『Traversing Entrepreneurship』のカバーアート

Traversing Entrepreneurship

Traversing Entrepreneurship

著者： Derek Dall'Olmo
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 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. マネジメント・リーダーシップ リーダーシップ 経済学
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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.
    続きを読む 一部表示
    59 分

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