Artwork for podcast Fintech Confidential
What Is The Next Big Thing in Insurance for Real Estate Investors?
Episode 5429th November 2023 • Fintech Confidential • DD3, Media
00:00:00 00:58:49

Share Episode


Aaron Letzeiser is the Co-founder and CEO of Obie, the game-changing insurance and risk management platform for real estate investors. He spills the beans on the fascinating journey of Obie, its groundbreaking mission, and the hurdles faced in its infancy. Discover how Obie leverages cutting-edge technology to revolutionize the insurance process, unveil transparency, and deliver tailor-made solutions. Brace yourself for the inside scoop on the power of specialization in the insurance industry, the hottest market trends, and the mind-blowing potential of large language models. Plus, Aaron drops some priceless advice for aspiring entrepreneurs and emphasizes the invaluable role of customer feedback.

Three things you can't afford to miss from this episode:

1️⃣ Unveiling the secret sauce behind Obie's game-changing insurance process!

2️⃣ The mind-blowing market trends that will reshape the insurance industry!

3️⃣ How large language models are set to revolutionize how we approach insurance!

Also, watch the entire episode on youtube.




Twitter -

LinkedIn -

Youtube -

Fintech Confidential









This episode of Fintech Confidential 1:1 is brought to you by Skyflow, the leading data privacy platform trusted by top financial institutions. Protect your customers' data with Skyflow's innovative solutions. Get started at

And don't forget to check out Chargebacks 911, the industry leader in chargeback management and prevention. Say goodbye to revenue loss and hello to seamless transactions with Chargebacks 911. Get started at

Time Stamps:

The frustrations with the insurance process (00:00:00)

In this interview, Aaron Letzeiser discusses how, during demos, people would forget about the tools and instead focus on discussing their frustrations with the insurance process. He sheds light on the common pain points faced by individuals when dealing with insurance and how his company, Obie, aims to address these frustrations.

The challenges faced in the early stages of the fintech journey (00:03:24)

Join Aaron Letzeiser as he shares the challenges faced in the early stages of their fintech journey. From relying on spreadsheets to the lack of technological innovation in the insurance industry, Lesser provides insights into the hurdles they had to overcome to bring their vision to life.

The evolution of Obie's mission (00:09:20)

Discover how Obie's mission has evolved over time as Aaron Letzeiser explains the company's journey. Initially wanting to solve every problem for real estate investors, Obie has now shifted its focus to doing one thing well. Learn about the reasons behind this strategic shift and the impact it has had on their business.

The challenges of building a fintech company (00:10:19)

Building a fintech company comes with its fair share of challenges. Aaron Letzeiser dives into the obstacles they faced in the early stages and emphasizes the importance of doing one thing well before expanding. Gain valuable insights into the lessons learned and the strategies employed to overcome these challenges.

The inefficiencies in the insurance process for real estate investors (00:11:37)

Join Aaron Letzeiser as he sheds light on the outdated and inefficient process of obtaining insurance for real estate investors. Learn how Obie's innovative technology eliminates the need for manual data entry and streamlines the insurance process, saving time and frustration for real estate investors.

Obie's mission and expansion in the insurance and risk management space (00:15:32)

Discover Obie's mission to make the insurance process even easier for customers as Aaron Letzeiser explains their expansion in the insurance and risk management space. Learn how Obie proactively integrates with different platforms to provide a seamless experience and enhance customer satisfaction.

The importance of underwriting data in insurance (00:19:49)

In this interview, Aaron Letzeiser highlights the importance of underwriting data in insurance. Discover how Obie utilizes underwriting data, such as cash flow and lender information, to assess risk in real estate investments. Gain insights into the role of data in making informed insurance decisions.

Ensuring transparency and protecting investor data (00:23:08)

Transparency and data protection are crucial in the insurance industry. Aaron Letzeiser explains how Obie maintains transparency in their services while protecting investor data. Discover how they anonymize necessary information and adhere to regulatory guidelines to ensure the security and privacy of their customers.

Speed, transparency, and risk management in insurance (00:24:42)

Speed, transparency, and risk management are key factors in the insurance industry. Join Aaron Letzeiser as he highlights the problems that OBI aims to solve, including providing fast and transparent services while effectively managing risk. Gain insights into how Obie's technology-driven solutions address these challenges.

The importance of specialization (00:29:43)

Specialization plays a vital role in the insurance space. Aaron Letzeiser discusses the value of finding specialists in the insurance industry and how it can lead to better understanding and results for customers. Discover the benefits of working with experts who have in-depth knowledge of specific insurance needs.

The ideal client for Obie (00:35:01)

Learn about the ideal clients for OBI as Aaron Letzeiser explains their target market. Discover why small to medium-sized residential real estate investors are the perfect fit for Obie's technology-driven solutions. Gain insights into how OBI can help these investors efficiently manage their properties.

Catering to accidental landlords (00:37:14)

Accidental landlords often face unique challenges when it comes to insurance. Join Aaron Letzeiser as he discusses how Obie caters to accidental landlords by providing education and guidance on the right insurance policies for their rental properties. Discover how OBI ensures these landlords have proper coverage and avoid potential issues.

The use of language models in insurance (00:39:23)

Explore the potential of language models, like GPT, to improve claims processing and policy interpretation in the insurance industry. Aaron Letzeiser discusses the benefits and applications of language models in enhancing efficiency and accuracy in insurance processes.

The role of data in insurance innovation (00:40:11)

Data plays a crucial role in driving innovation in the insurance industry. Join Aaron Letzeiser as he emphasizes the importance of leveraging data and trends to improve efficiency and bring about innovative solutions. Discover how Obie utilizes data to push the boundaries of insurance innovation.

The future of the insurance industry (00:43:34)

Discover how Obie is shaping the future of the insurance industry as Aaron Letzeiser shares their innovative approach. Learn how they use novel data to drive change while collaborating with existing carriers. Gain insights into the exciting possibilities that lie ahead for the insurance industry.

The vision of a more consumer-accessible insurance market (00:49:51)

Join Aaron Letzeiser as he discusses his vision of a more consumer-accessible insurance market. Discover the importance of transparency and consumer involvement in the insurance process. Gain insights into how Obie aims to make insurance more accessible and customer-centric.

Advice on narrowing focus as an entrepreneur (00:51:01)

Entrepreneurs often face the challenge of narrowing their focus. Aaron Letzeiser shares valuable advice on how entrepreneurs can identify the common thread and find their niche. Learn about the importance of talking to customers and identifying common themes to narrow your focus and drive success.

Pivoting towards customer needs (00:52:53)

Customer feedback can be a catalyst for change. Aaron Letzeiser shares an example of how customer feedback led Obie to pivot their focus towards addressing the pain points in the insurance process rather than building additional tools. Discover the power of listening to customers and adapting to their needs.

This is a Production of Diamond D3, Media


Aaron Letzeiser: Aaron Letzeiser is the Co-Founder & COO of Obie, a venture-backed insurance and risk management technology platform serving the 17 million real estate investors in the United States. Obie's digital quoting platform and instant rate options make it the easiest and most transparent way in the market today for investors to obtain coverage.

Prior to founding Obie, Aaron started and grew several successful companies that he’s seen to an exit. In addition to his work at Obie, he is an active real estate investor and a Venture Partner at the San Francisco-based venture capital group Pioneer Fund. Aaron graduated from Michigan State University and was named to the Forbes 30 Under 30 list.

Obie: Obie is an insurance technology company, hyper-focused on driving value for the modern real estate investor and the partners they work with every day. Whether you are an owner, lender, agent, or property manager, Obie’s mission is to build technology and insurance products that drive efficiency and fundamentally change the way insurance is bought and sold.

Tedd Huff: Tedd Huff is the Co-Founder of Voalyre, and the President & Founder of Diamond D3, a professional services consulting firm focused on global payments and marketing. He is also a video podcast host and producer of Fintech Confidential.

Over the past 24 years, he has contributed to FinTech startups as an Advisory Board Member, Co-Founder, and Chief Experience Officer, providing strategic and tactical direction for Global Payments OpenEdge, Heartland Payments, Nuvei, and TSYS, among others, focusing on growth while delivering innovation, process improvements and user experience-driven value to simplify the complexity of payments.

Diamond D3, Media: A media creation, management, and production company delivering engaging content globally