EP 38 – Innovative Approaches to Real Estate Insurance: Transparency, Technology, and Partnerships – Aaron Letzeiser – co-Founder of Obie Insurance


Michael Waitze worked in Global Finance for more than 20 years, employed by firms like Citigroup, Morgan Stanley and Goldman Sachs, primarily in Tokyo.  Michael lived and worked in Tokyo from February 1990 until December 2011.  Michael always maintained a particular focus on how technology could be used to make businesses more efficient and to drive P/L growth. Michael is a leader in the digital media space, building one of the biggest and fastest-growing podcast listener bases in the region.  His AsiaTechPodcast.com show has listeners in more than 130 countries and his company, Michael Waitze Media produces some of Asia’s most popular podcasts.

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.

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In this episode of InsurTech Amplified, ⁠Aaron Letzeiser⁠, co-founder and COO of ⁠Obie Insurance⁠, shared his journey from a non-traditional insurance background to transforming the insurance process for real estate investors. Aaron and his brother Ryan identified a significant problem in the industry: the lack of transparency and control in obtaining insurance for real estate investments. By leveraging their combined expertise in business and real estate, they created a solution that digitizes the underwriting process, provides instant quotes, and empowers customers to make informed decisions. Aaron’s story underscores the importance of empathy, curiosity, and leveraging existing skills to solve real-world problems.

Aaron also emphasized the value of good partnerships and the impact of embedded insurance. By partnering with strict lenders and integrating the insurance purchasing process into real estate transaction platforms, Obie Insurance ensures compliance and eliminates delays. This innovative approach, called Embedded 2.0, benefits both lenders and buyers, simplifying the insurance process and reducing administrative burdens. Aaron’s experience highlights how technology can transform traditional industries, making processes more efficient and user-friendly, and offering valuable lessons for entrepreneurs and industry professionals alike.

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