The Hurdle

In Season Two, Episode Three of The Hurdle podcast, Jade and Max sit down with Dustin Caldwell, owner of Old Dominion Collision Repair Center. Dustin shares his journey of taking over his family’s decades-old auto body repair business and transforming it into a thriving, specialized shop known for high-end and electric vehicle repairs. Dustin discusses the pivotal moments that shaped his success, including how joining a business peer group (“20 Group”) helped him increase profit margins and build a more sustainable operation. He dives into the power of reevaluating systems—challenging the “we’ve always done it this way” mindset—to drive efficiency and innovation. Lastly, he explains how offering ownership opportunities to key employees not only strengthened his team but also allowed him to step back from daily operations and focus on the bigger picture. Whether you’re an entrepreneur navigating industry shifts or a business owner looking to scale sustainably, Dustin’s insights provide a roadmap for growth, leadership, and long-term success. 🎙️ In this episode we discuss: (00:00) Welcome (00:47) Introducing Dustin Caldwell (01:27) Transitioning Ownership: A Family Affair (03:35) From Detailing to Management: Climbing the Ranks (08:22) Challenges in the Collision Repair Industry (13:14) Joining the 20 Group: Learning from the Best (15:45) Improving Efficiency and Overcoming Obstacles (19:45) The Ham Story: A Lesson in Questioning Processes (22:41) Challenging Longstanding Business Practices (24:41) Improving Accounts Receivable (26:47) Reevaluating Business Systems (30:08) Empowering Employees with Ownership (36:04) Lightning Round 🎧🚀 Discover more episodes of The Hurdle and get expert business tips on LivePlan’s blog: https://liveplan.com/blog ✋ Connect with Dustin & more LinkedIn: https://www.linkedin.com/in/dustin-caldwell-400b8b14 Instagram: https://www.instagram.com/olddomcollision Website: https://www.olddominioncollision.com 🧑‍💻 Resources mentioned in episode: The 7 Wastes of Lean: How to Optimize your Business for Growth: http://liveplan.com/blog/managing/reduce-waste-and-optimize-for-growth ✨ LivePlan socials & website: YouTube: https://www.youtube.com/@LivePlanApp Instagram: https://www.instagram.com/liveplan/ Facebook: https://www.facebook.com/liveplansoftware/ TikTok: https://www.tiktok.com/@liveplan.app LinkedIn: https://www.linkedin.com/showcase/liveplan/ Website: https://liveplan.com Newsletter & More: https://linkin.bio/liveplansoftware

In Season Two, Episode Two of The Hurdle podcast, Jade and Max sit down with Seth San Filippo, founder of Urban Lumber Co. and owner of Urban Hardwoods, to explore his journey from teenage hobbyist to the owner of two successful businesses. Seth shares how his weekend passion for crafting custom longboards evolved into thriving custom furniture companies and a tree service. He opens up about the bold decisions that shaped his path—including refinancing his house and launching his first commercial space at just 25. A pivotal moment with a design firm then sparked his shift from selling raw wood to creating custom furniture. Seth also reflects on the challenges of acquiring a company during COVID, merging cultures, and building a business that runs smoothly without his constant involvement. He discusses hiring a skilled team, learning to delegate, and planning for long-term success. Tune in for insights on growth, adaptability, and achieving a sustainable work-life balance. 🎙️ In this episode we discuss: (00:00) Welcome (00:43) Introducing Seth and his 1st Woodworking Business (01:13) Starting a Custom Longboard Business (02:26) Challenges Selling at a Market (03:24) Building a Website and Expanding Sales (05:02) From Skateboards to Salvaging City Trees (07:31) Acquiring a Crane Truck and Scaling Up (10:01) Transitioning to a Full-Time Wood Business (10:52) Buying a Commercial Space (13:38) Seth’s Pivot: Selling Wood to Custom Furniture (16:34) Sneaking into a High-End Showroom (18:33) Establishing Urban Lumber Company (21:13) Hiring and Growing a Team (25:06) Navigating Challenging Partnerships (26:33) Acquiring Urban Hardwoods in Seattle (31:22) Integrating Company Cultures (35:39) Balancing Work and Life 46:37 Lightning Round 🎧🚀 Discover more episodes of The Hurdle and get expert business tips on LivePlan’s blog! https://liveplan.com/blog ✋ Connect with Seth & more LinkedIn: https://www.linkedin.com/in/seth-san-filippo-26150399/ Instagram: https://www.instagram.com/urbanlumberco/ Websites: https://urbanlumber.co/ https://www.urbanhardwoods.com/ ✨ LivePlan socials & website Instagram: https://www.instagram.com/liveplan/ Facebook: https://www.facebook.com/liveplansoftware/ TikTok: https://www.tiktok.com/@liveplan.app LinkedIn: https://www.linkedin.com/showcase/liveplan/ Website: https://liveplan.com Newsletter & More: https://linkin.bio/liveplansoftware

In Season Two, Episode One of The Hurdle, Jade and Max talk to Eddie Rosenberg, an entrepreneur with a passion for sustainability and a knack for go-to-market strategy (GTM). Eddie shares his journey starting FUNNER, an eco-conscious surfboard company revolutionizing the industry with sustainable, repurposed materials and cutting-edge 3D printing technology. Eddie opens up about the challenges of transitioning from marketing expert to surfboard manufacturer and small business owner. He discusses learning manufacturing skills, prototyping boards, and balancing the drive for perfection with the need to launch and iterate. The conversation dives into creating a market-ready MVP, integrating customer feedback, and deciding whether to stay small or scale up—while weighing the trade-offs of seeking venture capital. With insights on GTM best practices, reflections on sustainability, and the ups and downs of bringing an innovative, 3D printed surfboard to life, this episode delivers valuable lessons and inspiration for entrepreneurs tackling their own hurdles. Tune in to hear Eddie’s story and how he’s riding the wave of innovation in the surf industry. 🎙️ In this episode we discuss: (00:00) Welcome (00:45) Introducing Eddie and His 3D Printed Surfboards (02:07) Eddie's Entrepreneurial Journey (04:55) The Birth of a Sustainable Surfboard Idea (07:27) Challenges and Innovations in 3D Printing (13:27) Building the Brand and Prototyping (26:31) MVP & Market Readiness (34:02) Launching the Product (36:55) The Launch Party: A Celebration of Support (37:34) Website Launch and Missed Opportunities (40:01) Post-Launch Plans (42:16) Customer Feedback and Customer Personas (46:45) Eddie’s Approach to Competition and Industry Collaboration (54:50) Scalability and Future Plans (01:02:50) Lightning Round 🎧🚀 Discover more episodes of The Hurdle and get expert business tips on LivePlan’s blog! https://liveplan.com/blog ✋ Connect with Eddie & more LinkedIn: https://www.linkedin.com/in/edrosenberg29/ Instagram: https://www.instagram.com/funner.surf/ Website: https://funner.surf 🏄‍♀️ Resources mentioned in episode Verdure Surf – New Zealand-based sustainable surfboard company: https://www.verduresurf.com ✨ LivePlan socials & website Instagram: https://www.instagram.com/liveplan/ Facebook: https://www.facebook.com/liveplansoftware/ TikTok: https://www.tiktok.com/@liveplan.app LinkedIn: https://www.linkedin.com/showcase/liveplan/ Website: https://liveplan.com Newsletter & More: https://linkin.bio/liveplansoftware

This week on The Hurdle, Jade and Max chat with Maxwell Richardson-Davis, the new owner of Lox, Stocks & Bagels, a popular spot for authentic boiled bagels. Maxwell shares his journey from managing the shop to buying it, rebuilding from financial chaos, and working 100-hour weeks to turn it into a thriving local favorite. We explore his creative rebranding efforts, operational challenges, and ambitious plans to expand with pop-ups, wholesale items, and new locations. Hear how Maxwell revived a struggling business, built a strong team, and achieved success through grit, determination, and community focus. Connect with Maxwell & More LinkedIn: / maxwelldavistheartist Facebook: / loxstocksandbagels Instagram: / loxstocksandbagels Website: https://loxstocksandbagels.com/ LivePlan Social & Website Instagram: / liveplan Facebook: / liveplan TikTok: / liveplan LinkedIn: / liveplan Website: liveplan.com Newsletter & More: linkin.bio/liveplansoftware Timestamps 00:00 Intro 00:29 Introducing Maxwell Richardson-Davis 02:17 How Maxwell Got Started in the Bagel Business 04:54 Securing the Right Investment 11:09 Learning the Ropes of Running the Business 17:39 Adjusting Operations for Success 21:34 The Importance of Administrative Organization 26:52 Struggles in the First Few Months 41:40 Growth & Strategic Challenges 46:03 Supplier Relationships & Cost Management 50:22 Focusing on Coffee & Beverages 53:32 Strategic Sellouts & Demand 58:46 Future Expansion Plans 01:09:00 The Lightning Round

Description: In this episode, Jade and Max sit down with Lauren Kelley, founder of Collie & Corso and a certified positive reinforcement dog trainer, to discuss her journey in the dog world and her path to becoming a small business owner. Driven by a passion for improving the lives of dogs—and their humans—Lauren ventured into both training and product creation, launching a dog training service and a business making stylish, durable leashes inspired by her own two dogs, Harvey and Veti. Lauren reflects on the challenges of going solo in her career, the financial realities of entrepreneurship, and her recent return to an employment role that balances both purpose and profit. Tune in for an honest look at Lauren’s unique path and what it takes to thrive in a passion-driven business. Connect with Lauren & more Instagram: / @collieandcorso TikTok: / @collieandcorso Website: https://www.collieandcorso.com Special discount code for Collie & Corso products for The Hurdle podcast listeners: Use code: ”THEHURDLE15” for 15% off any order. LivePlan Social & Website Instagram: / liveplan Facebook: / liveplan TikTok: / liveplan LinkedIn: / liveplan Website: liveplan.com Newsletter & More: linkin.bio/liveplansoftware Timestamps 01:28 - Introducing Lauren Kelley 04:07 - The Journey to Certification 07:58 - Lauren's Origin Story Helping Dogs 12:06 - From Dog Training to Leash Making 16:23 - Preparing To Scale From The Start 26:02 - Defining Lauren's Ideal Customer Profile & Brand 31:26 - Setting Prices & Profit Margins 40:04 - Dealing With Supplies & Limited Space 44:00 - Balancing Business & Market Demands 48:38 - The Challenges of Going Solo: Lessons Learned 57:25 - Expanding The Leash Business