What does it really take to build a business that scales and sells itself?

In this episode of Traversing Entrepreneurship, Derek Dall'Olmo sits down with Mark Osborne, founder of Modern Revenue Strategies, to explore how systems, strategy, and clarity can turn chaos into predictable growth.

Mark shares his evolution from the music industry to marketing technology expert, revealing how entrepreneurs can create structure, consistency, and freedom inside their businesses.

You'll learn:

🎵 How Mark's creative roots led to a scalable marketing system
🧩 Why understanding customer needs is the foundation of every successful business
⚙️ How systems and processes set entrepreneurs free from daily firefighting
🎯 Why chasing more leads isn't the answer — focusing on the right leads is
🚪 How to think about exit planning from day one
💡 Why great ideas need great communication to actually sell

Whether you're a startup founder or an experienced entrepreneur, this episode will challenge how you think about growth, marketing, and success.

#Entrepreneurship #BusinessGrowth #MarketingStrategy #LeadGeneration #SalesSystems #BusinessSuccess #MarketingTechnology #BusinessProcesses #StartupAdvice #EntrepreneurMindset #SmallBusiness #CustomerExperience #BusinessFreedom #ScalableSystems #ExitPlanning

Connect with Mark Osborne:

LinkedIn: https://www.linkedin.com/in/remarkablemark/
Website: https://modernrevenuestrategies.com/

Connect with Derek Dall'Olmo, CFP®, EA:

Email: Derek@tremontefinancial.com
LinkedIn: https://www.linkedin.com/in/derekdallolmo/
Website: https://tremontefinancial.com/about-us/

About TreMonte and Traversing Entrepreneurship Podcast

Traversing Entrepreneurship is a show for and about business owners in Traverse City, Michigan and beyond. In each episode, host Derek Dall'Olmo sits down with local business owners and the professionals who serve them to talk about business building, life, money, taxes, family — and all the ups and downs that come with doing something different. Join us to hear their stories and lessons learned — and to get inspired about what might be possible in your own business.

Derek is the founder of TreMonte Financial Consultants, LLC and TreMonte TreMonte Tax Solutions, LLC (together referred to as "TreMonte"). TreMonte works with business owners and entrepreneurs to develop a proactive tax strategy that maximizes after-tax profits. It is TreMonte's goal to bridge the gap between Financial Advisors and Accountants by serving as CFO to their clients.

This show is for informational purposes only and should not be viewed as personalized financial, investment, tax, or legal advice. You should always consult an attorney or tax professional regarding your specific legal or tax situation.

Please email Derek Dall'Olmo at derek@tremontefinancial.com with questions and comments or to schedule a one-on-one conversation.

This week, Derek sits down with Chris Shihadeh, CEO of Skylab Digital, who shares his entrepreneurial journey, insights on navigating the competitive Medicare space, and the importance of financial literacy in business. Chris discusses the significance of building a strong team, identifying A, B, and C players in hiring, and empowering employees to solve problems. He emphasizes the role of data in digital marketing, managing cash flow in seasonal businesses, and leveraging debt for growth. The conversation concludes with key takeaways for aspiring entrepreneurs, highlighting the importance of understanding financials and learning to say no to distractions.

Takeaways:

Chris started his entrepreneurial journey at a young age.
Financial literacy is crucial for business success.
Building a strong team requires learning from painful lessons.
Identifying A, B, and C players is key in hiring.
Empowering employees to solve problems fosters ownership.
Data-driven decision-making is essential in digital marketing.
Managing cash flow is critical in seasonal businesses.
Leveraging debt can be a powerful tool for growth.
Saying no to distractions is vital for focus.
Understanding your financials is non-negotiable for success.

About TreMonte and Traversing Entrepreneurship Podcast

Traversing Entrepreneurship is a show for and about business owners in Traverse City, Michigan and beyond. In each episode, host Derek Dall'Olmo sits down with local business owners and the professionals who serve them to talk about business building, life, money, taxes, family — and all the ups and downs that come with doing something different. Join us to hear their stories and lessons learned — and to get inspired about what might be possible in your own business.

Derek is the founder of TreMonte Financial Consultants, LLC and TreMonte TreMonte Tax Solutions, LLC (together referred to as "TreMonte"). TreMonte works with business owners and entrepreneurs to develop a proactive tax strategy that maximizes after-tax profits. It is TreMonte's goal to bridge the gap between Financial Advisors and Accountants by serving as CFO to their clients.

This show is for informational purposes only and should not be viewed as personalized financial, investment, tax, or legal advice. You should always consult an attorney or tax professional regarding your specific legal or tax situation.

Please email Derek Dall'Olmo at derek@tremontefinancial.com with questions and comments or to schedule a one-on-one conversation.

TreMonte Facebook Page | Follow Derek on LinkedIn

Subscribe:
Apple Podcast | Google Podcasts | Amazon Podcasts | Stitcher | Spotify | Deezer | TuneIn

If you enjoy the show, please leave a review on iTunes to help others discover the podcast.

In this episode of Traversing Entrepreneurship, Derek Dall'Olmo interviews Eric Stopper, an e-commerce expert and investor, to explore the highs and lows of entrepreneurship. From his early ventures in nanotechnology to his current success with Profitable, Eric shares candid insights into the challenges and triumphs of building a business. Discover how meditation, self-reflection, and a focus on family have shaped his journey.

Key Moments:

• Eric's transition from nanotechnology to e-commerce and investing.
• The importance of self-discovery and meditation in entrepreneurship.
• How Eric balances business with family life.
• Insights into creating cash-flowing assets and financial freedom.

Eric Stopper is an e-commerce entrepreneur and investor. Connect with him on LinkedIn or visit his websites: profitable.com, legendaryitems.com, and zealothealth.com.

If you enjoyed this episode, please leave a review on Apple Podcasts and share it with your business-minded friends. For more insights, visit tramontetax.com to schedule a chat with Derek.

#Entrepreneurship #Ecommerce #BusinessSuccess #FinancialFreedom

About TreMonte and Traversing Entrepreneurship Podcast

Traversing Entrepreneurship is a show for and about business owners in Traverse City, Michigan and beyond. In each episode, host Derek Dall'Olmo sits down with local business owners and the professionals who serve them to talk about business building, life, money, taxes, family — and all the ups and downs that come with doing something different. Join us to hear their stories and lessons learned — and to get inspired about what might be possible in your own business.

Derek is the founder of TreMonte Financial Consultants, LLC and TreMonte TreMonte Tax Solutions, LLC (together referred to as "TreMonte"). TreMonte works with business owners and entrepreneurs to develop a proactive tax strategy that maximizes after-tax profits. It is TreMonte's goal to bridge the gap between Financial Advisors and Accountants by serving as CFO to their clients.

This show is for informational purposes only and should not be viewed as personalized financial, investment, tax, or legal advice. You should always consult an attorney or tax professional regarding your specific legal or tax situation.

Please email Derek Dall'Olmo at derek@tremontefinancial.com with questions and comments or to schedule a one-on-one conversation.

TreMonte Facebook Page | Follow Derek on LinkedIn

Subscribe:
Apple Podcast | Google Podcasts | Amazon Podcasts | Stitcher | Spotify | Deezer | TuneIn

If you enjoy the show, please leave a review on iTunes to help others discover the podcast.