Andrew Warner is a founder, a long distance runner, and a scotch/bourbon drinker. He’s known for creating Mixergy, an education site for startups, featuring content from the founders of Y Combinator, Airbnb, and Pixar, among many others. His latest launch is Bot Academy, which helps companies set up chatbots on Facebook.


In This Episode

All businesses will have their ups and downs. In this episode of MODERN ONTRAPRENEUR, Landon Ray sits down with Andrew Warner to discuss what it’s like to experience the lowest lows and how to persevere, how chatbots are the future of marketing, the longevity of podcasting, and how growing up in New York shaped Andrew into who he is today.

Topic Timeline:

1:10 ChatBots

The hottest thing on the market.

2:10 It’s About Heart, Not Numbers

Care about the people: your employees and customers.

5:55 Landon’s Big Fire

Rebuilding the non-scalable product from scratch defined him.

8:47 New York Upbringing

Massively successful people all around breeds competition.

9:26 Curiosity and Interest

Curiosity and interest in other people builds bonds and relationships that last.

11:13 Mixergy

Andrew will podcast and interview people until the day he dies.

12:01 Reputation

With experience, comes a reputation that will bring in high-end people with huge fan bases.

14:30 Getting Chatbot Subscribers

Experimenting with the latest tech to learn how to build a better list.

18:12 Timeless Advice

Our podcasts will outlast us; it’s important to be relatable so you can influence people long after you’ve moved on.

19:59 Don’t Play House

Once you start, the pretending is over: it’s not a game anymore.

That is the insane, never-ending work. … And you know what? To find purity in that, to find joy in that. That is what it is to be an entrepreneur.

– Andrew Warner

Show Transcript:

LR: Hey, I’m Landon. Welcome to MODERN ONTRAPRENEUR. Today, I have the great Andrew Warner. He’s a founder, he’s a long distance runner, and a scotch drinker, bourbon drinker. He’s known for creating Mixergy, an education sight for startups, featuring content from the founders of Y Combinator, Airbnb, and Pixar, among many others. His latest launch is Bot Academy, which helps companies set up chatbots on Facebook. If you see him, ask him to join you for a run or a scotch.

AW: Oh, yeah. Oh, man. Is it weird that I’m drinking, by the way, a whiskey before noon here?

LR: No. You’re not supposed to tell people it’s before noon. They wouldn’t have known.

AW: I want to tell them, I just came off stage. There’s so much pressure, I want to do a good job for you. I followed ONTRAPORT for years. You guys invited me to speak here. Once the pressure was done, I usually wouldn’t drink until way later. I said, “You know what? I need a little something,” and it felt great. It felt great to talk to the audience. It felt great.

LR: Good, and you talked to them about Facebook chatbots?

AW: Yeah, I’m kind of obsessed with it right now.

LR: Yeah, so you want to tell us about that real quick?

AW: Yeah. What I’m noticing is that when I talk to my wife, I use email to communicate with her, but I also send her iMessages. When I talk to someone on my team, I use Slack in addition to email. When I talk to others outside of my team, I’ll use Facebook Messenger in addition to email so I thought, “Why am I only using email to communicate with the people who I want to sell to, with my customers? Why shouldn’t I also try chat apps?”

And so the idea of chat bots is that they enable businesses to reach people using messenger apps just like they would via email. And so that’s the future. That’s what I’m so gung-ho about that I came here to speak, and created a whole new business around it.

LR: It’s awesome. Everybody’s talking about it all of a sudden. The last six months, it’s just like….

AW: I know! A year and a half ago I was talking about it, people said, “Bot what?” And they weren’t paying attention. Suddenly now everyone wants a chatbot.

LR: And it’s interesting. In the last couple weeks, I had it happen to me the first time. So it’s coming, isn’t it?

AW: Yeah, it is.

LR: But before we get into that, let’s just take it back a second. You’re the founder of Mixergy, a very well known, a very successful startup in the valley there, right?

AW: Yeah, we’re in San Francisco.

LR: How long ago did you start that?

AW: ’08.

LR: ’08.

AW: Yeah. I thought I was going to start it and run it for the rest of my life, and I will.

LR: If you could go back to ’07 and give yourself a tip based on what you’ve learned since, what would it be?

AW: You know what, it’s painful for me to even think about it and talk about it, but here’s the thing. Before that, I had an online greeting card company. We did about 35 million in sales. All I cared about was numbers. I would walk in every day and I could see to the minute how much money we made. I was that obsessed with it, how many dollars per minute. After we sold that company, I said, “You know, I care too much about numbers. I should care just about heart. I shouldn’t care about numbers at all.”

If anyone told me I should care about the number of subscribers to my podcast, I’d go, “No, I don’t even know the number.” How many people on your mailing list? I didn’t know the number; I didn’t care about it. Big mistake. I somehow got it into my head that you’re either a mercenary who cares about nothing but numbers, and you walk into the office, and you see a number every day, and that’s your value as a human being, as a man. That’s true. That’s the way it was for me.

Or, you don’t care about it at all and you just care about people. All I cared about for a long time was just how good a job am I doing with my conversations and my podcasts, the quality and the courses that we were doing on Mixergy, the quality of the guests, and I’m very proud of the people we had, and still do, to teach on Mixergy. I should have cared about numbers. I think it’s important to have a couple of metrics that you care about, and to maybe not obsess about them to the point where that’s your sense of self worth, but closer, closer to that than I was in the beginning. So if I could go back to when I started, that’s what I would do.

LR: So, we have a bunch of numbers, as you can imagine. My concern would be that if we focused on one number that it would be hard for every team member to be able to see how to translate a problem there into an action that they can take. How would you….

AW: So what do you do, then? Do you give everyone all the numbers?

LR: Every day we have this thing called Daily Stats that comes out and it’s actually a chart of, I think is it nine metrics, or twelve? It’s actually well organized. So, we have three key focuses in our business, and there’s three stats, I think, for each focus, and then each team is kind of responsible for a particular stat.

AW: And then everybody in the team knows, everyone in the company knows how well they’re doing.

LR: Yeah.

AW: I see. You know what? I think that makes sense, but I find that having one number that the whole team rallies around is really helpful, so we’re all working to get towards something. You guys don’t do that? You don’t say number of new subscribers, new customers, number of email subscribers? Is there one that you guys are using as a rallying point?

LR: I think probably that the bottom line that everybody knows is that MRR is the bottom line.

AW: Because MRR, then, is reflective of how well you’re doing with your customers.

LR: It’s new customers, it’s retention, it’s expansion. It’s kind of like the whole ball of wax.

AW: Yeah, yeah, yeah, all right. So, do you identify with that number? Does that feel like if you’re having a bad MRR graph, that you’re not a good person? Whether you’re not being as good a person as you could be? Do you internalize it the way that I did?

LR: I don’t think I do. But I’ve been at this for a couple of minutes now. I’ve seen fire and I’ve seen rain.

AW: I see.

LR: And so I’ve kind of been through bad months and good months. Also, I have a bunch of employees. There’s a lot of stuff that goes into making that number work, you know what I mean?

AW: It sounds like you’re much better adjusted than I was.

LR: Well I think that happens over time right? I think that I definitely was probably more concerned ten years ago.

AW: Okay and what happened that turned you around?

LR: Just getting beat up a bunch of times.

AW: It sounds like there was a big fire.

LR: Look at this, this guy’s turning it around.

AW: Of course. What was it?

LR: You can’t interview an interviewer. “What was the thing? What was what?”

AW: What was your big fire? The one that actually just become who you are? That made you realize, “You know what? My number isn’t who I am and I’m stronger than the number and also when the number is great, I’m not infallible.”

LR: In the early part of the decade, 2010, we got a bunch of traction, 2009, business took off. We realized the software wasn’t scalable. We had to rebuild it from scratch basically. And it took us a long time because it was a nights and weekends project. We put everything we had into it. We relaunched it in early 2014, took forever. And it looked good for a couple of months. Sales tripled when we launched this thing. We hired 25 people in one day. And then the wheels came off. The whole thing started smoking and….

AW: Because the software wasn’t working?

LR: Yeah, we had some initial troubles that lasted about four months. Four, five months. We call it the shit storm, was that period of late 2014, and a bunch of stuff went wrong all at once. We had gotten ourselves overextended. We’re a bootstrap business so we don’t have money to burn, and we took a gamble hiring 25 people, and immediately it blew up in our faces. We had basically a year of very low growth, which we’ve been a super high growth company. So 2015, we kind of hurt our reputation, it took us a minute to fix the software, then it took us a longer minute to rebuild our reputation.

AW: You know what, I remember that. I remember the Facebook comments about it. Right, this was pretty public.

LR: Oh yeah, it wasn’t pretty.

AW: Yeah, right, and you jumped in there and I remember you responding and wow.

LR: No it was a disaster zone. And 2015, that turned into financial problems and this close to a round of layoffs. I mean, I aged 10 years.

AW: And so what did you do to get over it? Therapy? It’s not whiskey, you’re not a drinker.

LR: No, no it is whiskey it’s just….

AW: It’s 11 in the morning. What are we doing?

LR: Yeah, well, what I did is we buckled down and we got through it, and so we survived is what we did. Then we ended up thriving again and I think what it taught me was that A, to be more fucking careful. But also, you will live another day. You know what I mean? And a bad month doesn’t mean the end of your life. That was a tough year, 2015 too.

AW: That’s a hard thing for me, a bad month doesn’t … I thought if I even did poorly on stage here today, that could be the end of my life. There’s a very, like, if you screw up something bad could happen type of thing in my build. I don’t know what it is.

LR: Yeah, ambition is funny that way.

AW: Yeah it is. Right? I’ve learned to deal with it and to just like soften the blow, but there’s definitely a, “You’ve got to do well in this interview, you’ve got to do well on stage.” There isn’t some bad thing that’s gonna happen, but in my head there’s an overall badness that will happen if you don’t do well.

LR: Do you think that living in the heart of it all, San Francisco, Silicon Valley, contributes to that?

AW: No, I think it’s growing up in New York. No seriously, I grew up in New York with these highly, massively successful people all around me. My friends, some of them, their parents were these guys that you read about, right?

LR: Yeah.

AW: We’re talking about multi-millionaires at a time where I was thinking 20 bucks was a lot of money.

LR: Yeah.

AW: So you either think none of that matters, or you do what I did, which was to think, “How do I get to that level?” And to get to that level, especially New York style, you have to obsess. Right, so I was a 21 year old guy wearing a black suit with a black tie because you have to obsess. You can’t let yourself be unbuttoned like this. That’s the makeup that I come from.

LR: Yeah, interesting. So how did that turn into your … First of all what is your unique skill set? And how do you think that upbringing contributed to it?

AW: I guess it’s a handful of things. One, this just genuine curiosity that I developed over the years for other people is really helpful. It helps me with the people that I work with, understand where they’re going. It also helps me understand my audience, my customers, what they’re looking for. I do a podcast, tons of people doing interviews. You’re doing an interview right now, right? It’s really hard to compete in that space and my podcast still competes in it largely because I have this genuine curiosity. Like, you’re interviewing me, I can’t help but turn it around. So that’s a big one. And I find that when I take interest in people that it creates a connection, a bond, and a relationship.

LR: Being interested.

AW: Yeah, yeah, yeah. When I was a kid, I was really uninterested in other people. I cared only about money. And then I heard about Dale Carnegie’s How to Win Friends and Influence People so I read the book. How to Win Friends and Influence People is kind of a dorky title so I didn’t tell anyone. But I read it, and one of his big things is be interested in other people. Right? If you want to be interesting, be interested. I learned it, I got interested in other people, I cared about them, like genuinely started to find myself caring about other people.

And I loved it so much that I went … since I was in New York … I knocked on the door of Dale Carnegie and Associates, right in the heart of the city. And I was a college student, I said, “I’ll do anything for free. I just want to be around the people who are living this book so that I could live it more.” And they said, “We’ve got the right person for you to work for.” It was this guy there, Robert Reese, I’ll never forget his name, and he was an experimenter. He loved that I was willing to knock on the door. He wanted to experiment with ways of bringing Dale Carnegie’s ideas to other people. And by reading the book, by going through their class, because they gave it to me for free because I was working for them for free, and by experiencing it the way they did it, I learned empathy, I learned to understand how to talk to people, and it just changed me completely.

LR: So you rolled that into this interview series, Mixergy, which just blew up. And you’re still working on that?

AW: Still doing Mixergy.

LR: You just mentioned that you’re going to do that for the rest of your life?

AW: For the rest of my life. You’re going to see a 99 year old guy doing an interview with someone, yeah.

LR: Yeah, why?

AW: I’m so genuinely curious, and I can’t sit down with someone at dinner and say tell me about the time you were depressed, tell me about the time the wheels fell off, right?

LR: Yeah.

AW: All the curiosity that I have, I have to find a way to make it socially acceptable and bring it up at the right spots in conversation. But in an interview, no I don’t, right? I get to jump in say, “Hey, you know what, I was depressed once.” I did this with a guy just the other day. “I was depressed once, here’s what happened for me. How did you deal with it?” And suddenly I’m getting to talk to the best of the best people about their most challenging times. It’s insanely fortunate.

LR: Yeah. And what’s working for you right now, in terms of growing that business?

AW: The biggest thing for that is, to be honest, because we’ve done this for so long as a team, the reputation is tremendously helpful. We now get guests who we couldn’t reach otherwise. I had Justin Kan, not just to do an interview though we did it, he also came on to teach a class on Mixergy about entrepreneurship. He’s the guy who founded where you can go and watch people play live video games. Seems silly, sold it for about a billion dollars to amazon, right? I asked him, “Why are you doing this? Why are you teaching on my platform?” And he said, “I’m teaching on Mixergy because I used to listen to it when I was building my company.” So a lot of people grew up listening to Mixergy, started their businesses listening to Mixergy, built it with what they learned from other entrepreneurs and now they’re coming back.

LR: Yeah, longevity.

AW: That’s helping tremendously. If you’re looking for a tip that can translate to people who are watching us, the number one thing I have to say about interviews is, interview people who have big passionate followings. Their fans will find you, their fans are going to discover you, and then they’re going to stick around for other stuff.

LR: And then you’ve got your fingers in a lot of pots. Is Facebook Chatbot the thing right now that’s turning up volume across the board? Or what’s….

AW: You know what, a few years ago I got an email from a fan of mine, Wade, he said, “Andrew I’m a fan of yours, I know that you’re struggling to find people filling out your form to also get them to subscribe to an email list that you have. I’m creating a tool that will help you do that. Do you want to talk about it?” I said yes, he showed me the tool that later became Zapier, and I said I want it. And he didn’t have an account, he didn’t want to charge me. I said, “I’m going to pay you because I want you to build it.” I paypaled him 100 bucks and I became the first Zapier customer. And they built this tool up that connects anything. ONTRAPORT can connect to the chatbot program we use and so on. What I realized was that I have a really good fan base of people who are hard, charging, creative, entrepreneurs. Couple that with me being so interested in new technology that’s actually useful and actually will generate revenue, a real return on investment.

That’s told me that if someone in my audience creates something that I have to use so badly that I’m willing to pay for it, from now on I’m going to put some money into the company and I’m going to invest. And so I made some angel investments based on that. The latest one is many … Well not the latest … One of them is a company called ManyChat which I needed some way to communicate with people via chat. I tested and tried all platforms that were out there, this is the one that I liked. I got to know the founder, and then I said, “You know what, I’m going to invest. I’m not just going to be your first customer,” which I was, “I’m also going to invest.

LR: Awesome. And so what are you learning about right now? What’s kind of like your personal cutting edge?

AW: I think that there’s a land grab now for subscribers of chat and I’m trying to figure out how do you do it? How do you get more subscribers of a chatbot? How do you get those subscribers to also subscribe to email, right? How do you get your email people to understand right? That whole way of things working is something I’m insanely fascinated with.

LR: It’s so new. A lot of experimentation happening right now.

AW: Yeah. Yeah, yeah, yeah I mean, we were talking earlier about how someone who heard me talk about chatbots created a post on Facebook. Anyone who comments on it got a guide from him via Facebook Messenger and immediately Facebook Messenger said, “Can I also send it to you via email?” If you said yes, you typed in your email address and now you’re on his email list and on his chat list. He could communicate with you in both ways right? Longer-form messages that aren’t time-sensitive, he sends via email. Short-form messages that need action right now, he sends via Facebook message. Right, so the way that these two worlds combine is really interesting.

That’s the thing. We are marketers who are innovating and opening up businesses to chat. I invested in another company called Assist. They create these beautiful chat experiences. You can go in and buy flowers on Facebook Messenger. First, I can say via Facebook Messenger, “My wife’s having a birthday.” It’d say, “Okay tell me about your wife.” I tell him about my wife. It’d say, “Here’s some flowers we think your wife’s going to like.” I pick the one I like, I pay for it via Facebook Messenger. They built this, Assist did, the company I invested in, for 1-800-Flowers, their client that’s using the software.

Mark Zuckerberg, on stage, announced this whole chat platform. He shows this, says, “I love this.” Who goes to buy flowers on Facebook Messenger? No one. This technology will die unless a marketer like you and me and the people who are listening to you, are coming to this conference on Techapalooza unless we say … We have to put some marketing behind it. And if we put marketing behind it, we are going to pioneer it. Then, it’s going to become this thing that people really think about when it’s time for them to buy flowers. So marketers pioneer.

LR: They do.

AW: But I get your challenge and bring it up because I think it’s important to talk about it.

LR: Yeah the thing is, is that I have yet to get spammed via Facebook Messenger. But if marketers have their way….

AW: It’s impossible. It’s actually impossible to spam … You and I are friends, my business cannot send you a Facebook message. You can come to my house. You’re interested in my business while we’re having scotch at my house. The next day I want to follow up with you, my business cannot send you a Facebook message. You have to actively initiate it. It’s impossible, otherwise. So you have to actively initiate it and you can cancel at any time. Not by telling Andrew I want to stop, not by telling Andrew’s bot I want to stop, but by just swiping up and saying delete. You could also swipe up and report. Now you report someone to Facebook a few times, they’re done. This is an environment where you have to be a good actor or else you’re booted.

LR: So you think they’ve set it up well, and there’s not going to be additional regulations down the road?

AW: I don’t think there are going to be regulations because they’re setting it up just like I said. They’re setting it up really well. Now, if you’re not interesting … Today people will still read your stuff because it’s novel, right? Like the first TV shows, I watch them to this day, I think, “Who watched this thing?” But it was novel to see some pixels on a screen. Wasn’t even pixels right? You just see some lights on a screen that were funny or entertaining, so people watched that stuff. Today it’s not because stuff has gotten more sophisticated and it’s more targeted towards everyone.

So same thing is true with chat. Today I could send something that’s not really that interesting. I could send a photo of the two of us just kind of hanging out over here. People would say, “Oh, interesting.” Their bot could actually send this to me. Two months from now it’s going to be harder. Two years from now it’s going to be impossible. So we have to keep finding ways to be interesting, to engage people, to do more than just send them promotional material. And if we do that, they’re going to want to keep staying subscribed. If we don’t, we’re out.

LR: Interesting that you positioned yourself to be in the center of technology in the way you have. Did you anticipate that when you started doing interviews that you’d end up having the opportunity to angel invest in Zapier and ManyChat?

AW: What my dream was, and you can go back to listen to the early interviews, I said, “Look I’m going to work like mad to do these interviews right, with the idea that you will be listening to these interviews and build businesses based on what I do, what I say, what you hear these guests do. And then you’ll come back and do an interview.” So I didn’t so much want to be an angel investor; I didn’t want to do anything else. My vision was to do what Dale Carnegie did for me. Dale Carnegie wrote a book that influenced my life and influenced by business. I want to create an interview series that has that kind of impact on people. When you create a business based on some ideas that you’ve heard, it changes your life and then it impacts your customers, your employees. Think about all the people you’re touching. Think about that right? How many people work at ONTRAPORT?

LR: 110 or 120.

AW: Right, how many businesses are built on ONTRAPORT right? We can hardly count them right? This is insane amount of power that you have. The ability for me and my interview to contribute, to allow someone else to see that this is possible, to build a business. That is the dream. And podcasts are going to outlive us. What you and I are talking about right now is going to outlive us. I used to go back and read stories of Andrew Carnegie, right? The steel tycoon. And he shaped my life too. People are going to watch this stuff when we’re dead, even though the technologies we’re talking about are out-of-date, they will still see how did you think through your turmoil. How did I think through my numbers? Why did I adjust it? And if we’re relatable and if we’re real, then they’re going to be influenced by it long after we’re dead. And to me, that’s the dream.

LR: Yeah that’s exciting.

AW: It is exciting.

LR: Worthwhile way to spend your time. So we live in this pretty unique moment in terms of entrepreneurship. We named this thing MODERN ONTRAPRENEUR. What do you feel like the sort of unique opportunities and responsibilities are of being an entrepreneur today?

AW: To not play house. Do you have kids?

LR: I do.

AW: Right? Do you remember how much that changes things? Right, suddenly you’re not playing house, you can’t just go out when … It’s so easy as an entrepreneur to play house. And we’re not doing it in the old way that people used to do by buying business cards as soon as we start our company, but we are doing it in the sense of, “I’m starting a company, I’m an entrepreneur,” and the idea that I’m an entrepreneur is bigger than the work that you have to do to be an entrepreneur. And I think too many people are playing house. The work is a lot harder, the work of talking to your customers. You do it right? You’re talking to people here. I do it with my audience. What are they interested in on Mixergy? What are their problems? So we can bring in course leaders to help them with it. I see the founder of ManyChat who we both met, Mikael Yang. Mikael Yang is in Russia working with his developers at one in the morning, no joke, he’ll talk to me and then he’ll talk to people who are part of Bot Academy, where we train people to create chatbots, about our challenges with chatbots. About where we see this going.

That is not playing house as an entrepreneur. That is the insane, never-ending work. Hours that most people don’t know exist, they sleep through them. He is up working, you are up working. This is the idea. And you know what? To find purity in that, to find joy in that. That is what it is to be an entrepreneur. So anyone can go out and buy sneakers but not everyone can hit that four mile mark. And every January, we’re going to see this in January, roads are going to be, especially here in Santa Barbara, filled with people. Brand new sneakers, brand new running clothes, “This is the year right?” Playing house by buying that is really easy. Going through mile four is hard. Suffering through mile four and then saying, “This is the pain, this is the work.” That is a challenge. And so that’s the big thing that I’d say a modern entrepreneur needs to understand because we’re full of these “fake-os” out there, the people who are pretending right? If I was a pretend rapper, you’d understand that I was a pretend rapper in a second. You’d hear me rap, you’d see me with weirdo backwards hat right?

It’s a little harder to spot the fake entrepreneurs, but they exist and there are a lot of them and we need to stay, as modern entrepreneurs, focused on the business, on the work, on the clients, on the stuff that nobody is going to praise. On that being up at 1:00 talking to a customer, on that sweating it, the equivalent of a four mile or eight mile and still saying, “I love this, I’m going to do this. This is the pain that I signed up for.”

LR: Awesome.

AW: Yeah man.

LR: Andrew, thank you so much for being here. This was great.

AW: Thank you. Thanks for having me.

LR: Will you sign our wall?

AW: Yes.

LR: Appreciate it



Check out the previous episode featuring Chris Winfield of Super Connector.

About Ben Cogburn

As ONTRAPORT’s Traffic Manager, Ben Cogburn spends most of his time in our parking lot. Just kidding, he’s our resident digital advertising guru. As a geology enthusiast, Ben graduated from the University of California, Santa Barbara with a degree in Environmental Studies. So to say that he likes rocks is an understatement. You can find Ben hanging out with his rock collection, playing video games or hunting down new figurines to add to the impressive display he has on his desk.