Episode Info

Peter Settel, CEO of Bold Penguin, is a business and technology leader with a proven track record of leading technology-led growth companies across the insurance sector.

Prior to Bold Penguin, Settel was the Enterprise Chief Strategy Officer and Information Officer at American Family Insurance. Before that, Peter spent 17 years as a senior executive leading capability development at Homesite Insurance. Peter spent his early career at Cambridge Technology Partners and as a leader at MediaLink Interactive.

Settel holds a Bachelor of Science degree in Finance and Investments from Babson College.

Introduction and Background:

Recorded live at ITC Vegas 2025, Peter shares his extensive experience in the insurance technology sector, spanning over 25 years, and discusses the transformative journey of Bold Penguin from a startup to a leading enterprise technology provider in the insurance industry.

Key Discussion Points:

Introduction to Peter Settel and Bold Penguin:

• Peter Settel introduces himself and provides a brief overview of his career in insurance technology, starting with his role at Homesite Insurance and his journey through various leadership positions.

• An introduction to Bold Penguin, highlighting its evolution from a venture-backed startup to a significant player in the insurance technology space.

Bold Penguin's Strategic Growth:

• Discussion on the acquisition of Bold Penguin by American Family Insurance in 2021 and Peter's transition to CEO .

• Insights into Bold Penguin's strategy to maintain its independence while serving the broader insurance market .

Technology and Market Impact:

• Exploration of how Bold Penguin leverages digital technologies to enhance distribution platforms for small commercial insurance .

• The role of AI and digital transformation in reshaping the insurance landscape, with a focus on competitive positioning .

Future of Insurance Distribution:

• Peter discusses the importance of maintaining a robust distribution network that includes agents, brokers, and carriers .

• The challenges and opportunities in balancing traditional insurance practices with innovative digital solutions .

Audience Engagement:

• The episode encourages listeners to think about the future of insurance distribution and the role of technology in driving industry change.

Conclusion: Peter Settel provides a compelling vision for the future of insurance, emphasizing the critical role of technology in driving efficiency and growth in the industry. This episode is a must-listen for anyone interested in the intersection of insurance and technology.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Info

With a vision of completely transforming the car insurance industry, Alex founded Root in 2015 on the principle that rates should be based primarily on driving behaviors, not demographics. As Founder and Chief Executive Officer, Alex leads the company in revolutionizing this outdated industry using mobile technology and data science to offer personalized car insurance rates to good drivers. Today, Root Insurance is the largest Property & Casualty InsurTech in the country.

Throughout his insurance career, Alex has built expertise in pricing and reserving, finance, and mergers and acquisitions. Before founding Root, Alex worked at Nationwide Insurance as a senior strategy consultant for the Property & Casualty lines of the business. Alex is a Fellow of the Casualty Actuarial Society, a Henry Crown Fellow of the Aspen Institute, and a member of the American Academy of Actuaries.

Episode Highlights

Alex Timm, leveraging his actuarial background and experience in corporate strategy, co-founded Root Insurance to revolutionize the insurance industry by focusing on customer-centric experiences and technological innovation. Root Insurance integrates big data and machine learning to enhance pricing models and customer experiences, notably through partnerships like the one with Carvana. The company prides itself on controlling its technology stack, enabling a seamless insurance purchase process. Alex highlights the importance of diversity and continuous technological investment to address industry challenges and drive innovation. Root Insurance remains committed to transforming the insurance landscape by embedding insurance solutions and refining its technological capabilities.

Introduction and Background:

• Alex Timm, an actuary by training, co-founded Root Insurance on March 14, 2015. His background in the insurance industry is deeply rooted, with his father being an insurance entrepreneur.

• Timm's passion for math and his experience in corporate strategy at a large insurance carrier led him to identify gaps in customer expectations and technological advancements within the industry.

Vision and Innovation:

• Root Insurance was founded to address the lack of customer-centric experiences in the insurance industry. Timm was driven by the advent of big data and machine learning, aiming to leverage these technologies to match price to risk more effectively .

• The company has developed a seamless customer experience by embedding insurance directly into the vehicle purchase process, exemplified by their partnership with Carvana.

Technological Advancements:

• Root Insurance controls its technology stack, allowing for seamless integration and a three-click purchase experience. This technological control is a significant advantage, enabling the company to refine pricing models and algorithms continuously.

• The use of telematics and other data sources is central to Root's strategy, but the company also emphasizes that telematics is just one aspect of their broader technological and pricing strategy.

Challenges and Industry Insights:

• Timm acknowledges the challenges of underwriting profitably and the need for innovation in the insurance industry. He emphasizes the importance of diversity in thought and background to drive innovation.

• The interview touches on the broader industry context, including the challenges of going public and the need for continuous investment in technology to deploy advanced algorithms.

Conclusion:

• Alex Timm's leadership at Root Insurance is characterized by a commitment to innovation, customer experience, and leveraging technology to transform the insurance industry. The company continues to evolve, focusing on embedding insurance solutions and refining their technological capabilities.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Info

I provide insights from InsureTech Connect Vegas 2025, focusing on the significant impact of artificial intelligence (AI) in the industry. I saw the power of the democratization and proliferation of AI models, which are enabling new solutions in the market. The emphasis was on empowerment rather than replacing staff, recognizing the need for more workforce due to overwork and burnout.

I also got to be a judge at Guidewire's InsurePitch event, which featured pitches from five insurtechs, four of which focus on claims. This reflects a renewed interest in claims within the industry.

Networking was a significant aspect of the conference as always, and it seemed like you never had enough time given how many great conversations can be had in this very unique coming together of so many forward thinking people and companies in Insurance.

Episode Highlights

This is my recap of the ITC Vegas 2025 conference, highlighting several key insights:

1. Impact of Artificial Intelligence: A major theme was the transformative role of AI in the industry. The conference emphasized the democratization and widespread adoption of AI models, which are creating new market solutions. The focus is on using AI to empower the workforce rather than replace it, addressing issues like overwork and burnout.

2. Claims Back in the Spotlight: There was a renewed focus on Claims-specific solutions, with 80% of the companies competing for the Guidewire InsurPitch prize being Claims solutions.

3. Networking and Collaboration: Networking was a crucial part of the conference, with attendees engaging to drive industry progress. Despite time constraints, the speaker valued the opportunity to connect with peers and share ideas, which is vital for industry advancement.

Overall, the conference had a strong focus on AI's pivotal role in industry transformation, the centrality of claims in insurance, and the importance of networking and collaboration for future growth.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Info

Rob Galbraith is the founder and CEO of Forestview Insights and is the author of the international bestselling book, The End of Insurance As We Know It.

Rob is an award-winning speaker who has shared his unique insights at numerous events around the globe on the topics of innovation, insurtech, and the future of insurance.

Rob has over 25 years of experience in the financial services industry in a variety of innovation and leadership positions at AF Group, USAA, and the Federal Reserve Board. 

Episode Highlights

The interview with Rob Galbraith at the 2025 PLRB Innovation Summit covers several key topics related to innovation in the insurance industry. Rob Galbraith, the founder and CEO of Forestview Insights, discusses his role in consulting and training traditional companies, particularly in the insurance sector, to foster a culture of innovation.

Key points from the interview include:

• Building a Culture of Innovation: Rob emphasizes the importance of creating a sustainable culture of innovation within companies, which goes beyond the efforts of a single leader or project. He highlights that innovation should be treated as a discipline similar to underwriting or actuarial science.

• Challenges in Innovation: He acknowledges the difficulties companies face in maintaining innovation, particularly in aligning IT projects with business needs. Rob shares his experiences with core system projects and the challenges of implementing new systems that meet business requirements.

• Role of AI: The discussion touches on the potential of AI to address technical debt and streamline processes in the insurance industry. Rob shares insights on how AI can help in summarizing regulatory documents and customizing systems without extensive manual programming.

• Long-term Perspective in Insurance: Rob discusses the long-term nature of the insurance business and how this perspective can be advantageous for innovation. He suggests that the industry's focus on long-term outcomes could support a more thoughtful approach to innovation.

Overall, the interview provides valuable insights into the strategies and challenges of fostering innovation in the insurance industry, with a focus on the role of leadership, culture, and technology.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Info

Cayce E. Lynch is the National Managing Partner and an Equity Partner at Tyson & Mendes. In this capacity, she leads the firm's strategic vision and execution across all offices, focusing on optimizing the firm's performance and addressing challenges in the evolving insurance defense industry. As part of the firm's executive leadership team, Ms. Lynch is passionate about fostering a culture centered on people while driving results, reflecting her belief that organizations thrive when they balance purpose with humanity.

Under Ms. Lynch's leadership, the firm has more than quadrupled in size and strengthened its reputation as a leader in insurance defense. She is the founder of several transformative initiatives, including the Tyson & Mendes Women's Initiative, Young Professionals Group, and Diversity & Inclusion Committee, which provide mentorship and support for the firm's attorneys and staff as well as insurance professionals nationwide. She also established Tyson & Mendes University, the firm's premier internal education program that delivers unparalleled training for attorneys to ensure excellence in legal practice and client service.

In her leadership, Ms. Lynch prioritizes work-life harmony over rigid concepts of "balance." She is a vocal advocate for supporting working parents, empowering underrepresented groups, and encouraging individuals to fully embrace authenticity in their work. Her initiatives and approach aim to support employees in thriving personally and professionally. An industry-recognized speaker and educator, Ms. Lynch regularly presents CE and MCLE updates on topics such as preventing Nuclear Verdicts® and social inflation. She also serves as faculty for the Nuclear Verdicts Defense Institute, helping train defense professionals to combat Nuclear Verdict® trends.

Ms. Lynch has been recognized with numerous awards, including San Diego Business Journal's "Business Women of the Year" Award (2017), "Top 40 Under 40" by both San Diego Metro and San Diego Business Journal (2018, 2019), and CLM's inaugural "Phenoms Under 40" (2022). She has also been listed as a "Woman of Influence in Law" (2021-2023)and a "Leader of Influence in Law" (2023) by San Diego Business Journal.

Ms. Lynch earned her J.D., cum laude, in 2011 from the William S. Richardson School of Law, University of Hawaii at Manoa, where she served as the Outside Articles Editor for the University of Hawaii Law Review. After graduation, she clerked for Associate Justice James Duffy at the Hawaii Supreme Court. She is licensed to practice law in California and Colorado.

Episode Highlights

1. The Apex Method:

   • Cayce Lynch introduces the "Apex" method, a holistic approach designed to prevent nuclear verdicts by diffusing juror anger from the onset of a case. This method emphasizes reasonableness and being a good human.

2. Core Four Strategies:

   • The Apex method includes four key strategies, referred to as the "Core Four," which are crucial in preventing juror anger and, consequently, nuclear verdicts. Research indicates that these strategies are often not utilized by the defense.

3. Data-Driven Insights:

   • The book is backed by extensive research, including the analysis of trial transcripts from 100 nuclear verdicts over the past decade. This research highlights the importance of understanding the psychological tactics used by the plaintiff's bar.

4. Message of Hope:

   • Despite the increasing challenge of nuclear verdicts, Cayce Lynch offers a message of hope. By changing defense strategies and presentations in court, there is potential to alter the trajectory of these verdicts and improve the viability of the insurance industry.

5. Upcoming Book Release:

   • "Nuclear Verdicts: The Apex" is set to launch on October 22nd, with pre-sales available from early September.

These insights from Cayce Lynch's interview provide a comprehensive look at the challenges and solutions surrounding nuclear verdicts, offering valuable strategies for defense attorneys and claims professionals.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Info

In this episode, I explore the paradox that is insurance. We buy risk from others, yet we are risk averse ourselves. Looking at the work of underwriters as compared to venture investors, you find that the skillset is actually nearly identical, but it's being deployed in opposite directions. I discuss that, why that might be, and what someone trying to bring innovation and change to insurance should keep in mind given this reality.

Episode Highlights

This episode is a unique and shorter installment with insights and reflections rather than our normal interview format. The focus is on exploring the concept of risk aversion within the insurance industry and comparing it to the venture capital world.

Key Topics Discussed:

1. Risk Aversion in Insurance:I see a paradox of risk aversion in an industry that essentially deals with buying and managing risk. Despite being in the business of risk, the insurance industry tends to be conservative and slow to change.
2. Comparison with Venture Capital:A comparison is drawn between underwriters and venture capitalists, highlighting how both evaluate businesses but from different perspectives. While venture capitalists have a capped downside and potentially unlimited upside, underwriters face a capped upside and potentially unlimited downside.
3. Analogies and Insights:I compare this to the Netflix show "Stranger Things" to describe the contrasting worlds of insurance and venture capital, likening them to the "Upside Down" and the real world.
4. Economic Perspectives:Discussion on the economic frameworks within which underwriters and venture capitalists operate, emphasizing the differences in risk and reward dynamics.
5. Personal Reflections:The episode includes personal anecdotes and reflections on the nature of risk, decision-making, and the psychological aspects of dealing with uncertainty.

Conclusion: The episode concludes with a call to embrace conversations about risk and change, encouraging listeners to prepare for and adapt to new challenges in their professional environments.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Info

Charlie Wendland is the Chief Claims Officer at Branch, a modern reciprocal exchange reinventing bundled home and auto insurance. With over two decades of experience at Progressive, Travelers, and National Interstate, Charlie has built and scaled high-performing claims teams that blend technology with exceptional customer care. He holds both an MBA and bachelor's degree from Cleveland State University, plus multiple industry designations, and he currently serves on the board of OACTA. At Branch, Charlie built a digitally enabled claims organization from scratch and continues to pioneer innovations that improve outcomes and customer experiences. He's passionate about modernizing insurance, uncovering hidden value, and mentoring the next generation of claims professionals.

Episode Highlights

1. AI in Claims Processing: The discussion emphasizes the use of AI at Branch to streamline the claims process, particularly through voice AI and electronic first notice of loss. This has led to over 70% of claims being reported through these technologies, enhancing efficiency and customer satisfaction.
2. Empathy in AI: Charlie raised the concern about the ability of AI to replicate human empathy. He notes that the AI has been surprisingly effective in issuing empathetic responses, which is crucial for maintaining customer satisfaction.
3. Technological Integration: Branch has integrated AI in various administrative tasks, such as document generation (with a solution from Kyber) and mail handling, which frees up human resources for more complex tasks. This has resulted in significant time savings and increased staff capacity.
4. Future Prospects: Looking ahead, Charlie see the potential for AI to overlay on top of new data, particularly in Auto claims, where newer car models capture extensive data. This could shift the focus from claims investigation to claims confirmation.
5. Human-AI Collaboration: Charlie underscores the importance of human oversight in AI-driven processes, ensuring accuracy and maintaining a human touch in customer interactions, as well as the need to be mindful of the impact of change on your staff. Given the speed of change Branch has lived, they've found this to be incredibly important.

Overall, Charlie gave a comprehensive view of how AI is transforming the insurance industry, focusing on efficiency, customer experience, and the balance between technology and human interaction.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Info

Reid Holzworth leads Ivans' strategic direction. He is a prominent insurance industry leader with extensive insurance experience in both broker and insurer distribution environments. Reid began as an independent agent, frustrated that the products on the market didn't fit well with his business model. So he founded and became CEO of TechCanary, an InsurTech leader on the Salesforce platform  that Applied Systems acquired in 2019. TechCanary built an innovative set of insurance solutions on the Salesforce platform to create choice and flexibility for agencies who prefer Salesforce.com, which has since been incorporated in Applied's portfolio under the name Applied Epic for Salesforce.

Episode Highlights

Introduction

• The video begins with a discussion about Reid's journey into the insurance industry, starting on the broker side and eventually managing an agency. Reid shares insights into their experience of franchising an agency and building a system on the Salesforce platform.

Key Topics Discussed

1. Building TechCanary

   • Reid founded TechCanary, a technology company that became the leading insurance solution on the Salesforce platform. They discuss the partnership with Salesforce and the expansion into working with MGAs, carriers, and wholesalers.

2. The Role of Ivans

   • Ivans is highlighted as a crucial player in connecting carriers and agencies. Reid explains how Ivans transitioned from a nonprofit to a for-profit entity and its acquisition by Applied Systems.

3. Technology and Innovation in Insurance

   • The conversation touches on the integration of third-party data sources and the importance of operational efficiency. Reid emphasizes the need for continuous innovation and adaptation in the insurance industry.

4. Challenges and Opportunities

   • Reid discusses the challenges faced in the insurance industry, such as the need for better data management and the potential of AI and other technologies to transform business operations.

   • He does not see AI replacing agents and brokers because of the way relationships are so critical to the work they do, but does see areas will it will have great impact, especially for work that has shifted to lower cost locations globally.

5. Future Outlook

   • The video concludes with a forward-looking perspective on the insurance industry, highlighting the importance of evolving and iterating on business models to stay competitive.

Conclusion

• Reid shares his unique vantage point in the industry, bridging the gap between traditional agency operations and modern technological advancements. The discussion underscores the dynamic nature of the insurance industry and the continuous need for innovation.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Just a quick note that we are taking a short break for a couple of weeks to enjoy the summer, but the rest of Season 7 will be back soon!

In the meantime, this is a great opportunity to catch up on the back catalogue of the show, or get The Future of Insurance books from Audible to keep listening to inspiring stories of how companies in the insurance industry are overcoming challenges, innovating and evolving.

Just visit www.future-of-insurance.com or search for The Future of Insurance on Audible or Amazon.

Episode Info

Mary Boyd is a seasoned senior executive with over 30 years of experience leading businesses through transformative phases in their history that span invention, renovation, integration and rebuilding. Beyond her reputation for building, revitalizing, and integrating businesses, Mary has a proven track record of successfully translating strategic vision into reality. Her career is distinguished by spearheading large-scale operational, technological, and team transformations, driving significant growth and innovation across organizations. Mary's success lies in her ability to blend innovation with an agile approach, excelling at both seeing the big picture and identifying strategic opportunities in the finer details.

Since 2006, Mary has held CEO, President and division leadership roles, consistently improving net income by optimizing channel economics, fostering best-in-class partnerships, building high-performance teams, and advancing operational excellence. 

Mary currently serves as Chief Executive Officer of Hiscox USA, leading the business through its next phase of growth and commitment to supporting the small business landscape. In her role, Mary oversees the financial operations of Hiscox USA's nearly $1 billion commercial property and casualty business. She collaborates closely with her teams to drive near-term profitable growth while implementing a strategic vision that will markedly expand their reach to more of America's entrepreneurs.

Mary joined Hiscox from Plymouth Rock Assurance Corporation, where she served as President and CEO of their Independent Agency Group, overseeing personal insurance and commercial auto businesses. Before that, she led Hartford's personal lines Direct-to-Consumer and Agency channels, following 15 years in high-net-worth personal lines. Mary began her insurance career at Chubb as an actuarial trainee, progressing through roles in Product and Pricing. She ultimately launched the Predictive Analytics practice for Chubb's Personal Lines division and later spent five years at ACE (now Chubb), where she served as President of their Private Risk Services division. 

Mary earned her Bachelor of Arts degree in Applied Mathematics and Economics from Rutgers University. As a coach of youth sports, ambitious professionals, and entrepreneurs 

Episode Highlights

Introduction and Background

• Mary shares her experience and background in the insurance industry, highlighting her 30-year career and her role at Hiscox USA.

• Hiscox USA, part of a long-standing London-based company, started its operations in the US in 2006.

Business Model and Growth

• Hiscox USA has transformed the small commercial business sector by offering online binding and digital partnerships, expanding its business to nearly a billion dollars.

• The company operates as an omnichannel business, engaging in direct sales, digital partnerships, and wholesale brokerage.

Challenges and Opportunities

• The conversation touches on the challenges small business owners face, such as being underinsured, and how Hiscox aims to support them through education and tailored insurance solutions.

• The company is focused on being a leading insurer for entrepreneurs, emphasizing the need for holistic support beyond just sales.

Innovation

• The discussion emphasizes the importance of AI and advanced tools in improving underwriting and efficiency across the insurance value chain.

• Hiscox has partnered with Google to leverage AI for better underwriting and insights.

Future Outlook

• Mary discusses the future of Hiscox, highlighting the integration of data and analytics to enhance product offerings and maintain competitivenes.

• The company aims to continue its growth by being a better partner and protector for businesses, focusing on insights and protection rather than just speed.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.