Traversing Entrepreneurship

Welcome back to Traversing Entrepreneurship, the show for business owners who set out to do something different and didn't stop there. Coming to you from Traverse City, Michigan, host Derek Dall'Olmo sits down with Rich Kahn, serial entrepreneur and CEO/co-founder of Anura. Episode Highlights 🧠 The Scope of Digital Fraud: Uncover how out of $750 billion spent on digital marketing globally, over $...

In this episode of Traversing Entrepreneurship, Derek Dall'Olmo interviews Katie Brinkley, founder of NextStep Social and Podcasting. They explore Brinkley's journey from aspiring sports reporter to agency owner, how she scaled her business from a solo venture to a team of eight, and the strategies that have helped her thrive in a competitive, male-dominated industry. Brinkley shares lessons on te...

In this episode of the Traversing Entrepreneurship podcast, Derek Dall'Olmo interviews Randy Martinez, a personal and cultural transformation specialist. Randy shares his journey from a successful corporate career to personal transformation, discussing the challenges he faced, including burnout and layoffs. He emphasizes the importance of finding purpose, writing a book, and developing tools for p...

In this episode of Traversing Entrepreneurship, Derek Dall'Olmo sits down with Saul Marquez, founder and CEO of Outcomes Rocket, to unpack what it really takes to go from a secure corporate healthcare job to building a thriving business. You'll hear how Saul made the leap into entrepreneurship with the support of his wife, why marketing in healthcare is non-negotiable, and how to use owned, earned...

In this episode, Derek sits down with Lisa Even , a keynote speaker, bestselling author, and leadership coach known for her "Good Ripple Effect" philosophy. With roots in healthcare operations, Lisa now works with companies like ESPN, SHRM, and Disney to help leaders improve culture, build trust faster, and create more intentional teams. She also hosts the Have a Good Ripple Effect Podcast. The co...

In this inspiring episode, Molly Rose opens up about the real work of empowering individuals—especially women—who are trying to build a career without sacrificing family. She shares heartfelt stories from her program, the unexpected ways coaching changes lives, and the deep satisfaction that comes from helping people create more presence and more income at home. From learning to navigate entrepren...

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 entrepreneur...

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...

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 f...

In this episode Derek sits down with Beau Eckstein, owner of Business Ownership Coach and Emerge Lending Group. With over 26 years of experience, Beau shares his journey from a struggling student to a successful entrepreneur, offering insights into funding strategies, franchise consulting, and the importance of tax strategies. Discover how Beau's experiences, including a stint on HGTV, have shaped...

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...

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 s...

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...

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 negot...

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: sell...

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-b...

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, particul...

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 b...

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...

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 throug...

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 throug...

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 pract...

In this episode, we are joined by Sairan Aqrawi as she shares her remarkable journey from Kurdish immigrant to successful business coach and mentor. After initially struggling to adapt to life in the US, Sairan discovered her true calling in coaching and personal development, transitioning from a decades-long engineering career. She emphasizes the importance of clarity, focus, and grit when pursui...

Ever wonder what it takes to build a successful business from scratch? Join us as we sit down with serial entrepreneur Brad Zapp to get the inside scoop on his journey from wealth management to founding a cutting-edge digital VC firm. You won't want to miss this eye-opening conversation! Brad Zapp is a CFP, was a former founder of an independent Wealth Advisory Firm, sold that, and founded a Digit...

Christophe Dessaigne joins us to share his entrepreneurial journey, from starting a tech company helping blind people to co-founding the online grocery store Jack B. He talks about the challenges of the online grocery industry and how Jack B is tackling them. Christophe also opens up about his personal growth, dealing with childhood wounds, and advice for aspiring entrepreneurs. You do not want to...