Episode Player

Building Resilience Along the Entrepreneurial Journey

Bringing Up Business

Chapters
0:00
Resilience and the Entrepreneurial Journey
0:41
Introducing Samantha Masabny of The Woods Maine
2:03
Which Came First: Motherhood or Business?
3:39
The Untold Challenges of Early Motherhood
10:30
How Kids Can Inspire Us
11:52
Creating a Village
20:02
What Vulnerability Looks Like in Parenting & Business
31:27
The Benefits of Vulnerability
42:28
How Entrepreneurship Can Strengthen Us
47:01
Determining Your "Upstream vs Downstream"
54:14
Letting Go to Cultivate Your Power
1:10:23
Encouraging Entrepreneurship for Kids
1:14:15
Navigating New Parenthood with an Established Business
1:19:52
Top 3 Takeaways from This Conversation
1:20:14
Outro
Bringing Up Business
Building Resilience Along the Entrepreneurial Journey
Feb 24, 2026 Episode 26
Yumari Digital

Samantha Masabny, Co-Founder of luxury hospitality and retail brand The Woods Maine, discusses the essential qualities of entrepreneurs, emphasizing the importance of resilience and self-reflection. 

Samantha highlights that personal experiences shape one's ability to succeed in business and the necessity of confronting inner challenges to elevate one's brand or business.

--------------------

ABOUT SAMANTHA MASABNY

Samantha Masabny is an entrepreneur and community advocate, best known as Co-Founder of The Woods Maine. The luxury hospitality and retail brand celebrates Maine’s craftsmanship and culture. With a passion for revitalizing rural economies,Samantha has grown The Woods Maine from a boutique retreat in Norway, Maine, into a thriving brand that supports artisans and growing businesses. Under her leadership, The Woods Maine Shop has expanded from its flagship treehouse experience (crafted in collaboration with renowned builder Pete Nelson) into a retail and e-commerce destination. The shop curates high-end, Maine-inspired goods and partners with local makers to showcase the best of the region’s craftsmanship. Sam has built a trademarked brand identity from scratch, which includes adult and youth apparel, home decor, and accessories (most notably in collaboration with Chappy Wrap, Sea Bags, Nocs, and Boathouse Sports). Sam’s commitment to sustainability and small-business growth has made her a key figure in Maine’s tourism and retail sectors. 

Beyond The Woods Maine, Sam works with business owners and companies to refine their brand strategy and enhance customer experience. Drawing from her experience in sales, marketing, and business development — both as a business owner and her previous career at HubSpot — she helps entrepreneurs grow while staying true to their values. Whether guiding startups or established brands, her approach focuses on creating lasting impact for businesses and the communities they serve. 

Sam resides in Norway, Maine with her husband and Co-Creator of The Woods, Rob Masabny. When they are not building brands they love traveling with their 8 year old daughter, playing golf, and enjoying great food with friends and family.

--------------------

LINKS

The Woods Maine 

Send us Fan Mail

Save 10% on Unique Golf Bags by Omnix
Use code BUB on omnixgolfusa.com to save on the most unique golf bags and accessories.

Custom Apparel & Accessories by Virtue
Whether you're promoting your business or expanding your brand, Virtue has you covered.

Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.

Support the show

--------------------

📢 Support & Get a Business Shoutout!
https://www.buzzsprout.com/2426474/support

🎙️ Learn more about this show:
http://bringingupbusiness.com

📲 Send us a DM:
https://www.instagram.com/bub.podcast

💬 Text us:
https://www.buzzsprout.com/twilio/text_messages/2426474/open_sms

☕️ Buy us a coffee:
https://buymeacoffee.com/bubpodcast