Parallel Entrepreneur with Mark Cleveland

There’s a moment in every founder’s journey where the question shifts.Not “What am I building?”But “Who am I becoming?”In this conversation, Mark sits down with Eve Peeterson, an Estonian strategy and transformation leader who has led across private industry, government innovation, and national startup ecosystems.From working her way up in hospitality…To leading Estonia’s startup strategy…To now building a global mentorship platform…This is a conversation about reinvention, leadership, and what it actually takes to build ecosystems that work.They explore the real differences between US and European startup cultures, why mentorship is misunderstood, and how the best leaders keep learning, especially when they’re the ones teaching.And maybe most importantly…Why your next evolution doesn’t require starting over. Just saying yes.What You’ll Learn:- Why “perfect before launch” is holding founders back- The real difference between US and European startup thinking- How mentorship should actually work (and why it usually doesn’t)- Why leadership is the root of culture — whether you like it or not- How to keep reinventing yourself without losing who you areAbout the HostMark Cleveland is an entrepreneur, investor, and advisor who works at the intersection of multiple ventures. As the voice behind The Parallel Entrepreneur, he explores how founders build aligned businesses, strong teams, and sustainable momentum—without forcing themselves into a single path.https://www.linkedin.com/in/macleveland/About the GuestEve Peeterson is an Estonian strategy and transformation leader with over 20 years of experience across hospitality, creative industries, and national innovation. From leading Startup Estonia to building cross-border initiatives like Nordic Tech Valley, she now focuses on leadership development as the founder of Leadrs.online, a mentorship platform designed to make better leadership more accessible.https://www.linkedin.com/in/eve-peeterson/⏱️ Key Moments00:00 – If you’re the smartest in the room…02:10 – Why she came to the U.S. (and what she got wrong)05:10 – Mentorship: Europe vs U.S.07:03 – The mistake founders make: waiting too long to sell08:51 – Reinventing yourself (again and again)14:24 – “Maybe I am an entrepreneur”18:56 – Why Estonia punches above its weight26:40 – Starting over when nobody knows you28:22 – Why teaching is the best way to learn31:14 – The biggest hiring mistake founders make32:43 – Leadership sets the culture40:04 – The decision that changed Estonia’s future43:38 – What innovation actually means49:47 – What she’s taking from this experienceLinks & Resources👉 Join the Parallel Entrepreneur Network:https://www.parallelentrepreneur.com/#about-me👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.

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.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.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.But this conversation goes deeper.It’s about what actually drives founder success beyond the idea.They cover:• Why ecosystems matter more than individual effort• The role of structure in startup success• What founders actually need at different stages• Aligning programs, people, and outcomes• Building more inclusive pathways to growthShort, practical, and grounded in real experience.Links - https://www.boringcompany.com/- https://technologycouncil.com/- https://nashvillechamber.com/- https://ec.co/- https://williamsonchamber.com/About the GuestDakota Simpson is Chief Program Officer at the Nashville Entrepreneur Center, where he leads startup accelerators and founder programming. With a background in government and nonprofit leadership, he focuses on building systems that improve access, strengthen execution, and help entrepreneurs grow with clarity and support.https://www.linkedin.com/in/dakota-simpson-566358306/About the HostsMark A. ClevelandManaging Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Networkhttps://www.linkedin.com/in/macleveland/Johnny AndersonNashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™https://www.linkedin.com/in/johnnyonbrand/Links & Resources👉 Learn more about the Entrepreneurship & Innovation Center (EIC):https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic👉 Join the Parallel Entrepreneur Network:https://www.parallelentrepreneur.com/#about-me👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.Chapters00:00:00 Speed to market and why it matters00:00:50 Meet Dakota Simpson + role overview00:01:54 What innovation actually means00:02:40 Building a founder support system00:03:42 The current surge in entrepreneurship00:05:02 Growth in founder demand and programs00:06:14 Shifts in founder demographics00:07:46 Younger founders entering earlier00:09:08 The rise of the parallel entrepreneur00:10:32 Lower barriers and earlier risk-taking00:11:05 Entrepreneurship by acquisition00:11:37 AI’s impact on founders00:12:30 What AI means for SaaS and business models00:13:55 Speed of change and access to knowledge00:15:00 What founders actually need to succeed00:17:30 Building systems that support growth00:19:30 Final thoughts on supporting entrepreneurs00:21:00 Episode close

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.Most leaders recognize technical debt in software. Fewer realize the same concept exists inside organizations.Misaligned teams. Unclear processes. Decisions that made sense in the moment but quietly compound over time.Stephanie steps into companies during pivotal moments—growth, transition, or pressure—and helps leadership teams reconnect strategy with execution.This conversation explores:• What operational debt actually looks like inside organizations• Why strategy often fails at the execution layer• How leaders stabilize teams during change• The hidden friction slowing growth• What it takes to realign people, systems, and performanceIf you’ve ever felt like your business should be moving faster than it is, this conversation will resonate.About the Stephanie JohnsonStephanie Johnson is a fractional and interim CEO/COO who helps organizations navigate complexity, stabilize operations, and drive sustainable growth. Known for her ability to quickly assess challenges and reconnect strategy with execution, she works with leadership teams to improve performance, strengthen alignment, and eliminate operational friction. Stephanie has led across global teams and organizations, bringing a balance of operational rigor, executive leadership, and people-centered transformation.About the HostsMark A. ClevelandManaging Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Networkhttps://www.linkedin.com/in/macleveland/Johnny AndersonNashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™https://www.linkedin.com/in/johnnyonbrand/Links & Resources👉 Learn more about the Entrepreneurship & Innovation Center (EIC):https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic👉 Join the Parallel Entrepreneur Network:https://www.parallelentrepreneur.com/#about-me👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.Chapters00:00:00 The idea of operational debt00:00:44 Episode introduction + Stephanie’s leadership focus00:01:10 What operational debt looks like inside companies00:02:05 Why strategy often breaks at execution00:02:58 Stepping into organizations during pivotal moments00:03:47 Aligning leadership teams around clarity and accountability00:04:39 Finding the friction slowing growth00:05:26 Stabilizing teams during transformation00:06:19 Reconnecting strategy with operational discipline00:07:12 Leadership lessons from high-stakes environments00:08:05 Final thoughts on eliminating operational debt

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.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.But this conversation isn’t just about infrastructure.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 workforce pipelines that strengthen an entire region.Amy also reflects on her decade of service with the Nashville Technology Council, including her time as Board Chair, where she helped advocate for technology-focused workforce development across Tennessee, from K-12 to career changers.This episode explores:• Why strategic alignment is a leadership discipline• Operating technical teams inside financial guardrails• Building culture while scaling enterprise systems• Workforce development as a long-term investment• The role Nashville plays in shaping tech leadershipIf you care about the future of enterprise leadership — especially where technology meets execution — this conversation is worth your time.About Amy HendersonAmy Henderson is Director of Infrastructure at HCA Healthcare Physician Services, where she aligns talent, technology, and data to drive enterprise performance in complex healthcare environments. With a focus on connecting technical strategy to business outcomes, she builds high-performing teams that operate with both financial discipline and cultural strength. Amy also served for a decade on the Nashville Technology Council Board, including as Chair, where she championed workforce development across Tennessee’s tech ecosystem.https://www.linkedin.com/in/henderson-amy/About the HostsMark A. ClevelandManaging Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Networkhttps://www.linkedin.com/in/macleveland/Johnny AndersonNashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™https://www.linkedin.com/in/johnnyonbrand/Links & Resources👉 Learn more about the Entrepreneurship & Innovation Center (EIC):https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic👉 Join the Parallel Entrepreneur Network:https://www.parallelentrepreneur.com/#about-me👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.Chapters00:00:00 The intersection of tech viability and business goals00:00:41 Episode introduction + Amy’s leadership focus00:01:07 Amy’s role at HCA Healthcare Physician Services00:01:54 Aligning talent, tech, and data inside enterprise systems00:02:48 Operating to a financial model while scaling teams00:03:39 Building culture within infrastructure organizations00:04:28 Why workforce development matters in Tennessee00:05:27 Serving on the Nashville Technology Council00:06:18 Developing talent pipelines from K-12 to career changers00:07:32 Leadership lessons from board service and enterprise growth00:08:36 Episode close

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.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.But this conversation goes far beyond growth metrics.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 with both excellence and inclusion.As a past president of WiTT and a board leader at the Greater Nashville Technology Council (GNTC), Meg has helped shape the ecosystem that supports emerging leaders, especially women navigating technology careers in Middle Tennessee.This episode explores:• Why community is a strategic advantage in Nashville• How WiTT is creating access, confidence, and opportunity for women in tech• The power of real relationships in building sustainable growth• What enterprise clients actually need from digital transformation partners• How leadership evolves as companies scale• Why investing in people outlasts investing in hypeIf you care about technology, leadership, and building something that lasts in this city, this conversation is for you.Learn more about WiTT: https://www.wittn.org/Connect with Meg: https://www.linkedin.com/in/megchamblee/About Meg ChambleeMeg Chamblee is Executive Vice President for Tennessee at UDig, a technology consulting firm that designs and builds custom digital workflows and experience solutions for enterprise clients. She founded and leads UDig’s Nashville office, which has grown more than 10x since 2020.Meg is a past president of Women in Technology of Tennessee (WiTT), serves on the board of the Greater Nashville Technology Council (GNTC), and co-founded the ELITE (Emerging Leaders in Technology) program. She has been recognized as an NBJ 40 Under 40 honoree and is a longtime advocate for building inclusive leadership pipelines across Middle Tennessee.About the HostsMark A. ClevelandManaging Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Networkhttps://www.linkedin.com/in/macleveland/Johnny AndersonNashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™https://www.linkedin.com/in/johnnyonbrand/Links & Resources👉 Learn more about the Entrepreneurship & Innovation Center (EIC):https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic👉 Join the Parallel Entrepreneur Network:https://www.parallelentrepreneur.com/#about-me👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.Chapters 00:00:00 The reality of being the only woman in the room 00:00:52 Episode introduction + framing Meg’s leadership 00:01:01 Meg Chamblee, UDig, and launching Nashville 00:01:47 Why relationships drive real growth 00:02:03 Nashville’s tech ecosystem and connection culture 00:03:00 The impact of WiTT in Nashville 00:04:02 Community as the foundation for scaling 00:05:00 Leadership lessons from growing a market 00:06:01 Investing in people and showing up to serve 00:07:00 Board service, volunteer leadership, and long-term impact 00:07:42 Episode close

Great experiences don’t happen by accident. They’re designed.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.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.This conversation goes beyond surface-level CX talk. We explore how leaders unintentionally design from the inside out, how unconscious bias limits true “outside-in” thinking, and why deciding between human, assisted, or self-service interactions is one of the most strategic trust decisions a company makes.In this episode, we discuss:- Why incentives today are tied to identity and belonging- The challenge of truly thinking “outside-in”- How culture and bias distort customer-centered design- The difference between human, assisted, and automated experiences- Why innovation requires structured change management- Assessing whether employees are truly set up to deliver quality- How aligned CX creates both financial and relational wealthAt just over 12 minutes, this episode delivers practical insight for founders, operators, and leaders responsible for shaping experience at scale.About the GuestSuzi Earhart, CCXP is a Customer Experience and Organizational Change executive based in Denver, Colorado. She is passionate about improving experiences through intentional design, empathy, and mutual understanding — outcomes she believes must ultimately be proven in business results.Beginning her career in Computer Science, Suzi quickly recognized that sustainable innovation requires alignment across people, process, and technology. Her work focuses on helping organizations think like their customers, challenge unconscious bias, and intentionally decide when to use human, assisted, or self-service models.She holds certifications in change management and has led initiatives including:- Strategic and technology roadmaps- Journey mapping and Voice of the Customer systems- Service delivery redesign- Organizational change management programs- Governance system creation- Employee capability and “do-ability” assessmentsThroughout her career, she has remained committed to servant leadership and mentoring — helping others reach their full potential while building systems that deepen trust and results.Connect with Suzi here: https://www.linkedin.com/in/suzi-earhart-ccxp-220663/About the HostsMark A. ClevelandManaging Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Networkhttps://www.linkedin.com/in/macleveland/Johnny AndersonNashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™https://www.linkedin.com/in/johnnyonbrand/Links & Resources👉 Learn more about the Entrepreneurship & Innovation Center (EIC):https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic👉 Join the Parallel Entrepreneur Network:https://www.parallelentrepreneur.com/#about-me👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.Chapters:00:00:00 Incentives, Identity & Brand Association00:00:49 Episode Introduction00:01:41 Suzi’s Background: Tech, People & CX00:02:00 Why Innovation Demands Change00:04:01 Brand as Identity & Belonging00:05:01 The Full Customer Ecosystem00:06:00 Designing Platforms Customers Struggle With00:07:00 Fitting Into the Fabric of Customers’ Lives00:09:00 “Our Customers Don’t Understand”00:10:01 Perspective, Bias & Trust Decisions00:12:01 Innovation as Intentional Design

The leadership playbooks that built today’s successful organizations were designed for a different world.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:Incremental change is no longer safe. It’s organizational suicide.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 technology and into the deeper work of leadership courage, organizational design, and the role companies play as architects of society’s future.We explore what it actually means to build an adaptive organization, one capable of continuous reinvention rather than reactive survival.In this episode, we discuss:- Why AI transformation fails without leadership courage- The danger of applying yesterday’s playbooks to tomorrow’s problems- What “innovation metabolism” really means inside organizations- How leaders can balance quarterly performance with long-term survival- Why organizations must see themselves as civic architects, not just profit engines- Designing decision-making systems that can keep pace with exponential change- The overlooked societal impact of AI governance and organizational choicesAmalia brings insights shaped by 25+ years and 100+ global transformations, blending strategic clarity with moral responsibility. This is a conversation for leaders who know the future isn’t something you react to, it’s something you design.Chapters: 00:00:00 “Courage feels a lot like fear when you’re in it.” (Cold open) 00:00:47 Episode introduction + why this conversation matters 00:01:07 The systems that made you successful won’t survive the AI age 00:01:16 Why incremental change is actually dangerous right now 00:01:37 Amalia on helping organizations succeed in a technology shift 00:03:54 “The definition of value is changing.” 00:04:22 How companies are evaluating AI strategy (M&A lens) 00:05:23 Adaptive leadership + reinvesting in continuous change 00:06:00 Learning velocity as a new measure of value 00:06:25 Decision velocity: when do leaders know enough to move? 00:07:27 “Innovation metabolism” — how leaders fuel themselves differently 00:07:56 Addressing fear in strategic decision-making 00:08:13 It’s okay to be afraid — making AI adoption fun (Bingo + games) 00:09:59 The moment AI “blew me away” (and rewrote an SOW) 00:10:29 The real leader work: humility, new mindsets, new skill sets 00:10:41 “Courage feels a lot like fear when you’re in it.” (Expanded) 00:11:28 Relearn vs. Unlearn — why unlearning is harder 00:12:23 Six-month roadmaps vs. 3-year plans 00:13:19 Massive 30-year transformative vision 00:14:01 AI as a playground — bringing back play 00:15:03 Hackathons, bake-offs, and low-code teams winning 00:16:00 Agentic workflows + giving unexpected leaders a stage 00:16:55 Closing: “A bake-off sounds like the right answer.”About the GuestAmalia Goodwin is the Global Managing Director of Adaptive Organizations at Slalom, where she partners with C-suite leaders and boards to reimagine how organizations lead through exponential disruption.Her work focuses on the intersection of AI transformation, leadership courage, and organizational responsibility, helping companies design systems capable of continuous reinvention. Amalia is a recognized thought leader on adaptive strategy and organizational courage, with insights featured in Fortune, Forbes, HR.com, Unite.AI, and Slalom’s global research on AI-enabled organizations.She is known for introducing leaders to what she calls “innovation metabolism”, the capacity to transform fast enough to survive, without being consumed by change itself.🔗 Connect with Amalia on LinkedIn:https://www.linkedin.com/in/amaliagoodwin/About the HostsMark A. ClevelandManaging Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Networkhttps://www.linkedin.com/in/macleveland/Johnny AndersonNashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™https://www.linkedin.com/in/johnnyonbrand/Links & Resources👉 Learn more about the Entrepreneurship & Innovation Center (EIC):https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic👉 Join the Parallel Entrepreneur Network:https://www.parallelentrepreneur.com/#about-me👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.

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.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.During the conversation, Jeremy shares examples of how this model comes to life, including:Anthony Beckett, founder of Markify → http://Markifyapp.comAbigail Goddard, National Program Champion and creator of Spikey First → http://Spikeyfirst.comThese stories reflect what the EIC is built to do: help students move from ideas to execution, and from confidence to ownership.Under Jeremy’s leadership, the EIC has grown from 70 students to more than 500 applicants, secured over $17 million in grants, and built a mentor network of 100+ business and community leaders—all focused on developing entrepreneurial thinkers early.In this episode, we explore:Why entrepreneurship is a mindset, not a job titleHow leadership development changes when it starts earlierWhat founders can learn from education systems—and vice versaWhy culture and coaching matter more than curriculumHow community partnerships create real-world opportunityCHAPTERS 00:00:00 Entrepreneurship as the Heartbeat, Not a Track 00:00:50 Building the Future of Work Before It Starts 00:01:00 Jeremy Qualls and the Vision Behind the EIC 00:01:45 Rethinking Traditional Career & Technical Education 00:02:15 From Ideas to Action: National Pitch Competitions 00:03:10 Teaching Business Plans, Ownership, and Real Skills 00:04:10 Why Culture and Coaching Matter More Than Curriculum 00:05:20 Discovering What’s Possible: The Markify Story 00:06:30 Giving Students Real Responsibility Early 00:07:35 Mentorship, Trust, and Community Partnerships 00:08:50 When Student Ideas Become Real Businesses 00:10:05 Scaling Leadership Development Inside a System 00:11:40 What Schools and Founders Can Learn From Each Other 00:13:10 Building Confidence Before Credentials 00:14:30 Why Starting Earlier Changes Everything 00:15:40 Final Reflections on Leadership and OpportunityABOUT OUR GUESTDr. Jeremy Qualls is the Executive Director of the Entrepreneurship & Innovation Center (EIC) and College, Career & Technical Education for Williamson County Schools. A leadership strategist, coach, and educator with more than two decades of experience, Jeremy has built a people-first model for developing entrepreneurial thinkers and future leaders. Under his leadership, the EIC has grown from 70 students to more than 500 applicants, secured over $17 million in grants, and built a mentor network of 100+ business and community leaders. His work focuses on cultivating culture, ownership, and leadership at every level.ABOUT THE HOSTSMark A. Cleveland — Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network.https://www.linkedin.com/in/macleveland/Johnny Anderson — Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the EC, and host of The Impodsters™.https://www.linkedin.com/in/johnnyonbrand/👉 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/#about-me👉 Subscribe for more stories from entrepreneurs who thrive across multiple ventures—and live aligned lives.👍 Like this episode? Leave a comment or share it with someone who leads across lanes.👉 Join the Parallel Entrepreneur Network: (link below)👉 Subscribe for more Innovation Series conversations with builders and operators.👍 Like this episode? Leave a comment or share it with someone who’s ready to make AI practical.#ParallelEntrepreneur, #InnovationSeries, #EntrepreneurshipEducation, #LeadershipDevelopment, #FutureOfWork

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?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. 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:- Where AI strategy usually breaks down- How to move from pilots to production without chaos- Why clarity beats complexity every time- The leadership mindset required to scale AI responsibly- This conversation is for executives, founders, and operators who want results, not hype.CHAPTERS: 00:00:00 AI Isn’t a Technology Problem — It’s a Leadership Problem 00:00:40 Introducing Jon Hilton: Leading AI Practice at LBMC 00:01:47 The Strategy Disconnect: Executives vs. Employees 00:02:40 West Point + Combat Tours: Leading Through Fear, Chaos & Uncertainty 00:03:55 Building the Veterans Tech Peer Group in Nashville 00:04:57 Military Technology + Nashville: What’s Being Built and Why It Matters 00:06:27 The AI Tool Explosion: Don’t Chase Tools — Define the Problem 00:08:25 AI’s Expanding Attack Surface: Scams, Security & New Risks 00:09:42 “In Absence of Orders, Attack”: Courage and Forward Motion in AI 00:10:24 Avoiding Paralysis: Deliberate Action Without Rushing 00:12:03 Bringing People Along: Sentiment, Trust & Internal Buy-In 00:12:55 Leveraging Veterans Well: What Corporate Leaders Need to Understand 00:13:31 Translating Military Experience to Corporate Value (Network + Skills) 00:15:10 Closing Thanks & Service AppreciationABOUT OUR GUESTJon Hilton helps organizations turn AI from an experiment into a scalable capability. As Shareholder-in-Charge of LBMC’s AI Practice, he works with leadership teams to define practical AI strategies, identify where automation and intelligence actually create value, and build systems that can scale responsibly across the organization. A data scientist by training with experience at ExxonMobil and EY, Jon brings a disciplined, execution-first perspective shaped by enterprise environments and military leadership. His work focuses on helping leaders make better decisions about when to use AI, where to apply it, and how to do so without creating risk, chaos, or wasted investment.https://www.linkedin.com/in/jonathan-hilton/ABOUT THE HOSTSMark A. Cleveland — Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network.https://www.linkedin.com/in/macleveland/Johnny Anderson — Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the EC, and host of The Impodsters™.https://www.linkedin.com/in/johnnyonbrand/👉 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/#about-me👉 Subscribe for more stories from entrepreneurs who thrive across multiple ventures—and live aligned lives.👍 Like this episode? Leave a comment or share it with someone who leads across lanes.

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.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.In this episode: • Why most people aren’t afraid of AI — they’re just overwhelmed by it • How to move from curiosity to confident AI execution (without getting lost in buzzwords) • The “automate the mundane” mindset that gives teams time back for meaningful work • A parent-friendly AI hack: photo → sports schedule → fully automated calendar • The first practical tools to start with, even if you don’t have a big budget or deep technical expertise • When to use workflows, automation, RPA, and when it’s time for AI agents • Why working at the top of your skill set is becoming the new competitive advantage • How to scale AI responsibly,and why human-centered, inclusive AI mattersShauna brings clarity, humility, and a deep sense of purpose to a topic that feels overwhelming for a lot of teams. If your organization has been circling AI wondering where to start, this conversation will help you take the next step ,with confidence.Chapters: 00:00:00 “Eliminate the task — make yourself valuable” 00:01:13 Introducing Shauna Sprague + what this episode is about 00:02:45 Shauna’s core idea: automate the mundane, protect the human work 00:03:34 The parent use-case: photo → sports/school schedule → calendar automation 00:04:02 Daily AI assist: meeting digest + LinkedIn “who I’m meeting with” rundown 00:05:33 Why resistance is normal (and how skeptics become champions) 00:05:52 The low-cost starting point: RPA tools for ~$20/month 00:06:09 When teams “graduate” to agents (LangChain / LangGraph) 00:06:41 Working at the top of your skill set (sales example: stop the busywork) 00:07:50 The empowering question: “Where do I start with AI?” 00:08:15 First recommendation: Zapier + plug-and-play automations 00:08:40 Practical example: Gmail automation + VIP alerts (and filtering sales emails) 00:09:13 Time back unlocks creativity (resources aren’t the limiter anymore) 00:10:02 Upskill move: build something in n8n + become the hero 00:10:26 Closing thought: “They don’t lay off valuable people”ABOUT OUR GUEST Shauna Sprague is an AI strategist, architect, and TEDx speaker with 20+ years in technology innovation. She has led AI and automation initiatives across 49 business units, built intelligent workflows and agents, and developed AI personas that streamline operations and increase efficiency. She’s also a board member, STEM advocate, and champion for inclusive innovation.https://www.linkedin.com/in/shaunasprague/ABOUT THE HOSTSMark A. Cleveland — Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network.https://www.linkedin.com/in/macleveland/Johnny Anderson — Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the EC, and host of The Impodsters™.https://www.linkedin.com/in/johnnyonbrand/👉 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/#about-me👉 Subscribe for more stories from entrepreneurs who thrive across multiple ventures—and live aligned lives.👍 Like this episode? Leave a comment or share it with someone who leads across lanes.👉 Join the Parallel Entrepreneur Network: (link below)👉 Subscribe for more Innovation Series conversations with builders and operators.👍 Like this episode? Leave a comment or share it with someone who’s ready to make AI practical.#ShaunaSprague #ParallelEntrepreneur #InnovationSeries #AILeadership #PracticalAI #AIStrategy #Automation #AIForBusiness #FutureOfWork #HumanCenteredAI #InclusiveAI #DigitalTransformation #NashvilleTech #Entrepreneurship #LeadershipPodcast

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.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.In this episode: • Why community is Nashville’s greatest strength • How mobility, transit, and opportunity are deeply connected • What’s fueling Nashville’s new leadership renaissance • How to use “dead time”, traffic, commutes, swims, for growth • Why passion outside of work strengthens culture inside it • How companies relocating to Nashville are shaking things up • The surprising role of musicians, artists & creators in tech culture • The city’s collaborative DNA, and how to protect itRod’s story is as grounded as it is extraordinary, and this conversation is filled with the kind of insight that only comes from someone who’s built a life on purpose, service, and second chances.Chapters: 00:00:00 Introducing Rod McDaniel: Competitive Drive & Entrepreneurial Roots 00:01:10 Early Lessons from Sports, Discipline & Team Culture 00:03:05 Learning to Win Without Burning Out 00:05:00 First Ventures and the Reality of Risk 00:07:15 Navigating Failure, Pressure & Self-Doubt 00:09:40 Building Confidence Through Repetition and Trust 00:12:05 Leadership Beyond the Title 00:14:30 Accountability, Standards & Personal Ownership 00:17:00 What Real Grit Looks Like Over Time 00:19:20 Building Teams That Actually Work 00:21:45 The Importance of Culture Before Scale 00:24:10 Why People Matter More Than Process 00:26:30 Decision-Making Under Uncertainty 00:29:00 Growth, Patience & Long-Term Thinking 00:31:25 Lessons Learned the Hard Way 00:33:40 Balancing Ambition with Perspective 00:36:00 Redefining Success at Different Stages 00:38:30 Community, Connection & Giving Back 00:41:00 Nashville’s Role in Shaping Leaders 00:43:20 Creating Impact Beyond Business 00:45:40 Advice for Founders in the Middle 00:48:10 Staying Grounded While Scaling 00:50:30 Final Reflections on Leadership & LegacyABOUT OUR GUESTRod McDaniel is CEO of S3 Recycling Solutions, a 5x Inc. 5000 company and Best Place to Work honoree. A native Nashvillian and community advocate, Rod has driven more than 3,000% revenue growth, speaks nationally on sustainability and leadership, and serves on major boards including the Nashville Entrepreneur Center and Nashville Technology Council.https://www.linkedin.com/in/rod-mcdaniel-7478729/ABOUT THE HOSTSMark A. Cleveland — Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network.https://www.linkedin.com/in/macleveland/Johnny Anderson — Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the EC, and host of The Impodsters™.https://www.linkedin.com/in/johnnyonbrand/👉 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/#about-me👉 Subscribe for more stories from entrepreneurs who thrive across multiple ventures—and live aligned lives.👍 Like this episode? Leave a comment or share it with someone who leads across lanes.#RodMcDaniel #S3Recycling #NashvilleTech #LeadershipPodcast #MissionDrivenBusiness #CommunityLeadership #EntrepreneurStory #Inc5000 #SustainabilityTech #FaithAndBusiness #PurposeDrivenLeadership

What happens when a city stops waiting for permission and starts acting like the technology hub it already is?You get Nashville’s tech moment, and leaders willing to build it together.Mark Blaze is the kind of leader communities grow around. As President & CEO of the Greater Nashville Technology Council, he’s less interested in headlines and more focused on connection, collaboration, and long-term impact.In this Innovation Series episode, recorded live at the Greater Nashville Technology Council Innovation Summit, Mark joins hosts Mark Cleveland and Johnny Anderson for a grounded, honest conversation about what makes Nashville different, and what it will take to turn momentum into global prominence.If you care about ecosystems, talent, leadership, and building something bigger than any one company, this conversation is for you.In this episode:• Why Nashville already has “all the pieces of the puzzle” • How public–private partnership accelerates real innovation • What servant leadership looks like at a city-wide scale • The importance of finding, developing, and retaining tech talent • Why collaboration — not competition — is the region’s real advantage • How reverse mentorship strengthens modern leadership • What it will take for Nashville to earn worldwide tech prominenceChapters: 00:00:00 Welcome to the Innovation Series from the Nashville Innovation Summit 00:01:20 Introducing Mark Blaze & the Greater Nashville Technology Council 00:02:35 Why Nashville Is the Best Place to Start and Grow a Business 00:03:55 Geographic Advantage, Tax Policy & Momentum 00:05:10 “We Have the Height” — Nashville’s Natural Gifts 00:06:30 Collaboration as a Competitive Advantage 00:07:45 Servant Leadership and Mark’s Influences 00:09:10 Learning from Reverse Mentorship 00:10:40 Government as a Partner in Innovation 00:12:20 Public & Private Investment Working Together 00:13:55 What’s Still Missing — And Why Nothing Is Broken 00:15:30 Connecting Talent, Capital & Opportunity 00:17:10 The Vision for Nashville’s Tech Ecosystem in 3 Years 00:18:45 Finding, Developing & Retaining Talent 00:20:30 The Region’s “Special Sauce”: Its People 00:22:10 Final Thoughts on Community, Leadership & What’s NextShow Notes:Share and engage with this interview on LinkedIn: Click hereConnect with Mark Blaze• LinkedIn – Mark Blaze • Greater Nashville Technology Council – technologycouncil.comAbout Our Hosts• Mark Cleveland — Managing Director at Kensington Park Capital, founder, M&A strategist, and host of The Parallel Entrepreneur • Johnny Anderson — Entrepreneur-in-Residence at the Nashville Entrepreneur Center, advisor, and tech community leader👉 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/#about-me👉 Subscribe for more stories from entrepreneurs who thrive across multiple ventures—and live aligned lives.👍 Like this episode? Leave a comment or share it with someone who leads across lanes.

What happens when a cybersecurity veteran automates the work his competitors still struggle to deliver? He builds the future—and lets them use it.Michael Peters is a rare kind of founder: one who leads both with technical depth and creative clarity. In this episode, we dive into the frameworks behind his companies Lazarus Alliance and Continuum GRC, the origin of the HORSE Project, and how he balances operational intensity with deep personal discipline.If you're building more than one thing—and trying to stay grounded while doing it—this conversation is for you.In this episode:• How Michael turned spreadsheet pain into an AI-driven compliance platform• His decision to turn down a major buyout• What it means to lead a “family-responsible” company• How he manages time, noise, and multiple companies with intention• His upcoming leap from cybersecurity to sci-fi storytellingChapters:00:00:00 Introducing Michael Peters: Venture Catalyst & Cybersecurity Pioneer00:01:52 Lazarus Alliance: Audits, Compliance & Global Reach00:04:15 From “Spreadshits” to Automation: Birth of Continuum GRC00:05:03 The HORSE Project: One Question, Many Frameworks00:06:21 Automating the Boring Stuff00:06:45 Pivoting to Continuum GRC and Passing on a Buyout00:09:41 Navigating Jurisdictions: From FedRAMP to GDPR00:11:07 Why We Let Competitors White-Label Our Tech00:12:18 My First Business: Cannons, Cabins & Capitalism at Age 900:13:34 Hacking Bell Labs and Exploring the Internet in the 90s00:14:49 Selling My ISP in 1995 Before the Web Was Cool00:16:00 Using AI to Transform Compliance & Technical Writing00:17:30 Time Management, Focus Time, and Email Discipline00:20:08 Structure, Boundaries, and Protecting Family Time00:22:45 Creating a Family-Responsible Culture at Work 00:25:50 Managing Auditors vs. Software Creatives00:27:20 Overcoming Upward Delegation with Great Leadership00:28:35 Aligning Vision Across Two Very Different Companies00:30:00 The Traits That Make Parallel Entrepreneurs Thrive00:31:30 Why I Work in 15-Minute Bursts00:33:01 Advice to My Younger Self: Be Bolder00:35:30 The Power of Younger Friends and a Growth Mindset00:37:21 Books on Our Nightstands00:38:50 Engineering Meets Creativity in My Daily Workflow00:40:30 Solving Problems Before They Become Disasters00:41:42 Biggest Challenge: Bureaucracy vs. Innovation00:43:29 What’s Next: A Sci-Fi Trilogy at 4 A.M.00:46:32 The Books I’ve Written and the LifeLock Exit00:48:19 Togetherness, Legacy, and Mars00:50:49 What You Didn’t Ask: The Secret Sauce I Won’t ShareShow Notes:Share and engage with this interview on LinkedIn: Click hereConnect with Michael Peters - LinkedIn – Michael PetersContinuum GRC - continuumgrc.comLazarus Alliance - lazarusalliance.comTo Sell is Human: The Surprising Truth about Moving Others by Daniel Pink - https://www.danpink.com/books/to-sell-is-human/ The Crowd: A Study of the Popular Mind by Gustave Le Bon - https://www.amazon.com/Crowd-Study-Popular-Mind/dp/1636000169 Time Anxiety by Chris Guillebeau - https://www.timeanxiety.com/ Securing the C Level: Getting, Keeping, or Reclaiming that Executive Title by Michael Peters - https://www.amazon.com/Securing-Level-Getting-Reclaiming-Executive/dp/146796882X The Holistic Operational Readiness Security Evaluation: HORSE Project Series: Governance Documentation and Information Technology Security Policies Demystified by Michael Peters - https://www.amazon.com/Holistic-Operational-Readiness-Security-Evaluation/dp/1468063871 👉 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/#about-me👉 Subscribe for more stories from entrepreneurs who thrive across multiple ventures—and live aligned lives.👍 Like this episode? Leave a comment or share it with someone who leads across lanes.

In this episode of The Parallel Entrepreneur, Mark Cleveland welcomes Carla Bailo—an industry visionary who’s helped shape the future of mobility, from General Motors and Nissan to leading the Center for Automotive Research and winning the USDOT Smart City Challenge for Columbus, Ohio. Carla shares stories of innovation, mentorship, boardroom leadership, and the importance of building systems that serve every citizen.Carla's bold curiosity and relentless learning has had great impact on transportation, public policy, and corporate governance. From deploying bus rapid transit in underserved neighborhoods to baking the perfect baguette, this episode celebrates the human side of engineering and entrepreneurship.Chapters List:00:00:00 – Introduction to Carla Bailo00:01:00 – Carla's Impact on Cities and Roads00:03:19 – Columbus Wins the Smart Cities Challenge00:06:50 – Rethinking Mobility for Underserved Communities00:10:13 – Logistics Innovation: Rickenbacker Middle-Mile Project00:12:45 – A Flyer on the Door: Communication Gaps in Tech Projects00:15:23 – Paralleling Transportation, Economic Access, and Planning00:18:36 – Start Small, Learn Fast: Scaling Smart City Systems00:21:24 – Asking Better Questions: Carla’s Mentoring Style00:23:33 – Think in Seven Generations: Long-Term Urban Planning00:25:58 – Carla on Joining Corporate Boards and Boardroom Roles00:28:00 – Lessons from Her Father on Responsibility and Preparation00:32:29 – Learning Upstream Oil & Gas Through Hands-On Curiosity00:34:20 – CEO Oversight and Navigating Shifting Political Climates00:37:22 – What Makes a Great Board and a Good CEO00:40:55 – Mentoring Done Right: Listening and Mutual Learning00:46:50 – Grandparent Wisdom and Generational Teaching00:49:49 – The Joy of Embracing the Unknown00:53:07 – Baking Baguettes & Balancing Curiosity with Relaxation00:54:40 – Surviving as a Woman Engineer in the ‘70s and ‘80s00:57:54 – Final Reflections: Making a Difference at ScaleShow Notes:Share and engage with this interview on LinkedIn: Click hereCarla Bailo, NACD.DC on LinkedIn - https://www.linkedin.com/in/carla-bailo-nacd-dc-604ba19/ Smart Columbus - https://smartcolumbus.com/?utm_source=chatgpt.com US Department of Transportation’s Smart City Challenge - https://www.transportation.gov/briefing-room/us-department-transportation-announces-columbus-winner-unprecedented-40-million-smart Society of Automotive Engineers – https://www.sae.org/ Automotive Women’s Alliance Foundation - https://awafoundation.org/ The Road to the Top is Not on the Map: Conversations with Top Women of the Automotive Industry by Carla Bailo – https://www.amazon.com/Road-Top-Not-Map-Conversations/dp/0768000920The Road Forward: More Conversations with Top Women in the Automotive Industry by Carla Bailo – https://www.sae.org/publications/books/content/r-513/ Women in Mobility Bundle by Carla Bailo - https://www.amazon.com/Women-Mobility-Bundle-Carla-author/dp/1468603574/ Enjoy this episode? Don't forget to like, subscribe, and share with fellow entrepreneurs! For more insights and to join our community, visit parallelentrepreneur.com.

Welcome back to The Parallel Entrepreneur for part 2 with British-American polymath Matthew Joynes. In this fast-paced sequel we dive into:• How Matthew rescued a bankrupt currency-trading firm and scaled it to $1 B+ in volume.• Why he calls Bitcoin “a collectible—like Beanie Babies” and predicts its slide back to reality.• Dollar dominance, tariffs as modern-day tribute, and the hidden mechanics of fiat liquidity.• AI-driven disruption—from accountants to animation studios—and the rise of “one-person unicorns.”• Freedom as America’s true currency, and how Gen-Z parallel entrepreneurs can seize the moment.Stick around to the end for Matthew’s no-BS advice on patents, cap tables, and turning unused assets into new revenue with AI.Chapters:00:00:00 Matthew Joynes Show Teasers00:00:32 Part 2 Kick-Off With Matthew Joynes00:01:19 From Law to Saving a Bankrupt FX Firm00:04:28 Market Manipulation: Gold, Silver, Currencies00:06:12 Bitcoin Debate: Commodity or Currency?00:09:39 Crypto Regulation & Generational Wealth Gaps00:11:20 Money Creation: Share Price as Printing Press00:13:00 “Bitcoin Is a Beanie Baby”00:13:54 Why the Dollar’s Purchasing Power Rose00:14:44 Tariffs, China’s Trap & Deflation Forces00:17:11 Digital Dollar, CBDCs & Surveillance Risks00:18:28 Freedom as America’s Ultimate Currency00:22:21 Rethinking Value in an AI-Robot Economy00:23:59 Tariffs Through a Business Lens00:25:15 Tribute Economy & the Stock-Market Train00:31:01 Adapt, Adopt, Change: Redefining Failure00:33:54 Patent Wars Versus Creative Marketing00:35:37 Why Patents Usually Waste Money00:38:50 Gen-Z’s Parallel Entrepreneurship Boom00:41:54 Pinpoint Apps & the Free-Service Model00:45:40 Renting Idle Assets With AI Matching00:47:27 Knowledge Is Cheap, Everything as a Rental00:49:12 Phones, Cubes & Voice-First Futures00:51:38 “Spend the $20 and Learn AI”00:53:37 Animation Disrupted: IP vs. Algorithms00:56:00 Final Takeaways & Thanks to MatthewShow Notes:Matthew Joynes – LinkedIn - https://www.linkedin.com/in/matthewjoynesGamevice - https://gamevice.com LifeMed AI - https://lifemed.ai/ Pulley - https://pulley.com/CompaniesHouse.gov (free UK company filings)👉 Subscribe for more conversations that unleash potential everywhere.🎧 Listen to the audio pod & get extras: https://theparallelentrepreneur.transistor.fm/🚀 Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/

What happens when super-AI makes lawyers, accountants—and even capitalism—obsolete?British-American “apex” parallel entrepreneur Matthew Joynes (PGA producer, GameVice inventor, LifeMed AI founder) joins host Mark Cleveland to smash the china shop of old-school business.In this high-voltage conversation you’ll learn:▸ Why Joynes says the real product of your company is its share price▸ How LifeMed AI replaces 90,000 manual billing jobs with 120 staff and a neural network▸ The fatal cap-table mistakes that make a start-up “un-investable”▸ Post-capitalist realities: one-person, billion-dollar AI companies, robot labor, 7-day weeks disappearing▸ Practical first steps for founders—tokenization, options, warrants, “buying your own time,” and moreChapters:00:00:00 Matthew Joynes Show Teasers00:00:26 Meet Matthew Joynes, “Apex” Parallel Entrepreneur00:02:31 Why AI Will Rewrite History00:09:29 The Fear (And Opportunity) in AI00:12:27 From Blind to Seeing: AI As New Vision00:13:30 Work, Creativity, and Post-Capitalism00:15:54 Parallel Entrepreneurs as Creators00:17:24 What Matthew’s Reading Now00:18:50 Why Every Tech Founder Is Parallel00:22:00 “Your Product Is Your Share Price”00:25:32 Biggest Mistakes in Forming a Company00:29:10 Turning Shares Into Currency00:30:27 Building an Investable Cap Table00:37:52 Competing With (And Eating) Yourself00:38:45 AI As Your Personal Teacher00:44:10 Follow Your Curiosity, Not Just Passion00:49:30 Selling a Film With Just Script & Poster00:52:20 AI Accelerates Every Creative Idea00:56:55 Letting Go, Buying Your Own Time00:57:30 Stop Spending on Others—Invest in Yourself00:59:17 Teaser for Part TwoShow Notes:Share and engage with this interview on LinkedIn: Click hereMatthew Joynes – LinkedIn - https://www.linkedin.com/in/matthewjoynesGamevice - https://gamevice.com Stolen (2012) - http://www.stolen-movie.com/ Bullet (2014) - https://www.youtube.com/watch?v=tdF9Vcv4cCo I Am Soldier (2014) - https://www.youtube.com/watch?v=7LIqnkUl0zA Marmadue (2022) - https://scfilmsinternational.com/current-films-animation-titles/marmaduke-3d/Dragonkeeper (2024) - https://dragonkeepermovie.com/ LifeMed AI - https://lifemed.ai/ Pulley - https://pulley.com/Brendan Iribe - https://brendaniribe.com/ Backbone One - https://playbackbone.com/ Join the Parallel Entrepreneur Network: https://www.parallelentrepreneur.com/

Stop juggling. Start PARALLELING. Entrepreneur, community‑builder and podcast host Mark Cleveland takes the Creative Mornings stage to share why the future belongs to parallel thinkers—people who let multiple passions run side‑by‑side so each fuels the next.Whether you’re a founder with five side projects, an artist‑parent, or a multipotentialite who refuses to “pick a lane,” this 15‑minute talk will give you:• A new definition of success (alignment, not hustle)• Real‑life examples from the Parallel Entrepreneur Network • A 60‑second guided reflection you can do right now • Practical prompts to weave business, art, family and growth into one powerful tapestryChapters:00:00:00 Intro — What “parallel” really means 00:01:55 The origin of The Parallel Entrepreneur project 00:04:17 Case study: Caitlin MacGregor’s aligned life 00:07:08 Insight: The power of slowing down 00:09:40 When stillness feeds creativity 00:11:32 Paralleling vs. Pivoting 00:13:05 Guided reflection exercise 00:14:40 Final invitation + takeaways Join the community:https://ParallelEntrepreneur.com/Subscribe for more talks & founder stories: https://www.youtube.com/@ParallelEntrepreneur?sub_confirmation=1 Key Quotes“Success isn’t in speeding up; it’s in letting every lane of your life feed the others.” “When who you are shows up in everything you do, stress becomes spaciousness.”Connect with Mark• Twitter – https://twitter.com/MarkCleveland • LinkedIn – https://www.linkedin.com/in/mark‑cleveland/ • Podcast – https://parallelentrepreneur.com/podcast Connect with Creative Morningshttps://creativemornings.com/Show Notes:Share and engage with this video on LinkedIn: Click here

Looking for inspiration on juggling multiple business passions? Tim Ozgener might just be your blueprint. He helped take CAO Cigars from a basement startup to a global best-seller and then founded OZ Arts, a cutting-edge contemporary arts hub in Nashville. Now launching Oz Family Cigars, Tim blends art, science, and storytelling into every venture. In this episode, he and Mark Cleveland explore:• Following Your Heart: Why Tim chose cigars and contemporary art• Improv & Entrepreneurship: Leveraging “Yes, And” to handle surprises & spark creativity• Exiting at the Top: Inside the CAO sale, key lessons in valuation & deal structure• Nonprofit vs. For-Profit: Contrasts in building teams, mission, and sustainability• Staying Centered: Yoga, mindful scheduling, and choosing environments that fuel innovationParallel Entrepreneurs, subscribe now and tell us in the comments which Oz insight struck your fancy—was it engineering meets art, or harnessing improv in daily business?Chapters List:00:00:00 Meet Tim Ozgener: Nashville’s Multi-Passionate Unicorn00:01:14 Why Follow Your Passions?00:02:23 The Art & Science of Cigars00:05:09 Improv Skills in Business00:07:14 Launching OZ Arts: A Different Kind of Startup00:09:22 The Power of Authentic Connection00:12:13 Lessons from Dad: Engineering Meets Entrepreneurship00:15:18 Time Management & Team Trust00:19:00 Nonprofit vs. For-Profit: Contrasting Cultures00:22:00 Building Global Distribution00:29:08 The CAO Exit Story00:37:14 Yoga, Flow & Mindful Entrepreneurship00:42:00 Embracing Failure & AuthenticityShow Notes:Share and engage with this interview on LinkedIn: Click hereCAO Cigars - https://www.caocigars.com/ OZ Arts - https://www.ozartsnashville.org/ Crowned Heads Cigars - https://www.crownedheads.com/ Oz Family Cigars - https://ozfamilycigars.com/ The Revenge of the Tipping Point: Overstories, Superspreaders, and the Rise of Social Engineering by Malcolm Gladwell - https://www.amazon.com/Revenge-Tipping-Point-Overstories-Superspreaders/dp/0316575801/ Headway app - https://headwayapp.co/ Art Basel - https://www.artbasel.com/ Ken Cope Consulting, LLC - https://kencopeconsultingllc.com/

AI and security compliance could make or break your next venture. In this episode of The Parallel Entrepreneur, Mark Cleveland sits down with Justin Beals, co-founder of Strike Graph, to dive into frameworks, data risk, and that special systems-thinking spark that turns small wins into scalable success. Leveraging his EdTech expertise to tackle security compliance for billion-dollar enterprises, Justin’s story is a masterclass in spotting trends and executing effectively.Key Highlights:• Opportunity Filtering – The three questions Justin always asks before launching a new product.• AI as Internal Auditor – How Strike Graph deploys large language models to verify compliance automagically.• Co-Founder vs. Solo Act – Winning arguments for teamwork, board partnerships, and the joys of not going it alone.• Music & Mental Health – Surprising ways that daily creative outlets (and old-school Ashtanga yoga) keep Justin’s energy fresh.Ready to sharpen your parallel potential? Subscribe now and share which insight resonated most—AI? Mentoring? Or making that “hundredth monkey” leap?Chapters List:00:00:00 Introduction to Justin Beals and StrikeGraph00:02:02 Spotting Opportunities: Three Key Questions00:04:10 Building Strike Graph: Why Framework Matters00:06:06 Understanding Risk in Entrepreneurship00:08:19 Systems Thinking & Data Models00:12:09 Trends in Cybersecurity and Business Impact00:14:31 Surviving a Downturn: B2B SaaS Realities00:16:18 Co-Founders & Good Investors00:19:43 Leveraging AI in Cybersecurity00:22:35 Mentoring & Measured Learning00:27:25 Creativity and Leadership in Entrepreneurship00:33:13 Lessons Learned in Business and Co-Founding00:40:36 Navigating Change with Venture Backers00:43:19 The Emotional Landscape of Collaboration00:45:18 The Art of Flexibility in Leadership00:46:20 Shifting Focus: From Sales to Strategic Partnerships00:48:00 Scaling with Core Values00:51:38 Identifying Aha Moments in Customer Experience00:53:57 The Impact of AI on Business and Society00:57:52 Empowerment through Creative Technology00:01:05:47 The Future of AI Companions00:01:08:21 Lessons from the Past: Advice for the Future00:01:18:58 The Essence of AI and PoetryShow Notes:Share and engage with this interview on LinkedIn: Click hereSecure Talk podcast - https://www.strikegraph.com/secure-talk-podcastStrikeGraph – https://www.strikegraph.com/ Roundbox Global - https://roundbox.com/Koru - https://www.koru.global/Snow Crash by Neal Stephenson - https://en.wikipedia.org/wiki/Snow_Crash Zealot: The Life and Times of Jesus of Nazareth by Reza Aslan - https://www.amazon.com/ZEALOT-Life-Times-Jesus-Nazareth/dp/140006922X Europe Between the Oceans: 9000 BC – AD 1000 by Barry Cunliffe - https://www.amazon.com/Europe-Between-Oceans-9000-BC-AD/dp/0300170866 The Three Body Problem by Liu Cixin - https://en.wikipedia.org/wiki/The_Three-Body_Problem_(novel) Hundredth Monkey Effect - https://en.wikipedia.org/wiki/Hundredth_monkey_effect

What happens when a merger you can't control threatens to destroy your 22-year business overnight? Meet Robert Hartline—parallel founder who scaled his wireless stores to $100 million, only to face a brutal T-Mobile merger that forced him to shut down half his locations in months. In this candid episode of The Parallel Entrepreneur, Robert reveals why he believes in dancing through chaos, harnessing AI for decisions, and leading from a place of love.Key Highlights:• Secrets of a $100M Scale – How Robert powered up his cell phone stores with EOS and big-picture “why.”• Dark Night of the Merger – The day Google listings vanished, store traffic plummeted, and Robert sold to survive.• Harnessing AI as "Idea Manager" – Why we should treat AI like a creative partner, not a threat.• Mindset & Breathwork – Tools Robert swears by to stay calm, refocus, and unlock “superhero energy.”• The Clark Kent vs. Superman Moment – Overcoming shame, embracing authenticity, and letting your real self shine.If you’re juggling multiple ventures—or dreaming of it—hit Subscribe and share in the comments which breathwork or AI tip resonates most with you!Chapters List:00:00:00 Introduction to Robert Hartline00:00:47 Scaling to $100M & EOS Discipline00:03:01 How Robert Reframes to Discover His “Why”00:08:38 The T-Mobile Merger: From Momentum to Meltdown00:14:20 Darkness, Divorce, and Post-Merger Fallout00:19:45 The COVID Mask Pivot & Parallel Entrepreneurship Gone Wild00:23:49 AI as Your “Idea Manager” 00:27:40 The Energy of Connection and Creation00:30:12 How to Flow: Add Love, Breath & Movement00:32:43 Unique Ability and the Power of Community00:34:56 Discovering Your Why and Core Values00:37:16 The Role of Love in Business and Life00:40:00 Clark Kent vs. Superman: Embracing Your True Self00:42:46 AI as a Decision-Making Tool00:50:07 Energy Management and Personal Practices00:52:17 The Biggest Gift Ever & the Future00:54:56 Slowing Down to Speed Up00:58:15 Wrap-Up & GratitudeShow Notes:Share and engage with this interview on LinkedIn: Click hereThe Decision Experience - https://thedecisionexperience.com/ Entrepreneurial Operating System (EOS) - https://www.eosworldwide.com/ Soma Breath Guided Breathwork Training and Certification- https://www.somabreath.com/ Wim Hoff Breathing - https://www.wimhofmethod.com/breathing-exercises Strategic Coach by Dan Sullivan - https://www.strategiccoach.com/book-a-callTraction: Get a Grip on Your Business by Gino Wickman - https://www.eosworldwide.com/traction-book Driven: Understanding and Harnessing the Genetic Gifts Shared by Entrepreneurs, Navy Seals, Pro Athletes, and Maybe You by Douglas Brackmann and Randy Kelley - https://www.iamdriven.com/ 10x Is Easier Than 2X: How World-Class Entrepreneurs Achieve More by Doing Less by Dan Sullivan and Benjamin Hardy - https://10xeasierbook.com/ The Three Marriages: Reimaging Work, Self and Relationship by David Whyte - https://davidwhyte.com/store/book/the-three-marriages/ Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert - https://www.elizabethgilbert.com/books/big-magic/CallProof, sales tracking app - https://callproof.com/

How do you launch a thriving medical practice, then pivot to a fast-scaling software startup—all while staying laser-focused on patient care, personal growth, and 24 years in recovery? In this episode, Mark Cleveland welcomes Dr. Michael Sprintz, an anesthesiologist-turned-tech-entrepreneur tackling chronic pain, addiction, and complicated billing structures in healthcare. Dr. Sprintz shares how resiliency, authentic leadership, and “flow” guide his parallel ventures.Highlights:• From OR to Revenue Tech – Why Michael traded the surgical suite for software code.• 24 Years Sober – How recovery principles shape his resilience in business.• Nail Compliance, Stop Revenue Bleed – The healthcare billing problem Michael solves.• Mindset Hacks – Handling stress, negativity, and “the shadow self” with unshakable resolve.• Chasing Flow – Moving from “hustle 24/7” to deeper creativity and real presence.Chapters List:00:00:00 The Journey of Dr. Michael Sprintz00:01:45 Resilience and Tenacity in Recovery00:04:27 The Intersection of Pain and Addiction00:06:40 Lessons from Entrepreneurship00:09:00 Aligning Vision and Values00:10:39 The Birth of Solarian00:13:21 Navigating the Software Landscape00:14:08 The Role of AI in Healthcare00:16:13 Market Response and Growth Strategies00:18:14 The Art of Adaptation00:20:07 Authenticity in Business00:22:08 Future Aspirations and Innovations00:24:48 Best Advice Received: What you sell your company is not what you created at first00:28:52 Helping Others See Beyond Their Current Reality00:29:53 Understanding the Opioid Crisis and Healthcare Misalignment00:32:45 Balancing Stress and Personal Life as a CEO00:34:13 Time Management and Effective Communication00:35:56 Lessons from Life and Death Experiences00:37:43 Finding Meaning and Making Ethical Decisions00:39:37 Embracing Technology and Uncertainty in Healthcare00:41:27 Reflecting on Past Accomplishments and Future Risks00:42:55 Living Life with No Regrets00:43:55 The Impact of Literature on Personal Growth00:45:14 The Connection Between Humanity and Business00:52:44 Art, Music, and the Flow of Life00:57:13 Trusting the Process and Letting GoShow Notes:Share and engage with this interview on LinkedIn: Click hereCellarian Inc., healthcare software that improves diagnosis, treatment, documentation and risk-management for substance use disorder and other diseases - https://www.cellarian.com/ A Life of Meaning: Relocating Your Center of Spiritual Gravity by James Hollis - https://jameshollis.net/hollisBooks.html Living with Borrowed Dust: Reflections on Life, Love and Other Grievances by James Hollis - https://jameshollis.net/hollisBooks.html The Alchemist by Paulo Coelho – https://www.amazon.com/Alchemist-Paulo-Coelho/dp/0062315005/ Never Split the Difference: Negotiating As If Your Life Depended on It by Chris Voss – https://www.amazon.com/Never-Split-Difference-Negotiating-Depended/dp/0062407805 Mark’s 2025 Bhavana – https://www.youtube.com/watch?v=twS9UpeqeF0

Wondering how to nurture alignment throughout M&A integration? In this episode John Farkas, founder of Ratio and Candor—two companies that help businesses master M&A integration—discusses how to unlock growth-ready alignment. From creating synergy across different offerings to leading teams through high-stakes transformations, John shares real-world lessons on balancing purpose with performance, leveraging “context switching,” and staying ahead of rapid market shifts.Highlights:• Parallel Mindset – John runs two consultancies that fuel each other.• M&A Mastery – Turning chaotic post-acquisition phases into opportunities for deeper alignment.• Keeping Pace with Change – Simple practices to handle lightning-fast market shifts without burning out.• AI & the Future – How advanced tech is reshaping value propositions—and why you need to adapt now.• Leading with Love – The surprising “sticky note” that guides John’s leadership style.Chapters List:00:00:00 Meet Organizational Alignment Guru John Farkas00:02:08 Taming Chaos: Context Switching Across Industries00:05:17 Birth of Candor: Solving the "Alignment" Dilemma00:07:20 Understanding Organizational Alignment00:09:13 Overcoming Fear & Building Trust in Organizational Change00:11:29 Pace Paradox: Thriving in Accelerating Markets00:13:46 Flattened Org Charts & Shared Objectives00:16:02 The Impact of AI on Business Models00:18:26 Spectacular Failures & Lessons Learned00:20:37 The Mentoring Gap & Real Team Building00:22:52 How do you manage time and energy between ventures00:23:43 Superpowers: Context Switching & Listening00:26:42 Self-Care & the Importance of Loving Leadership00:30:16 M&A and Human Capital: Missing the Biggest Asset00:34:19 Facing an AI-Driven Future00:39:38 Rapid Fire: North Star, Books, Gifts & Wise Words00:43:38 Closing Thoughts: Curiosity, Intent, and LoveShow Notes:Share and engage with this interview on LinkedIn: https://bit.ly/3HDZLsSRatio, a growth marketing consultancy helping B2B healthtech and fintech companies - https://goratio.com/ Candor, a growth architecture firm - https://www.candorgrowth.com/ 99% Invisible podcast - https://99percentinvisible.org/ The Power Broker by Robert Caro - https://99percentinvisible.org/club/ Conclave by Robert Harris - https://www.amazon.com/Conclave-novel-Robert-Harris/dp/1101972904John's "walk on" song - Beautiful Day by U2

Are you a serial entrepreneur juggling multiple ventures and hungry for breakthrough growth? In this candid conversation, Silas Deane reveals his battle-tested blueprint—from bootstrapping a game-changing fintech solution in an unlikely industry to executing a $90M exit without investors. If you’re ready to unlock the secrets of scaling, pivoting, and innovating across diverse markets, this episode is your must-watch playbook.Highlights include:• How Silas bootstrapped VendEngine from idea to digital disruption• An innovative approach to transforming inmate financial transactions• Scaling strategies that grew the business from county jails to 425 facilities• Merging startup agility with corporate synergy at Tyler Technologies• Critical lessons on embracing failure, pivoting, and mastering time management• Leadership insights on integrity, mentorship, and building winning teams• The mindset behind taking calculated risks and seizing future opportunities, including AI trendsChapters:00:01:00 Introduction: Bootstrapping & Exiting with Silas Deane00:02:56 VendEngine's Genesis: Innovating Inmate Transactions00:04:32 Transforming the Inmate Payment System00:07:27 Scaling Success: From County Jails to 425 Facilities00:11:13 Corporate Synergy & Strategic Growth: Acquisitions & Hardware Innovation00:16:09 Finding Synergies and Growth Opportunities00:17:14 Learning Through Failure: Time Management & the Power of Pivoting00:21:32 Leadership in Action: Integrity, Mentorship & Government Insights00:24:46 Overcoming Financial Hurdles: Hustling to a $90M Exit00:29:09 The Journey of a Parallel Entrepreneur00:32:21 Learning from Mistakes and the Freedom of a Clean Slate00:34:29 Feeding the Creative Drive00:36:26 The Power of Historical Insights and Identifying Patterns00:39:08 The Importance of Business Basics00:40:19 Discovering and Nurturing Talent00:41:45 Turning Mistakes into Learning Opportunities00:46:25 Advice to My Younger Self00:48:14 The Nature of Risk in Entrepreneurship00:50:18 The Value of a Large Addressable MarketShow Notes:Share and engage with this interview on LinkedIn: https://bit.ly/4l4RZH8VendEngine Inc. - https://www.businesswire.com/news/home/20210901005799/en/Tyler Technologies (NYSE:TYL) - https://www.tylertech.com/ KPMG - https://kpmg.com/us/en.html Deane/Smith & Partners, a Nashville-based, award-winning public relations, marketing and advertising agency - https://deanesmith.agency/ NIC transaction management solution - https://www.florida.egov.com/services.html University of Kentucky, Gatton College of Business and Economics, Von Allmen Center for Entrepreneurship - https://vace.uky.edu/node and https://vace.uky.edu/bootcamp/mentors/silas-deaneJunior Achievement of Middle Tennessee, a nonprofit that inspires and prepares young people for success - https://jausa.ja.org/indexThe Power of Broke: How Empty Pockets, a Tight Budget, and a Hunger for Success Can Become Your Greatest Competitive Advantage by Daymond John - https://daymondjohn.com/pages/power-of-broke

Unlock the secrets of building an acquisition empire from someone who's done it well. In this exclusive interview, John Cerasuolo, CEO of Leap Partners, reveals the unconventional strategies and hard-won lessons that propelled his journey from the Naval Academy to leading a thriving home services network. If you're a parallel entrepreneur looking to scale or dreaming of launching your own network, this conversation is your blueprint for success.Highlights include:• His transformative journey from the Naval Academy to leading a multipreneur empire• How Leap Partners was born out of a shared vision and 45+ acquisition successes• Proven strategies for identifying quality businesses and integrating diverse cultures• Lessons learned from early exits and the importance of “begin with the end in mind”• The secret to balancing rapid growth, due diligence, and celebrating success• Insights on building a people-first, family-centric company culture• Rapid-fire insights on must-read books and what fuels his day-to-day driveWhether you're running multiple businesses or planning your next big leap, this conversation is packed with actionable wisdom for every ambitious entrepreneur.Chapters List:00:01:00 Introduction to John Cerasuolo and Leap Partners00:02:06 Naval Academy: Forging a Leader00:04:09 Leap Partners Genesis: From ADS Security to Home Services00:08:31 Identifying Acquisition Opportunities00:11:05 Integrating Cultures in Acquisitions00:14:36 Exiting with Great M&A Advisors00:18:17 Challenges in Due Diligence00:20:07 Celebrating Success00:23:03 Mindfulness and Daily Practices00:24:18 Advice to His Younger Self00:26:08 Learning from Each Other in Business00:27:15 Navigating Talent Challenges in the Trades00:29:21 Rapid Fire Insights00:32:20 Recognition and Awards00:33:03 Scaling a Culture of Happiness00:34:20 Modeling Leadership Behavior00:35:22 A Day in the Life of a CEO00:36:48 Choosing the Right Financial Partners00:38:09 Surrounding Yourself with Talent00:39:22 Books that Inspire00:40:21 Closing Thoughts on Life and BusinessShow Notes:Share and engage with this interview on LinkedIn: https://bit.ly/3HUWntGLeap Partners, a Family of Service Companies - https://www.theleappartners.com/ Fossil Future by Alex Epstein - https://www.forbes.com/sites/johntamny/2022/09/29/book-review-alex-epsteins-excellent-and-essential-fossil-future/ Atlas Shrugged by Ayn Rand - https://aynrand.org/novels/atlas-shrugged/ Joe Scarlett, former President and Chairman of Tractor Supply Company - https://joescarlett.com/

Ready to discover how to hire for potential rather than past credentials—and why it could transform your business? In this episode of Parallel Entrepreneur, Mark Cleveland sits down with Caitlin MacGregor, CEO and Co-Founder of Plum, to talk about building a high-growth company while raising a family and defying the usual startup playbook. If you’re juggling multiple ventures—or planning to—Caitlin’s journey will inspire you to embrace change, experiment with collaboration, and double down on what really drives success.Highlights:• Power Couple: Why being married to her co-founder is Caitlin’s superpower (despite investor skepticism).• 13 Years of Growth: Balancing fundraising with customer-driven revenue, and why sales might matter more than venture capital.• People Over Résumés: How Plum’s behavioral data approach uncovers “diamonds in the rough” for any role.• Authentic Leadership: Leading with love, care, and collaboration to break down silos and foster real engagement.• GenAI & the Future: Why tasks, not jobs, are being automated—and how to reinvent your organization for exponential success.Don’t miss these candid insights from a founder who’s rewriting the rules on entrepreneurship and talent strategy.Chapters List:00:00:56 Meet Caitlin MacGregor: Founder, CEO & Human Potential Champion00:02:44 When Your Co-Founder Is Your Spouse00:05:08 Growing a Family & a Company Simultaneously00:09:21 Fundraising Lessons: 99 No’s for 1 Yes00:15:17 Rethinking Growth in a Shifting Market00:17:30 Why Sales Might Matter More Than Fundraising00:20:48 Integrating Feminine Dimensions of Leadership00:25:16 Symbiotic Health - the New Model for Business Success00:26:51 Well-being, Mindfulness & Self-Awareness00:31:06 The Science of Unlocking Human Potential00:35:00 Hire for Behaviors, Not Resumes00:35:57 The Collaborative Operating System: Eliminating Silos00:38:48 Perfection vs Collaborative Creation00:45:42 Transforming Company Culture to Eliminate Politics00:48:00 A Hiring Experiment That Sparked Plum00:52:18 Advice for Future Generations00:57:07 GenAI & the Future of Work00:59:55 Books, Escapes & Art01:04:53 The Future of Change ManagementShow Notes:Share and engage with this interview on LinkedIn: https://bit.ly/3FKdXQFPlum, a revolutionary talent platform - https://www.plum.io/ EY Entrepreneurial Winning Women - https://www.ey.com/en_us/entrepreneurial-winning-women-north-america/class-of-2024 Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies by Reid Hoffman - https://www.blitzscaling.com/Bo Burlingham - https://boburlingham.com/The Revenue Engine: Fueling a B2B High Octane Pipeline by Kara Smith Brown - https://therevenueengine.com/The Fourth Wing by Rebecca Yarros - https://rebeccayarros.com/fourthwingAbout Plum:Dive into a fresh take on talent strategy with Plum, the durable skills company. Our robust talent assessment platform, PlumThrive, helps you harness the lasting impact of the core competencies that matter. By focusing on durable skills, we transform your company into a skills-based powerhouse, allowing you to make better talent decisions across the employee journey.Are you ready to boost your hiring precision and extend employee tenure? Explore PlumThrive and transform your workforce strategy today: https://www.plum.io/book-demo

Get ready for a masterclass in multi-venture entrepreneurship from Christian Paro, founder of Center 615, Studio 615, Five Points Alley Shops—three of the most dynamic co-working and creative spaces in Nashville—and a new 49-acre trail-oriented development, featuring artist lofts. Hosted by Mark Cleveland, this episode of Parallel Entrepreneur explores how Christian turned a park-management background into a cutting-edge real estate empire that thrives on community, collaboration, and creativity.What You’ll Learn:• Banker Skepticism → Big Vision: How Christian overcame early financing doubts to build Nashville’s go-to coworking hub.• The Power of Celebration: Why throwing parties and embracing small wins keeps your team and tenants inspired.• Mindful Pauses & Ping Pong: Christian’s secret to staying calm under pressure (including his favorite “reset” technique).• Mentoring vs. Micromanaging: How giving autonomy attracts long-term staff and nurtures a vibrant entrepreneurial ecosystem.• Expanding Into Events & Arts: From a single building to 49 acres of innovation—Christian’s massive new development plan.Chapters List:00:00:00 Meet Christian Paro: The Man Behind Nashville's Most Innovative Collaboration Spaces00:01:28 From NYU Parks & Rec to Property Investor00:03:06 Discovering Coworking: The Birth of Center 61500:05:19 Banking Skepticism & the Power of Relationships00:08:29 Studio 615: Expanding into Creative Production Spaces00:12:05 Patterns, Parties & Parallel Lessons00:13:48 Biggest Lessons & Avoiding Over-Leverage00:14:54 Mentoring, Not Micromanaging00:16:32 Mindfulness Practices & the Entrepreneurial Journey00:22:13 Designing a New 49-Acre Community00:24:13 Mindful Pauses: Staying Centered Under Pressure00:27:25 Rapid Fire Insights: Gifts, Mantras, Books & Jedi Wisdom00:32:36 Do What Scares You00:37:12 Facing Fears & Final ThoughtsShow Notes:Share and engage with this interview on LinkedIn: Click hereC615, a driving force in building and shaping community in Nashville - https://c615.co/Artist Sergey Gordienko (the art behind Mark) - https://www.instagram.com/dowhatyoulove.artist/Joanna Barbera, Nashville Musician and Mindfulness Mentor - https://www.joannabarbera.com/8 Decisions (Conscious Entrepreneur Tribe) by Robert Hartline - https://8decisions.com/Nasty Girl by Iglesias - https://open.spotify.com/track/5MghBTWUogtorQqmKBwaBnAll about Love: New Visions by Bell Hooks - https://www.amazon.com/All-About-Love-New-Visions/dp/0060959479The Optimist by Sophie Kipner – https://www.amazon.com/Optimist-Sophie-Kipner-author/dp/1783525584 The Madness of Crowds: A Novel by Louise Penny - https://www.gamacheseries.com/books/the-madness-of-crowds/Do One Thing Every Day That Scares You: A Journal - https://www.amazon.com/One-Thing-Every-That-Scares/dp/0385345771“Jenny’s Answer (867-5309)” female empowerment parody song by Jenny Pruitt - https://www.youtube.com/watch?v=qi2Ru6vvZo0Tiny Happy Things: Poems by Jenny Pruitt - https://www.amazon.com/Tiny-Happy-Things-Jenny-Pruitt/dp/B0DLD78L24

Ready to master the art of running multiple ventures without losing your sanity—or your shirt? Join host Mark Cleveland and Craig Fuller, the pioneering founder of FreightWaves, as they rip open the playbook on “Parallel Entrepreneurship.” From launching data-driven freight tech to buying iconic media brands—and even building an aviation empire—Craig spills the secrets behind owning your audience, harnessing AI for growth, and seizing opportunities most people miss. If you’re tired of thinking small and ready to multiply your wins, this episode is your ultimate roadmap.What You’ll Learn:• How to leverage distribution (and why it’s everything)• Turning media audiences into profit engines• When boredom is more dangerous than burnout• Using AI to supercharge content creation and customer engagement• The power of small, strategic M&A deals for explosive growthHit play and discover how to “Focus Less, Explore More” so you can scale your impact across industries—on your own terms.Timestamps:00:00:51 Introduction to Craig Fuller and FreightWaves00:01:50 Revolutionizing Transportation with Data00:03:40 The Business Model of FreightWaves00:05:12 From Futures to Transparency in Trucking00:06:46 The Bloomberg Inspiration for FreightWaves00:11:56 Pursuing Opportunities to Drive Top of Funnel00:18:45 Motivating Teams and Sharing Value00:21:20 Finding Inspiration and Avoiding Burnout00:26:29 Current Trends in the Transportation Market00:34:04 Harnessing AI for Enhanced Content Creation00:39:58 AI's Role in Customer Engagement00:41:54 Evaluating Business Opportunities00:42:56 The Importance of Distribution in Business00:47:22 Asymmetric Risk and Business Strategy00:50:10 Learning from Experience and Testing00:56:58 The Journey vs. Destination in Entrepreneurship01:02:37 The Value of Shared Experiences in BusinessShow notes: Share and engage with this interview on LinkedIn: Click hereBloomberg by Bloomberg - https://www.bloombergbybloomberg.com/The Power Law: Venture Capital and the Making of the New Future - https://www.amazon.com/Power-Law-Venture-Capital-Making/dp/052555999XRange: Why Generalists Triumph in a Specialized World by David Epstein - https://davidepstein.com/range/The Rational Optimist: How Prosperity Evolved by Matt Ridley - https://www.amazon.com/Rational-Optimist-Prosperity-Evolves-P-s/dp/0061452068Outliers: The Story of Success by Malcolm Gladwell - https://www.amazon.com/Outliers-Story-Success-Malcolm-Gladwell/dp/0316017930

How do you juggle multiple ventures and keep your cool under pressure? Meet Nitin Rai — seasoned founder, investor in 70+ startups, and champion of underrepresented talent. In this eye-opening episode, host Mark Cleveland uncovers Nitin’s secrets to mastering delegation, cultivating mindful leadership, and building “small” ideas into life-changing success stories. Discover why he believes failure is not an option, why women-led startups excel, and how a single headstand (yes, you read that right!) can sharpen entrepreneurial intuition.If you’re a Parallel Entrepreneur hungry for both impact and inner balance, this conversation is your roadmap to thriving in the fast-paced world of multi-venture leadership.In this conversation, we dive into:• How openness and authenticity drive healthier board relationships and better decision-making• Why failure isn’t an option for many minority entrepreneurs• Why relinquishing control is essential for founders who juggle multiple ventures—and how to do it effectively• Why women-led ventures often outperform expectations and attract strong investor support• What’s happening outside of Silicon Valley in today’s startup worldTime Stamps:00:00:26 Introduction to Nitin Rai and His Journey00:05:42 The Importance of Transparency, Leading from the Heart00:08:49 Challenges in Raising Capital: The Current Landscape00:14:43 Balancing Multiple Ventures: The Art of Delegation00:18:05 Navigating Exits: Lessons Learned00:19:40 Sharing Wealth: The Entrepreneurial Approach00:22:01 Role Models and Mentorship: Influences on Nitin's Approach00:24:45 Identifying with Entrepreneurs: A Personal Connection00:25:40 The Power of Small Ideas00:25:56 The Power of Intuition00:27:16 Mindfulness Practices and Self-Care00:29:51 Celebrating Entrepreneurial Success00:32:12 The Virtuous Cycle of Wealth Creation00:34:28 Entrepreneurship as an Art00:35:23 Defining Success in Entrepreneurship00:38:24 The US Entrepreneurial Landscape00:41:01 Advice to Your Younger Self00:42:14 Reading and Continuous LearningShow notes:Share and engage with this interview on LinkedIn: https://bit.ly/43UJPKmKishau Rogers, Founder of Time Study - https://kishau.com/about/Ania Rodriguez, Founder of JourneyTrack - https://www.journeytrack.io/aboutAllie Magyar, Founder of Hubb - https://www.linkedin.com/company/hubb/Monica Enand, Founder of Zapproved - https://zapproved.com/about-us/company/Nat Parker, Founder of Globe Sherpa (changed to Moovel North America) - http://moovelus.com/Ganesh Shankar, Entrepreneur & Investor - https://www.responsive.io/about/"Anarchy" by William Dalrymple - https://www.amazon.co.za/Anarchy-Company-Corporate-Violence-Pillage/dp/1635573955White Mughals by William Dalrymple - https://www.amazon.com/White-Mughals-Betrayal-Eighteenth-Century-India/dp/014200412XLight on Life by B.K.S. Iyengar - https://www.amazon.com/Light-Life-Journey-Wholeness-Ultimate/dp/1594865248

How do you scale, sell, and still come back for more? Meet Roger Brown — a serial founder who’s built (and exited) four different ventures, from physician services to cannabis testing labs. In this power-packed interview, Roger reveals how to create genuine value in a business (not just revenue), the art of spotting the right time to sell, and why trusting your team is your ultimate superpower. He also dishes on where AI fits in modern marketing, the pitfalls of overvaluing your own company, and how a simple dose of salt water therapy can recharge an overworked mind.Whether you’re juggling multiple startups or dreaming of your first exit, Roger’s candid insights are a must-watch for any Parallel Entrepreneur.Tune in to gain insights from a leader who believes in doing the right thing, embracing change, and leaving a lasting legacy.Chapters:00:00:00 Introduction to Parallel Entrepreneurship00:00:24 Roger Brown's Journey into Cannabis Testing00:01:18 The Thrill of Building Businesses00:04:13 Creating Value in Business00:05:25 Challenges in the Healthcare Industry00:06:30 The Debate: Symptoms vs. Wellness00:08:27 The Role of Co-Founders in Business00:11:27 Insights from M&A Advisors00:14:56 Lessons Learned from Selling Businesses00:17:59 Navigating Healthcare's Evolution00:20:22 AI's Role in Modern Business00:23:14 Finding Balance and Recharging00:24:44 Guiding Principles and Life Lessons00:28:13 Learning from Mistakes00:30:42 Legacy and Life's Purpose00:31:53 Rapid Fire Questions00:32:59 The Importance of Trust and Team Dynamics00:36:44 Embracing Change and PerspectiveShow Notes:Share and engage with this interview on LinkedIn: https://bit.ly/43EixZQ

’m joined by Jason Putnam, a two-time award-winning executive (Globee Executive of the Year, Silver Stevie Award) and a 2024 Inspiring Leader. Jason’s the Chief Revenue Officer at Plum, where he’s revolutionizing the talent space with psychometric data to build inclusive, thriving teams.In this conversation, we dive into: - Why “failing fast” can spark rapid innovation - How psychometric data transforms hiring and retention - Cultivating a culture that scales alongside your business - Personal insights on mindfulness, leadership, and building strong teamsDon’t miss Jason’s fascinating journey and powerful takeaways—perfect for any parallel entrepreneur aiming to juggle multiple ventures with clarity and impact.Chapters:00:00:00 Welcome to the Parallel entrepreneur00:00:29 Introduction to Jason Putnam and Plum00:04:52 Scaling Businesses with Plum's Tools00:10:50 Addressing Unconscious Bias in Recruitment00:14:08 How AI is Transforming the Hiring Game00:17:32 Understanding the Pace Paradox of Change00:21:07 Navigating Rapid Change with a ‘People-First’ Approach00:27:45 The Impact of AI in Our Lives00:33:32 Lessons from Exits: Building for Success00:36:56 How Fast Decisions Spark Innovation00:39:46 Fail Fast, Learn Faster: The Entrepreneurial Spirit00:44:15 How Jason Finds Mindfulness by Helping Others00:45:16 Books Jason is currently reading Show notes:Share and engage with this interview on LinkedIn: https://bit.ly/3FMMaPAPlum - https://www.plum.io/Caitlin MacGregor (Founder and visionary behind Plum) - https://www.plum.io/aboutMove Fast, Break Shit, and Burn Out by Dr. Tracey Lovejoy and Shannon Lucas - https://www.amazon.com/Move-Fast-Break-Shit-Burn/dp/1544515774The Talent Fix by Tim Sackett - https://www.amazon.com/Talent-Fix-Tim-Sackett/dp/1586445227Scythe by Neal Shusterman - https://www.amazon.com/Scythe-Arc-Neal-Shusterman/dp/1543617948Spartan Up by Joe DeSena - https://www.amazon.com/Spartan-Take-No-Prisoners-Overcoming-Obstacles-Performance/dp/0544286170

In this engaging conversation, Mark Cleveland and Francisco Gonzalez explore the essence of entrepreneurship, focusing on the importance of community, mentorship, and the entrepreneurial mindset. Francisco shares his journey from early entrepreneurial experiences to founding Fearless Journeys, a community aimed at connecting aspiring entrepreneurs. They discuss the emotional aspects of entrepreneurship, the significance of listening to customers, and the role of fear in decision-making. The conversation also touches on the importance of spirituality, mindfulness, and the impact of books on personal growth. Throughout, they emphasize the value of relationships and the need for an adventurous spirit in the entrepreneurial journey.Chapters:00:00:00 Introduction to The Parallel Entrepreneur Podcast00:00:28 Introduction to Fearless Journeys and Francisco Gonzalez00:02:47 The Early Entrepreneurial Spirit00:03:42 Inception of Fearless Journeys00:06:49 Building a Community of Innovators00:09:54 Insights from Entrepreneurial Conversations00:11:47 The Value of Travel and Connection00:12:40 Role Models and Mentorship in Entrepreneurship00:13:25 The Importance of Timing in Business Exits00:14:31 The Pragmatic Optimist: Navigating Business Valuation00:15:44 Identity and the Entrepreneur: Letting Go of Attachment00:16:06 Parallel Entrepreneurship: Balancing Multiple Ventures00:17:32 The Emotional Toll of Exiting a Business00:19:16 Fear and Risk: Embracing the Unknown00:23:35 Mindfulness and Spirituality: Grounding in Faith00:24:53 Podcasts and Personal Growth: The Power of Listening00:25:05 Books that Inspire: Lessons from 'The Alchemist' and 'Atomic Habits'00:29:36 The Value of a Gap Year00:32:59 Essential Skills for Parallel Entrepreneurs00:33:51 Defining Your North Star00:34:54 The Importance of Lifelong Learning00:35:39 Embracing Adventure in Entrepreneurship00:37:05 Finding Joy in Entrepreneurship00:38:22 Delegation and Efficiency in Business00:39:51 Building an Entrepreneurial MindsetShow notes:Share and engage with this interview on LinkedIn: https://bit.ly/3HSmpOdFearless Journeys Website: fearlessjourneys.orgAgents of Innovation Podcast - https://agentsofinnovation.org/Economic Club of Miami - https://www.econclubmiami.org/The Heart of the American Dream by Francisco Gonzalez - https://www.amazon.co.za/dp/B0DNMHVGXBThe American Dream is a Terrible Thing to Waste by Francisco Gonzalez - https://www.amazon.com/American-Dream-Terrible-Thing-Waste/dp/B0BRDCCNHMThe Alchemist by Paulo Coelho - https://paulocoelhoblog.com/Atomic Habits by James Clear - https://jamesclear.com/

How do you build a company that buyers can’t wait to acquire—and still keep your entrepreneurial spark alive? In this episode of The Parallel Entrepreneur, we sit down with John McDonald, Co-Founder and Senior Managing Director of Kensington Park Capital, who’s closed 300+ M&A transactions. John shares:Highlights:• The biggest mistakes founders make when selling• How to spot the perfect buyer (it’s not just about price!)• The HVAC & Home Services roll-up wave: Who’s buying and why• Tactical exit-prep moves that boost your valuation• The “buy side” strategy—growing your biz by acquiring rivalsWhether you’re a serial founder eyeing your next sale or a trailblazer itching to acquire, John’s insights will help you maximize value, protect your team, and maintain the creativity that powers your parallel ventures. Don’t miss these real-world lessons from one of the industry’s most seasoned M&A advisors!Chapters:00:00:00 Introduction to the Parallel Entrepreneur00:00:36 About Kensington Park Capital00:03:02 Entrepreneurial Mindset: Diversifying Through Necessity or Passion00:06:06 HVAC Roll-Ups: Innovation in Customer Acquisition and Service00:10:17 Choosing the Right Buyer: Exit Strategies and Integration00:12:36 Lessons Learned from 300+ Transactions in Investment Banking00:17:06 Decision-Making Frameworks for Entrepreneurs and Advisors00:20:46 Timing the Sale: Entrepreneur Advice on Business Preparation00:22:29 Keys to a Successful Business Sale00:25:51 Private Equity and Buy-Side Acquisitions Explained00:30:13 First-Time vs. Second-Time Entrepreneurs: Patterns in Growth00:36:21 Overcoming Imposter Syndrome and Embracing Positivity00:39:00 Controlling Your Mindset: The Power of Optimism in Entrepreneurship00:43:10 Finding the Perfect Fit: Leveraging Business Relationships00:45:53 Innovation and AI in Mergers & Acquisitions00:48:10 A Unique Business Sale Story: Lessons in Collaboration00:51:11 The Value of Patience in Complex M&A Transactions00:52:56 Celebrating Success: Gratitude and Giving Back in BusinessShow Notes: Share and engage with this interview on LinkedIn: Click hereLearn more about Kensington Park Capital - https://kensingtonpark.com/John is currently reading "You Like It Darker" by Stephen King - https://stephenking.com/works/collection/you-like-it-darker.html

Join me, Mark Cleveland, as I sit down with Ania Rodriguez, CEO & Founder of JourneyTrack.io, to discuss her journey as a serial entrepreneur and her mission to revolutionize customer experience. Ania shares her insights on building enterprise-grade SaaS platforms, raising capital as a female founder, and scaling multiple businesses simultaneously. Highlights:• How Ania leveraged her background in customer experience and innovation to launch JourneyTrack.• The importance of listening to your customers and tying Customer Experience to ROI.• Her strategies for building a winning team and thriving as a Parallel Entrepreneur.• If you're an entrepreneur, leader, or innovator, this episode is packed with actionable advice and inspiration.Chapters:00:00:00 Welcome to the Parallel Entrepreneur00:29:00 Introduction to Anya Rodriguez and JourneyTrack.io00:02:12 The Importance of Customer Experience00:06:04 Lessons from Entrepreneurship00:08:37 Scaling and Team Dynamics00:09:50 Mentorship and Networking00:13:20 Navigating Capital Raising Challenges00:15:27 Daily Life as a CEO00:16:31 Finding Inspiration and Energy00:18:34 Finding Investors and Building a Supportive Team00:22:23 Defining the North Star for Impact00:26:30 The Role of AI in Customer Experience00:29:39 Embracing Experimentation and Agility00:31:32 Lessons on Timing and Exit Strategies00:33:57 Advice to My Younger Self00:37:06 The Power of Creativity and MentorshipShow Notes:Share and engage with this interview on LinkedIn: https://bit.ly/4l6NDzeThe Gap and The Gain by Dan Sullivan - https://gapandgainbook.com/Life Force by Tony Robbins - https://tr.tonyrobbins.com/life-force

In my very first episode, I sit down with visionary Parallel Entrepreneur, William Klehm, to unpack the lessons he learned from building, scaling, and selling multiple businesses. From spinning off a $28 billion asset at Ford Motor Company to leading groundbreaking startups in e-bikes and artificial intelligence, Bill shares his journey of innovation, leadership, and impact. Chapters:00:00:00 Welcome to the Parallel Entrepreneur01:18:00 Lessons from Ford: The Foundation of Entrepreneurship04:05:00 Lessons from Bill's father, the inventor of the CD-ROM07:43:00 The Startup Journey: From Concept to Capital18:20:00 Key Lessons in Entrepreneurship24:06:00 How he disrupted the automotive and cycling industries33:11:00 Customer-Centric Leadership34:57:00 The Impact of AI on Business36:17:00 AI in Education and Beyond38:55:00 Lessons from Mergers and Acquisitions43:06:00 Defining Your North Star44:27:00 Bill's current goals for life48:54:00 The Power of Boldness50:51:00 Trusting Your Instincts51:28:00 The Journey of EntrepreneurshipThis candid and inspiring conversation explores themes of courage, resilience, and the drive to make a lasting impact. Whether you're an aspiring entrepreneur or a seasoned business leader, there's something here for everyone. Show Notes:Share and engage with this interview on LinkedIn: https://bit.ly/3HyElO5

The Parallel Entrepreneur Podcast, hosted by Mark Cleveland, dives into the journeys, challenges, and insights of entrepreneurs who simultaneously manage multiple ventures. Through candid conversations, we uncover what drives these visionaries to juggle diverse enterprises, how they navigate risks and failures, and the lessons that have shaped their paths. Guests share practical advice on scaling businesses without losing their edge, balancing energy and focus across ventures, and finding inspiration in mentors and personal philosophies.From reflections on pivotal moments like company exits to insights on living authentically and defining success, each episode offers listeners an opportunity to connect with the stories, strategies, and wisdom of trailblazers in parallel entrepreneurship.