Episodes

Tuesday Jun 13, 2023
Tuesday Jun 13, 2023
Karn Saroya is CEO of Re, an on-chain, fully collateralized reinsurer. Re is the world’s first blockchain-powered reinsurer is building a decentralized global reinsurance market. The protocol provides investors with access to a massive and uncorrelated asset class: insurance premiums.
Re as a protocol will back insurance programs that support the risks that people, businesses and governments take to build better lives, and navigate an uncertain future.
Karn’s first company, Stylekick, was acquired by Shopify in 2015. Over the next seven years he scaled Cover.com into a national insurance platform. Karn holds a Bachelor of Commerce from Queen’s University with Distinction and a Master of Finance from the Massachusetts Institute of Technology, where he attended as a Fulbright Scholar. He is also a Y Combinator fellow and alumnus.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Tuesday Jun 06, 2023
Tuesday Jun 06, 2023
David Schapiro is Co-Founder at Planck AI based data analytics for insurance; Chairman of the Audit and Risk Committee at ManyPets - a provider of pet insurance in the UK, Sweden and US; a Director at Ahoy! Insurance - a recreational marine insurer; and advisor to Quantee - provider of AI-based dynamic insurance pricing; Herald - Digital infrastructure for commercial insurance; and Sayata - streamlining the quote-bind-issue process for commercial insurance brokers and carriers.
In today's episode, David talks about how to navigate the current markets, from an insurtech perspective and from an insurer's perspective. He discusses how insurtechs can dig in to focus on business results and cut costs to extend their runway, buying themselves time for higher valuations to return or negotiating a down round with existing shareholders to protect their investment.
He also contrasts that to the view of a large insurer, who have 80% retention, less than 100% combined ratio and have the wherewithal to be patient. The insurers in particular now face decisions as to whether now is the time to partner up or run M&A with insurtechs, and help redefine how their culture will feel on the other side of this market inflection.
A visionary and veteran CEO and Director with over 35 years’ experience with data analytics and Insurtech companies. David is well versed in leading and growing enterprise SaaS companies including Earnix and ClickSoftware (acquired by Salesforce $1.35B in 2019).
From 2006-2017 David was the CEO of Earnix, a provider of analytical SaaS for the Financial Services. David led Earnix from a small startup to becoming one of the leading analytical Insurtech players providing value to many of the top global financial institutions.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Tuesday May 30, 2023
Tuesday May 30, 2023
Bryan Falchuk is Founder of Insurance Evolution Partners, which advises carriers and their partners on how to navigate an evolving industry facing disruption and change. He is also the President & CEO of Insurance industry trade group, PLRB, that is dedicated to helping adjusters to make expert decisions on Property and Liability claims.
Bryan spent 20+ years in the insurance industry, including serving as Head of Claims for Hiscox USA and leading Growth for insurtech communications solution, Hi Marley. Bryan has also held leadership roles in corporate strategy, operations and distribution at carriers like Liberty Mutual and Beazley. He was a consultant in McKinsey & Company’s insurance practice and is on the advisory boards of several startups focused on the insurance industry.
Bryan is a best-selling author and public speaker, including several TEDx Talks. His best-selling book series, The Future of Insurance, shares case studies of legacy and startup carriers overcoming barriers to change.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Tuesday May 23, 2023
Tuesday May 23, 2023
Bob Sargent is President and Co-Founder with me of the Insurtech Association (ITA), a membership-based non-profit organization designed to support and represent all facets of the Insurtech ecosystem. Doug Ver Mulm is Volunteer Executive Director of the ITA.
In addition to his work with the ITA, Bob is also the CEO and Co-Founder of eSpecialty Insurance, a digital retail broker specializing in specialty lines insurance, and Doug is Co-Founder of a stealth startup serving the financial operations needs of the insurance industry - his second in Insurtech.
The InsurTech Association, launched in March 2023, carries the primary mission of supporting creators of technology. Open to any individual or organization with an interest in Insurtech, the founding board features a diverse group of founders who have successfully navigated the challenges of launching an Insurtech company. Four board members have experienced successful exits and continue to concentrate their efforts in the Insurtech space.
The ITA assists early-stage Insurtechs in navigating the inner workings of the insurance industry through various measures such as:
- Networking support
- Peer-to-peer dialogue
- Mentorship
- In-person and virtual educational events
- Community building
- General business acceleration
We encourage all followers of the Insurtech Leadership Podcast to join the ITA as members and to participate in upcoming events. For more information, please visit insurtechassociation.org/events. There are also sponsorship opportunities available for companies wishing to showcase their involvement in the industry to a startup audience, network with potential customers and partners, and expand their reach.
In addition to his roles at eSpecialty Insurance and the ITA, Bob is a strategic advisor to and an active investor in early-stage Insurtech companies. Previously he founded, built, and sold a wholesale insurance broker and underwriting manager specializing in Professional Liability Insurance (E&O, D&O, EPL & Cyber Risk), and was a Board member and President of NAPSLO (predecessor to WSIA), the specialty insurance trade association.
Doug co-founded Stable Insurance, a commercial auto MGA focused on the rideshare and carshare space. He also spent over five years as a corporate counsel at Mercer, focusing on data security initiatives and IP issues. Before law school, Doug was a financial analyst at several investment firms in Chicago.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Tuesday May 16, 2023
Tuesday May 16, 2023
Tom Wilde is CEO at Indico, an intelligent intake solution automating critical middle office workflows across insurance, banking, real estate and healthcare.
'Intelligent intake' at Indico means the starting point for insurers' most critical workflows including underwriting, claims and policy servicing. The common denominator is data culled from emails or other documents, taken from an unstructured format to feed core platforms and decision systems.
The original digital transformation started with the new customer-facing mobile device, but transitioned through the back office then into the middle office of insurance where business-critical decisions take place. Tom describes actuaries as the original data scientists, taking data and turning them into decisions. Their modern engines were designed to run on clean sets of data, but unfortunately the reality is that most data lives as unstructured and requires manual rework before it can be used.
Indico was early on understanding the impact of deep learning and large language models, and were the first to build a large language model that allows customers to customize their own machine learning models and solve unstructured data challenges.
Tom feels strongly that generative AI (eg. GPT4) can easily handle the context of insurance, because the depth of context-understanding enabled by trillions of parameters can understand any context a human can. There are however three main problems to commercially scaling insurance use cases today using GPT4: it is extremely computationally expensive, insurers' data is still sensitive and proprietary, and GPT4 essentially makes up an answer (lies) when it doesn't know one. Until these large language problems get solved, insurers will be held back from using generative AI in core processes.
Prior to joining Indico, Tom was the Chief Product Officer at Cxense, a data management provider and founder of Ramp, an enterprise video content management company. Tom worked at Fast Search, Miva Systems, and Lycos. He has an MBA in Entrepreneurial Management from Wharton.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Monday May 08, 2023
Monday May 08, 2023
Jason Berkowitz is currently CEO and Founder of ArrowUp, providing restaurant safety, compliance & leadership. ArrowUp helps restaurant owners reduce risk, satisfy compliance regulations and develop a culture of safety.
ArrowUp's Insurtech platform strengthens the relationship between the insured and insurer by utilizing tools to promote safe habits and capture data for enhanced underwriting, ultimately lowering risk and liability for insured restaurant owners.
He is addressing a market size of $16B in restaurant claim payouts annually, in a culture where lawsuits and union suits are commonplace. ArrowUp makes restaurants safer by providing leadership development, lowering turnover and building upon the culture within an organization to avoid unnecessary lawsuits. The results have been tremendous, with restaurants seeing 30-50% risk reduction based on OSHA standards for its customers.
Jason has opened over 50 restaurants, served as VP of Operations for Umami Burger, and COO and Partner for Tocaya Organica.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Tuesday May 02, 2023
Tuesday May 02, 2023

Tuesday Apr 25, 2023
Tuesday Apr 25, 2023
Blair Baldwin is CEO of Boundless Rider, a specialty MGA focused on product innovation for the motorcycle, power-sports, and e-bike markets.
Tribes of riders form an underserved market niche that includes motorcycles, UTVs, snowmobiles and new forms of mobility. Because these categories represent only 2-3% of an insurer's book, they have not introduced unique new customer personas of riders. Boundless created a new brand of customer experience, and added new features to the product. One example is an e-bikes optional endorsement linked to the Boundless mobile app that enables product discounts for usage.
Blair says that the digital self-serve experience is outdated and cumbersome. They put in features that encourage safety for example requiring the use of a helmet in order to be covered. His biggest surprise has been the collaboration with carriers to run this part of the business so that they can concentrate on larger lines of business.
Prior to launching Boundless Rider, Blair was the Co-founder/CEO of Quilt, a venture-backed insurtech that was acquired by MassMutual, where he later ran a product innovation studio. Blair started his adventures in insurtech as the Chief Marketing Officer for Goji, an early insurtech pioneer that raised over $100M in venture capital funding. He is a graduate of Harvard College and Harvard Business School.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Tuesday Apr 18, 2023
Tuesday Apr 18, 2023
Yaron Ben-Zvi was the CEO of Haven Technologies, a subsidiary of MassMutual and SaaS company in the life insurance space. Yaron led the company from inception through M&A, building a cloud-based end-to-end technology platform for life insurance.
As Founder and CEO of Haven Life, Yaron was also responsible for the strategy, vision, and management of one of the leading direct-to-consumer term life insurance businesses, whose mission was to make life insurance simple. Haven Life was recognized by US News, Investopedia, and many others as one of the best Term life insurance providers in the United States.
Previously, Yaron was also the Founder of Goalmine, an early robo-advisor that was acquired in 2012. Before that he was a Director at BuzzMetrics, where he joined as employee number ten, and helped grow the company’s key accounts until its exit to Nielsen.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Tuesday Apr 11, 2023
Tuesday Apr 11, 2023
James Felton Keith is Founder of Inclusion Score, an award-winning engineer and economist who was the first Black LGBTQ person to run for US Congress. James is currently an elected member of the New York Democratic Committee and is a frequent keynote at global venues like the United Nations, Future Tech Congress, Data Protection World Forum, and the World Pride Human Rights Forum. As an entrepreneur, he established the first international diversity & inclusion certification and the first insurance policy for a lack-of-inclusion based on an "inclusion score".
James has also founded multiple companies in Insurtech, Fintech and Adtech including Harlem Center, Slay TV, LGBT Chambers, and Accrue.com. James' focus economic inclusion, and how to get equity in the hands of the people who have increasingly less, while the world becomes more productive from their inputs.
James played an important role in forming the data industry by founding of Data Unions and Personal Data Week conferences. He also co-founded and edits the Ethics of Personal Data Collection series at Anthem Press. As an author, his bio-political philosophy, Inclusionism, is at the forefront of International Relations and Human Rights diplomacy. His career transitioned after founding Detroit’s LGBT Chamber of Commerce and "Pride Nights" at the four Big Box American sports franchises: NBA, NHL, MLB, & NFL.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.