SaaS Interviews with CEOs, Startups, Founders
Flip Reaches $12M ARR with AI Voice Support for 250 Brands
22 Apr 2026
Transcript generated automatically by AI and may contain errors.
Chapter 1: How did Brian Schiff pivot from a college ridesharing app to an AI voice company?
Can I take 250 customers times the minimum ACD range you gave me earlier, 50 grand a year? If that puts you again well into the eight figures, 12.5 million AR run rate. Is that the right direction? We are north of that. 20 million series A. What valuation, Brian? Hanging out right around 100 million in valuation. So the bank was never so low where you considered shutting the company down?
Not after the pivot. Before we made the pivot, we had scraps. We had a couple of customers in these small towns doing the ride share thing. That was a moment where either we were going to find a new, better business opportunity, or it was going to be a resume booster to go and get a job post-grad.
If someone came and offered you $150 million all cash upfront today to sell the business, you and Sam say... Hey folks, my guest today is Brian Schiff. He's the co-founder and CEO of Flip, formerly RedRoot, a verticalized AI voice assistant that automates customer service calls.
He and his co-founder, Sam, originally started the company as a ride-sharing app at Cornell before pivoting to voice AI in 2018. Brian, you ready to take us to the top?
Let's do it.
I got to talk about that first. How do you go from ride-sharing to voice? You're not just jumping to the hot trends, are you?
You know, it's funny when we started this, certainly Sam and I met a decade ago, my co-founder, we were freshmen in college at the time. And back in 2015, 2016, no question, the hot thing in startups was Uber and ride sharing and all that stuff. But they were banned in upstate New York. We were going to school at Cornell.
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Chapter 2: What challenges did Flip face during the pandemic?
So I think we were just looking to build and that was an easy place to start. It was sort of a product that you knew everybody wanted and it was a gap in the market. So we dove right in and then you just keep on running, right?
this is great you've had serious consistency i enter refiners all the time it's like one year at this startup but i'm looking at your linkedin now flip january 2018 to present going on eight years and three months huh yeah and uh i don't think it was even officially flip until like 2022 we were still operating under the red route name for some time there but it was sort of you know the earliest seedlings of of what the product and the business became
Yeah. Very interesting. Well, take us into that. Let's just fast forward to the product today and then we'll go back and get your and Sam's history. So the website header says automate your customer support calls with voice AI. Is this broad? Are you in a specific niche? Tell us what the product does today.
Yeah. So I think when people read AI is the technology of our lifetimes. And when you look at the opportunities that people are zeroing in on to use AI inside of a business environment today, there are two big use cases people are pointing to. The first one is AI coding. And the second one is AI customer support. So we are in this massive opportunity space of AI customer support.
And there are two approaches that exist right now. There are these generic horizontal platforms that are really going after companies in any industry. And then there are these hyper-focused, verticalized industry solutions. And that's the bucket that we're in. So we started in the transportation space. We have added retail and healthcare over the last couple of years.
But it is a very deep, verticalized solution for companies in those industries.
Let's talk about transportation. I mean, give me a sense. Can you name a transportation customer you work with and then give me the specific use case on how they use you to cut down support time?
Yeah. So it's, you know, the largest ground transportation companies in the world. As you mentioned, we started in rideshare. So for example, A2B transportation is the conglomerate that organizes most of the ground travel across the entire country and continent of Australia. And they receive tens of thousands of phone calls into their contact center
day with people looking to schedule rides modify their rides connect to their driver all the things that you would expect and we're able to automate all of those routine calls so we automate somewhere between 85 and 90 percent of the calls that they receive helping those customers move about their day uh in the way that they need to and and helping that company stay at the cutting edge
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Chapter 3: How does Flip automate customer support calls effectively?
There's nothing worse than overcomplicated pricing models. So we try and keep it really simple and aligned with the outcomes that we're driving. So it's just a monthly invoice that is capturing the amount of usage that you had at the billable rate.
just a youtuber i'm investing in my third fund we've deployed 250 million dollars into 550 software companies so far again at founderpath.com if you're interested in capital i would love to cut you a check because i know you're investing in your education you watch my show so sign up at founderpath.com and when you get the onboarding email i reply and i see all those just reply and say nathan i found you through youtube and i'll make sure to prioritize you i would love to cut you a check check out founderpath.com
You have folks obviously starting off on your free $0 set up integration, listen mode, intake proof of concept. So I understand you can go bottoms up if you want. I imagine some of you go top down as well. I'm going to force you into an answer here and you're not going to like the question, but it's going to help me give a better interview.
What would you say the average customer is paying you per year? I mean, are we talking either 10,000 ACVs for a million resolved calls or is it a million dollar ACVs for 10 million resolved calls?
It's usually somewhere between 50 and 500,000. So it's sort of, you know, these are established companies that have, you know, usually up over 100 employees. They're running a significant business. They've got complexity to their tech stack. And they've reached a point where they have no choice but to provide a great experience to their customers over the phone.
When I've interviewed folks that are not in your same space, but same sort of analogy, right, in terms of usage-based AI, et cetera, if you really are doing the jobs to be done and you bill for the job to be done, $1.50 per call resolved, net dollar attention is usually through the roof. So it's crazy.
You look at their customer list, you'll see a 10,000 customer, but you'll also see they have a million dollar per year customer. When are you guys going to have your first million dollar per year customer?
We do have a million dollar per year customer.
Nice.
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Chapter 4: What industries does Flip serve and why are they chosen?
That puts you again well into the eight figures, 12.5 million ARR run rate. Is that the right direction?
We are north of that, but no further comment.
That's great. How much time do you think you need to break 50 million of ARR? Is that a two-year goal, a one-year goal, three years?
I think that the world has realized, you know, when we started this, it was lunacy to talk about AI automating all of these conversations. And now we are at this moment where it is obvious, inevitable, and imminent. And I can't think and, you know, I have not been around technology for that long, but
But I can't think of a technology and a product category that an example where a new category was so obvious, so like broadly accepted so quickly. And the level of investment that you're seeing, right? Like every company, every CX leader out there needs to have an answer for, you know, what is their perspective? What have they done? What have they accomplished with AI?
So there is a, you know, there's a huge amount of interest in AI.
doing this and doing it successfully and we certainly think that we have the right solution for companies in these industries so you know time will tell you and i can can circle back when we cross the 50 million mark but uh yeah we're going we're growing quickly and and having fun along the way let's get more drilling me on the financials here nathan
I want to know. I want to know, right? Because companies like you are getting, they're celebrated, but also sort of frowned upon, right? The legacy players that you're replacing are saying they're just an AI rapper. The investors that just gave you money are saying, no, these guys are the real deal. And you know, you're the real deal. I want to get to the bottom of it.
You know, are you a rapper or is this a real company?
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