Traversing Entrepreneurship

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 [email protected] with questions and comments or to schedule a one-on-one conversation.

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 [email protected] with questions and comments or to schedule a one-on-one conversation.

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.

• 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

• 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 [email protected] 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.

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: [email protected] 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 [email protected] 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.

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: [email protected]

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 [email protected] 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.

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.

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: [email protected]

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 [email protected] 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.

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.

• 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: [email protected]

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 [email protected] 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.

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.

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: [email protected]

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 [email protected] 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.

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.

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: [email protected]

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 [email protected] 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.

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.

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: [email protected]

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 [email protected] 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.