The Ledger

Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.

clear all ✕

why aren't all 13 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 1 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Opinion
Schiff: Competing AI customer support companies are heavily overfunded and inefficient
“There are companies doing AI customer support that are just so overfunded. And part of it is that their model requires it, right? A customer that we can get online and get achieving great results with one or two resources will require them, you know, year, mul…”
Brian Schiff Apr 22, 2026 ▶ 17:13 Flip Reaches $12M ARR with AI Voice Support for 250 Brands
Disclosure
Flip charges $1.50 per fully resolved contact during proof of concept
“At the point when we do that, we'll enter into a proof of concept period and the customer's primarily just paying us a dollar 50 per contact that we're able to resolve end to end.”
Brian Schiff Apr 22, 2026 ▶ 7:22 Flip Reaches $12M ARR with AI Voice Support for 250 Brands
Assertion Supported
Flip raised a $20M Series A with 300M automated calls
“We just announced our Twenty million dollar series a at the turn of the year. And with that also announced three hundred million phone calls automated to date, which is just, you know, when you start from nothing and you start at the beginning, three hundred m…”
Brian Schiff Apr 22, 2026 ▶ 9:46 Flip Reaches $12M ARR with AI Voice Support for 250 Brands
Assertion Not checkable as stated
Schiff: Flip's ARR is north of $12.5M
“We are north of that, but no further comment.”
Brian Schiff Apr 22, 2026 ▶ 11:09 Flip Reaches $12M ARR with AI Voice Support for 250 Brands
Insight
Schiff: Voice AI Fits High-Volume B2C, Not B2B Environments
“First, you know, I think the first sort of realization is that this technology is great for Large consumer businesses, but you wouldn't use it in a B to B environment. Like we wouldn't have our own AI agent do the customer success for our product with our cust…”
Brian Schiff Apr 22, 2026 ▶ 15:37 Flip Reaches $12M ARR with AI Voice Support for 250 Brands
Assertion Open · timeframe Apr 2026
Schiff: Flip raised $20M Series A at ~$100M valuation
“Hanging out right around a hundred million in the valuation.”
Brian Schiff Apr 22, 2026 ▶ 22:22 Flip Reaches $12M ARR with AI Voice Support for 250 Brands
Assertion Not checkable as stated
Schiff: Flip Serves Thousands of Urgent Care Clinics
“And then in in 2024, going into the early part of 2025, added health care as that third industry. Been hyper focused. In urgent care inside of healthcare, where we're now serving a couple thousand clinics across the country.”
Brian Schiff Apr 22, 2026 ▶ 15:05 Flip Reaches $12M ARR with AI Voice Support for 250 Brands
Assertion Not checkable as stated
Schiff: Flip has a customer paying $1M+ annually
“We do have a million dollar per year customer.”
Brian Schiff Apr 22, 2026 ▶ 9:37 Flip Reaches $12M ARR with AI Voice Support for 250 Brands
Assertion Not checkable as stated
Schiff: Flip grew revenue 3x year-over-year over the past couple years
“Over the last couple of years, we've been growing at a three X year over year rate, and we've been doing it with like a remarkable level of efficiency.”
Brian Schiff Apr 22, 2026 ▶ 16:59 Flip Reaches $12M ARR with AI Voice Support for 250 Brands
Disclosure
Flip received four Series A term sheets, rejecting the highest offer
“So we had three or four term sheets. We did not go with the largest term sheet, but we went with the partners that we were excited to build with and we're sort of off to the races now.”
Brian Schiff Apr 22, 2026 ▶ 22:45 Flip Reaches $12M ARR with AI Voice Support for 250 Brands
Assertion Not checkable as stated
Schiff: Flip was at just over $1M ARR when raising in 2021
“Yeah, we were just over that, yeah.”
Brian Schiff Apr 22, 2026 ▶ 20:01 Flip Reaches $12M ARR with AI Voice Support for 250 Brands
Assertion Not checkable as stated
Schiff: Flip lost 80-90% of its revenue overnight in March 2020
“March of 2020, it all disappeared. So that was another moment where cash got really tight and we needed to, you know, keep a cool head but make hard decisions and figure out how to chart the business through that, you know, through that period.”
Brian Schiff Apr 22, 2026 ▶ 19:05 Flip Reaches $12M ARR with AI Voice Support for 250 Brands
Assertion Supported
Schiff: Flip Serves Under Armour, Tory Burch, and ABG
“That sort of led the surge where we're now, you know, working with brands the size of Under Armour and Tory Burch and the Authentic Brands Group.”
Brian Schiff Apr 22, 2026 ▶ 14:53 Flip Reaches $12M ARR with AI Voice Support for 250 Brands
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