loader from loading.io

Episode 34 - Matt Lesser Returns to Discuss the Pillars of Empathy, Empowerment, and Excellence in Leadership

Traversing Entrepreneurship

Release Date: 11/14/2023

The Journey of Digital Marketing Expert Chris Shihadeh show art The Journey of Digital Marketing Expert Chris Shihadeh

Traversing Entrepreneurship

This week, Derek sits down with Chris Shihadeh, CEO of Skylab Digital, who shares his entrepreneurial journey, insights on navigating the competitive Medicare space, and the importance of financial literacy in business. Chris discusses the significance of building a strong team, identifying A, B, and C players in hiring, and empowering employees to solve problems. He emphasizes the role of data in digital marketing, managing cash flow in seasonal businesses, and leveraging debt for growth. The conversation concludes with key takeaways for aspiring entrepreneurs, highlighting the importance of...

info_outline
Motivation and Entrepreneurship... What an Epic Journey with Eric Stopper show art Motivation and Entrepreneurship... What an Epic Journey with Eric Stopper

Traversing Entrepreneurship

In this episode of Traversing Entrepreneurship, Derek Dall’Olmo interviews Eric Stopper, an e-commerce expert and investor, to explore the highs and lows of entrepreneurship. From his early ventures in nanotechnology to his current success with Profitable, Eric shares candid insights into the challenges and triumphs of building a business. Discover how meditation, self-reflection, and a focus on family have shaped his journey. Key Moments: Eric's transition from nanotechnology to e-commerce and investing.  The importance of self-discovery and meditation in entrepreneurship.  How...

info_outline
Navigating Entrepreneurship with Beau Eckstein show art Navigating Entrepreneurship with Beau Eckstein

Traversing Entrepreneurship

In this episode Derek sits down with Beau Eckstein, owner of Business Ownership Coach and Emerge Lending Group. With over 26 years of experience, Beau shares his journey from a struggling student to a successful entrepreneur, offering insights into funding strategies, franchise consulting, and the importance of tax strategies. Discover how Beau's experiences, including a stint on HGTV, have shaped his approach to business and life. Key Topics: Beau's entrepreneurial journey and early challenges  The role of SBA loans and franchise consulting in business growth  Insights into tax...

info_outline
Navigating Entrepreneurship with Kasim Aslam show art Navigating Entrepreneurship with Kasim Aslam

Traversing Entrepreneurship

Join host Derek as he sits down with Kasim Aslam, founder of Solutions 8, to explore the highs and lows of entrepreneurship. Kasim shares his journey from humble beginnings to building a successful Google ad agency, discussing the importance of talent acquisition, the impact of AI on business, and the lessons learned from his failures and successes. Key Takeaways: Kasim's unique approach to hiring and retaining top talent.  Insights into the Pareto Principle and its application in business.  The role of AI in shaping the future of entrepreneurship.  Personal stories of...

info_outline
Helping Your Team Dream Bigger with Kate Volman show art Helping Your Team Dream Bigger with Kate Volman

Traversing Entrepreneurship

In this episode, Derek chats with Kate Volman—CEO, speaker, and big believer in helping people dream bigger. From her early days at the Chamber of Commerce to leading Floyd Consulting, Kate shares what she’s learned about people, growth, and the messy (but rewarding) work of leadership. They talk about the real stuff—why most business problems are actually people problems, how leaders can create space for personal dreams at work, and why being creative isn’t optional anymore. Whether you lead a team or are part of one, this is the kind of conversation that makes you pause and think...

info_outline
Building a Business That Works for You with Sarah Noel Block show art Building a Business That Works for You with Sarah Noel Block

Traversing Entrepreneurship

Derek sits down with Sarah Noel Block, the brains behind Tiny Marketing and the Tiny Marketing Club—a go-to resource for indie consultants who want smart, simple marketing that actually drives business (without the overwhelm). They unpack Sarah’s journey from the corporate world to building a business on her own terms. You’ll hear how she turned a layoff during the recession into a springboard for entrepreneurship, how she ditched the agency grind for a membership model, and why she believes less but better is the future of marketing. This one’s packed with real strategies—like...

info_outline
Navigating the Entrepreneurial Journey with Corey Morris show art Navigating the Entrepreneurial Journey with Corey Morris

Traversing Entrepreneurship

In this episode of the Traversing Entrepreneurship podcast, Derek Dall'Olmo interviews Corey Morris, founder of Voltage Digital Agency. They discuss Corey's journey from employee to business owner, the intricacies of digital marketing, particularly SEO, and the challenges and strategies involved in business acquisitions.  Corey shares insights on leadership, the importance of transparency in negotiations, and how he has personalized his agency's approach to better serve clients. In this conversation, Corey Morris discusses the evolution of his marketing agency, Voltage, emphasizing the...

info_outline
Navigating the Emotional Rollercoaster of Entrepreneurship with Brian Smith show art Navigating the Emotional Rollercoaster of Entrepreneurship with Brian Smith

Traversing Entrepreneurship

In this episode of the Traversing Entrepreneurship podcast, host Derek Dall'Olmo sits down with Brian Smith, an entrepreneur who’s seen it all—from humble beginnings washing boats and launching a college photography business to navigating the highs and lows of real estate. Brian’s story is one of grit, growth, and ultimately, reinvention. Burnout pushed Brian to make a life-altering decision: selling his businesses and stepping back to reassess his purpose. That pivotal moment led him to coaching and founding the Founders Organization, where he now helps fellow entrepreneurs thrive....

info_outline
Navigating the Private Credit Landscape: Mike Shum's Journey show art Navigating the Private Credit Landscape: Mike Shum's Journey

Traversing Entrepreneurship

In this episode of Traversing Entrepreneurship, Derek Dall'Olmo sits down with Mike Shum, CEO of Cascade Debt, to unpack his journey from derivatives trader to fintech founder. Mike opens up about the risks, missteps, and breakthroughs that shaped Cascade’s rise in the private credit space. They dive into how alternative credit scoring is reshaping lending, what most people get wrong about asset-based finance, and why economic shifts are forcing innovation in fintech. If you're building in the world of money—or thinking about it—this conversation is packed with firsthand insight.  ...

info_outline
From Forest Service to Global Visa with Rob Lee show art From Forest Service to Global Visa with Rob Lee

Traversing Entrepreneurship

This week on Traversing Entrepreneurship, Derek sits down with Rob Lee, co-founder and CEO of Swiss Passport and Visa Services, a company that expedites passports and obtains visas. Rob and his wife, Lori, started the business 17 years ago after living in Central America and encountering a need for such a service. Initially relying on paid ads, they shifted focus to business partnerships, particularly with Fortune 500 companies in the aviation, legal, and manufacturing sectors. They are now developing a software application to streamline travel document management. Rob emphasizes the...

info_outline
 
More Episodes

Matt Lesser started his career leading his family’s struggling business. It quickly failed, and Matt experienced a suicidal depression. Out of the ashes, a new business emerged and grew from three people to nearly two hundred while experiencing a twenty-fold increase in revenue, before selling to trusted competitors. Matt then served in a C-Suite role in private equity for 12 years, before serving transitional C-Suite roles in banking and commercial uniforms.

 

Matt founded Uniquely Normal, LLC in 2021 to equip leaders to solve their costly people-related challenges by building flourishing organizations on the pillars of Empathy, Empowerment, and Excellence, which is the focus of Matt’s second book, "unEngaged: Building Flourishing Organizations" (released 24 OCT 2023). Matt is the best-selling author of "unSatisfied: When Less is More" and has served as a keynote speaker as well as a facilitator of rooms packed with leaders around the world for more than twenty years now. In addition, Matt is a certified executive coach as well as certified in nearly twenty personality, preference, and leadership assessments. Matt married his elementary school sweetheart in 1996 and lives in northeast Indiana with his family.

 

Derek Dall'Olmo welcomes Matt Lesser back to the podcast to discuss Matt's new book on building flourishing organizations. Matt provides an overview of the three pillars of empathy, empowerment, and excellence that are the focus of his book. He explains each pillar in detail and how they contribute to developing engaged team members. Derek digs into how leaders can implement these concepts within their own organizations.

"Organizations do not become flourishing by accident. People do not become flourishing by accident. It requires intentionality." - Matt Lesser

 

This week on Traversing Entrepreneurship:

  • Building a successful business and overcoming challenges.
  • Leadership book with three pillars of empathy, empowerment, and excellence.
  • Leadership, empathy, and effective communication in business.
  • Empathy in leadership and its impact on employee retention.
  • Empowering employees with clear expectations and authority.
  • Leadership, empathy, and excellence in an organization.
  • Organizational excellence and team member motivation.
  • Identifying and developing top performers in an organization.
  • Acquisition strategies and addressing core fears and insecurities.



Our Favorite Quotes:

 

"Empathy really boils down to two things, two practices, understanding and listening." - Matt Lesser

"Empowerment is all about letting people do the job that you hired them to do." - Matt Lesser

"Excellence is having a compelling vision that is aligned, supported, and communicated." - Matt Lesser

 

Connect with Matt:

 

 

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.

 

TreMonte Facebook Page | Follow Derek on LinkedIn | Follow Melissa on LinkedIn

 

Subscribe:

Apple Podcast  |  Google Podcasts  |  Amazon Podcasts  |  Stitcher  |  Spotify  |  Deezer  |  TuneIn 

 

If you enjoy the show, please leave a review on iTunes to help others discover the podcast.