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Max Crowley on Uber’s Wild Early Days_ Selling Bandit_ and Betting on Himself Again
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Let's start back with the journey in
Uber. So you joined, you were what?
Employee 25. Yeah, 25. I was 24 years
old. That's nuts. And there was only
probably 15 people at the company when I
started because you know they give out
the employee IDs which people leave. So
I was employee ID number 25. I mean
there was Oh, interesting. There was
probably 15 people maybe less at the
company when I started and we were
Chicago was the fourth city. So it was
literally, you know, company launches in
San Francisco mid 2010, New York was in
the spring of 2011, and then August was
Seattle, September was Chicago, and I
joined in August to to get it going. How
did you end up at Uber?
[Music]
Welcome back to season 4, episode two,
The Turning Procast. Today we have Max
Cwley, who's a struggling podcast host.
Thanks for joining us today, Max. Thank
you. Thank you. I appreciate it. Help me
get my name out there so I can such a
cool introduction for someone who has
sold a company, who has worked high up
at some of the biggest companies in the
world as we know it today. Uh so I think
it's a great way to like humble yourself
as you as you start on this new journey
as a podcast host. Thank you. Thank you.
I mean, you got to got to try and always
bring the ego back down as much as
possible. I mean, there's no better way
to do it than starting a podcast. I can
tell you that as someone who uh who was
there one day. Look, we're um I think
this is maybe episode like 77 or
something in that range. Way to go, man.
That's awesome. Which is crazy to think
about for sure because I mean I think we
talked about this, but the statistics of
podcasting, it's like the way the
industry or the concept is set up is
like you're designed to fail because
it's so [ __ ] hard to do and it
typically requires a lot of resources
and a lot of money and so most people
just like can't make it. But my
mentality with it is just that like the
number one fa way that you fail is just
by giving up. So if you could just stay
in the game long enough, hopefully, you
know, it turns into something. No, it's
funny as I've talked to people in the
industry and it's like what advice do
they give you? And then people are like,
"What's your goal with the podcast?" And
it's like, "My goal is to continue to do
it." Like, can I just literally put one
foot in front of the other, keep
recording, and as you said, good stuff's
going to happen. I'm going to meet
people. It'll be interesting
conversations. I'll whatever the thing
might be. But yeah, I mean it's very
easy a lot of the hardest things in my
life. I like right before you do it, you
say to yourself all the reasons that you
shouldn't do it. You start you start
thinking I don't want to do this. I
what's what are all the excuses that I
could have to not do this thing right
now? And if you just give yourself a
little bit of that push, it's where all
the the magic is made. So we'll in a few
minutes we'll go back to the beginning
of your journey because I think you have
a pretty crazy journey. But I actually
think the podcast thing is a very
interesting place to start because you
went from working in like the most high
growth chaotic environments uh arguably
in like startups as we know it for
people listening like early Uber sold a
company to go there through these crazy
trajectories at both companies and now
you're in this phase of doing something
that is a lot more slow. It's a lot
slower and a lot more there's a lot more
intentionality around it I think or you
have the privilege of that being the
case. What was that like mindset shift
for you after so many years of like in
the trenches that you're like I want to
try something that for all intents and
purposes from my perspective is so
vastly different. It's I mean look I
think one piece for me is I definitely
believe in reinventing yourself as much
as possible. So I I don't think I was
ever a person to do a 20 30 year sort of
corporate track and keep rising the
ladder and like I love that stuff. I
respect it. I've worked at amazing
companies that you know just for
whatever reason I I still stayed there
long periods of time in the scheme of of
how long people stay at companies these
days. But I think for me you know it's
part reinvention. So when I do something
new I want it to feel different. I want
the the success goals, the metrics to be
different. And so, you know, first piece
is just reinvention. And then I think
the second thing is look, it's a it's a
it's nice to be able to take time off
between jobs. I know that that's for the
most part a privileged uh thing that
I've had the ability to do. So, I'm
super thankful that I have had the
opportunity to take some time between
these various things that I've done. So,
you know, took some time after Uber,
took some, you know, joined Gouff,
taking some time now. But for me, taking
time is not just I'm laying on the couch
and chilling. It's actually, yes, I do a
hard reset. I try and travel. I try and
be mindful. I try and really reset my
brain, but then I'm back in grind mode.
So, this is a version of grind mode.
It's just it's just, you know, sort of
maybe triggering different parts of me.
I have a friend who I was with uh two
weeks ago. He was the CMO at a
billion-dollar brand that you're very
familiar with that I'll tell you off
record cuz I don't want to out him but
he was there for a long time left there
and for the last like seven months or so
has been on this like journey of like
finding himself again because his whole
thing was like for the first time in my
life I don't have a commitment where I
didn't have a significant other I didn't
have a dog I didn't have kids I didn't
have a house every moment of my life
went into this business and then the
second I stepped away from it I realized
like I had been running away from my own
thoughts and like sitting with myself
because it's so easy to distract
yourself which is doing work all day
every day when you're in a very
stressful fastmoving environment. I'm
curious from your perspective as someone
who's done this, like how do you what
are the things that you tell yourself or
the parameters that you set for yourself
after going from like allin 100 miles an
hour to like stepping back with no
responsibilities professionally at least
and uh having the discipline to not just
like jump into the next thing right away
because obviously the bigger things you
do the easier it is for you to get like
poached or more opportunities come your
way. So I'm curious to understand like
your own selft talk and that journey of
like actually forcing yourself to like
take a minute to breathe. For sure. I
mean look I'd like to say I was better
at the breathing piece but I'm trying to
like truly take the time. But I think
the the biggest thing for me is number
one still having the structure. So still
saying I'm going to try and get up as
early as possible. I'm still going to
try and go to the gym in the morning.
I'm still going to try and meet with a
bunch of people. you know, still have
the sort of day-to-day structure like I
am working in a way. It's not it's not
like I'm totally disconnected from
things. I'm still sending out emails and
doing cold outreach and still trying to
build the network and figure out what
people are doing. And so, you know, I
think for me, you know, again, it's not
like I'm getting up at bed, you know,
out of bed at 3:45 and whatever that
stupid meme is right now and throwing
water on my face. Saratoga spring water.
Yes. But I mean, you know, decently
trying to still be an adult and and take
the time and be appreciative for it. And
then I think for me being able to trial
things as much as possible has been a
big benefit. So, the podcast allows me
to still work a few day few hours a day
on something, still manage someone,
still meet a ton of people, hopefully
get smarter, learn something that I
didn't know before, but I'm kind of
dabbling in that. And I can also advise
a few founders, and I can also maybe
incubate something in a small way and
just test something else out there. And
maybe I can even do a job for a few
hours a week and start to see how that
goes. I mean, when I transitioned from
Uber, I took some time off first. I
traveled. I went to Asia and around the
world and like really tried to take some
time, did yoga retreats and maybe did
some mushrooms and like whatever else to
like try to reset. And then the next
phase was a lot of all right, I want to
meet with people. I want to figure out
what's going on. I want to learn as much
as possible. What are trens? What are
VCs investing in? What are things people
starting? What are startup studios
starting? You know, if you go talk to
one of those teams, they've got a list
of like a hundred ideas on the wall
they're thinking about. You'll see, you
go to studio to studio, you'll see a
theme in that and you're like, "All
right, this is what the market's working
on. This is what people are thinking
about." And then from there, you know, I
worked on a private jet startup for a
few months for a former co-founder of
Uber who just had another project that
he was working on and trying to do side
project, private jets. Um, and like
look, I love the company and I loved the
time, but it also was clear, okay, this
isn't a project that I want to work on
long term. I'm pumped that I met some
people. I'm pumped that I learned about
a new industry, but then that helps me
decide. I mean, I had a sperm banking
business that I was kind of incubating
and there ended up being a few of those.
And um, I still love the idea. And then
I decided to start a coffee company.
very desperate ideas, but you know, this
time and having some structure, not
crazy amount of structure, but some
structure to I'm gonna try something for
a bit. I'm gonna hopefully know when to
pull out so that I don't just get all in
on something I don't want to do. And
then that helps you. Okay, now a few
months in, I feel really comfortable
about the decision I'm making versus
jumping into something and then a couple
months being in being like, [ __ ] is
this maybe this isn't the thing I should
have done. What are the signals that
you're looking for when you're dabbling
in something to know if it's what you
should be doing long term or not? I
think I definitely want to be able to
see an impact in what I'm doing. And so
with the podcast, we can go to a bar
right now and I may be doing this
actively and say to the three people
sitting at the bar, "Hey, do you have
Spotify?" At which time they look at you
crosseyed and they're like, "Of course I
have Spotify." And then I say,
"Subscribe to the early podcast." Wow. I
love that. I'm not doing that enough. Oh
man, I am
that's because it's for me it's like all
right in the least I know I'm good at
that. So I made that that's valuable for
something. I mean my Spotify subscribers
are almost all handtohand combat. That's
so cool. Um and so I mean it was wild. I
was walking down the street with a buddy
and we saw a guy standing there and my
buddy goes, "Hey man, I used to live in
this building. Like which unit are you
in?" He's like, "I'm in this unit." And
my buddy's like, "I was in that unit."
Like, "How old are you?" And the guy's
like 25. And my buddy's like 50. And the
guy's like, he's like, "You're going to
make it one day." Like, "I was 25 living
in this building." And then I said to
him, "Subscribe to the early podcast."
And then I got a DM from the guy and he
was like, "That was so cool that I had
an interaction with your buddy. I'm
pumped listening to the pod. Loving it."
So, like I
it's I love to be able to control and
feel like the effort that I'm putting in
is getting real value. And as companies
get bigger, it's harder for that to be
the case. And that's probably why I've
gravitated towards things that are more
early stage, more fruits of your labor.
And again, look, anything that's worth
scaling, it's going to then be hard.
You're 77 episodes in, it's going to be
harder to get the random subscriber off
the street. you got other things to do,
but you know, I love that beginning
stage where you can feel that and then
also scale with, okay, now we get people
that do it and we build teams and
whatever else. But that's the part that
I I love. Yeah. But I actually think
that last point you made is important,
which is like you can't lose sight of
what got you to where you are. Like I
don't I think I have 77 episodes in the
bank, but there's no reason I haven't
told one person standing on a sidewalk
at a red light like, "Have you
subscribed to my podcast?" So I think
those are actually things I need to
start doing regardless. Look, I I don't
know. I think I have a thousand
subscribers on YouTube, which is like
not zero. Like, it's it's it's cool. The
way that I always someone said this to
me cuz on the spectrum of like viewers,
that's nothing. But if I said to you,
we're going to put all my subscribers
right in front of us like in the stands
to listen to our conversation. A
thousand people is like not zero. And
they haven't unsubscribed. And they
haven't unsubscribed. Like that's a real
Those are people that are fans. They've
subscribed. They're in. You should be
super proud of that. I mean, it's I am
partly inspired to do my thing because I
saw what you're doing. And, you know, I
think I the only reason I even hesitate
in saying that is because I want to be
able to actually come through with that,
right? I think a lot of people probably
say to you, oh, you're starting a
podcast. Everybody's got a podcast. He's
like, well, no, not everyone has a
podcast. A lot of people do or a lot of
people do or did, right? And so, it's
it's I'm inspired by what you've done
and now I want to be able to like meet
that bar, right? I want to be able to
meet that threshold and actually also
keep putting stuff out and and try and
make it a thing and not give up because
it's so easy to give up. Yeah, that's
the that's the biggest thing. I think
we've talked about this, but my my
philosophy around a podcast is how do
you optimize for consistency and not
virality? So if you think about like
what are the friction points or the drop
off points when you decide to quit, it's
like if you try to solve those pieces
first to just give you to reduce
friction to do it for a long time. That
to me is the the hack, right? Like
you're living it right now. You walked
into the living room of my apartment
where I'm going to film. My couch
cushions are in the in the stairwell.
Like it's it's pretty like this is
pretty startup vibe if you ask me. This
is like no budget hacky. Like me and
Owen, who's the producer, like carrying
couches to move them out of the way to
do this, but I'm also going to get 4
weeks worth of content out of like the
grunt work that we put into this today.
So like, you know, I if I can do this
for an extended period of time, maybe
one day someone will believe in what I'm
doing enough to be able to pay for me to
go sit in a nice studio that already has
everything set up so me and Owen don't
have to sweat for 30 minutes before we
start. But like I I also know it to be
true that you need to enjoy these
moments of the journey cuz like once you
start to grow up a little bit, you will
look back and remember like those were
the days that were actually really cool.
No, it's it's the best. And I think it's
also like I've learned that you sort of
play mind games with yourself to stay
committed to something to force yourself
to do something. And one of the the
interesting things about being even live
and you you you've made a public
commitment to your people, to your
friends, to your family, that you're
doing this podcast, that you're
investing time in it, and people should
also care. And so the minute you stop
doing that, you sort of break this like
invisible contract that you have with
them. And so, you know, I think that
also is a thing where you're just like,
okay, I got to keep doing this. I got to
keep doing this. And I think that's that
goes for a lot of things. you know, how
can you set up tricks in your life to
say, "Okay, I I want to make sure I
mean, even me quitting my job and not
having another job is sort of a hack."
And having a place in New York and
knowing that that's expensive is sort of
a hack to be like, "Okay, Max, you got
to figure this out." Like, you need to
figure out how to make money. You need
to stay scrappy. You need to stay
humble. You need to be out there
grinding. And and I do feel that. And it
was like, yeah, I probably spent too
much on my place and do whatever else,
but like that forces me to get out of
bed and work out and stay active and
meet that person and do some things that
are easy to say, "Hey, I don't want to
do this." Yeah. But I think that's a
fair transition uh into saying that
you've kind of earned the right to be
able to like [ __ ] around and find out. I
mean, you've some of the things you've
done people will go through an entire
career having not done for better or for
worse, but like appreciate it. you we
can start with the the uh early Uber
experience because I think you probably
dealt with some movie like uh moments in
that journey. Um so you went from early
employee turned founder turned I guess
middle to late employee relative to the
scale of goof. Um so I that's something
I really want to jump into is like going
from not being in charge of the whole
thing to being in charge to not again.
But let's start back with the journey in
Uber. So you joined you were what
employee 25? Yeah, 25. I was 24 years
old. That's nuts. And there was only
probably 15 people at the company when I
started because, you know, they give out
the employee IDs, but people leave. So,
I was employee ID number 25. I mean,
there was Oh, interesting. There was
probably 15 people, maybe less at the
company when I started. And we were
Chicago was the fourth city. So it was
literally, you know, company launches in
San Francisco mid 2010, New York was in
the spring of 2011 and then August was
Seattle, September was Chicago, and I
joined in August to to get it going. How
did you end up at Uber? I hustled. It
was uh you know I so I was working in
consulting out of school. I graduated in
2009 from college and was working at
Accenture. It was great. Loved it. loved
the people I was working with, but it
was tough. I mean, it was corporate as
corporate gets. You know, I have a joke
in the podcast when I talk about this of
like I was wearing these like baggy
Banana Republic pants and like just
wasn't vibing. I mean, it was hard. It
was hard to conform. It was a great
training ground for me to just know,
hey, you got to go to this job every day
and show up and be presentable and not
act like an idiot. Uh, and then but I I
knew that was not I needed something
more entrepreneurial, more scrappy, more
hustle. I had done a lot of things
growing up that I didn't even realize
were entrepreneurial and scrappy. I
mean, you know, in college, I was
throwing parties and bar crawls and
tailgates. I was the Monster Energy
drink rep. You know, I was buying kegs
and selling tickets at the door. And
some of these things that I didn't even
realize were entrepreneurial and scrappy
and definitely skills I never thought
they would translate. They definitely
did not translate to
Accenture, but they directly translated
to Uber
2011 running around getting people to
sign up for the app, getting drivers to
download and and join and on board and
make money on the platform. And so, you
know, I whatever I read about Uber, I
heard about it, and then it was
basically a multi-month process to
convince them to hire me. And I got
turned down, you know, a few times
during that. Really? So, you got turned
down multiple times even though there
were only like give or take 15 to 20
people at any given moment. Yes. What
was it? I'm curious. What was the
strategy that you took that actually
worked? Like what was the moment in time
or what was the thing you did or the
person you talked to where they're
finally like, "All right, this guy's
relentless. Like, shut the [ __ ] up.
Here's your your employee ID. Like, now
it's time to work." So it was one thing
was they were asking me for projects
throughout which I think it's easy for
people to say, "Oh, I don't want to do
free work or whatever." But like look,
if we're being honest, whatever work
you're doing before you work at a
company is probably not that great.
Probably not actually using it for
anything. They really are trying to test
hustle, mental ability, u and mental
ability, I mean more just are you going
to be able to deal with the fact that
there's going to be a lot of ups and
downs. This is going to be hard. you're
going to be up against challenges that
you don't know how to solve and you have
to push through. It's not like there's a
training for being at a early stage
startup. I mean, yeah, maybe you've got
some skills, maybe you've done a few
things, but really it's a battle of can
you persevere? Can you keep showing up
every day? Can you hustle? Can you work
your ass off? Are you excited? Are you a
good person people want to be around, be
in the office with? I mean, that's kind
of the baseline training for the
earliest stage of a company. And so
that's a lot of, you know, what was
going on when during those months. And
then what happened was my mom actually
said, you know, why you you need to turn
the screws on them. Like you're the one
who's got a good job at a big
corporation. Turn the screws. Say you're
the one taking a risk. You're the one
taking a shot on them. And I sent a more
aggressive email than I had sent
previously. And the the guy who's
amazing, Ryan Graves, the man, responds
immediately and says, "I'm on the next
flight to Chicago. Let's hammer this
thing out." Um, so it was Mob. It was my
mom. Wow. Yeah. Well, I'm pumped. She'll
be my Mother's Day guest on the pod. So,
if you uh We're going to dive into it
together. I'm flying her out. We're
going to the studio. We're going to do a
Mother's Day podcast together. Wow.
Interesting. I've never actually thought
about bringing a family member on my
podcast. That's an interesting thought.
So, mom helps you get into Uber. You're
employee number 25. I mean, can you
speak a little bit to just like that
culture because I know a lot of 25
person companies, right? We're actually
26 people, so we're like in that that
range right now. And when you just think
about what Uber is today, like people
forget the fact that like most companies
started from one or two or three people
depending on how many founders there are
and you got to build brick by brick. But
like when you're at 25, I feel like
oftent times you can sense like this
one's different and like here's why.
What would you say looking back on that
experience like stood out to you is like
this is this is not your average
startup? Well, first I mean Travis was
the best. I mean Travis is the goat.
Travis Kellen founder and was the CEO of
Uber. I mean,
you I'll just I'll never forget watching
clips of him and and videos of him and,
you know, before I started, and I didn't
know who he was before I started the,
you know, interview process and looking
at Uber, but you knew he was special
even in clips. I mean, there's a there's
a a podcast of him and Jason Calcanis in
early August 2011, and Travis goes
through his vision, and it's and that at
that point, Uber was only black cars.
So, it's black cars only. It's high-end.
It's $15 minimum fair. And Travis is
already talking about a world in which
everyday drivers could be driving their
own vehicles in
Airbnb of transportation. And that was a
crazy thought in 2011. I mean, ride
sharing doesn't even come out until
2013. So, we're still two years before
this thing's really happening. This is
before Lyft. This is before Sidecar. and
Travis was just out there already on
this. And so I think, you know, for me,
probably two things. One is you get
there and you're in the mix with Travis
and you're immediately just the bar is
so high. You can, you know, this guy's
the best and just so smart and such a
hard worker and you just feed off his
energy. I mean, you're just so pumped. I
mean, you're just so pumped to be in the
room with him and that never waver. Uh
and then he just had such a clear vision
and it was
so simple for people to execute against
in the beginning which was
just we have a micro strategy in a city.
We stand up an operation in a city. It's
very local in a city. We get
drivers. We put them on. We pay them a
base minimum to make sure they're on the
road. We started with two drivers in
Chicago. So it's literally start, you
know, that in in that, you know, 15
years ago, call drivers in the yellow
pages, bring them by their professional
licensed chauffeers. You show them what
an iPhone is because again, it's 2011.
You give them that iPhone, which is
crazy. It's locked down to the Uber
driver app. They, you know, you convince
them, hey, press this button, you'll see
a little man on the screen and go drive
to that person and pick them up and take
them wherever they need to go, and we
promise we'll pay you at the end. And it
didn't even have, you know, routing in
the app. So, so what they'd switch to
like Google your destination? We didn't
put that even Oh, they what? They would
they would tell you where that you were
taking them. You literally just request
a car. You don't you tell them in person
where you're going. That was the
beginning. Was there a parameter? What
if you got in the car and you're like,
"Take me from Chicago to Atlanta." We
had some crazy stuff like that. And we
would see it because we had And drivers
would do it. Yeah. I mean, sometimes
they would call us and like check like,
"Hey, can I take this person to St.
Louis or whatever." Um, I mean, some of
it was fraud and other things, but uh,
yeah. Oh, yeah. We had we had wild
things. And almost immediately, you also
get stories like that. Hey, it's winter.
I'm at the airport in New York. My
flight's canceled. I'm trying to get to
a thing or Christmas or whatever. I need
to take it across a couple states.
Driver's down. Game on. Let it go. Um,
and that and that's like when you know
to the magic of product market fit and
this thing's working and you see it out
there and those types of connections are
happening. But I mean the first they
didn't even have an app to start. It was
just texting. You would just text in and
the you know you text your address where
you are and the driver would come to
you. And that's where I think people
also don't
understand how simple the beginning of
something can be. You know, and even
something as crazy and massive and
successful as Uber is, it started as,
you know, a little SMS,
Twilio text to get someone to come and
pick me up. Yeah. Yeah, I think that's
probably one of the biggest learnings
I've had on my short founder journey
thus far is like the misconception
around how crucial it can be to just
figure out the cheapest and fastest path
to like testing a concept that can
become so much more sophisticated later
on. But like I think um I think it was
the Bark Box story. I might have talked
about this once on the pod a long time
ago. Do you know how Barkbox started?
No, I don't. It's like the founders went
to Washington Square Park and were like
talking to dog owners and just like,
"Hey, like would you buy like if I sent
you a box of toys and treats every
month, like would you pay for that?"
Yeah. Like what would you what would you
want in it to make you pay whatever?
They just like literally talked to a
bunch of people like went back to the
drawing board, did a bunch of research,
went back to the park with a more
formulated thought, did the same thing,
and then were like, "All right, like put
your money where your mouth is." like
walked around with like a little stripe
machine and got like their first
thousand subscribers like hand tohand
combat before they ever like sold an
actual physical box of goods to someone.
Amazing. Which is like the epitome of
this. Like I'm I don't know if I got
that 100% accurate, but it's the message
the through line of like validating that
idea um before like raising a bunch of
money and doing all sorts of crazy [ __ ]
with it, which I think is another issue
that we could probably Yeah. talk about
in building in doing all these things
that you don't even know if they're
they're going to work. And I say to
people all the time, can you do this on
text? Can you do this on email? Can you
do this on WhatsApp? Like what what are
the things ways that you can hack
something to just see if there's any
signal before? Why are you building
something if you don't know if there's
signal? Yeah, it's uh my my philosophy
with that is like raise money or put
resources against something to double
down on solutions instead of to try to
solve a problem. If you can solve it at
a micro level, there's probably
opportunity to solve it at a much larger
scale. Absolutely. Um, another thing I
want to talk about which I was joking
when I said he's a struggling podcast
host is just that he's early in his
journey, but I think you are shedding
light on a really interesting concept
with the early podcast which is around
talking to early employees at companies,
right? A lot of early employees at
companies go on oftentimes either become
founders of their own or like ride that
journey and become like an integral part
and make a shitload of money doing it
like at successful businesses. Um,
something I'm curious about from your
perspective, having done what you've
done in your eyes, like what separates
good from great in terms of talent
because like those first couple hires
that you make are just like so
important. I think there's an element of
like the entrepreneur, someone who like
you think has that gene to be a founder
one day but maybe isn't there yet. And
even just like learning about what your
podcast is about and your journey. I was
thinking about like who are those people
to me in my company where I'm kind of
like holy [ __ ] if they left tomorrow
like I would be really really upset
about it because they're absolute a
players. How are you f how do you think
about identifying those people? I
probably obviously there's no perfect
framework but I probably tend to go
slightly more junior slightly more
inexperienced because and ideally have
some sort of chip on their shoulder. You
can't necessarily find the chip on the
shoulder during the interview interview
process, but that's sort of like a win
when you do find that person. But I
think ideally someone who's more
moldable, more scrappy, more kind of
game for anything. I mean, you really
want someone you can throw into the deep
end and they're down for whatever. And
you know, I think one of the beauties of
the early days of Uber was there was a
lot of people that were down and like
look, the numbers are going like this.
So you get the benefit of if you're
growing and it's exciting and it's fun,
people are willing to do a lot more
things than they might be willing to do
if they thought the company was tanking
and doing worse and and whatever. So you
definitely benefit from a company
succeeding. But I'm looking for people
that are scrappy but have talent and are
positive and just going to like kind of
throw themselves into things and and
stick through it. And I think not
always, but sometimes people with more
education and more credentials and more
experience tend to be people that maybe
it's harder for them to deal with the
chaos of a startup. It's harder for them
to deal with, wait, I don't have the
title that I thought I would have at
this point or my parents promised me I
would have if I took that class and met
with that tutor. And so, and like look,
that's that's me, right? I mean, I'm not
someone who's overly credentialed or
overly educated or whatever. And, you
know, neither of my parents, you know,
have a college degree. I mean, it's it's
more um, you know, I think for me, I'm I
come from a more kind of scrappy
environment. And so, maybe that's, you
know, me also kind of seeing myself, I
think, in in people that I gravitate
towards. What does that look like on a
tactical level? Like, are there
questions you're asking in interviews?
Are there just like uh qualitative
activities that you're doing with people
to just gauge like how they behave? I'm
curious because I think uh hiring and
identifying talent is something that's
so important to me because I've learned
over the last three years of building my
company that at the end of the day like
the thing that a CEO needs to be best at
is like identifying the right talent or
knowing who the people are that can help
you identify the right talent because at
the end of the day you just need to find
people who are better than you at
something because your time becomes
limited as you're trying to do a lot.
So, I've been like hyper obsessed with
just continuing to hone in on like how
do you sift through noise to like find a
players?
It's like almost like controversial at
this point and I've gotten a few uh
glass door negative reviews. I love
this. Hit me and now I'm interested. I
mean, uh you definitely want to put
people through the ring a bit. Max is
like, "Me at 3:00 a.m. We're going for a
12mi run. I'll see you." I mean, that's
the thing because I do hear the extreme
and it's not that. But I want to test
you a bit if I can within reason. I
mean, I'm probably going to be Give me
details. I want like the like the
interview. I'm probably going to be sort
of a prick. Like I'm going to be
dismissive. I'm going to push back. I
might be a little loud. I might ask you
some weird questions. Nothing like
creepy, but like Yeah. I I I first of
all, I want to know more about your
background. Like why are why are you
like how you are? How did you get to
sitting with me today? Where are you
from? what you know, again, you're not
gonna be able to sus all this out in
interviews, but if you and I were just
having a drink and I wanted to get to
know you better, like, I want to know
where your parents are from. I want to
know what your parents did. I want to
know where you went to school. I want to
know one of the hardest things you had
to deal with growing up. I want to know
what your career has been like. What are
the tough things that you struggled
with? What are what are the times that
life didn't meet your expectations? How
did you react? How do you feel about
that in retrospect? I mean, I I I don't
want to know about the good stuff. I
don't want you to sit down in the
interview and say, "Let me tell you
about myself." I say, "I don't No, stop.
Stop. Don't I don't want to know your
script. I'm going to ask you some
questions." Like, I don't want to know
what your version of the events are.
We'll get to that, but I want to sus
that out and I want you to do something
ideally. I want you to put together a
project or go bring me a lead or go
identify who you would target or come
work with me for a couple months or a
couple weeks. Come be an intern. I mean,
I at GoPuff, I had like four or five
adult interns, and I feel bad calling
them interns because they were like in
their late 20s or early 30s, but we did
it in a more trial way. And they were
all rock stars. They were like, "Screw
it. I do want this job. I do want to
work here. I do believe in the
opportunity." And like, look, I'm not
saying it in a demeaning way. I'm
saying, "Look, I believe in you. I just
don't necessarily have a spot. or look,
for these reasons, I just can't bring
you on full-time or I need you to kind
of prove yourself a bit. I'm not going
to treat you bad. I'm not going to
anything else. I'm actually I want you
to succeed, but I need to see it. And a
lot of times those people just rip
because then they have a chip on their
shoulder. You see the chip and they
don't want the title intern and they do
feel like they've done something in
their past and they do feel like there's
something to step up towards. And so,
you know, again, it doesn't always work
like that. You can still piss some
people off. you can accidentally be
meaner to someone that you mean or
whatever else. But when that sweet spot
and that's kind of what they did at Uber
to me and a lot of people, not
necessarily purposefully, but like they
sort of tried to see, are you a culture
fit? You know what your culture is? You
have to figure out how do I then put
someone through whatever puzzle to see
if they're going to fit this culture
because if someone's not a culture fit,
it is never going to work out. Yeah. And
I've I've learned that the hard way with
a handful of people. It's like you can
have all the credentials, but like
certain businesses are built certain
ways and you need to be able to like fit
in or not. The the Go Puff guys, there's
a a ton that I just, you know, love and
respect about Rafnik here. I think one
of the things I really learned from them
was the culture piece of just look,
they're big family guys. They're very
supportive. they're going to um you know
ingratiate you and you know be kind and
and whatever else, but ultimately it's
their company. It's their culture
they're trying to build. Again, they're
collaborative. They're great. I was in
those meetings with them. We were trying
to figure out a bunch of things, but at
the end of the day, it's their culture
and it is their company and it is their
vision and it should be. And they of
course they they shapeshifted and and
and evolved and whatever else, but you
know they also tried to be clear about
what their principles were and make sure
that people fit into their puzzle and
and it again there's there's back and
forth on that and it has to work right
but like that's right. And when I talk
to entrepreneurs now it's like well
you're trying to be open for everybody
and this and that. It's like that's too
much. Like what is the thing you're
trying to build? What is your vision? be
clear on it and find people that fit
into that. Again, it's going to evolve.
It's not that it's it's totally black
and white, but it needs to still be your
thing. And if people aren't going to fit
into that, they're going to likely not
work out. Yeah, you actually So, you
bring up something interesting I want to
talk about for people who are listening
and don't know this. I was at the bottom
of that totem pole at Go Puff. at the
bottom. Not at the bottom, but pretty
low to the bottom on the on like within
one team at the I think I was like the
first BD associate or whatever the
madeup title was at the time. Um, and
got to like see firsthand. That was like
my first exposure at a company that was,
you know, moving at that pace, had
raised that amount of money, had that
many like heavy hitters around the
around the table. And I think, look, I I
definitely felt like I brought a couple
unique ideas to the table, but at the
end of the day, like it's really you got
to like know your role. Uh, and yeah,
it's important like don't take no for an
answer and recognize that like you can
create you you create your own luck by
like doing things adding value, whatever
it might be. Um, but it was a lot of
like sitting around and seeing what
others are doing to like understand what
it takes like operate at the next level.
Cuz if there's one thing I've learned
from starting my own company, there are
levels to this game where like you think
you're doing something cool and then you
see how other companies are operating
and you're like, "Holy [ __ ] like
they're just thinking about problems in
a way that I just didn't even know
existed." Uh, which brings me to my next
question. You have like sat at the table
in some of the like most highstakes
conversations. I mean, you were the
chief of staff to founders of a company
that have raised what $4 billion, right?
Like it's like hard to fathom the amount
of zeros at the end of like these
numbers that you're looking at on like a
P&L. What is it like having those
conversations when the stakes are that
much higher compared to maybe like other
situations you've been in? Because
honestly, you're shedding a light and
giving a lens to the people listening to
this that I don't think we've had before
of like you're sitting in a room with
the founders of a company worth billions
of dollars with investors who've
deployed nine figures into this company
having to like make decisions and have
hard conversations. Like walk through
the framework around that a little bit
because I just think that's experience
that you can't you can't really like
read
about, you know. I think well one thing
is imposttor syndrome or whatever you
want to say you know there's like if
you're like what's something you would
tell your younger self it's like you
always think you don't know what you're
doing like you're always you're and you
should be putting yourself in situations
where you are beyond what where you
think your skis are right where you
think oh man I've pushed myself again I
can't believe I'm in this room I can't
believe I'm in this situation I don't
have the experience experience for this,
you know. So, I think it's a bit of you
should be pushing yourself to be in
those environments. And that's a good
thing. It's good to still feel the I
don't know if I know how to help in this
situation, but so I think some of it's
balancing the humility, knowing your
place a bit, which is I'm here to help
facilitate this conversation. I'm not
the main person, but that's okay. I can
still make a big impact. And honestly, a
lot of times it's better to be a
secondary player and still make an
impact and be in the mix and stay in the
room. Um, and then I think it's, yeah,
how do you just lean on your experience
enough to know, okay, you know, I might
not know this thing we're discussing
exactly, so maybe I sit back on it, but
like this thing, I do have something
that I saw before that mirrors this. And
maybe it's not even advice as much as
it's, hey, look, this thing we're
discussing, I saw this before at Uber. I
saw this before when I had my own
company. This is how it played out for
us. I'm not saying it's an equivalent
situation, but it's damn near close. And
this is how this played out. So, can we
all just agree maybe we should think
about this a bit differently if we think
that this piece is true? And so it's
it's like how do you influence more than
you say, more than you tell? And how do
you influence on the right things?
Because when you're lucky enough to find
yourself in these rooms or these
situations, you want to stay in the
room. And you only have so many bullets
or whatever to be able to deploy to say,
"Hey, I think I might be kind of right
or I have an example on this thing." So,
look, it's it's it's a balance um in
something that, you know, I mean, I
worked for Emil Michael, who's
unbelievable, and you know, was was
number two to Travis at Uber, and I saw
him play, you know, one of the best
number two jobs ever. And and it it
inspired me in a lot of ways of, okay,
you don't need to be the number one
person. You don't need to be the
founder. And that's kind of what the
podcast is about, too. It's just like
being an employee is awesome, too. you
could still rise the ranks and be in
these interesting meetings and be in
these rooms and make a big influence and
not be the founder. And I think it's
just it's so it's like a misnomer at
this point that you have to start
things. There are so many early
employees that make handover fist more
money and accumulate more accolades than
like majority of founders. Yes. Right.
Like and that's actually really
underestimated. I think there's a piece
of ego involved in that as to like why
there's probably people starting things
that maybe shouldn't be. Um there's a
piece of it where you're starting
something that doesn't actually have
legs, but you don't want to give it up,
so you end up doing it versus some
people who find themselves in a
situation of being an early employee at
some companies that go on. I mean the
look at what just happened with Nvidia.
I think wasn't it like a thousand
employee? I don't know the number. I
think it was something like a thousand
employees made like over half a million
dollars. So something like hard to even
like comprehend. Yeah. And even if it's
not financial, I mean, just some of my
best friends in the world are people
that I've worked with. And so, you know,
just from an experience standpoint, even
if the monetary
rewards aren't
outsized, the personal rewards certainly
are, right? I mean, you know, you're in
the trenches with people. You're in day
in day out. I mean, I love everyone I've
worked with. Even if they're people that
were dicks to me or whatever or would
like you still have these these bonds,
right? I mean, you know, I'm, you know,
so I think it's that's something where
it's I don't I don't I don't sort of get
the culture of everybody's got to start
things and do this and solo entrepreneur
and blah like all this entrepreneurial
stuff and like look, I still respect it.
I did start something. We did have a
successful exit. So, I get it, but man,
working in a company has been awesome,
too. And and unbelievable experience
that I wouldn't give up for anything. I
want to talk about that, though. You
You're so humble about it. you left Uber
start maybe had some stops along the way
and started started Bandit. Uh I want to
understand two things. The first one is
like what was the moment in time at Uber
where you were like all right like I'm
ready to go off and do my own thing and
then the second one was how did you land
on Bandit?
You know I think so Travis left and
whatever in mid 2017. So that was that
was a in a left and that was tough. I
mean, I was definitely tied to those
guys in a lot of ways and and it was
tough when they when they left the
company. So, I ended up sticking around
like another 12 months after they
departed, but it was a different
company. It was it was clearly Uber the
corporation now, not Uber the startup.
And that's great. I mean, DAR is the
man. I know some of the leadership team
over there. They're awesome. Like, more
power to them. I think though I was
like, eh, this probably is not no longer
my thing. thing and like look I like
earlier more you know I think I thought
that at the time and I and I still
believe that that's correct. Um and then
I think you know I left with a little
bit of a chip on my shoulder like I you
know I left with
okay I was really lucky to get this job
at Uber again. I worked my ass off to
get it. I was really lucky though to be
here make the money I did you know the
success that that we all had and but I
wanted to kind of prove it again. Uh,
and so I I thought about doing, you
know, working somewhere else, but then
it was also so hard to recreate that
magic. And that's, you know, I find that
in a lot of people that have been on a
rocket ship like Uber and left. It's
hard to catch the high again. It's hard
when you kind of are, you know, in some
ways on a peak and you're trying to find
it again. It's tough. There's not a lot
of Ubers. There's not a lot of those
experiences. And so that was also where
I was like, all right, I'm not going to
recreate this by working another company
right now. um maybe starting something
is the move. And then with Bandit, it
was uh you know, we saw what was
happening in China with Luck and Coffee.
They're basically I just give a quick
two seconds on what Bandit was. Yeah. So
Bandit was a uh sort of digitally
native, you would say, uh coffee shop.
So we were app only before anyone was
appeas 2019. So app only coffee shop.
You walk in, it's still a normal coffee
shop, but you have to use our app to to
order and purchase, which again was a
big deal in 2018, 2019. And then the
infrastructure was modular and more
mobile, so we could move it around. So
we were doing revenue share deals with
landlords where we could just drop the
coffee shop into place and only took us
a few hours to set it up. And then we
would do a revenue share deal. And so we
were doing these in like office building
lobbies and white box, you know, retail
real estate in a way of doing this in a
way that um was scrappier and we could
move it around and, you know, didn't
require all of the uh upfront costs that
a normal kind of brickandmortar
restaurant would cost. So that was that
was banned. We ended up having four or
five locations in the New York area and
then three locations down in Austin
before we got acquired. Can you walk
through that journey of getting
acquired? I think um you know we've had
a couple founders on here who've sold
businesses but I've never actually gone
deep on like the moment in time where
you're like wait I think I'm going to
sell this company to like who are the
potential buyers to wait they actually
just told me they're going to do it. Oh
man it was crazy.
I So I mean if you think about it was a
very condensed timeline for us overall
from start to finish. Uh, you know, we
March 2020, we've got three locations in
New York. They're humming. The newest
location we just opened like a month
prior and it was doing like three, four
grand a day in sales, which is pretty
good for the one in New York. Yeah. The
second one because we had closed ones.
It was basically our our next location.
So, we had two active at that time. We
had opened three and the third one was
Hum. We launched food. It was in a good
building. People were in the office
every day. It was humming. And you know,
we're honestly we had raised, you know,
almost four million bucks from investors
like, "All right, we didn't know what we
were doing and a million mistakes and
James, my co-founder, is the best." And,
you know, we were having fun, but it was
crazy. We're trying to figure it out.
And then CO hits and then New York shuts
down. You know, we were literally
meeting with investors Wednesday night.
Do we do another raise? How do we launch
more of these? is how do we sort of
playbook this to you know because the
idea was we want to launch a bunch of
coffee shops and then COVID hits the
city shuts
down no one's going back into an office
we know now for years and so we just
shut the business down and then within a
few weeks we were like all right we can
either give whatever money we have back
to investors or we can relocate relocate
the business to somewhere else that's
warm in like a Republican city so maybe
there's less
restrictions going to Texas. Yeah. So,
it was like screw it, we're going to
Austin. And uh we reopened in July in
Austin. It was awesome. I mean, Sam
Doyle, the man, Ron, like these guys,
you know, flew down with us. We flew
down to Austin.
We found real estate. Wait, I actually
didn't know that's what happened. I That
was a complete joke when I said we're
going to Texas. Oh, no. No. We're going
It was literally like cuz you said warm
weather Republican. I'm like, well,
that's kind of like option number one.
Yeah. And again, it was like kind of pre
even knowing what was going on with the
world at that time. Yeah. Yeah. It was
like Nashville,
Phoenix, Dallas, Houston, Austin, Miami.
You know, Miami is weird because like
culturally we were like, I don't know if
we can figure it out there. Austin's
cool, but still Texas. Um, so yeah, we
went to Austin, flew a couple guys down.
They were kind of our launchers to
figure it out. And then by July 1st, we
were all there. And uh, we launched the
food trucks. you could request our food
truck to come to your neighborhood and
we would give, you know, sell coffee off
of it. And we launched an actual retail
location pretty quickly. And we just
moved that infrastructure. So we moved
it from New York down to Austin. Again,
white box the real estate, drop it in,
and you got a coffee shop. We built an
Airstream trailer. I mean, all in a
pretty quick timeline. What happened was
I knew some people that had joined
Gouff. We were in desperate mode. I was
just like, I'll do anything with anybody
right now. like, "Hey, go puff. Do you
want to sell coffee beans that we could
brand as Bandit? Do you want?" And then
it was like, "We don't want to do that,
but maybe we would do you could put your
truck in our parking lot and sell items
on our menu." Like, all right. And then
it kind of escalated from there where
they're like, you know, screw it. What
if we just bought you guys and you ran
that whole operation for us? We want to
get into food. We want to get into
coffee. And for us at that point, you
know, it was tough to see a path
forward. I mean, I still believe that we
could have figured it out. Still
trusted, you know, what we were doing.
We still had money in the bank. But it's
tough. You go from riding high in New
York shutting down, reopening, you know,
all the issues of changing cities and
whatever else. I mean, to to find maybe
a successful off-ramp was like,
hallelujah. Oh my god. Please, please,
please, let's make this happen and make
our investors whole. I mean, just the
whole thing. It was it was unbelievable.
And so when it was done and like it was
tough. I mean there was a time where we
thought the deal was dead. Um you know
but when can you can you walk through
that? I mean you obviously have to go
into extreme detail to the point where
like I probably shouldn't be sharing
this but I I want to get as close to
like the reality of that as possible
because I feel like that's the that's
the thing I'm curious about. So we the
first thing we were going to do is this
trial with them. we were going to put
the truck in the parking lot and sell
the coffee on their app. And then, you
know, we were apprehensive to do that
because we didn't know if it was going
to succeed. And I think at that point,
you you hit a point where you're like,
all right, this is a sick partnership
opportunity. Then you hit a point where
you're like, [ __ ] they could buy us.
And then you're like, that's crazy. Then
you're like, wait, no, they actually
might buy us. So then you have to have a
conversation of well do we even do this
trial because if we do the trial and it
doesn't go well it may be way less
likely that they buy us like it might be
a zero and I think it will go well but
you know you start to look at data you
start to project some things out you're
like [ __ ] like maybe we lean harder what
what are you trying to optimize for you
gota stop and ask yourself that a lot of
times right wait hold on a second we're
jumbled up we've been working on this
thing for a bit what are we trying to
optimize for and then you're like I
think we're actually optimizing for
getting acquired. I think that's a
better outcome and I think a better
outcome for them too. um because they
had a team working on it and it wasn't
getting off the ground and we started
working with that team and I remember
calling Dan Folkman the man who was
running the deal on the other side and
being like hey I don't know I think
we're going to hold our end of the
bargain or the partnership but I don't
know if they're going to you know these
guys that you've got there and that and
again it was that was real and you know
I think look I mean people know me I
mean I wasn't you know none of it was
was BSSE right we and we had similar
investors and stuff so it was all you
know everybody was trying to do the
right thing by each other and then they
sort of look into it and they're like,
"Yeah, you're right." Like, we don't
know if these are the guys to execute.
Um, and then, you know, so you start to
try and position, okay, let's actually
try and position this thing for an
acquisition path versus a partnership
path. And then from there, you know, was
there a moment in time where you
actually were the one that initiated
like that literal conversation to
someone at Gooff where you're like,
"Look, I know we're doing this
partnership, but like do you guys have
interest in buying us?" Is that like
actually the conversation? starts to
come at least I think this is probably
how it goes some it almost starts to
come up as a joke or like offh hand
right like you know maybe we just buy
you guys you're like yeah yeah maybe and
you're like okay but really you know
it's almost like dating or something too
where you're like okay well now how do I
not act desperate you know getting on my
knees and begging you right now probably
is not right the reaction but okay and
you're like I guess I got to like play
it cool like yeah I don't know maybe
maybe we'd be down you And so like it
kind of starts more casual like that and
then it's like all of a sudden we're
doing diligence and talking to lawyers
and um you know I talked to my lead
advisor investor uh and you know he was
like this seems like a no-brainer if we
can figure it out. Um and then you know
I think we had the you know we were like
do we do we go try and get a competitive
offer? But then we made the decision
like not to mess around like we knew
these guys we trusted them. I think they
trusted us. We had really good
interactions with the founders. It was
like, let's not let's not mess around
here. Let's not play play any games.
Let's try and figure out. So, we had a
deal in place kind of. It kind of fell
through. So, we thought the deal was
dead and then we had to, you know,
revive it, change a couple things, and
then, you know, we felt good about it,
and then it was, you know, came
together.
What was that that uh journey like for
you going from early employee to the man
in charge back to employee? Like was
there was there a moment where like the
you had to like reframe your approach to
like every day because now you're like
reporting to someone. I mean dude I was
so thankful to start that it was just
like this is salvation. Like you know
you just go from
Friday at 3:00 and you're like you know
can we pay for this thing? Can we not
pay for this thing? I'm not paying
myself. You
know, this is hard. How are we going to
do this? We're having an issue. Someone
just quit. We have to fire this person.
You know, sales were down yesterday
to, oh my god, we're like safe. This
part of the journey is over. I mean, it
didn't feel job mission accomplished,
but it just felt like, wow, a bunch of
the things that were stressors yesterday
are not stressors today. And that was
just a feeling I'll never forget. And so
I think from that standpoint, I was so
thankful to just be there. And then it
was cool
because we had resources. They wanted me
to build. They wanted to to fund that.
They wanted us to grow. And I was kind
of back in my Uber seat a bit except a
couple years older, hopefully a couple
years more mature, hopefully a little
bit more humble and whatever else. and a
fresh start to be like, "Okay, how do I
want to do this the second time around?"
Doesn't mean you still make a million
mistakes and whatever else, but it was
like, "This is cool. I actually I'm good
as an as an employee. I think I am. And
I'm good at like figuring out how to
shape shift a bit and like running my
mouth to a point and finding the line,
maybe stepping over it a bit, but like
staying behind it and trying to add
value, whatever else." And so, I think
that's part of also why when the podcast
came together, it was like I think being
an employee is awesome. And I think
people aren't out there talking about
how great it was. And I had the
experience
of we start something and it was great.
I loved having Bandit. I loved being
with my co-founder, but also getting
back to Gopuff with those guys and a
little bit less stress on that level, a
little existential stress. And being
back in the driver seat of growing and
building again was like this is great.
And you were that like you made this
comment earlier like when I left Uber, I
didn't know if I'd ever get a chance to
like be on this rocket ship again. And
it's like you kind of found yourself
back in the same seat, ironically
enough, with a lot of the same people.
Ironically enough, with a bunch of the
same people, which again shows you how
your network is everything and how the
people that you meet throughout your
career, you end up sitting with them
recording a podcast years later, right?
You don't know where any of these things
are going to go. So, it's just like
curate your friendships, curate these
relationships, keep growing, keep
building, try and stay humble, keep
doing stuff. And yeah, then all of a
sudden you're back. I'm back in the seat
again. You're like, "God, I can't
believe how all this comes around. I
can't believe how all this works. This
is awesome." And it was just a lot of
positive and then you just rip it and
you just see what see what happens. One
other thing I wanted to talk about with
you because you've been like front row
seat for this is just the concept of
fundraising. I mean, you've arguably
been exposed to some of the best
fundraisers in the world of startups as
we know it today. I mean, between Uber
and Gouff, I don't even know how many
zeros are are included in the amount of
dollars raised. And not to say that I
mean, we know for sure not every
business needs to do that, but for those
who do, like they could probably learn a
thing or two from what you've seen on
like what a good fundraiser does versus
a bad. Having had a front row seat to
people who've raised like hundreds of
millions and billions of dollars, like
what are your biggest takeaways or
learnings? I mean, momentum is
everything. You got to ride the wave.
you know, you you think you've got the
magic and the magic goes away. So,
you've got to take a take advantage of
every opportunity. I mean, look, you
want to be obviously there's some
balance there. You want you don't want
to over raise. You don't want to, you
know, raise incorrectly and whatever
else, but like if you feel like you've
got some momentum and people are
interested, you should take advantage of
those moments because I've seen the ups
and downs. I've seen you're on the come
up, people are pumped. I mean, even on
the bandit at the small scale that we
were at, when we had momentum and there
was some FOMO and whatever else, you can
raise and you can you can create FOMO
and you can get people excited, you can
take advantage of it, but the minute
it's gone, it's very hard to recapture.
So, you got to seize the opportunity
when you have it. And then I think it's
like, you know, some of the process
stuff of actually running a real
fundraising process, actually having
data rooms and decks and things and
teasers and whatever else and curating
your list of people and and saying we're
going to do this over a multi-week
process and we're going to do upfront
meetings and then elevate to the next
thing and then elevate to the last round
and we're going to make a decision by
this last date. Again, some of these are
champagne problems. Some of these are
harder to do in in in tougher
environments or whatever else, but you
that allows you to create some FOMO,
create some intrigue. These investors
talk, they know what each other are
doing. You have one person pass, someone
else is going to know they passed. That
might lose a second person. So, you just
you want to have some structure to these
things. And you don't necessarily want
to dabble in it when you're not
fundraising. Like, you're either
fundraising or you're not fundraising.
And you can really screw yourself if you
start to dabble in some of these
conversations before you're ready for
it. Especially at the institutional
level. I think like with earlier stage
companies, you know, with us, for
example, like we raise on a safe, it's
like if you come across an interesting
angel investor who like can bring a
unique lens to it. It's like we're not
fundraising, but will I make room for
you? Like yeah, probably. It probably
makes sense for my business. Um, but
yeah, I've always just wondered like how
the calculus changes in these in the
optics of these conversations when
you're raising like a million versus 5
million versus 500 million. Um, because
I do think the the the narrative is
definitely different and like the antics
you have to use for better worse cannot
be the same for someone trying to get a
million dollars versus $500 million.
Well, but that also just comes back to
the relationship piece is so important.
I mean, I saw that with Emil at Uber and
with um you know, Cameron who ran
Corpdev at Uber and uh the Rafikir at at
Go Puff, Dan at Gou. I mean, these guys
are actively having conversations with
investors, you know, again, the the
appropriate ones, not necessarily, hey,
outright we're raising right now or like
but curating these relationships,
teasing out enough info. It's much more
of a personal relationship at that point
when you're raising those those massive
dollars. And all those guys who are who
are some of the best fundraisers in the
world are are great and they're real and
those are real relationships. I mean,
it's not like they're playing a game. I
mean, those people care about people and
and are best in the world at it. What
advice would you give to someone who
maybe doesn't feel like a founder, but
wants to like start something great? Oh,
man. Well, I'd go work somewhere. I'd go
be an employee somewhere. I go work in
the early stage. I think that I mean
that's what I'm trying to do with the
pot is like bring back make startups
great again. Like make make working
early stage great again. I would my
advice would be find a list of five 10
companies that you think are just cool.
Like I just thought Uber was
cool. You like did you know anything? I
was 24 and I'm like from Chicago. Like I
you're lucky that I was able to tie my
shoes. Like I just thought it was cool,
right? I just wanted to run around
Chicago and tell everyone to use a black
car service that they could request
through their phone. I was just pumped
about that. I'm a promoter and I think
so you make a list of 10 companies that
you're pumped about and figure out how
you can add value and try and get a hold
of a founder or an employee or anybody
there and try and get in the mix. And
even if it's like you're working a sales
job, you feel like you don't have a lot
of time like I don't know, can you give
somebody five 10 hours a week? Can you
bring so many leads? Can you do some
thing? I just think if you want to do
something entrepreneurial and early
stage, the best way to get in the mix on
it is join something early, join
something cool, build your network, meet
interesting people, and and your world's
going to explode in a good way. Looking
back on your journey, what would you say
is the biggest Turning Pro moment that
you've had along the way? That moment
where you feel like everything just
changed and you were playing a different
game.
I mean, I
think I mean, joining Uber was insane.
Joining Uber was insane. It definitely
felt I couldn't believe, you know, as
you ask what's my advice for someone
trying to figure it
out. I just you start probably thinking
about your future when you're 16, 17,
but so much is kind of decided for you,
right? Like your where you are at that
point is decided for you. where you're
going to go to college and some of those
things. Yeah, you've got some of but you
have barely any you don't even know what
you want to do at that point. You don't
know where you want to be. You don't
really know who you are. And then all of
a sudden, you're like 22 and you emerge
from college, this construct that we've
developed. And now you like still don't
know where you want to do or what you
want to be. You're just probably in debt
and like whatever else. And I think for
me, the fact that a couple years out of
school where I still didn't know who I
was or what I wanted to do, I was able
to find myself in a situation where I
was just so pumped. And it was like,
wait, these people are more like me than
other people I've met, and their values
are more like mine that I didn't even
know I had these values. But like, you
start to piece together and you're like,
wait, this I know this. I don't know it,
but I kind of know this game a bit. And
I feel like I can learn this game. And
that's why I just push on people that
are trying to figure things out or
earlier in their career or whatever else
to just like just get in the mix,
experience new things, try new things
because you just don't know which part's
going to sort of pull you in. And if you
are lucky enough to find that, then you
just keep going down that rabbit hole.
And so I think for me, probably joining
Uber was a huge moment, huge turning pro
moment. And then probably the the bandit
to go puff where you were like, "Holy
[ __ ] like I can't believe I have the
privilege to be able to do this again
and like let's make the most of this
experience and I'll do it until it's no
longer a thing." And then when it's not,
I'll be sitting here with you and like
all right, how do we figure out what the
next thing is? Max, this has been
awesome. I appreciate you coming on
today, dude. Thanks for having me. You
want to look at that camera and let
everyone know where they can find the
early pod?
Earlypod.com on Instagram. Early Pod on
Tik Tok. Early Pod and we are on
Spotify, Apple, YouTube. Early podcast.
Subscribe, please. Hell yeah, dude.
You're the man. Thank you so much.
Appreciate it.
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