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Flip the Cap

Flip the Cap

Hosted by Kathryn Smith

BusinessManagementInterviews guests
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Episodes

23

Latest episode

Apr 2026

Language

EN

About the show

Working for one of the largest insurance brokerages in the nation, you could say Jencap's experts know what they're talking about. Why not share our insurance veteran experience with agents and brokers trying to navigate a world of unprecedented change? Join Kathryn Smith, Director of Marketing at Jencap, and leading professionals in the insurance industry, as she pops the top on ALL things insurance, brokerage, and coverage. In each episode, Kathryn talks with industry leaders on trends, tactics, and tools to manage complex cases, provide exceptional service, and adapt to an ever-changing environment.

Listen to episodes

23 recent
April 1, 202622 min

Flip the Cap Episode 22 | ​​Jencap 10 Year Anniversary Edition: John Jennings on Growth, Culture, and What's Next

Welcome to a special edition of Flip the Cap, the insurance industry's premier podcast. In this milestone episode, Kathryn Smith sits down with Jencap CEO, John Jennings, to celebrate Jencap's 10th anniversary and reflect on the journey from startup to industry leader. Jennings shares how Jencap was born out of a need in the marketplace, the acquisition strategy that fueled its rapid growth, and the culture that continues to set the company apart. He also offers candid insight into what comes next as the market shifts and Jencap sets its sights on the future. If you want a behind-the-scenes look at the company's evolution, leadership philosophy, and long-term vision, this episode is for you.   🎧 Tune in now to our new season of Flip the Cap, the industry's premier podcast that delivers insurance insights with a twist!    Episode Highlights Include: [0:54-4:51] How Jencap Got its Start [04:54-07:30] Jencap's M&A Strategy  [07:39-09:26] Jencap CEO's Entrepreneurial Spirit and Internal Parallels [11:37-14:32] Jencap's #1 Thing to Attribute its Success [15:49-17:44] Next Milestones for Jencap [17:45-20:49] What the Next Five Years Look Like at Jencap

November 12, 202533 min

Flip the Cap Episode 21 | Global E&S Trends, Emerging Risks and 2026 Predictions

Welcome to Flip the Cap, the insurance industry's premier podcast! In this episode, Kathryn Smith sits down with special guest Oliver Pidgeon, Managing Director at Bowood (part of Howden Re), and Jencap's commercial lines brokers, Jim Andreoli and Tony O'Donnell. They unpack how a global marketplace of syndicates prices risk with data and discipline, and how reinsurance acts as the "tide" moving U.S. rates and capacity. This insightful crew discusses key global trends and their impact on our domestic insurance marketplace, emerging risks in the E&S space, and offers straight-talk predictions for 2026. If you're looking to better understand Lloyd's of London and the moving pieces that make up the Excess and Surplus lines market, this episode is for you.   🎧 Tune in now to our new season of Flip the Cap, the industry's premier podcast that delivers insurance insights with a twist!    Episode Highlights Include: [06:00-12:13] Global trends and their connection to domestic trends [15:44-21:37] Emerging risks in the E&S marketplace  [23:41-28:03] New players entering the domestic market (MGAs) [28:03-32:37] Predictions for the E&S market in 2026

August 25, 202527 min

Flip the Cap Episode 20 | The Energy Pivot: What's Here to Stay and What's On the Way

Welcome to Flip the Cap, the insurance industry's premier podcast! In this episode, Kathryn Smith sits down with Jencap's Canaan Crouch, EVP of Environmental and Energy Practice, and Loren Henry, VP of Environmental and Energy Practice. Together, they break down how recent tariffs, new federal policies, and global geopolitical pressures are reshaping the environmental and energy sectors, and what it means for insurance.   With the recent pivot away from solar energy and towards new energy sources, Canaan and Loren share real-world examples of relevant emerging trends, risks, market impacts, and environmental considerations. Retail agents can expect insightful strategies that keep them knowledgeable, able to navigate volatile price swings, and keep their clients businesses properly protected every step of the way.   If your clients operate businesses that intersect with renewable energy, oil and gas, or the next wave of mobile nuclear technology, this episode offers actionable insights to keep you ahead of the curve.   🎧 Tune in now to our new season of Flip the Cap, the industry's premier podcast that delivers insurance insights with a twist!    Episode Highlights Include: [03:50-09:19] Emerging Alternatives to Solar Energy and Their Impact [09:23-13:16] Risk Types Most Affected by Increasing Tariffs [13:17-20:20] Nuclear and Hydroelectric Power - Here to Stay? [20:52-23:21] Short Term vs. Long Term Effect on Energy Sources [23:45-26:20] How Retail Agents Can Navigate the Pivot in the Energy Industry

July 24, 202534 min

Flip the Cap Episode 19 | Cannabis Insurance Insights: Regulatory Shifts, Coverage Gaps & Expert Strategies

Welcome to Flip the Cap, the insurance industry's premier podcast! In this episode, Kathryn Smith sits down with Jencap's national practice leader for cannabis, Lee Woodruff, and Director of Business Development at Cannasure, Jim McErlean, to explore the ever‑changing cannabis insurance market. These cannabis experts unpack how state‑by‑state regulatory environments affect underwriting, highlight critical emerging coverages, and offer their #1 piece of advice for agents working with cannabis businesses. Our retail partners will gain actionable strategies to navigate the unique nuances of cannabis insurance and get a glimpse into the future of this market.   🎧 Tune in now to our new season of Flip the Cap, the industry's premier podcast that delivers insurance insights with a twist!    Episode Highlights Include: [1:17-04:06] Cannabis Insurance Market Trends: Reinsurance, Margins & Coverage Pressure [04:06-10:43] Essential Cannabis Insurance Coverages Agents Can't Overlook [10:43-15:52] Tips to Navigate State Specific Regulatory Environments  [17:44 - 21:47] Hard‑to‑Place Cannabis Risks: CBD, Hemp & Kratom Challenges [22:08-29:54] Hidden Gaps in Cannabis Insurance Policies—and How to Avoid Them [30:02-33:57] #1 Tip for Agents Selling Cannabis Insurance from Industry Experts

April 16, 202516 min

Flip the Cap Episode 18 | The Big Build: Inside Construction Wrap-Up Programs

Welcome to Flip the Cap, the insurance industry's premier podcast! In this episode, Kathryn Smith sits down with Michael Yovino, Jencap's Wrap Up Construction Practice Leader, and Consolidated Risk Solutions' President, Josh Rogove. Their discussion covers when wrap-up programs are warranted, the risks of not using a qualified TPA, and how to perform a cost benefits analysis for these programs. Mike and Josh break down the nuances of OCIPs (Owner-Controlled Insurance Programs) and CCIPs (Contractor-Controlled Insurance Programs), how they mitigate risks, and why proper administration is crucial for cost certainty and claims handling. If you're looking for insights on navigating construction insurance, minimizing risk, and maximizing cost efficiencies, this episode is a must-listen.   🎧 Tune in now to our new season of Flip the Cap, the industry's premier podcast that delivers insurance insights with a twist!    Episode Highlights Include:   -What Wrap Up Construction Programs Cover -A TPA's Primary Role With Wrap-Ups -Benefits of a Wrap Up Program for Retail Agents -Pitfalls of Jurisdictional Variations, Including Construction Defect States

March 19, 202519 min

Flip the Cap Episode 17 | Flames of Uncertainty: How Wildfires Are Shaping Insurance

Welcome to Flip the Cap, the insurance industry's premier podcast! In this episode, Kathryn Smith sits down with Jencap's Ben Beazley, National Property Practice Leader, and Louis Reynaud, Vice President and Wildfire Strategist, to break down the best approach to wildfire underwriting and risk mitigation.     This episode offers retail agents tangible ways to best approach wildfire prone property risks, along with how to combat the ever-increasing severity and unpredictability of weather patterns.   Episode Highlights Include: 1:14-4:11 Industry progress that's been made since 2020 wildfires 4:12-6:39 Key players working to restore stability in wildfire-prone areas 6:39-11:35 How to combat the ever-increasing severity and unpredictability of weather patterns 11:36-15:54 Tips for Retailers to successfully place wildfire risks 17:00-end Most viable path to restore stability with wildfire risks   🎧 Tune in now to our new version of Flip the Cap, the industry's premier podcast that delivers insurance insights with a twist!    Learn more about Jencap's property solutions here: https://jencapgroup.com/custom-solutions/property/.

November 6, 202426 min

Flip the Cap Episode 16 | Beyond Professional Liability: Ancillary Lines You Can't Ignore

Welcome to Flip the Cap, the insurance industry's premier podcast! In this episode, Kathryn Smith sits down with Anthony Manna, SVP at Jencap and a top-ranked broker specializing in professional, management, and cyber liability. Known for his expertise and industry accolades, Anthony shares the most relevant emerging trends in this space. He also breaks down several ancillary coverage lines that agents need to be selling (yesterday). Stay a step ahead of your competition and on the front end of the ever-changing insurance marketplace with his valuable insights. Plot twist: Anthony also breaks down why a wholesaler is needed more than ever in this soft Professional Lines market.   Episode Highlights Include: The most relevant emerging trends in professional, management and cyber liability; including EPLI, cyber security and risk sizes. (8:56) Ancillary coverages lines that agents need to be selling (yesterday) (16:25) Why Jencap is needed more than ever in this soft Professional Lines market (24:26)   Learn more about Jencap's expansive professional lines capabilities at https://jencapgroup.com/custom-solutions/professional/

September 20, 202421 min

Flip the Cap Episode 15 | Workers' Comp Compass: Expert Advice from Kristi Tinker

Welcome to Flip the Cap, the insurance industry's premier podcast! In this episode, Kathryn Smith sits down with Kristi Tinker, a seasoned Workers' Compensation broker at Jencap with over 20 years of specialized experience. Together, they dive into the complexities of Workers' Compensation, exploring commonly misused class codes, industry trends, and noteworthy regulatory changes. They also discuss the unique challenges of the New York Workers' Compensation market, ways to avoid USL&H fines for your clients, and much more. Episode Highlights Include: Kristi's predictions for the future of Workers' Comp cue AI, mental health, cannabis, and more [00:16:28] Key differences between Workers' Comp and USL&H [00:12:42] The most misused class code in Workers' Comp [00:11:08] Important regulatory changes in Workers' Comp industry [00:09:18] Current landscape of Workers' Comp marketplace including NY [00:07:16] Why agents should rely on Jencap for Workers' Comp [00:19:20]

August 14, 202445 min

Flip the Cap Episode 14 | Marketing for Non-Marketers: How to Boost the Bottom Line

Welcome to Flip the Cap, the insurance industry's premier podcast! In this episode, Kathryn Smith sits down with Eric Holtzclaw and Cynthia Hayes of Liger, a full-service marketing firm. The three explore the dynamic world of marketing and its intersection with the insurance industry. They delve into how artificial intelligence is reshaping content creation and social media strategies while emphasizing the need for authentic, human-driven communication. Discover the importance of maintaining brand consistency, leveraging the PESO model (paid, earned, shared, and owned media), and the transformative power of video in engaging audiences.   The Liger team provides actionable tips on enhancing your marketing ecosystem, from optimizing your website and creating relevant content to harnessing LinkedIn and personal branding. They also discuss the significance of internal alignment with your brand's mission, effective collaboration between sales and marketing teams, and the strategic use of AI tools to boost domain authority and content relevance.   Episode Highlights: [00:02:46] Disruptive changes in the marketing industry over the last 12 months [00:07:41] Key changes and how to stop the scroll [00:09:15] Tech's Impact On Customer Expectations [00:11:58] Why marketing matters (when you aren't in marketing) [00:18:29] Building a healthy marketing ecosystem [00:34:09] What insurance professionals can leverage in the marketing world Keep up with the latest industry insights from Jencap: https://jencapgroup.com/insights/

June 20, 202420 min

Flip the Cap Episode 13 | Loren Henry, Recharging the Energy Sector

Welcome to Flip the Cap, the insurance industry's premier podcast! In this episode, Kathryn Smith sits down with Loren Henry, Energy Practice Leader at Jencap, to illuminate everything you need to know about the environmental, energy, marine and hazmat/oilfield industries. Loren sheds light on the environmental implications of "going green", trends impacting the energy industry, and provides several examples that highlight the critical need to work with a specialized broker on energy risks. Listen now so you can tackle your next clients' environmental / energy risk with confidence! Episode Highlights: (3:16) What do Snoop Dogg, D1 soccer, and radio talk shows have in common? Loren Henry! (8:40) Environmental versus energy - where's the line? (9:45) Outlier P&C trends impacting the energy industry (12:59) Pros and cons to "going green" (15:56) Why an agent should work with a specialized energy broker (19:14) Launch of Jencap's new energy practice Learn more about Jencap's environmental capabilities: https://jencapgroup.com/custom-solutions/environmental/

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