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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

Category: Entries

Ian’s Brief #3: Year In Review

Posted On January 1, 2020January 7, 2020 By Ian

Yes, it’s the obligatory end of the year post! Frankly, you could just read the “Best Of” page instead, but if you want a somewhat longer version, here you go… I’ve grouped together the various themes that tended to repeat over the year and many of which you can expect Continue Reading

Category: Entries

Insuretech: PUREly Overvalued

Posted On October 3, 2019October 3, 2019 By Ian

Big news for insuretech today and it’s not good. PURE sold itself for $3.1B to Tokio Marine. This is a great outcome for PURE and they are to be congratulated on building such a successful business in a relatively short time (11 years). However, this is pretty terrible news for Continue Reading

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