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

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/

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LivePlan Social & Website

Instagram:/ liveplan 

Facebook: / liveplan

TikTok: / liveplan

LinkedIn: / liveplan

Website: liveplan.com

Newsletter & More: linkin.bio/liveplansoftware

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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

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

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.

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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

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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

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.