Traversing Entrepreneurship

Derek Dall'Olmo
  • 5.0 (8)
  • ENTREPRENEURSHIP
  • UPDATED BIWEEKLY

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.

  1. FEB 19

    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 he faced, including burnout and layoffs. He emphasizes the importance of finding purpose, writing a book, and developing tools for personal growth. The conversation explores the transition from the comfort zone of corporate life to the discomfort zone of entrepreneurship, highlighting the need for discipline, consistency, and persistence in achieving success. In this conversation, Randy Martinez shares his journey of transformation, discussing the challenges he faced, the importance of persistence, and the role of mindset in personal growth. He emphasizes the need for a supportive community and the power of self-discovery in achieving one's purpose. The discussion highlights that transformation is not for everyone, but for those willing to put in the effort, the rewards can be profound.   Key Takeaways: • Randy experienced burnout during his corporate career. • He realized the need for personal transformation after being laid off. • Writing became a key focus for Randy after leaving corporate life. • Discipline, consistency, and persistence are essential for success. • The comfort zone can hinder personal growth and transformation. • Finding passion is crucial for converting it into purpose. • Randy developed tools to help track progress and accountability. • The journey of transformation is not linear and requires resilience. • Success is defined differently by each individual. The journey of transformation is ongoing and never truly ends. • Persistence is key in overcoming challenges and setbacks. • Building a supportive community is essential for personal growth. • Mindset plays a crucial role in navigating life's transitions. • Self-discovery is a vital part of finding one's purpose. • Vulnerability is a strength, not a weakness. • Your network can significantly impact your success. • Transformation requires discipline, consistency, and persistence.   —   Connect with Randy: LinkedIn: https://www.linkedin.com/in/randyrmartinez/ Website: https://randyrmartinez.com/about   —   Connect with Derek Dall'Olmo, CFP®, EA: Email: Derek@tremontefinancial.com LinkedIn: https://www.linkedin.com/in/derekdallolmo/ Website: https://tremontefinancial.com/about-us/   —   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, 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.    Derek is the founder of 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    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.

    56 min

  2. FEB 5

    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 leap into entrepreneurship with the support of his wife, why marketing in healthcare is non-negotiable, and how to use owned, earned, and paid media the right way. They dig into testimonials as earned media, using podcasting as a growth engine, and why you should never start with paid ads before you have a clear strategy. If you're a healthcare entrepreneur, marketer, or business owner looking to grow through authentic, strategic marketing, this conversation is packed with practical insight. In this episode, you'll learn: - How Saul went from corporate healthcare to starting Outcomes Rocket - Why having a strong support system matters when you launch a business - The difference between owned, earned, and paid marketing—and how they work together - How to turn testimonials into powerful earned media - Why podcasting is one of the best tools for building authority and trust - When procrastination is really a signal to delegate instead of push through - How to think about your unique selling proposition so your business stands out Snag the resources mentioned in this episode: https://docs.google.com/presentation/d/1RzYzExLWxMjb-YYQozxfk-vl7rwTIUo3/edit?usp=drivesdk&ouid=101891485019874324456&rtpof=true&sd=true If you enjoy this episode, hit subscribe, drop a comment with your biggest takeaway, and share it with another entrepreneur who's building something in healthcare or professional services. Connect with Saul: Email: saul@outcomesrocket.com Website: www.outcomesrocket.com Connect with Derek Dall'Olmo, CFP®, EA: Email: Derek@tremontefinancial.com LinkedIn: https://www.linkedin.com/in/derekdallolmo/ Website: https://tremontefinancial.com/about-us/ 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, 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.  Derek is the founder of 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.

    1h 3m

  3. JAN 15

    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 improve culture, build trust faster, and create more intentional teams. She also hosts the Have a Good Ripple Effect Podcast. The conversation covers leadership, culture, weather (your attitude), joy, resilience, parenting, entrepreneurship, and how to turn "crappy" into "happy" — even when life throws lightning bolts and literal house fires your way.     In this episode: People prepare for you—your mood becomes the team's weather. Culture shifts through small, repeatable actions, not huge overhauls. "Crappy to Happy" is a mindset + micro habit: pair difficult tasks with small joy. Joy must be intentional—if you wait for it, you'll wait forever. Experimentation is essential to entrepreneurship: "I'm doing hard things — what are YOU doing?" Tiny bursts of joy (15-minute meet-ups, quick rituals, micro breaks) can completely change team dynamics. Your impact is shaped by how you show up, not by circumstances. Thanks for tuning in — now take what you heard today and go make some noise, create your ripple, and keep building the life you actually want. See you next time.   Connect with Lisa: Book: Joy Is My Job by Lisa Even Website: LisaEven.com – speaking, workshops, resources Podcast: Have a Good Ripple Effect   Connect with Derek Dall'Olmo, CFP®, EA: Email: Derek@tremontefinancial.com LinkedIn: https://www.linkedin.com/in/derekdallolmo/ Website: https://tremontefinancial.com/about-us/   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, 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.  Derek is the founder of 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    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.

    53 min

  4. JAN 1

    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 the deep satisfaction that comes from helping people create more presence and more income at home. From learning to navigate entrepreneurship as a young professional to watching clients transform their families' lives, Molly's journey is full of meaning, humility, and impact. This is a conversation for anyone building a life that blends purpose, flexibility, and financial independence. Key Takeaways Although her program is predominantly women, Molly has had men join—and thrive. Hearing her clients' transformational stories continues to be one of the most rewarding aspects of her work. Creating space for clients to be truly present with their families while still generating income is at the heart of her mission. She never set out to become a coach—but the impact she's made has become undeniable. Freedom and flexibility matter: being able to take the family to Disney World, drive kids to school, or simply be present is transformational. The early lessons she learned as a young professional shaped the systems she now teaches. Income is not optional—helping families earn sustainably is foundational to her program. If Molly's story resonated with you—or if you're building a life where career and family actually work together—make sure to subscribe, leave a comment, and share this episode with someone who needs the encouragement. Your support helps us reach more people creating impact in their own lives and communities. #empowerment #women #career #family #coaching #transformation #income #impact #presence #stories — Connect with Molly: LinkedIn: https://www.linkedin.com/in/mollyrosespeed/ Website: https://www.mollyrosespeed.com/ Connect with Derek Dall'Olmo, CFP®, EA: Email: Derek@tremontefinancial.com LinkedIn: https://www.linkedin.com/in/derekdallolmo/ Website: https://tremontefinancial.com/about-us/ 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, 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.  Derek is the founder of 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.

    42 min

  5. 12/18/2025

    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 into predictable growth. Mark shares his evolution from the music industry to marketing technology expert, revealing how entrepreneurs can create structure, consistency, and freedom inside their businesses. You'll learn: 🎵 How Mark's creative roots led to a scalable marketing system 🧩 Why understanding customer needs is the foundation of every successful business ⚙️ How systems and processes set entrepreneurs free from daily firefighting 🎯 Why chasing more leads isn't the answer — focusing on the right leads is 🚪 How to think about exit planning from day one 💡 Why great ideas need great communication to actually sell Whether you're a startup founder or an experienced entrepreneur, this episode will challenge how you think about growth, marketing, and success. #Entrepreneurship #BusinessGrowth #MarketingStrategy #LeadGeneration #SalesSystems #BusinessSuccess #MarketingTechnology #BusinessProcesses #StartupAdvice #EntrepreneurMindset #SmallBusiness #CustomerExperience #BusinessFreedom #ScalableSystems #ExitPlanning Connect with Mark Osborne: LinkedIn: https://www.linkedin.com/in/remarkablemark/ Website: https://modernrevenuestrategies.com/ Connect with Derek Dall'Olmo, CFP®, EA: Email: Derek@tremontefinancial.com LinkedIn: https://www.linkedin.com/in/derekdallolmo/ Website: https://tremontefinancial.com/about-us/ 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, 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.  Derek is the founder of 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.

    46 min

  6. 09/25/2025

    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 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 understanding financials and learning to say no to distractions. Takeaways: Chris started his entrepreneurial journey at a young age. Financial literacy is crucial for business success. Building a strong team requires learning from painful lessons. Identifying A, B, and C players is key in hiring. Empowering employees to solve problems fosters ownership. Data-driven decision-making is essential in digital marketing. Managing cash flow is critical in seasonal businesses. Leveraging debt can be a powerful tool for growth. Saying no to distractions is vital for focus. Understanding your financials is non-negotiable for success. 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, 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.  Derek is the founder of 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  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.

    55 min

  7. 09/11/2025

    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 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 Eric balances business with family life.  Insights into creating cash-flowing assets and financial freedom. Eric Stopper is an e-commerce entrepreneur and investor. Connect with him on LinkedIn or visit his websites: profitable.com, legendaryitems.com, and zealothealth.com. If you enjoyed this episode, please leave a review on Apple Podcasts and share it with your business-minded friends. For more insights, visit tramontetax.com to schedule a chat with Derek. #Entrepreneurship #Ecommerce #BusinessSuccess #FinancialFreedom 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, 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.  Derek is the founder of 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  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.

    58 min

  8. 08/28/2025

    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, 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 strategies and financial planning  The impact of social media on business development Beau's philosophy on lifelong learning and personal growth Guest Information: Beau Eckstein: Business Ownership Coach and Emerge Lending Group Website: BeauEckstein.com Book a Call: BookWithBeau.com If you enjoyed this episode, please leave us a review on Apple Podcasts and share it with your business-minded friends. Stay tuned for more inspiring stories and insights on the Traversing Entrepreneurship podcast. #Entrepreneurship #BusinessGrowth #SBAloans #FranchiseConsulting 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, 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.  Derek is the founder of 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.

    1h 3m
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5
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About

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.

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