Squire
company on 5 shows · 8 statements across 3 episodes · said 34 times in 7 episodes since 2020
the Pitch 9 
How I Built This 5 
the Official SaaStr Podcast 2 
the Startup Ideas Podcast 1 
20VC
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tap a year for its mentions
the Pitch 9How I Built This 5the Official SaaStr Podcast 2the Startup Ideas Podcast 1
2025 1 mention in 1 episode
2024 8 mentions in 1 episode
2022 1 mention in 1 episode
2021 2 mentions in 2 episodes 1 per episode
2020 5 mentions in 1 episode
every mention on every show, scene by scene, with the transcript →
8 statements about Squire, every show
Middleton wrote first $100k check into Squire after VCs passed
“Squire was the first angel deal I did, and they went and pitched, like, every venture investor, everybody passed, and I wound up writing their first hundred grand into the company”
Middleton: Squire angel investment is at 160x on paper
“They're, that, that's one of my best performing on paper investments. It's at a 160 X my cost basis, but yeah, that's a good one.”
Squire charges shops $100-$250 monthly plus a $1 consumer booking fee
“The main way is from handling the payment processing. So that, that's really core to our business. There's a subscription component. So the shops that use our platform will pay a hundred dollars to two 50 a month. And then there's a customer booking fee. So if…”
Squire's revenue essentially dropped to zero in March and April 2020
“March, April, you know, our revenue essentially went to zero.”
Squire waived subscription charges for all customers through October 2020
“And we also decided to waive all of our subscription charges to current and new customers until October, because we knew that their revenue was also going to go to zero.”
Squire's May and June 2020 revenue actually exceeded pre-COVID levels
“In fact, May and June exceeded pre-COVID numbers just because of all the new business that we're bringing on.”
Squire was financially prepared for over 12 months of zero revenue
“It's always safe to kind of assume the worst case and be prepared for the worst case, which we were prepared to go to zero revenue for over 12 months.”
YC startup Squire grew revenue 40x within months of Middleton's investment
“One of my more recent investments And so it's a company called Squire, who is currently in Y Combinator about the demo in a couple of weeks. And these are just two incredible founders, Dave and Song, who have started from zero startup experience to now having …”