building on the intersection of AI and commercial insurance, first hire @withshepherd

Joined January 2020
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Mar 26
Dispatch is awesome and reliable, just replaced ChatGPT in the dock with Claude app.
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Feb 19
4 years ago, before AI was everywhere, in the early days of Shepherd, @MoFromYYZ and I had to make a one-way door decision: buy a PAS or build it ourselves. Almost every insurtech founder we spoke to said the same thing: DON"T BUILD. We demoed nearly every major vendor. The price to value ratio wasn't there. So we built. That original PAS is now Shepherd’s internal operating system. Underwriting, pricing, workflows, risk signals all live in one core system. Most legacy carriers are still juggling 10 systems of record. Our entire company works from one. I’m writing about the decision and what it unlocked in detail here: shepherdinsurance.com/blog/b…
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Feb 18
The SWE/PM bottleneck is dying in front of our eyes ☠️ Old model: Idea → PRD → Mock → Implement → Ship. Now the constraint isn’t coordination. It’s judgment. I wrote more about this shift in my new blog post: danilk.substack.com/p/the-de…
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Feb 12
excellent piece on what it's like to deploy production-grade AI in the insurance domain recommend reading if you want to know how to bridge the gap between AI demos/eval benchmarks and outcomes for your customers shepherdinsurance.com/blog/y…
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Feb 12
Doing podcasts with your wifey is the most alpha move a man can make this year on X
Trigger warning: we love liberty, we love our kids (we have lots of them), we believe in God, and we're fighting for our country. oh, and we have a lot of successful friends doing the same. Am a lucky guy, and proud of my amazing wife; great to chat with her with @KatieMiller
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Jan 27
LLM training and inference needs are skyrocketing — and so is energy demand across the United States. Proud to share that Shepherd will be helping insure the next wave of energy infrastructure powering our Great Country 🇺🇸 shepherdinsurance.com/blog/s…
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Jan 15
long whole milk
Make Whole Milk Great Again.🥛
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Jan 15
this
Silicon Valley is already losing the wealth tax debate by arguing that “founders would lose control” or “the golden goose would be gone” or “cut down fraud first.” They’ve lost frame. No one outside of a tiny population in the SF Bay Area cares about “founders.” No one cares about the golden goose when they’re not directly making money from it. In fact, that’s the whole point, they want to get money from the golden goose. If you’re saying eliminate fraud first, you’re basically agreeing that if there wasn’t fraud, seizing private property is justifiable in a cost-benefit analysis. No one cares that “millionaires are next!” These are all losing arguments. A wealth tax is anti-American and stands against everything this country was built on. It is downright evil. It fundamentally destroys this country’s competitive advantage and we will be an irrelevant fallen power in the future, just like so many before us. But once you accept the other side’s frame and try to “rationally” argue against it, you’re losing. Fight fire with fire, not irrelevancies that most of the country doesn’t care about. People care about the destruction of the American experiment. Make that case, not a weak pushback that accepts the other side’s frame.
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Danil retweeted
Great read on building an AI-services company. I work with two (@hanoverpark and @RivetTax) and Danil's lessons apply for anyone looking to build a generational company with this time of business model.
Jan 13
Just launched my blog: The Power of And. danilk.substack.com/p/the-po… It is about building AI-native services in the real world where software meets regulation, capital, compliance, and operations. First post: why cross-functional excellence is the real AI moat. And you can read a rant version of it in the X article below. If you are building AI that touches the spreadsheet economy (legal, consulting, insurance), this is for you.
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Jan 13
Very bullish on this, excited to see more folks building in the space. Insurance should be an efficient market, customers should not be paying 30% for procuring an insurance policy. Can you imagine paying 1/3 of every transaction to Amex/Visa when swiping a card?
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Jan 13
Just launched my blog: The Power of And. danilk.substack.com/p/the-po… It is about building AI-native services in the real world where software meets regulation, capital, compliance, and operations. First post: why cross-functional excellence is the real AI moat. And you can read a rant version of it in the X article below. If you are building AI that touches the spreadsheet economy (legal, consulting, insurance), this is for you.

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22 Dec 2025
ChatGPT Year in Review replaces Spotify's this year
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10 Nov 2025
Agreed on all
8 Nov 2025
Call me old-fashioned, but I don't think getting and renovating a big office is a good use of time and money when you're extremely pre-PMF. Spending money is not success. Making money is. This was our office when we were half the size and 10x the revenue as this team. Our main perk was all-you-can-drink horse electrolytes (3rd pic). Rent was $6k. I also wouldn't delude myself into thinking that the fancy office is a recruiting tool. You don't want people joining you because of your sauna and surfboards. You want those who do because of your mission, your team, your traction. Having a fancy office gives everyone the false impression that you've "made it." My intention is the exact opposite: we haven't made it, we can die any moment, and we better work our asses off (not go surfing of sauna'ing) if we want to increase our odds of survival.
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29 Oct 2025
Thank you @cursor_ai for a great update, can it come with a more powerful laptop next time? 11 GB RAM, really? P.S. I am running Pro M4 with 16gb RAM.
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Danil retweeted
27 Dec 2024
This is the right position for those who want America to win. For those who want America to lose for their own personal gain, I have no respect. Zero.
Elon’s stance on immigration has been pretty consistent. Here’s him outlining it in 2023:
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7 Dec 2024
Congrats to our landlord at Shepherd! Pragmatism wins.
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Danil retweeted
Need some urgent help from @stripe @stripesupport @patrickc to resolve an issue and ensure our workers can get paid this weekend! If anyone can help us escalate with their team internally, would be huge 🙏🏽
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