Episode Transcript
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(00:00):
You want something like 6 to 7 out of 10 peopleto think it's a bad idea.
Mister Andy Dunn, the $300,000,000 founder ofBonobos.
I had him here at our studio in Manhattan toask him everything he knows about being a
successful entrepreneur and making 1,000,000 ofdollars online.
How did you go from selling these pants out ofTrader Joe's bags to then making your first
(00:22):
million in revenue?
So the equation early was
You went to San Francisco and got devastatingnews on that trip.
There were questions.
Is this the end of bonobos?
That was the year where we had cofounderdivorce.
At times, I didn't wanna live because I had Iwas so depressed.
You ended up selling to Walmart for about$300,000,000.
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How did you come across Walmart?
So I I get a phone call one day from a guynamed Preston.
Andy, I wanna start this episode with your timeback at Stanford Business School.
You had $3,000 in your bank account.
We're a $150,000 in debt.
And your roommate, Brian Spalle, was starting aside hustle selling pants out of Trader Joe's
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bags.
Little did you know this would turn into abusiness worth 100 of 1,000,000 of dollars.
Tell me about that 1st year.
What was happening in your life, in and aroundyou, and what did it look like in that moment?
It's funny when you say that since it was, Idon't know, 17 years ago now.
It doesn't even sound true.
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You know, I think about it, it doesn't soundtrue from Trader Joe's bags.
The 1st year was so fun.
And by the way, not every year was fun, but the1st year was so fun.
So we were in Silicon Valley.
We were at Stanford.
It was a time of great innovation in theconsumer Internet world.
Smartphones just launched.
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Google acquired a small company called Android.
Facebook had been founded a few years earlier.
Instagram didn't exist yet.
So it was a time of great consumer innovation,and I really wanted to work for a consumer
Internet company.
So I interviewed at Yelp, I think I got anoffer from Yelp, I interviewed at Facebook,
didn't get that job.
That was the track that I was on.
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And then Spaley starts selling pants out of histrunk and out of these, you know, grocery bags.
And I watched him rack up maybe $40,000 ofsales to our classmates at Stanford.
And by the way, if you sell $40,000 worth ofproduct to your friends and it's legal, there
might be a business there.
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Right?
I mean, that's a lot.
If you think about it, that's not people doingyou a favor, that's people wanting the product.
You've got product market fit.
So I began, in conversations with him, to sortof have a twinkle in my eye of, maybe this is
the consumer Internet company I've been lookingfor.
Maybe the idea is to take a physical productand sell it online.
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And what was interesting about doing that now,because I don't think that sounds terribly
interesting in 2024, but what was fun about itthen is it was contrarian.
And that same professor used to talk about howyou need to be non consensus and right to build
something innovative.
So, in fact, you want something like 6 to 7 outof 10 people to think it's a bad idea.
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And obviously, you're very fortunate if peoplegive you that candid and honest feedback.
And the reason why people, many didn't thinkthis was a good idea is that there was no
antecedent for a brand that had been builtdigitally first.
At least that I could find.
There wasn't an example of starting on theInternet.
There were plenty of brands that were extendingonline.
Right?
J.
Crew had a website, Banana Republic had awebsite, but there wasn't an example of someone
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who said, we're gonna start on the Internet.
You sold $40,000, and and Brian sold $40,000worth of pants out of these Trader Joe's bags,
which you say is, like, okay.
That's pretty impossible to do or or verydifficult to do.
Why didn't he have the conviction early on?
Because he didn't start the company.
Right?
He handed the CEO position off to you.
It was a funny time because I had introducedBrian sometime, I think, in our 2nd year, to
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the private equity fund that I worked at priorto GSB.
And I didn't wanna go back to that fund, Ithink actually they told me, look, we'll
sponsor you while you're at Stanford to return,but you'll you're the worst private equity
associate we have ever invited back aftersponsoring business school, which was kind of a
fun relationship that I had with the founder ofthat firm, which was like, he was super candid,
he was super candid.
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We had a really good vibe, but if I'm honest, Iwasn't that good at private equity.
I think I only got to lead one deal while I wasthere, and I think that ended up at 0.5 times
cash on cash.
Like, it didn't end up well.
The only ones that might have done well wereconsumer deals where the the fund didn't wanna
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pay, you know, the profit multiples that itwould have required.
So maybe I could have been good if we wouldhave been a little bit more spendy and focused
on consumer, but we didn't.
I felt like I wasn't good at the job.
I didn't love it.
And so, I was thinking, I wanna buildsomething, or I wanna become a consumer VC
because I wanna be able to fall in love withthe company at the beginning of the life cycle
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rather than buy it down the road.
And Bailey was more thinking about going backinto finance.
So we had very similar convergent backgrounds,which I think plays into the story of some of
the challenges downstream.
He also had his first job at in strategyconsulting at Bain.
He also was there for a couple years.
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He also then went to a private equity fund.
He also then went to Stanford.
We were roommates, so we had very convergentbackgrounds.
And I think the difference between us was, hewas open minded and curious about going back
into finance.
He did a summer internship, I think at T.
Rowe Price, and then he met the partners at thefund that I worked for, it's a fund called Wind
Point, and he got an amazing offer.
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I think he got an offer to be a vice presidentor a principal.
At some point, he took that offer, and then thepants thing became kind of a prod a side hustle
that started to work.
And so, I think it was loyalty and obligationand duty that he felt to honor that job that he
accepted.
And, I guess in his telling of it, I don't knowif it's still true, you know, I see him once in
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a while now.
He felt like, I trust Andy to take this and runwith it.
And we agreed that if it got to call it1,000,000 in revenue run rate, or 2,000,000
revenue run rate, perhaps he would come back.
And in the meanwhile, he would participate andhelp as much as he could, he would fly to New
York on a Friday, and work all weekend with me.
And so that was this interesting moment wherehe passed the baton to me, or the torch, and
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the idea was you now carry this, I trust you,and if it starts to cook a little bit, then
I'll come join you.
And that actually is, in fact, exactly whathappened.
So you flew to New York to start selling thesepants in the city, but you didn't have enough
money of your own to actually start it.
Where did you get that initial funding from?
It's funny, my team now at my new company jokesometimes that I'm spendydone, not andydone,
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because I like to spend money.
I'm really weird.
I like to in my mind, it's stimulating theconsumer economy, and I like experiences.
So I'm the person that's, like, let's not justgo to the US Open, let's sit in the 5th row.
And I don't think I can afford longitudinallyto sit in the 5th row, but I like to spend,
which is not a great quality in anentrepreneur, and I've learned over time to
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sort of fork my personal habits for myprofessional approach.
And and then in my personal life, we could talkabout it.
But I basically give my wife the keys to ourbalance sheet so that there's we have kind of a
deal of if it's gonna be over a certain amountof money, she has to approve the expense.
So I think that when I came to New York, thereason why I was able to do it was that we had
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secured enough angel investment to be able topay me a salary, buy inventory, and hire one
person.
That was the budget that we set up.
And it was, I think, $300,000 that we raised,100,000 from Joel Peterson, who was then the
Chairman of JetBlue and a Stanford professor,100,000 from Andy Ratcliffe, who was one of the
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co founders of Benchmark, and, now chairman orCEO of of Wealthfront or some combination
thereof.
And then once they our classmates who were ourcustomers, which were other guys who were 2nd
years, started hearing that Andy and Joel, whowere these revered professors were investing.
They were like, I think I'm in.
And so the first maybe 100 k came from Spaleywho was a much more frugal person than me and
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it saved a lot of money when he was abandonedin private equity.
And who had been better at private equity andtherefore had made more money in the process.
And then the next 300 was from our Stanfordnetwork, Stanford community, and that was kinda
lift off.
And you were able to disrupt the industry in away that was it was a more stagnant category.
Nobody was really paying attention to ecommerceor or selling pants or selling clothing online
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that much at the time.
How did you do that?
How did you break in?
And then what was so special about what youwere selling that, other investors wanted to,
take the dive in with you?
I mean, look.
I think pants is a sexy category.
Like, we called the brand Bonobos, which is apromiscuous chimpanzee.
Guys look guys feel more confident if they aredressed in well fitting clothes, and that was a
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big trend at the time was that more or lessstraight guys didn't care about how they looked
from a fit standpoint.
I mean, think about the way, like, I don'tknow, maybe your dad dressed.
I can certainly think about the way my daddressed, which was, like, pleated khaki shorts
down to the knee, and then striped socks up
to the top of the cap.
Yeah, this was the vibe.
It wasn't a thing growing up for thatgeneration to care about how they looked.
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And that started to change, I feel like, youknow, around the time, let's call it like the
nineties and the early 2000s, where it startedto be like, okay, if you're going out at night,
you can't always wear a black button down injeans that don't fit you well.
So, in a way, I think it's a sexy category,right?
But I think it's been viewed historically as anon sexy category.
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I mean, how much innovation did we have inmen's pants?
Maybe none since the toga, right?
At some point we cut over from stuff that thethe toga converted at some point to pants, and
really the first innovation was Levi's.
Right?
It was the innovation of denim, and whathappened in the nineties and early 2000s was,
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you had new innovation in denim from the Levi'sera, which basically was about stretch.
It was stretch going into the product that wasfor people that could afford it.
The premium denim movement, which was 7 For AllMankind, Rock and Republic, AG, all of a sudden
you had guys in a certain demographic spendingover a $100 for a pair of pants.
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And I remember my dad saying, are you on yourmind?
Like you're gonna spend over a $100 of my firstpair of 7 For All Mankind jeans, maybe that was
high school or college.
And so we, Brian, had noticed that that hadhappened in denim, and wondered why it hadn't
happened in wool pants, and tailored pants, andchinos, and khaki pants.
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And that was part of the innovation of bonoboswas bringing stretch into those categories, now
you can get stretched chinos from anyone.
Like the whole world of, chinos is stretchedchinos, but that was early, and we could talk
if you want, about the other innovations in thepants, like a curved waistband, peek through
print patterns in the back pockets.
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There was a host of things that went intofocusing on something that someone that no one
else was focused on.
And how did you go from, I guess, selling thesepants out of Trader Joe's bags to then making
your first million in revenue, especiallyonline?
Like, what what were the steps there and maybethe frameworks that you guys built out to make
that happen?
So the equation early was our own directselling and then organic PR.
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I can still remember to this day, one of themost exciting days of my professional life
anyway was somebody somehow heard aboutBonobos.
We were selling literally just to friends andfriends of friends and friends of friends of
friends, and there was a a men's wear, or no,there was a men's blog called Urban Daddy.
I don't know if it's around anymore.
And Urban Daddy dropped an article, title Ithink was Monkey Business, it's probably
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somewhere on the internet still, and it wascoverage about bonobos.
And I remember our website crashed.
I was at the Heartland Cafe in Union Square, Iwas sitting with our accounting firm, trying to
figure out how we account for the early revenueand the early costs, which were all sitting in
the spreadsheet, and Dane Hucklebridge calledme.
Dane was our first employee, he was a Princetoneducated novelist, He wrote our blog.
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He doesn't have much interest in capitalism.
And he calls me, he's like, Andy, we're gettinga couple orders an hour.
Should I shut the site down?
Because he was worried about his ability to dothe fulfillment, because he was doing the pick,
pack, and ship, which he would do laying outpants and USPS envelopes on my bed.
You know, once the workday started, that'swhere the pick, pack, and ship happened.
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Because our inventory was in my bedroom, 400pairs of pants on the walls of my bedroom.
And I'm so bummed, I don't think there's aphoto of this.
And so, that was the beginning of realizing,wait, the way you move the needle to get beyond
your personal network is PR.
And so, called up a friend who was, the wife ofone of our business school classmates, she had
a PR firm, Her monthly retainer was 3,000.
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I felt like we couldn't afford 36,000 run rateon $300,000 fundraise.
So I asked her if she'd do it for equity and1500 a month.
She was like, Andy, 1500 a month is really notenough, but I'll try it.
And then she just made it rain.
You know, we were in the New York Times, wewere on TV in the back of taxis, we were in all
these places we didn't deserve to be yet.
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We were on the Today Show, and that was thebeginning of realizing that a lot of the way
fashion works is through PR.
It was before Facebook launched its adplatform, which then became the next way that
we grew.
Why did these news publications, like the TodayShow and and New York Times, why did they pick
it up?
What was so special about your story that theywanted to share about it?
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I'm a big fan of the book Made to Stick by Chipand Dan Heath.
I think it's been a while.
I maybe it came out 15 or 20 years ago, and ittalks about, like, the ingredients in making
something sticky and conversational.
One thing is a name that is memorable and maybeeven controversial.
And so I remember sitting at one of my firstdesk sides as they call it, where you go and
sit next to a reporter, you know, fashion pfashion writer.
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And I don't remember which one it was.
I think it was it was the men's one that waskinda like the men's WWD, the women's wear
daily.
I don't think it exists anymore.
And I'm sitting at a desk, like, in a chairright next to the person that would write the
story, and I'm showing him samples of theproduct.
It's so funny, like just showing samples.
He or she said, why did you name your brandafter a monkey that likes to have sex?
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And there was a little bit of condescension inthe tone, like you're kind of a frat bro, which
I think was more or less empirically 100%correct, you know, at that at that certainly at
that stage of my life.
And I just said, I didn't know what to say.
And I said, it's actually an ape, not a monkey.
And then we talked about primatology, but thefirst thing is a memorable name with a story.
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And what we talked about, and Brian picked thename, of course, his brand out the gates, that
it was the Make Love Not War Ape.
And there's so much cool stuff about bonobos.
One of which is they have a matriarchalsociety, and therefore they have no violent
conflict.
Whereas chimpanzees have a patriarchal society,and they kill each other the way that he you
know, homo sapiens kill each other.
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So it just was sort of a fun conversation tohave about the name of the brand.
The next thing I think was, it was unexpectedthat 2 people from the NBA world were working
in fashion and apparel.
We we didn't sound like the typical people herewho come up through FIT and launch a brand.
And so, I think that was an asset because wewere going right to the customer directly, who
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were our friends and were in our demo.
So I think there was something to theword-of-mouth there.
Then there was another thing, which is we wereobsessed with customer service.
We had, at the time, a team called the Ninjas,and we would reply to people within 2 minutes
of emailing us.
And I remember people thinking, wait, you'rethe CEO?
Because I had it in my signature, and I wantedto be, like, I'm actually the only person that
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works here.
But we paid a lot of attention to the earlyservice to create the word-of-mouth.
I can remember, we made a pair of pants withalpaca fabric, way too much of it, a 100%
alpaca.
This guy calls me, his name was Matt and goes,Andy, it's raining, I'm on a date and I smell
like a llama.
And it turns out that in fact, if you makesomething with a 100% alpaca, you'll smell like
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a llama.
And I was, like, where are you?
And he said, I'm by Irving Park.
And I said, I'll be there in 5 minutes.
And I grabbed a pair of pants from my shelf,and I came with a bag.
At this point, I think we had something betterthan Trader Joe's.
And I was like, here you go.
And then he went in the bathroom and he changedand gave me back the llama smelling pants and
went on with his date.
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So I think if you really treat customer serviceas important as the product, that's buzzy.
And then I think the last thing is where westarted, which is it was just super weird that
it was a digital first brand.
I can remember when we met people in thefashion industry in New York, they would hear
about Bonobos and they would say, where do yousell?
And I would say, well, we don't actually sellanywhere, you know, in the physical world.
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And it would be I would get scoffed at.
Like, your brand is nothing, you have nodistribution.
And I would say, well, we're we're focused onselling on the Internet, and that just wasn't a
thing at that time.
And so it was sort of a host of memorablethings together and made to stick talks about
this, which is you need 4 or 5 or 6, like,touch points or hooks on why something is
different.
And then it becomes something story tellingworthy.
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And that means one person will tell anotherperson, which is sort of the definition of
virality in consumer.
Yeah.
I just did an interview with this guy named,Anthony Pompliano.
So he's made a ton of money generally throughcrypto.
He was on Lex Fridman show.
I think he's worth around $100,000,000.
He operates a bunch of businesses, at hisoffice in Midtown.
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And I asked him, why do most founders, like,fail?
Why do they not make it?
He's like, there's two reasons.
1, of course, which was the biggest one is thattheir pace of execution is just slow.
So he credits Sriram from a 16 z about this asthey generally have a low clock speed.
And he would tell people on our team, so he'slike, hey.
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He'd maybe ask somebody else on his team.
It's like, hey.
Could you do this exercise real quick?
When could you get this done?
And the person would be like, oh, we couldprobably get it done by Wednesday.
He's like, could you do it by, like, 3 PMtoday?
He's like, oh, sure.
He's like, why isn't that the default answer?
How important do you think speed is, as afounder?
It's one of the 2 key things at the beginning.
I don't know what the second thing he said was,but rate of iteration and grit, I think are 2
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of the key key 2 key ingredients.
I think there are personality traits that areimportant, magnetism, tenacity, authenticity,
the ability to evolve, but you can have someonewith that personality, you know, those
personality attributes who doesn't iteratequickly, tenacity and grit are a little
redundant.
And it's actually one of the reasons why wemoved from building PIE, my new company, as a
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remote company, to in person, because I'm notI'm not high conviction, at least for me, that
you can iterate quickly enough through digitalrelationships.
I think the ability to accelerate conversationswith actual whiteboards, not digital
whiteboards, and feedback, and socializing,informal conversations, speeds you up.
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And I think that's so critical.
So I'm a 100%, you know, with Sriram, and withthe guy who was on who you mentioned.
And and I think, candidly, we were wanderingthe desert with my new company, Pie, for 4
years because the rate of iteration was tooslow.
And now we're now we're cooking, and we'regrowing, and I don't think I think those things
are correlated.
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As you were building out bonobos, what weresome of the things that you were trying and and
experimenting with?
You mentioned you probably spent a lot of moneytrying to build out the platform, and I'm sure
there are things that didn't work.
What were some of the things that didn't work,earlier on in the business?
One of them was having the delusion thatBonobos was a tech company, not a pants
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company.
And I think in a lot of ways, this was naturalbecause for me, the origin story of wanting to
do this was I was obsessed with the consumerInternet.
We also had investors from Silicon Valley,which by the way, was a huge unfair advantage
in building an apparel brand.
It is very hard to raise money as an apparelentrepreneur.
And if yet, if you have even half a $1,000,000that can be so critical to hiring that first
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person being able to buy 50 or $100,000 ininventory.
So it was a wonderful and fair advantage, butit came with the price, which is that I wanted
to build a tech company in a lot of ways.
That was a tech enabled retailer, where thewhere the technology was gonna be critical to
what we did.
I think I remember talking aboutpersonalization from the first deck, which is
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we're gonna be able to figure out so much abouta person and serve them a personalized catalog
that was, which was a leap from the old schoolcatalog business, which was like the OG direct
to consumer approach.
And I had worked at Lands' End my 2nd year atBain, so I understood the direct to consumer
catalog business.
And I remember looking at the top 25 servicecompanies of any kind and seeing Lands' End and
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L.
L.
Bean as the only 2 apparel brands on the list.
And I thought, what do these 2 brands have incommon?
And it occurred to me, which was they didn'thave physical distribution.
They had a direct relationship to the customer.
And this one particular winter, cold winter inDodgeville, Wisconsin, in I'm a Bears fan in
Packer territory.
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I learned so much because I I was at Lands' Endevery day.
It was after Sears acquired Lands' End.
And I remember one day walking into theircustomer service center, because back there was
call center, and seeing all these notes on thewall, thank you notes.
And one said something like, dear Elizabeth,thank you so much for waking me up the morning
of my wedding.
My bridesmaids wanted to sleep in.
My mom was a mess.
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You're the best.
And I remember thinking, this is wild.
This bride called Lands' End's call center andsaid, can you call me tomorrow morning at 8 and
wake me up?
We've got one of those I can share fromBonobos.
Let's start with the story.
What was one of those stories?
Oh, so this is a sad story, but we had acustomer who lost his dog in a fire And the
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fire burned down, whatever the apartment, losthis dog and lost his wardrobe and wrote in and
basically said, I lost all my clothes and Ican't, I'm in a tough spot.
And so of course we sent him close.
We just we had a a view that you've gotta pushdown in a customer service environment, the
autonomy, and the ability to do stuff all theway down to what we call the ninja at the time,
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and not need a manager, let alone bubbling upanyone to approve it.
And so it was normal that we would like sendsomeone a 6 pack of beer or a book or give away
a free pair of pants.
And we had the data to back up why one shoulddo this.
You know, I think the average bonobos customerlifetime value for our best customers was
$2,000.
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So what's, you know, a couple free pairs ofpants at costs, not a big deal.
But with this particular case, it wasn't justabout the product.
It was this, you know, tragic loss of a pet.
And so the ninja who was brilliant, said, oh,would you why don't you send us a picture of
your dog, just so we can, you know, have amoment reflecting.
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And they had a reason for that, which is theywanted to commission a painting.
And so they commissioned a painting from afriend of a ninja.
Maybe it was, I don't know what was paid.
And they sent this painting of the dog to thecustomer.
And just, it was really memorable talking aboutthat.
I remember remember sharing the story with thecompany, and that was a moment that went viral
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within our company.
We didn't advertise it publicly because wedidn't wanna trade.
This is not about returning a tire.
This is about the loss of a dog.
So I don't think we ever traded on externally.
I guess I'm doing that now.
But but that was important to us to reallythink about being different in terms of the
customer intimacy and the way that weinteracted in a way that would be memorable.
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This is definitely not the same thing, but I'msure you saw what happened with Stanley when,
that girl's car caught on fire, and, she filmeda TikTok, and her Stanley Cup was still fully
intact after all.
Didn't see it.
Didn't see it.
No.
So But I love Stanley Cups.
Yeah.
So the car completely burst into flames.
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Literally, everything was burned and melted.
Wow.
But the Stanley Cup was completely intact.
Wow.
So she films a video of it, goes viral onTikTok, but that's not even the part that goes
viral.
The president, I believe, of Stanley respondedwith a video and said, hey.
So sorry this happened to you.
We're gonna buy you a car to replace it.
Yeah.
And gave her a new car.
It's, like, glad your Stanley Cup is okay, andthen also send her a bunch of Stanley Cups.
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Amazing.
I think that's where I'm sure there thereprobably was some marketing, like, behind it,
but it was more that they were authentic.
And I think that's where it's really importantfor founders to be authentic, but also know
that their customers are not just numbers on aspreadsheet, but they're also, like, real
people.
Real humans.
And to jump, trajectories here a little bit,when Brian returned to the company in 2008, you
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guys soon started to think about, okay, what'sthe next category that you're gonna go after
after pants?
Brian wanted to do swimsuits.
You had a different vision for the company andstarted to get depressed because of this.
You get a call from your investor that someonein the company overheard both of you fighting a
lot, in front of your team.
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What was going on there?
How did you navigate that?
Poorly.
I was approaching things without confrontation,and so he would say something that I perceived
as whatever, offensive or mean or that Idisagreed with.
And rather than, like, taking that to him, Iwould do what John Gottman calls 1 of the 4
horsemen of the apocalypse, which isstonewalling.
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Right?
You say something I'm hurt or upset, and then Ijust kinda go away and get upset and get more
and more upset and tell myself stories aboutthe other person until what do you do?
At some point, it boils over.
You, 1, I did, like, explode with all thesefeelings because they haven't been metabolized
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when they were at a lower level.
And I think more so than anything that we werehaving conflict over, which we could get into,
what categories to go into, how to hire, allthese things around.
I talked to you about, like, frugality versusspendiness.
More so than all of that, like, themetaphysical thing happening or the
(27:05):
undergirding thing happening was I was unableto be candid, and he was very able to be
candid, and that is a challenge in apartnership over time.
I was listening to Sam Parr, and he was tellingme early on when he was building out the
hustle, there were certain team members thatjust weren't working out.
And, he's like, okay.
I gotta fire these people.
(27:25):
But for some of those conversations, he wouldwait sometimes a year, 6, 12 months to actually
have that conversation because he didn't wannabe, quote, unquote, mean.
He wanted to stay empathetic.
How do you have difficult conversations whilealso being empathetic?
Empathetic?
I think you do it early.
I remember I was in one conversation and it wasreally dystopian.
(27:47):
I wanted to talk to someone about letting themgo.
And she was telling me a story about learningto communicate directly.
And she was saying, she had a mentor once whosaid, Get that monkey off your back.
If you've got a monkey on your back, everyonecan feel it, it's inhibiting you, get that
monkey off your back.
And I love the Sara Brill song Brave, itinspires me because she says the lyric is, Say
(28:10):
what you want to say, let the words fall out.
And I think when it comes to a difficultconversation, sometimes you don't know how to
say it, but you've gotta just let the wordsfall out.
So, for example, in a romantic relationshipthat's not working, you might say something
like, I'm not sure this is working, which is aheavy thing to say.
But it's certainly better than saying, I'mdone, or this is over, which would be kind of
(28:35):
my style.
It's sort of it's I call it the blind side.
You've got these feelings and stories thatyou're telling yourself things are happening.
You make a decision in your head.
You're like 2 months deep in thinking aboutthis, and then you basically cut that person
off at the knees.
And I once had a guy that I fired say, I feellike you're cutting me off at the knees.
Cause I literally just sat down and fired himwithout ever having given him any feedback
(28:57):
about it.
So I've learned, do it when you're a 2 or a 3out of 10 of emotions about it.
Because if you wait to 7 or 8 or 9 out of 10,when the words fall out, they won't be
productive.
How did you have that conversation with, withSpaley?
Terrible.
I got to a place where, you know, I had anhonest exchange with him in a very passive
(29:21):
aggressive way, which was over email when hewas on a production trip in China.
So he was on the other side of the planet forme to work up the courage, and I sent him an
email saying, hey, I've been thinking about ourpartnership.
Maybe we should split it between CEO andchairman.
I'm willing to take either side of the trade.
So what is that?
That's like being blindsided by an email whenyou're on the other side of the planet.
(29:43):
Because basically what I was saying was, Idon't wanna do this together with you anymore,
and one of us needs to leave.
That was the first element that was problematicwith it.
The second was I was being disingenuous becauseI wanted to be the CEO.
Then there was the coup that I was conductingbehind the scenes to convince people in the
investor group that he should go.
(30:04):
And then there was the conflict with the teamwhere there started to be issues between people
on the team and Brian or me.
And I was really leaning into what they weresaying about him, but not anything that might
have said been said about me.
And the very specific way this played out was Isaid, Brian, we should have a 360 degree review
(30:27):
on you.
And I remember going back to teach the quoteunquote bonobos case at Stanford, and I've had
some astute perspicacious students over theyears raise their hand and say, did you have a
review on you?
And I say, I'm horrified and embarrassed tosay, that's not what I was doing.
I was conducting a coup.
(30:47):
And so none of those are good ways to show up.
And then if we talk about verbally whattranspired, I was saying the kind of stuff that
no one should ever say to a friend or abusiness partner.
2008 was one of the worst years of your life,but 2009 was was worse.
You went to San Francisco and got devastatingnews on that trip.
(31:11):
There were questions.
Is this the end of bonobos?
Will you guys make it?
What was the news you got on the trip, and howdid you get out of it?
There were a lot of things going on around thattime.
First, the partnership was unraveling, and thatwas the year where we had cofounder divorce.
And I would say, the co founder divorce, whatpreceded it, which was a lot of, for the first
(31:37):
time in my life, catatonic depression, where Ididn't wanna go to work, at times I didn't
wanna live because I was so depressed.
And I remember I, you know, I I finally wentand got a therapist, which is something growing
up in the Midwest and in my family system thatno one does.
Still no one in my family gets therapy, evenafter I wrote a book about it.
It's like, am I the only person in this familythat actually takes care of their mental
(32:00):
health?
Like, did we learn anything from this?
You know, both nuclear family and extendedfamily, it drives me bananas.
So I finally went to see one, and this womansaid to me after a few visits, Andy, are you in
touch with anger?
And I said, what's anger?
I've seen people get angry.
And she's like, what about your anger?
(32:21):
And I was like, my anger.
And then it was, I'm so angry with where ourpartnership was.
And she said, anger can, if it's sublimated canturn into depression.
And that was a bit of a life raft in a good anda bad way.
The good way was I had a story to tell myselfabout why I was depressed.
The bad way was that it cloaked the underlyingissue I was dealing with, which was bipolar
(32:46):
disorder type 1.
And it can be true that both of these thingscan be true.
You can have a exogenous reason you'redepressed and an internal biochemical reason
that you're depressed.
So after Brian left, it got harder because allof a sudden there was no one to blame anymore.
You know, building a startup, there's a lot ofproblems and it's easy to blame it on someone
(33:11):
else.
In life, it's easy to do this.
And I like to say, and I don't know if it'sexactly true, that there are 2 kinds of people
in this world.
The kind that otherwise blame and the kind thatinternalize blame.
People that blame themselves by nature, that'stheir instinct, and people that blame others.
And both are problematic.
But I would say, otherizing blame on others isa less productive way to live because then you
(33:36):
don't have the agency to fix it.
If it's someone else's fault, how are you gonnachange them?
Whereas if you point the flashlight atyourself, okay, well, now you have the agency
to do something about it, even if you gothrough what I would go through and still do
sometimes, which is periods of self selfloathing and self flagellation and not really
loving myself.
(33:57):
So after Brian left, all of a sudden, thingsweren't great.
A bunch of things that I thought I was good at,it turns out I wasn't good at.
I wasn't good at hiring.
I was having to fire these people withouttelling them about it.
We had a lot of executive turnover.
The culture wasn't great.
The company wasn't prospering.
You know?
So all of a sudden, it was, what do I do?
(34:19):
It turns out that I may have been a biggerproblem here.
And I remember walking through a Bonobosliquidation sale one day, looking at the
product that we had been making and being like,this product is so much worse than once Bailey
was here.
Because Brian was the creative genius behindthe brand.
(34:39):
So not only in retrospect did I kick out aperson who was actually candid, well, I wasn't.
I kicked out the person who was the creativegenius and the product genius behind the
company because it was a tech company, and itturns out it was a pants company.
So if life was a Monte Carlo simulation, Iwould love to run a 100 a 100 simulations and
(35:00):
have Brian take the company in 50, and take thecompany in 50 myself, and see what actually
would happen.
And I suspect that it would have been verydifferent in a very positive way.
Would it have been a quote unquote betteroutcome?
I don't know.
But I think he would have done it differently.
And the proof is in the pudding because he wentand built a new company called Trunk Club and
(35:22):
did a fantastic job.
And I hate to say I'm competitive in this way,but I am.
He sold that company for $300,000,000 in halfthe time, with maybe less than 10% or 15% of
the paid in capital.
So when that happened, that was the real wakeup call for me.
And it took a while that wait, maybe in mywhole life, I've been the problem and I've been
(35:47):
blaming other people.
09 was the beginning of it being just me andstarting to go through that self loathing and
self doubt.
It was the real, it was the 1st year that I wasstarting to acknowledge I was very depressed.
And then the company was running out of moneyagain and again, because back to spendy done,
(36:07):
you know, I was spending a lot of our capitaland it wasn't translating into the kind of, not
just growth, but more, let's call it lessunprofitable growth that we needed.
And so again and again, we were going out tothe market with 6 weeks of runway, trying to
get more capital without doing a down round.
And, you know, as you know, that's wildlychallenging.
(36:28):
How do you get out of that dark place?
At the time, one of the ways I got out of itwas alcohol, which is not awesome.
So what would happen is I would go throughthese hypomanic periods, which is one of the
phases of bipolar.
And hypomanic is basically being in aridiculously good mood with high energy for a
(36:49):
100 days at a time.
So the the diagnostic criteria from thepsychiatric association are elevated speech,
the flight of ideas, relentless optimism,grandiosity, irritability with conflict,
decreased need for sleep, and then a bunch ofother not great stuff.
(37:10):
Financially irresponsible, promiscuous in one'sromantic life.
It's not awesome to be hypomanic at that levelfor that long.
And so during those periods, I would just jam.
I think during those periods, I was good atrecruiting, I would energize the team, I would
have a lot of ideas, some some great, someterrible, and over time, because I became
(37:33):
better at hiring, the team would figure it out.
Like, the team learned how to, like, kind ofnot do certain things.
And during the hypomanic zone, one can bephenomenal at fundraising.
Right?
Because you've got the energy to do 10 pitchesa day.
And when you're in the pitch, you're a littledelusional and grandiose.
And for better or for worse, that is a way toget investment.
(37:55):
And we can look at some of the messianicfigures in the entrepreneurial community.
And many of those people have raised the mostcapital, and some of them end up in prison.
So that was how I got through the hypomanicphases, was using alcohol to self medicate,
because alcohol, as we know, is not an upper,feels like it, it's a downer.
(38:18):
So the only thing that would enable me tosleep, and avoid spiraling upwards into mania,
was I drank every night, I think, between, youknow, 2 and 10 alcoholic drinks every single
night, and I was out every single night.
I can count, Maybe I had dinner at home 10times during the 1st 5 years I was building
(38:39):
bonobos.
Or,
and this
is what happens when you're hypomanic for a 100days in a row falling into depression.
And that depression typically would lastbetween 6 weeks and 3 months.
So, you know, similar phases.
And then during those periods, I woulddisappear.
I would say I was taking meetings withinvestors, and I would go home and sleep
(38:59):
because I could barely stay awake.
At 11 AM, I was so, so catatonic that I was,like, I just have to sleep.
I can remember being in rental cars onfundraising trips, and just tipping back the
chair and sleeping because I didn't feel awakeenough to drive.
Luckily, during depressive episodes, I didn'tdrink because I had no motivation to go out.
(39:21):
But it was bad.
I mean, I can remember getting home from workon a Friday at 5 and sleeping till Saturday at
5, and only waking up to eat cereal.
So I did I did sometimes cook cereal at home.
And then I would go out sometimes if I couldsummon the energy, and people would say, like,
hey, how are you doing?
What'd you do today?
And I was, like, oh, I slept in.
(39:41):
And it was, like, oh, me too.
I I didn't know how to say, like, I slept 24hours, which is obviously very abnormal.
So it was around that time of starting to ridethe roller coaster that both enabled me to do
herculean things like fundraising again andagain, but then crashing in a hard way that was
(40:03):
also extremely unhealthy.
I have this belief that, like, you learn themost when you're losing.
Like, when you didn't get that job you wantedor your business all almost went bankrupt or
maybe you get broken up with, your mind will gointo one of 2 states.
1 is, well, woe is me.
Or 2, like, I have to go figure this out.
(40:24):
And if you go into that state of, hey, I haveto figure this out, that's where a lot of the
growth is because you kinda have to experimentand figure out how to get out of that.
Let's fast forward a few years.
So you ended up selling to Walmart for about$300,000,000.
How did you come across Walmart and what wasthe story and connection there?
The Walmart thing was kind of amazing in termsof the serendipity of it because we were
(40:48):
running a process.
I did 75 pitches, something like that.
We got one term sheet out of 75 pitches.
We converted that one term sheet into a secondterm sheet.
So getting back to winning, we we had a we losta lot, but, ultimately, we won on the process
of having, like, a strong offer.
(41:09):
And the the private equity fund that made theoffer was getting in their own way a little bit
by wanting their capital to sit above everyonewho'd been there.
So they wanted to be senior, you know, theterminology, I think, you know, senior in the
preference stack above everyone else.
And it was like, well, you just got here.
(41:30):
Why are you senior?
And it was, this is how we do business.
And that led to our inside investors saying,We'll fund it.
So we had 2 options on the table.
1 was this minority investment, but a big one,call it a 150,000,000 from a private equity
fund, growth equity fund.
The other one was to take 10 or 15,000,000 ofinside capital from one of our board members
(41:51):
that wanted to put that in.
At this point, the company was really close tobreak even.
Or exit to a strategic, and we talked to a lotof strategics and none of them wanted to pay at
that point where the private equity company hadpriced the company, which was 300,000,000.
A lot of people wanted to pay a 100, but no onewanted to pay 300, and obviously, since we had
(42:12):
a $300,000,000 offer on the table that was moreor less in the interest of shareholders and for
all of us what we were gonna do.
So I get a phone call one day from a guy namedPreston.
Preston and I went to business school together.
He at the time was working for a company calledJet.
Jet was built by an entrepreneur named MarkLawrie.
Mark Laurrie had sold Jet to Walmart, andWalmart was now in this process of digital
(42:38):
transformation trying to compete, really forthe first time, compete in a big way with
Amazon.
So Preston and I are on the phone.
He calls me for a reference on someone.
I can't even remember who.
And we did the reference, and then I said, howHe said, How are you?
And I remember this because I was on anairplane, and I wanted to tell him the truth,
but I didn't know if anyone will overhear me.
(43:00):
And then I remembered an important thing I'velearned in life, which is, like, nobody cares.
Nobody was paying attention to my phone call.
And I said, honestly, I'm not great.
And Preston said, oh, what's going on?
I said, look, I'm running this process to, youknow, between us, sell the company, And I can't
figure out what to do.
There's one big offer that I don't think isgreat for our shareholders, but I think it's
(43:22):
time for us to get a lot of liquidity.
And then one of our insiders wants to putenough money put in money themselves, and I I
don't know if I can do that do this for another5 years.
In the context here was I've been through alot.
You know, I had just gone through psychosis andhospitalization and 6 months of depression, and
we were approaching our 10 year anniversary.
(43:44):
It was very hard for me to think about raisinginside capital and re upping for another 5
years.
I was burned out, and we had been through myfamily, my then girlfriend and future wife
included, hell for the previous year.
I didn't tell him about all that, I told him Iwasn't doing great in the process.
And he goes, why don't you talk to us?
And I was like, Walmart?
(44:05):
What?
They weren't even on the list that ourinvestment banker had put together of
strategics.
And I talked to 20 strategics.
Right?
We tried to talk we talked to Amazon and Gapand, you know, we tried to talk to Ralph Lauren
and maybe Brooks Brothers and all theseportfolio of apparel brands, VF, Core, PVH.
We talked to everyone.
Walmart wasn't on the list, which is sort ofinteresting because it's the largest apparel
(44:28):
retailer in the country.
And maybe Macy's is now, but maybe not.
It's it's big.
And Preston said, yeah, we're doing cool stuff,you know, in digital.
Let's talk.
And we had a meeting at Bonobos during theprocess, during the Bonobos process, and it was
Preston and one other entrepreneur named Katinaand one of the members of Mark's leadership
(44:52):
teams over time, both at Quincy, which is theowner of was the owner of diapers and soap and
wag.com, which was Mark's previous company.
He had a he was a senior executive at Jet, andI told him the story of Bonobos and they said,
oh, you should meet Mark.
This is interesting.
And that surprised me a lot.
And then I also started to think about, well,maybe Jet and Bonobos are aligned because Jet
(45:15):
was trying to make a more premium e commerceexperience, and now Walmart owns Jet.
So while I didn't see a future where Bonobosapparel would be sold at Walmart or through
walmart.com, I could picture it with Jet.
And I also was learning about all these cool,crazy initiatives that were happening under
Mark's leadership and entrepreneurs like JennyFleiss, who were joining the team to run, you
(45:37):
know, big moonshot projects like Jet Black,which was all about how do we use AI then,
conversational commerce and AI to disruptshopping.
Super cool stuff.
So they said, you gotta meet Mark.
So I said, okay.
Let's meet Mark.
I knew Mark.
I loved Mark Lawrie.
I'd only met with him twice in the previousdecade, and both times I loved it.
(45:58):
I learned so much.
So I was like, I'd love to see Mark.
So then the our process is dragging on and on,and the meeting with Mark is scheduled for,
like, 3 weeks later.
I'm like, this isn't the best m and a courtshipever.
Like, 3 weeks, I'm trying to figure out whatwe're gonna do.
So I had to wait.
And then the day of the meeting, I was like, Idon't wanna go.
(46:21):
I just want to do this growth equity deal.
I got comfortable with it.
I spent a lot of the time with the partners ofthat fund.
I really came to like them, and I started topicture myself working for them.
And I thought, you know what?
Let's re up.
I got my brain around what we had to do, whichis something that over time in life I've
learned to do, which is if life is handing yousomething, learn to wrap your brain around an
(46:43):
optimistic narrative about it.
So I I said to my assistant that day, I waslike, I don't think I wanna go.
Are there other important things going on todaywhere I can kinda justify canceling?
And she was like, now you got, like, 6 hoursfree in the middle of the day, which never
happened.
You know, this was sort of a whatever, 600person company, we'd raise over a 100,000,000
of capital.
(47:03):
There was always a back to back calendar.
So I went over to Hoboken to Mark's office, andI walk in and he's wearing, I can remember it,
a green check Vineyard Vines shirt.
And I was like, really, Mark?
We're gonna talk about bonobos and, you know,Jet and Walmart, and you're wearing one of our
biggest competitor shirts?
I was like, I didn't walk in here in an Amazont shirt.
(47:25):
And we laughed.
Right?
Because we had that basis of friendship.
Even though we hadn't seen each other a lot,there was an affinity there.
And then I said to him, I think what you justdid is sold a company for $3,000,000,000 16
months after launching it to maybe one of theonly 2 acquirers in the world that could afford
it.
And he was really humble about it.
He was like, yeah, we got, you know, this hasbeen really good.
(47:48):
So the headline there is I admired him so much.
And we sat down, you know, at a a circulartable like this.
What if we built a portfolio of 25 brands thatno one else that Amazon didn't have?
And that started to be a part of the kind offishing rod hook on why people would shop at
Jet and at Walmart instead of at Amazon.
(48:08):
And we dreamed big.
We were like, what if we bought Lego?
What if we bought Old Navy?
Because Walmart has the capital to do that.
Right?
When one when I was at Walmart, they boughtFlipkart in India for 16,000,000,000.
So that was really what happened.
I'm admired Mark.
We mind melded on the strategy.
He got there on matching the price of theprivate equity deal, and then the final step.
(48:31):
He's like he's like, you gotta meet Doug.
And I was like, who's Doug?
He's like, Doug is the CEO, let's get dinner.
And so we sat down at a restaurant in SoHo 1night as a trio, and I met Doug.
And I tried to grill Doug on all the thingsthat I thought my millennial employees from
Brooklyn would wanna know if it was announcedthat we got acquired by Walmart.
(48:51):
Hey, what's going on with your policy and guns?
What about wages?
What about not being unionized?
What about destroying main street?
All these kind of negative brand associations Ihad with Walmart as an New York City elitist,
basically.
Even though I grew grew up going to Walmart, myIndian immigrant mom would take us to Walmart
to get medication, to, develop photos Right.
(49:13):
To buy Cheerios.
So I had strayed from those roots, and Dougbrought me back.
And I basically professionally fell in lovewith Doug in that meeting.
I I was like, I love this guy, and I wouldfollow him into the fire.
And I already had great affinity for Mark.
So that dinner, I changed from being skepticalof doing the deal with Walmart to being, like,
(49:34):
I would be lucky to be at this table.
I would be lucky to be at this conversation,and those ingredients together led to why we
started to really hope we would do the dealwith Walmart, which is eventually where we
ended up.
How did it feel when you sold for 100 of1,000,000,000 of dollars?
I it was a relief.
I remember wondering if the deal would close.
It was a 6 month process.
(49:56):
There were 5 times like any deal you hear aboutwhere it could have died.
And I just didn't know if it was gonna happeneven after we'd signed a letter of intent.
And I remember thinking, I've gotta go toBentonville and get to know these folks so that
people on the executive team are rooting forthe deal.
Because Doug had told me that often when anacquisition happened, the board and Doug might
(50:18):
have been the only people that believed in it,and the executive team might not have.
Comes back to that concept of disrupting thecore business.
So I was like, I gotta meet all his directreports.
And I had a day and they were so awesome.
They just set me up in Mark's office in theexecutive Suite.
We are under l o I and I met everyone and metDan Bartlett, who was the head of Comms, and I
met Jackie Kenny, who was the CHRO, and I metBrett Biggs, who was the then CFO.
(50:42):
And I just wanted to meet them and talk aboutwhy I was excited, and also ask questions to
them about what they cared about, so that therewas a human enthusiasm for consummating the
deal.
And then I remember sitting down with LoriFleece, who was the then head of corporate
development and strategy.
(51:03):
And I said, Lori, what are the chances thisdeal closes?
And she goes, 5050.
And I was terrified because we had said no tothe private equity fund.
And I just couldn't believe it was 5050, eventhough we were under an LOI.
And I went to dinner with Mark that night.
Couldn't have been more stressed at a littleMexican restaurant off the Bentonville Square.
And I said, hey, I'm freaking out.
(51:25):
He said, why?
I said, I talked to Lori today, and she saidit's a 5050 chance that this closes.
And he was like, oh, yeah.
She said the same thing to me.
So it was scary.
I had to disclose my bipolar diagnosis duringthe process, and then I'd been arrested.
That was a very good reason the deal might nothave gone through.
And that plus a bunch of other business pointsmade me think this might not happen.
(51:50):
And so I got an email from Doug.
It was about a month away from the close.
I had been telling people, I hope we can closebefore my wedding, which is a very selfish
thing to say.
Those are, can we close by May?
And Doug wrote me an email 2 days before mywedding.
And he said, Andy, it's been great getting toknow you, and I look forward to meeting
Manuela.
(52:10):
And I felt like the CEO of the Fortune 1company by revenues wouldn't send that email
unless the deal was gonna close.
And I just started crying cause it's, it hadbeen a long road.
Man, could even get choked up now.
It had been a long road.
And I called my mom and I said, mom, Doug justcalled, you know, Doug just emailed me and I
think this is gonna happen.
And I was crying and, you know, I'm not a hugecrier, especially in front of my parents.
(52:35):
And my mom said, guess where I am?
I said, where?
She said, I'm at Walmart.
It was just super cool.
She was at the neighborhood Walmart around thecorner, which wasn't that improbable because
she goes to shop there.
But, you know, long winded way of saying it wassuch a relief.
And to wrap it up here, if I send you over aphone and you could call your 18 year old self,
(52:57):
would you call?
And if so, what would you say?
I would definitely call, and I would say getmarried earlier.
I would say, I know you're gonna get marriedin, 19 years, and get married earlier than
that.
Because having a partner is so grounding.
Because having having Manuela has changed mylife.
I learned to tell the truth quickly.
(53:20):
I learned to forgive myself for this thing thatI felt so shameful about for so long, which was
having bipolar.
She accepted that.
And we could go down a list of 10 other things.
And I think having someone who you love, whoalso holds you accountable, where you have an
honest communication relationship, and whereGod willing, and if you're interested, you can
(53:43):
build a family is a really wonderful thing.
And even professionally for an entrepreneur, Ithink it's good to be married.
And I remember having an executive coach oneday who sat down with me, and he was like, I
think you should find a partner.
I was like, oh, a new business partner.
He was like, no romantic partner.
And I was like, what?
And he said something interesting.
He said the whole company settles down when theCEO is married.
(54:07):
And it was such a fascinating conversation.
I'd never thought about it.
And then I got very excited about the girl whoI dated before Manuela, and it wasn't going
well.
And I actually had him meet her at some point.
And I was like, hey, it's not going well.
We're gonna break up.
What do I do?
Like, you told me to have a partner.
He's like, I didn't mean anyone.
It might not be this person.
(54:28):
And so I just wish, you know, I wish that I hadhad that insight earlier in my life.
And, you know, it just would have been I don'tknow.
It sounds selfish to say it just would havebeen helpful to my journey to be partnered up
earlier.
Yeah.
I think that's one of the things that I'veactually heard a lot about from successful
entrepreneurs later in their career is thatthey said having the right partner has been a
(54:50):
huge level up.
Like, I heard this from Ankur Jain who foundedBILT rewards.
They're now, like, a multibillion dollarcompany.
He's, like, yeah, marrying the right person,which in that case was Erica, was, like, a huge
up level for my life.
So I think it's really important, and I thinkthat's a great way to end it.
So first off, thanks, Andy, for taking the timeto join the show.
We'll have a link to Andy's latest business piein the episode description down below.
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Go check it out, and thanks for joining.
Thank you so much.
This has been awesome.
Awesome.