founder of LedgerUp - building AI agents that do billing and revenue ops for B2B companies | ledgerup.ai

Joined May 2023
57 Photos and videos
i was at my best friend’s wedding in Virginia Beach this weekend. insane how big of bubble sf is
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i'm telling you, every company will be forced to go to open source
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Bailey Spell retweeted
this is @davidhaooo . these photos are from two different days. same position, same RGB split keyboard, same glasses. at some point i stopped asking if he wanted a desk.
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this is @davidhaooo . these photos are from two different days. same position, same RGB split keyboard, same glasses. at some point i stopped asking if he wanted a desk.
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something big coming
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the more and more i build in the ai space, the way we use applications is going to be so different. more than it already is and we are so ealry
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it's crazy that start ups even work
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testing out our new canvas feature. who new revenue and checkers had so much in common!
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Bailey Spell retweeted
this "right way to run a company" debate is two people in great shape arguing about whose diet and workout routine everyone else should do
Maybe that culture is fine for you at linear, and it looks like it’s working great for you! You’ve created something worth over a billion dollars in 7 short years, that’s something very few people on the planet have done before. But sometimes there are big problems that need solving, and there is more creative thinking, not less, that happens with contact with the big problems. In our case, creating the financial operating system that owns the creation, transfer, financing, and investment of risk, using AI to automate the paperwork of the most regulated entities to make every business and person a little more profitable, waste a lot less time, and be more protected, is a big problem. Maybe there were super geniuses at the Manhattan Project working 1 day per week like zen masters. I doubt it though, because if you’re obsessed with a problem, you work hard. Nowhere did I or do I glorify lack of sleep (I always think sleeping right and exercise are very important), and different people have different visions, cadences, and ways they want to run their companies. And that’s ok, but you attacking our style based upon sound bites when we are solving a really important problem, by market sizing probably the biggest problem large language models can solve, isn’t it.
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claude is still really bad at dates
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team gets branded backpacks and needs to wear them while sitting
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twitter is the biggest bubble. my brother has no idea what Claude is
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Bailey Spell retweeted
Excellent reporting by @MTemkin at @TechCrunch on how AI companies are inflating revenue by reporting CARR as ARR. Please retweet so that we can get back to reality and permanently kill CARR as a valuation anchor. Delusion is not good for anyone. "One VC told TechCrunch that he has seen companies where CARR is 70% higher than ARR, even though a significant chunk of that contracted revenue will never actually materialize." “Investors can’t call it out,” a VC told TechCrunch. “Everyone has a company monetizing CARR as ARR.” The biggest thing that has surprised me since my tweet went viral was the amount of nervous, sheepish laughter from VCs on the topic: "Haha... Oh, I'm not sure if it's that big a deal 🙂" While other VCs say privately: "We see this constantly and it's becoming a serious problem." techcrunch.com/2026/05/22/ho…
It’s time to expose a huge scam in AI startups: Contracted ARR The reason many AI startups are crushing revenue records is because they are using a dishonest metric The biggest funds in the world are supporting this and misleading journalists for PR coverage. The setup: Company signs 3-year enterprise deals. Year 1 is discounted (say $1M), Year 2 steps up ($2M), Year 3 is full price ($3M). They report $3M as “ARR” — even though they’re only collecting $1M right now. The worst part: The customer has an opt-out option at 12 months! It’s not actually a 3 year contract. In the chart below, by Q5 the company is trumpeting ~$100M “ARR” to press, while actual cash-generating, in-effect ARR is ~$35M. That’s ~3x inflation. On top of this, enterprise AI companies are bundling full-time “forward deployed engineers” into deals massively reducing margins, sometimes producing Year 1 negative margins. At some point customers are going to start triggering their opt-out clauses or aggressively negotiating down Year 3 pricing. And a wave of enterprise AI companies may collapse.
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some deep talks in slack today
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a reminder to talk to your customers
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it’s not long an agent problem, it’s a data problem
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more companies have silent churn more than they want to admit…
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Seat-based pricing is definitely not dead
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CARR should be a banned reporting number
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