Risk & Resolve

Conner Insurance
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  • ENTREPRENEURSHIP

The Risk & Resolve Podcast is your go-to resource for insightful conversations at the intersection of leadership, business ownership, and the insurance industry. Hosted by Ben Conner and Todd Hufford, this podcast dives deep into the challenges and opportunities that leaders face in an ever-changing world. Each episode features candid discussions with business owners, industry experts, and thought leaders, exploring topics like innovation, risk management, and the strategies that drive success. Whether you’re an entrepreneur, executive, or insurance professional, you’ll gain actionable insights and inspiration to navigate today’s complex business landscape. Tune in to Risk & Resolve—where leadership meets resilience.

  1. 10H AGO

    Becoming Churchill: Leadership, History, and the Power of Portrayal with Randy Otto

    In this episode of Risk & Resolve, Ben Conner and Todd Hufford sit down with Randy Otto—internationally recognized Winston Churchill portrayer, keynote speaker, and Churchill historian—to explore how one man’s lifelong passion became a calling. Randy shares the childhood moment that first connected him to Churchill, the mentor who shaped his path, and the actor who helped him transform admiration into embodiment. From Churchill’s leadership, magnanimity, and preparation to the urgent importance of studying history in a fragmented age, this conversation is a powerful reminder that the past still has something vital to teach us. Main Talking Points Randy’s upbringing in Milwaukee and the formative influence of his World War II veteran fatherThe moment that changed everything: watching Winston Churchill’s funeral at age 12How a college professor and mentor helped turn curiosity into lifelong pursuitThe journey from actor to wealth manager while continuing to portray Churchill for decadesWhat Randy learned performing for the “Greatest Generation” and how that shaped his messageThe pivotal meeting with Hal Holbrook that freed Randy to tell stories rather than chase a perfect scriptHow Randy thinks about becoming Churchill on stage—and bringing the audience into that experienceChurchill’s discipline, preparation, and ability to anticipate attacks before they cameThe role Churchill’s speech challenges and dyslexia played in sharpening his communicationWhy Churchill’s magnanimity and refusal to hold grudges mattered as much as his courageWhat younger generations need to know: study history, seek truth, and understand what freedom costsRandy’s reflections on passion, purpose, and the book he still feels called to write

    1h 4m

  2. APR 1

    Leading Through Pressure: Navy Lessons, CEO Decisions, and Building a Stronger Wabash with Brent Yeagy

    In this episode of Risk & Resolve, Ben Conner and Todd Hufford sit down with Brent Yeagy, President and CEO of Wabash, to explore his journey from small-town Indiana to the U.S. Navy submarine force and ultimately to leading one of America’s largest transportation equipment manufacturers. Brent shares how military pressure shaped his leadership, what it took to guide Wabash through COVID, why he refuses to accept the status quo in healthcare, and how leaders can drive breakthrough change by owning outcomes instead of delegating them away. This is a conversation about resilience, responsibility, and leading with clarity when the stakes are high. Main Talking Points Brent’s Indiana roots, early dream of becoming a doctor, and formative years in AlexandriaHis nonlinear path from Purdue to enlisting in the U.S. Navy during the first Gulf WarHow leading young sailors on a nuclear submarine shaped his view of pressure, responsibility, and leadershipWabash’s origin story: disrupting the trailer industry through customization and entrepreneurial speedBrent’s rise through multiple roles at Wabash after joining in 2003The career-defining risk of moving into manufacturing leadership with only 24 hours to decideWhat changed when he became CEO in 2018How Wabash responded to COVID after losing roughly 70% of backlog in weeksWhy command-and-control leadership was necessary in moments of crisisTurning crisis into opportunity by recapitalizing, reorganizing, and reshaping the businessBrent’s philosophy on healthcare: leaders are responsible for outcomes, not just costsWhy CEOs cannot delegate away stewardship of employee healthHis vision for Wabash’s future through resilience, culture, and strategic transformation

    1h 1m

  3. MAR 18

    Building a Family Insurance Empire: Risk, Faith, and 50 Years of Entrepreneurship

    In this special in-person episode of Risk & Resolve, Ben Conner and Todd Hufford sit down with Jim Conner—second-generation insurance entrepreneur and former president of Conner Insurance—to unpack five decades of risk-taking, family business, faith-driven leadership, and hard-earned lessons. From buying the agency at age 22 with a $50,000 note to navigating acquisitions, expansion failures, carrier relationships, and generational transition, Jim shares what it really takes to build—and sustain—a family enterprise. This is a candid conversation about ownership, conviction, legacy, and why burning the ships might be the only way forward. Main Talking Points: The 1973 decision: four brothers buying the family agency with a $50,000 bank noteLessons from Jim’s father: war survivor, project-driven entrepreneur, relentless relationship builderWhy “burning the ships” shaped their mindset toward business survivalGrowing from $150K in revenue to multi-location expansion across IndianaThe risks and realities of managing satellite offices before technologyNegotiating underwriting authority and building carrier leverage (the Maryland story)Why autonomy without accountability exposed the limits of expansionFlatline years, hard cash-flow seasons, and bearing leadership pressure aloneIntegrating faith and business through CBMC, mentorship, and personal convictionThe challenges—and necessity—of generational successionWhy ownership changes everythingLegacy thinking: shifting from building a company to investing in grandchildren

    2h 2m

  4. MAR 4

    From Insurance Executive to Healthcare Whistleblower: Wendell Potter, President and Editor in Chief, Center for Health and Democracy and Health Care Un-Covered

    In this powerful episode of Risk and Resolve, Wendell Potter shares his journey from health insurance executive at Cigna and Humana to becoming one of the most prominent whistleblowers in American healthcare reform. After decades inside the system, Wendell reveals how corporate priorities, shareholder pressure, and political influence shaped the modern insurance landscape—and why he ultimately chose to testify before Congress. Main Talking Points:         •        Growing up in rural Tennessee and early journalism career         •        Transition from reporter to insurance executive at Humana and Cigna         •        Inside look at shareholder-driven healthcare corporations         •        How propaganda shaped public opinion on healthcare reform         •        The rise of high-deductible plans and “consumer-driven healthcare”         •        The Clinton healthcare battle and the Affordable Care Act         •        Medicare Advantage, vertical integration, and PBMs explained         •        The “road to Damascus” moment that changed his life         •        Testifying before Congress and becoming a whistleblower         •        What a fair and sustainable healthcare system could look like

    1h 8m

  5. FEB 18

    Bridging Business and Missions: Erik Cooper on Marketplace Ministry and Global Impact

    In this episode of Risk & Resolve, Ben Conner and Todd Hufford sit down with Erik Cooper, a leader whose career path moved from music to accounting to ministry—and back into the marketplace with a mission. Erik shares how CRF (Community Reinvestment Foundation) leverages affordable housing and assisted living to generate profits that fund global missions through The Stone Table. They unpack the sacred–secular divide, what it means to work from “it is finished,” and how business leaders can view their work as worship and service. From family legacy and nonprofit strategy to the Great Commission and the unreached, this conversation is a blueprint for mission-minded leadership in the marketplace. Main Talking Points: Erik’s nonlinear journey: Belmont music major → IU accounting → worship pastor → church planter → nonprofit presidentThe founding model of CRF: acquiring affordable housing to generate profits for global missionsHow nonprofit real estate can combine high-quality housing impact with sustainable mission fundingWhy The Stone Table was created to bring missions giving and marketplace mobilization in-houseThe meaning behind “The Stone Table” (Narnia inspiration) and anchoring the org to the gospel story“Tetelestai” / “It is finished” as the foundation for work, identity, and purpose in businessDismantling the sacred–secular divide: why marketplace work matters to GodPractical coaching for leaders: putting your work inside God’s story, not asking God to bless your story“Avodah” (labor / worship / service) and viewing everyday work as worshipful serviceMarketplace as missions strategy: why business is often the access point in unreached regionsFamily leadership dynamics: working with his dad and daughter; legacy and stewardshipRisk & Resolve: church planting as entrepreneurial risk; unfinished goals (kids debt-free + global gospel access)

    52 min

  6. FEB 4

    Faith, Power, and the Heartland: Micah Beckwith on Indiana’s Political Future

    In this episode of Risk & Resolve, Ben Conner and Todd Hufford sit down with Indiana Lieutenant Governor Micah Beckwith to explore his journey from ministry and agriculture into statewide leadership. Beckwith shares why he believes faith and politics are inseparable, how grassroots organizing reshaped Indiana’s lieutenant governor race, and why rural communities and agriculture are central to America’s future. From culture wars and education to farming, governance, and the risks of public service, this episode offers a candid look at leadership rooted in conviction. Main Talking Points: Beckwith’s upbringing in agriculture and the dairy industry, including the Moose Tracks origin storyFrom worship pastor to politician: why ministry led him into public officeThe role of faith in governance and why churches should engage civic lifePublic education, parental rights, and cultural influence on the next generationCOVID-era leadership, religious exemptions, and defending individual libertyHow Indiana’s lieutenant governor is chosen through a delegate conventionGrassroots politics: visiting all 92 counties and winning by 63 votesChecks and balances between governor and lieutenant governorAgriculture as national security and Indiana’s economic backboneRevitalizing rural Indiana through infrastructure, broadband, and Main Street investmentRisks of leadership, public criticism, and standing firm in conviction

    1h 14m

  7. JAN 21

    Building A Purpose-Driven Agency That Wins Long-Term with Chance Benbow

    Growth comes from clear values, brave creativity, and showing up for clients when it matters most. In this episode, we sit down with Chance Benbow, CEO of JDA Worldwide, to explore how a client-first mindset and faith-informed leadership drive measurable results across brand, digital, PR, and media. We dig into how courageous creativity, face-to-face trust, and service orientation turned a Midwestern agency into a long-term growth partner for purpose-driven brands. Chance shares lessons from his career, including: • Childhood lessons decoding ads  • Launching an agency in his twenties  • Faith-driven values and leadership  • Beating the 18-month client churn  • Building culture through in-person collaboration  • Creativity across brand, web, PR, and media  • CEO personal branding and impactful PR  • Risk, resolve, and founding Intersection Chance also shares candid insights on pride, legacy, hiring for temperament over résumé, and anchoring campaigns to measurable growth goals rather than shiny deliverables. If this episode resonates, subscribe, share with a teammate, and leave a review—then ask yourself: what part of your growth plan needs more courage and clarity today?

    56 min

  8. JAN 14

    Cybersecurity Preparedness and Cyber Liability Insurance: Prepare, Protect, and Recover

    Cyber Risk Isn’t Just Tech—It’s Business Continuity Cyber threats aren’t just a tech problem—they’re a business problem. In this episode, we bring together a CISO and a senior cyber broker to show how organizations can prepare, protect, and recover when ransomware, email compromise, or vendor outages hit at the worst possible moment. You’ll learn: What the latest FBI numbers really mean and why human error drives most lossesHow to move from vague worry to an evidence-based risk register leadership can fund and trackThe essential building blocks of a modern security program: policies people follow, technical controls that stick, and alignment to frameworks like NIST CSF 2.0 or CIS ControlsRecovery strategies that work under pressure: tested business continuity, documented incident response plans, disaster recovery, and the 3-2-1 backup strategy with routine restore testingCyber insurance demystified: first- and third-party coverage, breach response, forensic support, business interruption, cyber extortion, social engineering, regulatory actions, and reputational harmWhat underwriters expect today—MFA, EDR, offline backups, and phishing training—and how brokers can advocate for better termsAI-driven scams and verification protocols to strengthen defensesWe also break down how to align your cyber insurance with your security posture, so coverage responds when you need it most. With layered defenses, practiced playbooks, and clear coverage, you can absorb shocks and keep revenue moving. If this episode helps you spot a gap in your defenses, subscribe, share with a teammate, and leave a review highlighting the one control you’ll implement this quarter.

    1h 5m
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About

The Risk & Resolve Podcast is your go-to resource for insightful conversations at the intersection of leadership, business ownership, and the insurance industry. Hosted by Ben Conner and Todd Hufford, this podcast dives deep into the challenges and opportunities that leaders face in an ever-changing world. Each episode features candid discussions with business owners, industry experts, and thought leaders, exploring topics like innovation, risk management, and the strategies that drive success. Whether you’re an entrepreneur, executive, or insurance professional, you’ll gain actionable insights and inspiration to navigate today’s complex business landscape. Tune in to Risk & Resolve—where leadership meets resilience.

Information

  • Creator
    Conner Insurance
  • Years Active
    2025 - 2026
  • Episodes
    46
  • Rating
    Clean
  • Copyright
    © 2026 Conner Insurance
  • Show Website
    Risk & Resolve