Assertion certainty 4/5 debate potential 2/5

Overtoom: Lassie's first agent achieves a 98% automation rate

Stein Overtoom · “Every small business should run itself” | Lassie with a16z · Jul 29, 2026 · at 21:37

Stein Overtoom is the co-founder of Lassie, an AI startup automating billing and administrative workflows in dental practices.

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“For the first agent, 98% of the work and then there's a sliver left. And then the interesting thing that we have thousands of staffers that are basically giving us input. On how to make that appeal that the agent currently cannot do.”

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More from Stein Overtoom

Disclosure
Overtoom: Lassie charges five figures for an agent doing 30 hours monthly
“We are already charging five figures for kind of like this first agent that only does 30 hours of labor a month.”
Stein Overtoom Jul 29, 2026 ▶ 16:17 “Every small business should run itself” | Lassie with a16z
Assertion Not checkable as stated
Overtoom: Demand for dentists and plumbers is double current supply capacity
“If you just look at the dental practice, but the same applies to try to find a good plumber there's just like twice as much demand that currently can be supplied.”
Stein Overtoom Jul 29, 2026 ▶ 43:33 “Every small business should run itself” | Lassie with a16z
Assertion Not checkable as stated
Overtoom: Hundreds of thousands of small practices handle billing manually
“There are, like, hundreds of thousands of these small businesses that literally, like, do this all by hand.”
Stein Overtoom Jul 29, 2026 ▶ 3:32 “Every small business should run itself” | Lassie with a16z
Assertion Not checkable as stated
Overtoom: US dental automation is a $1B recurring revenue market
“Serving that market first, you're looking at a one billion dollars in like a recurring revenue as a market.”
Stein Overtoom Jul 29, 2026 ▶ 34:40 “Every small business should run itself” | Lassie with a16z
Insight
Overtoom: All small businesses share the exact same core administrative workflows
“All small businesses at an abstract level, Like have a system of record they need to read and write into. They all have customers in doctor offices. They happen to be patients, but it's interacting and transacting around payments. You need to book appointments…”
Stein Overtoom Jul 29, 2026 ▶ 35:10 “Every small business should run itself” | Lassie with a16z
Insight
Overtoom: Standard B2B databases like Apollo and LinkedIn fail for SMB sales
“Because if you were to sell to like me, you like find me, you know, in clay and you enrich it with some Apollo data, and then you look me up on LinkedIn, then you know, again, this is the guy that's going to buy my HR system. We can't really do that because Dr…”
Stein Overtoom Jul 29, 2026 ▶ 57:14 “Every small business should run itself” | Lassie with a16z
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