Speaker 1: You're listening to Math and Magic, a production of I
Speaker 1: Heart Radio. If you know something's good, you know it,
Speaker 1: and the data says it's not that good. I still like, okay,
Speaker 1: So the dad has got to catch up because I
Speaker 1: know it's good. And sometimes there's something that I know
Speaker 1: isn't very good and the data would say that audiences
Speaker 1: love it, and I would go, there's no way. This
Speaker 1: is just like, audiences don't love this. I get that
Speaker 1: there's a lot of views, but this is not the thing.
Speaker 1: So will you go with your gut? And that's what
Speaker 1: I will go with my gut. Welcome to this episode
Speaker 1: of Math and Magic. I'm Bob Pitman, and we're looking
Speaker 1: at stories from the frontiers of marketing today. Ben layers
Speaker 1: our guests. On first impression, you look at Ben, you
Speaker 1: might say, wow, this is a pretty cool guy. He
Speaker 1: must be a magician creative time for those who have
Speaker 1: worked with him quickly find out that he actually lives
Speaker 1: on the math side of the equation too. Regarding good business.
Speaker 1: Ben as the CEO of Group nine Media, which includes
Speaker 1: his first tech media venture and the place where he
Speaker 1: made his mark through a list. It also includes Now
Speaker 1: This Seeker and the Dodo, which was founded by his
Speaker 1: super smart sister. Is he family business? Full disclosure. I've
Speaker 1: known been or back then he was known as Benji
Speaker 1: Dare I say that? And I've known him since he
Speaker 1: was very young. His dad and I are very good
Speaker 1: pals and have been for a long long time. His
Speaker 1: dad's super smart, overachieving jeans must have worked somewhere there,
Speaker 1: and we've all had some wonderful adventures together. And Pilot Group,
Speaker 1: which was my private equity fund, backed through a list
Speaker 1: in the early day. So I've been able to see
Speaker 1: Ben through this whole thing and been so impressed with
Speaker 1: so many years. So they'll leave anything out. You didn't
Speaker 1: mention how handsome I am, But well, I assume we'll
Speaker 1: get into that. No one can see this. Let's move
Speaker 1: to you in sixties seconds. Don't think too long to
Speaker 1: say the first thing that comes to your mind. Okay,
Speaker 1: I can do that. Do you prefer pizza or tacos?
Speaker 1: Pizza sweater or hoodie sweater? Unfortunately I've gotten old. You
Speaker 1: have gotten old. I'm embarrassed. This is going poorly. iPad
Speaker 1: or Kendall Kindall New York or Philly, New York Mets
Speaker 1: are Yankees, Mets Ninja's or Pirates Ninja's sunrise or sunsets.
Speaker 1: Sun sets. I like a sunrise, but I don't get
Speaker 1: them as off only when you stay up all night exactly.
Speaker 1: Secret talent, secret talent when we were in college, and
Speaker 1: I can, I can, I give a longer instwer. So
Speaker 1: when I was in college, I we did talent shows
Speaker 1: and I did them with Bo your son, and my
Speaker 1: secret talent was balancing a broom on my finger because
Speaker 1: I didn't have any secret talents. That is a pathetic
Speaker 1: thing to admit, but that's true. Place to go to
Speaker 1: find out who you are. Back home with my family,
Speaker 1: smartest person you know, not your dad, my wife for job.
Speaker 1: First job was working for Andre Blas at his boutique
Speaker 1: hotel company. Historical idol Alexander Hamilton came to mind. So
Speaker 1: I guess I'll go with that favorite company you've invested in,
Speaker 1: not necessarily the most profitable, favorite company, the company that
Speaker 1: I have the closest relationship with his Casper Mattress company.
Speaker 1: Favorite company wish you had invested in but didn't. Well,
Speaker 1: we've passed on lots of great companies. I think probably
Speaker 1: the one that I feel silliest about is Harry's only
Speaker 1: because I'm friends with Jeff who would play you in
Speaker 1: the movie of your Life, the guy who played Jesse
Speaker 1: and Breaking Bad. Favorite smell pizza? No, my favorite smell
Speaker 1: is my kid's best live concert. Obviously I heard music festival.
Speaker 1: Who I love that? What topic can you talk about forever?
Speaker 1: The media business or my kids again? Okay, so let's
Speaker 1: get into you. Tell us about starting thrill List. I
Speaker 1: don't get to think about this very often. It's also
Speaker 1: appropriate that I'm doing with you. So starting thrill List
Speaker 1: was I think the way a lot of businesses get started,
Speaker 1: as somebody build something that they want to exist for themselves.
Speaker 1: I was new to New York, working in a job
Speaker 1: that was interesting, but I knew wasn't necessarily where my
Speaker 1: sort of heart was in the long term, and I
Speaker 1: became sort of enamored with the idea that there wasn't
Speaker 1: a city guy that spoke my language. You know, my
Speaker 1: mother and I read the same city Guide to make
Speaker 1: a decision about where we would go and what restaurants
Speaker 1: we would eat at, or you know, things that we
Speaker 1: would experience. And this was at a time when there
Speaker 1: was a cultural shift happening where people were moving from
Speaker 1: really valuing what you possessed towards valuing what you did
Speaker 1: and the experiences that you had. And I felt that
Speaker 1: I needed better information and more trusted information, and more
Speaker 1: personalized information about how to spend my time and money
Speaker 1: and started writing terrible, really terrible emails to friends about
Speaker 1: stuff that I discovered that I thought was fun. I
Speaker 1: did it with a college buddy, you know, one of
Speaker 1: my good friends from school, Adam Rich. He and I
Speaker 1: would go out and have drinks and eat food and
Speaker 1: do silly stuff and record it and send it out
Speaker 1: to people, and we actually started to get a little
Speaker 1: bit of a following, and people started doing the things
Speaker 1: that we would recommend, And so we write about a
Speaker 1: restaurant and the place would have a line out the
Speaker 1: door the next night. We started to think it was
Speaker 1: sort of interesting that people were taking our advice. Only
Speaker 1: then started to do a little bit more research on
Speaker 1: what a business model might be, and unbeknownst to us,
Speaker 1: came across Daily Candy, which had built a very large
Speaker 1: business doing the exact same thing for women, and unbelievably
Speaker 1: we didn't a at first know it existed and be
Speaker 1: didn't know that it was owned by you, which is
Speaker 1: the most insane and sort of serendipitous and funny and
Speaker 1: bizarre way to come to something. The next thing we
Speaker 1: did was called you and said can we come over
Speaker 1: and get your advice. We know Daily Candy has been
Speaker 1: super successful. We've built this email list for guys that
Speaker 1: is doing something similar, albeit at a pathetically small scale.
Speaker 1: And you took interest in what we were doing, and
Speaker 1: you know, the rest is history. You know, it's interesting
Speaker 1: because maybe I've never told you this. Everybody kept coming
Speaker 1: and saying, we want to do Daily Candy for men,
Speaker 1: but they all wanted to be about fashion and things
Speaker 1: that women are interested in. You and Adam came in
Speaker 1: and what sort of I think blew us away was
Speaker 1: You said, no, no, no, no, no, that's not what
Speaker 1: men are interested in. That's what women are interested here's
Speaker 1: the equivalent for men. Can you tell us a couple
Speaker 1: of those things that you covered, Like Daily Candy, you
Speaker 1: covered sort of one thing per day, one thing per day.
Speaker 1: Tell us about a few of them. I mean, look,
Speaker 1: we were not scientists. Let's call us spade to spade.
Speaker 1: I think our first article was about a Mexican restaurant
Speaker 1: that had been open for several years that we wrote
Speaker 1: about as if it was a brand new thing, because
Speaker 1: it was Sinco de Mayo, but it was new to us,
Speaker 1: and I guess it was new to enough people that
Speaker 1: people took interest in it. When we started to really
Speaker 1: get our feet under us is when restaurants or new
Speaker 1: places that opened started to understand that we were we
Speaker 1: were able to move audiences, and so we went from
Speaker 1: having to sort of curate what existed into getting access
Speaker 1: to things before other people knew about them. And so
Speaker 1: at that point, where was a daily email was something
Speaker 1: where if you were really curious and you really wanted
Speaker 1: to be on the cutting edge of what was happening,
Speaker 1: we sort of became a must read because we were
Speaker 1: providing breaking information. It wasn't breaking political news. It was
Speaker 1: a taco stand was opening, But if you were really
Speaker 1: passionate about living that kind of life, we were able
Speaker 1: to bring you that information first. And then we were
Speaker 1: maniacal about creating a brand and a persona that was
Speaker 1: different than the way that other people covered the category.
Speaker 1: And if we wrote about a restaurant the same week
Speaker 1: that New York Magazine and New York Times and zag
Speaker 1: It and Daily Can and a bunch of other reputable
Speaker 1: places did, and if you picked up the thrill List
Speaker 1: review or the thrillst recommendation, you would immediately know that
Speaker 1: it was thrill List. After a while, we were able
Speaker 1: to package it up and build it in a repeatable,
Speaker 1: scalable way that enabled us to not have to edit
Speaker 1: every single piece of content ourself for myself, but create
Speaker 1: something that could be the voice of a brand, which
Speaker 1: you know, as you know, any great brand is all
Speaker 1: about what is that voice, what's that mission, why does
Speaker 1: it exist? And how can you make it something that
Speaker 1: even at scale, can be replicated. I think I remember
Speaker 1: it was either the Pitch or it was one of
Speaker 1: the first news letters you found flip flops that had
Speaker 1: a beer opener. It was called the Fanning. But every
Speaker 1: time I would read thrill List, I chuckled out loud.
Speaker 1: Our lawyer at our investment group came in one day
Speaker 1: and do you know what those guys are doing? They
Speaker 1: had a party last night and it was a hatchet
Speaker 1: throwing party. Do you remember that? Yes? I do remember this.
Speaker 1: That was sort of set that. I don't know that
Speaker 1: our lawyers would allow us to do that. At this point.
Speaker 1: We had a lot of fun. It was it was
Speaker 1: a different time. I mean, right, we like the world
Speaker 1: was a little bit looser. Who are you throwing hatchets
Speaker 1: at random party goers who signed nothing? They were on
Speaker 1: a wheel spinning and someone was just flinging hatchets against
Speaker 1: the wood behind them. Yeah, it was probably not a
Speaker 1: great idea, and first time investors ever called and said,
Speaker 1: you know, maybe this is not a good idea. So
Speaker 1: you were what major political science? Political science? Okay, political science.
Speaker 1: Guy had no real training in business. Yet you turned
Speaker 1: out very quickly to be this very astute CEO. And
Speaker 1: one of the things I observed was you made quick decisions.
Speaker 1: You would say we're gonna do this, and it's gonna
Speaker 1: happen here, and then two months later you go, they
Speaker 1: didn't deliver. I fired them. I'm trying again. You never
Speaker 1: hung on to these old ideas or what you hope for.
Speaker 1: You were very decisive. You help people to real clear standards.
Speaker 1: Where do you think you learned that from? Well, I
Speaker 1: don't know if that was a set up or not,
Speaker 1: but I quoted you as recently as this week on
Speaker 1: the twenty rule, which is an old thing that you
Speaker 1: used to talk about that I talk about all the time,
Speaker 1: which is this idea that twenty percent of the time
Speaker 1: the things that you do or the decisions that you
Speaker 1: make in business are obviously right. Immediately you hire someone
Speaker 1: who's a superstar, you launch your product that's a hit,
Speaker 1: and you know you have something good. And twenty of
Speaker 1: the time you do something that is very easy to kill.
Speaker 1: It's just not working and there's not a lot of
Speaker 1: emotional baggage with it. It's easy to sort of get
Speaker 1: out of the way. And sixty percent of the things
Speaker 1: that you do are somewhere in between, and you can
Speaker 1: rationalize why you're gonna keep doing them, and you can
Speaker 1: also rationalize why they're not big hits. And the advice
Speaker 1: that you gave early was get stuff out of that
Speaker 1: six and into one of the twenties as fast as
Speaker 1: you can, because the sixtent is what kills you. That's
Speaker 1: the stuff that it doesn't really deliver profit or it's
Speaker 1: vanity metrics, but it's not anything that really drives the
Speaker 1: substance of what's gonna power your business forward. And that's
Speaker 1: a philosophy that I have very much taken to heart.
Speaker 1: That's something that is an operating philosophy that we now
Speaker 1: have at Group nine around how we make decisions, which
Speaker 1: is mediocre stuff can't have a place here. That's something
Speaker 1: that you taught me, frankly, and something that I try
Speaker 1: to institutionalize in our business and sometimes succeeding, sometimes failed.
Speaker 1: I no idea. I thought you that I've always given
Speaker 1: you credits and wow, look at him here, but you
Speaker 1: know that, I mean, do you still talk about of
Speaker 1: course I do weed the garden. It's not a clear winner.
Speaker 1: It's a loser by definition. Instead of defining stuff that's
Speaker 1: not a clear loser as a winner, that's in a
Speaker 1: more concise way of doing it. Next time, I'll say that,
Speaker 1: how do you balance quick decision versus giving people, executives
Speaker 1: or whoever in your organization the time to make some
Speaker 1: mistakes and grow. There's not a rule that's a fuel
Speaker 1: one for me, which is if you don't actually think
Speaker 1: the person is going to get there, but it would
Speaker 1: just be really convenient if they did, you're probably better
Speaker 1: off ripping that band aid. You just have to sort
Speaker 1: of really be willing to give yourself a good look
Speaker 1: in the mirror. And by the way, I'm sometimes I'm
Speaker 1: very good at this, and sometimes I'm very bad at this.
Speaker 1: But how introspective can you be and can you really
Speaker 1: acknowledge when you're just delaying the inevitable? Others came to
Speaker 1: knock you off. You've got success very early with Thrillist.
Speaker 1: This was like wow product and up King Urban Daddy
Speaker 1: and a couple of others. How did you react to it?
Speaker 1: How did you defend your turf? It's a It's a
Speaker 1: good question. I think that we first and foremost the
Speaker 1: way that you defend is you just deliver a better product.
Speaker 1: For a long time, I think we delivered a definitively
Speaker 1: better product. I think there are actually moments where we
Speaker 1: you know, you hit a rough spot or a company
Speaker 1: gets a little bit of momentum, and there were times
Speaker 1: where I didn't know that we necessarily had a better product.
Speaker 1: But I think that we had the support of our
Speaker 1: investor base helping us whether more difficult times, which I
Speaker 1: am still a huge believer in. And I also think
Speaker 1: at the end of the day, a lot of this
Speaker 1: is just will power. None of this is rocket science.
Speaker 1: In particular the media business. If you're smart enough and
Speaker 1: you're able to get a group of smart enough people
Speaker 1: to sort of believe in something and work together you
Speaker 1: can will your way to success. We didn't have any
Speaker 1: tricks up our sleeve. This was just refusing to quit
Speaker 1: for a long time. You've always been open to a
Speaker 1: lot of ideas. I think initially looking at you, I thought,
Speaker 1: maybe that's good. You're young. But now let's see you
Speaker 1: at your age and you're still young, but not as young,
Speaker 1: and you're still open to new ideas. In that early period,
Speaker 1: what was one idea that you say that definitely worked,
Speaker 1: and what idea was one to say that definitely failed
Speaker 1: and why do you think that happened. One of the
Speaker 1: definite things that worked was a strategy around how we
Speaker 1: were going to go and expand market to market. It
Speaker 1: wasn't a novel idea. It was something that Daily Candy
Speaker 1: had done, but we were able to stamp out and
Speaker 1: repeat a process of how we would launch a market,
Speaker 1: how we would partner to accumulate subscribers pretty quickly, how
Speaker 1: we would leverage our existing advertiser base to support a
Speaker 1: new market that we launched. And so I think that
Speaker 1: we built a little bit of a machine to go
Speaker 1: and and expand geographically. That worked early on when did
Speaker 1: you realize through a list that arrived. I think I
Speaker 1: realized Thrillis had arrived when we got bigger than Daily
Speaker 1: Candy had ever been. That was certainly a moment, an
Speaker 1: unbelievable moment for us, when this thing that we had
Speaker 1: always aspired to be, we weren't able to use their
Speaker 1: blueprint anymore to grow because we had done what they
Speaker 1: had done. That was probably the moment. At the same time,
Speaker 1: I really have to admit I have moments where I
Speaker 1: think we've arrived, and then the goal posts move so
Speaker 1: quickly that it's very rare that I get a minute,
Speaker 1: even a second to really feel like we've arrived. But
Speaker 1: that moment when we passed Daily Candy, I think was
Speaker 1: one special one. I think when we created Group nine
Speaker 1: and merged brands together was another one. And now the
Speaker 1: best moments I get for sort of celebrating that arrival
Speaker 1: or success is when we when we have town halls
Speaker 1: actually so nothing external, but when we get time with
Speaker 1: the whole company and get to sort of take inventory
Speaker 1: on what we're doing and see everybody in one space.
Speaker 1: We do it every six months. We did it yesterday,
Speaker 1: which is why it stopped of mind. But those are
Speaker 1: really exciting and you know, slightly emotional to feel the
Speaker 1: momentum in the progress and where we're at. Those are
Speaker 1: now the moments, but they're fleeting. So advertisers, how did
Speaker 1: you so advertisers? Started out as the CEO running the company,
Speaker 1: but you also start out as the face to the
Speaker 1: advertising community. You were your time talking advertisers. Yeah, early
Speaker 1: on at least, how did you break advertising? Because you
Speaker 1: talk to people's starting businesses to get a little bit
Speaker 1: of consumer attraction and they can't seem to make money.
Speaker 1: You did and sort of surprisingly well early on? What
Speaker 1: did you do that you think is unique or responsible
Speaker 1: for them? And I think there are moments in time
Speaker 1: where things are easier or harder. I think when we launched,
Speaker 1: the Tide was a little different, and Daily Candy was
Speaker 1: this rising, exciting proposition. They had popularized email marketing for
Speaker 1: our consumer audience. They had pioneered the dedicated email and
Speaker 1: some formats that were really effective and that the advertising
Speaker 1: community leaned into. And so we got to ride those
Speaker 1: coattails very directly. I mean, the way that we prospected
Speaker 1: was we looked at people who were spending money with
Speaker 1: Daily Candy, and we went to them and said, we're
Speaker 1: doing that but for guys. And that was how we
Speaker 1: got a lot of our early business. And today you
Speaker 1: still spend that much time with advertisers. I spend a
Speaker 1: lot of time thinking about our advertising business. I spend
Speaker 1: less time out in market in specific meetings. I do
Speaker 1: it in chunk. So I'll do it, you know, when
Speaker 1: we're out and can or C s or. But my
Speaker 1: team is incredible and so thoughtful and so creative. You know,
Speaker 1: I can still add my value here and there through
Speaker 1: a list has gone from frat boy humor would throw
Speaker 1: hatchets at people at our parties. Two. I hate to
Speaker 1: use this word sophisticated. Well let's not. I would also
Speaker 1: hate for you to use that word. Okay, let's think
Speaker 1: of something else other than sophisticated. But it's certainly evolved. Yes,
Speaker 1: How do you evolve the brand like that without leaving
Speaker 1: your consumers behind or replacing one audience for another. It's
Speaker 1: something that we struggle with and talk about a lot,
Speaker 1: particularly these days. It's something that's just front of mind.
Speaker 1: The brand grew up for a while with us, just
Speaker 1: because we didn't know how to stop it from growing
Speaker 1: up with us. At a certain point, the company got
Speaker 1: bigger and we went into other businesses and I let
Speaker 1: it go. It was no longer you know, a reflection,
Speaker 1: a reflection of me, thank you. That was what I
Speaker 1: was looking for. The things that we realized over time
Speaker 1: were the lifestyle that we were promoting and celebrating was
Speaker 1: again it was about experiences and about every day being
Speaker 1: better than the last, and doing the stuff that you love.
Speaker 1: That's not for guys, that's just for people. That's a
Speaker 1: much broader audience. And so when we realized that our
Speaker 1: mission was one where we didn't have to contort it
Speaker 1: in order to make it applicable to a broader audience,
Speaker 1: we gave ourselves permission to let it be for a
Speaker 1: broader audience, and that has served us well. Just hold
Speaker 1: on a second, because we've got so much more to
Speaker 1: talk about. We'll be back after a quick break. Welcome
Speaker 1: back to Math and Magic. We're here with Ben Lair.
Speaker 1: You have a bigger than life dad, Ken Larry. He's
Speaker 1: a chairman of BuzzFeed, Blade, and god knows what else.
Speaker 1: He has always been on the cutting edge. He Foundedfington
Speaker 1: Post with Arianna Huffington. He was in the c suite
Speaker 1: at a O L and it's Heyday at time one
Speaker 1: or two before that, he had a huge communications company,
Speaker 1: and indeed he was working with Microsoft and Bill Gates
Speaker 1: when they sort of became icons. Right before I go, well,
Speaker 1: what did you learn from your dad? He's really good
Speaker 1: at just cutting to the core of an issue and
Speaker 1: doing away with a lot of the waste and getting
Speaker 1: to what's important. And so that's something that I try
Speaker 1: to do as well. So that's the thing in business,
Speaker 1: But you know, the business advice is secondary. The thing
Speaker 1: that I've taken from him is how to prioritize business
Speaker 1: visa v. Your family, Because I'm a much better business
Speaker 1: person when business comes second. If I'm settled with my
Speaker 1: family and I put my kids to bed every night
Speaker 1: and like in that rhythm and and always putting family first,
Speaker 1: then it allows me to put business in a much
Speaker 1: healthier place and make much more rational decisions. So your
Speaker 1: dad was, I know, a great role model for you there.
Speaker 1: The family always came first to him. Um and when
Speaker 1: your mother was away, uh, he would sneak you off
Speaker 1: to mc anmods to have the forbidden foods. True. Talking
Speaker 1: about your family, how do you think about work family balance?
Speaker 1: And what do you recommend to the people you work
Speaker 1: with and the people who you give advice to. I
Speaker 1: don't have a specific like here's how you should spend
Speaker 1: your time, but I would just say that family needs
Speaker 1: to come first. For me, what that means is I
Speaker 1: put my kids to bed. I'm with them every morning,
Speaker 1: and then I put my kids to bed four out
Speaker 1: of five week nights, and then by the way, I
Speaker 1: go back out. So tonight I will go home, I'll
Speaker 1: be home before seven o'clock. I'll put my kids in bed,
Speaker 1: I'll have half an hour with them, and then I
Speaker 1: have worked dinner. But that for me is like a
Speaker 1: really important thing that grounds me. And also and with
Speaker 1: my kids at seven in the morning, I don't want
Speaker 1: to say I'll see tomorrow. That's how I've built my
Speaker 1: calendar and how I've structured my work life. And I
Speaker 1: have two jobs investing in running Group nine. You know,
Speaker 1: my days are booked to the second and I book
Speaker 1: my family into that day. It's really easy to just
Speaker 1: let the calendar fill up and not make that a priority.
Speaker 1: But that's something that I won't I won't do. Do
Speaker 1: you put your phone away when you're with family? Yeah?
Speaker 1: I try to, and there are days when I forget
Speaker 1: to do your kids remind you? My kids don't remind
Speaker 1: me to put my phone away, except my kids want
Speaker 1: to pull it out of my hand and play with it,
Speaker 1: which is very depressing. We live in a confusing world
Speaker 1: right now. The addiction of technology is is horrifying, and
Speaker 1: so I really have to set boundaries for myself. I
Speaker 1: don't sleep with my phone in my room anymore. Do
Speaker 1: you have an alarm on your phone? No, I have
Speaker 1: an alarm clock. I'm like, what from blood eyed? I
Speaker 1: hope it's a clock radio. It's a clock radio, except
Speaker 1: I don't know how to set it, so it just
Speaker 1: goes set it to Elvis Duran in the morning, or
Speaker 1: the Breakfast Club or one of our other great shows
Speaker 1: here in New York. And so about ten years ago,
Speaker 1: INC Magazine picked you as one of their thirty under thirty.
Speaker 1: But it was also about the time you started Layer
Speaker 1: of Ventures with your dad. Tell me about starting that
Speaker 1: and how you weave that into your jay job. Running
Speaker 1: thrill list. New York was at an interesting point ten
Speaker 1: years ago where New York wasn't a TechTown yet and
Speaker 1: I was starting thrill lists and my dad had started
Speaker 1: huf PO as you mentioned, and my dad actually just
Speaker 1: had a super interesting insight, which was your friends or
Speaker 1: my friends were leaving good schools and instead of wanting
Speaker 1: to go and work on Wall Street or work in consulting,
Speaker 1: they wanted to go work at startups or start companies.
Speaker 1: And he said, that's crazy. I've been working in New
Speaker 1: York for thirty years. I've never seen any smart young
Speaker 1: kids want to go start companies. There's something happening right now.
Speaker 1: I said, that's a very nice idea. Can you leave
Speaker 1: me alone? I have to go back to work. And
Speaker 1: he said we should invest in some of these companies,
Speaker 1: and I said, okay, I'll let you know if I
Speaker 1: see any companies that are interesting. We were making little investments,
Speaker 1: and then a few months later we looked at the
Speaker 1: investments that we had made and we figured that they
Speaker 1: were actually pretty interesting. So we decided to raise a
Speaker 1: little fund. You were one of our first investors, and
Speaker 1: it was really friends and family who gave us a
Speaker 1: little bit of money, and we use that money to
Speaker 1: hire one person to sort of help professionalize and institutionalize
Speaker 1: what we were doing since we both had other jobs.
Speaker 1: It's just so happened that that vintage was BuzzFeed and
Speaker 1: Warby Parker and this awesome generation of New York startups,
Speaker 1: but in particular iconic consumer startups. And so what happened
Speaker 1: was we got our brand and our name associated with
Speaker 1: these companies that became sexy and exciting, and so right time,
Speaker 1: right place, we suddenly so I had everybody who wanted
Speaker 1: to go build the Warby Parker of whatever calling us,
Speaker 1: and eight funds later, it's worked. It's been amazing, and
Speaker 1: we built this great team and we've been able to build,
Speaker 1: you know, arguably the strongest brand in early stage New
Speaker 1: York investing, which is nuts. It's impressive. It's impressive. So
Speaker 1: contrast being an investor with being an executive. My best
Speaker 1: and worst days are being an executive. It's harder, uh,
Speaker 1: but when it works, it feels good. So that's the
Speaker 1: short version of it. I think that investing you don't
Speaker 1: feel that. So if you make a sure bet and
Speaker 1: it fails, you go. We make an amazing investment and
Speaker 1: it fails, I go, they screwed it up. Of course,
Speaker 1: I don't like to lose, and I'm so happy when
Speaker 1: these companies become big and special and The reason I
Speaker 1: said Casper earlier is because that was one where we
Speaker 1: from minute one were the lead investor, and we don't
Speaker 1: take board seats sort of as a principle because of
Speaker 1: the number of investments we had, but that's the one
Speaker 1: board seat I ever took from day one, and that's
Speaker 1: turned out to be such a fabulous company that it's
Speaker 1: been just a really cool journey to be on. Do
Speaker 1: you sleep on Casper, of course, and if you don't,
Speaker 1: that's come on. I know Neal would kill me if
Speaker 1: I could thank you. So what's your investment process? It's
Speaker 1: very collaborative. There are four partners, three managing partners for
Speaker 1: total partners, and then an investment team of five other
Speaker 1: folks who are all really smart and really different different
Speaker 1: areas of interest, areas of expertise, generations, and so we
Speaker 1: have these interesting perspectives. And then we have a three
Speaker 1: person platform team and a two person finance team, and
Speaker 1: we all have a partner meeting together and we talk
Speaker 1: about what we're looking at together. We don't do any
Speaker 1: deals that multiple partners haven't met with. It's not a
Speaker 1: consensus driven model, so anyone can lead a deal, any
Speaker 1: partner can any partner vito a deal. Any partner can
Speaker 1: veto a deal. We don't formally use table pounds and vetos.
Speaker 1: We sort of agree to disagree and then someone goes
Speaker 1: forward with an investment or not. You know, we make
Speaker 1: about twenty to twenty it's called twenty new investments a year,
Speaker 1: plus a bunch of follow ons, and so there's a
Speaker 1: lot of velocity. If we love something, we'll do it.
Speaker 1: We try not to invest in competitive companies. Were incredibly
Speaker 1: founder centric. The place where I think we really win
Speaker 1: is in having empathy because we know how hard this is.
Speaker 1: I know how terrifying it can be to build something.
Speaker 1: And so when times are good, everyone loves their investors
Speaker 1: because their investors are cheerleaders. When times are bad, that's
Speaker 1: when you really understand what kind of an investor you have.
Speaker 1: And I think that we are pretty understanding and sensitive.
Speaker 1: We don't like it when stuff goes wrong. And obviously
Speaker 1: if we think someone is being fraudulent or really irresponsible,
Speaker 1: that's not good. But if people are really trying hard
Speaker 1: and doing the best they can and things don't work out, like,
Speaker 1: that's okay, and we'll back you next time again. So
Speaker 1: you're an operator, yeah, everybody there is basically an operator.
Speaker 1: As investors, how do you bring that expertise to bear
Speaker 1: on your investment so you're not just money. It's a
Speaker 1: great question. So there's a few ways that we do it.
Speaker 1: One is real institutionalized structure. We have a support team.
Speaker 1: We're creating events for people to meet one another. We
Speaker 1: have forums where ers are asking each other, in some
Speaker 1: cases really hard questions, in other cases recommendations for a vendor.
Speaker 1: We have a full time recruiter senior recruiter on our
Speaker 1: team who parachutes into companies, and so when we invest
Speaker 1: over the next few quarters, it's very likely that we'll
Speaker 1: send a recruiter in for three months part time to
Speaker 1: help you build out your executive team, get your feet
Speaker 1: under you in the early days. We have a process
Speaker 1: for leaning in really hard around helping a company prepare
Speaker 1: for its next round of fundraising as it relates to
Speaker 1: pitch practice and building decks, and so there's this sort
Speaker 1: of more structured piece, and then there's the much less
Speaker 1: structured piece, which is how are we there when they
Speaker 1: need advice from somebody who's maybe seen this before and
Speaker 1: who's going to have an incentive to really care and
Speaker 1: so we're available seven and I never know in a
Speaker 1: day whether I'm going to talk to one of our
Speaker 1: founders or whether I'm going to talk to I mean,
Speaker 1: I might talk to none, I might talk to four.
Speaker 1: But generally speaking, the model is that companies graduate weight
Speaker 1: and so we're with a company through a seed round,
Speaker 1: they raise later stage financing. They have a Series A
Speaker 1: or Series B investor who owns and just put a
Speaker 1: bunch of money in, and there is somebody else who's
Speaker 1: the sort of primary board member. And that's what enables
Speaker 1: us to overtime build a larger and larger portfolio and
Speaker 1: still feel like we can deliver the level of service
Speaker 1: that we owe the founders. So there are people listening today.
Speaker 1: I'm sure we have an idea. They've got their thrill
Speaker 1: list in their head. What is it that grabs an
Speaker 1: investor and what is it that turns them off? I mean,
Speaker 1: it's a little bit like dating. You just feel it
Speaker 1: or you don't look. You need to be really passionate
Speaker 1: about what you do, really knowledgeable about what you do.
Speaker 1: There's a balance that we like to see around having
Speaker 1: very strong conviction for what you want to build, but
Speaker 1: not so much conviction that you seem unwilling to examine
Speaker 1: other ideas or viewpoints. We sort of believe that every
Speaker 1: one of these companies has to pivot. It's some point
Speaker 1: in some way, shape or form, and so you want
Speaker 1: to see that sort of flexibility or malleability, but not
Speaker 1: so much that they come in and they say we
Speaker 1: want to build this thing and it's black, and I
Speaker 1: go what about white? They go yeah, yeah, wait, So
Speaker 1: that's the that's the balance. It's just somebody who has
Speaker 1: a head on their shoulders and a belief in what
Speaker 1: they want to build and can articulate why they want
Speaker 1: to build and why it's a good opportunity, and you
Speaker 1: believe that they're going to walk through walls to get
Speaker 1: it done. But I will say being more prepared and
Speaker 1: having better materials and having a vision for what the
Speaker 1: business is gonna look like. And you know, if you
Speaker 1: want to raise one and a half million dollars, I'd
Speaker 1: like to understand why that's the right amount of money
Speaker 1: and how long it's gonna get you and what the
Speaker 1: different outcomes might be from that. But I'll forgive some
Speaker 1: lack of technical knowledge or business savvy if it's somebody
Speaker 1: who I think has such a keen understanding of the
Speaker 1: consumer that they're going after the market that they're entering,
Speaker 1: so there's no formula. What's more important as an investor,
Speaker 1: the person or the idea. I think that the person
Speaker 1: is more important. Right now, we're investing in people we
Speaker 1: love with an idea we like. Okay, And we talked
Speaker 1: about this for a long time in the partner meeting
Speaker 1: because we said, oh God, they're so compelling, they're so smart,
Speaker 1: they're what a great team. This market's not awesome. Yeah,
Speaker 1: but they're gonna pivot and we love them and we
Speaker 1: don't want to miss being in business with them. And
Speaker 1: even if this isn't the one that gets there, the
Speaker 1: next one will be. And if we take a slightly
Speaker 1: longer term approach, these are people when we want to
Speaker 1: be in business with. You would never say that about
Speaker 1: an idea and go, uh, this idea is gonna be awesome,
Speaker 1: even though we think these people are terrible in fraudsters.
Speaker 1: This podcast is about math and magic. Let's talk specifically
Speaker 1: about the math. How much were you looking at data
Speaker 1: in the early thrillerst years, as much as anybody else
Speaker 1: doing what we were doing at that point. What kind
Speaker 1: of information did you look at to inform you besides
Speaker 1: your friends say wow, Ben, you're doing a great job.
Speaker 1: I mean, there was a lot of anecdotal information about
Speaker 1: the impact that we had on the business says that
Speaker 1: we covered. That was really important because there was something
Speaker 1: in that that measured trust. You know, we did a
Speaker 1: lot of studying click through rates, share rates, and unsubscribed rates.
Speaker 1: We did, I think, as good a job as we
Speaker 1: could have with the resources that we had to sort
Speaker 1: of study our subscription funnel and to look at the
Speaker 1: efficacy of some of the partnerships that we built. But
Speaker 1: in reality, it was just a much less data rich
Speaker 1: world back then, and so Thrillist was built with enough
Speaker 1: data that we weren't blind, but a lot more of
Speaker 1: the magic than the math. Today, you're running a lot
Speaker 1: of businesses, they're all in this data world. What data
Speaker 1: do you look at? And what's so important to building
Speaker 1: these businesses? Now you know there's enough data you can
Speaker 1: you can hang yourself with it, right, And so now
Speaker 1: the question isn't are we using data? The question sometimes
Speaker 1: is are we using too much data? And what do
Speaker 1: you think? Well? I think that the answer is often
Speaker 1: that we are using too much data. I don't know that.
Speaker 1: I would say that in our specific business, we're using
Speaker 1: too much data. If you know something's good, you know it,
Speaker 1: and the data says it's not that good, I still like, okay,
Speaker 1: So the data has got to catch up because I
Speaker 1: know it's good. And sometimes there's something that I know
Speaker 1: isn't very good and the data would say that audiences
Speaker 1: love it, and I would go, there's no way this
Speaker 1: is just like, audiences don't love this. I get that
Speaker 1: there's a lot of views, but this is not the thing.
Speaker 1: So will you go with your gut? And I will
Speaker 1: go with my gut. That's on one side of the business.
Speaker 1: I think in the advertising business right now, data is
Speaker 1: a terrifying, terrifying thing. Why Well, just because everything in
Speaker 1: digital is just right to the lowest common denominator. Almost
Speaker 1: all money being spent digitally is being spent blindly. Do
Speaker 1: you think Google Search gets credit for a lot of
Speaker 1: attribution that they didn't cause? Look, I think Google is
Speaker 1: a good ad product, but we're in a last click
Speaker 1: attribution world. So whoever's got the last click totally totally, totally, totally,
Speaker 1: totally crazy. And by the way, if I'm a Marketer.
Speaker 1: It's hard to turn off the drug that some of
Speaker 1: these things create. You started out with the newsletter, somewhere
Speaker 1: along the way you added video, get it all sorts
Speaker 1: of stuff. Talk to me about audio, obviously, I've got
Speaker 1: a self interest here, But podcast, Alexa smart speaker, How
Speaker 1: does it all fit together? And what do you think
Speaker 1: that is telling us about the marketplace? Yeah? Well, I
Speaker 1: mean starting with podcast, I think it's just a super
Speaker 1: compelling medium and it's something that we're investing in and
Speaker 1: looking at doing and hopefully we're gonna do some stuff
Speaker 1: with you guys, which is really exciting. The data is
Speaker 1: overwhelmingly clear that this is a preferred format for young
Speaker 1: folks to get content, and it's a big part of
Speaker 1: their commute. And I think it works well with the
Speaker 1: kind of narrative storytelling that we do and the kind
Speaker 1: of voices and personalities that we have, and the kind
Speaker 1: of brands that we have. So I'm a big believer
Speaker 1: in that. Let's get to future of the media business.
Speaker 1: Where do you think all this goes? I think it's
Speaker 1: all Number one on Alexa mm yeah, number two. Weather.
Speaker 1: I wake up and do weather, and then my kids
Speaker 1: listen to Mo wanna We'll get them. Okay, you'll love it.
Speaker 1: That's the deal um future of the media business. I
Speaker 1: think that more consolidations coming. I think more consolidation up
Speaker 1: in the stratosphere is coming. I think more consolidation in
Speaker 1: digital is coming. I think content creators and pipe owners
Speaker 1: continue to join forces. I think if you're a consumer,
Speaker 1: it's awesome. There's gonna be a lot of great content
Speaker 1: for a long time. And you have companies that don't
Speaker 1: even care about the media business who are going to
Speaker 1: spend billions and billions of dollars underwriting content to get
Speaker 1: you to do things on their platform that have nothing
Speaker 1: to do with advertising or content at Allso great time.
Speaker 1: If you are a consumer, if you're in the media business,
Speaker 1: it's it's a chow vallenging time. There's always going to
Speaker 1: be good businesses to be built on brands that people love,
Speaker 1: and so it may not be as simple as it
Speaker 1: used to be with dual revenue stream model, but I
Speaker 1: think media companies are gonna have to be good at
Speaker 1: a lot more things simultaneously than they used to be
Speaker 1: right now, and they're gonna need to figure out ways
Speaker 1: to directly engage their audiences and sell things to them
Speaker 1: while also selling advertising, and also creating experiences, and licensing
Speaker 1: and selling I P and working with the distribution platforms.
Speaker 1: I mean, it's just a it's a confusing time, but
Speaker 1: I think it's a very hard time to be in
Speaker 1: a small independent media business in any category. This is
Speaker 1: math and magic. Who is the greatest mathematician, you know,
Speaker 1: that person who plays the math side of the equation best.
Speaker 1: There is a guy on our team who runs data
Speaker 1: and analytics and research and who's one of our executive
Speaker 1: team members. Names is Shesh Patel. And he is somebody
Speaker 1: who everybody in our company looks at as being an
Speaker 1: amazing math leader. Who's the greatest magician? Who's that creative person?
Speaker 1: You know? You still gotta go back to like Steve Jobs, right,
Speaker 1: he might be a little bit horrified at what the
Speaker 1: creation is being used for now, but that changes the
Speaker 1: world Like nothing has ever changed the world. There's still
Speaker 1: nobody that's done anything close to that as far as
Speaker 1: I'm concerned. Ben Lair, CEO of Group nine, founder of
Speaker 1: Thrill List, someone who's gone from being young turk to
Speaker 1: establishment one of the real geniuses of the business. And
Speaker 1: thanks great being here. Here's a few lessons I take
Speaker 1: away from this episode with bem use. The of the
Speaker 1: decisions are easy to green light. Of the decisions are
Speaker 1: easy to kill. But SI is the gray zone that
Speaker 1: takes up your time. Get things out of that middle.
Speaker 1: Decisions about people can be hard, but it's better to
Speaker 1: make quick decisions and not just postponed the inevitable. And finally,
Speaker 1: Ben's philosophy is that it's more important to invest in
Speaker 1: the person and the idea. A talented person or team
Speaker 1: can always pivot, and you don't want to miss an
Speaker 1: opportunity to work with the right people. Thanks for listening.
Speaker 1: I'm Bob Pittman. That's it for today's episode. Thanks so
Speaker 1: much for listening to Math and Magic, a production of
Speaker 1: I Heart Radio. The show is hosted by Bob Pittman.
Speaker 1: Special thanks to Sue Schillinger for booking and wrangling our
Speaker 1: wonderful talent, which is no small feat. Nikki Eatre for
Speaker 1: pulling research, Bill Plax and Michael Asar for their recording help,
Speaker 1: our editor Ryan Murdoch, and of course Gail Raoul, Eric Angel,
Speaker 1: Noel Mango and everyone who helped bring this show to
Speaker 1: your ears. Until next time,