Aaron Letzeiser

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.

what if everything goes right

@fortworthchris @jamesbeshara 💯💯💯 and I can attest that @jamesbeshara lives up to that!

I keep coming back to something @jamesbeshara said about angel investing. The bar to become a founder's favorite investor is much lower than people think. James has invested across 150+ companies and reviews around 1,700 deals a year. His take: most investors show up like they're auditing a 10-K. For the founder, it's the 50th non-encouraging conversation of their day. In this clip from this week's episode, James on why a dose of encouragement is the difference between a founder quitting and not quitting.

@MoFromYYZ I really need someone to make it make sense 🤦‍♂️

Someone explain this to me, asking for a fellow insurtech founder friend

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

MOST PEOPLE: 6-12 months escalate → discuss → roadmap “let’s circle back” HEAT SEEKER: 1-2 days isolate → fix → ship “done”

@justindross @NateSmoyer Ha well that’s true! @NateSmoyer Let’s put it this way, if @justindross was smart enough to invest in Obie, he’s smart enough to know insurance could use some help! Brokerage isn’t going away with AI, but you can optimize the hell out of day to day to drive real material value

@NateSmoyer @letzeiser I was smart enough to invest in Obie so Aaron can’t call me dumb in public

Insurance Brokerage is the biggest opportunity in AI Autopilot

@patrickc @patrickc grab some brce.shop laces and they’ll never come undone. They just aired on @ABCSharkTank

There are two ways of tying a standard shoelace knot, based on the relative handedness of the two half-knots, and the correct one basically never comes undone. I assume everyone else knows this and has been gently pitying me as I ignominiously retie my flailing laces, but sharing here just in case.

Chicago news feels like the Onion at this point

Yearly reminder if you are looking for the agent track at ITC it’s in the basement of the Luxor

Chicago has long deserved a serious startup hub. Introducing Density Collective.

@NateSmoyer @rohindhar @rohindhar definitely a tough market for CA and places like Lake Tahoe or Nevada. We're still open for business in those places at @obieinsurance along with others like @KIN, but the fires put a significant amount of pressure on the broader carrier market who have pulled back.

@rohindhar @letzeiser?

Anyone have more color on the homeowners insurance market in Lake Tahoe? California state plan (FAIR) the only option in CA? Nevada out of luck?

When he catches you doing things that don’t scale

@immad @mercury @sequoia @sparkcapital @MarathonMP @coatuemgmt @CRV @a16z Congrats @immad!

1/ Today, @Mercury announced a $300 million Series C in a mix of primary & secondary funding at a $3.5B valuation, led by @Sequoia, with participation from @sparkcapital, @MarathonMP, @coatuemgmt, @CRV, & @a16z. I’m deeply humbled by the growth we’ve experienced. 🧵

@yuris @immad Make something the people want!

@letzeiser @immad Shockingly they do. I got an instagram ad for it a week ago 😂 a.co/d/hhbv4ft

I am having another baby in a few months. What are cool gadgets that have been made in the last 5-10 years that are a must get? (I love baby gadgets)

@immad @yuris +1 for the slumber pod. The best invention for baby travel. Candidly, I also wish they made an adult version…

@yuris Thats cool. Does it compress way down?

@Ins_Brkr @jefffeldman Really profound way that article opened. The reality of what insurance is and does for society, but such a dichotomy with the unfortunate standard ugly and misunderstood public perception it has.

Shoutout to @jefffeldman for bringing to my attention. My takeaway: Over-regulation and socialization is the issue more than insurance... If private market insurance isn't offering coverage to a certain area because of risk and no government backed insurance exists, people just wouldn't live there (or take the risk themselves).

@RhadamisteX @yishan @beautifullybunk Ask the carrier (or your agent) what the AM Best rating is, which is their credit rating. Generally speaking, you’d want something rated A- or better.

I live in Southern California, 75 miles from the fires in Pacific Palisades, and I wasn't able to get home insurance earlier this year when I purchased a home. That's not exactly true - in most people's minds, you can only get insurance from California's "admitted carriers," which are the carriers who are regulated by the state. Those carriers agree to follow its rules on rates, policy terms, financial solvency and - most importantly - they participate in the state guarantee fund. If an admitted insurer goes bankrupt, policyholders can still get some help from the guarantee fund. My libertarian friends are fond of talking about how California's limitations on insurance carriers distort the market and artificially cap rates in an environment that logically dictates higher rates to cover higher risks. It turns out that even if none of the state's admitted carriers will (or can) insure you, you can still get insurance from other carriers - but then you receive none of the protections of the state guarantee fund or the legal limitations it puts on rates and policy terms. These non-admitted carriers (which you could call "unregulated" carriers - the formal name is "surplus line") effectively price home insurance to account for the real risks they are insuring against. So when the market is no longer regulated and insurance reflects real risks, how much do you end up paying? Well, it turns out that my premiums are only about ~2x that of the national average, but wildfire risk here is much higher than 2x the American average - it's MUCH higher. So what else are they doing to make the numbers work in this wildfire-prone area? Here's how they cover it: my policy has a massive $105,000 deductible on wildfire damage, per covered loss. This means it's a per-event deductible (rather than per-year deductible). If I ever have wildfire-related loss, I'll have to pay the first $105,000 out of pocket before insurance even takes a look. And then if it happens again later the same year, the deductible resets. Actuarially, this makes sense - the risk is still low that my home is destroyed completely - but there are plenty of instances where a nearby fire event does some damage worth up to $105,000 to the house, and insurance won't be paying for that. (If you're wondering why I'm here at all, it's because of proximity to medical services for long-covid, and because other than the fire situation, this is a pretty nice area) If our home is lost in a fire, I'll be out of pocket at least $105,000. I can cover it, but it'll hurt. This isn't true for most people. So, if you want to know what a true home insurance situation free of market-distorting regulations would look like in a climate-changing and bad-forest-management government world looks like, it's roughly this: in a disaster, everyone who loses their homes will be out at least $100,000. Possibly much more, if the insurance carrier goes bankrupt, because there will also be no pooled state guarantee. It's unclear to me whether after this disaster the state's backstop fund itself will even be solvent. If you have fire-related home insurance experiences or really just any other useful knowledge about insurance in this brave new world of ours, feel free to chime in! x.com/yishan/status/…

@yishan @beautifullybunk This isn't accurate. Oftentimes, the policy forms and contracts used in the "surplus" market are the exact same ISO standard forms of the "Admitted" market. What really matters here is the financial strength of the carrier -- admitted or not, and the reinsurance behind them.

Sadly, it's not "good" insurance. The reason it's called "surplus line" is because it refers to the "surplus" or "leftover" cases that other insurance carriers refused to take because it's not very profitable. I think in this case it's a Japanese company that is pooling risk with customers on both sides of the Pacific Ocean. I guess if you have international insurance carriers that can pool risk between Americans living in areas with irresponsible governance and non-Americans who live in more well-run places (and maybe there's an exchange rate strategy in it too?) you can make the numbers work if the Americans have a very high deductible.

@roshanpateI Been on @Rippling since 2019. Love it. Haven't found anything else that compares. No major issues from 2 to hundreds of employee accounts.

I'm convinced Rippling is a psyop. VCs hyping Parker Conrad, giving him $2B, calling it revolutionary Meanwhile, every screen takes 10 sec to load, clunky UI, missed payrolls, hiring errors. Nobody I know likes it. The product makes me want to lie down in the middle of traffic