution margins, it can actually mask losses on new customer acquisition—especially when repeat customer revenue is propping up the numbers.Jon walks through how to break down contribution margin by customer type and why attributing ad spend correctly is essential for truly understanding performance. This episode is a must-listen for founders who want to scale profitably and avoid misleading metrics.Key Takeaways:-Using a blended ROAS target can be misleading.-It's essential to separate new and repeat customer contribution margins.-Communicate specific targets for new customer acquisition to ad buyers.Episode LinksJon Blair - https://www.linkedin.com/in/jonathon-albert-blair/Free to Grow CFO - https://freetogrowcfo.com/

Episode SummaryIn this episode of the Free to Grow CFO podcast, Jon Blair and Keith Kohler discuss the intricacies of financing for DTC brands, focusing on the importance of understanding good versus bad debt, the journey of K2 Financing, and the common reasons consumer goods brands require debt. They explore risk assessment between inventory and accounts receivable, the nuances of revenue-based financing, and the critical factors beyond just cost of capital that founders should consider. The conversation also delves into maturity matching in debt financing, multi-layered debt strategies, and the essential diligence items needed for successful lender conversations.Key Takeaways-Capital is essential for scaling DTC brands.-Availability of capital can be more important than the cost of capital.-Multi-layered debt strategies can provide flexibility and growth opportunities.-Maturity matching is key to ensuring debt aligns with asset consumption.Episode LinksJon Blair - https://www.linkedin.com/in/jonathon-albert-blair/Keith Kohler - https://www.linkedin.com/in/keithkohler1/ Free to Grow CFO - https://freetogrowcfo.com/K2 Financing - https://www.k2financing.com/Meet Keith KohlerKeith Kohler is the Founder of The K2 Group LLC, a finance consultancy specializing in helping CPG founders secure the right financing at the right time™. He has originated and closed over $100 million in financing and authored the CPG Financing Guide, covering debt financing options for CPG companies at every stage. Keith also offers a 30-minute strategy call to help founders develop a 2-3 year financing plan.A sought-after speaker, Keith has led financing webinars for the Specialty Food Association, Hirshberg Entrepreneurship Institute, and Emerging Brands Summit. He created both CPG Financing Month, a series of conversations exploring the financing and mindset journeys of CPG companies, and the Making the Numbers Work® for You retreat (www.makingthenumbersworkforyou.com) where he helps founders overcome anything holding them back from the successful management of their business finances.Keith supports CPG founders in several other roles, including as a member of the selection committee of Nutrition Capital Network and a Wharton Venture Lab Expert in Residence and Mentor.Transcript ~~~00:00 Introduction to DTC Financing Challenges03:10 Understanding Good Debt vs Bad Debt05:57 The Journey of Keith Kohler and K2 Financing08:49 Common Reasons for Debt in Consumer Goods Brands11:44 Risk Assessment: Inventory vs Accounts Receivable14:58 Revenue-Based Financing and Its Implications18:06 Factors Beyond Cost of Capital21:11 Maturity Matching in Financing Strategies23:41 Navigating Multi-Layered Debt Strategies26:02 Understanding Debt Financing Options28:27 Capital Efficiency and Profitability29:20 The Role of Lenders in Growth32:51 Crafting the Perfect Pitch to Lenders38:54 Preparing for Debt Conversations42:48 Fun Facts and Closing Thoughts

Episode SummaryIn this episode of the Free to Grow CFO podcast, Jon Blair and Chris Pearson discuss the principles of profitable growth marketing for DTC brands. They explore the philosophy of Chris’s company, Three Beacon Marketing, emphasizing the importance of questioning traditional marketing practices and focusing on alignment through the North Star Strategy. The conversation delves into key metrics for growth, the interconnection of acquisition and retention, and the challenges brands face when scaling without repeat purchases. Chris shares insights on common mistakes in paid media strategies and the necessity of continuous testing in marketing efforts, ultimately highlighting the significance of retention marketing best practices.Key Takeaways-Acquisition and retention must work together for sustainable growth.-A strong testing process should never stop—it’s the key to long-term success.-The difference between growing and scaling? Profitable repeatable systems.-Don’t just listen to what customers say—watch what they actually do.Episode LinksJon Blair - https://www.linkedin.com/in/jonathon-albert-blair/Chris Pearson - https://www.linkedin.com/in/pearson-chris/Free to Grow CFO - https://freetogrowcfo.com/Three Beacon Marketing - https://threebeaconmarketing.com/Meet Chris PearsonChris Pearson is an email marketing strategist, retention nerd, and co-founder of Three Beacon Marketing.For years, he watched brands treat email like an awkward first date–too pushy, too desperate, or just completely ghosting their list. The result? Wasted potential, burned-out subscribers, and millions in lost revenue.Then, he discovered a way to turn email and SMS into a predictable, scalable sales machine–without sounding like a sleazy used-car salesman or blasting discounts until customers develop banner blindness. He calls it the Waypoint Email & SMS Strategy®, a system designed to make email & SMS feel less like spam and more like money in the bank.Now, Chris helps 8- and 9-figure brands stop treating their email list like an ex they only text when they need something and start turning it into their most valuable asset. His system has generated millions in additional revenue for businesses that finally want email & SMS to pull its weight.Chris lives in Windsor, CO, with his wife and their dog, Sylvie, who has no idea what email is but still gets more engagement than most brands. When he’s not optimizing retention strategies, he’s probably outside, lifting something heavy, or overanalyzing why people do the things they do.Transcript ~~~00:00 Introduction to Profit-Focused Growth Marketing02:02 The Rebel Agency Philosophy05:50 Understanding the North Star Strategy09:36 Key Metrics for Profitable Scaling15:10 The Importance of Repeat Purchases20:29 Building Sustainable Brands and Relationships24:31 Common Misconceptions in Paid Media27:07 The Importance of Testing in Scaling30:40 Understanding Customer Value and Retention35:20 The Role of Product in Retention Marketing38:42 Bridging Brand and Data in Retention Marketing40:22 Final Thoughts

Episode SummaryIn this episode of the Free to Grow CFO podcast, Jon Blair and Clay Banks discuss the essential strategies for successfully launching a new product in the e-commerce space. They emphasize the importance of customer discovery, the process of moving from concept to prototype, and the critical steps involved in sourcing and setting up a supply chain. The conversation also covers best practices for launching a product effectively, overcoming financial constraints, and the significance of maintaining strong relationships with customers and suppliers. Clay shares valuable insights from his extensive experience in product development and entrepreneurship, providing listeners with actionable advice to minimize risk and maximize success in their product launches.Key Takeaways-Customer discovery is crucial and should never stop.-Always aim to reduce risk before making capital investments.-Ensure every new product is designed for profitability upfront (not just market fit).-Continue learning by answering support emails and gathering real user feedback.Episode LinksJon Blair - https://www.linkedin.com/in/jonathon-albert-blair/Clay Bank- https://www.linkedin.com/in/claybanks/Free to Grow CFO - https://freetogrowcfo.com/InPaceLine - https://www.inpaceline.com/GloriLight - https://glorilight.com/Meet Clay BanksClay Banks is a seasoned entrepreneur and growth strategist with a proven track record of bringing ideas to market and scaling them to success. Over 23 years, he has co-founded or led eight companies, raising more than $7 million in seed and venture capital. Specializing in go-to-market strategy, Clay has successfully launched over 23 hardware and software products, driving their adoption across direct-to-consumer and B2B channels.In 2022, Clay achieved a successful exit, selling his equity position in HavenLock—best known for its appearance on ABC’s Shark Tank and features in Forbes, TechCrunch, and Entrepreneur—to a venture capital firm. Today, Clay focuses on advising and investing in early-stage startups and short-term rental properties, leveraging his expertise to help founders navigate growth and achieve market fit.Passionate about enabling visionary entrepreneurs, Clay offers mentorship and consulting in growth strategies, eCommerce scaling, and operational excellence. Outside of business, he’s a five-time Ironman, published author, and dedicated advocate for turning big visions into impactful results.Transcript ~~~00:00 Introduction to Product Launch Strategies06:48 The Importance of Customer Discovery17:05 From Concept to Prototype23:47 Transitioning to Sourcing and Supply Chain Management28:50 Building Relationships with Manufacturers37:24 Launching Like a Pro45:49 Overcoming Financial Constraints52:22 Key Takeaways and Final Thoughts

Episode SummaryThis week on the Free to Grow CFO podcast, we welcome back Tana Cofer, co-founder of Glitter Faced and RosieRai, alongside her husband and business partner, David Cofer. Together, they dive into the realities of launching a brand on Amazon, navigating Walmart, and leveraging emerging marketplaces to drive profitable growth.With DTC brands facing rising CAC on Meta and Google, alternative channels like Amazon, Walmart, and TikTok Shop offer a compelling way to reach new customers—if done right. Tana and David share their firsthand experience in scaling their own brand and guiding clients through marketplace strategy.Key Takeaways-Defining a strategy is crucial for measuring success in marketing efforts.-Best practices for launching on Walmart include simplifying the process and leveraging reviews.-The competitive landscape of e-commerce requires intentionality in spending.Episode LinksJon Blair - https://www.linkedin.com/in/jonathon-albert-blair/Tana Cofer- https://www.linkedin.com/in/tanacofer/David Cofer - https://www.linkedin.com/in/david-cofer/Free to Grow CFO - https://freetogrowcfo.com/RosieRai - https://rosierai.com/Glitter Faced - https://www.glitter-faced.com/Meet Tana CoferTana Cofer is the founder and CEO of RosieRai, an e-commerce growth agency focused on helping small to medium size businesses launch and scale profitably on any online Marketplace. With a passion for driving online business success, Tana leads her team in creating innovative strategies that deliver remarkable results for their clients. She is also a wife and mother of 3 children and enjoys spending her weekends in her jeep out in the Utah mountains. Learn more about RosieRai and request a free Amazon Account audit here: https://rosierai.com/contactMeet David CoferDavid Cofer is the CRO and Co-Founder of RosieRai, a marketplace growth agency focused on helping small to medium size businesses launch and scale profitably on Amazon, Walmart, Target and many more. David focuses on building great teams. He has built out the RoseRai team and many of their partnerships, working to create powerhouse relationships that work to propel RosieRai and their partners forward. He also loves reading and playing games with his family.Transcript ~~~00:00 Introduction to DTC Finance Myths02:33 The Journey of Glitterface and RosieRai07:08 The Value of Operator Experience in Consulting11:00 Strategies Tested on Glitterfaced15:05 Walmart's Growing Marketplace Opportunity18:34 Best Practices for Launching on Walmart24:00 Exploring Other Marketplaces Beyond Amazon and Walmart26:51 Challenges in Brand Growth on Marketplaces27:42 Target vs. Walmart: Market Positioning and Strategy30:47 Understanding Acquisition Costs Across Channels36:32 The Importance of Strategy in Marketplace Decisions39:52 Navigating Business as a Husband and Wife Duo43:00 Closing Thoughts

Episode SummaryIn this episode of the Free to Grow CFO podcast, Jon Blair and Jeff Lowenstein discuss common finance myths in the DTC (Direct-to-Consumer) world. They focus on three main myths: the necessity of a 13-week cash forecast, the need for overly granular financial projections, and the advantages of working with e-commerce specific firms over horizontal firms. The conversation emphasizes the importance of understanding the purpose behind financial models and forecasts, advocating for a more strategic and less rigid approach to financial planning in the e-commerce space.Key Takeaways-You Don’t Always Need a 13-Week Cash Forecast-Granularity in Financial Models Should Serve Decision-Making, Not Complexity-Ecom-Specific Finance Firms Deliver More Value Than Generalist FirmsEpisode LinksJon Blair - https://www.linkedin.com/in/jonathon-albert-blair/Jeff Lowenstein- https://www.linkedin.com/in/freetogrow-jeff/Free to Grow CFO - https://freetogrowcfo.com/Meet Jeff LowensteinJeff was previously leading M&A efforts at ecommerce aggregator Boosted Commerce where he was the 5th employee. He built processes across M&A, finance and operations to support rapid growth from 0 to 30 brands under management in 2.5 years.He previously co-founded and exited an app for Shopify merchants and spent time in the Strategic Finance departments of Etsy and Caesars Entertainment. Jeff holds a BA from the University of Pennsylvania and an MBA from Harvard Business School.He’s worked with hundreds of brands over his career and founded Free To Grow because of his passion for supporting entrepreneurs and helping them succeed. The analytical and financial tools he has developed over the years are specifically crafted for the modern consumer brand.Transcript ~~~00:00 Introduction to DTC Finance Myths01:29 Myth 1: The 13-Week Cash Forecast12:38 Myth 2: Need for Granular Financial Projections26:49 The Importance of Financial Modeling30:06 Myths in Financial Forecasting31:05 E-commerce vs. Horizontal Firms39:15 The Value of E-commerce Expertise44:57 Leveraging Network and Experience48:00 Closing Thoughts

Episode SummaryIn this episode of the Free to Grow CFO podcast, Jon Blair and Michael True discuss the intricacies of scaling DTC brands with a focus on marketing measurement. They explore the transition from traditional click-based attribution to marketing mix modeling, emphasizing the importance of understanding the relationships between various marketing channels. Michael shares his journey from the music industry to founding Prescient AI, a platform designed to provide insights into marketing performance across multiple channels. The conversation also touches on the challenges of measuring retail performance, the impact of iOS 14 on digital advertising, and the role of AI in enhancing marketing strategies.Key Takeaways-MMM is essential for brands expanding into omnichannel marketing with significant top-of-funnel spend.-Tools like Prescient AI can help scale profitably by uncovering relationships between channels that traditional attribution methods miss.-The future of marketing measurement lies in combining MMM with other tools to create a full picture of brand performance.Episode LinksJon Blair - https://www.linkedin.com/in/jonathon-albert-blair/Mike True - https://www.linkedin.com/in/michaeljtrue/Free to Grow CFO - https://freetogrowcfo.com/Prescient AI - https://prescientai.com/Meet Mike TrueMike True is the co-founder and CEO of Prescient AI, which provides AI-driven marketing mix modeling solutions for omnichannel brands. Prior to starting Prescient, Mike was responsible for helping clients of App Annie, IBM, and Oracle generate millions of dollars in revenue through the implementation of various artificial intelligence and analytics solutions.Transcript ~~~00:00 Introduction 05:48 Understanding Marketing Mix Modeling11:58 Navigating Post-iOS 14 Challenges18:11 Insights on Retail and Delayed Sales Data25:49 Understanding Diminishing Returns in Ad Spend32:02 Integrating Prescient AI into the Marketing Tech Stack38:07 Closing Thoughts