Traversing Entrepreneurship
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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Scaling Your Business and Mastering Social Media Strategy with Katie Brinkley
03/05/2026
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 team of eight, and the strategies that have helped her thrive in a competitive, male-dominated industry. Brinkley shares lessons on team building, company culture, leveraging social media for business growth, and defining success on her own terms. Key Moments: • Katie Brinkley’s Career Journey: From Denver to Sports Media • Transition from Radio to TV Marketing and the Birth of NextStep Social • Scaling from Solopreneur to Agency Owner • Standing Out in Male-Dominated Industries • Defining Success Through Freedom and Flexibility • Building a Strong Team and Company Culture • Evolution of Social Media: From MySpace to Modern Platforms • NextStep Social’s Marketing Strategy and VIP Days • Sales Pipeline: Speaking, Networking, and Podcasting • Balancing Business Ownership with Personal Life • Advice for Entrepreneurs on Social Media Strategy This episode provides actionable insights for business owners on scaling a business, managing a team, and creating a marketing strategy that drives real growth. Like, subscribe, and comment to join the conversation! Connect with Katie Brinkley: LinkedIn: Website: 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Burnout to Breakthrough: Randy Martinez’s Journey
02/19/2026
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: Website: — 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Understanding Earned Media and Its Impact with Saul Marquez
02/05/2026
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: 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: Connect with Derek Dall'Olmo, CFP®, EA: Email: 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.
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Change Your Weather: Leadership, Joy, and the Ripple Effect with Lisa Even
01/15/2026
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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Balancing Family, Income & Impact: Molly Rose Speed’s Journey of Empowerment
01/01/2026
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.
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Why Most Entrepreneurs Fail (and How to Avoid It) with Mark Osborne
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.
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The Journey of Digital Marketing Expert Chris Shihadeh
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.
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Motivation and Entrepreneurship... What an Epic Journey with Eric Stopper
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.
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Navigating Entrepreneurship with Beau Eckstein
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.
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Navigating Entrepreneurship with Kasim Aslam
08/14/2025
Navigating Entrepreneurship with Kasim Aslam
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 resilience and growth from Kasim's career. Kasim Aslam is the founder of Solutions 8 and Pareto Talent. He is an award-winning hiring expert and bestselling author. Learn more about his work at KASIM.me. If you enjoyed this episode, please leave us a review on Apple Podcasts and share it with your entrepreneurial friends. For more insights, visit tramontetax.com to schedule a chat with Derek. #Entrepreneurship #BusinessGrowth #AI #TalentAcquisition 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.
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Helping Your Team Dream Bigger with Kate Volman
07/24/2025
Helping Your Team Dream Bigger with Kate Volman
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 about how you show up—for your business and your people. In This Episode: Why “dream management” might be the leadership superpower no one’s talking about How Kate’s experience at the Chamber shaped the way she builds relationships What the “iceberg” analogy reveals about business challenges Why most disengaged employees are really just unfulfilled people How asking one simple question can change your team culture The truth about partnerships—and what to know before diving in Why good leaders care about more than just productivity How to focus on strengths and still grow your business the right way Connect with Kate: Connect with Kate: Learn more about Floyd Consulting: floydconsulting.com 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.
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Building a Business That Works for You with Sarah Noel Block
07/10/2025
Building a Business That Works for You with Sarah Noel Block
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 Sarah’s “biz dev blitz” to fill your pipeline fast, how to reverse-engineer your revenue goals, and why micro-yeses in your sales process can seriously boost conversions. 💡 What You’ll Learn Why Sarah walked away from corporate marketing (and never looked back) How the Tiny Marketing Club helps consultants design lifestyle-first businesses What a “Biz Dev Blitz” is—and how you can run one to land more clients The real reason most businesses struggle with offer creation Why sales should feel collaborative, not manipulative How to build trust through micro-commitments What Sarah means when she says your offer should be like a staircase The importance of simplifying your message to match how clients actually think Why good marketing starts with understanding real pain points—not just catchy copy How to test and tweak your offers without burning time or budget Connect with Sarah: Learn more about Sarah: Join the Club: 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Navigating the Entrepreneurial Journey with Corey Morris
06/26/2025
Navigating the Entrepreneurial Journey with Corey Morris
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 importance of niching down to enhance service quality and client relationships. He shares insights on defining success, the challenges of decision-making, and the significance of recognizing when a client is not the right fit. Additionally, he introduces his book, 'The Digital Marketing Success Plan,' which outlines a structured approach to digital marketing strategy. Key Moments: Corey's journey into digital marketing began with a passion for SEO. The landscape of SEO has evolved significantly over the years. Transparency in financials is crucial when transitioning to business ownership. Negotiation requires setting aside personal feelings for business success. Leadership involves adapting strategies to meet client needs. Recognizing when we are not the right fit is crucial. Learning how to say no is one of the most important lessons. Making decisions is key to moving forward. The Digital Marketing Success Plan provides a structured approach to marketing. Connect with Corey: Email: corey@voltage.digital Website: https://thedmsp.com 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. If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Navigating the Emotional Rollercoaster of Entrepreneurship with Brian Smith
06/12/2025
Navigating the Emotional Rollercoaster of Entrepreneurship with Brian Smith
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. Brian opens up about the emotional challenges of building a business and how critical decision-making is to long-term success. He dives into the culture shocks of moving to Mexico, the realities of starting a new agency during COVID-19, and how identifying market gaps can lead to unexpected opportunities. Throughout the episode, Brian shares insights on building a resilient mindset, fostering a strong company culture, and why consistency is non-negotiable in the pursuit of business growth. If you’re an entrepreneur looking to learn from someone who’s been in the trenches, this episode is packed with practical wisdom and relatable stories. In This Episode: Entrepreneurial Journey: Brian's early ventures included washing boats, starting a photography business, and later transitioning into real estate, leading to significant growth and community involvement. Overcoming Burnout: Burnout led Brian to reassess his life and ultimately pivot into coaching and supporting other entrepreneurs. Resilience and Decision-Making: Entrepreneurship requires emotional resilience, decisive action, and the ability to adapt to changing circumstances. Team Building and Scaling: Successful business growth involves building a strong team, leveraging expertise, and fostering a positive company culture. Adapting to Change: COVID-19 prompted Brian to start a new agency, highlighting the importance of adaptability and seizing new opportunities. Mindset and Sales Discipline: Maintaining a resilient mindset and treating sales as a daily non-negotiable are crucial for sustained success. Connect with Brian: Email: brian@strategyladders.com Website: 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Navigating the Private Credit Landscape: Mike Shum's Journey
05/22/2025
Navigating the Private Credit Landscape: Mike Shum's Journey
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. Key Moments: 00:00 Introduction to Entrepreneurship and Cascade Debt 01:04 Mike Shum's Journey: From Banking to Entrepreneurship 03:01 The Birth of Cascade Debt and Its Mission 06:39 Understanding Private Credit and Asset-Based Lending 10:30 Innovations in Alternative Credit Scoring 12:56 Streamlining Asset-Based Lending Processes 17:24 Differences Between Private Credit and Equity 23:11 The Impact of COVID-19 on Lending Practices 26:01 Current Trends in Private Credit Returns 27:51 Accessibility in Capital Markets 30:12 Scaling Without Compromise 32:42 Navigating Uncertainty in Business 35:04 Headwinds in Private Credit 39:32 The Evolution of Private Credit 43:10 The Future of Private Credit 46:39 Advice for Aspiring Entrepreneurs Connect with Mike: Email: mike@cascadedebt.com Website: www.cascadedebt.com 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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From Forest Service to Global Visa with Rob Lee
05/08/2025
From Forest Service to Global Visa with Rob Lee
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 importance of adapting to change and leveraging technology to improve efficiency. Key Moments: Embrace change and be comfortable with the unknown The importance of delegating tasks and hiring experts Balancing work and personal life as business partners Adapting to evolving international travel regulations Connect with Rob: Email: rob@swiftpassport.com Website: 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Building an Uncopyable Brand: Marketing Strategies with Steve Miller
02/27/2025
Building an Uncopyable Brand: Marketing Strategies with Steve Miller
In this episode of Traversing Entrepreneurship, Derek Dall’Olmo sits down with Steve Miller, best-selling author and marketing consultant, to discuss the power of differentiation in business. Steve shares his journey from aspiring PGA Tour player to renowned marketing expert and explains why creating an uncopyable brand is essential for long-term success. He highlights the importance of personal branding, the credibility boost of writing a book, and why businesses should focus on understanding their target market—what he calls the "moose." Steve also explores innovation through observation, the dangers of competing on price, and why offline marketing strategies still hold immense value. If you're looking for practical strategies to stand out in a crowded marketplace, this episode is packed with actionable insights. Key Moments: 00:00 Introduction to Entrepreneurship and Unique Stories 02:53 Steve Miller's Journey: From Golf to Marketing 07:36 The Importance of Writing a Book for Credibility 10:46 Creating an Uncopyable Brand 11:35 Understanding Your Unique Value Proposition 22:50 Maintaining Uncopyableness in a Copycat World 34:32 Understanding the Box: The Manufacturing Mindset 38:00 Building Your Own Box: The Key to Un-copyability 42:14 The Power of Observation: Learning from Other Industries 47:59 Marketing on a Budget: The Importance of Offline Strategies 51:10 Common Mistakes: What to Avoid in Business 54:31 Authenticity in Branding: Standing Out in a Crowded Market 56:42 The Journey of Personal Branding: Lessons from Experience Connect with Steve: Email: steve@beuncopyable.com Website: https://beuncopyable.com 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Zero to One: The Art of Product Development with Nick McEvily
02/13/2025
Zero to One: The Art of Product Development with Nick McEvily
In this episode of Traversing Entrepreneurship, Derek Dall’Olmo interviews Nick McEvily, head of product at XGen Ai. They dive into Nick’s journey from design to product leadership, his experiences with startup successes and failures, and the importance of testing assumptions in product development. Nick discusses how AI is transforming the retail landscape, the significance of user experience in software design, and why fractional product leadership can be a game-changer for early-stage companies. This episode offers valuable insights on decision-making, problem-solving, and the mindset required to navigate the entrepreneurial landscape successfully. Key Moments: 00:00 Introduction to Entrepreneurship and AI 01:24 Nick's Journey: From Design to Product Leadership 05:27 The Zero to One Concept in Product Development 09:23 Testing Assumptions: The Key to Validating Ideas 13:02 Learning from Failure: Insights from Past Ventures 16:04 XGen Ai: Merging AI with Retail Experience 21:24 Defining Success in AI-Driven Retail 25:21 Choosing the Right Path in Design 27:11 The Reality of Entrepreneurial Sacrifice 28:29 Defining Personal Success 29:41 Understanding Fractional Product Leadership 31:08 Common Mistakes in Software Development 33:34 The Importance of Focus in Entrepreneurship 34:22 Future Trajectories in Entrepreneurship 36:07 The Rise of Venture Studios 38:39 Transitioning from Time to Cash Flow 40:23 Advice for Aspiring Entrepreneurs 42:18 Exploring Problems Over Solutions 46:25 The Value of Process in Decision Making 47:25 Curiosity and Ego in Entrepreneurship Connect with Nick: Email: nickmcevily@gmail.com Website: 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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The Future of Entrepreneurship in a Tech-Driven World with Adam Fineberg
01/30/2025
The Future of Entrepreneurship in a Tech-Driven World with Adam Fineberg
In this episode of the Traversing Entrepreneurship podcast, Derek Dall'Olmo interviews Matt Theriault, the CEO and founder of Epic Real Estate. Matt shares his journey from the music industry to real estate, highlighting the challenges he faced and the valuable lessons he learned. He discusses creative financing strategies, the importance of finding profitable deals, and how to build wealth through real estate investment. Matt also explains the transition to turnkey real estate investments and how these can simplify the process for investors. Throughout the episode, Matt and Derek cover key aspects of entrepreneurship and real estate, including the significance of legacy, the shift from employee to business owner, and how to set expectations with investors. They also touch on the strategies for making real estate a reliable source of passive income and preserving wealth in the long term. Matt offers practical advice for new investors, emphasizing the importance of understanding market trends and learning from mistakes. Key Moments: 00:00 Introduction to Entrepreneurship and Talent Acquisition 01:00 Adam Feinberg's Journey to My Personal Recruiter 02:51 Navigating Technology in Recruitment 05:58 Building a Scalable Software Solution 08:59 Success Metrics and Client Success Rates 11:59 Understanding Client Demographics and Industries 14:55 Defining Success in Entrepreneurship 18:08 Overcoming Challenges and Growing Pains 21:00 Competitors and Corporate Espionage 23:50 The Importance of Online Presence and SEO 30:03 Future of SEO in the Age of AI 35:35 Building a Strong Online Presence 44:13 Navigating the Future of Entrepreneurship 58:32 Empowering the Next Generation of Entrepreneurs Connect with Adam: Email: adam@mypersonalrecruiter.com Website: www.mypersonalrecruiter.com 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on Subscribe: | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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The Power of Networking in Real Estate Investing with Matt Theriault
01/16/2025
The Power of Networking in Real Estate Investing with Matt Theriault
In this episode of the Traversing Entrepreneurship podcast, Derek Dall'Olmo interviews Matt Theriault, the CEO and founder of Epic Real Estate. Matt shares his journey from the music industry to real estate, highlighting the challenges he faced and the valuable lessons he learned. He discusses creative financing strategies, the importance of finding profitable deals, and how to build wealth through real estate investment. Matt also explains the transition to turnkey real estate investments and how these can simplify the process for investors. Throughout the episode, Matt and Derek cover key aspects of entrepreneurship and real estate, including the significance of legacy, the shift from employee to business owner, and how to set expectations with investors. They also touch on the strategies for making real estate a reliable source of passive income and preserving wealth in the long term. Matt offers practical advice for new investors, emphasizing the importance of understanding market trends and learning from mistakes. Key Takeaways: Real estate is a proven path for creating wealth. Creative financing can open doors to property acquisition without initial capital. Networking and building a strong reputation are key to attracting opportunities. Turnkey investments are a powerful way to simplify real estate investing. Wealth preservation strategies are essential for long-term financial success. The BRRRR strategy is an effective tool for growing wealth. Passive income through real estate requires thoughtful management and planning. Setting clear expectations with investors ensures smooth transactions. Real estate is fundamentally a people-driven business that thrives on relationships. This episode provides valuable insights into how real estate investment can lead to financial freedom and long-term wealth creation. Matt’s experience and strategies are a great resource for anyone looking to succeed in the real estate market. Chapters: 00:00 - Introduction to Entrepreneurship and Real Estate 01:07 - Matt Theriault's Journey from Music to Real Estate 08:06 - The Turning Point: Discovering Real Estate as Wealth Creation 10:48 - Creative Financing: Acquiring Properties Without Capital 12:04 - The First Deal: Learning by Doing 20:34 - The Second Deal: Building Reputation and Partnerships 27:55 - Transitioning to Turnkey Real Estate Investments 30:03 - Wealth Preservation Strategies in Real Estate 31:41 - The Importance of Legacy in Real Estate Investment 34:06 - Breaking the Cycle: From Employee to Entrepreneur 38:36 - Learning from Mistakes: The Value of Experience 39:32 - Regrets and Lessons: The Bigger Deals 44:43 - Setting Expectations with Investors 47:37 - Making Real Estate Passive Income 52:39 - Advice for Novice Real Estate Investors Connect with Matt: Email: matt@epicrealestate.com Website: 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. 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on | Follow Melissa on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Staying Ahead of the Curve: The Future of Marketing for Advisors featuring Jake Wagner
12/12/2024
Staying Ahead of the Curve: The Future of Marketing for Advisors featuring Jake Wagner
In this episode of Traversing Entrepreneurship, we are extremely excited to be joined by Jake Wagner, CDMP as he shares proven strategies and insights to help financial professionals attract their ideal clients, deliver exceptional service, and grow a sustainable business. Whether you're a seasoned advisor or just starting out, you'll find actionable tips and real-world examples to take your practice to the next level. Tune in and start optimizing your marketing, operations, and client experience today. This week on Traversing Entrepreneurship: 0:01:55 Jake discusses what motivated him to start his own agency instead of continuing to work for other startups. 0:05:00 Jake explains his transition from technical advising to a full-stack marketing agency approach. 0:09:10 Jake and Derek discuss the importance of aligning marketing efforts with the advisor's unique personality and brand. 0:13:15 Jake shares how his upbringing in the financial planning profession influenced his focus on supporting that industry. 0:20:00 Jake emphasizes the importance of the "doctor frame" when working with clients, versus a "salesman" approach. 0:25:00 Jake outlines his three-part consulting process for helping financial professionals with their marketing. 0:32:44 Jake discusses the challenges of working in an oversaturated market and the importance of finding the right advisor-client fit. 0:40:45 Jake provides advice for aspiring entrepreneurs on focusing first on their offer and ideal client. 1:18:22 Jake shares how to get in touch with him and his key recommendations for financial professionals, including having a marketing plan, meaningful metrics, and the right tools and advisors. Connect with Jake: LinkedIn: Email: Website: www.4fp.co 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 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on | Follow Melissa on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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From Engineer to Empowering Coach: Sairan Aqrawi's Remarkable Reinvention
11/14/2024
From Engineer to Empowering Coach: Sairan Aqrawi's Remarkable Reinvention
In this episode, we are joined by Sairan Aqrawi as she shares her remarkable journey from Kurdish immigrant to successful business coach and mentor. After initially struggling to adapt to life in the US, Sairan discovered her true calling in coaching and personal development, transitioning from a decades-long engineering career. She emphasizes the importance of clarity, focus, and grit when pursuing entrepreneurial goals, drawing parallels between parenting and leading teams. Sairan's story underscores the value of progress over perfection, and how setbacks can ultimately shape one's path to success. Whether you're a young professional or an experienced entrepreneur, Sairan's advice on identifying your "hidden gems" and not being afraid to pivot will inspire you to reach new heights. Connect with Sairan on LinkedIn or Instagram for a free coaching consultation. This week on Traversing Entrepreneurship: [0:00 - 2:00] Introduction to Sairan Akrawi and her background as a Kurdish immigrant to the US [2:00 - 6:00] Sairan's initial struggles and challenges adapting to life in America, and the importance of having the right mindset [6:00 - 11:00] Sairan's transition from engineering to coaching and mentoring, discovering her "hidden gem" talents [11:00 - 16:00] The pivotal moment when Sairan decided to pursue coaching over continuing her PhD program [16:00 - 21:00] Sairan's perspective on progress over perfection, and the value of diverse experiences [21:00 - 26:00] Advice for young professionals and entrepreneurs: clarity, focus, and grit [26:00 - 31:00] The importance of self-belief, competence, and not being your own worst critic [31:00 - 36:00] Sairan's tips on handling disappointments and setbacks as an entrepreneur [36:00 - 41:00] Parallels between parenting and leading teams, the power of leading by example [41:00 - 47:00] Sairan's offer of free coaching consultations, and Derek's introduction of his own business Connect with Sairan: LinkedIn: Email: sairan28@gmail.com 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 is the owner of 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on | Follow Melissa on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Traversing the Private Equity Landscape: Opportunities and Challenges with Brad Zapp
10/10/2024
Traversing the Private Equity Landscape: Opportunities and Challenges with Brad Zapp
Ever wonder what it takes to build a successful business from scratch? Join us as we sit down with serial entrepreneur Brad Zapp to get the inside scoop on his journey from wealth management to founding a cutting-edge digital VC firm. You won't want to miss this eye-opening conversation! Brad Zapp is a CFP, was a former founder of an independent Wealth Advisory Firm, sold that, and founded a Digital Venture Capital firm that uses AI to vet opportunities. he is now bringing his private Strategy to the public by registering with the SEC and will be distributing his fund thru the independent Advisor channel he started his career in. This week on Traversing Entrepreneurship: 0:00:35 - Introducing Brad Zapp 0:02:08 - Brad Zapp discusses transition from wealth management to founding digital venture capital firm 0:05:00 - Differences between private equity and venture capital 0:10:00 - Role of venture capitalists in financing innovative, technology-driven companies 0:13:04 - Evolving entrepreneurship landscape and successful outcomes beyond IPOs 0:14:13 - Success in venture capital, shares examples of successful investments 0:19:24 - Importance of founder psychology, how firm uses it in due diligence 0:26:33 - Firm's digital approach to venture capital, especially during COVID-19 0:32:34 - Using AI and machine learning to enhance investment process 0:39:26 - Story behind "Wendell" name for firm's AI assistant 0:42:02 - Brad discusses biggest challenges in creating, growing VC firm in Midwest Connect with Brad: Website: LinkedIn: Email: bzapp@conneticventures.com 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 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on | Follow Melissa on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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An Entrepreneur's Tale of Triumph and Transformation with Christophe Dessaigne
09/28/2024
An Entrepreneur's Tale of Triumph and Transformation with Christophe Dessaigne
Christophe Dessaigne joins us to share his entrepreneurial journey, from starting a tech company helping blind people to co-founding the online grocery store Jack B. He talks about the challenges of the online grocery industry and how Jack B is tackling them. Christophe also opens up about his personal growth, dealing with childhood wounds, and advice for aspiring entrepreneurs. You do not want to miss this episode! Christophe Dessaigne is a co-founder of JackBe, a disruptive, online-only grocery store model based out of Oklahoma City that aims to serve people and build His Kingdom. Prior to that, Christophe spent seven years working for a faith-based private equity firm based in Indiana. Christophe’s previous business experiences spanned several sectors, from technology to media to retail, both in Europe and the US. For each of his previous posts, Christophe was responsible for providing strategic oversight and leadership. Christophe has been married to his wife, Melissa, for 16 years, and together, they have three children—ages fourteen, twelve, and eleven—to keep them busy. In 2022, Christophe and his family relocated to France for a short season but continued to work in the US. Christophe enjoys cooking and hosting family and friends (old and new), traveling, trail running, mountain climbing/hiking, and any outdoor activities. This week on Traversing Entrepreneurship: 0:00:38 - Introducing Christophe Dessaigne 0:01:45 - Speaker's background and early entrepreneurial journey, including a technology company. 0:03:31 - Transition to co-founding Jack B. 0:07:28 - Explanation of Jack B's unique online grocery model, focusing on curbside pickup. 0:09:47 - Comparison of Jack B's model to delivery-focused online grocery services. 0:12:30 - Approach to creating efficiencies in the online grocery industry. 0:15:19 - Top successes and failures with Jack B. 0:19:49 - Pivot towards partnering with big box stores as a solution provider. 0:24:23 - Explanation of Jack B's financial model and potential for market growth. 0:30:16 - Personal journey of addressing childhood wounds and seeking emotional healing. 0:35:59 - Advice for aspiring entrepreneurs and high potential leaders. 0:46:02 - Opportunities for consulting, investment, and connecting. Connect with Christophe: LinkedIn: Email: dessaigne@outlook.com 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 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on | Follow Melissa on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Fearless Finances: Empowering Women to Achieve More with Jenna Biancavilla
09/10/2024
Fearless Finances: Empowering Women to Achieve More with Jenna Biancavilla
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 importance of hiring early, delegating tasks, and maintaining a flexible work environment. Jenna advised aspiring entrepreneurs to find their passion, understand their limitations, and have a clear end game. She also stresses the importance of transparency in financial advice and the need for a succession plan. This week on Traversing Entrepreneurship: Jenna Biancavilla's entrepreneurial journey, from pre-med to finance advisor Challenges Jenna faced working in the finance industry at large firms Jenna's decision to start her own firm, Pearl Capital, to better serve clients Additional business ventures, including Savvy and an online course Challenges of managing multiple businesses and the benefits of a holding company Lessons Jenna learned, including mistakes with hiring and firing employees Advice for aspiring entrepreneurs, including finding passion and defining an end game Importance of transparency and trust when working with financial clients Jenna's contact information and encouragement for listeners to reach out Connect with Jenna: Website: thepearlcapital.com LinkedIn: https://www.linkedin.com/in/jennabiancavilla/ Email: admin@thepearlcapital.com 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 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on | Follow Melissa on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Stealth Consulting: Guiding Entrepreneurs Through the Chaos with Wesley J. Mathews
08/22/2024
Stealth Consulting: Guiding Entrepreneurs Through the Chaos with Wesley J. Mathews
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 own business. This week on Traversing Entrepreneurship: 0:00:06 meet Wes Mathews 0:01:16 Discussing the start of Wes' entrepreneurial journey. 0:02:45 Transitioning out of the day-to-day operations. 0:05:13 Explaining the trust issues with marketing companies. 0:07:34 Achieving rapid growth with Stealth Consulting. 0:12:52 Comparing entrepreneurship to a boxer's mentality. 0:19:17 Avoiding delusion as a visionary entrepreneur. 0:24:47 Reflecting on the timing of business decisions. 0:33:51 Asking what you really, really want. Connect with Wes: Website: stealthconsulting.com LinkedIn: https://www.linkedin.com/in/wesleymathews/ Email: Wes@stealthconsulting.com 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, 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. Please email Derek Dall’Olmo at with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on | Follow Melissa on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Overcoming Adversity Through Mindfulness and Entrepreneurship with Dr. Allen Lomax
06/25/2024
Overcoming Adversity Through Mindfulness and Entrepreneurship with Dr. Allen Lomax
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 growing cities and the rising costs of rent for college students. Through their stories and insights, they emphasize the power of empathy and mindfulness in achieving success and making impactful investments. This week on Traversing Entrepreneurship: [0:00] Introduction - Derek Dall'Olmo welcomes listeners and introduces Dr. Allen Lomax [5:30] Allen shares his personal story of struggles with identity and depression as a young person [10:20] Allen discusses finding fulfillment later in life through therapy, education, and helping others [15:00] Allen talks about his passion for horses and discovering empathy and mutuality in relationships [20:12] Allen explains his evolution from single-family real estate to commercial properties and capital raising for existing syndicates [25:36] Allen discusses how he builds connections through his podcast and relies on it to find potential partners [31:30] Allen talks about using mastermind groups for support and validation in real estate deals [34:46] Derek and Allen discuss lessons around leverage from Allen's past experiences [43:21] Allen bAllences his academic career with real estate investing by leveraging flexibility as a professor [46:03] Derek and Allen discuss affordable housing challenges for local workers in vacation towns [52:08] Derek expresses concerns about rising costs of college housing and its impact on students [55:00] Allen offers a free strategic consultation and wraps up the discussion Connect with Allen: Website: LinkedIn: Email: steedtalker@gmail.com 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 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on | Follow Melissa on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Episode 40 - Automating Your Business to Create Growth and Personal Freedom with Matt Clark
06/11/2024
Episode 40 - Automating Your Business to Create Growth and Personal Freedom with Matt Clark
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 generation on LinkedIn, and prioritizing freedom and lifestyle in their businesses. Additionally, they discussed the importance of accountability in business, particularly in the context of marketing efforts, and emphasized the need for agencies and clients to work together to ensure timely responses, progress tracking, and responsible decision-making. This week on Traversing Entrepreneurship: Matt Clark, CEO of Virtual Edge, shares insights on B2B marketing with AI and automation. Automating sales processes using LinkedIn. Identifying ideal clients for B2B service providers. Using AI to enhance networking and sales on LinkedIn. Building systems for business success, personal freedom, and client success. Taking responsibility in business and creating a successful marketing strategy. Entrepreneurship, business growth, and tax strategy. Connect with Matt: Website: thevirtualedge.com LinkedIn: Email: matt@thevirtualedge.com 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 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on | Follow Melissa on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Episode 39 - Entrepreneurship, Learning Challenges, and Environmental Stewardship with Gerald Rosengarten
05/28/2024
Episode 39 - Entrepreneurship, Learning Challenges, and Environmental Stewardship with Gerald Rosengarten
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 and new product launches. "I went to a men's manufacturer and I was showing the jacket with a woman named Clara Hancock who was the premier writer for menswear daily, which was the main paper, she looked at the jacket and said let’s call it leisure suit and that's how it was done.” - Gerald Rosengarten This week on Traversing Entrepreneurship: 0:25 - Exploring Entrepreneurship, Addressing Learning Disabilities, and Promoting Environmental Stewardship. 7:34 - Innovative Real Estate Development in New York City: A Focus on Unique Properties and Design. 16:25 - Insights into New York City Real Estate: Challenges and Key Lessons. 23:50 - Authoring a Book Amidst the Pandemic: Conquering Dyslexia and Emphasizing Resilience. 28:32 - Enhancing Accessibility: A Personal Journey Overcoming Dyslexia. 36:01 - Tackling Dyslexia: Utilizing Reading Overlays for Better Comprehension. 42:02 - Navigating Real Estate Development: Exploring Connections with Russia. 48:56 - Driving Success in Entrepreneurship: Book Promotion and Innovative Product Development. 55:42 - Strategies in Entrepreneurship: Tax Planning and Pioneering New Products. Connect with Gerald: Website: Get his book: amazon.com/Jump-Train-Dyslexic-Entrepreneurs-50-Year/dp/1637556160/ 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 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on | Follow Melissa on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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Episode 38 - Saying No to Make Room for Yes: Prioritizing Values Over Profits in Business with Josh Traeger
05/14/2024
Episode 38 - Saying No to Make Room for Yes: Prioritizing Values Over Profits in Business with Josh Traeger
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 rewards of prosecuting child sexual assault cases. Additionally, they touch on the growing trend of individuals in small towns pursuing entrepreneurial careers, and share their insights on ethical dilemmas in business and the legal profession. “If I'm working with small business, not only do I want to get that small business in the right direction, from an entity formation perspective, from a trademark perspective, from a managerial perspective, but the reason I want to do that, and the conversations I have with that client are around how they can build successfully for the future, so that they can contribute back to the community in which we exist.” - Josh Traeger This week on Traversing Entrepreneurship: 0:00 Military legal career, from prosecutor to founding a law firm. 7:48 Military trials and the challenges of prosecuting child sexual assault cases. 13:57 Military members' criminal behavior and the legal firm representing them. 21:51 Entrepreneurial spirit in Traverse City, Michigan, with a focus on legal services. 25:47 Legal practice vision and values, with a focus on community building and rehabilitation. 31:16 The importance of personal connections and unique value in a business. 35:16 Launching a legal business in Traverse City, Michigan, with challenges related to cost, access to capital, and overestimating experience. 40:55 Lawyer's struggles with branding, marketing, and learning curve in a new practice area. 47:14 Prioritizing values and saying no to opportunities that don't align with them. 53:12 Seeking help and support in entrepreneurship. 58:11 The importance of collaboration and seeking outside validation in entrepreneurship. 1:02:43 Loneliness and community building in northern Michigan. Connect with Josh: Website: LinkedIn: Email: josh@truenorthlegalgroup.com 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 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 with questions and comments or to schedule a one-on-one conversation. TreMonte Page | Follow Derek on | Follow Melissa on Subscribe: | | | | | | If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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