Fixing insurance for real estate investors @obieinsurance (acq. $BWIN). YC S19. Spartan.

Joined July 2014
16 Photos and videos
Aaron Letzeiser retweeted
I found the SpaceX IPO surprisingly emotional today. It reminded me of why I came to the US as an 18-year-old. Even then, I knew that I wanted to build stuff, and that the place to do it was America. There was no second option in the world. The concept of American exceptionalism is nothing new, but I have come to appreciate the culture that justifies it. SpaceX is yet another case in point. America’s risk-taking culture celebrates wild successes while embracing the legitimacy of hard-earned failure. American culture doesn’t celebrate inherited wealth, nor does it frown upon inherited poverty. It doesn’t seek to create equal outcomes, but rather equal opportunity. It is not immediately obvious that this is unique in the world. Truly unique. I’m Canadian, and I love many aspects of Canadian culture, but Canadian culture does not offer people the same environment in which to take risks. I write this because I was dismayed to see US politicians complaining of the extreme wealth created by the SpaceX IPO. Say what you will about wealth inequality, or a single man’s politics, but don’t tell me that immense wealth creation in America is bad. Do not tell me you’d rather SpaceX not exist, exactly as it does. That you’d rather this company exist in some other country or culture. Thankfully, despite today’s politics, SpaceX could not have been a Chinese company, or a Canadian one, or a French one. It could only ever have been an American one. If nationalism is pride in your birthplace, then it’s merely tribalism, which serves to divide us. But if it’s pride in your culture, a culture that lets people achieve incredible things like this, then under those terms I am a nationalist. I want to protect and enhance our culture of risk-taking, of celebrating wins, and of celebrating failures along the way. I think it is amazing that America created a trillionaire out of a risk-taking immigrant. It is absolutely fucking absurd, of course, but isn’t that the point? SpaceX is not a reason to be pissed off; it’s a reason for every person in the world who wants to build stuff to see themselves as American, no matter where in the world they live. p.s. — this is entirely from my brain, with AI used only for fixing typos and grammar. :^)
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Aaron Letzeiser retweeted
For many startups, fundraising is a grind filled with rejections and occasional humiliations. It can be even more demoralizing when you think you're the only one struggling. You aren't.
I've posted this before but it's always motivating to me to go back and look. Our first attempt to raise money for B&W Moxie.
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Aaron Letzeiser retweeted
what if everything goes right
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Aaron Letzeiser retweeted
This is by far the best interview I have ever seen with someone who holds or held elective office Every school should show this to the students @BenSasse - exactly what we need
Every American should watch every second of this video. Thank you, @BenSasse.
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Aaron Letzeiser retweeted
MOST PEOPLE: 6-12 months escalate → discuss → roadmap “let’s circle back” HEAT SEEKER: 1-2 days isolate → fix → ship “done”
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Aaron Letzeiser retweeted
Chicago news feels like the Onion at this point
Chicago Approves 19% Hotel Tax To Fund Tourism Push zerohedge.com/markets/chicag…
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Aaron Letzeiser retweeted
Chicago has long deserved a serious startup hub. Introducing Density Collective.
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Aaron Letzeiser retweeted
26 Mar 2025
When he catches you doing things that don’t scale
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Aaron Letzeiser retweeted
We are less than a week out from @ChiTechIRL's event next week. Let me know if you can make it!
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Aaron Letzeiser retweeted
22 Mar 2024
Insurance will be the biggest story in real estate 2024-2034
The home insurance shock hitting California is getting worse State Farm will non-renew approximately 30k home insurance policies & 42k apartment policies State Farm already stopped writing new CA policies last year raised rates by average of 20% sfchronicle.com/california/a…
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Aaron Letzeiser retweeted
2 Mar 2024
A strong pitch is simple statements said in a sequential way that doesn't require leaps of faith, but when taken together add up to a very big audacious idea.
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Aaron Letzeiser retweeted
1 Mar 2024
Took me a long time to realize solutions aren't always what people want. Sometimes they just want someone to empathize with them.
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Aaron Letzeiser retweeted
If you deeply care about Chicago, as I do, and want to see our city and people grow and prosper, then I highly encourage you to both thoroughly read this entire thread and follow its author @StuLoren Stuart very clearly and articulately states the great problems we’re facing and paints the obvious picture of how we solve our overall crisis, through recruiting and retaining the top businesses and entrepreneurs by improving public safety, reducing taxes, and stabilizing fiscal health Nothing here is complicated, it’s all completely obvious if you think about it logically Now all we need is serious leadership in our local government to actually do the hard work and save our city from a death spiral that we’re potentially already experiencing
2 Feb 2024
1/25 Some thoughts on fixing Chicago stuff: The past several years the @MilkenInstitute has put out a report on the best performing cities in the US, looking at economic performance across various measures: labor market, tech, access to opportunites, etc. milkeninstitute.org/best-per…
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Aaron Letzeiser retweeted
1 Jan 2024
🎉 Everyone at Obie wishes you a safe and happy New Year! We are closed today in observance of the holiday, but will be back tomorrow to kick off 2024.
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Aaron Letzeiser retweeted
It's much easier to build when you're optimistic. In this episode, @daltonc and @mwseibel discuss the best ways for founders and aspiring founders to think about weighing optimism and pessimism in their day-to-day. ▶️ youtu.be/vhXdUXmmhb4
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Thanks @DangremondSam! Glad it worked out for you!
I'd like to give a shout out to @obieinsurance - just moved four SFH policies over to them. Saved almost 30% in yearly premiums, while *also* going from basic to all-peril coverage! obieinsurance.com/landlord-i…
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Aaron Letzeiser retweeted
Everyone needs to watch this video in its entirety, and then send it to your friends and family immediately
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💯💯💯
When founders are raising a Series A, they typically prioritize getting the best economic terms first, and treat who sits on their board as a second priority. They should do the reverse.
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Aaron Letzeiser retweeted
At YC, we work with founders throughout the life of their startup and beyond, to build the world-changing companies of the future. And we'd love to work with you. The deadline to apply for YC W24 is this Friday, Oct 13 at 8pm PDT — apply today at ycombinator.com/apply.
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Thanks to TRAC and @BusinessInsider for highlighting Obie on this list of future tech unicorns!
16 Aug 2023
We’re excited to be named one of 30 tech startups most likely to become tech’s next unicorn🦄! Check out the extended list on @BusinessInsider shorturl.at/fryEX
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