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Originators: An Entrepreneurial Podcast

Oct 19, 2022

Lisa Cloutier and Brian Anderson are the husband-and-wife founders and owners of The Whistling Andy Distillery, Montana’s oldest operating distillery that prides itself on producing award-winning spirits and giving back to the community of Montana.


Lisa Cloutier has been in the hospitality industry for over 25 years and has founded several businesses, including a small boutique hotel and The Raven, a Caribbean-style restaurant located on the waterfront of Flathead Lake at Bigfork, Montana. In addition to her functions as Co-founder, Lisa serves as the Marketing Manager of The Whistling Andy. She graduated from The George Washington University, where she majored in Political Science and International Relations.


Brian Anderson serves as a distiller and the Director of Operations at The Whistling Andy. He graduated with a Bachelor of Science degree in Geohydrology from Montana State University-Bozeman. After working in the environmental and geotech industries, Brian decided to transition to the world of entrepreneurship and join Lisa in expanding their businesses and founding new ones.


Lisa and Brian join me today to describe their journey as a married couple and business partners. They discuss their backgrounds, their beginnings as entrepreneurs, and how they decided to work together as business partners. They provide insight into running a business as a couple and how The Whistling Andy and their other businesses have evolved over the years. They also highlight the importance of balance in relationships, explain why taking trips together is important to them as a couple, and underscore what continues to inspire them to expand their businesses.


“Our businesses are entwined with our daily lives—even when we’re entertaining, it tends to be involved with employees or customers. We mix and match between our personal and business lives, and it all ties in together.” - Lisa Cloutier


This week on Originators:


  • How Brian and Lisa met, and their journey as entrepreneurs
  • Lisa’s background and ventures into hospitality and entrepreneurship
  • Brian’s background and how he started having the entrepreneurial itch
  • How they pushed their personal and professional relationship and build more businesses together
  • The similarities between marriage and business partnerships
  • Managing business-related burnout as a couple
  • The characteristics of successful leaders
  • The day-to-day of running businesses as a couple
  • The importance of balance in relationships, whether it’s in business or marriage
  • The evolution of Whistling Andy and what continues to drive them to expand their businesses


Our Favorite Quotes:


  • “You have to lead in a certain way, and there will be times where you have to sacrifice for your business.” - Zak Leedom
  • “Others’ perceptions can creep into your mind, but what matters is how the two of you operate internally and with each other and how you communicate—both from a leadership and marriage perspective.” - Zak Leedom
  • “The hardest parts are right before you open a business. The key is to get through those moments as a couple and ensure that you’re kind to each other.” - Brian Anderson


Connect with Lisa Cloutier:



Connect with Brian Anderson:



Connect with The Whistling Andy:



About WealthSource and The Originators Podcast


Originators is a show for and about entrepreneurs. In each episode, host Zak Leedom sits down with business builders and the professionals who serve them to talk about the challenges and the opportunities that come with starting something new. Our guests explore what it means to be a successful founder, a good leader, and an effective executive — and whether it’s possible to do all three. Join us to hear their stories and lessons learned — and to get inspired by their tenacity and creativity.


Zak Leedom works for WealthSource, an independent financial advisory firm with offices across the US. All opinions expressed by Zak are his own opinions and do not reflect the opinions of WealthSource. This podcast should not be relied upon for financial decisions. 


Email Zak Leedom at with questions, comments, and to schedule a one-on-one conversation. 


Follow Zak on LinkedIn.


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