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Uncontested Investing

Apr 2, 2024

Ryan Letzeiser is the CEO and co-founder of Obie Insurance, a company that provides insurance technology solutions for landlords in the single-family rental space. He has a background in real estate investing and that’s what got him into the insurance industry, to help real estate investors protect themselves and their assets better. 


Listen now to learn more about the story behind Obie Insurance, what they want to help real estate investors with, and what it takes to find success as an entrepreneur today! 


Key Talking Points of the Episode


00:00 Introduction

00:33 Who is Ryan Letzeiser? 

01:21 What got Ryan interested in the insurance space of real estate?

03:20 How does Ryan’s background in investing help him today?

05:10 What is the story behind Obie Insurance’s mantra?

06:48 What motivated Ryan to start Obie Insurance?

10:40 What do people need to focus on to become successful in life?

12:34 What is Ryan passionate about outside of real estate?

14:34 How important is Ryan’s team at Obie Insurance?

20:07 What are the things that can cause a deal to break down?

21:19 What factors make a deal successful?

22:47 What is the most important trait a leader should have?

25:25 What are the biggest challenges in innovating within the real estate space?

28:15 What trait of Obie Insurance is Ryan most proud of?

30:35 How did Ryan overcome his doubts as he got into entrepreneurship?

32:37 What is Ryan’s motivation to keep going?




“You have to find a way to be okay with making that pivot, knowing that that is the direction your customers are telling you to go, rather than you trying to force something out of that.”


“You can’t do it all on your own and you have to empower people to make decisions on your behalf and the only way you can do that is by finding top of the line talent.”


“We wanna make sure that we’re staying tried and true, that way we’re here for the long haul and not for a short range.”




Website: RCN Capital 


Instagram: RCN Capital


Website: REI INK