Flip the Cap – Details, episodes & analysis

Podcast details

Technical and general information from the podcast's RSS feed.

Flip the Cap

Kathryn Smith

Business

Frequency: 1 episode/55d. Total Eps: 20

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.

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Apple Podcasts

🇬🇧 Great Britain - management
04/08/2025
#91
🇺🇸 USA - management
04/08/2025
#98
🇬🇧 Great Britain - management
03/08/2025
#54
🇺🇸 USA - management
03/08/2025
#63
🇨🇦 Canada - management
02/08/2025
#66
🇬🇧 Great Britain - management
02/08/2025
#40
🇺🇸 USA - management
02/08/2025
#53

Spotify

No recent rankings available

Shared links between episodes and podcasts

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https://jencapgroup.com/custom-solutions/property/
4 shares
https://jencapgroup.com/about-us/
2 shares
https://jencapgroup.com/custom-solutions/professional/
2 shares

https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa3VCdjhfcU16MEZsX2M4bHVMWElzdjZJUWlDQXxBQ3Jtc0trbmFxVmVPQU9HS3ZqQUNTelVEc0JSSHJzZnRIRjR3R3JpUEFfQldvNmFTTXltLXRYR0dRdzZiX1d6Mmp4ZE5PYXdDVGdiVk1rSjk4aVBWcGVTN1BFdWhBVXlKZm1VUGtBMkVRYjA1N3QxR1Y1d2k3OA&q=https%3A%2F%2Fjencapgroup.com%2Fabout-us%2F&v=MmxYWfqbK9o
1 share

RSS feed quality and score

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RSS feed quality

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Score global : 49%

Publication history

Monthly episode publishing history over the past years.

Year

Latest published episodes

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

Thursday, July 24, 2025 • Duration 34:24

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. [1:17-04:06] 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

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

Wednesday, April 16, 2025 • Duration 16:21

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

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Exploring the Cannabis Industry with self-proclaimed Cannabis Insurance Ninja

Wednesday, December 13, 2023 • Duration 25:05

Flip the Cap with Jeff Sandy | The Insurance Unicorn: Workers’ Compensation

Friday, October 20, 2023 • Duration 20:18

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)

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Flip the Cap | Exploring Executive Risk and Financial Institutions with Michael De Feo

Tuesday, September 26, 2023 • Duration 23:20

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

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Flip the Cap | Behind the Wheel with Roman Atkielski

Monday, August 21, 2023 • Duration 26:16

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.

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Flip the Cap | Exploring Specialized Industry Topics with John LaCava

Tuesday, May 16, 2023 • Duration 36:13

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

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Flip the Cap | Ben Beazley, EVP of Property at Jencap, Talks Property Insurance

Wednesday, April 5, 2023 • Duration 32:28

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/.

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Flip the Cap | Impactful Insurance Trends and Twists

Wednesday, January 18, 2023 • Duration 27:02

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/.

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Flip the Cap | The Ins and Outs of Cyber Liability and Professional Lines

Wednesday, January 18, 2023 • Duration 23:36

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

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Flip the Cap – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

RSS feed quality and score

Publication history

Latest published episodes

Related Shows Based on Content Similarities

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Flip the Cap – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

Other7

Youtube1

RSS feed quality and score

Publication history

Latest published episodes

Similar podcasts and content

Related Shows Based on Content Similarities

Related Shows Based on Content Similarities

Other7

Youtube1

Apple Podcasts

Spotify