Podcast - Tremonte Financial

The Traversing Entrepreneurship Podcast

Traversing Entrepreneurship is a show for and about business owners in Traverse City, Michigan and beyond. In each episode, host Derek Dall’Olmo sits 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.

Recent Episodes:

067 Scaling Your Business and Mastering Social Media Strategy with Katie Brinkley

In this episode of Traversing Entrepreneurship, Derek Dall’Olmo interviews Katie Brinkley, founder of NextStep Social and Podcasting. They explore Brinkley’s journey from aspiring sports reporter to agency owner, how she scaled her business from a solo venture to a...

066 Burnout to Breakthrough: Randy Martinez’s Journey

In this episode of the Traversing Entrepreneurship podcast, Derek Dall’Olmo interviews Randy Martinez, a personal and cultural transformation specialist. Randy shares his journey from a successful corporate career to personal transformation, discussing the challenges...

065 Understanding Earned Media and Its Impact with Saul Marquez

In this episode of Traversing Entrepreneurship, Derek Dall'Olmo sits down with Saul Marquez, founder and CEO of Outcomes Rocket, to unpack what it really takes to go from a secure corporate healthcare job to building a thriving business. You’ll hear how Saul made the...

064 Change Your Weather: Leadership, Joy, and the Ripple Effect with Lisa Even

In this episode, Derek sits down with Lisa Even, a keynote speaker, bestselling author, and leadership coach known for her “Good Ripple Effect” philosophy. With roots in healthcare operations, Lisa now works with companies like ESPN, SHRM, and Disney to help leaders...

063 Balancing Family, Income & Impact: Molly Rose Speed’s Journey of Empowerment

In this inspiring episode, Molly Rose opens up about the real work of empowering individuals—especially women—who are trying to build a career without sacrificing family. She shares heartfelt stories from her program, the unexpected ways coaching changes lives, and...

062 Why Most Entrepreneurs Fail (and How to Avoid It) with Mark Osborne

What does it really take to build a business that scales and sells itself?In this episode of Traversing Entrepreneurship, Derek Dall’Olmo sits down with Mark Osborne, founder of Modern Revenue Strategies, to explore how systems, strategy, and clarity can turn chaos...

061 The Journey of Digital Marketing Expert Chris Shihadeh

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...

060 Motivation and Entrepreneurship… What an Epic Journey with Eric Stopper

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...

059 Navigating Entrepreneurship with Beau Eckstein

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,...