The Hurdle

LivePlan
  • 5.0 (1)
  • ENTREPRENEURSHIP

Welcome to "The Hurdle," where entrepreneurship meets inspiration. Hosted by Jade and Max, this podcast is brought to you by the makers of LivePlan, software for business planning and financial forecasting. Join Jade and Max as they chat with everyday entrepreneurs who share unfiltered experiences overcoming the hurdles of starting and growing a business. From battling financial setbacks to navigating unexpected challenges, our guests offer practical advice, inspiring stories, and actionable insights. Tune in to hear firsthand how real entrepreneurs are turning obstacles into opportunities and discover how you can tackle your own business hurdles with confidence.

Episodes

  1. Outdated Systems, Outdated Growth—How Dustin Upleveled His Family’s Business

    04/02/2025

    Outdated Systems, Outdated Growth—How Dustin Upleveled His Family’s Business

    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

    43 min
  2. Building, Scaling and Acquiring Businesses with Seth San Filippo

    03/03/2025

    Building, Scaling and Acquiring Businesses with Seth San Filippo

    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

    51 min
  3. Prototyping a 3D Printed Surfboard?! Eddie Rosenberg’s Journey

    02/03/2025

    Prototyping a 3D Printed Surfboard?! Eddie Rosenberg’s Journey

    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

    1h 10m
  4. Buying & Rebuilding a Business w/ Maxwell Richardson-Davis

    12/20/2024

    Buying & Rebuilding a Business w/ Maxwell Richardson-Davis

    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

    1h 14m
  5. Balancing Purpose & Profit: Lauren Kelley's Entrepreneurship Journey

    12/11/2024

    Balancing Purpose & Profit: Lauren Kelley's Entrepreneurship Journey

    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

    1h 8m
  6. Brewing Success: How Angela McDonald Grew Her Tea Business Against the Odds

    11/22/2024

    Brewing Success: How Angela McDonald Grew Her Tea Business Against the Odds

    In this episode of The Hurdle, Jade and Max talk with Angela McDonald about her inspiring journey as the owner of Oregon Tea Traders. In honor of National Women’s Small Business Month, we’re highlighting Angela’s story of resilience and determination. With no prior business experience, Angela purchased the small tea company to maintain her connection to India and Tibet. In 2015, she made the leap to run the business full-time, overcoming fears and challenges while balancing life as a mom. Angela shares how she pivoted during the pandemic from wholesale to online sales and navigated hurdles in opening her first retail store in 2023. From construction delays to managing expectations, she turned the space into a flexible storefront and warehouse. Looking ahead, she plans to expand into bagged teas, grow online, and teach tea classes. Tune in for Angela’s honest advice on slow growth, minimizing risk, and building a business that aligns with your values. Her story is a powerful testament to perseverance and passion! Connect with Angela & More LinkedIn: / angela-mcdonald-76728b53 Instagram: / oregonteatraders Facebook: /oregonteatraders Website: https://oregonteatraders.com/ ----- LivePlan Social & Website Instagram:/ liveplan  Facebook: / liveplan TikTok: / liveplan LinkedIn: / liveplan Website: liveplan.com Newsletter & More: linkin.bio/liveplansoftware ----- Timestamps 00:00 Brewing Success w/ Angela McDonald 00:31 Introducing Angela McDonald 01:53 Angela's Background: From Anthropology to Tea 12:17 Buying the Business: Challenges and Learning Curves 19:02 Early Business Struggles: Sales & Processes 22:56 Navigating Retail: Market Challenges 33:49 Lessons Learned: Adapting & Growing 52:06 Business Management Program Experience 01:02:57 Hiring the First Employee 01:10:21 Moving to a Commercial Space 01:20:01 Navigating Regulations & Inspections 01:26:48 Future Plans & Reflections 01:30:36 The Lightning Round

    1h 36m
  7. Building Adventure: Mom Turns $11k into Thriving Children’s Museum

    10/25/2024

    Building Adventure: Mom Turns $11k into Thriving Children’s Museum

    In celebration of National Women's Small Business Month, we are thrilled to feature Amelia Reising, the founder and executive director of Adventure! Children’s Museum in Eugene, Oregon. Amelia’s nonprofit journey began in 2015 when she and a group of fellow moms envisioned a space where children could engage in art, history, and creative play. What started with pop-up events has grown into a beloved community museum with over 90,000 visitors last year. In this episode, Amelia shares her entrepreneurial story, from launching Adventure! Children’s Museum with just $11,000 to navigating the challenges of running a nonprofit. We explore the hurdles she faced, including fundraising, finding a permanent location, and growing the museum through community-driven initiatives. Amelia also reflects on the imposter syndrome she experienced while managing a half-million-dollar budget, her approach to financial sustainability, and her vision for expanding the museum. Tune in for insights on leading a nonprofit, overcoming challenges, and staying true to your mission—even when faced with uncertainty. Amelia’s inspiring journey is a testament to the power of persistence, community, and creativity. Join us as we dive into how Amelia turned a simple idea into a thriving nonprofit that serves children and families around the region. Connect with Amelia LinkedIn: / amelia-reising-563153b Facebook: / adventurechildrensmuseum Instagram: / adventurechildrensmuseum Websites: https://adventurechildrensmuseum.org Social & Website Instagram: / liveplan  Facebook: / liveplan TikTok: / liveplan LinkedIn: / liveplan Website: liveplan.com Newsletter & More: linkin.bio/liveplansoftware Timestamps:  00:49 - Introducing Amelia Reising 02:36 - Amelia's Career Journey & Inspiration 03:55 - The Birth of Adventure Children's Museum 11:50 - Pop-Up Exhibits & Community Engagement 24:08 - Fundraising & Financial Challenges 31:53 - Navigating Zoning & Safety Regulations 33:06 - Opening Day Challenges 35:06 - Handling Frustration & Burnout 43:05 - COVID-19's Impact on the Museum 45:08 - COVID-19 Pivot 50:00 - Re-opening After COVID-19 52:04 - Future Plans & Personal Growth 58:20 - The Lightning Round

    1h 1m
  8. Thomas Pettus-Czar on Values-Driven Entrepreneurship

    10/02/2024

    Thomas Pettus-Czar on Values-Driven Entrepreneurship

    Join us for an insightful conversation with Thomas Pettus-Czar, an entrepreneur from Eugene, Oregon, as he shares his entrepreneurial journey. From launching The Barn Light, dubbed the "first bar for 30-year-olds" in Eugene, to establishing a coffee roastery and navigating the franchise landscape, Thomas offers a candid look at the challenges and triumphs of entrepreneurship. In this episode, Thomas emphasizes the importance of aligning business decisions with personal values and the necessity of maintaining a healthy work-life balance. He reflects on the initial struggles of opening a business and the strategies he employed, such as leveraging Kickstarter for fundraising and implementing an employee investment program that empowers his team to pursue their own entrepreneurial dreams. We dive into the intricacies of selling his business, including the decision to hire a business broker and the pros and cons of that choice. Thomas also discusses his experience with franchise ownership, highlighting the value of working with a franchise representative to find the right opportunity. Tune in for valuable insights on building meaningful relationships, navigating the ups and downs of entrepreneurship, and the rewards of staying true to your values. Whether you're an aspiring entrepreneur or simply curious about the business world, this episode is packed with inspiration and practical advice. -- Connect with Thomas & More LinkedIn: / thomas-pettus-czar-4686a4aa Instagram: / farmersunionroasters Websites: https://www.farmersunioncoffee.com/co... https://tempwallsystems.com/locations... References: The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living by Ryan Holiday -- Timestamps 00:00 Bar, Beans, and… Walls? 00:32 Introducing Thomas Pettus-Czar 00:43 Thomas' Entrepreneurial Journey Begins 04:57 Leaving Grad School and Starting The Barn Light 07:05 The Challenges & Rewards of Opening The Barn Light 09:26 Choosing The Opening Day and Utilizing Kickstarter 12:08 The Value of Relationships 21:08 Supporting Employee Ventures 24:25 Opening a Second Location & Pursuing Vertical Integration 29:18 Closing The Barn Light 31:17 The Role of a Business Broker in Selling a Business 35:28 The Origin of The Farmers Union 39:50 Timing, Luck, and Unexpected Opportunities 41:26 The Ultimate #DadMove: Transitioning into Franchise Ownership 47:04 The Value of Using A Franchise Rep 52:22 The Concept of Temporary Wall Systems 55:49 Challenges with a New Franchise Business 59:09 What's Next for Thomas 01:01:03 Lightning Round

    1h 6m
  9. Mike White's Journey from Teen Hustler to Inspiring Innovator

    09/05/2024

    Mike White's Journey from Teen Hustler to Inspiring Innovator

    In episode one of "The Hurdle," Jade and Max sit down with the dynamic Mike White, a serial entrepreneur from Salem, Oregon, whose journey is anything but ordinary. From his teenage days hustling knock-off designer purses and dabbling in a pyramid scheme to becoming the visionary behind an award-winning BBQ sauce brand, Mike’s entrepreneurial path is as diverse as it is inspiring. Today, Mike is not just the proud owner of his hometown’s oldest diner, White's Restaurant, and a Barre3 franchise co-owned with his wife. He also spearheads an angel fund dedicated to nurturing emerging entrepreneurs and has launched impactful ventures in the social sector. Tune in for a conversation about embracing innovation, taking risks, and making a meaningful impact.

    1h 5m
  • 9 Episodes

About

Welcome to "The Hurdle," where entrepreneurship meets inspiration. Hosted by Jade and Max, this podcast is brought to you by the makers of LivePlan, software for business planning and financial forecasting. Join Jade and Max as they chat with everyday entrepreneurs who share unfiltered experiences overcoming the hurdles of starting and growing a business. From battling financial setbacks to navigating unexpected challenges, our guests offer practical advice, inspiring stories, and actionable insights. Tune in to hear firsthand how real entrepreneurs are turning obstacles into opportunities and discover how you can tackle your own business hurdles with confidence.

Information

  • Creator
    LivePlan
  • Years Active
    2024 - 2025
  • Episodes
    9
  • Rating
    Explicit
  • Copyright
    © LivePlan
  • Show Website
    The Hurdle