The Skinny Confidential Him & Her Podcast - Courtney Reum On Learning To Invest, Create Life Systems, & The Common Denominators To Find Success In Life & Business
Episode Date: November 13, 2023#626: Today, we're sitting down with Courtney Reum. Courtney is the Co-founder and Managing Partner of M13. He and his brother Carter founded M13 in 2016, and today the firm manages three top decile f...unds with more than $1 billion AUM in early-stage technology that powers the future of work, health, commerce, and money. Courtney joins us today to talk about all things entrepreneurship, investing, and how to grow as both a business owner and investor. He also gives us tips on what makes a great company and the common denominators of successful business owners and investors. To connect with Courtney Reum click HERE To connect with Lauryn Evarts Bosstick click HERE To connect with Michael Bosstick click HERE Read More on The Skinny Confidential HERE To subscribe to our YouTube Page click HERE For Detailed Show Notes visit TSCPODCAST.COM To Call the Him & Her Hotline call: 1-833-SKINNYS (754-6697) This episode is brought to you by The Skinny Confidential This episode is brought to you by Fable Pets Fable Pets designs gear that solves problems for you and your pet, so the two of you can enjoy exploring the world together. Go to fablepets.com/skinny for 20% off sitewide and 35% off sets. This episode is brought to you by AG1 If you want to take ownership of your health, it starts with AG1. Go to drinkAG1.com/SKINNY to get a free 1-year supply of Vitamin D3K2 AND 5 free AG1 Travel Packs with your first purchase. This episode is brought to you by L'Oreal Discover the new Bright Reveal Dark Spot Duo! Visit Target online and in-store to buy yours today. This episode is brought to you by Hiya Health Hiya Health fill in the most common gaps in modern children's diet to provide full-body nourishment our kids need with a yummy taste they love. Go to hiyahealth.com/skinny to receive 50% off your first order. This episode is brought to you by Wella Wella Professionals just released its most luxurious hair care line; Ultimate Repair. You can purchase The Ultimate Repair Miracle Hair Rescue at Ulta stores, or go to wella.com to learn more. This episode is brought to you by WeightWatchers WeightWatchers is the #1 doctor recommended weight-management program and the trusted authority in evidence based weight-health. Visit ww.com/tsc to see if you qualify, and if you do, used code TSC25 to get one free month plus $25 off your second month Produced by Dear Media
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The following podcast is a Dear Media production. So you can go online at Nordstrom's. You can pick up everything you need from the Skinny Confidential for gifts, for holiday, for yourself. Or you can go in stores and actually shop the
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So go shop all 93 Nordstrom locations or online at nordstroms.com and you can search
the Skinny Confidential. She's a lifestyle blogger extraordinaire. Fantastic. And he's a
serial entrepreneur. A very smart cookie. And now Lauren Everts and Michael Bostic are bringing you
along for the ride. Get ready for some major realness. Welcome to the skinny confidential, him and her.
One of my favorite quotes from our book is,
the best entrepreneurs have a microscope in one eye and a telescope in the other eye.
And you get the microscope in both eyes and you forget about the telescope.
And it's kind of like the little wave coming behind you.
And then there's this tidal wave that wipes you out.
Because if you're in an industry where Procter & Gamble and Consumer or Amazon can compete with
you, I mean, that is the tidal wave. They see something they like, they throw 100x the money
at it. And even if they don't do it nearly as well, could be out of business the next day.
Welcome back, everybody. Welcome to the Skinny Confidential Him and Her Show. Today,
we have a hell of an episode for you with our friend, Courtney Rehm. For those of you who are unfamiliar with who Courtney is, Courtney is the co-founder
and managing partner of M13. And today, the fund has over a billion under management.
To give you an idea of some of the early investments that Courtney and M13 identified,
they're in ClassPass, they're in Ring, they're in Coinbase, which she talks about, they're in
Ampla, Canvas, many businesses that have gone on to do incredible things. And this conversation doesn't have just information for
investors. Courtney joins us today to talk about all things entrepreneurship, investing, how to
grow as both a business owner and an investor, how to grow as a person. He also gives us tips
on what makes a great company and the common denominators for successful people, owner,
and investors. I guarantee in this episode,
there is something that anyone listening can apply to their own life. Like I said,
we talk on so many different things on how to be successful, how we started, what confidence looks
like, how to use your weaknesses to your advantage, how to grow a company sustainably, what not to do
when starting a company, the importance of persistence, and so much more. We could have
gone on and on with Courtney. She was a phenomenal guest and a total fountain of knowledge. Courtney, come back anytime. With that, Courtney Ream,
welcome to the Skinny Confidential, him and her show. This is the Skinny Confidential, him and her.
So Courtney, one of the best things about that I've discovered doing this show is we get to,
like, it's really strange how we get connected with people. In a former life, I would have somehow tried to cold pitch you and got in front of M13.
But what happens is I have someone like Brooke Burke on the show who has nothing to do with
any of this.
And she connects us over text.
And I always find it interesting when people ask about doing podcasts.
I say, listen, it's like the best hack to meet and network with people.
And it's different than going to you know
someone like yourself as a haley pick your brain over coffee or let me get a
dinner but if I say hey come on and talk about whatever you want to talk about
for an hour and a half it's an easy it's an easy yes so what do you want to talk
about and instead the punchline is I kind of like cold-pitched you yeah
through a friend but it's a real hack yeah exactly I got you to cold-pitch me
exactly I want to talk about all of it. I want to talk, we can talk about business pleasure.
We can talk about the state of the tech world, you know, what we're doing to optimize that all
of ourselves, anything. What were you like as a little boy? I'm the oldest. So I think I was,
was, and still I'm kind of the protector. I think my dad used to always say when Courtney's really
into something, watch out. When Courtney's not into something, watch out. When Courtney's not
into something, watch out. But in a bad way, you know, if I wasn't into something, I was just kind
of piano lessons fall by the wayside. Took like five years of lessons, couldn't even play anything
now. But for the things I was kind of passionate about, I was usually pretty, pretty immersive.
What were those things?
Sports were kind of the first ones. Although, you know, even my best sports, which ended up being soccer, which I played in college and almost kind of gave it a world to play after. I didn't even start playing until like about nine, which was which would be really late for for now. But sports once I found it. But I always just love kind of being like outside in nature, running around. I mean, what your brother and you have built is incredible. I just am fascinated by
the way your parents raised both of you. And we were just talking off air about
Paige and Blake of Aviator Nation and Tom's Shoes, that same thing there. I'm just so fascinated with
how their parents raised them too, because you guys are both so incredibly successful. When you
look back at your childhood, is there something that you can pinpoint now
that you think your parents did really right?
Well, let me also just say, as I said off air,
Blake is a really old friend of mine.
I know Paige.
And I've spent a lot of time with Blake's parents.
There's only a couple of people that remind me of my mom
more than Blake's mom.
So you are a soothsayer.
I need to get some tips.
There's a reason why they say this about you.
I need to get some tips for my kids a reason why they say this about you. I need to get some tips for my kids.
We ask these people.
We say, what the hell is a breakfast cereal?
You know, my parents are just, they're both Midwesterners through and through.
Just super principled people.
Stuff that my dad used to do that I tell myself I'd never do, I now do.
Like, he's very much about value.
So I'm the person that could spend seemingly an exorbitant amount of money, not think twice.
And then I'm arguing about $7 because it clearly wasn't $7 of value. And it's things now that seem
differently as you're older, but they were not environmentalists the way we call environmentalists
now, but they were really big
on turn off the lights when you leave the house, don't stand there with the refrigerator door open,
just kind of a lot of those things of what affects one directly affects everyone else indirectly.
And so my grandparents and beyond were all very rich in terms of education and creating
opportunity and maybe not money so much, but just incredible people and all did
really unique things. I had a governor of Michigan in my family,
Tree, the first private practice in Michigan, the first female congresswoman in Illinois. And so
I say that all because they were just very principled people. And I had this
amazing upbringing where I grew up in a town mostly outside Chicago, 900 people
on a dirt road.
Couldn't see my closest neighbor, but you go 10 minutes, you're at the time, second
or third biggest mall in Illinois.
10 more minutes, you're at a city that was the second biggest city in Illinois outside
Chicago.
15 more minutes and you're in downtown Chicago.
So I had this great mix of kind of like country and city.
And I think that along with just incredible parents was a was a big part of it
i want to talk about your dad a little bit because i know listen people have close relationships but
it seems like you had an extremely close relationship with your dad and i'm sorry to
hear about his passing obviously what are some of the things that you look back on that he taught
you that you have applied to your career in your life? Because it seems like it was an incredibly close relationship. Yeah. I know you guys are going to make me cry this early, but
he's just one of those people that real strong leader, real, like real patriarch in the, in the
truest sense, but in a way that until he was gone, you didn't realize like, you know, all the other
things he kind of did. I just had a great, he, he did everything
to make sure we had every opportunity, you know, and, and we didn't start out very wealthy,
although by the, by the time he passed away, he had, he had done really well, but that's,
you know, over 30, 40 year period. So it's, it's not where you start, it's where you end, but just,
just like a person of incredible integrity and a real family man. You know, when I, I'm sure you guys
are seeing with your own kids now, I mean, sports games in high school, I went to like a Chicago
public school. Parents would say above average, but I'll say a little bit above average Chicago
public school sports game started three, four o'clock. Didn't miss a single one. I mean,
it's just now that I see who did stuff like that and ran a large company, just
incredible, but never talked about it, never made a big deal. I could tell you so many stories,
but here's one that kind of symbolizes my dad. Through a weird convergence of factors,
a company that he worked for became a corporate sponsor of the Bulls in 1984.
Worst team in the league. A funny thing happened
in 1985. They drafted Michael Jordan. The rest is kind of history, but it took a bunch of years.
So this marketing partnership, he was working for an industrials company. This is pre-internet. So
people would see a banner that says McDonald's or go to Payless Shoes at the time when they saw
this company called Interlake. Nobody would know what it is and no one had a way to look it up.
But they got these four courtside tickets to the Bulls.
So I got to, so that company got sold.
My dad somehow managed to take the courtside tickets with him.
And so then he controlled them as opposed to the company.
And we've got to go to like every Bulls final
with Michael Jordan, but there's four seats,
five people in my family.
My dad would take us to the,
and my dad played college basketball and
almost played in the nba until he had an injury but all-state basketball player favorite sport
by a long shot he for some of the biggest games would drive us to the stadium chicago stadium's
not in a very nice neighborhood drop us off go sit in the car with the car running doors locked
read newspapers for three hours and come pick us up. That's the kind of person my dad was. If you don't do that for me and my kids, I don't want you.
You know, because listen, we're going to talk about a lot of the business success and all of
that. But I think I've met a lot of successful people doing the show and then known successful
people as well. And I always think it's a tragedy when their biggest accolade is the business stuff. And I think now that I'm a new father, the goal over time, when I'm gone, is to have
my children talk about me the same way.
I think a lot of people don't have that relationship.
And I think they lose sight sometimes over what's really important, if that makes sense.
Yeah.
And I think we could have a whole podcast, I'm sure, on a term like self-made.
When people are like, are you self-made?
I'm like, no. But not to discredit anyone, but I think almost nobody is self-made
in the sense that you've had influences and for sure people have come from more adverse
circumstances than I have, but they somehow had someone or some things, or even a role model of
like negative role modeling that helped them, you know, become who they are. And so there's levels
to it. But I think like,
even people who didn't come from money, they, you are not self-made if you came from a family
rich in values and character and love and all that other stuff. Yeah. When you look back now,
are there certain moments in time that you could tell when you were little that you were going to
be an investor? Like, are there little things that you did that have led up to this when you were young or a teenager?
Well, I consider myself very much kind of an entrepreneur and investor. We've started a bunch
of things as well. And so I think being able to empathize with that entrepreneurial journey kind
of has made me a better investor. But I think I'm someone that was just always interested in
how things worked. And when I grew up, it was like,
what do you want to be? Like one thing, period. And I remember actually, you know, I went to
Columbia uptown here. The college counselor senior year was like, the average person graduating your
year is going to have 10 different jobs and five different careers, however they define that. And
it must be double that now for people graduating. But I was like, oh, wow, that sounds great because
I love the diversity. I love kind of working on multiple things and multiple projects. So I think that's
a big part of investing or starting things is being able to handle that and being curious how
things work. What was your first entrepreneurial journey? What was the first thing you did?
It's a story for over a drink, pun intended. But my brother and i um both both went to columbia both worked at goldman
sacks doing investment banking and then we left to be entrepreneurs which doesn't sound so crazy
but in 2007 only people that i that i knew working at goldman who left to do something other than
hedge fund or private equity we kind of had this idea of creating a better way to drink
we were at the time you know working hours, but still trying to be healthy. And then we're just ravaging our bodies,
drinking Red Bull vodkas, Grey Goose sodas, you name it. And we said, let's try and create a
better way to drink as a product in the bottle and as a company. So we created the first,
we'll call it kind of a sustainable and organic vodka alternative called Vive. I remember that very well. The bottle was
so, is so beautiful. It was like a matte, like almost crystal. Kind of like a matte frost.
Matte frost. Like everyone does their cars in these wraps now, but it was like a matte frost.
It was so chic and it did make drinking feel healthy, which is exactly what you set out to do. That's so crazy. So what did that journey with that look like? Well, I mean, it started the smallest of the
small. If there's ever an industry where you talk about legacy or, oh, I have a friend in it or my
dad or mom's in it or whatever the case may be, there are not many people that go into spirits
without having some hookup or preconceived notion. We just had like Google and some hustle. So we started it from scratch. We didn't know any
distributors, didn't know where to find one. And by law, alcohol has something that goes back to
prohibition called the three-tier system. And so you have to work through a distributor. You can't
direct sell the way you can, I don't know, other product, snack products or non-alcoholic beverage.
So we self-distributed at the back of a Prius in Los
Angeles, went door-to-door guerrilla warfare to all the coolest accounts at the time. This is
even predating a Soho house, but clubs that don't exist anymore. And eventually got it into a lot
of them and opened one state because you literally have to open state by state and you name it.
Within three years, we got national distribution. We had fun partnerships. We were the official cocktail of Virgin American Airlines. We were
Disney's best-selling cocktail. Eventually got to about a million bottles a year before we exited.
But even to this day, 15 years later, there is no industry that I think is harder because there's
so little tech. There's so much regulation. I knew where every bottle was buried just about,
so to speak, which is both rewarding and a lot of work.
You know what's a hard industry?
Sex.
Michael and I are both just like, don't say anything.
My friend has a sex company, and it's a hard industry like alcohol.
It's what you're saying.
There's so much regulation around how you can post it online.
Yeah, we have a company we incubated with Procter & Gamble around menopause called Kindra.
And this is menopause, not even sex. I couldn't tell you the specifics, but I know that they've
been really frustrating because their advertising habitually gets taken down. We were talking about
menopause, not vaginal dryness, but to help people, not anything sexual.
I mean, it's important though to have these conversations because if people are trying to start businesses they should know that those two industries are
difficult how i wanted to know exactly how long it took you and your brother to sell the company
i'll call it about seven and a half eight years of just a lot of work grind and six days you know
seven days a week of work and six,
I used to drink six days a week. Like just cause I'm a really competitive person. I used to like,
it logically doesn't make sense, but I would think that my liver could make this successful.
Not to mention if I went out and, you know, having a meeting or you're hopping around to a couple
accounts, which I love to do, I'm going to go, there's the Viva. I have a shot with me. Yeah.
You can't say no. I mean, that's like, you know, Santa Claus saying you're not getting a present this year.
So I had a drink with Evelyn.
And next thing you know, I was averaging, you know, half dozen drinks a night.
How do you wake up and be so successful in the morning?
I'm such a pussy with hangovers.
Doing it now, now three drinks and I'm basically like that.
But yeah, I'll never forget when I went to get a physical for the first time in 10 years,
the guys, you know, going down the list.
Do you smoke?
Do you do whatever? Do you drink? And he's not even looking 10 years, the guys going down the list, do you smoke? Do you do whatever?
Do you drink?
And he's not even looking up.
He's just marking the things.
And do you drink?
Yes.
How much per week?
30 drinks a week.
He's like, what?
Actually, more like 40.
He's like, just takes his glasses, lifts them off his head.
And he goes, son, we've got to talk.
And I was like, no, no, no.
I can explain.
He goes, I bet you can.
I was like, no, really?
Oh my God.
You know, because he just thought I was an alcoholic.
And it was
just because you were tasting all the drinks on the job. Yeah, for sure. Like the time early on,
I got pulled over and the cop pulls me over and says, is there anything in the car that I should
know about? I was like, absolutely not. I was like, oh, actually there's 50 cases of alcohol
in the back, but I can explain that because we were self-distributing. So I was taken into an
event. I had like 300 bottles of alcohol. Did he get mad? It's not illegal, but he wanted to be really sure that I was actually taking that to an event as
opposed to driving to Tijuana. I have a question around, so you've obviously, you've been an
entrepreneur, you are an entrepreneur, you've been an investor. There's a lot of young people
that listen to this show that are thinking about starting a business. When you guys are,
and maybe there's some experience as well, when you're speaking to founders
or potential founders,
what are the character traits
that you're looking for?
Not even the ideas,
but just the traits you're looking for
in the individual.
Does Michael Bostic check the boxes?
Let's hear it.
He's very handsome.
So yes, I mean, already,
you know, it's just a handsome.
Handsome, handsome.
So you're going straight looks.
He has a great hairline.
Yeah, exactly.
Straight looks.
He exudes confidence. I think, you know know i'm sure lots of people have been on here and given lots of
adjectives i would say it starts with you i do want the person who's like relentless within reason
you know because the the good founders start off here and then they have the proverbial pivot or
whatever the idea the somehow the best founders always find a way to make lemonade from lemons.
It might not be the exact lemonade you thought you were going to make or as big a batch of
lemonade, so to speak, but they always do something or they keep it alive.
And sometimes this is a game of ping pong where you just keep the ball on the court
for another day and then something good happens.
So I think that counts for a lot because I've also seen what I consider, what I thought were good founders and what I thought
were really good ideas fail because the founder just couldn't will it to like the next bridge
or the next milestone. So that's really important. But I also think if you would ask me this question
10 years ago, I probably would have given a little more of that mold of like
the Travis from Uber. And now I think it's much more important
to almost be like on a good day, how I perceive the president of the United States. Of course,
you can't know everything that's going on. Of course, everyone has blind spots. There's only
24 hours in a day. So it's more important to be hyper high EQ and self-aware and go, well,
I'm good at this, but I know I'm not good at this. So I need to fill in these blind spots.
And I know I need to have this team around me because no man or woman's an island and no successful company does it on their own now.
So I think that's probably the biggest trade I look for is the rest of the team and the
self-awareness of that. What's something that you and your brother roll your eyes at when someone
leaves the room and you're like, fuck, they did that thing. Like what's something that people do
that like a lot of people do that's like a red flag that you're just like, oh, like when they're
like pitching or something. Yeah. That's so common that you're like, oh my God,
90% of people do this. It's, it's, it's not even just in pitching, but just a red flag,
you know, trying to conduct business or just trying to get something done. Yeah. I think it's
when, you know, and I, I used to be someone who had a lot
of trouble showing vulnerability, showing weakness. I'm really competitive. I like to win.
If you like to win and you're used to winning, all you want to do is keep winning. So I think
it's the people who never, you know, when you ask like, well, what's not going well or what,
if this business isn't successful, what will have you gotten wrong? And you can tell they just give
you the canned answer. Like it's like in the interview, the weakness question, but you give a fake answer
that could also be- My weakness is perfection.
Yeah. I'm not a good listener. So I think it's those people who aren't being honest about where
the struggles are because smart investors usually hone right in and go, oh, okay, here are the key
things. Here are the couple questions.
Where are you at with this?
Versus maybe there's some dumb money out there,
but the smart money knows what's going on
and where the pressure points are.
So I think that,
and then just for a comical one in the world of AI,
we had someone come in a few months ago
and we said,
we always say at the end of our IC investment committee,
we always say, okay, what are you kind of raising? What what's around look like, what's your ideal
partner partner look like? And so we said, how much are you, how much are you looking to raise?
He said, well, I can't really say that because I, I, I'm just going to let the market decide if
we're an AI company or not. And thus how much we're going to raise, AKA, if someone's willing
to write, you know, value it like three times as much because they think you're an AI
company, we'll take like three times as much money. And so that answer was just such a turn
off because it kind of was a little insulting. It was a little bit like he has a new company
that barely has any data, which he doesn't even know how to use, but it was the start of that.
Oh, everything was an AI company. You know, I was going to, I think for Dear Media is the first
time I actually went and raised outside venture private equity capital.
Everything else I've ever done has either been friends and family or self-funded.
And I did it for a reason.
I think a lot of people have glamorized raising capital, as you know, and it's become like the benchmark.
It's not like, how's your company doing?
It's like, how much have you raised becomes the new badge of honor? And I think as we've seen, a lot of companies have struggled and a lot of
founders have gotten in trouble with that. Playing the devil's advocate, the other side,
when do you think it's appropriate for young founders who have an idea to seek out venture
capital or private equity? And when do you think it's, hey, maybe hold onto it a little longer and
do your own thing without that capital? Yeah. And we, I think, have a whole chapter about this in
the book we wrote. But I think it's changed a little bit. But in general, in this economy,
as long as you can go without taking it, great. I mean, because it must mean you're doing something,
right? It must mean you might not be profitable, period, but like unit economics profitable or
whatever it may be. So the longer you can do that, the better. It'll force you might not be profitable, period, but like unit economics profitable or whatever it may be.
So the longer you can do that, the better.
It'll force you to, you know, dig in, force you to not have the mindset of, why should I choose A or B?
I can do A and B, you know, and we kind of went through this bubble period of I can do this and that, not make tough tradeoffs and tough choices, which is any founder's job. So I think as long as you can go, the better. I do generally believe that once you kind of start taking the house's money,
AKA venture, you want to keep doing it to a point. I'm not saying how much, but I'm saying
at that point, you want to keep taking the money. But I also think we're just living in this new
era that will hopefully be a more permanent era of people just really trying to
figure out how to make sustainable businesses. Because having a billion dollars in revenue is
great, but if you're not making any money at a billion dollars in revenue, you might never be
meant to. I've been part of companies where we're like, wait, as it stands right now, every order
that we ship, we are going to lose more and more money because shipping costs
or whatever else. It's just the economics are getting worse the more we sell. Yeah. There was
a period of time. And I think like you see these huge exits. I was just reading something about
Dollar Shave and how like the enough times password, I guess they've, there's a Unilever,
they kind of classified it as not the greatest acquisition. And I, you know, I think that's a
technical term. Yeah, I think so. And I, you know so. And I think that was a phenomenal business.
And I know people that worked in that organization.
But I think people read the headlines, billion dollars.
And it was just billion dollars at the expense of profitability and efficiency.
And I think a lot of founders have glamorized that or also use that as a playbook.
That's the thing I have to build in order to get the exit.
I have to build this massive revenue beast that may not be so efficient, but that's the only way
I'm going to sell. Well, I'll give you a different spin on it, which is that, yeah, I mean, that's
public information sold for a billion dollars. I know Michael Dubin, some from LA, great guy,
love the kind of brand voice he had in doing that. But it's pretty crazy that someone would pay a
billion dollars for that. It got to about $200 million in revenue. Five times multiple isn't crazy. But what's crazier is if you start
knowing that that's the big company's appetite and they're going to do it based on something
like that, you're really incentivized to raise as much as you can, as fast as you can, grow it as
fast as you can, but in an unsustainable way. So the unit economics weren't actually that great.
But if you actually think what Unilever is thinking, they must be thinking this only works
if we can push a bunch of other products to this customer, right? They thought butt wipes was going
to be a huge thing. That's not a technical term, but that is literally what they thought. Products
like that were going to be a huge seller and they thought that customer was really sticky and it
turned out they weren't. And so there's been a bunch of other things like it, but I think you're actually incentivizing
clever people like Michael Dubin to create something, reverse engineer it to sell to
Unilever. And then it's kind of, he definitely won, which is great, but I know him. He's a great guy
and he cares about the legacy of something like that, just as I do of anything I've started.
And nobody wants to see the value of their company impaired, much less written off. And I've had companies I've sold that basically don't exist today
because next owner, but it's because they don't know how to make it work if it's not a going
concern. Yeah. And the reason I bring it up is not to comment anything on anybody's personality,
but I think a lot of young founders are seeing that model and they're thinking that's what I do.
And maybe you share this perspective that the market has just changed and I don't think those companies get
rewarded in the same kind of way. And so now all of a sudden you have this big machine that's just
killing cash all the time and there's not going to be that Unilever exit event. You know what I
mean? I think my brother and I's personal journey, again, M13 was kind of, we did a bunch of personal
investing and consumery stuff that kind of morphed into a bunch of personal investing and consumer-y stuff that
kind of morphed into direct-to-consumer, lots of fortuitous exits in those kinds of products that
you described. And then we've kind of moved more into tech for a lot of reasons. One, I think,
can make a bigger impact, bigger innovation at scale. But the second part is that I think it's
harder to spin up these kind of one-hit wonders. And it's the difference between having a product versus a company.
We want to be part of life-changing companies or platforms, not just a product.
And too many times it ends up kind of being a single product.
And to your point, there's just not a market for them anymore.
Investing does, at times, for a woman woman feel like a boys club. There's almost like an energy around
it that sometimes when I talk to investors, they try to make it more complex than it is
to sort of give it a superior complex. You and your brother have made it so digestible,
which is so amazing like you've really
like broken it down if someone's listening and they feel overwhelmed by a conversation about an
investment how would you dumb it down in simple terms it really depends on you know the product
and the industry but i think we're seeing now i mean as i said to my answer before i would put
eq over iq in most of these things.
I will make a sweeping generalization and say that most of the women that I've been lucky enough to
work for and with have had much higher EQs and brought a lot of those intangibles that now we're
seeing are much more tangible. So I would start by just saying, don't let anybody do it to you
in the sense that I try all the time to go, sorry, what did that mean that you just said? And they're like, wait, wait,
you didn't know what that meant? You're, you're so-and-so or you're, you're in this industry.
I'm like, just didn't know what it meant. Sorry. You're using a lot of jargon there,
chief. I went to Chicago public school. Just almost make them feel bad or not feel bad,
but just don't be intimidated to just slow it down because chances are, whatever they're talking
about, that's not the crux of it. The crux of it is something else. And they're just trying to kind of, you know,
use some flowery prose or some confusing things. And, you know, any woman who's in the process of
starting something probably understands what's at the core of what she's doing.
If someone is listening and they have an idea, you said that they don't need to take an investment
if they don't need to, but what if they want an investment? How would you advise them to go about it? Say it's a very simple idea and they want an
investor. What should they do? I think there's nothing, it's just human nature that you like
to feel desired or that someone took the time to find out who you are. So I think just finding out who would be your dream investor
or investors is a great start. And it's one thing just to reach out. It's another thing to reach out
and say, I think I wanted to chat with you because X, Y, and Z or something. I always respond to
emails that aren't cold emails or sorry, that are cold emails, but show some level of they know something about
me or about M13 and it's actually personalized, not the, you know, not the templatized ones.
How do people like out of control? It's out of control.
Well, now I was, I was with a friend of mine who's, who you guys would know is a very prominent
entrepreneur. And we were talking about how it went from like the cold spam emails that are so
hard. You know, it starts out, hey, long time no talk.
I'm like, do I know this person?
And they send you the whole thing.
And now they reply on top of it going,
hey, just making sure you saw this.
I'm like, wait, I didn't know you then,
I don't know you now.
And as my friend's showing me the cold email thing,
turns out that another friend of mine was cold emailing him.
I was like, oh yeah, anyways.
But it's crazy just, you know,
with AI or certain kind of tools.
I mean, you can just,
I know how many emails I'm getting a day.
Like imagine what Tim Cook's getting.
Yeah, you have to really do something that stands out.
I also think- Wait, can I just, sorry to interrupt.
I'll just say to your question,
this is what I joke, but it's really true.
We live in a world where it's not hard
to find Tim Cook's email.
I have Tim Cook's email.
It's hard to get Tim Cook to reply.
Now I've only tried like three times, but I'm 0 for 3.
But it's that it's hard to get Tim Cook to reply.
So give him a reason and something specific.
And I don't know that you can get Tim Cook to reply,
but you have a much better shot.
You know what Warren Buffett and Charlie Munger do?
They don't have email.
You have to hand write them a note in the mail
to get their attention to do
anything i went and tried the note doesn't guarantee and the note doesn't get obviously
the note you got to stand out in the note maybe i should drop like my thong underwear in there
that might get charlie's attention i have an idea that involves your thong underwear
with your permission so my first boss at gold Goldman who went on to start a really successful company,
he was the type, again, this was kind of on the fringe of email.
And he said, yeah, email, we're starting to get a lot of it, whatever.
He started a company that targeted like Fortune 100 CEOs.
And at the time, FedEx wasn't nearly as ubiquitous.
And people being humans and having all kinds of different tastes,
he said, I know, no matter who
you are, you almost always check your own FedEx. And at the time it was true, maybe not now.
So someone you want to get in touch with, just start sending them one FedEx a week with something
in it or a note or whatever. Finally, this guy calls them who you guys would all know and says,
okay, I got it. I've gotten 23 straight FedExes from you. What can I do? And he goes, oh, really?
Okay. I was just kind of getting warmed up,
but great, I'd love to chat.
So I think, think about that.
I don't know if Charlie and Warren
are a little immune to your thong at this point,
but I think the principle holds.
If your thong doesn't work, we'll send mine.
That could work.
We could send both and see what they prefer.
We'll see which one they prefer.
A little A-B test, yeah.
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What are some things that you see with founders that scale and end up running their company into
the ground? What are some things that they do wrong across the board?
It's always the very
simple stuff, not treating every dollar like it's your own. You know, as soon as I give you money,
it feels different, like you got some allowance that you're going to blow. As I said before,
I think it is very much an open source, crowdsource sort of world. So
almost unless you're in like deep cybersecurity or something, there's just not many trade secrets
out there, right? Like it's not that hard to rip off Coca-Cola even though it has its ingredient or
KFC secret sauce. So too many people kind of end up hoarding their idea and then are shocked when
all these people come along because they just didn't see it coming. Because you need that.
One of my favorite quotes from our book is, the best entrepreneurs have a microscope in one eye
and a telescope in the other eye. And you get the microscope in both eyes and you forget about the telescope.
And it's kind of like, there's like the little wave coming behind you. And then there's this
tidal wave that wipes you out, right? Because like, if you're in an industry where Procter
and Gamble and Consumer or Amazon can compete with you, I mean, that is the tidal wave. They
see something they like, they throw a hundred X the money at it. And even if they don't do it nearly as well,
you could be out of business the next day. What seems like to me the ideas that really work are
the ones where someone comes into a category that's already established and they do it better
than anyone else. That's kind of what I've seen, even like posting, when I post things like a swipe up or a link,
the products that people love are the products
that it's already an established category
and someone does it better, like floor mats.
That guy, the weather tech.
Yeah, I don't want to put him on blast, but yeah,
he killed it.
But no, I think some of the,
I think we're going to this road you mentioned,
like AI and there's all this technology and you can do things in such an efficient way now that I think sometimes people get lost in like the tools and the gadgets and the gizmos and they don't put nearly enough emphasis on like building a true brand.
You know what I mean?
It's like just all the stuff.
And, you know, we were talking, running Dear Medium, people were like, oh, how do you think AI is going to affect?
And I said, listen, it's a tool, but I think it's a mistake for people to think that it will replace human
interaction right or to your point a cold email with ai like people i think there's something
inherently in us as humans where like you need this kind of interaction and you can use the other
stuff but if you just slowly rely on that stuff i think that's going to carry your business or your
idea or your media whatever it is i think a lot of people are going to get in a lot of trouble. Yeah. I'm right there with you
on it. I think in the world of Zoom, I mean, we try to never hire anyone we haven't met and we've
scaled up pretty fast at M13. But as you guys know, full disclosure, I was a little late today,
which I'm sorry for. I had a meeting in deep Brooklyn. I had two meetings, but one of them
was with a new person we're going to have handle all of our travel.
And I just said, he's like, I've had people for 10 years and named off clients that are really well-known people.
I've never even met them.
I go, that's just not me.
And I know there's going to come a moment, probably not too distant future, where you're annoyed with me because I'm changing flights or I'm at an airport.
I'm calling you while you're observing this or that.
And I just want you to know, I just want to feel like I've met you and you're a decent person.
I'm a decent person.
And I think it'll just change the dynamic.
And when I came in today, it was just like, that means so much that you came to me.
And he lives in a really unique neighborhood.
And I think relationships will be at a premium no matter what with AI, maybe not driving your car.
But some relationship, especially one that gives off some kind of emotive feeling, will
be at a big premium.
When you work with your brother, what do you guys fight about?
Well, you know, when people usually ask what's like working with your brother,
I like to invoke the Charles Dickens tale of two cities, you know, the opening line,
twas the best of times, twas the worst of times. I'm sure you two can relate. When it's going
better, nothing better. When it's going worse, nothing worse. And I think figuring this out
has been easier than us figuring out how to parent
like figuring
working together
no not easier
harder
meaning like
figuring all of this
shit out
has probably been
more beneficial
to our marriage
than all the other stuff
because I feel like
this is so hard
as you know
there's so many
emotions
and you know
it's like a dance
who's leading
who's falling
it's different times
my favorite is when
he really annoys me
I go
I'm not gonna do
that work today
she literally goes on strike union strike Like a dance, who's leading, who's falling. My favorite is when he really annoys me. I go, I'm not going to do that work today.
She literally goes on strike.
Union strike.
You're unionizing.
This is not great relationship advice,
but I think some of the, I guess,
reason that we've had success in our marriage is I think we've had to figure out
a lot of this really hard shit.
And the marriage actually becomes
the easier place to figure.
So does it make sense?
Yeah.
They're not married though. That's different. Yeah. I'll come back to the married part in one second, but I'll say this. It's now been 15 years of partnering with my
brother. And as I said before that, we both went to the same schools and worked at the same place.
So imagine you go from a Goldman Sachs to being business partners in like not only three or four
different ventures, but three or four different types of ventures, alcohol, some kind of other stuff that we don't always talk about, but some different brands.
And then something like M13, it couldn't be more different. Luckily our skill sets have
translated, but I think, I think it's not about, it's more just like learning each other's hot
buttons and being careful when you pull the nuclear card, because it's, it's that when we
first started, we would read stories about these family businesses
that blew up or like wow can you believe like that would never happen to us and it never it never got
that close but it got closer than i ever thought it could get in the sense that you know our first
startup we had one car that we were sharing in la where you need a car we we bought our house that
was like a little bit or a lot of a stretch for us. So we worked
out of our house. We have employees coming. Like some days I'd wake up a little later because we're
doing whatever and employees are sitting at my kitchen counter working. It's a lot. Like I could
smell what he ate for lunch and that would annoy me on a given day and the whole thing. But I think
now over time, I think we both know that we're both kind of like to lead, both like to lead,
although in different ways.
We're both alpha enough and competitive enough that with M13,
I actually think it's that we both find different kind of lanes.
And although we partner on a lot of stuff,
we kind of do a lot of our own thing.
And then it's nice to actually come back and have a thought partner.
And then truthfully, the best thing is we also have
a lot of other incredible talented people at M13. So in our first companies, we were each other's sounding board and we were
the only ones to go to for X, Y, or Z, even if we weren't the most qualified. Now there's people
that are more qualified in a lot of different disciplines of what we do at M13. So it's great
because we just get more diversity of thought, but it's it's all those things and then you know as you
guys probably know my brother's now married to paris hilton so that's a whole nother dynamic
i watched paris in love so i know all about it did you see me make a couple cameos yes i saw
you make a couple cameos we have to go re-watch it now one of my questions for you is a big upset
because um i had officiated a couple of family weddings before that, five-star reviews and references available. Paris's family
really didn't want me to officiate the wedding. So I was in as few episodes as possible, but
there's one where at the bachelor party and we're rolling the craps dice, or no, sorry, roulette.
Paris's mom, Kathy, wanted to have a guy named Father Ed. So I'm throwing the ball around roulette.
And we're like, if it's red, Father Ed.
If it's red, Father Ed.
What was it?
Well, the magic of editing.
But let's say I didn't officiate the wedding.
She wasn't going down one way or another.
But you know, double zero all of a sudden.
I want to ask you what the best business advice that you received from Paris Hilton.
Because she is such a mogul with her business and the way she runs it.
It's so incredibly impressive.
Well, I think it's come out and we've had, we've talked about actually her specifically
on the show that people don't give her enough credit, especially in the influencer creator
space.
Like she was one of, if not the originals.
Yeah.
No, I mean, I might, if you really want to talk to Oliver Ackley is my brother is, is
no better hype man and husband than that.
But I think, yeah, you know, everything from obviously someone like Kim Kardashian,
who was Paris' friend long before she was Kim K, but she did the first selfie.
So I think in some ways social media wouldn't exist without Paris.
It's just been really great to watch her evolution as her now brother-in-law
because there are some people that are really stuck on their view of her from simple life and 21 years old.
And, you know, at least a good portion of that I think was kind of an act.
But now she's kind of matured into motherhood and being a real entrepreneur.
It's impressive to see and it's impressive because she just has that it thing, but not like, I'm not talking like walking a runway it,
but that it thing where I think her superpower
is that she really sees trends before other people.
And then it was really good to find out who to partner with.
You know, again, I'm sorry,
I don't have the stats exactly handy,
but she sold billions of dollars of her fragrance.
Now she didn't produce it herself,
but I mean, one of the more lucrative licensing deals
that I've ever heard of.
And she knew exactly who to go to and figured out a way to be ahead of the
curve on things like that, on things like social media. Do you and your brother give her business
advice? We do, I'd say in the sense that she's had, she kind of went to the school of hard knocks,
whatever you want to call it. Like she didn't go to like a Harvard or go to a Columbia or work at
Goldman Sachs. So those are the people, not just Paris, but I find really impressive who weren't
classically trained yet kind of seemingly know everything I know, but they've kind of done it,
done it, you know, through the, through the Braille method. It's, it's incredible. So
she's just got a lot of great business instincts. Sometimes we kind of give her a little more of
like the academic view of it, but my brother, truthfully, shout out to my brother
because he's done an incredible job of building her media holding company called 1111 Media
because it's really a model. But he really applied a lot of our principles for M13 and other things
my brother knew. But my brother's a real incredible strategic mind and a real incredible visionary. So
anyone who gets that much of my brother's time is I think going to have some good success.
I wanted to ask you a question
around school, undergrad specifically.
I, a little bit different than you,
went to the Harvard of the Desert,
which was the University of Arizona.
It was a little bit different.
Go Wildcats, yeah.
The University of Pussy.
A little different degree.
But Lauren and I both on this show
have sometimes been critical
about taking on debt and going through university if you don't have somebody to maybe help support.
And also from my perspective, not to knock Arizona that much, but I felt like I was really kind of more just learning to be independent, being social, having some fun.
I left and one thing I regret is like, man, I should have gone and gone into like computer sciences or finance or something more used. Like I was in like regional development. I thought I
was gonna be in real estate. It was anyways, I'm not applying any of it, but from your perspective,
I mean, you went to two extremely prestigious schools and it sounds like you had a phenomenal
education. How do you feel about those programs? And maybe they've changed a little bit now. And
like, do you think it's for everybody? Do you think people should pursue it?
Or are there certain people that should not pursue it?
Yeah, I mean, the short answer is no,
it's not for everyone, for sure.
And I think, no one says education's broken.
They're not wrong.
One of my, Seth Godin, who I'm sure you guys know,
the marketer, he loves to say like,
oh, you went to two famous schools. He said, I don't know if they're good. I didn't go there, but I hear people
say really good things, but I hear them say about other schools. I don't know if you, you went to
two really famous schools, maybe not two really good schools. And I think he's at least right to
a point. They were, they were good for me. They opened great doors for me. But you know, when I
went to Columbia, it was 30,000 a year. Now it's like, I think almost triple that. I mean, who can
afford that? Right. So I think, so I don't, I don't think it's for everyone. And, and, you know, I'm a big,
my parents were really big believers in education, but also really big believers in it's not,
it's not kind of like where you are, but what you're doing, because if you're in Arizona and
busting your, you know, what, or Arizona has a great business school and undergraduate business
school. I think there's a lot of differences in how things turn out. But it is one of my real, as I get older, fears for the future of, I'll say,
America specifically, because I was just in Cuba where their biggest export is education,
doctors and things, because they do free education through the government. We have too big a middle
layer here of people going to school because they're supposed to, but then they're going to
school and not making the most of it. It're not, it's not about, are you learning science applicable? But it's like, are you
learning? Like I was a philosophy major. I certainly think it taught me. I was one of my
majors, philosophy and economics. It taught me an analytical way of thinking that at least made me
put together frameworks for how I do like mental models now. And I just don't think people, and
yeah, I was in a fraternity and had fun, but I just don't think people are being pushed to do
that. And they're not graduating a 22 year old graduating here i can tell you feels very
different than a 22 year old graduating from a place in europe where it's just a different focus
yeah i guess the reason i ask is because and again not to knock the school but i just feel
like i didn't take anything out of that education that i outside of just being independent that i've
applied to anything i've since done in business and And a lot of what I had to figure out, like you said,
is like this Braille method where, you know, I'm on Google, I'm talking to different people,
or I'm just learning the hard way. And I go back and forth sometimes thinking like, man,
if I would have had that education, like what have I accelerated and missed some of those
like early mistakes or were the early mistakes, the things that have now set me up for greater
success. You know what I mean? Yeah. But it's, it's like, if it, if it looking back, if it hasn't
served you and you've kind of had to do it all yourself, I'm sure there's some lessons there,
but I, you know, I only went to business school cause I was sitting at Goldman and a woman walks
in the camera. She was from Bainer McKinsey. She was from a consulting firm and I was kind of on
the fence and she said, you know, the way I view it is if you're going to have a 40 year career and I could do something for two years, AKA business school,
that would enhance the other 38, wouldn't you do it? And I was like, that sure makes sense.
And one of my parents' big things was like, you don't have to know what you want to do, but like
keep your options open. I would hate to see you make a bad decision or series of bad decisions
at age 16 or age 18 that you would never get a chance to
recover from the rest of your life because you were down a certain track or these doors closed.
And so that's something I was really grateful for is optionality and option value.
Yeah. I think the one thing that we try to tell a lot of young people is to your point,
I can't believe how expensive some of these schools are now. And if someone's ambition is
like, hey, I want to go and be an influencer or I want to go and be a creator,
I want to start a podcast.
I'm like, well, maybe you don't need to take on
$90,000 a year in debt to do that.
I think like not enough people talk about
the purpose behind taking on that debt
or paying for that service.
And it's one of these things where I think
you're just, let's say, quote unquote,
you're supposed to do it
or you have to do it to have success.
And I think the times have just changed. And so for sure. I think my corollary, if I was
talking to my kids would be, okay, at 17 here, you think you want to be an influencer. And so
we forego college and now you don't want to be, or something happens. And all of a sudden you
might have fewer options and you might, might not, but I've, I've come to believe a lot of the most
interesting people I know had really alternative paths on education, might've even been homeschooled. And to your point, don't get me wrong, Columbia or Harvard
or whatever were really hard, but in some ways my like slightly above average Chicago public school
was really hard, not A to Z, but the top 20 people there are all fighting like heck to like get out
and make something themselves and do something better. And so that was really competitive among those 20 people out of 400 kids because everyone wanted that so it's just
different but it's it was the same kind of pressures out of all the companies that you've
invested in personally and with m13 which one has been the most successful and why? And maybe you could talk about exits too.
Hot water question.
I want to know which is the best one
where you're like, oh my God, this is amazing.
I guess not to be too pedantic,
but it depends how we define best.
My best personal...
What you think is best.
Well, so the one...
I'll give you a couple answers if I may.
The one that I made the biggest multiple on was i made a we made my brother and i before we started calling m13 made
a thousand times our money on coinbase and that is not playing bitcoin i mean like we invested in
the series a of coinbase at a 15 million valuation so a thousand x on that so if you put in ten
thousand dollars you would make $10 million.
That'll never happen again for a myriad of reasons.
It's a great question.
I'm trying to think what company we've invested in has had the biggest exit.
You know, we've been in companies, you know, early like Pinterest and Lyft and Ring the Video Doorbell, but it's such a function of how much capital goes in.
And honestly, it's about getting out at how much capital goes in. And honestly,
it's about getting out at the right time. Because we've had some now like Lyft, we did very, very
well in Lyft. The market cap is not reflective of that, but I've sold all my shares in Lyft
years and years ago. So I think it's a lot about that in terms of, can I give you an answer of one
that I think has tons of potential now? It's the one sitting right here in the picture called Lifeforce, which is a kind of a vitality business. We started
about 18 months ago with Tony Robbins, who's a old friend, and we'd invested in some stuff together.
And he said, I want to do something with you. Call your shot. And I was like, that's pretty
cool. Tony Robbins said he'll kind of do anything that I come up with. That's pretty fucking cool.
Yeah, that was one of those moments of like, okay, maybe I made it when Tony Robbins says you're my guy for like
anything that's has a tech angle and a consumer focus. We went back and forth on some ideas,
couldn't quite figure it out. I knew had this book coming out called life force all about kind of his,
his latest and greatest longevity things, but really more like vitality, meaning feeling better
today. So you can hopefully live longer tomorrow. Cause there's a, I think a big distinction. And I was like, Tony, this is,
this is the one that we should, we should do because can we take that 1%, if you will,
concierge experience, medical experience that we've all been lucky enough to have, or, and
then take that to like a much broader set of the population. Not, not the other 99% yet,
but like the next 10% and the next 10%. So I know you guys have had like a Peter Atiyah on,
like, can we take, I don't even know if Peter Atiyah talks about what he charges for his
concierge practice, but so with something like Lifeforce, I just feel like, can we just,
so many people don't have access to good food and good healthcare, or just like knowing what,
what the best practices are. And so luckily I'm not doing most things for money these days.
Tony Robbins certainly isn't or Peter Diamandis. And we just said, wouldn't it be great to do
something where maybe someday, you know, tens of thousands and eventually hundreds of thousands
and eventually millions of people would have access to like the best parts of a concierge
experience where it's everything from, you know,
checking your biomarkers to telehealth to certain supplements we might prescribe and
performance health coaches. And we kind of build from that, but it's just about building
like a quarterback of your health in your pocket and just kind of giving you that glide path
because most people just don't know where to start. And we've all, I'm guessing most people
we've had on are lucky enough to know how to do that. But if you don't know where to start, it just would feel great to feel like we put someone
on that path. So I think those kinds of companies can be huge. You said you're not doing things for
money. So what are you doing things for now? When you wake up in the morning, what was that shift?
What's your reason? Well, I'll kind of give you an M13 answer and my
personal answer. My personal answer is I feel like for two, two and a half decades, maybe my whole
life, I did all the things that other people wanted me to do to either have a chance to do
whatever I want to do or to be successful, not even just as a human being, but be successful
with a capital S and successful
in terms of money, which is the easiest measuring stick. And it's only the last couple of years I
got to a point where it's like, I have more money than I ever thought I would have. So I feel really
lucky. I don't live a crazy life. My brother's spending outpaces mine a little. And so it's not about having a bigger this or
a better that. I'm really lucky that I don't long for things that I could want. And conversely,
for M13, I don't think the world needs another venture capital firm, but we think they need
another kind of venture capital firm doing things differently, whether it's the things we invest in
or how we're resourced, which I can go into. And so we said, wouldn't it be great to do well by doing good, but just
really say, hey, maybe 10 years from now, how venture capital works has kind of evolved or
how it adds value. And we were a part of that solution. And so I really want to be at the tip
of the spear of big innovation, which I think means for us, it means it kind of has to start
with technological innovation, but then always kind of keeping, we love to talk about future of consumer behavior.
So everything we focus on has some kind of future element. We invest in the future of health,
AKA something like life force, future of money, future of work and the future of commerce. And
we think that kind of encompasses all the places that, you know, people are looking. And yeah,
to me, it's about, it's a weird thing to say in my 40s,
but I really feel like it's about legacy and impact,
which is a great place to be.
I'm sure you guys,
have you guys read about the Charles Feeney guy recently?
You know, we were skiing one time in this place
and we met his business partner, silent business partner.
When?
When we were in Stoddard.
It's kind of like when you guys met me and didn't remember.
Remember Tony?
When?
Tony Michael and I, we hadn had been in touch in passing.
Tony.
Oh, yes, yes.
And he told us this story before this,
and he gave me a book that Charles Fien wrote.
It's called The Billionaire Who Wasn't.
I don't know if you've seen it.
It's on my bookcase,
and it's got this incredible story of this guy
who made all this money,
but he basically donated all of it.
I just ordered it.
I had read an article, so I knew who he was,
but he's one of the co-founders of Duty Free.
Made $7, $8 billion in his his lifetime but then started giving it away while
he was still alive he just he just passed away recently at 92 silently to gave away all of it
yeah mostly anonymously flies commercial lives lived in a two-bedroom place in new york and
rode the subway which i can relate to but i mean how cool is that it's actually see that impact
i have a question and you know, we in a completely kind
of different lane in conversation, which I feel he did not get enough credit for what he was saying.
We had Dan Bilzerian on the show and he was talking about basically that the things that
derive the most happiness for him now is really not the money. And I think he's known and he's
created this image as this playboy that's, you know, spending lavish amounts of money and doing
crazy things. But he was saying it's like the little things in life that doesn't cost anything to make
them most happy.
And a lot of people give him shit like, oh, easy for you to say you have money.
And I'm sure people will pull a clip from you saying, okay, easy for you to say in the
position you're in.
But what are some misconceptions or some things that you thought money would bring that it
didn't bring? Or I guess maybe some thoughts around once you got comfortable,
what changed and what didn't?
Well, we all have something different tugging inside of us, right?
And money doesn't solve that.
Money doesn't guarantee you love.
All those things.
And I think for me, I'm just one of those person,
wherever, wherever, like I put a lot of effort, usually something happens, hopefully good,
but something happens and where I don't. So if money had been at the, had been my number one or
number two priority for a long time, like it had that part worked. And then other things that were
like four or five on my priority list, like starting a family hasn't happened yet, you know?
And, and it's not that I don't want to make any more money, even though it's not really the focus,
but I just realized if I don't flip the priorities, money just has to go much further down the ladder,
not even money, but just like anything involving that. And I have to put the other, you know,
personal things further up. And listen, I also want to just say, I acknowledge what,
what people say to Dan, because I've had it said to me, like, Oh, easy for you to say.
And I agree. No one should feel bad about their circumstances. We've all, listen,
I've had my hardships, but I'm not comparing those to anyone else's. But I also think,
I also really love, you know, to those who much is given, much is expected. And I own that. And
I want to, but if I don't, you know, if not me, then who? Like, I just sat here and told you,
I've had incredible opportunities in my head. So that's a lot of pressure too. But I,
I want to take that pressure because gosh, like I, I would be so disappointed in myself for my
parents and the incredible job they did if I didn't try and do better. And I think a lot of
people that say easy for you to say to need to look inward. Well, I think that that's a, that's
a projection of something that they're insecure about onto someone else. I don Well, I think that that's a projection of something that they're insecure
about onto someone else. I think that that's something if someone's saying that, you got to
sit with yourself and figure out why you're saying that. How do I say this eloquently? I think
sometimes they will look at somebody who's reached a certain level in life that is maybe
unrelatable to most people. And because it is not relatable anymore, like it's not common, I guess,
they will discount the information that's being said or shared. Does that make sense?
Yeah.
And so when I was listening to Dan and I just was observing the comments come in, I was like,
no, there's some value into what he's saying because so many people glamorize and chase
dollars and money and think it's going to be the solve to all of their issues and problems.
And listen, to a point, obviously, if you're struggling to pay rent, you can't buy groceries, like, you know, money is
obviously going to be helpful. But I think this endless pursuit of just more, more, more, what he
was basically saying is like, at some point, you're going to have extremely diminishing returns if you
don't find a greater purpose outside of that pursuit. And it's also the, again, easy to say,
when you don't have any money, of course you have to prioritize money.
But once you make some money, and research shows if you read these happiness indexes,
it's like $60,000 a year.
Above that, it doesn't bring any more happiness.
Now, I don't know all the footnotes of like, that might not be $60,000 in the US, that
might be spread across the world, and 60,000 US goes a lot further in some parts of the
world.
Inflation's pretty high right now.
But I would say it is, I mean, I think it seems pretty clear and you go back and read
ancient Greek philosophers. I mean, people knew that 2000 years ago. We've just kind of
lost sight of it. But I think for me, I always want to go back to like, if I'm going to not
make it about money, then I want to prioritize my time around money because that's the one thing
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I want to talk about your time, your time management. You're a high performer how do you
manage your time you've got a lot going on and I mean like I want you to tell me
do you have a color-coded Google Calendar do you wake up at a certain
time like what are the little things that you do to streamline your day for
efficiency I've had lots of iterations of how I've, how I've spent my time. I mean, I, I used to
be really proud of like, go look at my calendar. I still use, I'm an Outlook guy and just go,
you go find me a white space in there if you want to talk. Right. And, and I used to take a lot of
pride in that. Now I think one, I've definitely become a believer. Have you guys, has anyone
ever referenced Paul Graham? So Paul Graham's like a real innovative thinker.
I think he started in the tech world.
He writes a lot of great thought pieces.
So he has one that I love called
maker versus manager schedule.
And the gist of it is something like this.
If you're a manager, you spend all day,
you know, in meetings.
We go from meeting to this or that.
And if you're a maker, a creative person,
you need to leave lots of blocks during
the day to like create or to like have that creative juice come over you. Right. And so I
love this. And so his whole thing is like, you know, if you're a creator and you have nothing
booked for that day, but you have like one meeting with Courtney at one o'clock, you wake up in the
morning, you're like, Oh, breakfast, I'll get a little creative. But in the back of your mind,
you're like, I have that meeting at one o'clock. It's nine in the morning, you're like, oh, breakfast, I'll get a little creative. But in the back of your mind, you're like, I have that meeting at
one o'clock. It's nine o'clock, then it's 11. Then you go, I got to get ready for the meeting.
We take for granted how much it sideswipes a big portion of your day. And so I've kind of tried,
for sure I'm a manager, but I also consider myself a maker in some ways and a creative.
So what I try and do is a couple of days a week, but this is what I try to do. It doesn't always work this way is especially on the West coast, because you're
always kind of wake up chasing the day from like the afternoon on like two, three o'clock on,
I try not to book anything the rest of the day. So I can like have long blocks where I don't look
at my phone or go for a hike by myself, or just take time to like, think about what's working,
what's not all that. So I've actually made a big effort to put more slack
into the system in order to try to go slower to eventually go faster. That's one thing.
Most of my ideas are not my own, but I do read a lot. So I think I do like the how your first,
this is easy for me to say without kids, how that first hour or two of your day goes,
so two of your day goes. So I try really hard hard not to schedule meetings before like nine or 10 AM. So I can get up and like,
when you're on the West coast and I mainly live in LA, you know, I wake up to like a hundred emails.
So even just getting through those and figuring out what to look at, what to delegate, what to
look at later, how to prioritize it. I mean, that's a real art that I think is one of my
superpowers. Like if I have to, I can go through those 100 emails in 10 minutes,
not have read all of them, but at least decided what to do with all of them.
And so I like my day to kind of be like the morning because that is the quietest time to
be like an a la carte mix of those. So I love things that are net. I call it net zero dead
time, meaning I'm doing something while I do something else that I would have done anyway,
so it doesn't cost me any time. Meaning, I go in my infrared sauna for 20 minutes, but I do it while I read some emails,
so I'm kind of catching up. Do a little cold plunge, do an Andrew Huberman, go and get some
light, go for a little walk. I have a pretty extensive menu of things that I do. And depending
on the day, I kind of mix it up a little stretch. I went on a trip with Charity Water. If anyone
knows that organization that builds wells
and brings clean drinking water,
people have never had it.
About five years ago in Africa,
there was a guy on the trip who runs around everyone going,
do you stretch?
And everyone's like, why is this guy asking me?
Five years later, if I do this like five minute stretch
in the morning, it can even be three minutes,
but it's like three to seven minutes.
I feel markedly different during the day
if I just do it like a couple of these stretches.
What is the stretch?
You gotta tell us the stretch.
I'm kind of, I'm like a low back guy
because we all sit a lot.
So there's only one chair called All 33
that I can sit in for eight hours.
Yeah, All 33.
All 33 is Dennis of Peak Wellness's chair, Michael.
Dude, Dennis is the man.
Can we just agree?
Dennis has been on the show.
Dennis takes care of everyone in my family,
including my 78-year-old mom.
And that is a guy.
Talk about givers and takers.
That is a giver.
He adjusted my implants on Instagram story.
He moved your baby.
He moved my baby in my stomach.
He moved my baby.
You know, it's funny.
Dennis has been on this show.
I love Dennis.
I think he's one of the best people.
I went to a
dentist a dentist not dennis a dentist like three months ago and this person took care of me like
you know just for a teeth cleaning in a way that like you're just like wow just people who are so
passionate about their craft whatever it is if they're a teacher god bless them because i couldn't
do it if you're a dentist i couldn't do it if you're dennis i mean it's incredible and dennis is one of those people just like he's like a true healer when i told
michael i'm like i have this guy everyone says they have a guy i'm like no i have the guy the
guy that the guy is the guy you used to want to have a doctor and a lawyer now it's like you want
someone like a dennis i mean you want dennis over the best yeah okay so you sit in all 33 chair i've
posted this chair you guys only one that doesn't make my back or i can sit in all 33 chairs. I've posted this chair, you guys. It's the best. Only one that doesn't make my back hurt.
I can sit in eight hours straight.
Other than that, it's like 90 minutes and I need to sit up.
That's the only chair I sit in.
What was the question you wanted to ask?
My question?
We got to you, Will.
No, I like how you're giving us tactical things.
Yeah, I mean, everyone's different.
But if you sit a lot, it's all in the lower back and hips.
So I have to do a lot of twisting.
Like I have to do like a lot of knees in the chest, rotate over, like a lot of twisting. I have to do a lot of knees in the
chest, rotate over, a lot of twists. I can get some good cracks usually, even though it shouldn't
be about that. But I definitely have to do some twists, just like a little mini yoga, a little
down dog. I just recently started doing a little plank thing. And actually, it's amazing. They say
if you do those planks, it actually helps with having a little lower back stiffness.
And it so does, which is kind of counterintuitive.
You and I could go off because you, what did you call it?
Net what?
I think I made this up.
Net zero dead time.
So I do it while I'm doing something else.
So other than the stretching,
which I don't do anything while I'm doing that,
everything else I do, I sit in front of red lights. i stand on the vibrating plate you have this thing called a biocharger
she gets a facial and then she's doing emails i lay on my pm pmf mat and like put my feet in the
the shake machine while i return emails that's my favorite thing to do and when people are like how
do you get stuff done you habit stack it yeah and i. And I love the, I first heard that term from Arianna Huffington, who's a dear friend of
mine and I'm on the board of her company Thrive.
But it's all about those like habit stacking, the little resets during the day.
Like you're upset about something and she has these like Thrive resets.
It's amazing how I can feel totally flustered, really upset, 60 second reset.
That's all it takes to reset your nervous system. So I love those because I'm sure like you guys get enough stuff thrown at me during the day
that if I don't start with some level of Zen or try to do a little bit of that,
it can just spiral quickly. I think that what you said about the calendar and having space
open on the calendar is so important. Ryan Holiday has this picture he always posts
and I always send it to my assistants.
And it's like, he thinks a day is successful
when there's nothing on the calendar.
And you are right.
As you grow as a business person,
it's like a badge of honor to show how busy you are
and how many different colors are on your calendar.
What the real fucking flex is,
is having nothing on your calendar so you the real fucking flex is, is having nothing
on your calendar so you can create what you want to create. Yeah. I mean, it's GSD, get shit done.
Whatever. Can we swear on this podcast? It's been done before. Okay. Sorry. But that's the measure,
right? It's not about anything. It's busyness with a Y versus busyness with an I. It's just
getting done what you endeavor to get done, right? And I think it's just getting done what what you what you endeavor to get done right and i think
it's just so important to to leave that slack in the system and i just think it's
yeah i mean that's that's for me what it's i think to take things oh sorry i lost my train
of thought you saw that but it's come back okay here's here's something that i actually think
would be counterintuitive to most people i took control of my calendar myself about three years ago.
Oh, fuck.
Yeah.
I don't think I should do that.
So listen to this.
Oh my God, Courtney.
So my brother uses an outsourced assistant
for his calendar in the Philippines.
That's a whole different story
because the time zones and everything.
And every time I try and use her,
it's, you know, there's complications,
we'll say, because of time zones.
But taking over my calendar does an interesting thing.
I like him the final say on anything that goes on my calendar because what I found was there's just
too much going on that I don't need to do. And if it's not a heck yeah, it should be a no. Do I need
to be in that meeting? There's already seven people in it, 12 people in it. So one, it made me just
say no to a lot more stuff. I think as you get, for me as I get older, it's more about simplifying
and pruning than adding. And that's so hard because I can speak for my brother when I say
he and I got here by saying yes and yes and yes, and just stacking and stacking and stacking. And
when you start at Goldman Sachs, working 80 hours a week seems like a vacation when it's for
yourself. So now it's about saying no and simplifying. But then the other thing that
happens with the calendar is like, say people in my company, who should I go to get this on your calendar? Oh, right here. What do you want? I'll come back to
you. You know, when it doesn't go through your assistant, nobody sneaks anything on there.
Nobody bullies anything on there. And then it's really ingratiating when Tony Robbins is like,
this assistant just emails me, there's no one you want to do this. I was like,
there's someone who could do it, but I'd just rather do it. I promise you'll have one email
with me. I'll say this time, if you say no, you give me two times and we'll pick one.
This motherfucker is going to take this tip.
I see his wheels spinning and spinning and spinning.
He loves these tips.
I like that.
I think that it becomes a challenge.
I mean, and listen, this is people are different stages,
but in the beginning of our career,
and I know we're getting on time here.
In the beginning of our career,
it's like you say yes to so many things
and you get in that habit.
And I think at some point you have to transition
and be more selective and say no to more than you say yes.
And it's counter-advice because to your point,
like Lauren and I were the people
when we started this show,
like we were working different jobs.
We had different businesses.
And we were in the car.
We say yes to everything.
We'd get on a plane.
We were carrying all that.
Now it's not that we say no to the show,
but the point is that formula of trying to say yes now,
we would run ourselves into the ground
and we wouldn't be able to be as focused as we are.
No is actually the word.
And the irony is that you almost have one process
to say yes for a long time before you're in the position
to be fortunate enough to say no.
But some people never get to the point
where they can say no.
Yeah, I love things even like, like I said,
I'm an old school Outlook guy
because that's what I kind of grew up on email wise.
But I love timers.
Do you use timers on emails?
I use the twisty ones.
Yeah.
I use tons of timers.
Like the Pomodoro method?
Because it's like this.
It's like,
there's people I have to reply to
right away
and there's people where
if I reply right away,
all that's going to happen
is another email comes back
and I know parameters of things.
So it's like,
well, that doesn't need to happen
until next week.
So I want to respond.
But if I don't respond now, I do net zero inbox, where as opposed to
my brother does like 30,000 unreads. So I reply to that email right now, but then I set on a timer
for three days from now to go out on Friday. And it's like, great, we're on pace for next week.
So it just paces out things while still keeping them moving. Now, occasionally you have some
faux pas where I set the timer wrong and it'll be like hey great talking to you whatever whatever like
we didn't talk and i'm like whoops the timer didn't happen so i sent the email right about
timers for egos for egos i use boomerang do you know boomerang boomerang yeah yeah but but like
just as a pacing thing to your day i love timers to like because i'm like the timer slows down the
pacing of your day wait Wait, so hold on.
I have to understand this.
Hold on.
You'll learn something here, Lauren.
I promise you.
You send Lauren rapid fires emails on like a psychopath.
No, I have a tip on it.
On like a Sunday.
My way works too.
It's a different way.
No, no, no.
No, no, no.
It's chaotic.
She writes rapid fire emails on a Sunday.
So no one can respond.
Like 40 of them.
But then they hit the-
600 emails.
But if you used a timer those emails would go through
but they would go through
in like an appropriate time.
No, I don't.
The time that I have
to respond to my emails
is on Sundays.
I love it
because no one can
write me an email back.
So I get it all
out of my inbox
and it's all delegation.
Where does this email go?
Here you go.
And then I go
like this
until next Sunday
and I don't check my email.
But half of them come to me.
Too bad.
I think when we were all on email,
I got the out of office saying your way of writing.
That's another boundary that I've set because-
I like that.
That's a boundary.
It's like my email to me is a tool.
It's not somewhere where I live.
You know what they say?
The inbox is someone else's to-do list for you,
not your own to-do list, right? And guess what? That letter shuts down things that maybe I don't
need to see or maybe I don't need to be involved in or maybe I don't need to respond. It shuts it
down. It does. I can't argue that. I would say my learning on the Sunday is, one, let's say it's my
internal team. I just don't want to burn people out. So an email. I would say my learning on the Sunday is, one, let's say it's my internal team.
I just don't want to burn people out.
So an email that I would reply to Sunday morning,
I set a timer for Sunday night.
And on the off chance they want to get ahead of their week,
the real industrious ones,
they'll check their email at like 9 o'clock on Sunday,
but it's not like I burned them.
And if they don't, they see it Monday morning first thing.
That's smart, though.
That's what I'm saying, Lauren.
So you're saying I can do my emails on Sunday,
but don't overwhelm
it takes a touch
more effort
but it's funny too
you also learn
let's say
I used to be one of those people
that like
would almost have a list
of I want to meet
these people right
this is important
who I want to meet
sometimes for reasons
sometimes for no reason
and what you learn is
because I would always
reach out
a lot of them
I didn't have their
cell phone number
but I found their email
Tim Cook or whatever
it's almost 50-50 those that respond on Sunday because your email is a better chance I would always reach out. A lot of them, I didn't have their cell phone number, but I found their email, Tim Cook or whatever.
It's almost 50-50.
Those that respond on Sunday because your email is a better chance of getting seen
with those that you piss off
because you emailed them on Sunday.
It's about 50.
So then I find out.
People get pissed if you email them.
Who's checking their email?
I don't check my email.
But that's what I'm saying.
So I don't know if anyone emails me.
That's good.
You're equal.
I think you're right.
Some people will get irritated, myself included,
when you email me 18 times.
You do the refresh thing.
I don't do that.
Because I like to do zero inbox too.
Yeah, I think some people...
Zero inbox.
But I do think whether it's timers,
it is like Tim Ferriss taught me a long time ago.
I think we both agree that there's something like timers
or something like batching.
Tim Ferriss has a different kind of company than I have,
but he kind of used to say he did it we'll check his email once in the morning
once in the middle day and once in the end of the day short of like the building burning down what
could possibly need more than that and i do i don't adhere to that but i feel like i've done
that for periods and the world doesn't end right you and michael are very similar with your
relationship we've covered a lot of ground i'd like to keep covering i mean yeah well you can come back on do you like pareto's law that's
one of my other big guiding principles what's pareto the 80 20 80 20 rule and i actually think
it's sometimes 80 20 and depending on what you're talking about it's somewhere between 80 20 and 95
5 what do you apply it to though what do you use that give me something i'll apply it um let's say
i want to write a book. Well, I guess it would
be for Pareto's law. I mean, it's 80-20, meaning like, I guess that's like the how you write your
book. Like maybe you decide for a while you're going to focus 20% of the book if you're in no
deadline, 80% of your day job or vice versa. But it's like Pareto's law is like this, like
you're a salesperson. For most sales organization, 80% of your clients do 20% of your sales. It
should be the inverse. You should have your top 20% of your clients doing 80% of the sales. Think
how much easier life would be if you can go deeper with those. Like diet. I think diet,
depending on how strict you want to be, 95.5 or 80.20. For me, I'm an 80.20 sort of guy because
there's been points where I've had a really good six-pack and I know what that's like. It's no fun. And I don't have a real good reason to. So I'm like at 80-20.
Try to be healthy 80% of the time so I can enjoy the other 20%. But if I want to have a ripping
six-pack, it's got to be like 95-5. You know what? I've learned a lot this podcast.
Pimp out your book. Everyone needs to go buy it. It is so digestibleible and amazing I screenshotted it to Michael
and was like
we have to get this guy
both of you guys
we have to get Carter on
at some point too
you should get Carter
you should get Carter
and Paris on
that'd be awesome
that'd be fun
to get both of you two
fun fact
you know I've been on
your podcast before
I love these blank looks
don't edit this people
I've been on your podcast before
I mean mentioned
on your podcast
you've been mentioned
on the podcast
I'm like maybe
more than once but we've done a lot of these brooke connected us who mentioned her i was
listening to brooke she was talking about sitting with a friend who was in a relationship trying to
decide kind of analytically if if the person like i can't remember what she used but she said it was
you kind of yeah that was me wait wait wait she should told me the story because i want to remember trying to decide if
like this was the person you wanted this was a person and kind of like digging into like what's
it look like five years from now in 10 years and now and the mother of my kids and what are the
traits i'm looking for and it was funny because i was listening in preparation for this and then
she's referencing she's having this talk with someone and uh then she said something like a
friend of mine and then she said brilliant this talk with someone. And then she said something like a friend of mine.
And then she said, brilliant.
So I was like, okay, probably not me.
And then she said, older friend.
And I was like, and then she just described it all.
And I was like, oh, wait, no, that's definitely me.
So I texted her and I said, was that me?
You said older.
She said, well, I like to keep my friends secrets.
So I appreciate it.
You almost just tripped me the fuck out.
I was like, wait a minute.
I was trying to think.
I'm like, we've done a lot of these shows.
One of the things that I think makes you so successful after interviewing you,
and I'm saying this on air.
We figured you out now in an hour and a half.
You are a very thorough person.
It seems like whatever you do, you give 100%.
Don't you get that from him?
He's a thorough person.
Well, do you remember when you guys almost made me cry about my dad?
My first quote I gave was my dad used to say, when
Courtney really wants to do something, he's into it. Watch out. When Courtney doesn't really want
to do something, watch out. But I think that's true. You're going to be a good dad. I hope so.
I'm ready. Where can everyone find you and your book? Our book is called Shortcut Your Startup.
It's been out shockingly for five years, but I'm really proud of the fact that actually the sales are like very consistent over after the initial pop, which hopefully tells me
it has some longevity and people are getting something from it. My Instagram is, there's only
one Courtney Ream. So if you Google hard enough, you'll probably probably find me on LinkedIn,
just at Courtney Ream on Instagram. And then of course my company M13. So at M13 or m13.co
because.com is so passe. You can come back on anytime.
No AI cold emails.
No AI cold emails.
No AI cold emails.
But if you do an email, I'll guarantee if you do an email with some personalized thing
that resonates, I promise I'll report.
We need the audience.
What if I send a thong?
Everyone send your thong to Courtney.
I'd rather take Michael's.
It's just safer at this point.
You send yours to Charlie and Warren.
Thank you, Courtney.
Thank you for coming on.
Thank you so much. Thank you for coming on.
Thank you so much for having me.