Episodes

  • Helping Your Team Dream Bigger with Kate Volman

    Helping Your Team Dream Bigger with Kate Volman
    Jul 24 2025

    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: https://www.linkedin.com/in/katevolman
    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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    47 mins
  • Building a Business That Works for You with Sarah Noel Block

    Building a Business That Works for You with Sarah Noel Block
    Jul 10 2025

    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: sarahnoelblock.com

    • Join the Club: Tiny Marketing 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 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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    52 mins
  • Navigating the Entrepreneurial Journey with Corey Morris

    Navigating the Entrepreneurial Journey with Corey Morris
    Jun 26 2025

    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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    50 mins
  • Navigating the Emotional Rollercoaster of Entrepreneurship with Brian Smith

    Navigating the Emotional Rollercoaster of Entrepreneurship with Brian Smith
    Jun 12 2025
    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: http://strategyladders.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. 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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    1 hr and 13 mins
  • Navigating the Private Credit Landscape: Mike Shum's Journey

    Navigating the Private Credit Landscape: Mike Shum's Journey
    May 22 2025

    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 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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    50 mins
  • From Forest Service to Global Visa with Rob Lee

    From Forest Service to Global Visa with Rob Lee
    May 8 2025

    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: http://www.swiftpassportservices.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.

    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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    59 mins
  • Building an Uncopyable Brand: Marketing Strategies with Steve Miller

    Building an Uncopyable Brand: Marketing Strategies with Steve Miller
    Feb 27 2025

    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 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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    1 hr and 6 mins
  • Zero to One: The Art of Product Development with Nick McEvily

    Zero to One: The Art of Product Development with Nick McEvily
    Feb 13 2025

    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: https://nickmcevily.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.

    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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    51 mins