June 13, 2019 • 38 mins
Ben Lerer knows brands. As the co-founder of Thrillist, Ben created the go-to recommendation engine for everything from secret menu items to must-have flip flops (they came with bottle openers built into them!) In the 15 years since, Ben's not only grown the business, but become CEO of Group Nine Media--parent company to some of the most popular digital brands including NowThis and the Dodo. And somehow he's also found time to launch a successful VC fund with his dad! Learn Ben's trick for making quick business decisions, what working with his father has taught him, why founder’s empathy is what sets his fund apart, and why he always invests in the person over the idea.
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Episode Transcript
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Speaker 1 (00:01):
You're listening to Math and Magic, a production of I
Heart Radio. If you know something's good, you know it,
and the data says it's not that good. I still like, okay,
So the dad has got to catch up because I
know it's good. And sometimes there's something that I know
isn't very good and the data would say that audiences
(00:22):
love it, and I would go, there's no way. This
is just like, audiences don't love this. I get that
there's a lot of views, but this is not the thing.
So will you go with your gut? And that's what
I will go with my gut. Welcome to this episode
of Math and Magic. I'm Bob Pitman, and we're looking
(00:42):
at stories from the frontiers of marketing today. Ben layers
our guests. On first impression, you look at Ben, you
might say, wow, this is a pretty cool guy. He
must be a magician creative time for those who have
worked with him quickly find out that he actually lives
on the math side of the equation too. Regarding good business.
(01:03):
Ben as the CEO of Group nine Media, which includes
his first tech media venture and the place where he
made his mark through a list. It also includes Now
This Seeker and the Dodo, which was founded by his
super smart sister. Is he family business? Full disclosure. I've
known been or back then he was known as Benji
Dare I say that? And I've known him since he
(01:24):
was very young. His dad and I are very good
pals and have been for a long long time. His
dad's super smart, overachieving jeans must have worked somewhere there,
and we've all had some wonderful adventures together. And Pilot Group,
which was my private equity fund, backed through a list
in the early day. So I've been able to see
Ben through this whole thing and been so impressed with
so many years. So they'll leave anything out. You didn't
(01:46):
mention how handsome I am, But well, I assume we'll
get into that. No one can see this. Let's move
to you in sixties seconds. Don't think too long to
say the first thing that comes to your mind. Okay,
I can do that. Do you prefer pizza or tacos?
Pizza sweater or hoodie sweater? Unfortunately I've gotten old. You
have gotten old. I'm embarrassed. This is going poorly. iPad
(02:09):
or Kendall Kindall New York or Philly, New York Mets
are Yankees, Mets Ninja's or Pirates Ninja's sunrise or sunsets.
Sun sets. I like a sunrise, but I don't get
them as off only when you stay up all night exactly.
Secret talent, secret talent when we were in college, and
(02:34):
I can, I can, I give a longer instwer. So
when I was in college, I we did talent shows
and I did them with Bo your son, and my
secret talent was balancing a broom on my finger because
I didn't have any secret talents. That is a pathetic
thing to admit, but that's true. Place to go to
find out who you are. Back home with my family,
(02:56):
smartest person you know, not your dad, my wife for job.
First job was working for Andre Blas at his boutique
hotel company. Historical idol Alexander Hamilton came to mind. So
I guess I'll go with that favorite company you've invested in,
(03:17):
not necessarily the most profitable, favorite company, the company that
I have the closest relationship with his Casper Mattress company.
Favorite company wish you had invested in but didn't. Well,
we've passed on lots of great companies. I think probably
the one that I feel silliest about is Harry's only
because I'm friends with Jeff who would play you in
(03:37):
the movie of your Life, the guy who played Jesse
and Breaking Bad. Favorite smell pizza? No, my favorite smell
is my kid's best live concert. Obviously I heard music festival.
Who I love that? What topic can you talk about forever?
The media business or my kids again? Okay, so let's
(03:57):
get into you. Tell us about starting thrill List. I
don't get to think about this very often. It's also
appropriate that I'm doing with you. So starting thrill List
was I think the way a lot of businesses get started,
as somebody build something that they want to exist for themselves.
I was new to New York, working in a job
that was interesting, but I knew wasn't necessarily where my
(04:21):
sort of heart was in the long term, and I
became sort of enamored with the idea that there wasn't
a city guy that spoke my language. You know, my
mother and I read the same city Guide to make
a decision about where we would go and what restaurants
we would eat at, or you know, things that we
would experience. And this was at a time when there
(04:41):
was a cultural shift happening where people were moving from
really valuing what you possessed towards valuing what you did
and the experiences that you had. And I felt that
I needed better information and more trusted information, and more
personalized information about how to spend my time and money
and started writing terrible, really terrible emails to friends about
(05:05):
stuff that I discovered that I thought was fun. I
did it with a college buddy, you know, one of
my good friends from school, Adam Rich. He and I
would go out and have drinks and eat food and
do silly stuff and record it and send it out
to people, and we actually started to get a little
bit of a following, and people started doing the things
that we would recommend, And so we write about a
restaurant and the place would have a line out the
(05:26):
door the next night. We started to think it was
sort of interesting that people were taking our advice. Only
then started to do a little bit more research on
what a business model might be, and unbeknownst to us,
came across Daily Candy, which had built a very large
business doing the exact same thing for women, and unbelievably
we didn't a at first know it existed and be
(05:48):
didn't know that it was owned by you, which is
the most insane and sort of serendipitous and funny and
bizarre way to come to something. The next thing we
did was called you and said can we come over
and get your advice. We know Daily Candy has been
super successful. We've built this email list for guys that
(06:08):
is doing something similar, albeit at a pathetically small scale.
And you took interest in what we were doing, and
you know, the rest is history. You know, it's interesting
because maybe I've never told you this. Everybody kept coming
and saying, we want to do Daily Candy for men,
but they all wanted to be about fashion and things
that women are interested in. You and Adam came in
(06:30):
and what sort of I think blew us away was
You said, no, no, no, no, no, that's not what
men are interested in. That's what women are interested here's
the equivalent for men. Can you tell us a couple
of those things that you covered, Like Daily Candy, you
covered sort of one thing per day, one thing per day.
Tell us about a few of them. I mean, look,
we were not scientists. Let's call us spade to spade.
I think our first article was about a Mexican restaurant
(06:52):
that had been open for several years that we wrote
about as if it was a brand new thing, because
it was Sinco de Mayo, but it was new to us,
and I guess it was new to enough people that
people took interest in it. When we started to really
get our feet under us is when restaurants or new
places that opened started to understand that we were we
were able to move audiences, and so we went from
(07:14):
having to sort of curate what existed into getting access
to things before other people knew about them. And so
at that point, where was a daily email was something
where if you were really curious and you really wanted
to be on the cutting edge of what was happening,
we sort of became a must read because we were
providing breaking information. It wasn't breaking political news. It was
(07:37):
a taco stand was opening, But if you were really
passionate about living that kind of life, we were able
to bring you that information first. And then we were
maniacal about creating a brand and a persona that was
different than the way that other people covered the category.
And if we wrote about a restaurant the same week
that New York Magazine and New York Times and zag
(07:58):
It and Daily Can and a bunch of other reputable
places did, and if you picked up the thrill List
review or the thrillst recommendation, you would immediately know that
it was thrill List. After a while, we were able
to package it up and build it in a repeatable,
scalable way that enabled us to not have to edit
(08:19):
every single piece of content ourself for myself, but create
something that could be the voice of a brand, which
you know, as you know, any great brand is all
about what is that voice, what's that mission, why does
it exist? And how can you make it something that
even at scale, can be replicated. I think I remember
it was either the Pitch or it was one of
the first news letters you found flip flops that had
(08:40):
a beer opener. It was called the Fanning. But every
time I would read thrill List, I chuckled out loud.
Our lawyer at our investment group came in one day
and do you know what those guys are doing? They
had a party last night and it was a hatchet
throwing party. Do you remember that? Yes? I do remember this.
That was sort of set that. I don't know that
(09:02):
our lawyers would allow us to do that. At this point.
We had a lot of fun. It was it was
a different time. I mean, right, we like the world
was a little bit looser. Who are you throwing hatchets
at random party goers who signed nothing? They were on
a wheel spinning and someone was just flinging hatchets against
the wood behind them. Yeah, it was probably not a
great idea, and first time investors ever called and said,
(09:24):
you know, maybe this is not a good idea. So
you were what major political science? Political science? Okay, political science.
Guy had no real training in business. Yet you turned
out very quickly to be this very astute CEO. And
one of the things I observed was you made quick decisions.
You would say we're gonna do this, and it's gonna
happen here, and then two months later you go, they
(09:45):
didn't deliver. I fired them. I'm trying again. You never
hung on to these old ideas or what you hope for.
You were very decisive. You help people to real clear standards.
Where do you think you learned that from? Well, I
don't know if that was a set up or not,
but I quoted you as recently as this week on
the twenty rule, which is an old thing that you
(10:10):
used to talk about that I talk about all the time,
which is this idea that twenty percent of the time
the things that you do or the decisions that you
make in business are obviously right. Immediately you hire someone
who's a superstar, you launch your product that's a hit,
and you know you have something good. And twenty of
the time you do something that is very easy to kill.
It's just not working and there's not a lot of
(10:30):
emotional baggage with it. It's easy to sort of get
out of the way. And sixty percent of the things
that you do are somewhere in between, and you can
rationalize why you're gonna keep doing them, and you can
also rationalize why they're not big hits. And the advice
that you gave early was get stuff out of that
six and into one of the twenties as fast as
you can, because the sixtent is what kills you. That's
(10:52):
the stuff that it doesn't really deliver profit or it's
vanity metrics, but it's not anything that really drives the
substance of what's gonna power your business forward. And that's
a philosophy that I have very much taken to heart.
That's something that is an operating philosophy that we now
have at Group nine around how we make decisions, which
is mediocre stuff can't have a place here. That's something
(11:15):
that you taught me, frankly, and something that I try
to institutionalize in our business and sometimes succeeding, sometimes failed.
I no idea. I thought you that I've always given
you credits and wow, look at him here, but you
know that, I mean, do you still talk about of
course I do weed the garden. It's not a clear winner.
It's a loser by definition. Instead of defining stuff that's
not a clear loser as a winner, that's in a
more concise way of doing it. Next time, I'll say that,
(11:37):
how do you balance quick decision versus giving people, executives
or whoever in your organization the time to make some
mistakes and grow. There's not a rule that's a fuel
one for me, which is if you don't actually think
the person is going to get there, but it would
just be really convenient if they did, you're probably better
(11:58):
off ripping that band aid. You just have to sort
of really be willing to give yourself a good look
in the mirror. And by the way, I'm sometimes I'm
very good at this, and sometimes I'm very bad at this.
But how introspective can you be and can you really
acknowledge when you're just delaying the inevitable? Others came to
knock you off. You've got success very early with Thrillist.
This was like wow product and up King Urban Daddy
(12:21):
and a couple of others. How did you react to it?
How did you defend your turf? It's a It's a
good question. I think that we first and foremost the
way that you defend is you just deliver a better product.
For a long time, I think we delivered a definitively
better product. I think there are actually moments where we
(12:43):
you know, you hit a rough spot or a company
gets a little bit of momentum, and there were times
where I didn't know that we necessarily had a better product.
But I think that we had the support of our
investor base helping us whether more difficult times, which I
am still a huge believer in. And I also think
at the end of the day, a lot of this
is just will power. None of this is rocket science.
(13:06):
In particular the media business. If you're smart enough and
you're able to get a group of smart enough people
to sort of believe in something and work together you
can will your way to success. We didn't have any
tricks up our sleeve. This was just refusing to quit
for a long time. You've always been open to a
lot of ideas. I think initially looking at you, I thought,
(13:26):
maybe that's good. You're young. But now let's see you
at your age and you're still young, but not as young,
and you're still open to new ideas. In that early period,
what was one idea that you say that definitely worked,
and what idea was one to say that definitely failed
and why do you think that happened. One of the
definite things that worked was a strategy around how we
were going to go and expand market to market. It
(13:47):
wasn't a novel idea. It was something that Daily Candy
had done, but we were able to stamp out and
repeat a process of how we would launch a market,
how we would partner to accumulate subscribers pretty quickly, how
we would leverage our existing advertiser base to support a
new market that we launched. And so I think that
we built a little bit of a machine to go
(14:08):
and and expand geographically. That worked early on when did
you realize through a list that arrived. I think I
realized Thrillis had arrived when we got bigger than Daily
Candy had ever been. That was certainly a moment, an
unbelievable moment for us, when this thing that we had
always aspired to be, we weren't able to use their
(14:29):
blueprint anymore to grow because we had done what they
had done. That was probably the moment. At the same time,
I really have to admit I have moments where I
think we've arrived, and then the goal posts move so
quickly that it's very rare that I get a minute,
even a second to really feel like we've arrived. But
(14:52):
that moment when we passed Daily Candy, I think was
one special one. I think when we created Group nine
and merged brands together was another one. And now the
best moments I get for sort of celebrating that arrival
or success is when we when we have town halls
actually so nothing external, but when we get time with
the whole company and get to sort of take inventory
(15:14):
on what we're doing and see everybody in one space.
We do it every six months. We did it yesterday,
which is why it stopped of mind. But those are
really exciting and you know, slightly emotional to feel the
momentum in the progress and where we're at. Those are
now the moments, but they're fleeting. So advertisers, how did
you so advertisers? Started out as the CEO running the company,
(15:38):
but you also start out as the face to the
advertising community. You were your time talking advertisers. Yeah, early
on at least, how did you break advertising? Because you
talk to people's starting businesses to get a little bit
of consumer attraction and they can't seem to make money.
You did and sort of surprisingly well early on? What
did you do that you think is unique or responsible
(15:59):
for them? And I think there are moments in time
where things are easier or harder. I think when we launched,
the Tide was a little different, and Daily Candy was
this rising, exciting proposition. They had popularized email marketing for
our consumer audience. They had pioneered the dedicated email and
(16:20):
some formats that were really effective and that the advertising
community leaned into. And so we got to ride those
coattails very directly. I mean, the way that we prospected
was we looked at people who were spending money with
Daily Candy, and we went to them and said, we're
doing that but for guys. And that was how we
got a lot of our early business. And today you
(16:44):
still spend that much time with advertisers. I spend a
lot of time thinking about our advertising business. I spend
less time out in market in specific meetings. I do
it in chunk. So I'll do it, you know, when
we're out and can or C s or. But my
team is incredible and so thoughtful and so creative. You know,
(17:05):
I can still add my value here and there through
a list has gone from frat boy humor would throw
hatchets at people at our parties. Two. I hate to
use this word sophisticated. Well let's not. I would also
hate for you to use that word. Okay, let's think
of something else other than sophisticated. But it's certainly evolved. Yes,
How do you evolve the brand like that without leaving
(17:27):
your consumers behind or replacing one audience for another. It's
something that we struggle with and talk about a lot,
particularly these days. It's something that's just front of mind.
The brand grew up for a while with us, just
because we didn't know how to stop it from growing
up with us. At a certain point, the company got
bigger and we went into other businesses and I let
(17:49):
it go. It was no longer you know, a reflection,
a reflection of me, thank you. That was what I
was looking for. The things that we realized over time
were the lifestyle that we were promoting and celebrating was
again it was about experiences and about every day being
better than the last, and doing the stuff that you love.
(18:09):
That's not for guys, that's just for people. That's a
much broader audience. And so when we realized that our
mission was one where we didn't have to contort it
in order to make it applicable to a broader audience,
we gave ourselves permission to let it be for a
broader audience, and that has served us well. Just hold
(18:30):
on a second, because we've got so much more to
talk about. We'll be back after a quick break. Welcome
back to Math and Magic. We're here with Ben Lair.
You have a bigger than life dad, Ken Larry. He's
a chairman of BuzzFeed, Blade, and god knows what else.
He has always been on the cutting edge. He Foundedfington
(18:52):
Post with Arianna Huffington. He was in the c suite
at a O L and it's Heyday at time one
or two before that, he had a huge communications company,
and indeed he was working with Microsoft and Bill Gates
when they sort of became icons. Right before I go, well,
what did you learn from your dad? He's really good
at just cutting to the core of an issue and
(19:13):
doing away with a lot of the waste and getting
to what's important. And so that's something that I try
to do as well. So that's the thing in business,
But you know, the business advice is secondary. The thing
that I've taken from him is how to prioritize business
visa v. Your family, Because I'm a much better business
(19:34):
person when business comes second. If I'm settled with my
family and I put my kids to bed every night
and like in that rhythm and and always putting family first,
then it allows me to put business in a much
healthier place and make much more rational decisions. So your
dad was, I know, a great role model for you there.
The family always came first to him. Um and when
(19:57):
your mother was away, uh, he would sneak you off
to mc anmods to have the forbidden foods. True. Talking
about your family, how do you think about work family balance?
And what do you recommend to the people you work
with and the people who you give advice to. I
don't have a specific like here's how you should spend
your time, but I would just say that family needs
(20:21):
to come first. For me, what that means is I
put my kids to bed. I'm with them every morning,
and then I put my kids to bed four out
of five week nights, and then by the way, I
go back out. So tonight I will go home, I'll
be home before seven o'clock. I'll put my kids in bed,
I'll have half an hour with them, and then I
have worked dinner. But that for me is like a
(20:43):
really important thing that grounds me. And also and with
my kids at seven in the morning, I don't want
to say I'll see tomorrow. That's how I've built my
calendar and how I've structured my work life. And I
have two jobs investing in running Group nine. You know,
my days are booked to the second and I book
my family into that day. It's really easy to just
(21:06):
let the calendar fill up and not make that a priority.
But that's something that I won't I won't do. Do
you put your phone away when you're with family? Yeah?
I try to, and there are days when I forget
to do your kids remind you? My kids don't remind
me to put my phone away, except my kids want
to pull it out of my hand and play with it,
which is very depressing. We live in a confusing world
(21:28):
right now. The addiction of technology is is horrifying, and
so I really have to set boundaries for myself. I
don't sleep with my phone in my room anymore. Do
you have an alarm on your phone? No, I have
an alarm clock. I'm like, what from blood eyed? I
hope it's a clock radio. It's a clock radio, except
I don't know how to set it, so it just
goes set it to Elvis Duran in the morning, or
(21:49):
the Breakfast Club or one of our other great shows
here in New York. And so about ten years ago,
INC Magazine picked you as one of their thirty under thirty.
But it was also about the time you started Layer
of Ventures with your dad. Tell me about starting that
and how you weave that into your jay job. Running
thrill list. New York was at an interesting point ten
years ago where New York wasn't a TechTown yet and
(22:12):
I was starting thrill lists and my dad had started
huf PO as you mentioned, and my dad actually just
had a super interesting insight, which was your friends or
my friends were leaving good schools and instead of wanting
to go and work on Wall Street or work in consulting,
they wanted to go work at startups or start companies.
(22:33):
And he said, that's crazy. I've been working in New
York for thirty years. I've never seen any smart young
kids want to go start companies. There's something happening right now.
I said, that's a very nice idea. Can you leave
me alone? I have to go back to work. And
he said we should invest in some of these companies,
and I said, okay, I'll let you know if I
see any companies that are interesting. We were making little investments,
(22:54):
and then a few months later we looked at the
investments that we had made and we figured that they
were actually pretty interesting. So we decided to raise a
little fund. You were one of our first investors, and
it was really friends and family who gave us a
little bit of money, and we use that money to
hire one person to sort of help professionalize and institutionalize
what we were doing since we both had other jobs.
(23:15):
It's just so happened that that vintage was BuzzFeed and
Warby Parker and this awesome generation of New York startups,
but in particular iconic consumer startups. And so what happened
was we got our brand and our name associated with
these companies that became sexy and exciting, and so right time,
(23:38):
right place, we suddenly so I had everybody who wanted
to go build the Warby Parker of whatever calling us,
and eight funds later, it's worked. It's been amazing, and
we built this great team and we've been able to build,
you know, arguably the strongest brand in early stage New
York investing, which is nuts. It's impressive. It's impressive. So
(24:00):
contrast being an investor with being an executive. My best
and worst days are being an executive. It's harder, uh,
but when it works, it feels good. So that's the
short version of it. I think that investing you don't
feel that. So if you make a sure bet and
it fails, you go. We make an amazing investment and
(24:23):
it fails, I go, they screwed it up. Of course,
I don't like to lose, and I'm so happy when
these companies become big and special and The reason I
said Casper earlier is because that was one where we
from minute one were the lead investor, and we don't
take board seats sort of as a principle because of
the number of investments we had, but that's the one
(24:44):
board seat I ever took from day one, and that's
turned out to be such a fabulous company that it's
been just a really cool journey to be on. Do
you sleep on Casper, of course, and if you don't,
that's come on. I know Neal would kill me if
I could thank you. So what's your investment process? It's
very collaborative. There are four partners, three managing partners for
(25:05):
total partners, and then an investment team of five other
folks who are all really smart and really different different
areas of interest, areas of expertise, generations, and so we
have these interesting perspectives. And then we have a three
person platform team and a two person finance team, and
we all have a partner meeting together and we talk
(25:27):
about what we're looking at together. We don't do any
deals that multiple partners haven't met with. It's not a
consensus driven model, so anyone can lead a deal, any
partner can any partner vito a deal. Any partner can
veto a deal. We don't formally use table pounds and vetos.
We sort of agree to disagree and then someone goes
(25:47):
forward with an investment or not. You know, we make
about twenty to twenty it's called twenty new investments a year,
plus a bunch of follow ons, and so there's a
lot of velocity. If we love something, we'll do it.
We try not to invest in competitive companies. Were incredibly
founder centric. The place where I think we really win
is in having empathy because we know how hard this is.
(26:09):
I know how terrifying it can be to build something.
And so when times are good, everyone loves their investors
because their investors are cheerleaders. When times are bad, that's
when you really understand what kind of an investor you have.
And I think that we are pretty understanding and sensitive.
We don't like it when stuff goes wrong. And obviously
if we think someone is being fraudulent or really irresponsible,
(26:30):
that's not good. But if people are really trying hard
and doing the best they can and things don't work out, like,
that's okay, and we'll back you next time again. So
you're an operator, yeah, everybody there is basically an operator.
As investors, how do you bring that expertise to bear
on your investment so you're not just money. It's a
great question. So there's a few ways that we do it.
One is real institutionalized structure. We have a support team.
(26:55):
We're creating events for people to meet one another. We
have forums where ers are asking each other, in some
cases really hard questions, in other cases recommendations for a vendor.
We have a full time recruiter senior recruiter on our
team who parachutes into companies, and so when we invest
over the next few quarters, it's very likely that we'll
(27:17):
send a recruiter in for three months part time to
help you build out your executive team, get your feet
under you in the early days. We have a process
for leaning in really hard around helping a company prepare
for its next round of fundraising as it relates to
pitch practice and building decks, and so there's this sort
of more structured piece, and then there's the much less
structured piece, which is how are we there when they
(27:40):
need advice from somebody who's maybe seen this before and
who's going to have an incentive to really care and
so we're available seven and I never know in a
day whether I'm going to talk to one of our
founders or whether I'm going to talk to I mean,
I might talk to none, I might talk to four.
But generally speaking, the model is that companies graduate weight
and so we're with a company through a seed round,
(28:02):
they raise later stage financing. They have a Series A
or Series B investor who owns and just put a
bunch of money in, and there is somebody else who's
the sort of primary board member. And that's what enables
us to overtime build a larger and larger portfolio and
still feel like we can deliver the level of service
that we owe the founders. So there are people listening today.
I'm sure we have an idea. They've got their thrill
(28:24):
list in their head. What is it that grabs an
investor and what is it that turns them off? I mean,
it's a little bit like dating. You just feel it
or you don't look. You need to be really passionate
about what you do, really knowledgeable about what you do.
There's a balance that we like to see around having
very strong conviction for what you want to build, but
(28:47):
not so much conviction that you seem unwilling to examine
other ideas or viewpoints. We sort of believe that every
one of these companies has to pivot. It's some point
in some way, shape or form, and so you want
to see that sort of flexibility or malleability, but not
so much that they come in and they say we
(29:08):
want to build this thing and it's black, and I
go what about white? They go yeah, yeah, wait, So
that's the that's the balance. It's just somebody who has
a head on their shoulders and a belief in what
they want to build and can articulate why they want
to build and why it's a good opportunity, and you
believe that they're going to walk through walls to get
it done. But I will say being more prepared and
having better materials and having a vision for what the
(29:31):
business is gonna look like. And you know, if you
want to raise one and a half million dollars, I'd
like to understand why that's the right amount of money
and how long it's gonna get you and what the
different outcomes might be from that. But I'll forgive some
lack of technical knowledge or business savvy if it's somebody
who I think has such a keen understanding of the
consumer that they're going after the market that they're entering,
(29:53):
so there's no formula. What's more important as an investor,
the person or the idea. I think that the person
is more important. Right now, we're investing in people we
love with an idea we like. Okay, And we talked
about this for a long time in the partner meeting
because we said, oh God, they're so compelling, they're so smart,
they're what a great team. This market's not awesome. Yeah,
(30:16):
but they're gonna pivot and we love them and we
don't want to miss being in business with them. And
even if this isn't the one that gets there, the
next one will be. And if we take a slightly
longer term approach, these are people when we want to
be in business with. You would never say that about
an idea and go, uh, this idea is gonna be awesome,
even though we think these people are terrible in fraudsters.
(30:37):
This podcast is about math and magic. Let's talk specifically
about the math. How much were you looking at data
in the early thrillerst years, as much as anybody else
doing what we were doing at that point. What kind
of information did you look at to inform you besides
your friends say wow, Ben, you're doing a great job.
I mean, there was a lot of anecdotal information about
(30:58):
the impact that we had on the business says that
we covered. That was really important because there was something
in that that measured trust. You know, we did a
lot of studying click through rates, share rates, and unsubscribed rates.
We did, I think, as good a job as we
could have with the resources that we had to sort
(31:18):
of study our subscription funnel and to look at the
efficacy of some of the partnerships that we built. But
in reality, it was just a much less data rich
world back then, and so Thrillist was built with enough
data that we weren't blind, but a lot more of
the magic than the math. Today, you're running a lot
(31:39):
of businesses, they're all in this data world. What data
do you look at? And what's so important to building
these businesses? Now you know there's enough data you can
you can hang yourself with it, right, And so now
the question isn't are we using data? The question sometimes
is are we using too much data? And what do
you think? Well? I think that the answer is often
(32:00):
that we are using too much data. I don't know that.
I would say that in our specific business, we're using
too much data. If you know something's good, you know it,
and the data says it's not that good, I still like, okay,
So the data has got to catch up because I
know it's good. And sometimes there's something that I know
isn't very good and the data would say that audiences
(32:20):
love it, and I would go, there's no way this
is just like, audiences don't love this. I get that
there's a lot of views, but this is not the thing.
So will you go with your gut? And I will
go with my gut. That's on one side of the business.
I think in the advertising business right now, data is
a terrifying, terrifying thing. Why Well, just because everything in
digital is just right to the lowest common denominator. Almost
(32:44):
all money being spent digitally is being spent blindly. Do
you think Google Search gets credit for a lot of
attribution that they didn't cause? Look, I think Google is
a good ad product, but we're in a last click
attribution world. So whoever's got the last click totally totally, totally, totally,
(33:07):
totally crazy. And by the way, if I'm a Marketer.
It's hard to turn off the drug that some of
these things create. You started out with the newsletter, somewhere
along the way you added video, get it all sorts
of stuff. Talk to me about audio, obviously, I've got
a self interest here, But podcast, Alexa smart speaker, How
(33:29):
does it all fit together? And what do you think
that is telling us about the marketplace? Yeah? Well, I
mean starting with podcast, I think it's just a super
compelling medium and it's something that we're investing in and
looking at doing and hopefully we're gonna do some stuff
with you guys, which is really exciting. The data is
overwhelmingly clear that this is a preferred format for young
(33:50):
folks to get content, and it's a big part of
their commute. And I think it works well with the
kind of narrative storytelling that we do and the kind
of voices and personalities that we have, and the kind
of brands that we have. So I'm a big believer
in that. Let's get to future of the media business.
Where do you think all this goes? I think it's
all Number one on Alexa mm yeah, number two. Weather.
(34:14):
I wake up and do weather, and then my kids
listen to Mo wanna We'll get them. Okay, you'll love it.
That's the deal um future of the media business. I
think that more consolidations coming. I think more consolidation up
in the stratosphere is coming. I think more consolidation in
digital is coming. I think content creators and pipe owners
(34:36):
continue to join forces. I think if you're a consumer,
it's awesome. There's gonna be a lot of great content
for a long time. And you have companies that don't
even care about the media business who are going to
spend billions and billions of dollars underwriting content to get
you to do things on their platform that have nothing
to do with advertising or content at Allso great time.
If you are a consumer, if you're in the media business,
(34:59):
it's it's a chow vallenging time. There's always going to
be good businesses to be built on brands that people love,
and so it may not be as simple as it
used to be with dual revenue stream model, but I
think media companies are gonna have to be good at
a lot more things simultaneously than they used to be
right now, and they're gonna need to figure out ways
to directly engage their audiences and sell things to them
(35:23):
while also selling advertising, and also creating experiences, and licensing
and selling I P and working with the distribution platforms.
I mean, it's just a it's a confusing time, but
I think it's a very hard time to be in
a small independent media business in any category. This is
math and magic. Who is the greatest mathematician, you know,
(35:46):
that person who plays the math side of the equation best.
There is a guy on our team who runs data
and analytics and research and who's one of our executive
team members. Names is Shesh Patel. And he is somebody
who everybody in our company looks at as being an
amazing math leader. Who's the greatest magician? Who's that creative person?
(36:11):
You know? You still gotta go back to like Steve Jobs, right,
he might be a little bit horrified at what the
creation is being used for now, but that changes the
world Like nothing has ever changed the world. There's still
nobody that's done anything close to that as far as
I'm concerned. Ben Lair, CEO of Group nine, founder of
Thrill List, someone who's gone from being young turk to
(36:34):
establishment one of the real geniuses of the business. And
thanks great being here. Here's a few lessons I take
away from this episode with bem use. The of the
decisions are easy to green light. Of the decisions are
easy to kill. But SI is the gray zone that
(36:54):
takes up your time. Get things out of that middle.
Decisions about people can be hard, but it's better to
make quick decisions and not just postponed the inevitable. And finally,
Ben's philosophy is that it's more important to invest in
the person and the idea. A talented person or team
can always pivot, and you don't want to miss an
opportunity to work with the right people. Thanks for listening.
(37:18):
I'm Bob Pittman. That's it for today's episode. Thanks so
much for listening to Math and Magic, a production of
I Heart Radio. The show is hosted by Bob Pittman.
Special thanks to Sue Schillinger for booking and wrangling our
wonderful talent, which is no small feat. Nikki Eatre for
(37:41):
pulling research, Bill Plax and Michael Asar for their recording help,
our editor Ryan Murdoch, and of course Gail Raoul, Eric Angel,
Noel Mango and everyone who helped bring this show to
your ears. Until next time,
You're listening to Math and Magic, a production of I
Heart Radio. If you know something's good, you know it,
and the data says it's not that good. I still like, okay,
So the dad has got to catch up because I
know it's good. And sometimes there's something that I know
isn't very good and the data would say that audiences
(00:22):
love it, and I would go, there's no way. This
is just like, audiences don't love this. I get that
there's a lot of views, but this is not the thing.
So will you go with your gut? And that's what
I will go with my gut. Welcome to this episode
of Math and Magic. I'm Bob Pitman, and we're looking
(00:42):
at stories from the frontiers of marketing today. Ben layers
our guests. On first impression, you look at Ben, you
might say, wow, this is a pretty cool guy. He
must be a magician creative time for those who have
worked with him quickly find out that he actually lives
on the math side of the equation too. Regarding good business.
(01:03):
Ben as the CEO of Group nine Media, which includes
his first tech media venture and the place where he
made his mark through a list. It also includes Now
This Seeker and the Dodo, which was founded by his
super smart sister. Is he family business? Full disclosure. I've
known been or back then he was known as Benji
Dare I say that? And I've known him since he
(01:24):
was very young. His dad and I are very good
pals and have been for a long long time. His
dad's super smart, overachieving jeans must have worked somewhere there,
and we've all had some wonderful adventures together. And Pilot Group,
which was my private equity fund, backed through a list
in the early day. So I've been able to see
Ben through this whole thing and been so impressed with
so many years. So they'll leave anything out. You didn't
(01:46):
mention how handsome I am, But well, I assume we'll
get into that. No one can see this. Let's move
to you in sixties seconds. Don't think too long to
say the first thing that comes to your mind. Okay,
I can do that. Do you prefer pizza or tacos?
Pizza sweater or hoodie sweater? Unfortunately I've gotten old. You
have gotten old. I'm embarrassed. This is going poorly. iPad
(02:09):
or Kendall Kindall New York or Philly, New York Mets
are Yankees, Mets Ninja's or Pirates Ninja's sunrise or sunsets.
Sun sets. I like a sunrise, but I don't get
them as off only when you stay up all night exactly.
Secret talent, secret talent when we were in college, and
(02:34):
I can, I can, I give a longer instwer. So
when I was in college, I we did talent shows
and I did them with Bo your son, and my
secret talent was balancing a broom on my finger because
I didn't have any secret talents. That is a pathetic
thing to admit, but that's true. Place to go to
find out who you are. Back home with my family,
(02:56):
smartest person you know, not your dad, my wife for job.
First job was working for Andre Blas at his boutique
hotel company. Historical idol Alexander Hamilton came to mind. So
I guess I'll go with that favorite company you've invested in,
(03:17):
not necessarily the most profitable, favorite company, the company that
I have the closest relationship with his Casper Mattress company.
Favorite company wish you had invested in but didn't. Well,
we've passed on lots of great companies. I think probably
the one that I feel silliest about is Harry's only
because I'm friends with Jeff who would play you in
(03:37):
the movie of your Life, the guy who played Jesse
and Breaking Bad. Favorite smell pizza? No, my favorite smell
is my kid's best live concert. Obviously I heard music festival.
Who I love that? What topic can you talk about forever?
The media business or my kids again? Okay, so let's
(03:57):
get into you. Tell us about starting thrill List. I
don't get to think about this very often. It's also
appropriate that I'm doing with you. So starting thrill List
was I think the way a lot of businesses get started,
as somebody build something that they want to exist for themselves.
I was new to New York, working in a job
that was interesting, but I knew wasn't necessarily where my
(04:21):
sort of heart was in the long term, and I
became sort of enamored with the idea that there wasn't
a city guy that spoke my language. You know, my
mother and I read the same city Guide to make
a decision about where we would go and what restaurants
we would eat at, or you know, things that we
would experience. And this was at a time when there
(04:41):
was a cultural shift happening where people were moving from
really valuing what you possessed towards valuing what you did
and the experiences that you had. And I felt that
I needed better information and more trusted information, and more
personalized information about how to spend my time and money
and started writing terrible, really terrible emails to friends about
(05:05):
stuff that I discovered that I thought was fun. I
did it with a college buddy, you know, one of
my good friends from school, Adam Rich. He and I
would go out and have drinks and eat food and
do silly stuff and record it and send it out
to people, and we actually started to get a little
bit of a following, and people started doing the things
that we would recommend, And so we write about a
restaurant and the place would have a line out the
(05:26):
door the next night. We started to think it was
sort of interesting that people were taking our advice. Only
then started to do a little bit more research on
what a business model might be, and unbeknownst to us,
came across Daily Candy, which had built a very large
business doing the exact same thing for women, and unbelievably
we didn't a at first know it existed and be
(05:48):
didn't know that it was owned by you, which is
the most insane and sort of serendipitous and funny and
bizarre way to come to something. The next thing we
did was called you and said can we come over
and get your advice. We know Daily Candy has been
super successful. We've built this email list for guys that
(06:08):
is doing something similar, albeit at a pathetically small scale.
And you took interest in what we were doing, and
you know, the rest is history. You know, it's interesting
because maybe I've never told you this. Everybody kept coming
and saying, we want to do Daily Candy for men,
but they all wanted to be about fashion and things
that women are interested in. You and Adam came in
(06:30):
and what sort of I think blew us away was
You said, no, no, no, no, no, that's not what
men are interested in. That's what women are interested here's
the equivalent for men. Can you tell us a couple
of those things that you covered, Like Daily Candy, you
covered sort of one thing per day, one thing per day.
Tell us about a few of them. I mean, look,
we were not scientists. Let's call us spade to spade.
I think our first article was about a Mexican restaurant
(06:52):
that had been open for several years that we wrote
about as if it was a brand new thing, because
it was Sinco de Mayo, but it was new to us,
and I guess it was new to enough people that
people took interest in it. When we started to really
get our feet under us is when restaurants or new
places that opened started to understand that we were we
were able to move audiences, and so we went from
(07:14):
having to sort of curate what existed into getting access
to things before other people knew about them. And so
at that point, where was a daily email was something
where if you were really curious and you really wanted
to be on the cutting edge of what was happening,
we sort of became a must read because we were
providing breaking information. It wasn't breaking political news. It was
(07:37):
a taco stand was opening, But if you were really
passionate about living that kind of life, we were able
to bring you that information first. And then we were
maniacal about creating a brand and a persona that was
different than the way that other people covered the category.
And if we wrote about a restaurant the same week
that New York Magazine and New York Times and zag
(07:58):
It and Daily Can and a bunch of other reputable
places did, and if you picked up the thrill List
review or the thrillst recommendation, you would immediately know that
it was thrill List. After a while, we were able
to package it up and build it in a repeatable,
scalable way that enabled us to not have to edit
(08:19):
every single piece of content ourself for myself, but create
something that could be the voice of a brand, which
you know, as you know, any great brand is all
about what is that voice, what's that mission, why does
it exist? And how can you make it something that
even at scale, can be replicated. I think I remember
it was either the Pitch or it was one of
the first news letters you found flip flops that had
(08:40):
a beer opener. It was called the Fanning. But every
time I would read thrill List, I chuckled out loud.
Our lawyer at our investment group came in one day
and do you know what those guys are doing? They
had a party last night and it was a hatchet
throwing party. Do you remember that? Yes? I do remember this.
That was sort of set that. I don't know that
(09:02):
our lawyers would allow us to do that. At this point.
We had a lot of fun. It was it was
a different time. I mean, right, we like the world
was a little bit looser. Who are you throwing hatchets
at random party goers who signed nothing? They were on
a wheel spinning and someone was just flinging hatchets against
the wood behind them. Yeah, it was probably not a
great idea, and first time investors ever called and said,
(09:24):
you know, maybe this is not a good idea. So
you were what major political science? Political science? Okay, political science.
Guy had no real training in business. Yet you turned
out very quickly to be this very astute CEO. And
one of the things I observed was you made quick decisions.
You would say we're gonna do this, and it's gonna
happen here, and then two months later you go, they
(09:45):
didn't deliver. I fired them. I'm trying again. You never
hung on to these old ideas or what you hope for.
You were very decisive. You help people to real clear standards.
Where do you think you learned that from? Well, I
don't know if that was a set up or not,
but I quoted you as recently as this week on
the twenty rule, which is an old thing that you
(10:10):
used to talk about that I talk about all the time,
which is this idea that twenty percent of the time
the things that you do or the decisions that you
make in business are obviously right. Immediately you hire someone
who's a superstar, you launch your product that's a hit,
and you know you have something good. And twenty of
the time you do something that is very easy to kill.
It's just not working and there's not a lot of
(10:30):
emotional baggage with it. It's easy to sort of get
out of the way. And sixty percent of the things
that you do are somewhere in between, and you can
rationalize why you're gonna keep doing them, and you can
also rationalize why they're not big hits. And the advice
that you gave early was get stuff out of that
six and into one of the twenties as fast as
you can, because the sixtent is what kills you. That's
(10:52):
the stuff that it doesn't really deliver profit or it's
vanity metrics, but it's not anything that really drives the
substance of what's gonna power your business forward. And that's
a philosophy that I have very much taken to heart.
That's something that is an operating philosophy that we now
have at Group nine around how we make decisions, which
is mediocre stuff can't have a place here. That's something
(11:15):
that you taught me, frankly, and something that I try
to institutionalize in our business and sometimes succeeding, sometimes failed.
I no idea. I thought you that I've always given
you credits and wow, look at him here, but you
know that, I mean, do you still talk about of
course I do weed the garden. It's not a clear winner.
It's a loser by definition. Instead of defining stuff that's
not a clear loser as a winner, that's in a
more concise way of doing it. Next time, I'll say that,
(11:37):
how do you balance quick decision versus giving people, executives
or whoever in your organization the time to make some
mistakes and grow. There's not a rule that's a fuel
one for me, which is if you don't actually think
the person is going to get there, but it would
just be really convenient if they did, you're probably better
(11:58):
off ripping that band aid. You just have to sort
of really be willing to give yourself a good look
in the mirror. And by the way, I'm sometimes I'm
very good at this, and sometimes I'm very bad at this.
But how introspective can you be and can you really
acknowledge when you're just delaying the inevitable? Others came to
knock you off. You've got success very early with Thrillist.
This was like wow product and up King Urban Daddy
(12:21):
and a couple of others. How did you react to it?
How did you defend your turf? It's a It's a
good question. I think that we first and foremost the
way that you defend is you just deliver a better product.
For a long time, I think we delivered a definitively
better product. I think there are actually moments where we
(12:43):
you know, you hit a rough spot or a company
gets a little bit of momentum, and there were times
where I didn't know that we necessarily had a better product.
But I think that we had the support of our
investor base helping us whether more difficult times, which I
am still a huge believer in. And I also think
at the end of the day, a lot of this
is just will power. None of this is rocket science.
(13:06):
In particular the media business. If you're smart enough and
you're able to get a group of smart enough people
to sort of believe in something and work together you
can will your way to success. We didn't have any
tricks up our sleeve. This was just refusing to quit
for a long time. You've always been open to a
lot of ideas. I think initially looking at you, I thought,
(13:26):
maybe that's good. You're young. But now let's see you
at your age and you're still young, but not as young,
and you're still open to new ideas. In that early period,
what was one idea that you say that definitely worked,
and what idea was one to say that definitely failed
and why do you think that happened. One of the
definite things that worked was a strategy around how we
were going to go and expand market to market. It
(13:47):
wasn't a novel idea. It was something that Daily Candy
had done, but we were able to stamp out and
repeat a process of how we would launch a market,
how we would partner to accumulate subscribers pretty quickly, how
we would leverage our existing advertiser base to support a
new market that we launched. And so I think that
we built a little bit of a machine to go
(14:08):
and and expand geographically. That worked early on when did
you realize through a list that arrived. I think I
realized Thrillis had arrived when we got bigger than Daily
Candy had ever been. That was certainly a moment, an
unbelievable moment for us, when this thing that we had
always aspired to be, we weren't able to use their
(14:29):
blueprint anymore to grow because we had done what they
had done. That was probably the moment. At the same time,
I really have to admit I have moments where I
think we've arrived, and then the goal posts move so
quickly that it's very rare that I get a minute,
even a second to really feel like we've arrived. But
(14:52):
that moment when we passed Daily Candy, I think was
one special one. I think when we created Group nine
and merged brands together was another one. And now the
best moments I get for sort of celebrating that arrival
or success is when we when we have town halls
actually so nothing external, but when we get time with
the whole company and get to sort of take inventory
(15:14):
on what we're doing and see everybody in one space.
We do it every six months. We did it yesterday,
which is why it stopped of mind. But those are
really exciting and you know, slightly emotional to feel the
momentum in the progress and where we're at. Those are
now the moments, but they're fleeting. So advertisers, how did
you so advertisers? Started out as the CEO running the company,
(15:38):
but you also start out as the face to the
advertising community. You were your time talking advertisers. Yeah, early
on at least, how did you break advertising? Because you
talk to people's starting businesses to get a little bit
of consumer attraction and they can't seem to make money.
You did and sort of surprisingly well early on? What
did you do that you think is unique or responsible
(15:59):
for them? And I think there are moments in time
where things are easier or harder. I think when we launched,
the Tide was a little different, and Daily Candy was
this rising, exciting proposition. They had popularized email marketing for
our consumer audience. They had pioneered the dedicated email and
(16:20):
some formats that were really effective and that the advertising
community leaned into. And so we got to ride those
coattails very directly. I mean, the way that we prospected
was we looked at people who were spending money with
Daily Candy, and we went to them and said, we're
doing that but for guys. And that was how we
got a lot of our early business. And today you
(16:44):
still spend that much time with advertisers. I spend a
lot of time thinking about our advertising business. I spend
less time out in market in specific meetings. I do
it in chunk. So I'll do it, you know, when
we're out and can or C s or. But my
team is incredible and so thoughtful and so creative. You know,
(17:05):
I can still add my value here and there through
a list has gone from frat boy humor would throw
hatchets at people at our parties. Two. I hate to
use this word sophisticated. Well let's not. I would also
hate for you to use that word. Okay, let's think
of something else other than sophisticated. But it's certainly evolved. Yes,
How do you evolve the brand like that without leaving
(17:27):
your consumers behind or replacing one audience for another. It's
something that we struggle with and talk about a lot,
particularly these days. It's something that's just front of mind.
The brand grew up for a while with us, just
because we didn't know how to stop it from growing
up with us. At a certain point, the company got
bigger and we went into other businesses and I let
(17:49):
it go. It was no longer you know, a reflection,
a reflection of me, thank you. That was what I
was looking for. The things that we realized over time
were the lifestyle that we were promoting and celebrating was
again it was about experiences and about every day being
better than the last, and doing the stuff that you love.
(18:09):
That's not for guys, that's just for people. That's a
much broader audience. And so when we realized that our
mission was one where we didn't have to contort it
in order to make it applicable to a broader audience,
we gave ourselves permission to let it be for a
broader audience, and that has served us well. Just hold
(18:30):
on a second, because we've got so much more to
talk about. We'll be back after a quick break. Welcome
back to Math and Magic. We're here with Ben Lair.
You have a bigger than life dad, Ken Larry. He's
a chairman of BuzzFeed, Blade, and god knows what else.
He has always been on the cutting edge. He Foundedfington
(18:52):
Post with Arianna Huffington. He was in the c suite
at a O L and it's Heyday at time one
or two before that, he had a huge communications company,
and indeed he was working with Microsoft and Bill Gates
when they sort of became icons. Right before I go, well,
what did you learn from your dad? He's really good
at just cutting to the core of an issue and
(19:13):
doing away with a lot of the waste and getting
to what's important. And so that's something that I try
to do as well. So that's the thing in business,
But you know, the business advice is secondary. The thing
that I've taken from him is how to prioritize business
visa v. Your family, Because I'm a much better business
(19:34):
person when business comes second. If I'm settled with my
family and I put my kids to bed every night
and like in that rhythm and and always putting family first,
then it allows me to put business in a much
healthier place and make much more rational decisions. So your
dad was, I know, a great role model for you there.
The family always came first to him. Um and when
(19:57):
your mother was away, uh, he would sneak you off
to mc anmods to have the forbidden foods. True. Talking
about your family, how do you think about work family balance?
And what do you recommend to the people you work
with and the people who you give advice to. I
don't have a specific like here's how you should spend
your time, but I would just say that family needs
(20:21):
to come first. For me, what that means is I
put my kids to bed. I'm with them every morning,
and then I put my kids to bed four out
of five week nights, and then by the way, I
go back out. So tonight I will go home, I'll
be home before seven o'clock. I'll put my kids in bed,
I'll have half an hour with them, and then I
have worked dinner. But that for me is like a
(20:43):
really important thing that grounds me. And also and with
my kids at seven in the morning, I don't want
to say I'll see tomorrow. That's how I've built my
calendar and how I've structured my work life. And I
have two jobs investing in running Group nine. You know,
my days are booked to the second and I book
my family into that day. It's really easy to just
(21:06):
let the calendar fill up and not make that a priority.
But that's something that I won't I won't do. Do
you put your phone away when you're with family? Yeah?
I try to, and there are days when I forget
to do your kids remind you? My kids don't remind
me to put my phone away, except my kids want
to pull it out of my hand and play with it,
which is very depressing. We live in a confusing world
(21:28):
right now. The addiction of technology is is horrifying, and
so I really have to set boundaries for myself. I
don't sleep with my phone in my room anymore. Do
you have an alarm on your phone? No, I have
an alarm clock. I'm like, what from blood eyed? I
hope it's a clock radio. It's a clock radio, except
I don't know how to set it, so it just
goes set it to Elvis Duran in the morning, or
(21:49):
the Breakfast Club or one of our other great shows
here in New York. And so about ten years ago,
INC Magazine picked you as one of their thirty under thirty.
But it was also about the time you started Layer
of Ventures with your dad. Tell me about starting that
and how you weave that into your jay job. Running
thrill list. New York was at an interesting point ten
years ago where New York wasn't a TechTown yet and
(22:12):
I was starting thrill lists and my dad had started
huf PO as you mentioned, and my dad actually just
had a super interesting insight, which was your friends or
my friends were leaving good schools and instead of wanting
to go and work on Wall Street or work in consulting,
they wanted to go work at startups or start companies.
(22:33):
And he said, that's crazy. I've been working in New
York for thirty years. I've never seen any smart young
kids want to go start companies. There's something happening right now.
I said, that's a very nice idea. Can you leave
me alone? I have to go back to work. And
he said we should invest in some of these companies,
and I said, okay, I'll let you know if I
see any companies that are interesting. We were making little investments,
(22:54):
and then a few months later we looked at the
investments that we had made and we figured that they
were actually pretty interesting. So we decided to raise a
little fund. You were one of our first investors, and
it was really friends and family who gave us a
little bit of money, and we use that money to
hire one person to sort of help professionalize and institutionalize
what we were doing since we both had other jobs.
(23:15):
It's just so happened that that vintage was BuzzFeed and
Warby Parker and this awesome generation of New York startups,
but in particular iconic consumer startups. And so what happened
was we got our brand and our name associated with
these companies that became sexy and exciting, and so right time,
(23:38):
right place, we suddenly so I had everybody who wanted
to go build the Warby Parker of whatever calling us,
and eight funds later, it's worked. It's been amazing, and
we built this great team and we've been able to build,
you know, arguably the strongest brand in early stage New
York investing, which is nuts. It's impressive. It's impressive. So
(24:00):
contrast being an investor with being an executive. My best
and worst days are being an executive. It's harder, uh,
but when it works, it feels good. So that's the
short version of it. I think that investing you don't
feel that. So if you make a sure bet and
it fails, you go. We make an amazing investment and
(24:23):
it fails, I go, they screwed it up. Of course,
I don't like to lose, and I'm so happy when
these companies become big and special and The reason I
said Casper earlier is because that was one where we
from minute one were the lead investor, and we don't
take board seats sort of as a principle because of
the number of investments we had, but that's the one
(24:44):
board seat I ever took from day one, and that's
turned out to be such a fabulous company that it's
been just a really cool journey to be on. Do
you sleep on Casper, of course, and if you don't,
that's come on. I know Neal would kill me if
I could thank you. So what's your investment process? It's
very collaborative. There are four partners, three managing partners for
(25:05):
total partners, and then an investment team of five other
folks who are all really smart and really different different
areas of interest, areas of expertise, generations, and so we
have these interesting perspectives. And then we have a three
person platform team and a two person finance team, and
we all have a partner meeting together and we talk
(25:27):
about what we're looking at together. We don't do any
deals that multiple partners haven't met with. It's not a
consensus driven model, so anyone can lead a deal, any
partner can any partner vito a deal. Any partner can
veto a deal. We don't formally use table pounds and vetos.
We sort of agree to disagree and then someone goes
(25:47):
forward with an investment or not. You know, we make
about twenty to twenty it's called twenty new investments a year,
plus a bunch of follow ons, and so there's a
lot of velocity. If we love something, we'll do it.
We try not to invest in competitive companies. Were incredibly
founder centric. The place where I think we really win
is in having empathy because we know how hard this is.
(26:09):
I know how terrifying it can be to build something.
And so when times are good, everyone loves their investors
because their investors are cheerleaders. When times are bad, that's
when you really understand what kind of an investor you have.
And I think that we are pretty understanding and sensitive.
We don't like it when stuff goes wrong. And obviously
if we think someone is being fraudulent or really irresponsible,
(26:30):
that's not good. But if people are really trying hard
and doing the best they can and things don't work out, like,
that's okay, and we'll back you next time again. So
you're an operator, yeah, everybody there is basically an operator.
As investors, how do you bring that expertise to bear
on your investment so you're not just money. It's a
great question. So there's a few ways that we do it.
One is real institutionalized structure. We have a support team.
(26:55):
We're creating events for people to meet one another. We
have forums where ers are asking each other, in some
cases really hard questions, in other cases recommendations for a vendor.
We have a full time recruiter senior recruiter on our
team who parachutes into companies, and so when we invest
over the next few quarters, it's very likely that we'll
(27:17):
send a recruiter in for three months part time to
help you build out your executive team, get your feet
under you in the early days. We have a process
for leaning in really hard around helping a company prepare
for its next round of fundraising as it relates to
pitch practice and building decks, and so there's this sort
of more structured piece, and then there's the much less
structured piece, which is how are we there when they
(27:40):
need advice from somebody who's maybe seen this before and
who's going to have an incentive to really care and
so we're available seven and I never know in a
day whether I'm going to talk to one of our
founders or whether I'm going to talk to I mean,
I might talk to none, I might talk to four.
But generally speaking, the model is that companies graduate weight
and so we're with a company through a seed round,
(28:02):
they raise later stage financing. They have a Series A
or Series B investor who owns and just put a
bunch of money in, and there is somebody else who's
the sort of primary board member. And that's what enables
us to overtime build a larger and larger portfolio and
still feel like we can deliver the level of service
that we owe the founders. So there are people listening today.
I'm sure we have an idea. They've got their thrill
(28:24):
list in their head. What is it that grabs an
investor and what is it that turns them off? I mean,
it's a little bit like dating. You just feel it
or you don't look. You need to be really passionate
about what you do, really knowledgeable about what you do.
There's a balance that we like to see around having
very strong conviction for what you want to build, but
(28:47):
not so much conviction that you seem unwilling to examine
other ideas or viewpoints. We sort of believe that every
one of these companies has to pivot. It's some point
in some way, shape or form, and so you want
to see that sort of flexibility or malleability, but not
so much that they come in and they say we
(29:08):
want to build this thing and it's black, and I
go what about white? They go yeah, yeah, wait, So
that's the that's the balance. It's just somebody who has
a head on their shoulders and a belief in what
they want to build and can articulate why they want
to build and why it's a good opportunity, and you
believe that they're going to walk through walls to get
it done. But I will say being more prepared and
having better materials and having a vision for what the
(29:31):
business is gonna look like. And you know, if you
want to raise one and a half million dollars, I'd
like to understand why that's the right amount of money
and how long it's gonna get you and what the
different outcomes might be from that. But I'll forgive some
lack of technical knowledge or business savvy if it's somebody
who I think has such a keen understanding of the
consumer that they're going after the market that they're entering,
(29:53):
so there's no formula. What's more important as an investor,
the person or the idea. I think that the person
is more important. Right now, we're investing in people we
love with an idea we like. Okay, And we talked
about this for a long time in the partner meeting
because we said, oh God, they're so compelling, they're so smart,
they're what a great team. This market's not awesome. Yeah,
(30:16):
but they're gonna pivot and we love them and we
don't want to miss being in business with them. And
even if this isn't the one that gets there, the
next one will be. And if we take a slightly
longer term approach, these are people when we want to
be in business with. You would never say that about
an idea and go, uh, this idea is gonna be awesome,
even though we think these people are terrible in fraudsters.
(30:37):
This podcast is about math and magic. Let's talk specifically
about the math. How much were you looking at data
in the early thrillerst years, as much as anybody else
doing what we were doing at that point. What kind
of information did you look at to inform you besides
your friends say wow, Ben, you're doing a great job.
I mean, there was a lot of anecdotal information about
(30:58):
the impact that we had on the business says that
we covered. That was really important because there was something
in that that measured trust. You know, we did a
lot of studying click through rates, share rates, and unsubscribed rates.
We did, I think, as good a job as we
could have with the resources that we had to sort
(31:18):
of study our subscription funnel and to look at the
efficacy of some of the partnerships that we built. But
in reality, it was just a much less data rich
world back then, and so Thrillist was built with enough
data that we weren't blind, but a lot more of
the magic than the math. Today, you're running a lot
(31:39):
of businesses, they're all in this data world. What data
do you look at? And what's so important to building
these businesses? Now you know there's enough data you can
you can hang yourself with it, right, And so now
the question isn't are we using data? The question sometimes
is are we using too much data? And what do
you think? Well? I think that the answer is often
(32:00):
that we are using too much data. I don't know that.
I would say that in our specific business, we're using
too much data. If you know something's good, you know it,
and the data says it's not that good, I still like, okay,
So the data has got to catch up because I
know it's good. And sometimes there's something that I know
isn't very good and the data would say that audiences
(32:20):
love it, and I would go, there's no way this
is just like, audiences don't love this. I get that
there's a lot of views, but this is not the thing.
So will you go with your gut? And I will
go with my gut. That's on one side of the business.
I think in the advertising business right now, data is
a terrifying, terrifying thing. Why Well, just because everything in
digital is just right to the lowest common denominator. Almost
(32:44):
all money being spent digitally is being spent blindly. Do
you think Google Search gets credit for a lot of
attribution that they didn't cause? Look, I think Google is
a good ad product, but we're in a last click
attribution world. So whoever's got the last click totally totally, totally, totally,
(33:07):
totally crazy. And by the way, if I'm a Marketer.
It's hard to turn off the drug that some of
these things create. You started out with the newsletter, somewhere
along the way you added video, get it all sorts
of stuff. Talk to me about audio, obviously, I've got
a self interest here, But podcast, Alexa smart speaker, How
(33:29):
does it all fit together? And what do you think
that is telling us about the marketplace? Yeah? Well, I
mean starting with podcast, I think it's just a super
compelling medium and it's something that we're investing in and
looking at doing and hopefully we're gonna do some stuff
with you guys, which is really exciting. The data is
overwhelmingly clear that this is a preferred format for young
(33:50):
folks to get content, and it's a big part of
their commute. And I think it works well with the
kind of narrative storytelling that we do and the kind
of voices and personalities that we have, and the kind
of brands that we have. So I'm a big believer
in that. Let's get to future of the media business.
Where do you think all this goes? I think it's
all Number one on Alexa mm yeah, number two. Weather.
(34:14):
I wake up and do weather, and then my kids
listen to Mo wanna We'll get them. Okay, you'll love it.
That's the deal um future of the media business. I
think that more consolidations coming. I think more consolidation up
in the stratosphere is coming. I think more consolidation in
digital is coming. I think content creators and pipe owners
(34:36):
continue to join forces. I think if you're a consumer,
it's awesome. There's gonna be a lot of great content
for a long time. And you have companies that don't
even care about the media business who are going to
spend billions and billions of dollars underwriting content to get
you to do things on their platform that have nothing
to do with advertising or content at Allso great time.
If you are a consumer, if you're in the media business,
(34:59):
it's it's a chow vallenging time. There's always going to
be good businesses to be built on brands that people love,
and so it may not be as simple as it
used to be with dual revenue stream model, but I
think media companies are gonna have to be good at
a lot more things simultaneously than they used to be
right now, and they're gonna need to figure out ways
to directly engage their audiences and sell things to them
(35:23):
while also selling advertising, and also creating experiences, and licensing
and selling I P and working with the distribution platforms.
I mean, it's just a it's a confusing time, but
I think it's a very hard time to be in
a small independent media business in any category. This is
math and magic. Who is the greatest mathematician, you know,
(35:46):
that person who plays the math side of the equation best.
There is a guy on our team who runs data
and analytics and research and who's one of our executive
team members. Names is Shesh Patel. And he is somebody
who everybody in our company looks at as being an
amazing math leader. Who's the greatest magician? Who's that creative person?
(36:11):
You know? You still gotta go back to like Steve Jobs, right,
he might be a little bit horrified at what the
creation is being used for now, but that changes the
world Like nothing has ever changed the world. There's still
nobody that's done anything close to that as far as
I'm concerned. Ben Lair, CEO of Group nine, founder of
Thrill List, someone who's gone from being young turk to
(36:34):
establishment one of the real geniuses of the business. And
thanks great being here. Here's a few lessons I take
away from this episode with bem use. The of the
decisions are easy to green light. Of the decisions are
easy to kill. But SI is the gray zone that
(36:54):
takes up your time. Get things out of that middle.
Decisions about people can be hard, but it's better to
make quick decisions and not just postponed the inevitable. And finally,
Ben's philosophy is that it's more important to invest in
the person and the idea. A talented person or team
can always pivot, and you don't want to miss an
opportunity to work with the right people. Thanks for listening.
(37:18):
I'm Bob Pittman. That's it for today's episode. Thanks so
much for listening to Math and Magic, a production of
I Heart Radio. The show is hosted by Bob Pittman.
Special thanks to Sue Schillinger for booking and wrangling our
wonderful talent, which is no small feat. Nikki Eatre for
(37:41):
pulling research, Bill Plax and Michael Asar for their recording help,
our editor Ryan Murdoch, and of course Gail Raoul, Eric Angel,
Noel Mango and everyone who helped bring this show to
your ears. Until next time,
Host
Bob Pittman
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