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The Insurance Startup Funding Vacuum

Posted On June 13, 2025June 13, 2025 By Ian5 Comments

There is always outsized interest in insurance startups, whether they be new reinsurers, the latest “insuretech”, a new MGA, etc. But one topic that tends to go overlooked is that there is a big impediment today to getting a startup off the ground – financing. Historically, new insurers were funded Continue Reading

Category: Entries

Where Can Insurers Innovate? Teen Drivers!

Posted On September 21, 2023September 21, 2023 By Ian

Editor’s Note: If you missed last week’s post, there is still availability to have us help you shop for home or auto insurance. We had a number of people sign up last week, but we’re caught up now and can accept more. Sign up here. With all the energy spent Continue Reading

Category: Entries

Are You Sure I Wrote This Blog?

Posted On December 7, 2022December 8, 2022 By Ian

You’ve all probably heard the phrase when a journalists “mails in” a column. Well, today, I am going one better. I am auto generating a post. That’s right, if you’re not familiar with Open AI‘s new chatbot tool, ChatGPT, you should be. It has the power to change insurance customer Continue Reading

Category: Entries

Fiat Money, Gold, Beanie Babies, and Beeple: What is Value and do NFTs Have Any?

Posted On March 17, 2021March 17, 2021 By Ian4 Comments

Note: If you’re only here for the NCAA Bracket advice, you can skip to the end. 😉 Yeah, you’re all expecting I’m going to tell you NFTs are worthless, aren’t you? I mean they mostly are, but before we get to that, I’d like to have a broader discussion of Continue Reading

Category: Best Of/Entries

How to Evaluate CAC: An Alternate Framework

Posted On December 22, 2020April 28, 2021 By Ian

If that title sounds familiar, yeah, I cribbed it from the recent TAM piece. Today, we’ll explore how CAC (cost of acquiring customers) is misused. Traditionally, the cost of acquiring a customer for an insurance company was pretty easy to measure. You paid a commission to the producing agent at Continue Reading

Category: Entries

Metromile: The Palm Pilot of Insuretech

Posted On December 7, 2020December 15, 2020 By Ian1 Comment

Metromile, the pay by the mile auto insurance carrier, has been in the news of late with its announcement to go public through a SPAC. Metromile is one of the original insuretech carrier models having launched in 2011 and going full stack in 2016. Missed Opportunity However, being the first Continue Reading

Category: Best Of/Entries

How to Evaluate TAM: An Alternate Framework

Posted On November 23, 2020December 22, 2020 By Ian1 Comment

In the startup world, the best way to become a Hare and get a high valuation is to talk up the giant total addressable market (TAM) of your product. Nothing gets a tech investor more excited than a company with bold plans to take over the world! Rational people often Continue Reading

Category: Best Of/Entries

Burn, Baby, Burn

Posted On October 19, 2020August 12, 2021 By Ian

No, this isn’t about the California wildfires. It’s about the Root IPO. Confused? Don’t worry, keep reading. I explain it all. So I was going to write a detailed page by page guide to the Root S-1 like I did for Lemonade, but two things got in the way. First, Continue Reading

Category: Best Of/Entries

The Insuretech Tortoise vs. The Insuretech Hare

Posted On July 27, 2020August 25, 2020 By Ian

I know what you’re all thinking. Here comes another version of all the reasons the overhyped insuretech names aren’t going to make it. Not so fast (said the tortoise)! Today, I will make the case for how the seemingly misguided strategy of the hare may be the better path to Continue Reading

Category: Entries

Quantum Computing: The True Disruption Threat

Posted On January 10, 2020January 10, 2020 By Ian

Add quantum computing to the futuristic list of things insurance CEOs should lose sleep over. All that money you spent updating your systems? Useless. All your “proprietary AI” underwriting? Outdated. All the security practices your cyber insured use? Vulnerable. Stop worrying about insuretechs or even self-driving cars. The real threat Continue Reading

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