Entrepreneur Conundrum

In this solo episode, Virginia Purnell breaks down the domino effect: how one date or booking can trigger everything downstream in your business, so the work stops running through you for every little step. She uses her friend Mary's photography business and her own podcast production to show what it looks like when one input sets off the whole chain.   Key Discussion Themes: - The one thing every...

Michael Uadiale is a serial entrepreneur, practicing CPA, and the founder of SMEED CPA, where he helps business owners use the tax code as a tool to build real wealth and reach financial freedom faster.   Key Discussion Themes: - Why most business owners spend 13 to 18 years in "tax jail" — and how to get out - The tax code as a roadmap: how the government uses taxes to incentivize behavior - What...

Lee Smith is a UK-based, values-driven M&A operator with over 25 years of experience buying, fixing, and scaling businesses, and the founder of Verdani Capital. He's acquired 26 companies and now focuses on buy-and-build growth, ethical deal-making, and leading without ego.   Key Discussion Themes: - Why the leap from a small business to a large one is psychological, not financial - Buy-and-build...

Lisa Woodruff is the founder and CEO of Organize 365 and host of the Organize 365 podcast (24M+ downloads). A former teacher with a PhD in applied psychology, she's the author of six books, including her newest release, Escaping Quicksand. Key Discussion Themes Why cleaning up isn't the same as organizing — and what "Swiss cheese organizing" quietly costs you The declutter → organize → productivit...

James Rose is the founder and CEO of Inflective Group, a media and communications group built by acquiring minority equity stakes in profitable marketing agencies. He has spent over 20 years building and scaling companies across startups, tech, and private equity. Key Discussion Themes - Scaling a service business through M&A without losing what makes it work - Why a people-first culture beats a c...

Guest Introduction Greg Workmon is the founder and CEO of LoadUp, a tech-enabled junk removal marketplace transforming the industry with transparent pricing, operational efficiency, and innovation-driven growth. Key Discussion Themes How LoadUp started with one repeatable service: mattress removal Why transparent online pricing changes the customer experience The decision to skip franchising—and w...

Guest Introduction Bill Crawley is the Founder and CEO of Advark AI. He’s been an entrepreneur since childhood, has built and sold multiple companies, and now focuses on helping small business owners market with clarity—without needing to become marketers themselves. Key Discussion Themes Why marketing feels like “who can spend the most on Google” (and what to do about it) How Advark AI guides own...

Guest Introduction Rich Kahn is a digital marketing veteran and serial entrepreneur, co-founder and CEO of eZanga and Anura. He’s spent 30+ years in digital advertising and built Anura after discovering fraud was damaging traffic quality inside his own ad network. Key Discussion Themes How Rich went from early internet projects to building ad tech companies What ad fraud is — and why it’s not just...

  Jim Beach is an entrepreneurship educator, author, and radio host. He hosts School for Startups Radio and teaches founders how to build practical, profitable businesses without hype, shortcuts, or unnecessary risk. Key Discussion Themes Getting fired—and using it as a starting line instead of a dead end Why Jim teaches entrepreneurship without creativity, big risk, or “passion-first” thinking Th...

Lori Atwood is the founder and CEO of Fearless Finance, a fiduciary financial planning firm offering hourly advice without sales pressure, minimums, or judgment. With 25+ years in finance (including investment banking, asset management, and private equity), Lori founded Fearless Finance to change how people access financial guidance—especially during the messy middle of life and business growth. K...

Nate Amidon is the founder and CEO of Form 100 Consulting, a veteran-owned technology consulting firm focused on transforming software development organizations using military leadership and mission execution principles. Key Discussion Themes Why “command and control” is a myth—and what high-performing teams actually need How alignment breaks down between business priorities and engineering execut...

Avrohom Jacks is a serial entrepreneur, coach, and bestselling author who helps founders scale their businesses “like crazy without going crazy.” He’s also a former rabbi and currently COO of an AI legal tech company, bringing a rare mix of clarity, storytelling, and strategy. Key Discussion Themes Why the founder’s mindset is the business’s greatest asset How Avrohom gets in front of clients (and...

Michi McClure is the founder of Consivian, where she helps leaders and organizations bridge the gap between compliance and culture through leadership development, coaching, and operational strategy. With a law background and decades of experience advising startups, medical groups, and corporations, she brings a steady, practical framework rooted in integrity and accountability. Key discussion them...

Guest Introduction Steff Vanhaverbeke is a veteran business coach and change facilitator helping leaders become irreplaceable in the age of AI. With a background in early web development and 20+ years guiding organizations through change, she focuses on keeping work human while teams adopt powerful new technology. Key Discussion Themes Why most people think they need prompt training—and what actua...

Guest Introduction John Whitt is a corporate leader turned business coach and the founder of Business Whitt. After decades in the corporate grind, he built Whole Life Leadership to help entrepreneurs and executives grow businesses without losing their lives in the process. Key Discussion Themes The shift from corporate life to entrepreneurship — and why many people bring the “grind” with them Who...

Guest Mary Lawson — Mary Colleen Photography Mary is a fine art trained photographer based in Valleyview, Alberta. She specializes in school, sports, and event photography, with a growing photo booth offering for events and business marketing. Key discussion themes Building community trust first, then expanding services (grad photos → school photos → more communities) Getting clients the unglamoro...

Guest Introduction Laura Patac returns to Entrepreneur Conundrum to talk about her newest book, Whole, Not Perfect , and how imperfection, reflection, and authenticity shape the way we live and lead—especially during major identity shifts. Key Discussion Themes Identity crisis after leaving a role, title, or organization The “unique individual value proposition” (4-part framework): Origin story St...

Episode Link https://entrepreneurconundrum.com/derrickgirard Guest Derrick Girard is a former Air Force veteran, tech founder, and author. After years in the financial services industry, he built a tech company to solve an industry-wide problem—then sold it six and a half years later. Today he speaks and consults with entrepreneurs and organizations on applying the Figure It Out mindset to real-wo...

In this episode, Virginia sits down with serial entrepreneur and author Italia Tornabene to talk about: How survival shaped Italia’s first real entrepreneurial moves Building timeless brands across beauty, wine, and education Who her ideal clients are for Bene Bellezza, Tornabene Wine, and Baxter Learns to Save Why entrepreneurs should show up on every relevant platform The unexpected power of Lin...

Guest: Erin Krueger Host: Virginia Purnell Websites: Capture the Culture – https://capture-the-culture.com/ https://erinkrueger.com What We Covered: Walking away from a corporate job over ethics Building a real estate team from scratch in a city where she knew only five people Forecast-based hiring vs. hiring when overwhelmed Why culture matters more than skill The layered interview system that en...

Episode Guest: Rob Haynie Company: Life Insurance Settlements Association member / LI Settlements Website: lisettlements.com LinkedIn: Rob Haynie (linkedin.com/in/rob-haynie-08656b9/) Podcast Mentioned: Unlocking the Hidden Value of Your Life Insurance What you’ll learn What a life settlement is (and how it differs from surrendering or lapsing a policy) Why policies often get more expensive later,...

In this episode, Virginia talks with Logan Lyles about: Logan’s path from journalism (2008) to B2B tech sales, then podcasting and demand gen Why webinars still work—when you treat them like a conversion system, not a one-off event Logan’s best-fit clients: B2B (especially agencies, professional services, SaaS) Client acquisition on LinkedIn “Starting a new position” post + profile optimization Re...

In this episode, we cover: How Charmaine turned her own search for worth into a life of service Who she serves—and why purpose doesn’t have an age, role, or title Why confidence and finances are common roadblocks for mission-driven entrepreneurs Letting go of perfection and choosing authenticity instead Faith, consistency, and perseverance when building something meaningful Why your win doesn’t ha...

In this episode of Entrepreneur Conundrum , Virginia Purnell sits down with Alison Mullins — an award-winning sales leader, two-time best-selling author, and founder of Rep Methods — to talk about what actually drives growth in trade-based businesses. Alison shares why public speaking, trade shows, and real conversations consistently outperform social media in her industry — and how too many sales...

In this episode, we cover: Why entrepreneurship is harder than most people expect The hidden cost of “doing nothing” in business How AI agents are transforming marketing automation Why live webinars are making a comeback The importance of authenticity in an AI-driven world How to protect your mindset during brutal business seasons Why patience is not optional for long-term success What real scalab...