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SaaS Interviews with CEOs, Startups, Founders

Flip Reaches $12M ARR with AI Voice Support for 250 Brands

SaaS Interviews with CEOs, Startups, Founders

Nathan Latka

Entrepreneurship, Business

4.6701 Ratings

🗓️ 22 April 2026

⏱️ 25 minutes

🧾️ Download transcript

Summary

How do you pivot a banned college ridesharing app into a voice AI company handling 300 million customer service calls?

Brian Schiff is the co-founder and CEO of Flip, a verticalized AI voice assistant that automates customer service calls for transportation, retail, and healthcare brands.

After realizing their Cornell ridesharing app was a dead end, Brian and his co-founder Sam pivoted into voice AI. Today, Flip automates up to 90 percent of routine support calls for over 250 enterprise companies and recently raised a $20M Series A at a $100M valuation.

You'll learn:

  • How to successfully pivot a failing startup model
  • Why verticalized AI beats horizontal platforms
  • How to implement usage-based pricing at $1.50 per call
  • Why "listen mode" is their best sales tactic
  • How to maintain 75 percent gross margins with AI
  • Why they rejected a theoretical $150 million acquisition offer
  • How to select the right industries for expansion
  • Why competitive B2C markets are best for AI tools

Brian started his entrepreneurial journey at Cornell's eLab accelerator. He navigated the near-total collapse of transportation revenue during the pandemic to build a highly efficient business growing 3X year over year.

Watch this episode on YouTube: https://youtu.be/gtFt5exyCaI 

Connect with Brian:  https://flipcx.com/

Connect with Nathan:  https://founderpath.com/ 

Transcript

Click on a timestamp to play from that location

0:00.0

Can I take 250 customers times the minimum ACD range you gave me earlier, 50 grand a year?

0:04.6

If that put you again well into the eight figures, 12.5 million AR run rate. Is that the right directionally? We are north of that. 20 million Series A. What valuation, Brian? Hanging out right around 100 million in the valuation. Because the bank was never so low, were you considered shutting the company down? Not after the pivot. Before we made the pivot, We had scraps.

0:21.1

We had a couple of customers in these small towns doing the ride share thing.

0:24.5

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. Someone came and offered you $150 million all cash up front 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 Red Route, 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're ready to take us to the top?

0:54.8

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, right, Sam and I met a decade ago, my co-founder. We were freshman 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.

1:13.7

But they were banned in upstate New York.

1:15.4

We were going to school at Cornell.

1:17.0

So I think we were just looking to build.

1:18.8

And that was an easy place to start.

1:20.8

It was sort of a product that you knew everybody wanted.

1:23.5

And it was a gap in the market.

1:25.4

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 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 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 Yor and Sam's history. So the website header says automate your customer support calls with voice AI. Is this broad or a specific

2:01.2

niche? Tell us what the product does today. Yeah. So I think when people read, AI is the technology

2:06.1

of our lifetimes. And when you look at the opportunities that people are zeroing in on to use AI

2:11.0

inside of a business environment today, there are two big use cases people are pointing to. The first one is

2:15.9

AI coding and the second one is AI

2:17.7

customer support. So we are in this massive opportunity space of AI customer support. And there

2:23.7

are two approaches that exist right now. There are these generic horizontal platforms that are

2:29.2

really going after companies in any industry. And then there are these hyper-focused,

2:33.4

verticalized industry solutions,

2:35.1

and that's the bucket that we're in. So we started in the transportation space. We have added

2:39.4

retail and healthcare over the last couple of years. But it is a very deep verticalized solution

...

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