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Why Root Needs To Issue Equity Today

Posted On April 10, 2024April 10, 2024 By Ian

For those who remember the tortoise vs. hare insuretech thesis, when did it make sense to be a hare? When your stock was overvalued and thus capital was cheap. You could raise equity as a competitive advantage to allow you to sustain large operating losses while you built out your Continue Reading

Category: Entries

Observations From The Insuretech Multiverse

Posted On September 6, 2023September 6, 2023 By Ian2 Comments

As news continues to get worse for incumbent insuretechs, it made me wonder if there is an alternative universe where startup insurers behaved more thoughtfully and rationally and achieved great success. Luckily, with a little help from some failed startup CTOs from our Earth, I’ve been able to open a Continue Reading

Category: Best Of/Entries

The First Draft of Hippo’s Obituary

Posted On August 24, 2023September 1, 2023 By Ian4 Comments

You ever wonder how after someone famous dies the news sites instantly have an obituary written? You probably know it’s because there are writers who compose these ahead of time while the subject is still alive. Maybe not the most polite thing to do but understandably necessary. In that vein, Continue Reading

Category: Best Of/Entries

Why VCs Keep Getting Insuretech Wrong

Posted On June 22, 2023September 5, 2023 By Ian3 Comments

How’s that for biting the hand I am asking for food? But I think any investors reading this will hopefully realize this is valuable advice that will be helpful to them. After spending a few years now comparing how I look at investing in insuring companies and how VCs look Continue Reading

Category: Entries

Is Embedded Insurance Bad For Insurers?

Posted On May 25, 2023May 25, 2023 By Ian

Last week I wrote about the premise of embedded insurance and why I feel, in most cases, it does not benefit the consumer. This week I am back to write how it’s also a bad idea for the insurers! Why? Because you are doomed to be a commodity provider. Dumb Continue Reading

Category: Entries

Is Embedded Insurance Bad For Consumers?

Posted On May 18, 2023May 18, 2023 By Ian3 Comments

I’ve been meaning to write about embedded insurance for some time. Embedded insurance is everything that is wrong with the startup approach to insurance. Rather than look at things from the consumer’s perspective and ask how it helps them, embedded looks at things from the insurer’s perspective: how can we Continue Reading

Category: Entries

New Year’s Flashback: Revisiting Past Predictions

Posted On January 5, 2023January 5, 2023 By Ian

Last week, I looked back at some of 2022’s predictions, but this blog has made a lot of successful predictions over the years. In fact, I think it’s one of the core strengths of what I do here. I sometimes forget most people reading probably have not been around for Continue Reading

Category: Best Of/Entries

The Reinsurer’s Veto Is Here: What Higher Cat Reinsurance Prices Mean For MGAs

Posted On November 7, 2022August 22, 2023 By Ian1 Comment

New Fair Use Policy: I’ve always operated under the principle that this blog is meant to enlighten others and thus, if people want to share it, they are more than welcome to do so. I assumed anyone reproducing it in a professional context would be, well, professional enough to cite Continue Reading

Category: Entries

The Founder’s Dilemma And Its Role In Insuretech Layoffs

Posted On July 21, 2022July 21, 2022 By Ian8 Comments

Long ago, I wrote about economic rents in insurance. It was actually my first insuretech post. I have to say it has aged very well. If you weren’t a reader back then, I humbly suggest, you go back and check it out. Today, I want to expand on it. Because Continue Reading

Category: Best Of/Entries

Why Insuretechs Should Be Scared of the Reinsurer’s Veto

Posted On June 21, 2022June 28, 2022 By Ian

Informed Tip of the Week: Informed was designed specifically to avoid the Reinsurer’s Veto. It’s one of the many reasons we’ve chosen to start as an independent agent. Cash Burn Is So 2020 To keep with the recent theme of calling out the obvious, it’s time to talk about the Continue Reading

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