Derek Dall'Olmo

Traversing Entrepreneurship

Business EN ↓ 68 episodes

Traversing Entrepreneurship is a show for business owners who set out to do something different — and did not stop there. Join us as host Derek Dall'Olmo sits down with entrepreneurs and business owners in Traverse City and beyond to hear their stories, dig into the wins and challenges along the way and uncover what it takes to be successful, in business and in life.

Author

Derek Dall'Olmo

Category

Business

Latest episode

Jun 4, 2026

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Episodes

Fearless Finances: Empowering Women to Achieve More with Jenna Biancavilla 10.09.2024

Jenna Biancavilla, a multipreneur, joins me in this episode to discuss her journey from pre-med to finance, highlighting her dynamic career shift due to a career assessment. She founded Pearl Capital in 2016, aiming to provide unbiased financial advice. Jenna also launched Savvy, a tech company vetting financial advisors, and an online masterclass, Elevate Your Wealth. She emphasizes the importanc...

Stealth Consulting: Guiding Entrepreneurs Through the Chaos with Wesley J. Mathews 22.08.2024

In this episode, I sit down with Wes Matthews, the CEO and co-founder of Stealth Consulting. Wes shares his journey from the corporate world to the entrepreneurial realm, and how he's now helping other entrepreneurs succeed through his fractional CMO services. Learn about the power of the EOS system, the importance of finding the right team, and Wes' advice for those looking to start or grow their...

Overcoming Adversity Through Mindfulness and Entrepreneurship with Dr. Allen Lomax 25.06.2024

Dr. Allen Lomax joins Derek to share his personal journey of overcoming struggles and setbacks through mindfulness, empathy, and personal growth. They discuss their experiences in real estate investing, including strategies for raising capital and sourcing properties, and the importance of relationships and validation. They also explore the challenges of providing affordable housing in rapidly gro...

Episode 40 - Automating Your Business to Create Growth and Personal Freedom with Matt Clark 11.06.2024

Derek Dall'Olmo interviews Matt Clark to discuss his experiences in leveraging AI and automation to build successful B2B marketing businesses. They emphasized the importance of finding the right people to hire and train, and highlighted the need for high-quality clients and the challenges faced by car dealerships in the current market. They also discussed their approaches to scaling sales and lead...

Episode 39 - Entrepreneurship, Learning Challenges, and Environmental Stewardship with Gerald Rosengarten 28.05.2024

This episode highlights the career journey of entrepreneur Gerald Rosengarten, from developing leisure suits to real estate projects, with an empire in solar energy. Gerald discusses his experience with dyslexia and efforts to help others with learning disabilities. The discussion provides advice on entrepreneurship, highlighted bureaucratic challenges, and generated action items around advocacy a...

Episode 38 - Saying No to Make Room for Yes: Prioritizing Values Over Profits in Business with Josh Traeger 14.05.2024

In this episode Josh Traeger joins Derek Dall'Olmo to discuss his experience starting a law practice in Traverse City, Michigan. They share their perspectives on the challenges and rewards of starting a business in a small town, emphasizing the importance of community involvement and personalized service. They also discuss legal standards and procedures in military courts, and the difficulties and...

Episode 37 - Articulating Your Vision: Helping Entrepreneurs Plan for Success with Natasha E Davis 20.02.2024

Natasha E. Davis, affectionately known as "The Chief Visionary" is the CEO and founder of Impact Branding Consulting, Inc. and the CRM software platform The Profit Enhancer Analysis. Natasha specializes in positioning the daily operations of corporations and government agencies to perform in alignment with the vision of the leader through strategic planning and branding. Her specialty is helping e...

Episode 36 - Overcoming Entrepreneurial Fears with Dr. Tonya Robertson 23.01.2024

Dr. Tonya Robertson, the learning and strategy specialist is the Founder and CEO of Focused Training Solutions, a company that is committed to curating instructional learning tools designed to optimize performance in the workplace. Dr. Robertson has worked with numerous C-Suite Executives of well-known companies to create training materials that will guide their team to success and establish good...

Episode 35 - From Corporate Job to Land Investor: Nolan Miracle's Unconventional Path to Success 28.11.2023

Nolan Miracle is the founder and owner of The Property Miracle, LLC, a raw land investment company.  Since founding the business in January of 2021, Nolan and his team have acquired nearly 40 properties and have generated hundreds of thousands of dollars in profits.  With a national remote business model, they've bought and sold land all over the country from the comforts of their desks.   Nolan M...

Episode 34 - Matt Lesser Returns to Discuss the Pillars of Empathy, Empowerment, and Excellence in Leadership 14.11.2023

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...

Episode 33 - Asking the Universe and Taking Action with Martin Salama 24.10.2023

For over a decade Martin Salama, The Architect of The Warrior's L.I.F.E. Code has been helping entrepreneurs shift from worry and lack to abundance and being a L.I.F.E. Warrior! Why spend your time worrying when you can be Living Incredibly Full Everyday!   In this episode Martin Salama shares his journey of overcoming bankruptcy and divorce to become a successful life coach and author. He discuss...

Episode 32 - Exponential Digital Growth with Michael Begg 10.10.2023

Michael Begg is the Co-Founder and CEO of AMZ Advisers, a global digital marketing agency with locations in North America, Asia and Europe that provides Amazon services for brands and manufacturers looking to maximize their growth. Services include Amazon SEO, Advertising, Inventory Management, Marketing Strategy and Performance Reporting.   This episode features Michael Begg, an expert in e-comme...

Episode 31 - Gospel Roots: A Non-Traditional Approach to Music Education with Marshall White 26.09.2023

Marshall White, is CEO and founder of Unity Performing Arts Foundation and Director/Life Coach for the Voices of Unity Youth Choir. Marshall has three children Markeyta, Kamia, and Evan White and a stepson Chad Blackmon. He is married to Cynthia White. Mr. White has been shaping and molding young lives for more than 30 years. He is an accomplished musician, music and vocal coach, choral director s...

Episode 30 - Trading Energy, Words, and Wisdom with Mike Zaccardi 12.09.2023

Mike Zaccardi, CFA, CMT, provides expertise on analyzing investments and writing on personal finance, in addition to occasionally teaching at the University of North Florida. He loves to communicate financial information in a down-to-earth, easy-to-understand way. While he enjoys crunching the numbers and analyzing portfolios, Mike always keeps a focus on what it means for clients.   In this episo...

Episode 29 - The Return of Matt Hodges! Winning Strategies in a Cutthroat Real Estate Market 22.08.2023

Matt Hodges is the Managing Broker and Owner of Kultura Real Estate. With over 16 years of experience, he specializes in residential listings and purchases in the greater Grand Traverse region. Matt is an industry leader, currently serving as a Director on the Michigan Association of Realtors Board of Directors. Matt has also served on Aspire North Realtors Board of Directors, the local associatio...

Episode 28 - Introducing Alex Repo + NIL (Name, Image, Likeness) 08.08.2023

In this episode we welcome Alex Repo, the newest member of the TreMonte team! Hear Alex's story about how he went from working in a factory, to eventually serving as Derek's caddy and ultimately joining the TreMonte family. We discuss the impact of NIL deals in college, highlighting the newfound opportunities for athletes to monetize their personal brand. We keep the conversation fun and lighthear...

Episode 27 - Realtor Success Secrets with Kellie Sergent 25.04.2023

Kellie Sergent is a realtor based in Northern Michigan. Before becoming a realtor, Kellie worked in parks and recreation where she found the opportunity to combine three of her passions: people, community, and making an impact. Today, as a realtor for CENTURY 21, Kellie remains passionate about creating community by helping people find their perfect home, dream vacation retreat, or business ventur...

Episode 26 - The Five Pillars of Effective Marketing with John Smiddy 11.04.2023

John Smiddy is the founder and a managing partner of LeadPlan Marketing, a firm dedicated to guiding clients toward business success by helping them reach a larger audience. As a marketing consultant, John has helped market and scale over 200 companies in various industries over the past decade. He is the author of  STOP Guessing, START Marketing and the creator of the 5 Pillars of Sales Conversio...

Episode 25 - Entrepreneurial Empowerment with Matt Lesser 28.03.2023

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.   Prior to launching Uniquely Normal, Matt owned and operated businesses, and served in several C-...

Episode 24 - Learning and Growing from Success and Failures with Stewart Townsend 14.03.2023

Stewart Townsend is the co-owner and Chief Revenue Officer of Podcast Hawk, a SaaS company created to automatically help people get booked as podcast guests. Stewart is also the founder of Channel as a Service, a consultancy firm that helps businesses accelerate B2B SaaS sales growth through every stage of the channel life-cycle. Before starting his career as an entrepreneur, Stewart worked in sev...

Episode 23 - 401k IRA Limits 28.02.2023

  A lot of changes have been made to retirement plans in 2022 and 2023. Specifically, changes in rules and regulations have been made in the contribution limits to IRA and 401k. With these new revisions, it's more important than ever for business owners to be educated and empowered to make informed decisions about their retirement savings—ensuring they're maximizing the benefits available to them....

Episode 22 - Why Businesses Fail 14.02.2023

Join Derek Dall'Olmo and Melissa Niedzielski on the latest episode of the Traversing Entrepreneurship podcast as they delve into the reasons why businesses fail and provide practical advice to avoid common pitfalls. Discover the importance of market research, self-management, and leadership, as well as the benefits of having a solid business plan in place. They also explore the notion that startin...

Episode 21 - Personal Insurance and Medicare FAQs with Geoffrey Harris & Traci George 03.01.2023

Geoffrey Harris is the Vice President of Medicare Sales at Michigan Planners, a full-service insurance agency specializing in employer group benefits. He graduated from Northern Michigan University with a degree in Business Administration and has been working in the insurance and financial services industry for over 40 years. Before joining Michigan Planners, Geoffrey worked as a financial represe...

Episode 20 - An Inside Look at the Restaurant Industry with Jeffrey Libman 06.12.2022

Jeffrey Libman is the General Manager of amical. Located in the heart of downtown Traverse City and overlooking the West Grand Traverse Bay, amical has been offering eclectic European cuisine since 1994. Jeffrey's love for the restaurant industry began when he was 14 working at a hotdog stand in Illinois. He later worked at Maggiano's, where he would manage the restaurant's Virginia and Washington...

Episode 19 - The Impact of a Strong Company Culture with Frederic Heller 22.11.2022

Frederic Heller is the President and owner of Northern Michigan Hospitality Management, a leading operator of destination, tourism, and transient properties. At the age of 25, Frederic became the General Manager of a hotel—he was an owner at 27. Under Frederic's leadership, Northern Michigan Hospitality Management has become a Marriott-approved company with several hotels under its management. Fre...

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