The Free to Grow CFO Podcast

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

Episode SummaryIn this episode of the Free to Grow CFO podcast, Jon Blair and KC Holiday discuss the challenges and strategies for scaling DTC brands, focusing on the importance of overcoming burnout, implementing effective systems, and the value of mentorship. KC shares his entrepreneurial journey, insights on the different types of burnout DTC CEOs face, and frameworks for improving efficiency and decision-making. The conversation emphasizes the significance of community and storytelling in business, encouraging leaders to embrace their roles as culture builders.Key Takeaways-Burnout can be categorized into upward, stagnant, and downward burnout.-Continuous improvement of systems is necessary as the business evolves.-Tenacity in initial problem-solving should be applied to all business areas. Scaling is fundamentally about removing constraints.-Decision-making should prioritize reversibility and impact.Episode LinksJon Blair - https://www.linkedin.com/in/jonathon-albert-blair/KC Holiday- https://www.linkedin.com/in/kcholiday/Free to Grow CFO - https://freetogrowcfo.com/Daily Mentor - https://dailymentor.co/Transcript ~~~00:00 Introduction 02:00 KC Holiday's Entrepreneurial Journey06:00 Understanding Burnout in DTC CEOs11:50 Frameworks for Overcoming Burnout17:43 Building Effective Systems and Processes23:51 The Importance of Focus and Prioritization24:40 Removing Constraints for Business Growth26:46 The Firefighter Analogy in Entrepreneurship28:08 Decision Making and Reversibility30:38 Forecasting Financial Outcomes34:23 The Importance of Mission and Values39:09 The Journey of Entrepreneurship and Community Support41:07 Closing Thoughts

Episode SummaryIn this episode of the Free to Grow CFO podcast, Jon Blair and Melissa Cafagna discuss the complexities of debt financing for DTC brands. They explore various debt options, including merchant cash advances, lines of credit, and SBA loans, while emphasizing the importance of choosing the right financing partner. Melissa shares her journey to Settle and how the company provides unique capital solutions tailored for eCommerce brands. The conversation highlights the critical role of fractional CFOs in navigating financial decisions and the significance of understanding inventory management in relation to capital needs.Key Takeaways-Over-leveraging or picking the wrong debt partner can jeopardize your business.-MCAs are often easy to access but come with high costs and risks to cash flow.-Debt isn’t inherently good or bad—it’s a tool. The key is choosing the right type for your specific stage of growth and strategy.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 COGS. 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 01:18 Melissa Cafagna’s Journey to Settle06:01 Understanding Debt Options for E-commerce Brands12:02 Evaluating the Pros and Cons of MCAs18:01 Understanding Asset-Based Lending (ABL)28:15 Navigating Cash Flow Challenges in E-commerce39:34 The Role of Fractional CFOs vs. Accountants44:37 Exploring SBA Loans and Their Limitations51:07 Closing Thoughts

Episode SummaryIn this episode of the Free to Grow CFO podcast, host Jon Blair and guest Clay Banks discuss the realities and misconceptions of starting and scaling an e-commerce brand. They explore the importance of enjoying the entrepreneurial journey, learning from failures, and the significance of simplicity in product development and marketing strategies. Clay shares insights from his entrepreneurial journey, including the rapid success of his brand GloriLight, and emphasizes the need for creativity and authenticity in marketing. The conversation also touches on the role of faith in entrepreneurship and the best practices for raising capital.Key TakeawaysSimplicity in product design leads to faster market entry.Invest in creativity to drive growth and attract investors.Understand your North Star metric to guide your business. Episode LinksJon Blair - https://www.linkedin.com/in/jonathon-albert-blair/Clay Banks- 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 02:14 Clay Banks' Entrepreneurial Journey08:25 The Pursuit of Freedom in Entrepreneurship19:17 Scaling GloriLight: Lessons Learned27:07 Simplicity in Product Development and Marketing27:33 Validating Product Assumptions Quickly29:24 Lessons from Past Failures in Marketing32:53 The Importance of Authentic Content Creation37:34 The Journey of Content Creation and Its Purpose38:45 Best Practices for Raising Capital44:09 The Role of Purpose in Brand Success51:35 Faith and Control in Entrepreneurship55:07 Closing Thoughts