Apr 22, 2026 · 24m · top-founders
Flip Reaches $12M ARR with AI Voice Support for 250 Brands
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this interview, Flip co-founder and CEO Brian Schiff joins Nathan Latka to discuss how the voice AI platform navigated major pivots to reach over $12.5M ARR, process 300 million calls, and raise a $20M Series A.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 34% of the talking time here. How this is scored →
Nathan as informed peer 5.4 Guest teaching 4.1 Guest disagreement 2.1 Nathan pushing back 3.9
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 18:34 Brian rejects Nathan's 2021 pivot timeline
Brian directly corrects Nathan's misunderstanding of the company's chronology, explaining that the true existential pivot happened in 2018 when they abandoned ridesharing rather than in 2021.
Hardest push from Nathan ▶ 9:35 Nathan's clever questioning trap on top-tier ACVsNathan traps Brian into revealing sensitive financial data by asking when they will get their first million-dollar customer, forcing Brian to admit they already have one.
Biggest teaching moment ▶ 15:32 Brian explains vertical selection thesisBrian explains to Nathan why Voice AI cannot work for B2B CS and why highly competitive consumer markets innovate faster than oligopolies like airlines and utilities.
Nathan holds their own ▶ 5:29 Nathan details ETL data normalization defensibilityNathan demonstrates deep technical fluency by explaining why data normalization, continuous ETL ingestion, and specialized legacy integrations protect vertical software from AI commoditization.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Verticalized Voice AI and Transportation Use Case | 4 | 4 | 1 | 2 | Nathan asks Brian to break down Flip's core value proposition and ground transportation use cases. Brian educates Nathan on the difference between horizontal and vertical AI platforms, noting an 85-90% resolution rate. | |
| Domain Integrations and Technical Defensibility | 6 | 5 | 1 | 2 | Nathan displays industry knowledge regarding ETL pipelines, data normalization, and specialized niche integrations like FortiVoice. Brian agrees and highlights Flip's library of pre-built, battle-tested workflows. | |
| Usage-Based Pricing and Proof of Concept | 5 | 4 | 2 | 4 | Nathan presses on pricing mechanics to understand whether contracts convert from proof of concepts to bulk annual minimums. Brian clarifies their simple usage-based model billing $1.50 per resolved inbound contact. | |
| Scale, Revenue Milestones, and Customer Base | 7 | 3 | 3 | 6 | Nathan corners Brian with mathematical deductions, setting a conversational trap about million-dollar contracts and calculating ARR over $12.5M. Brian admits they have a seven-figure client and confirms revenue is north of that estimate. | |
| Voice AI Inevitability and Defending B2B Value | 5 | 4 | 2 | 4 | Nathan bluntly challenges whether Flip is simply an AI wrapper or a defensible enterprise business. Brian counters by asserting that real business value and delivering measurable ROI is what defines enduring B2B software. | |
| Strategic Framework for Selecting Market Verticals | 5 | 6 | 3 | 4 | Brian lays out his framework for vertical expansion, contrasting competitive consumer sectors with slow oligopolies like airlines. Brian also corrects Nathan's confusion regarding their 2018 pivot versus their 2021 retail expansion. | |
| Series A Terms and Rejecting Acquisition Offers | 6 | 3 | 3 | 5 | Nathan probes into Series A valuation and whether the founders would reject a $150M cash buyout, then pitches investing a $20k check. Brian reveals a $100M valuation while deflecting the investment pitch to offline conversation. |
Statements from this episode (15)
Schiff: Real software defensibility requires deep edge-case handling across customers
“It's one thing to have enough of an integration with Shopify, for example, that you can put them on your website as a listed integration. It's another thing to, as you said, be deep enough in it with enough customers such that you have run into all of the edge…”
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.”
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…”
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.”
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.”
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…”
Schiff: Oligopolistic Sectors Like Airlines and Utilities Resist Contact Center Innovation
“So when you look at financial services, or you look at utilities, or you look at airlines so many of those contact centers are like, they're still not even migrated to the cloud, right? I think the incentive to innovate is, is much less in these sort of oligop…”
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.”
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…”
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.”