0:00 Let's start back with the journey in
0:01 Uber. So you joined, you were what?
0:02 Employee 25. Yeah, 25. I was 24 years
0:05 old. That's nuts. And there was only
0:07 probably 15 people at the company when I
0:09 started because you know they give out
0:11 the employee IDs which people leave. So
0:13 I was employee ID number 25. I mean
0:15 there was Oh, interesting. There was
0:17 probably 15 people maybe less at the
0:19 company when I started and we were
0:21 Chicago was the fourth city. So it was
0:24 literally, you know, company launches in
0:27 San Francisco mid 2010, New York was in
0:31 the spring of 2011, and then August was
0:34 Seattle, September was Chicago, and I
0:36 joined in August to to get it going. How
0:38 did you end up at Uber?
0:40 [Music]
0:44 Welcome back to season 4, episode two,
0:46 The Turning Procast. Today we have Max
0:48 Cwley, who's a struggling podcast host.
0:50 Thanks for joining us today, Max. Thank
0:52 you. Thank you. I appreciate it. Help me
0:54 get my name out there so I can such a
0:56 cool introduction for someone who has
0:57 sold a company, who has worked high up
0:59 at some of the biggest companies in the
1:01 world as we know it today. Uh so I think
1:03 it's a great way to like humble yourself
1:04 as you as you start on this new journey
1:06 as a podcast host. Thank you. Thank you.
1:08 I mean, you got to got to try and always
1:10 bring the ego back down as much as
1:12 possible. I mean, there's no better way
1:14 to do it than starting a podcast. I can
1:15 tell you that as someone who uh who was
1:17 there one day. Look, we're um I think
1:19 this is maybe episode like 77 or
1:22 something in that range. Way to go, man.
1:23 That's awesome. Which is crazy to think
1:26 about for sure because I mean I think we
1:29 talked about this, but the statistics of
1:31 podcasting, it's like the way the
1:32 industry or the concept is set up is
1:34 like you're designed to fail because
1:36 it's so [ __ ] hard to do and it
1:38 typically requires a lot of resources
1:40 and a lot of money and so most people
1:42 just like can't make it. But my
1:44 mentality with it is just that like the
1:46 number one fa way that you fail is just
1:48 by giving up. So if you could just stay
1:50 in the game long enough, hopefully, you
1:51 know, it turns into something. No, it's
1:53 funny as I've talked to people in the
1:55 industry and it's like what advice do
1:57 they give you? And then people are like,
1:58 "What's your goal with the podcast?" And
2:00 it's like, "My goal is to continue to do
2:02 it." Like, can I just literally put one
2:04 foot in front of the other, keep
2:06 recording, and as you said, good stuff's
2:09 going to happen. I'm going to meet
2:10 people. It'll be interesting
2:11 conversations. I'll whatever the thing
2:14 might be. But yeah, I mean it's very
2:17 easy a lot of the hardest things in my
2:19 life. I like right before you do it, you
2:21 say to yourself all the reasons that you
2:23 shouldn't do it. You start you start
2:25 thinking I don't want to do this. I
2:26 what's what are all the excuses that I
2:29 could have to not do this thing right
2:30 now? And if you just give yourself a
2:33 little bit of that push, it's where all
2:35 the the magic is made. So we'll in a few
2:38 minutes we'll go back to the beginning
2:39 of your journey because I think you have
2:40 a pretty crazy journey. But I actually
2:42 think the podcast thing is a very
2:44 interesting place to start because you
2:46 went from working in like the most high
2:48 growth chaotic environments uh arguably
2:51 in like startups as we know it for
2:53 people listening like early Uber sold a
2:56 company to go there through these crazy
2:58 trajectories at both companies and now
3:01 you're in this phase of doing something
3:03 that is a lot more slow. It's a lot
3:06 slower and a lot more there's a lot more
3:07 intentionality around it I think or you
3:09 have the privilege of that being the
3:10 case. What was that like mindset shift
3:12 for you after so many years of like in
3:14 the trenches that you're like I want to
3:16 try something that for all intents and
3:17 purposes from my perspective is so
3:19 vastly different. It's I mean look I
3:21 think one piece for me is I definitely
3:24 believe in reinventing yourself as much
3:26 as possible. So I I don't think I was
3:28 ever a person to do a 20 30 year sort of
3:32 corporate track and keep rising the
3:35 ladder and like I love that stuff. I
3:37 respect it. I've worked at amazing
3:38 companies that you know just for
3:40 whatever reason I I still stayed there
3:42 long periods of time in the scheme of of
3:44 how long people stay at companies these
3:46 days. But I think for me you know it's
3:48 part reinvention. So when I do something
3:51 new I want it to feel different. I want
3:53 the the success goals, the metrics to be
3:56 different. And so, you know, first piece
3:59 is just reinvention. And then I think
4:01 the second thing is look, it's a it's a
4:04 it's nice to be able to take time off
4:06 between jobs. I know that that's for the
4:09 most part a privileged uh thing that
4:11 I've had the ability to do. So, I'm
4:12 super thankful that I have had the
4:14 opportunity to take some time between
4:17 these various things that I've done. So,
4:19 you know, took some time after Uber,
4:20 took some, you know, joined Gouff,
4:23 taking some time now. But for me, taking
4:25 time is not just I'm laying on the couch
4:28 and chilling. It's actually, yes, I do a
4:31 hard reset. I try and travel. I try and
4:34 be mindful. I try and really reset my
4:36 brain, but then I'm back in grind mode.
4:40 So, this is a version of grind mode.
4:42 It's just it's just, you know, sort of
4:43 maybe triggering different parts of me.
4:45 I have a friend who I was with uh two
4:47 weeks ago. He was the CMO at a
4:50 billion-dollar brand that you're very
4:51 familiar with that I'll tell you off
4:53 record cuz I don't want to out him but
4:54 he was there for a long time left there
4:57 and for the last like seven months or so
5:00 has been on this like journey of like
5:02 finding himself again because his whole
5:03 thing was like for the first time in my
5:05 life I don't have a commitment where I
5:07 didn't have a significant other I didn't
5:08 have a dog I didn't have kids I didn't
5:09 have a house every moment of my life
5:11 went into this business and then the
5:13 second I stepped away from it I realized
5:15 like I had been running away from my own
5:17 thoughts and like sitting with myself
5:19 because it's so easy to distract
5:20 yourself which is doing work all day
5:22 every day when you're in a very
5:24 stressful fastmoving environment. I'm
5:27 curious from your perspective as someone
5:28 who's done this, like how do you what
5:31 are the things that you tell yourself or
5:32 the parameters that you set for yourself
5:34 after going from like allin 100 miles an
5:37 hour to like stepping back with no
5:39 responsibilities professionally at least
5:41 and uh having the discipline to not just
5:44 like jump into the next thing right away
5:46 because obviously the bigger things you
5:49 do the easier it is for you to get like
5:51 poached or more opportunities come your
5:53 way. So I'm curious to understand like
5:55 your own selft talk and that journey of
5:57 like actually forcing yourself to like
5:59 take a minute to breathe. For sure. I
6:01 mean look I'd like to say I was better
6:03 at the breathing piece but I'm trying to
6:05 like truly take the time. But I think
6:08 the the biggest thing for me is number
6:10 one still having the structure. So still
6:13 saying I'm going to try and get up as
6:14 early as possible. I'm still going to
6:16 try and go to the gym in the morning.
6:17 I'm still going to try and meet with a
6:19 bunch of people. you know, still have
6:20 the sort of day-to-day structure like I
6:23 am working in a way. It's not it's not
6:25 like I'm totally disconnected from
6:26 things. I'm still sending out emails and
6:29 doing cold outreach and still trying to
6:31 build the network and figure out what
6:32 people are doing. And so, you know, I
6:34 think for me, you know, again, it's not
6:35 like I'm getting up at bed, you know,
6:36 out of bed at 3:45 and whatever that
6:39 stupid meme is right now and throwing
6:40 water on my face. Saratoga spring water.
6:43 Yes. But I mean, you know, decently
6:46 trying to still be an adult and and take
6:49 the time and be appreciative for it. And
6:51 then I think for me being able to trial
6:55 things as much as possible has been a
6:58 big benefit. So, the podcast allows me
7:01 to still work a few day few hours a day
7:03 on something, still manage someone,
7:05 still meet a ton of people, hopefully
7:09 get smarter, learn something that I
7:10 didn't know before, but I'm kind of
7:12 dabbling in that. And I can also advise
7:15 a few founders, and I can also maybe
7:18 incubate something in a small way and
7:20 just test something else out there. And
7:21 maybe I can even do a job for a few
7:24 hours a week and start to see how that
7:26 goes. I mean, when I transitioned from
7:28 Uber, I took some time off first. I
7:31 traveled. I went to Asia and around the
7:33 world and like really tried to take some
7:34 time, did yoga retreats and maybe did
7:37 some mushrooms and like whatever else to
7:38 like try to reset. And then the next
7:42 phase was a lot of all right, I want to
7:44 meet with people. I want to figure out
7:45 what's going on. I want to learn as much
7:47 as possible. What are trens? What are
7:48 VCs investing in? What are things people
7:50 starting? What are startup studios
7:53 starting? You know, if you go talk to
7:54 one of those teams, they've got a list
7:56 of like a hundred ideas on the wall
7:57 they're thinking about. You'll see, you
7:59 go to studio to studio, you'll see a
8:00 theme in that and you're like, "All
8:01 right, this is what the market's working
8:03 on. This is what people are thinking
8:04 about." And then from there, you know, I
8:06 worked on a private jet startup for a
8:09 few months for a former co-founder of
8:12 Uber who just had another project that
8:14 he was working on and trying to do side
8:16 project, private jets. Um, and like
8:18 look, I love the company and I loved the
8:20 time, but it also was clear, okay, this
8:22 isn't a project that I want to work on
8:24 long term. I'm pumped that I met some
8:26 people. I'm pumped that I learned about
8:27 a new industry, but then that helps me
8:29 decide. I mean, I had a sperm banking
8:32 business that I was kind of incubating
8:34 and there ended up being a few of those.
8:36 And um, I still love the idea. And then
8:38 I decided to start a coffee company.
8:40 very desperate ideas, but you know, this
8:42 time and having some structure, not
8:44 crazy amount of structure, but some
8:46 structure to I'm gonna try something for
8:48 a bit. I'm gonna hopefully know when to
8:50 pull out so that I don't just get all in
8:53 on something I don't want to do. And
8:55 then that helps you. Okay, now a few
8:57 months in, I feel really comfortable
8:59 about the decision I'm making versus
9:01 jumping into something and then a couple
9:03 months being in being like, [ __ ] is
9:05 this maybe this isn't the thing I should
9:06 have done. What are the signals that
9:08 you're looking for when you're dabbling
9:10 in something to know if it's what you
9:11 should be doing long term or not? I
9:14 think I definitely want to be able to
9:17 see an impact in what I'm doing. And so
9:20 with the podcast, we can go to a bar
9:23 right now and I may be doing this
9:25 actively and say to the three people
9:27 sitting at the bar, "Hey, do you have
9:28 Spotify?" At which time they look at you
9:30 crosseyed and they're like, "Of course I
9:32 have Spotify." And then I say,
9:34 "Subscribe to the early podcast." Wow. I
9:36 love that. I'm not doing that enough. Oh
9:39 man, I am
9:40 that's because it's for me it's like all
9:43 right in the least I know I'm good at
9:45 that. So I made that that's valuable for
9:48 something. I mean my Spotify subscribers
9:50 are almost all handtohand combat. That's
9:53 so cool. Um and so I mean it was wild. I
9:56 was walking down the street with a buddy
9:57 and we saw a guy standing there and my
9:59 buddy goes, "Hey man, I used to live in
10:02 this building. Like which unit are you
10:04 in?" He's like, "I'm in this unit." And
10:05 my buddy's like, "I was in that unit."
10:07 Like, "How old are you?" And the guy's
10:08 like 25. And my buddy's like 50. And the
10:10 guy's like, he's like, "You're going to
10:11 make it one day." Like, "I was 25 living
10:13 in this building." And then I said to
10:15 him, "Subscribe to the early podcast."
10:17 And then I got a DM from the guy and he
10:19 was like, "That was so cool that I had
10:20 an interaction with your buddy. I'm
10:22 pumped listening to the pod. Loving it."
10:24 So, like I
10:27 it's I love to be able to control and
10:31 feel like the effort that I'm putting in
10:34 is getting real value. And as companies
10:36 get bigger, it's harder for that to be
10:39 the case. And that's probably why I've
10:40 gravitated towards things that are more
10:43 early stage, more fruits of your labor.
10:45 And again, look, anything that's worth
10:48 scaling, it's going to then be hard.
10:49 You're 77 episodes in, it's going to be
10:51 harder to get the random subscriber off
10:53 the street. you got other things to do,
10:55 but you know, I love that beginning
10:57 stage where you can feel that and then
11:00 also scale with, okay, now we get people
11:01 that do it and we build teams and
11:03 whatever else. But that's the part that
11:04 I I love. Yeah. But I actually think
11:07 that last point you made is important,
11:08 which is like you can't lose sight of
11:10 what got you to where you are. Like I
11:12 don't I think I have 77 episodes in the
11:15 bank, but there's no reason I haven't
11:16 told one person standing on a sidewalk
11:18 at a red light like, "Have you
11:19 subscribed to my podcast?" So I think
11:21 those are actually things I need to
11:22 start doing regardless. Look, I I don't
11:24 know. I think I have a thousand
11:25 subscribers on YouTube, which is like
11:27 not zero. Like, it's it's it's cool. The
11:30 way that I always someone said this to
11:32 me cuz on the spectrum of like viewers,
11:35 that's nothing. But if I said to you,
11:37 we're going to put all my subscribers
11:39 right in front of us like in the stands
11:41 to listen to our conversation. A
11:43 thousand people is like not zero. And
11:45 they haven't unsubscribed. And they
11:46 haven't unsubscribed. Like that's a real
11:48 Those are people that are fans. They've
11:50 subscribed. They're in. You should be
11:52 super proud of that. I mean, it's I am
11:54 partly inspired to do my thing because I
11:57 saw what you're doing. And, you know, I
11:59 think I the only reason I even hesitate
12:02 in saying that is because I want to be
12:04 able to actually come through with that,
12:06 right? I think a lot of people probably
12:07 say to you, oh, you're starting a
12:09 podcast. Everybody's got a podcast. He's
12:11 like, well, no, not everyone has a
12:13 podcast. A lot of people do or a lot of
12:15 people do or did, right? And so, it's
12:17 it's I'm inspired by what you've done
12:19 and now I want to be able to like meet
12:21 that bar, right? I want to be able to
12:22 meet that threshold and actually also
12:24 keep putting stuff out and and try and
12:27 make it a thing and not give up because
12:28 it's so easy to give up. Yeah, that's
12:30 the that's the biggest thing. I think
12:32 we've talked about this, but my my
12:34 philosophy around a podcast is how do
12:36 you optimize for consistency and not
12:38 virality? So if you think about like
12:39 what are the friction points or the drop
12:41 off points when you decide to quit, it's
12:44 like if you try to solve those pieces
12:46 first to just give you to reduce
12:48 friction to do it for a long time. That
12:51 to me is the the hack, right? Like
12:52 you're living it right now. You walked
12:54 into the living room of my apartment
12:56 where I'm going to film. My couch
12:58 cushions are in the in the stairwell.
13:00 Like it's it's pretty like this is
13:03 pretty startup vibe if you ask me. This
13:05 is like no budget hacky. Like me and
13:07 Owen, who's the producer, like carrying
13:09 couches to move them out of the way to
13:11 do this, but I'm also going to get 4
13:13 weeks worth of content out of like the
13:14 grunt work that we put into this today.
13:16 So like, you know, I if I can do this
13:18 for an extended period of time, maybe
13:20 one day someone will believe in what I'm
13:21 doing enough to be able to pay for me to
13:23 go sit in a nice studio that already has
13:25 everything set up so me and Owen don't
13:27 have to sweat for 30 minutes before we
13:28 start. But like I I also know it to be
13:30 true that you need to enjoy these
13:32 moments of the journey cuz like once you
13:34 start to grow up a little bit, you will
13:35 look back and remember like those were
13:37 the days that were actually really cool.
13:38 No, it's it's the best. And I think it's
13:40 also like I've learned that you sort of
13:44 play mind games with yourself to stay
13:46 committed to something to force yourself
13:48 to do something. And one of the the
13:50 interesting things about being even live
13:53 and you you you've made a public
13:56 commitment to your people, to your
13:58 friends, to your family, that you're
14:00 doing this podcast, that you're
14:02 investing time in it, and people should
14:04 also care. And so the minute you stop
14:06 doing that, you sort of break this like
14:08 invisible contract that you have with
14:11 them. And so, you know, I think that
14:13 also is a thing where you're just like,
14:14 okay, I got to keep doing this. I got to
14:15 keep doing this. And I think that's that
14:17 goes for a lot of things. you know, how
14:18 can you set up tricks in your life to
14:21 say, "Okay, I I want to make sure I
14:23 mean, even me quitting my job and not
14:25 having another job is sort of a hack."
14:27 And having a place in New York and
14:28 knowing that that's expensive is sort of
14:30 a hack to be like, "Okay, Max, you got
14:32 to figure this out." Like, you need to
14:34 figure out how to make money. You need
14:35 to stay scrappy. You need to stay
14:37 humble. You need to be out there
14:38 grinding. And and I do feel that. And it
14:41 was like, yeah, I probably spent too
14:42 much on my place and do whatever else,
14:44 but like that forces me to get out of
14:46 bed and work out and stay active and
14:48 meet that person and do some things that
14:50 are easy to say, "Hey, I don't want to
14:52 do this." Yeah. But I think that's a
14:53 fair transition uh into saying that
14:55 you've kind of earned the right to be
14:57 able to like [ __ ] around and find out. I
14:59 mean, you've some of the things you've
15:01 done people will go through an entire
15:02 career having not done for better or for
15:04 worse, but like appreciate it. you we
15:07 can start with the the uh early Uber
15:09 experience because I think you probably
15:11 dealt with some movie like uh moments in
15:14 that journey. Um so you went from early
15:16 employee turned founder turned I guess
15:20 middle to late employee relative to the
15:22 scale of goof. Um so I that's something
15:25 I really want to jump into is like going
15:27 from not being in charge of the whole
15:29 thing to being in charge to not again.
15:31 But let's start back with the journey in
15:33 Uber. So you joined you were what
15:34 employee 25? Yeah, 25. I was 24 years
15:37 old. That's nuts. And there was only
15:39 probably 15 people at the company when I
15:41 started because, you know, they give out
15:42 the employee IDs, but people leave. So,
15:44 I was employee ID number 25. I mean,
15:47 there was Oh, interesting. There was
15:48 probably 15 people, maybe less at the
15:51 company when I started. And we were
15:53 Chicago was the fourth city. So it was
15:56 literally, you know, company launches in
15:58 San Francisco mid 2010, New York was in
16:02 the spring of 2011 and then August was
16:05 Seattle, September was Chicago, and I
16:07 joined in August to to get it going. How
16:09 did you end up at Uber? I hustled. It
16:12 was uh you know I so I was working in
16:14 consulting out of school. I graduated in
16:16 2009 from college and was working at
16:19 Accenture. It was great. Loved it. loved
16:23 the people I was working with, but it
16:24 was tough. I mean, it was corporate as
16:26 corporate gets. You know, I have a joke
16:28 in the podcast when I talk about this of
16:30 like I was wearing these like baggy
16:31 Banana Republic pants and like just
16:35 wasn't vibing. I mean, it was hard. It
16:38 was hard to conform. It was a great
16:40 training ground for me to just know,
16:42 hey, you got to go to this job every day
16:44 and show up and be presentable and not
16:47 act like an idiot. Uh, and then but I I
16:50 knew that was not I needed something
16:51 more entrepreneurial, more scrappy, more
16:53 hustle. I had done a lot of things
16:55 growing up that I didn't even realize
16:57 were entrepreneurial and scrappy. I
16:59 mean, you know, in college, I was
17:01 throwing parties and bar crawls and
17:04 tailgates. I was the Monster Energy
17:06 drink rep. You know, I was buying kegs
17:07 and selling tickets at the door. And
17:09 some of these things that I didn't even
17:10 realize were entrepreneurial and scrappy
17:13 and definitely skills I never thought
17:14 they would translate. They definitely
17:16 did not translate to
17:18 Accenture, but they directly translated
17:21 to Uber
17:24 2011 running around getting people to
17:27 sign up for the app, getting drivers to
17:30 download and and join and on board and
17:33 make money on the platform. And so, you
17:36 know, I whatever I read about Uber, I
17:39 heard about it, and then it was
17:40 basically a multi-month process to
17:42 convince them to hire me. And I got
17:43 turned down, you know, a few times
17:44 during that. Really? So, you got turned
17:47 down multiple times even though there
17:48 were only like give or take 15 to 20
17:51 people at any given moment. Yes. What
17:53 was it? I'm curious. What was the
17:55 strategy that you took that actually
17:56 worked? Like what was the moment in time
17:58 or what was the thing you did or the
17:59 person you talked to where they're
18:00 finally like, "All right, this guy's
18:01 relentless. Like, shut the [ __ ] up.
18:03 Here's your your employee ID. Like, now
18:05 it's time to work." So it was one thing
18:08 was they were asking me for projects
18:09 throughout which I think it's easy for
18:12 people to say, "Oh, I don't want to do
18:14 free work or whatever." But like look,
18:17 if we're being honest, whatever work
18:18 you're doing before you work at a
18:19 company is probably not that great.
18:21 Probably not actually using it for
18:22 anything. They really are trying to test
18:25 hustle, mental ability, u and mental
18:28 ability, I mean more just are you going
18:30 to be able to deal with the fact that
18:31 there's going to be a lot of ups and
18:32 downs. This is going to be hard. you're
18:34 going to be up against challenges that
18:36 you don't know how to solve and you have
18:38 to push through. It's not like there's a
18:39 training for being at a early stage
18:42 startup. I mean, yeah, maybe you've got
18:43 some skills, maybe you've done a few
18:45 things, but really it's a battle of can
18:48 you persevere? Can you keep showing up
18:49 every day? Can you hustle? Can you work
18:51 your ass off? Are you excited? Are you a
18:54 good person people want to be around, be
18:56 in the office with? I mean, that's kind
18:58 of the baseline training for the
19:01 earliest stage of a company. And so
19:03 that's a lot of, you know, what was
19:05 going on when during those months. And
19:06 then what happened was my mom actually
19:08 said, you know, why you you need to turn
19:11 the screws on them. Like you're the one
19:12 who's got a good job at a big
19:15 corporation. Turn the screws. Say you're
19:18 the one taking a risk. You're the one
19:19 taking a shot on them. And I sent a more
19:22 aggressive email than I had sent
19:24 previously. And the the guy who's
19:27 amazing, Ryan Graves, the man, responds
19:29 immediately and says, "I'm on the next
19:30 flight to Chicago. Let's hammer this
19:31 thing out." Um, so it was Mob. It was my
19:34 mom. Wow. Yeah. Well, I'm pumped. She'll
19:37 be my Mother's Day guest on the pod. So,
19:39 if you uh We're going to dive into it
19:40 together. I'm flying her out. We're
19:43 going to the studio. We're going to do a
19:44 Mother's Day podcast together. Wow.
19:46 Interesting. I've never actually thought
19:47 about bringing a family member on my
19:49 podcast. That's an interesting thought.
19:51 So, mom helps you get into Uber. You're
19:53 employee number 25. I mean, can you
19:56 speak a little bit to just like that
19:58 culture because I know a lot of 25
20:02 person companies, right? We're actually
20:03 26 people, so we're like in that that
20:05 range right now. And when you just think
20:08 about what Uber is today, like people
20:11 forget the fact that like most companies
20:13 started from one or two or three people
20:15 depending on how many founders there are
20:16 and you got to build brick by brick. But
20:18 like when you're at 25, I feel like
20:20 oftent times you can sense like this
20:22 one's different and like here's why.
20:24 What would you say looking back on that
20:25 experience like stood out to you is like
20:27 this is this is not your average
20:30 startup? Well, first I mean Travis was
20:33 the best. I mean Travis is the goat.
20:35 Travis Kellen founder and was the CEO of
20:38 Uber. I mean,
20:40 you I'll just I'll never forget watching
20:43 clips of him and and videos of him and,
20:45 you know, before I started, and I didn't
20:47 know who he was before I started the,
20:49 you know, interview process and looking
20:50 at Uber, but you knew he was special
20:53 even in clips. I mean, there's a there's
20:55 a a podcast of him and Jason Calcanis in
20:59 early August 2011, and Travis goes
21:03 through his vision, and it's and that at
21:06 that point, Uber was only black cars.
21:07 So, it's black cars only. It's high-end.
21:09 It's $15 minimum fair. And Travis is
21:12 already talking about a world in which
21:14 everyday drivers could be driving their
21:17 own vehicles in
21:19 Airbnb of transportation. And that was a
21:23 crazy thought in 2011. I mean, ride
21:26 sharing doesn't even come out until
21:27 2013. So, we're still two years before
21:30 this thing's really happening. This is
21:33 before Lyft. This is before Sidecar. and
21:36 Travis was just out there already on
21:38 this. And so I think, you know, for me,
21:40 probably two things. One is you get
21:43 there and you're in the mix with Travis
21:44 and you're immediately just the bar is
21:47 so high. You can, you know, this guy's
21:50 the best and just so smart and such a
21:54 hard worker and you just feed off his
21:56 energy. I mean, you're just so pumped. I
21:57 mean, you're just so pumped to be in the
21:59 room with him and that never waver. Uh
22:02 and then he just had such a clear vision
22:05 and it was
22:06 so simple for people to execute against
22:10 in the beginning which was
22:13 just we have a micro strategy in a city.
22:16 We stand up an operation in a city. It's
22:18 very local in a city. We get
22:21 drivers. We put them on. We pay them a
22:25 base minimum to make sure they're on the
22:27 road. We started with two drivers in
22:29 Chicago. So it's literally start, you
22:31 know, that in in that, you know, 15
22:33 years ago, call drivers in the yellow
22:35 pages, bring them by their professional
22:37 licensed chauffeers. You show them what
22:38 an iPhone is because again, it's 2011.
22:41 You give them that iPhone, which is
22:43 crazy. It's locked down to the Uber
22:44 driver app. They, you know, you convince
22:47 them, hey, press this button, you'll see
22:49 a little man on the screen and go drive
22:51 to that person and pick them up and take
22:52 them wherever they need to go, and we
22:53 promise we'll pay you at the end. And it
22:56 didn't even have, you know, routing in
22:58 the app. So, so what they'd switch to
23:00 like Google your destination? We didn't
23:02 put that even Oh, they what? They would
23:05 they would tell you where that you were
23:06 taking them. You literally just request
23:07 a car. You don't you tell them in person
23:09 where you're going. That was the
23:10 beginning. Was there a parameter? What
23:12 if you got in the car and you're like,
23:13 "Take me from Chicago to Atlanta." We
23:15 had some crazy stuff like that. And we
23:18 would see it because we had And drivers
23:20 would do it. Yeah. I mean, sometimes
23:21 they would call us and like check like,
23:23 "Hey, can I take this person to St.
23:24 Louis or whatever." Um, I mean, some of
23:27 it was fraud and other things, but uh,
23:29 yeah. Oh, yeah. We had we had wild
23:31 things. And almost immediately, you also
23:32 get stories like that. Hey, it's winter.
23:35 I'm at the airport in New York. My
23:38 flight's canceled. I'm trying to get to
23:39 a thing or Christmas or whatever. I need
23:42 to take it across a couple states.
23:44 Driver's down. Game on. Let it go. Um,
23:48 and that and that's like when you know
23:49 to the magic of product market fit and
23:51 this thing's working and you see it out
23:54 there and those types of connections are
23:57 happening. But I mean the first they
23:59 didn't even have an app to start. It was
24:01 just texting. You would just text in and
24:04 the you know you text your address where
24:05 you are and the driver would come to
24:06 you. And that's where I think people
24:08 also don't
24:09 understand how simple the beginning of
24:13 something can be. You know, and even
24:15 something as crazy and massive and
24:17 successful as Uber is, it started as,
24:19 you know, a little SMS,
24:21 Twilio text to get someone to come and
24:24 pick me up. Yeah. Yeah, I think that's
24:25 probably one of the biggest learnings
24:26 I've had on my short founder journey
24:28 thus far is like the misconception
24:30 around how crucial it can be to just
24:33 figure out the cheapest and fastest path
24:35 to like testing a concept that can
24:36 become so much more sophisticated later
24:38 on. But like I think um I think it was
24:41 the Bark Box story. I might have talked
24:43 about this once on the pod a long time
24:44 ago. Do you know how Barkbox started?
24:46 No, I don't. It's like the founders went
24:48 to Washington Square Park and were like
24:50 talking to dog owners and just like,
24:52 "Hey, like would you buy like if I sent
24:55 you a box of toys and treats every
24:58 month, like would you pay for that?"
25:00 Yeah. Like what would you what would you
25:01 want in it to make you pay whatever?
25:03 They just like literally talked to a
25:04 bunch of people like went back to the
25:05 drawing board, did a bunch of research,
25:07 went back to the park with a more
25:09 formulated thought, did the same thing,
25:11 and then were like, "All right, like put
25:12 your money where your mouth is." like
25:13 walked around with like a little stripe
25:14 machine and got like their first
25:16 thousand subscribers like hand tohand
25:18 combat before they ever like sold an
25:21 actual physical box of goods to someone.
25:23 Amazing. Which is like the epitome of
25:25 this. Like I'm I don't know if I got
25:26 that 100% accurate, but it's the message
25:28 the through line of like validating that
25:30 idea um before like raising a bunch of
25:33 money and doing all sorts of crazy [ __ ]
25:35 with it, which I think is another issue
25:36 that we could probably Yeah. talk about
25:39 in building in doing all these things
25:40 that you don't even know if they're
25:42 they're going to work. And I say to
25:43 people all the time, can you do this on
25:44 text? Can you do this on email? Can you
25:45 do this on WhatsApp? Like what what are
25:48 the things ways that you can hack
25:50 something to just see if there's any
25:52 signal before? Why are you building
25:53 something if you don't know if there's
25:54 signal? Yeah, it's uh my my philosophy
25:57 with that is like raise money or put
25:59 resources against something to double
26:00 down on solutions instead of to try to
26:02 solve a problem. If you can solve it at
26:03 a micro level, there's probably
26:05 opportunity to solve it at a much larger
26:06 scale. Absolutely. Um, another thing I
26:09 want to talk about which I was joking
26:10 when I said he's a struggling podcast
26:12 host is just that he's early in his
26:14 journey, but I think you are shedding
26:16 light on a really interesting concept
26:18 with the early podcast which is around
26:20 talking to early employees at companies,
26:22 right? A lot of early employees at
26:23 companies go on oftentimes either become
26:26 founders of their own or like ride that
26:28 journey and become like an integral part
26:29 and make a shitload of money doing it
26:31 like at successful businesses. Um,
26:34 something I'm curious about from your
26:35 perspective, having done what you've
26:37 done in your eyes, like what separates
26:39 good from great in terms of talent
26:41 because like those first couple hires
26:43 that you make are just like so
26:45 important. I think there's an element of
26:47 like the entrepreneur, someone who like
26:48 you think has that gene to be a founder
26:50 one day but maybe isn't there yet. And
26:52 even just like learning about what your
26:54 podcast is about and your journey. I was
26:56 thinking about like who are those people
26:57 to me in my company where I'm kind of
26:59 like holy [ __ ] if they left tomorrow
27:00 like I would be really really upset
27:02 about it because they're absolute a
27:04 players. How are you f how do you think
27:06 about identifying those people? I
27:09 probably obviously there's no perfect
27:11 framework but I probably tend to go
27:14 slightly more junior slightly more
27:18 inexperienced because and ideally have
27:20 some sort of chip on their shoulder. You
27:22 can't necessarily find the chip on the
27:23 shoulder during the interview interview
27:25 process, but that's sort of like a win
27:27 when you do find that person. But I
27:29 think ideally someone who's more
27:33 moldable, more scrappy, more kind of
27:36 game for anything. I mean, you really
27:38 want someone you can throw into the deep
27:39 end and they're down for whatever. And
27:43 you know, I think one of the beauties of
27:44 the early days of Uber was there was a
27:46 lot of people that were down and like
27:49 look, the numbers are going like this.
27:50 So you get the benefit of if you're
27:52 growing and it's exciting and it's fun,
27:56 people are willing to do a lot more
27:58 things than they might be willing to do
27:59 if they thought the company was tanking
28:01 and doing worse and and whatever. So you
28:04 definitely benefit from a company
28:05 succeeding. But I'm looking for people
28:07 that are scrappy but have talent and are
28:10 positive and just going to like kind of
28:12 throw themselves into things and and
28:14 stick through it. And I think not
28:17 always, but sometimes people with more
28:19 education and more credentials and more
28:22 experience tend to be people that maybe
28:25 it's harder for them to deal with the
28:27 chaos of a startup. It's harder for them
28:29 to deal with, wait, I don't have the
28:30 title that I thought I would have at
28:33 this point or my parents promised me I
28:35 would have if I took that class and met
28:37 with that tutor. And so, and like look,
28:39 that's that's me, right? I mean, I'm not
28:41 someone who's overly credentialed or
28:44 overly educated or whatever. And, you
28:46 know, neither of my parents, you know,
28:48 have a college degree. I mean, it's it's
28:50 more um, you know, I think for me, I'm I
28:52 come from a more kind of scrappy
28:55 environment. And so, maybe that's, you
28:56 know, me also kind of seeing myself, I
28:58 think, in in people that I gravitate
28:59 towards. What does that look like on a
29:01 tactical level? Like, are there
29:02 questions you're asking in interviews?
29:04 Are there just like uh qualitative
29:06 activities that you're doing with people
29:07 to just gauge like how they behave? I'm
29:10 curious because I think uh hiring and
29:14 identifying talent is something that's
29:15 so important to me because I've learned
29:17 over the last three years of building my
29:19 company that at the end of the day like
29:22 the thing that a CEO needs to be best at
29:24 is like identifying the right talent or
29:26 knowing who the people are that can help
29:28 you identify the right talent because at
29:30 the end of the day you just need to find
29:32 people who are better than you at
29:33 something because your time becomes
29:35 limited as you're trying to do a lot.
29:37 So, I've been like hyper obsessed with
29:38 just continuing to hone in on like how
29:40 do you sift through noise to like find a
29:43 players?
29:45 It's like almost like controversial at
29:46 this point and I've gotten a few uh
29:48 glass door negative reviews. I love
29:50 this. Hit me and now I'm interested. I
29:53 mean, uh you definitely want to put
29:56 people through the ring a bit. Max is
29:57 like, "Me at 3:00 a.m. We're going for a
29:59 12mi run. I'll see you." I mean, that's
30:01 the thing because I do hear the extreme
30:02 and it's not that. But I want to test
30:06 you a bit if I can within reason. I
30:08 mean, I'm probably going to be Give me
30:10 details. I want like the like the
30:12 interview. I'm probably going to be sort
30:13 of a prick. Like I'm going to be
30:16 dismissive. I'm going to push back. I
30:18 might be a little loud. I might ask you
30:21 some weird questions. Nothing like
30:23 creepy, but like Yeah. I I I first of
30:25 all, I want to know more about your
30:26 background. Like why are why are you
30:28 like how you are? How did you get to
30:31 sitting with me today? Where are you
30:32 from? what you know, again, you're not
30:34 gonna be able to sus all this out in
30:35 interviews, but if you and I were just
30:37 having a drink and I wanted to get to
30:38 know you better, like, I want to know
30:39 where your parents are from. I want to
30:41 know what your parents did. I want to
30:43 know where you went to school. I want to
30:44 know one of the hardest things you had
30:46 to deal with growing up. I want to know
30:48 what your career has been like. What are
30:50 the tough things that you struggled
30:51 with? What are what are the times that
30:53 life didn't meet your expectations? How
30:56 did you react? How do you feel about
30:57 that in retrospect? I mean, I I I don't
30:59 want to know about the good stuff. I
31:01 don't want you to sit down in the
31:02 interview and say, "Let me tell you
31:04 about myself." I say, "I don't No, stop.
31:06 Stop. Don't I don't want to know your
31:09 script. I'm going to ask you some
31:11 questions." Like, I don't want to know
31:12 what your version of the events are.
31:14 We'll get to that, but I want to sus
31:16 that out and I want you to do something
31:17 ideally. I want you to put together a
31:19 project or go bring me a lead or go
31:23 identify who you would target or come
31:25 work with me for a couple months or a
31:27 couple weeks. Come be an intern. I mean,
31:29 I at GoPuff, I had like four or five
31:32 adult interns, and I feel bad calling
31:34 them interns because they were like in
31:36 their late 20s or early 30s, but we did
31:40 it in a more trial way. And they were
31:41 all rock stars. They were like, "Screw
31:43 it. I do want this job. I do want to
31:46 work here. I do believe in the
31:47 opportunity." And like, look, I'm not
31:49 saying it in a demeaning way. I'm
31:50 saying, "Look, I believe in you. I just
31:52 don't necessarily have a spot. or look,
31:55 for these reasons, I just can't bring
31:56 you on full-time or I need you to kind
31:59 of prove yourself a bit. I'm not going
32:00 to treat you bad. I'm not going to
32:02 anything else. I'm actually I want you
32:04 to succeed, but I need to see it. And a
32:07 lot of times those people just rip
32:09 because then they have a chip on their
32:10 shoulder. You see the chip and they
32:12 don't want the title intern and they do
32:14 feel like they've done something in
32:15 their past and they do feel like there's
32:16 something to step up towards. And so,
32:18 you know, again, it doesn't always work
32:19 like that. You can still piss some
32:22 people off. you can accidentally be
32:24 meaner to someone that you mean or
32:26 whatever else. But when that sweet spot
32:29 and that's kind of what they did at Uber
32:31 to me and a lot of people, not
32:33 necessarily purposefully, but like they
32:35 sort of tried to see, are you a culture
32:37 fit? You know what your culture is? You
32:39 have to figure out how do I then put
32:42 someone through whatever puzzle to see
32:44 if they're going to fit this culture
32:45 because if someone's not a culture fit,
32:47 it is never going to work out. Yeah. And
32:51 I've I've learned that the hard way with
32:53 a handful of people. It's like you can
32:54 have all the credentials, but like
32:56 certain businesses are built certain
32:57 ways and you need to be able to like fit
32:59 in or not. The the Go Puff guys, there's
33:02 a a ton that I just, you know, love and
33:05 respect about Rafnik here. I think one
33:08 of the things I really learned from them
33:10 was the culture piece of just look,
33:14 they're big family guys. They're very
33:16 supportive. they're going to um you know
33:19 ingratiate you and you know be kind and
33:21 and whatever else, but ultimately it's
33:24 their company. It's their culture
33:26 they're trying to build. Again, they're
33:27 collaborative. They're great. I was in
33:29 those meetings with them. We were trying
33:30 to figure out a bunch of things, but at
33:32 the end of the day, it's their culture
33:33 and it is their company and it is their
33:35 vision and it should be. And they of
33:39 course they they shapeshifted and and
33:41 and evolved and whatever else, but you
33:43 know they also tried to be clear about
33:45 what their principles were and make sure
33:47 that people fit into their puzzle and
33:49 and it again there's there's back and
33:51 forth on that and it has to work right
33:53 but like that's right. And when I talk
33:56 to entrepreneurs now it's like well
33:57 you're trying to be open for everybody
33:59 and this and that. It's like that's too
34:01 much. Like what is the thing you're
34:02 trying to build? What is your vision? be
34:05 clear on it and find people that fit
34:07 into that. Again, it's going to evolve.
34:08 It's not that it's it's totally black
34:10 and white, but it needs to still be your
34:13 thing. And if people aren't going to fit
34:14 into that, they're going to likely not
34:16 work out. Yeah, you actually So, you
34:18 bring up something interesting I want to
34:20 talk about for people who are listening
34:21 and don't know this. I was at the bottom
34:24 of that totem pole at Go Puff. at the
34:27 bottom. Not at the bottom, but pretty
34:28 low to the bottom on the on like within
34:30 one team at the I think I was like the
34:32 first BD associate or whatever the
34:34 madeup title was at the time. Um, and
34:37 got to like see firsthand. That was like
34:39 my first exposure at a company that was,
34:41 you know, moving at that pace, had
34:43 raised that amount of money, had that
34:44 many like heavy hitters around the
34:46 around the table. And I think, look, I I
34:49 definitely felt like I brought a couple
34:51 unique ideas to the table, but at the
34:52 end of the day, like it's really you got
34:54 to like know your role. Uh, and yeah,
34:57 it's important like don't take no for an
34:58 answer and recognize that like you can
35:00 create you you create your own luck by
35:02 like doing things adding value, whatever
35:03 it might be. Um, but it was a lot of
35:06 like sitting around and seeing what
35:08 others are doing to like understand what
35:10 it takes like operate at the next level.
35:12 Cuz if there's one thing I've learned
35:14 from starting my own company, there are
35:15 levels to this game where like you think
35:17 you're doing something cool and then you
35:18 see how other companies are operating
35:19 and you're like, "Holy [ __ ] like
35:20 they're just thinking about problems in
35:22 a way that I just didn't even know
35:23 existed." Uh, which brings me to my next
35:26 question. You have like sat at the table
35:30 in some of the like most highstakes
35:32 conversations. I mean, you were the
35:33 chief of staff to founders of a company
35:35 that have raised what $4 billion, right?
35:38 Like it's like hard to fathom the amount
35:40 of zeros at the end of like these
35:42 numbers that you're looking at on like a
35:43 P&L. What is it like having those
35:46 conversations when the stakes are that
35:48 much higher compared to maybe like other
35:50 situations you've been in? Because
35:52 honestly, you're shedding a light and
35:54 giving a lens to the people listening to
35:55 this that I don't think we've had before
35:57 of like you're sitting in a room with
35:59 the founders of a company worth billions
36:00 of dollars with investors who've
36:02 deployed nine figures into this company
36:04 having to like make decisions and have
36:06 hard conversations. Like walk through
36:08 the framework around that a little bit
36:09 because I just think that's experience
36:11 that you can't you can't really like
36:13 read
36:14 about, you know. I think well one thing
36:18 is imposttor syndrome or whatever you
36:21 want to say you know there's like if
36:23 you're like what's something you would
36:24 tell your younger self it's like you
36:26 always think you don't know what you're
36:28 doing like you're always you're and you
36:31 should be putting yourself in situations
36:33 where you are beyond what where you
36:36 think your skis are right where you
36:38 think oh man I've pushed myself again I
36:41 can't believe I'm in this room I can't
36:43 believe I'm in this situation I don't
36:45 have the experience experience for this,
36:46 you know. So, I think it's a bit of you
36:48 should be pushing yourself to be in
36:49 those environments. And that's a good
36:51 thing. It's good to still feel the I
36:54 don't know if I know how to help in this
36:56 situation, but so I think some of it's
36:58 balancing the humility, knowing your
37:00 place a bit, which is I'm here to help
37:03 facilitate this conversation. I'm not
37:05 the main person, but that's okay. I can
37:07 still make a big impact. And honestly, a
37:09 lot of times it's better to be a
37:11 secondary player and still make an
37:14 impact and be in the mix and stay in the
37:16 room. Um, and then I think it's, yeah,
37:18 how do you just lean on your experience
37:20 enough to know, okay, you know, I might
37:24 not know this thing we're discussing
37:26 exactly, so maybe I sit back on it, but
37:28 like this thing, I do have something
37:30 that I saw before that mirrors this. And
37:33 maybe it's not even advice as much as
37:35 it's, hey, look, this thing we're
37:38 discussing, I saw this before at Uber. I
37:42 saw this before when I had my own
37:44 company. This is how it played out for
37:46 us. I'm not saying it's an equivalent
37:48 situation, but it's damn near close. And
37:53 this is how this played out. So, can we
37:55 all just agree maybe we should think
37:58 about this a bit differently if we think
38:00 that this piece is true? And so it's
38:03 it's like how do you influence more than
38:05 you say, more than you tell? And how do
38:08 you influence on the right things?
38:10 Because when you're lucky enough to find
38:12 yourself in these rooms or these
38:13 situations, you want to stay in the
38:15 room. And you only have so many bullets
38:18 or whatever to be able to deploy to say,
38:21 "Hey, I think I might be kind of right
38:23 or I have an example on this thing." So,
38:25 look, it's it's it's a balance um in
38:28 something that, you know, I mean, I
38:30 worked for Emil Michael, who's
38:32 unbelievable, and you know, was was
38:34 number two to Travis at Uber, and I saw
38:36 him play, you know, one of the best
38:38 number two jobs ever. And and it it
38:41 inspired me in a lot of ways of, okay,
38:44 you don't need to be the number one
38:45 person. You don't need to be the
38:46 founder. And that's kind of what the
38:47 podcast is about, too. It's just like
38:49 being an employee is awesome, too. you
38:50 could still rise the ranks and be in
38:52 these interesting meetings and be in
38:54 these rooms and make a big influence and
38:56 not be the founder. And I think it's
38:58 just it's so it's like a misnomer at
39:00 this point that you have to start
39:01 things. There are so many early
39:03 employees that make handover fist more
39:05 money and accumulate more accolades than
39:07 like majority of founders. Yes. Right.
39:10 Like and that's actually really
39:11 underestimated. I think there's a piece
39:13 of ego involved in that as to like why
39:14 there's probably people starting things
39:16 that maybe shouldn't be. Um there's a
39:18 piece of it where you're starting
39:20 something that doesn't actually have
39:21 legs, but you don't want to give it up,
39:22 so you end up doing it versus some
39:24 people who find themselves in a
39:26 situation of being an early employee at
39:28 some companies that go on. I mean the
39:29 look at what just happened with Nvidia.
39:31 I think wasn't it like a thousand
39:33 employee? I don't know the number. I
39:34 think it was something like a thousand
39:36 employees made like over half a million
39:38 dollars. So something like hard to even
39:41 like comprehend. Yeah. And even if it's
39:43 not financial, I mean, just some of my
39:45 best friends in the world are people
39:46 that I've worked with. And so, you know,
39:50 just from an experience standpoint, even
39:51 if the monetary
39:53 rewards aren't
39:55 outsized, the personal rewards certainly
39:57 are, right? I mean, you know, you're in
39:59 the trenches with people. You're in day
40:00 in day out. I mean, I love everyone I've
40:04 worked with. Even if they're people that
40:06 were dicks to me or whatever or would
40:09 like you still have these these bonds,
40:11 right? I mean, you know, I'm, you know,
40:12 so I think it's that's something where
40:15 it's I don't I don't I don't sort of get
40:19 the culture of everybody's got to start
40:21 things and do this and solo entrepreneur
40:24 and blah like all this entrepreneurial
40:26 stuff and like look, I still respect it.
40:27 I did start something. We did have a
40:29 successful exit. So, I get it, but man,
40:31 working in a company has been awesome,
40:33 too. And and unbelievable experience
40:36 that I wouldn't give up for anything. I
40:38 want to talk about that, though. You
40:39 You're so humble about it. you left Uber
40:43 start maybe had some stops along the way
40:45 and started started Bandit. Uh I want to
40:48 understand two things. The first one is
40:50 like what was the moment in time at Uber
40:51 where you were like all right like I'm
40:52 ready to go off and do my own thing and
40:54 then the second one was how did you land
40:57 on Bandit?
40:59 You know I think so Travis left and
41:01 whatever in mid 2017. So that was that
41:03 was a in a left and that was tough. I
41:06 mean, I was definitely tied to those
41:07 guys in a lot of ways and and it was
41:09 tough when they when they left the
41:11 company. So, I ended up sticking around
41:12 like another 12 months after they
41:14 departed, but it was a different
41:15 company. It was it was clearly Uber the
41:18 corporation now, not Uber the startup.
41:20 And that's great. I mean, DAR is the
41:22 man. I know some of the leadership team
41:23 over there. They're awesome. Like, more
41:25 power to them. I think though I was
41:27 like, eh, this probably is not no longer
41:29 my thing. thing and like look I like
41:30 earlier more you know I think I thought
41:33 that at the time and I and I still
41:35 believe that that's correct. Um and then
41:37 I think you know I left with a little
41:38 bit of a chip on my shoulder like I you
41:40 know I left with
41:42 okay I was really lucky to get this job
41:45 at Uber again. I worked my ass off to
41:47 get it. I was really lucky though to be
41:49 here make the money I did you know the
41:51 success that that we all had and but I
41:55 wanted to kind of prove it again. Uh,
41:57 and so I I thought about doing, you
42:01 know, working somewhere else, but then
42:02 it was also so hard to recreate that
42:04 magic. And that's, you know, I find that
42:06 in a lot of people that have been on a
42:07 rocket ship like Uber and left. It's
42:09 hard to catch the high again. It's hard
42:12 when you kind of are, you know, in some
42:14 ways on a peak and you're trying to find
42:16 it again. It's tough. There's not a lot
42:18 of Ubers. There's not a lot of those
42:20 experiences. And so that was also where
42:21 I was like, all right, I'm not going to
42:22 recreate this by working another company
42:24 right now. um maybe starting something
42:27 is the move. And then with Bandit, it
42:30 was uh you know, we saw what was
42:32 happening in China with Luck and Coffee.
42:35 They're basically I just give a quick
42:36 two seconds on what Bandit was. Yeah. So
42:38 Bandit was a uh sort of digitally
42:42 native, you would say, uh coffee shop.
42:44 So we were app only before anyone was
42:48 appeas 2019. So app only coffee shop.
42:51 You walk in, it's still a normal coffee
42:53 shop, but you have to use our app to to
42:56 order and purchase, which again was a
42:58 big deal in 2018, 2019. And then the
43:01 infrastructure was modular and more
43:03 mobile, so we could move it around. So
43:05 we were doing revenue share deals with
43:07 landlords where we could just drop the
43:09 coffee shop into place and only took us
43:11 a few hours to set it up. And then we
43:13 would do a revenue share deal. And so we
43:15 were doing these in like office building
43:16 lobbies and white box, you know, retail
43:20 real estate in a way of doing this in a
43:22 way that um was scrappier and we could
43:24 move it around and, you know, didn't
43:26 require all of the uh upfront costs that
43:29 a normal kind of brickandmortar
43:31 restaurant would cost. So that was that
43:33 was banned. We ended up having four or
43:35 five locations in the New York area and
43:37 then three locations down in Austin
43:39 before we got acquired. Can you walk
43:41 through that journey of getting
43:42 acquired? I think um you know we've had
43:45 a couple founders on here who've sold
43:47 businesses but I've never actually gone
43:48 deep on like the moment in time where
43:50 you're like wait I think I'm going to
43:52 sell this company to like who are the
43:54 potential buyers to wait they actually
43:56 just told me they're going to do it. Oh
43:58 man it was crazy.
44:00 I So I mean if you think about it was a
44:03 very condensed timeline for us overall
44:05 from start to finish. Uh, you know, we
44:09 March 2020, we've got three locations in
44:14 New York. They're humming. The newest
44:16 location we just opened like a month
44:18 prior and it was doing like three, four
44:20 grand a day in sales, which is pretty
44:22 good for the one in New York. Yeah. The
44:24 second one because we had closed ones.
44:26 It was basically our our next location.
44:28 So, we had two active at that time. We
44:29 had opened three and the third one was
44:32 Hum. We launched food. It was in a good
44:35 building. People were in the office
44:37 every day. It was humming. And you know,
44:40 we're honestly we had raised, you know,
44:42 almost four million bucks from investors
44:43 like, "All right, we didn't know what we
44:46 were doing and a million mistakes and
44:47 James, my co-founder, is the best." And,
44:49 you know, we were having fun, but it was
44:51 crazy. We're trying to figure it out.
44:53 And then CO hits and then New York shuts
44:55 down. You know, we were literally
44:56 meeting with investors Wednesday night.
44:59 Do we do another raise? How do we launch
45:01 more of these? is how do we sort of
45:02 playbook this to you know because the
45:04 idea was we want to launch a bunch of
45:05 coffee shops and then COVID hits the
45:08 city shuts
45:10 down no one's going back into an office
45:12 we know now for years and so we just
45:16 shut the business down and then within a
45:19 few weeks we were like all right we can
45:22 either give whatever money we have back
45:24 to investors or we can relocate relocate
45:27 the business to somewhere else that's
45:28 warm in like a Republican city so maybe
45:31 there's less
45:32 restrictions going to Texas. Yeah. So,
45:35 it was like screw it, we're going to
45:36 Austin. And uh we reopened in July in
45:40 Austin. It was awesome. I mean, Sam
45:42 Doyle, the man, Ron, like these guys,
45:44 you know, flew down with us. We flew
45:46 down to Austin.
45:48 We found real estate. Wait, I actually
45:50 didn't know that's what happened. I That
45:52 was a complete joke when I said we're
45:53 going to Texas. Oh, no. No. We're going
45:54 It was literally like cuz you said warm
45:56 weather Republican. I'm like, well,
45:58 that's kind of like option number one.
45:59 Yeah. And again, it was like kind of pre
46:02 even knowing what was going on with the
46:03 world at that time. Yeah. Yeah. It was
46:05 like Nashville,
46:07 Phoenix, Dallas, Houston, Austin, Miami.
46:11 You know, Miami is weird because like
46:12 culturally we were like, I don't know if
46:13 we can figure it out there. Austin's
46:16 cool, but still Texas. Um, so yeah, we
46:19 went to Austin, flew a couple guys down.
46:22 They were kind of our launchers to
46:23 figure it out. And then by July 1st, we
46:25 were all there. And uh, we launched the
46:28 food trucks. you could request our food
46:29 truck to come to your neighborhood and
46:31 we would give, you know, sell coffee off
46:33 of it. And we launched an actual retail
46:35 location pretty quickly. And we just
46:37 moved that infrastructure. So we moved
46:38 it from New York down to Austin. Again,
46:40 white box the real estate, drop it in,
46:42 and you got a coffee shop. We built an
46:44 Airstream trailer. I mean, all in a
46:46 pretty quick timeline. What happened was
46:48 I knew some people that had joined
46:50 Gouff. We were in desperate mode. I was
46:53 just like, I'll do anything with anybody
46:55 right now. like, "Hey, go puff. Do you
46:57 want to sell coffee beans that we could
46:58 brand as Bandit? Do you want?" And then
47:01 it was like, "We don't want to do that,
47:02 but maybe we would do you could put your
47:04 truck in our parking lot and sell items
47:07 on our menu." Like, all right. And then
47:10 it kind of escalated from there where
47:11 they're like, you know, screw it. What
47:12 if we just bought you guys and you ran
47:14 that whole operation for us? We want to
47:17 get into food. We want to get into
47:19 coffee. And for us at that point, you
47:21 know, it was tough to see a path
47:22 forward. I mean, I still believe that we
47:24 could have figured it out. Still
47:25 trusted, you know, what we were doing.
47:27 We still had money in the bank. But it's
47:29 tough. You go from riding high in New
47:32 York shutting down, reopening, you know,
47:35 all the issues of changing cities and
47:36 whatever else. I mean, to to find maybe
47:39 a successful off-ramp was like,
47:42 hallelujah. Oh my god. Please, please,
47:45 please, let's make this happen and make
47:47 our investors whole. I mean, just the
47:49 whole thing. It was it was unbelievable.
47:51 And so when it was done and like it was
47:53 tough. I mean there was a time where we
47:54 thought the deal was dead. Um you know
47:58 but when can you can you walk through
47:59 that? I mean you obviously have to go
48:00 into extreme detail to the point where
48:03 like I probably shouldn't be sharing
48:04 this but I I want to get as close to
48:06 like the reality of that as possible
48:08 because I feel like that's the that's
48:09 the thing I'm curious about. So we the
48:11 first thing we were going to do is this
48:12 trial with them. we were going to put
48:13 the truck in the parking lot and sell
48:16 the coffee on their app. And then, you
48:18 know, we were apprehensive to do that
48:21 because we didn't know if it was going
48:23 to succeed. And I think at that point,
48:24 you you hit a point where you're like,
48:26 all right, this is a sick partnership
48:28 opportunity. Then you hit a point where
48:30 you're like, [ __ ] they could buy us.
48:33 And then you're like, that's crazy. Then
48:36 you're like, wait, no, they actually
48:38 might buy us. So then you have to have a
48:40 conversation of well do we even do this
48:42 trial because if we do the trial and it
48:45 doesn't go well it may be way less
48:47 likely that they buy us like it might be
48:48 a zero and I think it will go well but
48:52 you know you start to look at data you
48:53 start to project some things out you're
48:54 like [ __ ] like maybe we lean harder what
48:57 what are you trying to optimize for you
48:59 gota stop and ask yourself that a lot of
49:01 times right wait hold on a second we're
49:02 jumbled up we've been working on this
49:04 thing for a bit what are we trying to
49:05 optimize for and then you're like I
49:07 think we're actually optimizing for
49:09 getting acquired. I think that's a
49:10 better outcome and I think a better
49:11 outcome for them too. um because they
49:13 had a team working on it and it wasn't
49:15 getting off the ground and we started
49:16 working with that team and I remember
49:18 calling Dan Folkman the man who was
49:21 running the deal on the other side and
49:22 being like hey I don't know I think
49:25 we're going to hold our end of the
49:26 bargain or the partnership but I don't
49:27 know if they're going to you know these
49:29 guys that you've got there and that and
49:32 again it was that was real and you know
49:33 I think look I mean people know me I
49:34 mean I wasn't you know none of it was
49:36 was BSSE right we and we had similar
49:38 investors and stuff so it was all you
49:41 know everybody was trying to do the
49:42 right thing by each other and then they
49:44 sort of look into it and they're like,
49:45 "Yeah, you're right." Like, we don't
49:46 know if these are the guys to execute.
49:49 Um, and then, you know, so you start to
49:51 try and position, okay, let's actually
49:53 try and position this thing for an
49:55 acquisition path versus a partnership
49:57 path. And then from there, you know, was
49:59 there a moment in time where you
50:01 actually were the one that initiated
50:02 like that literal conversation to
50:04 someone at Gooff where you're like,
50:06 "Look, I know we're doing this
50:07 partnership, but like do you guys have
50:08 interest in buying us?" Is that like
50:09 actually the conversation? starts to
50:11 come at least I think this is probably
50:12 how it goes some it almost starts to
50:14 come up as a joke or like offh hand
50:16 right like you know maybe we just buy
50:18 you guys you're like yeah yeah maybe and
50:21 you're like okay but really you know
50:24 it's almost like dating or something too
50:26 where you're like okay well now how do I
50:27 not act desperate you know getting on my
50:29 knees and begging you right now probably
50:31 is not right the reaction but okay and
50:34 you're like I guess I got to like play
50:35 it cool like yeah I don't know maybe
50:38 maybe we'd be down you And so like it
50:41 kind of starts more casual like that and
50:43 then it's like all of a sudden we're
50:45 doing diligence and talking to lawyers
50:47 and um you know I talked to my lead
50:50 advisor investor uh and you know he was
50:53 like this seems like a no-brainer if we
50:56 can figure it out. Um and then you know
50:58 I think we had the you know we were like
50:59 do we do we go try and get a competitive
51:02 offer? But then we made the decision
51:04 like not to mess around like we knew
51:05 these guys we trusted them. I think they
51:08 trusted us. We had really good
51:09 interactions with the founders. It was
51:11 like, let's not let's not mess around
51:13 here. Let's not play play any games.
51:16 Let's try and figure out. So, we had a
51:17 deal in place kind of. It kind of fell
51:21 through. So, we thought the deal was
51:23 dead and then we had to, you know,
51:25 revive it, change a couple things, and
51:28 then, you know, we felt good about it,
51:29 and then it was, you know, came
51:31 together.
51:32 What was that that uh journey like for
51:34 you going from early employee to the man
51:37 in charge back to employee? Like was
51:40 there was there a moment where like the
51:42 you had to like reframe your approach to
51:44 like every day because now you're like
51:46 reporting to someone. I mean dude I was
51:48 so thankful to start that it was just
51:51 like this is salvation. Like you know
51:54 you just go from
51:56 Friday at 3:00 and you're like you know
52:00 can we pay for this thing? Can we not
52:01 pay for this thing? I'm not paying
52:03 myself. You
52:05 know, this is hard. How are we going to
52:08 do this? We're having an issue. Someone
52:10 just quit. We have to fire this person.
52:13 You know, sales were down yesterday
52:16 to, oh my god, we're like safe. This
52:21 part of the journey is over. I mean, it
52:23 didn't feel job mission accomplished,
52:24 but it just felt like, wow, a bunch of
52:27 the things that were stressors yesterday
52:29 are not stressors today. And that was
52:31 just a feeling I'll never forget. And so
52:35 I think from that standpoint, I was so
52:37 thankful to just be there. And then it
52:39 was cool
52:40 because we had resources. They wanted me
52:43 to build. They wanted to to fund that.
52:46 They wanted us to grow. And I was kind
52:48 of back in my Uber seat a bit except a
52:52 couple years older, hopefully a couple
52:54 years more mature, hopefully a little
52:56 bit more humble and whatever else. and a
52:59 fresh start to be like, "Okay, how do I
53:00 want to do this the second time around?"
53:02 Doesn't mean you still make a million
53:03 mistakes and whatever else, but it was
53:05 like, "This is cool. I actually I'm good
53:07 as an as an employee. I think I am. And
53:10 I'm good at like figuring out how to
53:11 shape shift a bit and like running my
53:13 mouth to a point and finding the line,
53:16 maybe stepping over it a bit, but like
53:17 staying behind it and trying to add
53:19 value, whatever else." And so, I think
53:21 that's part of also why when the podcast
53:23 came together, it was like I think being
53:25 an employee is awesome. And I think
53:27 people aren't out there talking about
53:29 how great it was. And I had the
53:31 experience
53:31 of we start something and it was great.
53:34 I loved having Bandit. I loved being
53:36 with my co-founder, but also getting
53:38 back to Gopuff with those guys and a
53:40 little bit less stress on that level, a
53:41 little existential stress. And being
53:44 back in the driver seat of growing and
53:46 building again was like this is great.
53:48 And you were that like you made this
53:50 comment earlier like when I left Uber, I
53:52 didn't know if I'd ever get a chance to
53:53 like be on this rocket ship again. And
53:55 it's like you kind of found yourself
53:57 back in the same seat, ironically
53:59 enough, with a lot of the same people.
54:01 Ironically enough, with a bunch of the
54:02 same people, which again shows you how
54:04 your network is everything and how the
54:07 people that you meet throughout your
54:08 career, you end up sitting with them
54:11 recording a podcast years later, right?
54:13 You don't know where any of these things
54:15 are going to go. So, it's just like
54:16 curate your friendships, curate these
54:18 relationships, keep growing, keep
54:20 building, try and stay humble, keep
54:22 doing stuff. And yeah, then all of a
54:24 sudden you're back. I'm back in the seat
54:26 again. You're like, "God, I can't
54:27 believe how all this comes around. I
54:29 can't believe how all this works. This
54:30 is awesome." And it was just a lot of
54:33 positive and then you just rip it and
54:35 you just see what see what happens. One
54:37 other thing I wanted to talk about with
54:39 you because you've been like front row
54:41 seat for this is just the concept of
54:43 fundraising. I mean, you've arguably
54:45 been exposed to some of the best
54:46 fundraisers in the world of startups as
54:49 we know it today. I mean, between Uber
54:51 and Gouff, I don't even know how many
54:52 zeros are are included in the amount of
54:55 dollars raised. And not to say that I
54:57 mean, we know for sure not every
54:58 business needs to do that, but for those
55:00 who do, like they could probably learn a
55:02 thing or two from what you've seen on
55:03 like what a good fundraiser does versus
55:05 a bad. Having had a front row seat to
55:07 people who've raised like hundreds of
55:09 millions and billions of dollars, like
55:11 what are your biggest takeaways or
55:12 learnings? I mean, momentum is
55:15 everything. You got to ride the wave.
55:18 you know, you you think you've got the
55:20 magic and the magic goes away. So,
55:22 you've got to take a take advantage of
55:24 every opportunity. I mean, look, you
55:27 want to be obviously there's some
55:28 balance there. You want you don't want
55:29 to over raise. You don't want to, you
55:30 know, raise incorrectly and whatever
55:32 else, but like if you feel like you've
55:34 got some momentum and people are
55:36 interested, you should take advantage of
55:37 those moments because I've seen the ups
55:38 and downs. I've seen you're on the come
55:41 up, people are pumped. I mean, even on
55:43 the bandit at the small scale that we
55:45 were at, when we had momentum and there
55:47 was some FOMO and whatever else, you can
55:50 raise and you can you can create FOMO
55:51 and you can get people excited, you can
55:53 take advantage of it, but the minute
55:54 it's gone, it's very hard to recapture.
55:56 So, you got to seize the opportunity
55:59 when you have it. And then I think it's
56:01 like, you know, some of the process
56:03 stuff of actually running a real
56:06 fundraising process, actually having
56:08 data rooms and decks and things and
56:11 teasers and whatever else and curating
56:12 your list of people and and saying we're
56:15 going to do this over a multi-week
56:17 process and we're going to do upfront
56:19 meetings and then elevate to the next
56:22 thing and then elevate to the last round
56:23 and we're going to make a decision by
56:24 this last date. Again, some of these are
56:27 champagne problems. Some of these are
56:28 harder to do in in in tougher
56:30 environments or whatever else, but you
56:33 that allows you to create some FOMO,
56:35 create some intrigue. These investors
56:37 talk, they know what each other are
56:39 doing. You have one person pass, someone
56:42 else is going to know they passed. That
56:44 might lose a second person. So, you just
56:46 you want to have some structure to these
56:49 things. And you don't necessarily want
56:50 to dabble in it when you're not
56:52 fundraising. Like, you're either
56:54 fundraising or you're not fundraising.
56:55 And you can really screw yourself if you
56:57 start to dabble in some of these
56:58 conversations before you're ready for
57:00 it. Especially at the institutional
57:03 level. I think like with earlier stage
57:05 companies, you know, with us, for
57:07 example, like we raise on a safe, it's
57:08 like if you come across an interesting
57:10 angel investor who like can bring a
57:11 unique lens to it. It's like we're not
57:13 fundraising, but will I make room for
57:14 you? Like yeah, probably. It probably
57:16 makes sense for my business. Um, but
57:18 yeah, I've always just wondered like how
57:20 the calculus changes in these in the
57:23 optics of these conversations when
57:24 you're raising like a million versus 5
57:26 million versus 500 million. Um, because
57:29 I do think the the the narrative is
57:32 definitely different and like the antics
57:34 you have to use for better worse cannot
57:36 be the same for someone trying to get a
57:38 million dollars versus $500 million.
57:40 Well, but that also just comes back to
57:41 the relationship piece is so important.
57:43 I mean, I saw that with Emil at Uber and
57:46 with um you know, Cameron who ran
57:49 Corpdev at Uber and uh the Rafikir at at
57:53 Go Puff, Dan at Gou. I mean, these guys
57:57 are actively having conversations with
57:59 investors, you know, again, the the
58:01 appropriate ones, not necessarily, hey,
58:03 outright we're raising right now or like
58:05 but curating these relationships,
58:08 teasing out enough info. It's much more
58:10 of a personal relationship at that point
58:13 when you're raising those those massive
58:15 dollars. And all those guys who are who
58:16 are some of the best fundraisers in the
58:18 world are are great and they're real and
58:21 those are real relationships. I mean,
58:22 it's not like they're playing a game. I
58:23 mean, those people care about people and
58:25 and are best in the world at it. What
58:28 advice would you give to someone who
58:30 maybe doesn't feel like a founder, but
58:31 wants to like start something great? Oh,
58:33 man. Well, I'd go work somewhere. I'd go
58:35 be an employee somewhere. I go work in
58:38 the early stage. I think that I mean
58:41 that's what I'm trying to do with the
58:42 pot is like bring back make startups
58:44 great again. Like make make working
58:46 early stage great again. I would my
58:49 advice would be find a list of five 10
58:53 companies that you think are just cool.
58:55 Like I just thought Uber was
58:57 cool. You like did you know anything? I
59:00 was 24 and I'm like from Chicago. Like I
59:03 you're lucky that I was able to tie my
59:04 shoes. Like I just thought it was cool,
59:06 right? I just wanted to run around
59:08 Chicago and tell everyone to use a black
59:11 car service that they could request
59:12 through their phone. I was just pumped
59:14 about that. I'm a promoter and I think
59:17 so you make a list of 10 companies that
59:19 you're pumped about and figure out how
59:21 you can add value and try and get a hold
59:23 of a founder or an employee or anybody
59:26 there and try and get in the mix. And
59:28 even if it's like you're working a sales
59:29 job, you feel like you don't have a lot
59:31 of time like I don't know, can you give
59:33 somebody five 10 hours a week? Can you
59:34 bring so many leads? Can you do some
59:36 thing? I just think if you want to do
59:39 something entrepreneurial and early
59:41 stage, the best way to get in the mix on
59:43 it is join something early, join
59:46 something cool, build your network, meet
59:49 interesting people, and and your world's
59:51 going to explode in a good way. Looking
59:54 back on your journey, what would you say
59:56 is the biggest Turning Pro moment that
59:57 you've had along the way? That moment
59:59 where you feel like everything just
60:01 changed and you were playing a different
60:02 game.
60:05 I mean, I
60:07 think I mean, joining Uber was insane.
60:10 Joining Uber was insane. It definitely
60:13 felt I couldn't believe, you know, as
60:16 you ask what's my advice for someone
60:18 trying to figure it
60:20 out. I just you start probably thinking
60:25 about your future when you're 16, 17,
60:27 but so much is kind of decided for you,
60:29 right? Like your where you are at that
60:31 point is decided for you. where you're
60:32 going to go to college and some of those
60:34 things. Yeah, you've got some of but you
60:35 have barely any you don't even know what
60:37 you want to do at that point. You don't
60:39 know where you want to be. You don't
60:40 really know who you are. And then all of
60:42 a sudden, you're like 22 and you emerge
60:44 from college, this construct that we've
60:47 developed. And now you like still don't
60:49 know where you want to do or what you
60:50 want to be. You're just probably in debt
60:51 and like whatever else. And I think for
60:54 me, the fact that a couple years out of
60:57 school where I still didn't know who I
60:59 was or what I wanted to do, I was able
61:01 to find myself in a situation where I
61:04 was just so pumped. And it was like,
61:06 wait, these people are more like me than
61:09 other people I've met, and their values
61:11 are more like mine that I didn't even
61:13 know I had these values. But like, you
61:15 start to piece together and you're like,
61:16 wait, this I know this. I don't know it,
61:18 but I kind of know this game a bit. And
61:21 I feel like I can learn this game. And
61:25 that's why I just push on people that
61:27 are trying to figure things out or
61:29 earlier in their career or whatever else
61:30 to just like just get in the mix,
61:32 experience new things, try new things
61:34 because you just don't know which part's
61:37 going to sort of pull you in. And if you
61:40 are lucky enough to find that, then you
61:42 just keep going down that rabbit hole.
61:44 And so I think for me, probably joining
61:46 Uber was a huge moment, huge turning pro
61:49 moment. And then probably the the bandit
61:51 to go puff where you were like, "Holy
61:53 [ __ ] like I can't believe I have the
61:55 privilege to be able to do this again
61:57 and like let's make the most of this
61:59 experience and I'll do it until it's no
62:02 longer a thing." And then when it's not,
62:04 I'll be sitting here with you and like
62:05 all right, how do we figure out what the
62:06 next thing is? Max, this has been
62:08 awesome. I appreciate you coming on
62:10 today, dude. Thanks for having me. You
62:11 want to look at that camera and let
62:13 everyone know where they can find the
62:14 early pod?
62:15 Earlypod.com on Instagram. Early Pod on
62:19 Tik Tok. Early Pod and we are on
62:22 Spotify, Apple, YouTube. Early podcast.
62:25 Subscribe, please. Hell yeah, dude.
62:27 You're the man. Thank you so much.
62:28 Appreciate it.
62:32 [Music]
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