Parallel Entrepreneur with Mark Cleveland
Mark explores the minds of visionary entrepreneurs who refuse to limit themselves to a single venture to learn how these trailblazers manage risks, innovate across industries, and turn ideas into impact. Whether you’re scaling your first business or juggling several, this podcast is your ultimate guide to thriving as a parallel entrepreneur.
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Why Founders Don’t Succeed Alone | Dakota Simpson
<p>In this episode of the Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Dakota Simpson, Chief Program Officer at the Nashville Entrepreneur Center.</p><p>Dakota is focused on a simple idea: founders don’t succeed in isolation. They succeed when the right systems, support, and structure are in place around them.</p><p>At the NEC, he leads the strategy and execution behind accelerator programs and founder development, helping entrepreneurs access the resources, networks, and guidance needed to grow.</p><p>But this conversation goes deeper.</p><p>It’s about what actually drives founde...
Operational Debt Is Slowing Your Company | Stephanie Johnson
<p>In this episode of the Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Stephanie Johnson, a fractional CEO and COO who specializes in helping companies eliminate what she calls operational debt.</p><p>Most leaders recognize technical debt in software. Fewer realize the same concept exists inside organizations.</p><p>Misaligned teams. Unclear processes. Decisions that made sense in the moment but quietly compound over time.</p><p>Stephanie steps into companies during pivotal moments—growth, transition, or pressure—and helps leadership teams reconnect strategy with execution.</p><p>This conversation explores:<br>• What operational debt act...
Strategic Alignment of Talent, Tech & Data | Amy Henderson
<p>In this episode of the Parallel Entrepreneur, Innovation Series, Mark Cleveland and Johnny Anderson sit down with Amy Henderson, Director of Infrastructure at HCA Healthcare Physician Services.</p><p>Amy operates at the intersection of technical viability and business outcomes, aligning talent, technology, and data to drive enterprise growth inside one of the largest healthcare systems in the country.</p><p>But this conversation isn’t just about infrastructure.</p><p>It’s about what it really takes to connect strategy to execution. To build teams that understand both the financial model and the human one. And to develop work...
Women in Tech, Real Relationships & Nashville’s Growth Story | Meg Chamblee
<p>In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Meg Chamblee, Executive Vice President for Tennessee at UDig.</p><p>Meg launched UDig’s Nashville office in 2020 and has grown it more than 10x, building not just a market presence, but a reputation rooted in trust, partnership, and long-term relationships.</p><p>But this conversation goes far beyond growth metrics.</p><p>Meg shares how Nashville’s tech community has evolved, why organizations like Women in Technology of Tennessee (WiTT) matter more than ever, and what it really looks like to lead w...
Designing for Trust: Customer Experience, Bias & the Human–Automation Balance
<p>Great experiences don’t happen by accident. They’re designed.</p><p>In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Suzi Earhart, CCXP, a Customer Experience and Organizational Change executive who believes better experiences begin with intentional design, empathy, and mutual understanding — and end in measurable business results.</p><p>Suzi started her career in computer science before realizing something foundational: technology alone doesn’t create great outcomes. People, process, and technology must work together. And if they aren’t aligned around the customer, trust quietly erodes.</p><p>This conversation...
Why Today’s Leadership Playbook Breaks in the Age of AI
<p>The leadership playbooks that built today’s successful organizations were designed for a different world.</p><p>In this episode of The Parallel Entrepreneur – Innovation Series, hosts Mark Cleveland and Johnny Anderson sit down with Amalia Goodwin, Global Managing Director of Adaptive Organizations at Slalom, to confront a reality most executives quietly avoid:</p><p>Incremental change is no longer safe. It’s organizational suicide.</p><p>Amalia works with C-suite leaders and boards who understand that AI transformation isn’t about tools, it’s about redesigning how organizations sense, decide, and evolve at scale. This conversation goes far beyond tec...
Why the Future of Entrepreneurship Starts in Schools
<p>In this Innovation Series episode of Parallel Entrepreneur, hosts Mark Cleveland and Johnny Anderson sit down with Dr. Jeremy Qualls, Executive Director of the Entrepreneurship & Innovation Center (EIC) and College, Career & Technical Education at Williamson County Schools.</p><p>Jeremy leads one of the most compelling early-stage entrepreneurship models in the region—where students don’t just learn about innovation, they practice it. Inside the EIC, high school students launch real businesses, products, and services while earning academic credit and developing leadership skills that typically come much later in life.</p><p>During the conversation, Jeremy shares examples of how...
Why AI Strategy Fails Before It Starts | Jon Hilton
<p>Why do AI initiatives often stall? What does it take to build AI strategies that scale inside real businesses? What does responsible, human-centered AI look like in practice?</p><p>In this episode of The Parallel Entrepreneur – Innovation Series, Mark Cleveland sits down with Jon Hilton, Shareholder-in-Charge of the LBMC AI Practice, to address these questions. </p><p>Jon brings a rare mix of experience, enterprise data science, large-scale digital transformation, and leadership forged through military service. From this conversation with John, you'll learn:</p><p>- Where AI strategy usually breaks down<br>- How to move from pi...
Stop Doing Tasks AI Can Handle: Shauna Sprague on Automation & Human Potential
<p>In this special Innovation Series episode of Parallel Entrepreneur, hosts Mark Cleveland and Johnny Anderson sit down with Shauna Sprague, an AI strategist, architect, and TEDx speaker with 20+ years of experience helping Fortune 500 organizations navigate technology transformation.</p><p>Shauna is known for helping leaders move beyond the AI hype and into confident execution—building clear roadmaps, designing intelligent workflows and agents, and scaling automation responsibly. She’s led AI initiatives across 49 business units and brings hands-on experience with tools like AWS, Power BI, Zapier, n8n, and LangChain.</p><p><br>In this episode:<br> • Why most people aren’t...
Why Community Is Nashville’s Superpower — A Conversation with S3 CEO Rod McDaniel
<p>In this special Innovation Series episode of Parallel Entrepreneur, hosts Mark Cleveland and Johnny Anderson sit down with Rod McDaniel, CEO of S3 Recycling Solutions and Board Chair of the Greater Nashville Technology Council.</p><p>Rod’s journey, from growing up in public housing in Nashville to leading a nationally recognized, mission-driven tech recycling company, is a powerful example of what community, purpose, and leadership can create.</p><p>In this episode:<br> • Why community is Nashville’s greatest strength<br> • How mobility, transit, and opportunity are deeply connected<br> • What’s fueling Nashville’s new leadership renaissance<br> • How to u...
