Flip the Cap

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

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

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

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. 1. [1:17-04:06] Cannabis Insurance Market Trends: Reinsurance, Margins & Coverage Pressure 2. [04:06-10:43] Essential Cannabis Insurance Coverages Agents Can't Overlook 3. [10:43-15:52] Tips to Navigate State Specific Regulatory Environments 4. [17:44 - 21:47] Hard‑to‑Place Cannabis Risks: CBD, Hemp & Kratom Challenges 5. [22:08-29:54] Hidden Gaps in Cannabis Insurance Policies—and How to Avoid Them 6. [30:02-33:57] #1 Tip for Agents Selling Cannabis Insurance from Industry Experts

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