Flip the Cap: Recent Episodes
Kathryn Smith
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.
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
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
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
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:
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- [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
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
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/.
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/
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]
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
- [00:09:15] Tech's Impact On Customer Expectations
- [00:11:58] Why marketing matters (when you aren’t in marketing)
- [00:18:29] Having a healthy marketing ecosystem
- [00:23:10] 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/
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/
In this episode of Flip the Cap, host Kathryn Smith and special guest Bruce Peddle, President of Jencap Insurance Services, take listeners on a journey through the dynamic world of insurance, the importance of innovative technology, and they unlock the secrets to successful change management. Tap into Bruce’s wealth of knowledge as he explores topics related to small transactional business, M&A, and more.
Episode Highlights:
- (3:24) The best investment Bruce ever made
- (8:19) Interesting facts you likely don’t know about Bruce (teaser: tattoos, hockey, kicked out of the military, oh my!)
- (12:36) Biggest trends impacting the binding authority / small transactional area of the insurance industry
- (15:34) Growth in MGA/MGU model and its impact
- (17:54) The importance of technology and innovation for small transactional insurance risks
- (23:40) The importance of change management and sound operational strategies to streamline M&A
- (32:32) Why insurance is the hidden gem of the American economy
Learn more about Jencap’s expansive binding capabilities at https://jencapgroup.com/areas-of-specialization/binding-authority/ .
In this episode, Jencap Director and certified catastrophe modeler, Bruce Norris delves into the intricacies of catastrophe modeling with our host, Kathryn Smith. With decades of experience in catastrophe analysis and technology, Bruce sheds light on the fundamentals of CAT modeling, explores the nuances of PML and AAL, and how a model’s data impacts insurance outcomes.
Episode Highlights:
- 9:24 How Bruce's backpacking hobby led to sightings of his spirit animal
- 10:49 Revealing the "favorite failure" that paved the path to Bruce's biggest success
- 16:33 Understanding CAT modeling and its crucial role in the insurance industry
- 18:46 Breaking down PML and AAL
- 20:45 Why the model and carrier pricing aren't always in sync
- 22:42 What factors are influencing the data in the model?
- 25:05 The importance of quality and well formatted data
- 27:02 The relationship between ITV and CAT modeling
- 28:26 Jencap’s property team advantage
Learn more about Jencap’s expansive property capabilities at https://jencapgroup.com/custom-solutions/property/
Tune into a special edition of Flip the Cap where Kathryn Smith sits down with John Jennings, Jencap CEO, as he shares insight into his early days in the industry and the pivotal moments that led to the creation of Jencap. In this episode, Jennings unveils the strategies fueling Jencap's growth, the secret to successful M&A integrations, and interesting predictions for the insurance industry in 2024. Don't miss this insider's view into Jencap's past, present, and future.
Episode highlights include:
- The Beginning of John Jennings’ Insurance Journey 1:32-2:28
- Adventures On the Green & Off the Beaten Path 3:12-3:53
- Greatest Accomplishments with John Jennings 3:54-4:46
- John Jennings’ Formula to Success 4:46-5:52
- Why should someone consider insurance as a career? 6:00-7:31
- Learn about the events leading to Jencap’s launch 9:16-11:50
- What makes a company attractive to Jencap and our 2024 M&A predictions 11:51-16:22
- Jencap’s CEO shares its 2023 success 16:23-18:11
- Predictions for key trends in 2024 that will impact the industry 18:12-21:55
- The Jencap Advantage: Collaboration 21:55-26:12
In this episode of Flip the Cap, host Kathryn Smith sits down with Jeff Sandy, Jencap's Vice President of Workers’ Compensation. Being a statutory coverage, the inputs that determine the best carrier partner for a Workers’ Compensation risk are very different from the P&C world. There are also numerous alternative plans available depending on the risk that are full of nuanced complexities. With Jeff’s extensive expertise, listeners uncover valuable strategies to navigate audits, how to avoid misclassifying a job, and general guidance on navigating this unprecedented marketplace.
Episode highlights include:
- Jeff reveals his superpower in the insurance industry (03:15)
- His involvement in Gamma Iota Sigma and the important role the organization plays in our industry (04:23)
- Break down of the alternative WC plans available based on the risk profile (12:08)
- The most misunderstood class of business for Workers’ Comp (14:21)
- Key considerations to best navigate audits (16:08)
In this episode of Flip The Cap, Kathryn Smith sits down with special guest Michael De Feo, Senior Vice President of Jencap’s Professional Lines Practice. Michael and Kathryn explore the volatile world of the professional lines industry - talking in great detail on what’s happening with Directors & Officers (D&O) Insurance, Errors and Omissions (E&O) Insurance, and financial institution risks. The game is changing so quickly that it’s critical for agents to understand the current marketplace trends and changes happening real time.
Episode highlights
- Why Use a Wholesaler to Quote When You Can Go Direct?
- The Rise of Errors & Omissions Claims
- New Professional Lines Products for Emerging Risks
- Important Risk Considerations for M&A Activity
- Importance of Working with Specialized Broker on Financial Institution Risks
On this episode of Flip The Cap, Kathryn Smith sits down with special guest Roman Atkielski, Transportation Practice Leader at Jencap. He is an insurance veteran with 30+ years of experience in underwriting, marketing and program development. Roman has dedicated his entire career to transportation insurance, holding various roles with insurance carriers, reinsurers, and MGAs.
On this episode of Flip The Cap, Kathryn Smith sits down with John LaCava (Chief Operating Officer of Jencap) to discuss the program management side of the insurance business. They dig into how the shift in the E&S marketplace has impacted programs, the importance of data and analytics in our industry, and Jencap’s strength as one of our country’s largest program administrators. John also reveals his past rockstar life and discusses the charity he so proudly played a part in founding.
Episode Highlights:
1:38: John LaCava reveals his rockstar musical background
4:55: How John found a career in insurance
8:30: How a St. Patrick’s Day with friends gave birth to a hundred million dollar children’s charity
15:45: Trends impacting the current rate environment, capacity issues and property valuations
19:45 How the shift to the E&S market has impacted programs
21:45 Data analytics’ role in risk selection and pricing
29:37 The most beneficial trend over the last few years has been data and analytics
30:09 Jencap’s strengths as one of the largest insurance program administrators
35:12: Jencap’s program structure and value proposition to retailers
Welcome to Flip the Cap — the insurance industry’s premier podcast! In this episode, Kathryn Smith discusses important property insurance trends with Ben Beazley, EVP of Property at Jencap. Ben shares valuable information about alternative capital trends, how to best position your insureds for their upcoming renewals, the validity of modeling, trends he expects to see continue in 2023, and so much more!
Episode Highlights:
1:31 : Getting to know Ben Beazley
8:02 : The benefits Jencap offers as a wholesaler
11:55 : Trends in alternative capital and how it has impacted property insurance
14:58 : Predictions for wholesale brokerage growth in 2023
18:02 : Important trends in rates, retentions, and reinsurance
20:47 : The validity and impact of modeling on property underwriting
23:57: Best practices for agents to ensure a smooth property renewal process
28: 37: The Jencap property advantage
Learn more about Jencap’s expansive property capabilities at https://jencapgroup.com/about-us/.
Welcome to Flip the Cap! On today’s show, Kathryn sits down with Deborah Dioguardi, Senior Vice President of Jencap Specialty Insurance Services. Deborah is a highly sought-after Professional, Cyber and Management Liability specialist broker. In the interview, she discusses the interesting evolution of cyber insurance, one of the commonly missed professional lines coverages, what she expects the coming year to look like for our retail agency partners, and more. Plus, spoiler alert: she may or may not claim the top spot in the Flip the Cap leaderboard!
1:07 Surprising facts about Deborah’s Dioguardi’s background
4:20 What success looks like when working with retail brokers and agents
8:25 Ins and outs of underwriting cyber insurance and its evolution over time
11:23 How retail agents can get unmatched market access
13:32 Benefit of policy comparisons through quality, specialty wholesalers
16:22 How to navigate the professional lines world in a soft market
16:59 What brokers often don’t know about Directors & Officers insurance
19:59 Forecasting what to expect in 2023 for the professional lines industry
Welcome to Flip the Cap! Today on the show Kathryn sits down with Mark Maher, President of Jencap, to discuss everything you need to know about the rapidly changing insurance industry and how Jencap is poised to meet the challenges. From the war on talent, active M&A environment, climate change and everything in between, you don't want to miss it!
Episode Highlights:
1:25 The surprising way Mark lets off steam
5:49 The rapidly changing retail insurance space due to M&A activity
8:23 The biggest challenge facing the insurance industry and its rate impact
10:08 Combating the aging insurance workforce
15:00 Discussion on Jencap’s broad reach and specialized teams
20:54 Opportunities that exist with the expanding E&S marketplace
22:17 The impact of consolidation in the wholesale and retail insurance space
Learn more about Jencap’s expansive capabilities and expert leadership team at https://jencapgroup.com/about-us/.
Welcome to Flip the Cap! Today on the show Kathryn sits down with Canaan Crouch to discuss everything you need to know about the environmental insurance marketplace. Plus, when it comes time to Flip the Cap, Canaan sets a record. You don't want to miss it!
The insurance industry's premier podcast, Flip the Cap, premieres November 2022.
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.
Make sure to give us a follow, you want want to miss the premiere!
Environmental is one of the lesser understood branches of insurance. On the first episode of Flip the Cap, Kathryn sits down with Canaan Crouch do discuss all things environmental.