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SaaS Interviews with CEOs, Startups, Founders
Flip Reaches $12M ARR with AI Voice Support for 250 Brands
00:24:34
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- [00:00]
A
Can I take 250 customers times the minimum ACV range you gave me earlier. 50 grand a year. That puts you again well into the eight figures. 12.5 million AR run rate, is that
- [00:08]
B
the right Directionally, we are north of
- [00:09]
A
that 20 million Series A. What valuation, Brian?
- [00:12]
B
Hanging out right around 100 million in
- [00:14]
A
valuation because the bank was never so low where you considered shutting the company down.
- [00:17]
B
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 postgrad.
- [00:33]
A
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 RedRoute, 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?
- [00:55]
B
Let's do it.
- [00:56]
A
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?
- [01:00]
B
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 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?
- [01:29]
A
This is great. You've had serious consistency. I interview finish all the time. It's like one year at this. Start looking at your LinkedIn now. Flip January 2018 to present. Going on eight years and three months, huh?
- [01:38]
B
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 sort of, you know, the earliest seedlings of. Of what the product and the business became.
- [01:51]
A
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.
- [02:03]
B
Yeah, so I think when people read a. 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, and there are two approaches that, 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, 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]
A
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]
B
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, 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 all of those routine calls. So we automate somewhere between 85 and 90% 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]
A
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, 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 it's not one of these things where I'm like stuck trying to press the right number for like 20 minutes. This is like, how do you measure a resolution rate?
- [03:55]
B
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 going to have the integrations on the back end with the systems that are required to schedule the trip, cancel the trip, change the pickup address, get them a price quote, all of the above.
- [04:22]
A
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 retention 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? What is it?
- [04:40]
B
Yeah, so the whole benefit of a industry specialized solution is that 95% of what any company is going to 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, you know, 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 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 players.
- [05:30]
A
A lot of folks are saying, oh man, you know, enterprise software's 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, you know, front and center?
- [05:49]
B
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 can navigate around it with the customer.
- [06:14]
A
Makes tons of sense. Again, you guys, obviously you might know air call for phone systems, but Brian knows that for AMB and transportation folks they use this weird thing we've never heard of called Fort Avoice. And he knows he's got that integration live and it's required for an edge case.
- [06:26]
B
Right, exactly right. And I'm not sure they're running on that one, but somebody is.
- [06:29]
A
Yeah, fair enough, Fair enough. Okay, talk me about pricing. How do you, how do you get people paying for this thing is, you know, is average ACV called mid market enterprise. How do you think about that?
- [06:37]
B
Yeah, so inside of these industries that 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 up front. We handle the setup and the integration at no cost. And then we do what we call listen mode, which is basically intaking a couple thousand of their phone calls to understand across. You know, 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 concept period and the customer is primarily just paying us a $50 per contact that we're able to resolve end to end.
- [07:33]
A
It's $1.50 per inbound contact request that you resolve end to end. Okay, interesting. And are those so. So there's obviously paid proof of concepts. Then what. How do you move them onto a plan where they're buying a bulk number of resolve tickets so it's a dollar fifty times a minimum of a thousand and they're paying for a year. How do you move past that?
- [07:50]
B
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.
- [08:04]
A
Guys, remember, I am not just a YouTuber, I'm investing in my third fund. We've deployed $250 million into 550 software companies so far. Again@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@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 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 going to force you in 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 is, what would you say the average customer is paying you per year? I mean are we talking these are 10,000 ACVs for you know, a million resolve calls or is it, you know, a million dollar ACVs for you know, 10 million resolved calls?
- [08:55]
B
It's usually somewhere between 50 and 500,000. So it's sort of, you know the, 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. And that's where it works.
- [09:15]
A
When I've interviewed, 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, you know, 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 tension is usually through the roof. So it's CR. You look at their customer list, you'll see a 10,000 customer but you also see they have a million dollar per year customer. When are you guys going to have your first million dollar per year customer?
- [09:37]
B
We do have a million dollar per year customer.
- [09:39]
A
You can see I asked that. You see how I asked that to get the answer. That was great. That's awesome. Yeah.
- [09:44]
B
Yes.
- [09:45]
A
Well, congrats.
- [09:46]
B
We just announced our $20 million Series A at the turn of the year. And with that also announced 300 million phone calls automated to date. Which is just, you know, when you start from nothing and you start at the beginning, 300 million is a lot of zeros and a large number. And then also cross that 250 customer mark.
- [10:05]
A
That's awesome.
- [10:06]
B
So it's, all of this is new and is, and it's exciting and it's also a little bit terrifying and, 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
- [10:19]
A
right now makes tons of sense. Now you mentioned 300 million automated calls. I don't know if you were always billing $1.50 per automated call. I can't take 300 million times A$50 and assume you've done $450 million of revenue life to date. I assume that accurate.
- [10:32]
B
So the billing model is slightly different in each of the industries that we operate in. So the $50 is the retail rate and then basically based on the complexity of the 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, we've done significant revenue. We're well into the eight figures on a R basis, so we're rocking and rolling.
- [10:55]
A
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 ACV range you gave me earlier, 50 grand a year. That puts you again well into the eight figures. 12.5 million AR run rate, is that the right directionally?
- [11:09]
B
We are north of that, but that's great. Further comment that's great.
- [11:14]
A
What, 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?
- [11:19]
B
I think that the world has realized, you know, when we started this it was, 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, 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 like broadly accepted so quickly and the level of investment that you're seeing, right, like every company, every 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, 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 million mark. But yeah, we're going, we're, we're growing quickly and, and having fun along the way. Let's get more drilling me on the financials here, Nathan.
- [12:20]
A
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. I want to get to the bottom of it. You know, are you a rapper or is this a real company?
- [12:36]
B
Yeah. Ultimately, I think the purpose of a B2B app is deliver 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]
A
Yeah. Okay, let's get more of the backstory. I obviously grow down everything today, but Backstory 2018, you know, I. Thank you. Cornell guest lecturer, you know, first job, hockey operations manager, something like that. Is this right? Correct.
- [13:05]
B
Yeah. 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, 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, you know, is one of those things. We wouldn't be here without that experience. 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, you know, 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 where we were working with a, you know, small operator in Ithaca, New York, to working with all of the largest transportation operators across the globe at that point, turned around and. And raised our first significant round of funding, which was an eight and a half million dollar round. And this was 2021, end of 21, early 22. 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 built a business that was working really well. Right. And this was still with like Alexa era voice AI right before sort of the ChatGPT moment. And it was, hey, can we take this concept and now do. Replicated 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]
A
Wait, Brooklinen as an E Comm?
- [14:45]
B
Yeah, yeah. They were our first retail E comm 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, you know, working with brands the size of Under Armour and Tory Burch, the Authentic Brands group, really large, you know, household name retailers. And then in, in 2024, going into the early part of 2025, added healthcare 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.
- [15:18]
A
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 healthcare 2024. Why did you decide you could go after any market? Why health care?
- [15:33]
B
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 the variable that becomes important is how competitive is the market.
- [16:02]
A
Right.
- [16:03]
B
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 to the cloud. Right. I think the incentive to innovate is, is much less in these sort of oligopolized markets. So we were hyper focused on, you know, 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.
- [16:47]
A
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?
- [16:55]
B
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 3x year over year rate and we've been doing it with like a remarkable level of efficiency measured by what,
- [17:07]
A
what's efficiency mean to you?
- [17:08]
B
Just, just like, you know, annual burn figures. And it's funny, we're doing it in a space, right? 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, can get online and get achieving great results with one or two resources will require them, you know, year, multiple years with 30, 40, 50 resources dedicated to that one account, building the bespoke solution for them. So part of it is that like their economics demand that level of capital. But 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 going to get a customer, we're going to treat them right, we're going to deliver everything we told them that they were going to deliver and then they're going to tell their friends. Friends about it. And inside of these industries it's small networks and, and trust is sort of the ultimate currency and it makes for a business that can grow really quickly that's also not going to burn a tremendous amount of money.
- [18:07]
A
I'm trying to get a sense of like when you really hit it. So you did the 8.5 million first seed round in 2021. Did you still have some of that money in the bank, you know, going up when you just did the 20 million Series A in Jan 2026?
- [18:16]
B
Yeah.
- [18:16]
A
Okay, so the bank was never so low where you considered shutting the company
- [18:19]
B
down, not after the pivot. So we had 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]
A
2021 is what you call the pivot, right?
- [18:36]
B
No, so I'm talking about 2018 when we left the ride share 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 like critical moments that, you know, fork in the road that could have gone either way. And then during COVID we were serving the transportation industry and transportation shut down. Right. It was the first thing that shut down. So we saw overnight 80, 90% of our revenue. Right. Usage based model came back and you know, nipped us in the behind. We saw 80, right. March of 2020, it all disappeared. 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. And then we came out strong on the other side. We took that step into retail as that second larger industry and we were able to go and raise that, that first big round of funding. And since then it's been a pretty, you know, off to the races, steady
- [19:45]
A
climb time, is it fair to say, since 2020. The pivot was in 2018, 2021 saw you go into e comm. Now you have two markets. You use that traction to show investors that's how you got the 8.5 million dollar round done. You must have had some revenue traction at that point. Were you around a million of ar, you think back then?
- [20:01]
B
Yeah, we were just over that. Yeah.
- [20:03]
A
Okay, there you go. Okay. And then basically it sounds like you've had pretty exclusive, explosive growth since then. Something like 200 or 300 year over year.
- [20:09]
B
That's correct, yeah.
- [20:10]
A
Okay, super interesting last question here before we wrap up because I want to 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 go out to, you know, M and A folks, reach out and say, hey, instead of raising around injecting your valuation, would you consider a $200 million all cash offer from X Company from Intercom, right. To merge. Did you have any M and A offers aligned with the Series A process or no?
- [20:31]
B
Yeah, they always do align. You're 100% right. And yeah, they're, they're coming across our desk. I think that, you know, 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, you cut
- [20:51]
A
that off your story, by the way. I just want to point that out. You cheated a little bit. You cut off 2016-2018 on your LinkedIn. All the hard work, right? You sort of said, let me just put 2018 as a start date. But the hard shit was before that in some way.
- [21:02]
B
I mean, 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, 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. 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, I, you know, it, it's a whole nother level in the way that you can think and in the amount that you can go and get done. So very long way of saying, you know, for Sam and I like it. It's never been more fun than it is right now. And what, what in, you know, what are we going to do? We're going to sell it and then we're going to go back to the beginning and start from nothing again. I think all of it was to have the opportunity to go and, and, and sort of live this next stretch and, and build the business. So, yeah, I mean, we're all like.
- [22:01]
A
So just to be clear, you're past, you know, eight figures of revenue, call it 12 million of revenue. If someone came and offered you 150 million, all cash up front today to sell the business, you and Sam say, no, thank you.
- [22:11]
B
Yeah, no, thank you at that figure.
- [22:13]
A
I love it. I love it. All right, last question. I'll put some pressure on you. You can say no, but I'm going to ask it anyway. My audience expects it. 20 million, series A. What value? What, what valuation?
- [22:21]
B
Brian hanging out right around 100 million in valuation.
- [22:24]
A
Was that higher or lower than you expected when you started the process?
- [22:27]
B
Us? 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, you know, it's the classic wisdom, right? It's more important who you're working with than like 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 we're sort of off to the races now.
- [22:53]
A
Brian, can I. Would you. Am I allowed. Can I put a 20k check in that? On the same terms? I'm a distribution guy. Like, I'm, I'm a. I'm a distribution channel. You have Spamming Zero podcast. You know, the power of distribution. Let me put in 20k. Same terms.
- [23:04]
B
Yeah, spamming zero. Look, you were really doing your research, that's all. That's offline chitchat, Nathan.
- [23:09]
A
All right, well, hey, listen, you're. You're a real pleasure to interview. I appreciate the time. If people want to follow your journey online, where can they find you?
- [23:15]
B
I'm a sucker for LinkedIn. For better or for worse, 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.
- [23:27]
A
And yeah, guys, 2016 ride sharing app at Cornell with his best friend Sam realized I 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, NY and help them get their inbound calls resolve faster? That's exactly what they did. 2021 they really started figuring out added a second industry, Tory Burch's E Comms of the world and ultimately use that revenue. Traction past 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 3x year over year the past three years. That traction enabled him to drive a very competitive series A process. 20 million closed in Jan. Of 2026. Just a couple of months ago. Healthy valuation approaching 100 million bucks. And he's not 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 U scale and help use them to get your calls answered faster. Right now, again focused on healthcare, retail, ecommerce 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. Click here to watch the next episode. Right now.