The Free to Grow CFO Podcast

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

Episode SummaryIn this episode of the Free to Grow CFO podcast, Jon Blair and Chris Lang discuss the importance of holistic health for entrepreneurs. They explore the five F's: Faith, Family, Focus, Fitness, and Finances, emphasizing how each aspect contributes to a balanced and successful life. Chris shares his journey in entrepreneurship, the significance of maintaining focus, the role of fitness and nutrition, and the necessity of financial education. The conversation also touches on the importance of setting boundaries between work and personal life to achieve long-term success.Key Takeaways:-Faith is Foundational: Why understanding your "why" and living with intention impacts everything from decision-making to resilience.-Focus Wins the Day: Learn how eliminating distractions and playing to your strengths drives long-term success.-Finances for the Long Game: Insights on cash flow management and staying financially viable in a world of distractions.Episode Links:Jon Blair - https://www.linkedin.com/in/jonathon-albert-blair/Chris Lang- https://www.linkedin.com/in/chrislangsocial/Free to Grow CFO - https://freetogrowcfo.com/Move FWD - https://www.movefwd.co/Meet Chris LangChris Lang is a creative entrepreneur from Las Cruces, New Mexico. His focus on brand development and business strategy has helped launch multiple Shopify brands across the apparel, food, and wine industries, generating over 8 figures. Fresh Chile is now in the top 10% of all Shopify stores. He is working on donating over 1,000,000 meals to his community (currently 500,000).~~~00:00 Introduction 02:32 The Birth of Move FWD04:50 The Five F's of Life09:30 The Role of Faith11:54 Family Dynamics in Business14:46 The Importance of Focus22:02 Fitness and Mental Clarity26:21 The Impact of Processed Foods on Health28:38 The Importance of Nutrition and Sleep30:29 Long-Term Success in Business30:45 Understanding Finances in Business35:35 Learning from Financial Mistakes42:54 Setting Boundaries Between Work and Personal Life48:27 Closing Thoughts

Episode SummaryIn this episode of The Free to Grow CFO Podcast, Jon Blair sits down with AJ Stockwell, founder of Climb CFO and e-commerce accounting expert, to tackle one of the biggest challenges DTC brand founders face: keeping clean, accurate financials. Together, they dive into the essentials of bookkeeping for e-commerce brands, from spotting red flags to optimizing margins and ensuring financial clarity. Jon and AJ highlight a critical yet often overlooked mistake—misclassifying sales tax as revenue or expenses on the P&L statement. As AJ explains, sales tax is actually a liability, and including it on the P&L can seriously distort your brand’s financial health, impacting decisions around pricing, ad spend, and growth strategy. This episode is packed with insights to help founders maintain accurate records that drive smarter decisions.Topics Covered in Episode:-Biggest Red Flags in DTC Financials: Common errors in e-commerce bookkeeping that signal trouble.-Holiday Cash Flow Management: Why December’s slower sales and post-holiday tax liabilities require extra planning.-Landed Cost Accounting: Why it’s challenging for DTC brands and how to stay ahead with smart tracking of freight, duties, and fees.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/Meet AJ StockwellAJ Stockwell spent a decade as the CFO and Controller of numerous e-commerce brands, both in-house and on a fractional basis through his firm Climb CFO. More recently, he has shifted his firm's focus to accounting education and helping businesses clean up their books rather than providing ongoing CFO support.~~~00:00 Introduction 03:50 AJ Stockwell’s background05:51 The Importance of Accurate Bookkeeping12:01 Red Flags in Financial Statements30:22 Navigating Financial Complexity in E-Commerce36:43 The Importance of Accurate Costing Methods39:45 The Challenges of Landed Cost Accounting45:27 The Significance of Contribution Margin in Profitability50:21 Closing Thoughts

Episode SummaryIn this mini-episode of The Free to Grow CFO Podcast, Jon Blair discusses the critical importance of specialized bookkeeping for e-commerce brands, particularly those generating close to $10 million in revenue. He emphasizes the inadequacies of using a general CPA for bookkeeping, highlighting the need for expertise in e-commerce consumer goods. The short discussion covers the differences between cash and accrual accounting, the necessity for timely financial data, and the challenges posed by tax deadlines that can hinder bookkeeping efficiency.Key Takeaways:-E-commerce bookkeeping is complex and requires specialized knowledge.-Accrual accounting provides better visibility into cash flow management.-You need timely and accurate financial data for decision making.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 Jeff Lowenstein discuss the critical role of bookkeeping in scaling direct-to-consumer (DTC) brands. They highlight three warning signs that indicate poor bookkeeping practices, including the misclassification of sales tax, the absence of sales tax in financial statements, and the erratic swings in profit margins. Throughout the episode, Jon and Jeff stress the importance of having a clear understanding of your financial metrics and how they inform your decision-making process. They share real-world examples from their experiences with clients, illustrating the potential pitfalls of poor bookkeeping and the value of having a dedicated team that understands the nuances of e-commerce accounting.Key Takeaways:-Contribution margin is your real top-line revenue. Understanding it is key to profitability.-When you run your books on cash basis, you miss out on the true financial picture of your business.-Erroneous bookkeeping can lead to poor financial decisions.Episode 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.Timestamps00:00 Introduction 01:09 The Importance of Solid Bookkeeping Beyond $10 Million02:15 Warning Sign #1: Sales Tax on Your P&L08:34 The Impact of Poor Bookkeeping on Decision Making14:12 Warning Sign #2: Missing Sales Tax in Financials18:12 The Importance of Accrual Accounting in E-commerce22:40 Warning Sign #3: Wild Margin Swings Month Over Month33:04 The Role of Intentional Bookkeeping in E-commerce39:12 Closing Thoughts

Episode SummaryThis week on The Free to Grow CFO Podcast, Jon Blair is joined by Doug Schneider, COO of Heart & Soil, to discuss the challenges and strategies involved in scaling a direct-to-consumer (DTC) brand, particularly focusing on operational constraints, supply chain management, and the importance of leadership. Doug shares his journey from a biochemistry background to becoming the COO of Heart & Soil, emphasizing the significance of purpose-driven business and the need for strong relationships in supply chain operations. The conversation also touches on demand planning, inventory management, and the role of leadership in navigating hypergrowth.Key Takeaways:-Effective demand planning is essential for managing inventory.-Data-driven decision making helps reduce decision fatigue.-Strong relationships with suppliers can provide a competitive advantage.Episode LinksJon Blair - https://www.linkedin.com/in/jonathon-albert-blair/Doug Schneider- https://x.com/DTCDougFree to Grow CFO - https://freetogrowcfo.com/Heart & Soil - https://heartandsoil.co/Meet Doug SchneiderDoug Schneider is the COO of Heart & Soil Supplements. As a founding manager, he played a pivotal role in scaling the brand from $0 to $50M in just three years.Timestamps00:00 Introduction 02:36 Doug's Background and Journey to Heart & Soil10:12 The Importance of Purpose in Building a Brand14:41 The Role of Communication in Supply Chain Management23:11 Leadership and Its Impact on Business Growth35:14 Demand Planning Challenges During Rapid Growth50:12 Closing Thoughts

Episode SummaryIn this episode of the Free to Grow CFO podcast, Jon Blair and Jeff Lowenstein discuss the common mistakes DTC brands make while scaling from one to ten million in revenue. They emphasize the importance of inventory management, the impact of marketing agency fees, and the necessity of regular financial reviews. This conversation provides valuable insights for founders looking to navigate the complexities of scaling their businesses effectively.Key Takeaways:-It's better to risk stocking out than to overstock.-Monthly financial reviews are essential for tracking progress.-Understanding contribution margin is key to evaluating agency performance.Episode 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.Timestamps00:00 Introduction to Scaling DTC Brands01:21 The Badlands of Scaling: Key Mistakes02:50 Inventory Management: The Fear of Stockouts22:07 Marketing Agency Fees: Finding the Right Fit32:14 The Importance of Monthly Financial Reviews

Episode SummaryIn this episode of the Free to Grow CFO Podcast, Jon Blair sits down with Tim Clark, founder of The Retail RX, to chat about scaling D2C brands with a profit-focused mindset, particularly in the realm of Amazon growth strategy. Tim shares his entrepreneurial journey, insights on transitioning from Vendor Central to Seller Central, and the importance of leveraging tech tools and networking to drive growth. The conversation emphasizes the need for brands to adapt to the evolving e-commerce landscape and highlights the role of RetailRx in helping brands optimize their operations and profitability.Key Takeaways:-Leveraging tech tools can save time and improve efficiency.-Networking is crucial for staying updated in the e-commerce space.-Building relationships can lead to valuable business opportunities.-Businesses exist to turn a profit or else they're just hobbies.Episode LinksJon Blair - https://www.linkedin.com/in/jonathon-albert-blair/Tim Clark - https://www.linkedin.com/in/theretailrx/Free to Grow CFO - https://freetogrowcfo.com/Meet Tim ClarkTim has 25 years of experience selling products online across digital platforms including 15 years selling on Amazon. He has worked at startups helping them fuel profitable growth and has helped enterprise brands implement tech solutions to scale while streamlining efficiencies. Outside of revenue generation, Tim loves networking with good people and seeing young professionals grow in their careers.Timestamps00:00 Introduction to Profit-Focused Growth02:11 Tim Clark's Entrepreneurial Journey05:57 Transitioning to Amazon Growth Strategy09:59 Scaling Vendor Central Business12:35 The Shift to Seller Central19:37 Navigating Amazon's Complex Structure25:54 Leveraging Tech Tools for Efficiency34:41 The Importance of Networking45:36 RetailRx: Helping Brands Thrive55:37 Final Thoughts