FlipCX Revenue, Valuation & Funding (2026)

[00:00] Can I take two fifty customers times the minimum ACV range you gave me earlier, $50 a year? That puts you again well into the 8 figures. 12,500,000 AR run rate. Is that the right directionally? [00:08] >> We are north of that. [00:09] 20,000,000 Series A. What valuation, Brian? [00:11] >> Hanging out right around 100,000,000 in valuation. [00:14] Okay, the bank was never so low where you considered shutting the company down. [00:17] >> Not after the pivot. Before we made the pivot, we had scraps. We had a couple of customers in these small towns doing the rideshare 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. [00:33] Someone came and offered you $150,000,000 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? [00:54] >> Let's do it. [00:55] I gotta talk about that first. How do you go from ride sharing to voice You're not just jumping to the hot trends, are you? [01:00] >> You know, it's funny when we started this, certainly, right, 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, and we were going to school at Cornell. So I think we were just looking to build, and that was an easy place [01:20] >> 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. [01:28] This is great. You've had serious consistency. I interview founders 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. [01:38] >> Yeah. And 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 sorta, you know, the earliest seedlings of of what the product and the business became. [01:50] Yeah. Very interesting. Well, us into the 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 or are you in a specific niche? Tell us what the product does today. [02:02] >> Yeah, so I think when people write AI is the technology of our lifetimes. 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 customer support. So we are in this massive opportunity space of AI customer support, there are two approaches that exist right now. There are [02:26] >> 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. [02:48] 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? [02:56] >> Yeah, it's 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 every 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 [03:22] >> all of those routine calls. So we automate somewhere between 8590% of the calls that they receive, helping those customers move about their day in the way that they need to and helping that company stay at the cutting edge. [03:35] So I use A to B. I'm landing in Sydney. I'm flying to give a keynote. I want a nice little limo. I wouldn't do that, by the way. I like to stay lean. But if I wanted a limo, I'd call a and b. And what you're saying is if I called that line, it used to be some guy I'm getting or gal somewhere. You're automating most of that. And and it's not one of these things where [03:50] I'm, stuck trying to press the right number for 20. This is like, how do you measure a resolution rate? [03:55] >> Yeah. Ultimately, you want to, as quickly as possible, establish credibility with the caller that this is not your 90s era automated assistant, and it is something that understands who is calling, and it has a level of, you know, intelligence and cleanliness to it. And then as quickly as we can figure out what it is they're calling for, we're gonna have the integrations on the back end with the systems that are required to schedule the trip, cancel [04:18] >> the trip, change the pickup address, get them a price quote, all of the above. [04:22] When a new transportation company signs up to use you, I imagine one of the key things you must do to activate them and keep net dollar attention high is figure out how to help them train your system with their brain, their context, whatever it is. How do you do that? And what is the thing they're usually giving you to train your system? Is it a bunch of Google Docs? Is it a bunch of call history? What [04:40] is it? [04:41] >> Yeah, so the whole benefit of a industry specialized solution is that 95% of what any company is gonna need, we already have in the platform out of the box. So when you think about those key integrations with the phone systems and with the dispatch platforms, when you think about all those types of topics that we just touched on that people might be calling for, we have those workflows out of the box, battle tested across hundreds of [05:06] >> customers and millions of calls. So when the next company signs up, it is this dynamic of standing on the shoulders of giants and they can come in and they can very easily configure it to the specific business logic and brand preference of their company. But they don't need to go through this experience of building the whole thing ground up from scratch like you would need to working with any of the horizontal player. [05:29] A lot of folks are saying, oh, man. Your enterprise software is in trouble. AI can just rip it out. But you and I both know building what you built here on my screen right now, which is maintaining all these integrations, ingesting the data, running an ETL process on it to normalize the data, then use across companies is like very, very difficult. Would you agree or disagree with that statement since you're doing it here front and center? [05:48] >> I agree wholeheartedly. And 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 cases and you have made it something where before the issue even arises, your team has seen it before and they can anticipate it and they [06:12] >> can navigate around it with the customer. [06:14] Makes tons of sense. Again, you guys obviously, you might know Aircall for phone systems, but Brian knows that for AMB and transportation folks, they use this weird thing we've never heard of called Fortivoice. And he knows he's got that integration live and it's required for an edge case. Right? [06:25] >> Exactly right. And I'm not sure they're running on that one, but somebody is. [06:29] Yeah, fair enough. Fair enough. Okay. Talk me about pricing. How do you get people paying for this thing? Is average ACV, call it mid market enterprise? How do think about that? [06:37] >> Yeah. So inside of these industries that we operate, one of the beauties is this works for companies of all size. And because of how easy it is to get up and running, it's not prohibitive and it's not just for the large companies in a space. So for all organizations, we're able to offer no money upfront. We handle the setup and the integration at no cost. And then we do what we call listen mode, which is basically [07:00] >> in taking a couple thousand of their phone calls to understand across, if we use a retail example, there are 200 different call topics where we have automated workflows out of the box. What are the ones that are most important for them, for that company, which then establishes a roadmap for what the prioritization is going to be for turning on new automations week over week. At the point when we do that, we'll enter into a proof of [07:25] >> concept period. And the customer is primarily just paying us a dollar 50 per contact that we're able to resolve end to end. [07:32] A dollar 50 per inbound contact requests that you resolve end to end. Okay. Interesting. And are those so so there's obviously paid proof of concepts. Then what? How did do you move them onto a plan where they're buying a bulk number of resolved tickets? So it's a dollar 50 times a minimum of 1,000 and they're paying for a year. How do you move past that? [07:50] >> There's nothing worse than over complicated 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 the billable rate. [08:04] Guys, remember, I am not just a YouTuber. I'm investing in my third fund. We've deployed $250,000,000 into five fifty 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 [08:26] 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 setup 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 gonna force you in into an answer here, you're not gonna like the question, but it's gonna help me give a [08:45] better interview. What would you say the average customer is paying you per year? I mean, are we talking these are 10,000 ACVs for a million resolved calls or is it a million dollar ACVs for 10,000,000 [08:54] >> resolved 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 a 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, and that's where it works. [09:15] Interviewed When folks that are not in your same space, but same sort of analogy, right, in terms of usage based AI, etcetera, you know, if you really are doing the jobs to be done and you bill for the job to be done, a dollar 50 per call resolved, Net dollar attention is 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 [09:33] million dollar per year customer. When are you guys gonna have your first million dollar per year customer? [09:36] >> We do have a million dollar per year customer. [09:38] You see how I asked that? You see how I asked that to get the answer? That great. That's awesome. Yeah. Well, congrats. [09:45] >> We just announced our $20,000,000 series A at the turn of the year. And with that also announced 300,000,000 phone calls automated to date, which is just, when you start from nothing and you start at the beginning, 300,000,000 is a lot of zeros and a large number. Then also cross that two fifty customer mark. [10:04] That's awesome. [10:05] >> So it's all of this is new and it's exciting and it's also a little bit terrifying. And it's important for us that when we show up with our customers, they understand the steps that we've gone through and the things that we've learned along the way and the scale that we're operating at right now. [10:19] Makes tons of sense. Now you mentioned 300,000,000 automated calls. I don't know if you were always billing a dollar 50 per automated call. I can't take 300,000,000 times a dollar 50 and assume you've done $450,000,000 of revenue life to date. I assume that's not accurate. [10:31] >> So the billing model is slightly different in each of the industries that we operate in. So the dollar 50 is the retail rate and then basically based on the complexity of conversation that we're handling. So transportation where it is shorter, quicker hitter conversations, we're charging a fraction of that rate. But yeah, we've done significant revenue. We're well into the 8 figures on a ARR basis. So we're rocking and rolling. [10:54] Yeah. You can brag. You look down like you're ashamed when you share these numbers, but you can brag about it. I mean, right? This is a good thing. Can I take 250 customers times the minimum ACD range you gave me earlier, $50 a year? That puts you again well into the 8 figures, 12,500,000 ARR run rate. Is that the right directionally? [11:09] >> We are north of that, but no further comment. [11:12] That's great. How much time do you think you need to break 50,000,000 of ARR? Is that a two year goal, a one year goal, three years? [11:19] >> 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, I have not been around technology for that long, but I can't think of a technology and a product category that An example where a new category was so obvious, so broadly accepted so quickly, and the [11:47] >> level of investment that you're seeing, every company, every CX leader out there needs to have an answer for what is their perspective? What have they done? What have they accomplished with AI? So there's a huge amount of interest in 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 50,000,000 [12:11] >> mark. But, yeah, we're going we're we're growing quickly and and having fun along the way. [12:16] Let's get more [12:17] >> Drillin'me on the financials here, Nathan. [12:20] I wanna know. I wanna 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 wanna get to the bottom of it. You know? Are you a rapper or is this a real company? [12:35] >> Yeah. Ultimately, I think the purpose of a b to b app is to deliver measurable value for your customers. And so, you know, anybody that is not using the latest and greatest technology to make their product better for their customers is sort of like missing the mark, missing the moment, and probably focused on the wrong things. [12:53] Yep. Okay. Let's get more of the backstory. I obviously grow down everything today, but backstory, 2018, you know, I think you Cornell guest lecturer, you know, first job hockey operations manager, something like that. Is this right? Correct my history here. [13:05] >> Yeah. I I was a hockey player growing up. First, I'd say, shout out to Eric Nates, but first real serious job that I've that I had was was starting this company. Yeah. There we are with the LinkedIn. So as I touched on at the start, Sam and I met way back freshman year of college, started our entrepreneurial journey, went through Cornell's eLab Accelerator program, which is one of those things we wouldn't be here without that experience. [13:28] >> Launched that ride sharing app, did it at Cornell, Syracuse, Binghamton, Oneonta, all of the big schools across Upstate New York. And then 2018 made the pivot to, hey, maybe there's this much bigger and better opportunity to optimize all the business that's already happening on the phone and took that leap and spent the first couple of years, call it from 2018 through COVID, really figuring out this whole business in the transportation industry and going from a point [13:56] >> where we were working with a small operator in Ithaca, New York to working with all of the largest transportation operators across the globe. At that point, turned around and raised our first significant round of funding, which was an 8,500,000 round. This was 2021, end of twenty one, early twenty two. And the idea was we had just taken our first step into retail. So we had taken this technology, we had packaged it into a product, we had [14:21] >> built a business that was working really well. And this was still with like Alexa era voice AI right before sort of the chatty bitty moment. And it was, hey, can we take this concept and now replicate it in a much bigger and faster growing category? So went into retail, Brooklinen was our first customer back in the day. They launched us right before Black Friday. [14:43] Wait, Brooklinen as an ecom. [14:45] >> Yeah, yeah. They were our first retailecom customer. I don't know what they saw in us, but I am eternally grateful. Launched with them, raised that round of funding that sort of led the surge where we're now working with brands the size of Under Armour and Tory Burch and the Authentic Brands Group, large household name retailers. And then in 2024, going into the early part of twenty twenty five, health care as that third industry. Been hyper focused [15:12] >> in urgent care inside of health care where we're now serving a couple thousand clinics across the country. [15:17] How'd you decide? I mean, it's fascinating to me. I understand why you go from a ride sharing app. You have relationships. You know this Ithaca company, small operator. Of course, you go into helping them get their inbound calls faster, but then you decide e commerce and then you decide health care in 2024. Why did you decide you could go after any market? Why health care? [15:32] >> Yeah. It's in some ways the million dollar question, the billion dollar question. 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 B2B environment. Like we wouldn't have our own agent do the customer success for our product with our customers. So you're looking at the big consumer industries where there is a high volume of contacts. And then I think like [15:58] >> the variable that becomes important is how competitive is the market? Right? You need industries where there is a high degree of competition, which forces the companies to need to innovate, to be better on the margin, to provide that better customer experience or patient experience in a healthcare setting. 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 [16:26] >> to the cloud. I think the incentive to innovate is much less in these sort of oligopolized markets. So we were hyper focused on, we're going to take this industry specialized approach. We can only work in one or a couple of spaces, and we need to make sure that the ones that we're choosing to work in are going to be the ones that are ready to adopt this first and fastest. [16:46] Yeah. It makes a ton of sense. Interesting. Okay. So jumping into new markets now makes sense to me. Walk me through revenue growth history. Do you remember what year you broke a million of revenue? [16:54] >> Man, I honestly don't remember at least off the top of my head. I do know that 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. [17:06] Measured by what? What's efficiency mean to you? [17:08] >> Just like annual burn figures. And it's funny, we're doing it in a space where there are companies doing AI customer support that are just so overfunded. And part of it is that their model requires it. A customer that we can get online and get achieving great results with one or two resources will require them multiple years with thirty, forty, 50 resources dedicated to that one account building the bespoke solution for them. So part of it is [17:38] >> that their economics demand that level of capital. I also think we've built this business by having a reference list as long as our customer list. Like, this has always been a we're gonna get a customer. We're gonna treat them right. We're gonna deliver everything we told them that they were gonna deliver, and then they're gonna tell their friends about it. And inside of these industries, it's small networks and trust is sort of the ultimate currency. And [18:02] >> it makes for a business that can grow really quickly. That's also not going to burn a tremendous amount of money. [18:06] I'm trying to get a sense of like when you really hit it. So you did the 8,500,000 first seed run-in 2021. Did you still have some of that money in the bank, you know, going up when you just did the 20,000,000 series a in January 2026? [18:16] >> Yeah. Okay. [18:17] So the bank was never so low where you considered shutting the company down? [18:19] >> Not after the pivot. So we had and and I guess maybe two moments. So before we made the pivot, right, we had, you know, you were we had scraps. We had a couple of customers in these small towns doing the rideshare thing. So that was a critical moment where [18:34] 2021 is what you call the pivot, right? [18:36] >> No. So I'm talking about 2018 when left the rideshare behind and then started working on Voice AI. 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. So that was one of those critical moments that fork in the road that could have gone either way. And then during COVID, we were serving the transportation industry [19:00] >> and transportation shut down. It was the first thing that shut down. So we saw overnight 80%, 90% of our revenue usage based model came back and nipped us in the behind. We saw March 2020, it all disappeared. So that was another moment where cash got really tight and we needed to keep a cool head, but make hard decisions and figure out how to chart the business through that period. And then we came out strong on the [19:29] >> other side. We took that step into retail as that second larger industry, and we were able to go and raise that first big round of funding. And since then, it's been a pretty off to the races, steady climb. [19:45] Is it fair to say since 2020 the pivot was in 2018, 2021 saw you go into ecom. Now you have two markets. You use that traction to show investors. That's how you got the $8,500,000 round done. You must have had some revenue traction at that point. Were you around a million of ARR you think back then? [20:01] >> Yeah. We were just over that. Yeah. [20:02] Okay. There you go. Okay. And then basically, it sounds like you've had pretty explosive growth since then. Something like 200 to 300% year over year. [20:09] >> That's correct. [20:10] Yeah. Okay. Super interesting. Last question here before we wrap up because I wanna be respectful of your time. Many of these companies, when you go out and do an equity round, that's also a good moment where you potentially sit you go out to, you know, M and A folks reach out and say, hey. Instead of raising a round and jacking me a valuation, would you consider a $200,000,000 all cash offer from x company, from Intercom, right, [20:26] to merge? Did you have any m and a offers aligned with the series a process or no? [20:31] >> Yeah. They always do align. You're a 100 right. And yeah, they're they're coming across our desk. I think that, you know, we we've covered the whole backstory here. Right? Sam and I started this journey a decade ago. And first you go through this never ending maze to find real true product market fit. And then you have the early scaling of the business to like [20:50] You cut that off your story by the way. I just wanna point that out. You cheated a little bit. You cut off twenty sixteen to twenty eighteen on your LinkedIn, all the hard work. Right? You you you sort of said, me just put 2018 as a start date, but the hard shit was before that. [21:00] >> In some way. Mean, it it you need to find product market fit and then you need to like get each cog in the wheel of the business working. You need marketing. You need sales. You need customer success, you need product, you need engineering. And it always right. There's some period of time where it feels like once you get one bit working, the other part collapses and you're doing like whack a mole for some period of time. [21:20] >> And then you get to this point where, okay, this thing is working. There are people, right? You've got a foundation of a team in all of these core areas. They're working together. The business is growing sort of without these Herculean founder efforts. And it's like, you know, it's a whole nother level in the way that you can think and in the amount that you can go and get done. Very long way of saying, you know, for [21:42] >> Sam and I, like, it's never been more fun than it is right now. And what what what are we going to do? We're going to sell it and then we're going to go back to the beginning start from nothing again. I think all of it was to have the opportunity to go and sort of live this next stretch and build the business. So, yeah, mean, we're all in. [22:01] So just to be clear, you're past 8 figures of revenue, call it 12,000,000 of revenue. If someone came and offered you a 150,000,000 all cash upfront today to sell the business, you and Sam say, no. Thank you. [22:11] >> Yeah. No. Thank you at that figure. [22:13] I love it. I love it. Alright. Last question. I'll put some pressure on you. You can say no, but I'm gonna ask it anyway. My audience expects it. 20,000,000 series What what value what what valuation, Brian? [22:21] >> Hanging out right around a 100,000,000 in valuation. [22:24] Was that higher or lower than you expected when you started the process? [22:27] >> It's funny. One of our seed investors said, Brian, for better or for worse, you attract very sober, high quality investors. And so I think it's the classic wisdom, right? It's more important who you're working with than optimizing the details in the early stages of building a business. 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 [22:51] >> and we're sort of off to the races now. [22:53] Brian, can I would you am I allowed can I put a 20 k check-in that on the same terms? [22:57] >> That's [22:58] all. I'm a distribution guy. Like, I'm I'm a I'm a distribution channel for you. You have spamming zero podcast. You know the power of distribution. Let me put in 20 k same terms. [23:03] >> Yeah. Spamming zero. Look, you were really doing your research. That's all that's that's offline chitchat, Nathan. [23:09] Alright. Well, hey, listen. You're you're you're a real pleasure to interview. I appreciate the time. If people wanna follow your journey online, where can they find you? [23:14] >> I'm a sucker for LinkedIn for better or for worse. I I mostly keep myself out of the the chaos of x, so I'd say LinkedIn's your best bet and certainly follow the flip page. We we keep the world updated and [23:28] yeah. Guys, 2016 ride sharing app at Cornell with his best friend Sam realized that was a terrible business model. Had the big pivot in 2018, left ride sharing behind, but they knew the space so well. They said, what if we could work with a small operator in Ithaca, New York and help them get their inbound calls resolved faster? That's exactly what they did. In 2021, they really started figuring added a second industry, Tory Burch's e comms [23:48] of the world, and ultimately used that revenue traction, passed a million of revenue to raise an 8.5 seed round. They were really smart with spending that money, got into health care in 2024 and urgent care. Since 2021, growing about three x year over year the past three years, that traction enabled him to drive a very competitive series A process. 20,000,000 closed in January 2026, just a couple of months ago. Healthy valuation approaching $100,000,000, and he's not [24:09] just a rapper. He's got 75%, 75% gross margin, which tells you he's not a rapper. You can start off with a $0 setup and integration, ultimately scale and help use them to get your calls answered faster. Right now, again, focused on healthcare, retail, e comm, and transportation. I bet there's more coming in the future. But Brian, thank you for taking us to the top. You won't believe this CEO's revenue. 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