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  • Navigating the Emotional Rollercoaster of Entrepreneurship with Brian Smith

    Navigating the Emotional Rollercoaster of Entrepreneurship with Brian Smith
    2025/06/12
    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 時間 13 分
  • Navigating the Private Credit Landscape: Mike Shum's Journey

    Navigating the Private Credit Landscape: Mike Shum's Journey
    2025/05/22

    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 分
  • From Forest Service to Global Visa with Rob Lee

    From Forest Service to Global Visa with Rob Lee
    2025/05/08

    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 分
  • Building an Uncopyable Brand: Marketing Strategies with Steve Miller

    Building an Uncopyable Brand: Marketing Strategies with Steve Miller
    2025/02/27

    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 時間 6 分
  • Zero to One: The Art of Product Development with Nick McEvily

    Zero to One: The Art of Product Development with Nick McEvily
    2025/02/13

    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 分
  • The Future of Entrepreneurship in a Tech-Driven World with Adam Fineberg

    The Future of Entrepreneurship in a Tech-Driven World with Adam Fineberg
    2025/01/30

    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 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

    If you enjoy the show, please leave a review on iTunes to help others discover the podcast.
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    1 時間 1 分
  • The Power of Networking in Real Estate Investing with Matt Theriault

    The Power of Networking in Real Estate Investing with Matt Theriault
    2025/01/16
    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: EpicRealEstate.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. 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 | Follow Melissa 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 時間 5 分
  • Staying Ahead of the Curve: The Future of Marketing for Advisors featuring Jake Wagner

    Staying Ahead of the Curve: The Future of Marketing for Advisors featuring Jake Wagner
    2024/12/12
    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: https://www.linkedin.com/in/jacobbwagner/ Email: jake@4fp.co 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 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 | Follow Melissa 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 時間 26 分