Aaron Letzeiser: Most Real Estate Investors Are Overpaying for Insurance

In this episode, I sit down with Aaron Letzeiser, co-founder of OB Insurance, to talk about one of the most overlooked (and overpaid) areas in real estate investing—insurance. If you’ve ever felt frustrated by rising premiums, confusing policies, or slow claims, this episode will be a game-changer.

Aaron shares why insurance is getting more expensive (especially in markets like Florida and Texas), what most investors get wrong about their coverage, and how OB is changing the way real estate pros manage risk. We dive into how OB uses tech to create fast, transparent quotes, the difference between replacement cost and actual cash value, and how to take back control of your costs—without sacrificing protection.

Episode Highlights

[0:00] – Introduction

[0:32] – Why insurance is one of the most misunderstood costs in real estate

[2:04] – Aaron’s background and how he went from private equity to co-founding OB

[4:20] – What OB Insurance does and how it’s built specifically for real estate investors

[7:39] – Why transparency and speed matter more than ever in today’s insurance market

[10:26] – Types of coverage OB offers: short-term flips, long-term rentals, and more

[13:14] – What’s really driving rising insurance costs—and how to mitigate them

[16:18] – How investors can reduce risk factors and potentially lower their premiums

[17:02] – The OB claims process and how it’s different from traditional carriers

[24:12] – Understanding replacement cost vs. actual cash value—and what you should choose

[28:55] – Final takeaways for protecting your portfolio while saving money

5 Key Takeaways

1. Insurance is often overpaid and under-optimized. Most investors don’t know how to evaluate policies, leaving money on the table.
2. OB puts investors in the driver’s seat. From fast digital quotes to customized coverage, the platform was built for real estate.
3. Your location is affecting your premium more than ever. Be proactive if you’re investing in storm-prone areas.
4. Know your valuation model. Replacement cost and actual cash value offer different protections—know which one you’re buying.
5. Claims don’t have to be painful. OB’s tech-forward claims process is designed to be fast, transparent, and easy to manage.

Links & Resources

• OB Insurance: https://www.obieinsurance.com
• Email Aaron: [e-mail]
• Learn more about Profit First for real estate investors: https://www.simplecfo.com

If this episode helped you rethink how you protect your real estate business, please rate, follow, and review the show. And don’t forget to share it with another investor who needs this kind of clarity.