Matt Lesser joins us to discuss the ups and downs entrepreneurs can face and the importance of resilience and support when navigating the unpredictable world of business. Matt is the Founder/CEO of Uniquely Normal, LLC, which exists to equip leaders to build flourishing organizations through empathy, 6the past 20+ years. Prior to launching Uniquely Normal, Matt owned and operated businesses, and served in several C-Suite roles across various industries.
Our conversation takes a deep dive into Matt’s entrepreneurial journey, detailing the challenges he faced when taking over his family’s oil business. From discovering over a million dollars in unpaid trade debt to dealing with the EPA and IRS, Matt shares how these obstacles led him to a dark place, both personally and professionally. With support from his family and a local businessman, Matt was able to rebuild the company and eventually pivot into the heavy oil industry, finding success and growth along the way.
“It’s okay to ask for help; nobody is meant to face everything alone.” – Matt Lessor
This week on Traversing Entrepreneurship:
- What’s the biggest contribution to GDP that family businesses make?
- Growing up in a family business and learning the business.
- The three biggest challenges Matt faced in his life.
- How business is different from business school.
- Working with leaders and developing healthy leaders.
- How do you build empathy, excellence, and excellence into the culture of your organization?
- What is it about family business that draws Matt to it?
- How do you create an environment where people can lean into what they’re passionate about and contribute value?
- When you talk about flourishing, do you see any commonalities between people who thrive and those who don’t?
- What’s the difference between employee achievement vs employee development?
Our Favorite Quotes:
“You can’t always control the hand you’re dealt, but you can choose how to play it.” – Matt Lessor
“Sometimes, the hardest decisions are the ones that lead to the most growth.” – Matt Lessor
“My darkest moments eventually became the catalyst for my greatest achievements.” – Matt Lessor
“Adapting to change is a key component of success in business and life.” – Matt Lessor
“Don’t be afraid to take a step back and reevaluate your goals and strategy.” – Matt Lessor
“In entrepreneurship, resilience is often more important than the initial idea.” – Derek Dall’Olmo
“There’s a lesson to be learned in every failure, if we’re willing to look for it.” – Derek Dall’Olmo
Connect with Matt Lessor:
About TreMonte and Traversing Entrepreneurship Podcast
Traversing Entrepreneurship is a show for and about business owners in Traverse City, Michigan and beyond. In each episode, co-hosts Derek Dall’Olmo and Melissa Niedzielski sit down with local business owners and the professionals who serve them to talk about business building, life, money, taxes, family — and all the ups and downs that come with doing something different. Join us to hear their stories and lessons learned — and to get inspired about what might be possible in your own business.
Derek and Melissa work together at TreMonte Financial Consultants, LLC and TreMonte TreMonte Tax Solutions, LLC (together referred to as “TreMonte”). TreMonte works with business owners and entrepreneurs to develop a proactive tax strategy that maximizes after-tax profits. It is TreMonte’s goal to bridge the gap between Financial Advisors and Accountants by serving as CFO to their clients.
This show is for informational purposes only and should not be viewed as personalized financial, investment, tax, or legal advice. You should always consult an attorney or tax professional regarding your specific legal or tax situation.
Please email Derek Dall’Olmo at derek@tremontefinancial.com with questions and comments or to schedule a one-on-one conversation.
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