Master The 4-Day Workweek with Natalie @ WildBit.com - Escape Velocity Show #26
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Summary
In this episode, I chat with the founders of Beanstalk and Postmark about how they built one of the most successful startups of all time, and how they plan to continue to build on that momentum. We talk about what it's like to build a startup in the early days of the dot com boom, and what it takes to stay on top of the competition.
Transcript
00:00:00.000
Your brain is not a good repository for memories, for thought, right?
00:00:03.340
It's for creative thought, and so you should be taking everything out of your brain,
00:00:08.040
putting it in a system that works, whatever that's, like, I happen to believe his system
00:00:11.720
is really great, but whatever system works, but just leave your brain to be creative.
00:00:16.420
Don't make your brain be this thing that you have to continuously pull things out of.
00:00:20.660
Like, it's just not, it's not the way it's designed.
00:00:30.000
I'm still waiting for the conference where they're going to put me on stage with a bottle of wine and a bottle of wine and a bottle of wine and a bottle of wine and a bottle of wine and a bottle of wine.
00:01:08.940
The best Natalie comes out after a glass of wine.
00:01:11.620
Just as long as there's enough time to let the alcohol
00:01:28.240
You guys have three products, Beanstalk, Postmark, Conveyor.
00:01:45.220
So we launched it, and then we kind of absorbed a ton of feedback,
00:02:01.260
Which is in the 0.0, like not a lot of companies
00:02:05.140
in the software space have been doing it for that long.
00:02:10.900
And Chris found out that I was one of the first Beanstalk
00:02:15.720
They see me, they're like, oh, Dan's that marketing guy.
00:02:20.360
And I was not early, but I went from Microsoft to Rails.
00:02:27.360
and Ruby and Mac at that point in my life, 2007, 2008.
00:02:51.040
is I manage what I consider the front of the house.
00:02:54.360
And so the team culture, obviously the business side
00:02:59.080
of things, and kind of marketing to some degree,
00:03:16.600
Build a successful software product with not really
00:03:22.480
Because I think timing and market plays a massive role.
00:03:25.900
And when we launched Beanstalk, as you remember,
00:03:35.800
No, I mean, it was, I laugh, because we have things
00:03:39.020
And we're like, apps are launching by the minute.
00:03:43.480
Yeah, and we would launch, when we launched Beanstalk,
00:03:59.720
They wrote about the integration with the Beanstalk
00:04:02.420
integrates with Basecamp because that was important for them
00:04:05.260
to have that connection as well, connection with other apps.
00:04:10.060
How much of that growth was that a lot of their early growth?
00:04:19.240
But was it early, like what other factors were happening
00:04:28.740
the idea behind Beanstalk, which is like hosted, yeah,
00:04:31.400
back then it was just hosted at Subversion, which was the kind
00:04:41.980
you had to host them yourself and do all this management.
00:04:45.480
And Chris was like, you know, every time we had to add a user,
00:04:48.320
He actually went to a bunch of friends and said, hey, you know, would you let me host your source code?
00:04:58.860
You know, that was like how unusual it was to have these hosted apps where you would, you know, store data or do critical things.
00:05:08.560
Yeah, we had fog bugs as like our task management, you know, installed on our, you know, computers.
00:05:16.300
And so that, our distribution was completely word of mouth.
00:05:21.300
And it was all around just the fact that, hey, this is a thing.
00:05:25.100
It was all early adopters, lots of Rails projects, actually,
00:05:27.740
because that was also the time of Ruby on Rails was becoming a thing.
00:05:30.940
And it was written in Rails, so it became a project that was written in Rails.
00:05:34.100
And so there was just like a lot of very natural word of mouth early to the market.
00:05:41.720
All these things that just were like, it was just natural, right?
00:05:44.920
Like, the people who were on the internet looking
00:05:46.620
for hosted services, and they would use Beanstalk.
00:05:51.800
There was something called CVS Dude, which was not even worth
00:06:01.800
Very similar, like, we launched it to Beanstalk customers
00:06:11.220
That's always been where we just find the most excitement,
00:06:13.860
is just building really great products for developers,
00:06:19.800
And we love building tools that we can use ourselves.
00:06:42.060
They're like, what's your go-to-market strategy?
00:06:49.280
Yeah, I was like, I don't know what that means.
00:06:53.900
There's like that, if you build it, they will come,
00:06:57.840
Even in the content, they call it peak content.
00:07:00.580
Like, creating a blog is just not going to get attention.
00:07:04.880
from a different perspective now and still very stubborn
00:07:08.760
But the growth has been just completely correlated
00:07:17.280
Like Postmark is a product that people really genuinely love.
00:07:23.480
So it created its own kind of energy around that.
00:07:37.580
But we live in Philly and have a few folks who also live in Philly.
00:07:41.820
So we've had an office in Philadelphia that kind of became
00:07:47.800
And we're actually moving to a new space, just smaller
00:07:52.900
But yeah, I mean, remote first, everything's remote.
00:07:59.760
And then in regards to that journey, 30 employees
00:08:02.840
from like the early days, and were you, what employee number,
00:08:21.940
And there was always contractors that kind of helped with it.
00:08:40.640
we used to get paid because we didn't make a lot of money
00:08:50.080
So we just had a house account, so that's how we eat.
00:08:52.800
We had this nice restaurant, nice Cuban restaurant in Philly
00:08:57.800
and like they give you a box and you just sign your name.
00:09:02.880
It was like, yeah, they were paying us for $2 food
00:09:05.420
for like $20 worth of work, but it's fine, it's fine.
00:09:09.160
Yeah, so I think, like, in terms of employees, when we started working together, you know, it was a transition.
00:09:22.120
That was the money we used to live so that everything else kind of flowed back into the business.
00:09:28.820
So it was, like, QuickBooks or helping write proposals.
00:09:30.960
And it wasn't the business really started to evolve when we got into products.
00:09:36.120
And that's where, like, you know, I took all the support.
00:09:44.160
And in, I think, mid-2008, it was making enough money
00:09:53.420
And we just needed, we weren't going to fire anybody.
00:10:05.160
And then the rest of the team was doing client services work.
00:10:07.820
And so we basically knew that we did not want to fire anybody.
00:10:11.060
And so we had to wait until it made enough revenue.
00:10:30.400
Especially for the bootstrap, where you said, look.
00:10:33.820
You're like, yeah, I get approached all the time,
00:10:43.880
and it's possible that it's because we got into the business
00:10:48.080
your security of your business lies in whether you can
00:10:52.500
comfortably, whether you feel like you're being rewarded
00:11:00.800
who just don't pay themselves, like pay themselves last,
00:11:04.740
Or they raise money and they, you know, they don't make a lot of money and salary because of all this like potential upside.
00:11:11.060
But what that does, it just weighs on you emotionally and it weighs on your life and you become very vulnerable to not the best outcomes, right?
00:11:19.000
Like a lot of these, you either have to continuously raise money because the financial incentive just gets further and further away because everything's diluted and you don't make, you know, or, you know, you're just like you're tired, right?
00:11:32.180
You're tired of the hustle or you're tired of all the work and you're not paying yourself.
00:11:35.680
And Chris and I have always paid ourselves because the whole purpose of this business was to support our family.
00:11:44.660
Yeah, any expense is coming out of my pocket, right?
00:11:48.700
Yeah, like any hires, personally, Chris and I are paying for it.
00:11:52.100
I mean, we obviously separate the finances and all these things, but it is absolutely an impact on us personally.
00:11:56.800
And what we've done to make sure that we can secure our position is we make sure that we pay ourselves
00:12:01.640
so that this way when we do get you know i don't take a lot of meetings but like we've done a few
00:12:06.360
where they were really strategic and we're like you know let's just hear what people have to say
00:12:09.560
and uh our number is so high and i tell the team this all the time our number is so high
00:12:15.240
because chris and i pay ourselves and like i don't need it yeah it's not like i'm not going
00:12:19.560
to change your lifestyle yeah and it's incredible the power that brings like and i i talk to people
00:12:24.920
about this all the time like in those conversations that we've had the instinct on the people you're
00:12:30.520
meeting with or at least in our experience the people that we meet with are really expecting
00:12:34.520
you to be exhausted just burn out poor and we'll take some really crappy multiple yeah and you're
00:12:42.600
and you're just kind of like i've actually sat at a table and they were like you guys must be so tired
00:12:47.320
and we were like no we're great no i just got off what are you talking about well that was
00:12:52.200
that's pretty sabbatical i do want to talk about that but but the face changed yeah because they
00:12:55.880
instantly like never mind I'm not I'm not scooping this up for real cheap and I
00:13:00.500
think that's a superpower right because we acquisitions are really sexy to talk
00:13:06.080
about but the numbers behind them a lot of times are not they're not great for
00:13:10.280
the founders so I for us it's just it's a very important thing and I tell it's
00:13:13.520
like my number one thing when I talk to founders like are you have well I asked
00:13:16.340
two questions are you having fun and are you paying yourself because those are
00:13:20.560
that's that's your security that's you that's the armor that you need to be
00:13:24.060
able to do this for a long time, because that's
00:13:25.260
people ask me, like, how do you do this for 19 years?
00:13:31.000
And is it an aspect of having to learn to value?
00:13:35.140
Do you think people don't value their contribution,
00:13:37.600
or they feel, or do you think it's just delayed?
00:13:42.520
Like, there's this whole, I'm growing this business.
00:13:48.320
And I need to make sure that, you know, everybody, you know,
00:13:52.120
That money could be used for marketing or whatever.
00:13:57.740
And inventory if you're in a traditional business.
00:14:00.920
And they miss the fact that the longer you do that.
00:14:09.320
But the longer you do it, the more vulnerable you get.
00:14:16.000
Yeah, all my friends are growing up and going on vacation
00:14:27.120
Yeah, like we make money, and that's really important for us.
00:14:29.960
And how do you guys, because you mentioned profit sharing,
00:14:35.480
Yeah, so our profit sharing removes anything Chris and I
00:14:37.640
take out of the business, so totally just pure profits
00:14:51.260
No, no, no, no, they see the whole, the full P&L is there.
00:14:53.560
But like anything, like I'll just withdraw, like our salary.
00:14:57.140
would draw everything out of the P&L so that they are not like.
00:15:04.300
So it's not like it's a blended, they don't really know.
00:15:06.740
I mean that I inflate the actual bottom line profits.
00:15:09.680
They're more than what like the P&L would show.
00:15:12.200
Because I just, I don't, they don't lose out on profit sharing.
00:15:36.020
except for a blended salary line for the whole team
00:15:41.720
and that way they can make their own decisions around growing
00:15:49.300
and it's been even more interesting so the last couple years we've run really
00:15:53.020
lean we've been growing the product postmark ahead of growth and like ahead
00:15:58.440
of revenue and so that's been a really I felt like a lot of pressure I don't
00:16:03.040
want them to be stressed out or upset like that's my stress like I know this
00:16:05.680
is the right decision but I don't and it was incredible to see the team like
00:16:08.300
really rally and be really supportive that yes we're investing ahead yes
00:16:10.960
profit sharing is really low but we know it's gonna get there and like there was
00:16:14.080
that that was really cool for me to see that we are in this together because
00:16:20.740
been around for 19 years, it's always been up, up, up, up, up.
00:16:37.760
And so for me, it's like, hey, I made the call, ultimately,
00:16:40.680
that we're going to invest ahead and lose some of that,
00:16:44.300
not have those profits for that year, year and a half.
00:16:58.860
that transparency really helps them see and feel a part of it.
00:17:02.780
And the downs are when they feel the most a part of it,
00:17:12.380
So having you and Chris in the business for this long is pretty rare.
00:17:19.240
I don't know if I could run a company with my wife, lover,
00:17:29.580
How has that impacted the dynamics of the work?
00:17:33.240
Or, like, how do you think of, like, the concept of integration
00:17:36.680
or balance around dividing and conquer between you and Chris?
00:17:42.980
How do you do it as an entrepreneurial mom?
1.00
00:17:48.800
is we're actually extremely good at different things,
00:17:54.240
So that just flows right into our personal lives.
00:17:57.480
And one of the joys of running a business together
00:18:01.980
is that as an entrepreneur, I really believe you never turn it off.
00:18:04.560
like i even if i'm not working like it's just somewhere in my brain thinking about it and the
00:18:09.580
fact that we can bring it home in a way that's empowering like i have two daughters right so
00:18:14.400
their mom's you know the ceo of a successful software company you know all these things like
00:18:18.960
that's empowering for them and so we talk about work at at home at the dinner table you know we
00:18:22.960
all go around the room and talk about our days how old are your daughters now i have a nine-year-old
00:18:26.500
and almost five-year-old okay but we talk about our days we do this thing called rose thorn bud
00:18:30.620
where we talk about like a rose a thorn and a bud from our day and ours are work on Monday through
00:18:35.120
Thursday and so they hear about people challenges you know because they know some of our team they
00:18:40.740
hear about projects we've launched and features we've you know and things like that and I think
00:18:45.100
it's really important and we don't compete in that way like we don't have two different businesses
00:18:48.620
that we have to compete for attention or whatever and then we we are very equal partners Chris and
00:18:56.360
I in every aspect of our life and that very much translates at home and there's no uh there's no
00:19:04.440
this is my job and this is like we definitely have things like I'll you know I'll figure out
00:19:07.540
what's for dinner but he you know he'll figure out like what the kids are doing with after
00:19:11.600
school activities and we're just we're extremely equal in our homes and that's just I think again
00:19:16.420
because we run the business together there's no equal yeah it just flows into the house we're
00:19:34.300
I don't feel like anybody's ever called me that,
00:19:39.920
Like, I do night routine every night, pick up the kids.
00:19:43.960
We swap the kids because they sleep in different rooms.
00:19:49.620
Like, it's not, you know, if I'm too busy for dinner,
00:19:53.120
And I just, there's no, there's really no lines.
00:19:56.760
And then how have you guys kind of leveraged the business
00:20:07.780
Because I know that my wife, you know, even when we,
00:20:10.120
this is early days of, like, having somebody clean the house,
00:20:12.560
she was like, there was guilt because it's, you know,
00:20:16.020
her mom, like, and her mom never said anything.
00:20:21.520
So then to go to the nanny, to the house manager level.
00:20:33.660
And we only fought over one thing when we were dating,
00:20:48.500
Like, so, you know, I can put the cup away tomorrow.
00:20:54.400
He cleans the house before he goes to bed so that it's like that.
00:20:58.820
And that was the only thing we ever fought about.
00:21:00.100
So one of the first things we did when we had no money was we had somebody come clean the house every other week.
00:21:08.300
And we basically looked at it like that's one less dinner out.
00:21:13.080
at but that meant we don't fight and that also meant that we got to spend the whole
00:21:17.720
day together so like otherwise it was a sunday and it was like all right you clean the toilet
00:21:21.640
we lived in this cool like and that was a choice right that's not a it was very much we could find
00:21:27.880
that money in just by not doing something we really didn't have a lot like we literally lived
00:21:31.400
off of my waitressing and and kind of hostessing is that a word hostessing yeah uh salary so it was
00:21:37.400
just a choice we made like that was an expense that allowed us to spend time together so we've
00:21:42.440
always carried that through because for me it's it's experience like you know i want to have those
00:21:48.920
those times with the kids and with chris and those experiences matter and i i try to choose where
00:21:53.800
our priorities lie so the kids had nan we had a nanny for both kids it's life-changing did you
00:21:59.600
have a night nanny no it's magical yeah but our kids slept through the night pretty early that's
00:22:04.960
not fair i'm sorry that's awesome though we can talk about parenting later my mom is
1.00
00:22:09.240
i'm i want to talk about now this is this is the kind of stuff yeah so i'm from russian so like
00:22:13.580
we actually did like a very strict schedule very early on like feeding yeah and didn't do the 3 a.m
00:22:19.660
feeding very early on figured it out real quick and they were yeah real fast but that was my mom
00:22:24.100
thank god for my mom i don't know she was just like at first i was like no i can't do that and
00:22:27.520
then like you're not sleeping for a week you're like i can do that tell me how to do that and
00:22:30.760
she's like here's how we do it and we just kept a really i'm i was better as a mom on a schedule
00:22:35.520
So for me, we would do feedings 6, 9, 12, 3, 6, 9, 12, and then skip to 3 a.m.
00:22:43.340
But that meant I would wake them up, so I wouldn't let them nap too long.
00:22:45.620
I'd make sure that they're fed so I knew comfortably that they got all the food that they needed.
00:22:50.980
And we did that with both, and that worked really well for us.
00:22:53.700
And what other stuff do you have support to allow you to?
00:22:57.480
Because what I love about it is, look, I'm spending money to buy time to then go spend with my family, or I'm going to work.
00:23:09.320
Chris and I don't have personal email addresses.
00:23:21.380
And I'm like, oh, no, no, I didn't mean, no, no.
00:23:25.480
Like, it's Natalie at Wildbit, and then there's a Chris at Wildbit.
00:23:48.700
There's a privacy security thing, and I couldn't separate them.
00:24:09.980
We have somebody who kind of almost like a house man.
00:24:12.500
You know, she takes care of a lot of the stuff.
0.75
00:24:15.100
You know, birthday presents for birthday parties for kids.
00:24:18.460
You know, like the kids go to get invited to birthday parties, helping me plan parties.
00:24:21.700
You know, just like stuff like that, ordering groceries.
00:24:24.320
Yeah, things that you'd have to do on a Saturday.
00:24:26.460
Yeah, I'm a big, I mean, we don't even have the kids do activities on Saturdays.
00:24:30.320
Well, the fact that you guys do the four-day work week.
00:24:39.660
There's a book called Deep Work by Cal Newport.
00:24:43.580
I send two books to everybody who comes to Wildwood,
00:24:52.100
I have a picture of the young Dan at a workshop.
00:24:59.460
He just did an entire hour workshop with our team.
00:25:03.300
I don't know why people don't get on the GTD way.
00:25:18.180
because my feeling is that I can do as much as I can
00:25:25.940
but it's every individual's responsibility to be individually productive.
00:25:31.860
And I'm a strong believer that, like, everybody does things differently.
00:25:35.160
Like, one of the reasons GTD never caught on to some of our engineering team
00:25:41.340
And they don't have these tons of projects that live in their life.
00:25:45.860
Where, like me, I'm always, you know, I'm juggling personal projects,
00:25:48.520
nonprofits, you know, boards, things like that.
00:25:51.500
And so, like, having that is the only way that my brain can function.
00:25:55.040
but the book to me is the methodology is extremely important but the perspective
00:26:01.080
or the the kind of the view that your brain is not a good repository for memories for thought
00:26:06.740
right it's it's for creative thought and so you should be taking everything out of your brain
00:26:11.640
putting it in a system that works whatever that's it like i happen to believe his system is really
00:26:15.740
great but whatever system works but just leave your brain to be creative don't make your brain
00:26:21.320
be this thing that you have to continuously pull things out of like it's just not it's not the way
00:26:25.720
it's designed right so i think so anyway that's why i send those two books but in cal's book
00:26:30.200
he talks a lot about the brain's capacity for the science around the brain's capacity for deep work
00:26:38.380
and so at wild bit everything is all we're just obsessed with focus work like it's everything we
00:26:43.860
do it's all around like you know i just believe so much in my heart that my job is to create an
00:26:49.340
environment where people can get their best work done and really push themselves past their comfort
00:26:53.000
zone so that they are really proud of their work and feel really fulfilled and so you can't do that
00:26:58.100
if you don't have the opportunity to actually do good work right and people tell me all the time i
00:27:01.820
do my best work at night i'm like blah blah blah it's because you're not working during the day
00:27:05.620
like you're distracted all these things so we've always had you know a very strong stance against
00:27:09.900
open office floor plans we've always had closed offices even when we had the philly space i don't
00:27:14.880
let remote worker remote team members work out of a coffee shop four days a week like they have
00:27:19.360
to have a quiet space so there's just a lot of stuff like that so when the the deep work book
00:27:25.200
is so so great because it gives you real perspective on like what it is that you get paid to do right
00:27:31.460
why are we here what is our job that that that work needs to be priority we have to create so
00:27:37.680
much space for it and so when he looks at like the science behind your brain's capacity for deep work
00:27:42.560
it shows that our brain is a muscle and after about four hours it's fatigued and doesn't do
00:27:48.060
good work anymore and four hours actually really hard that's writers and and and people who think
00:27:54.580
for a living right like who and if you actually if you look back right there's always a story is
00:27:59.020
like somebody wake the big writers wake up at 6 a.m they work till 10 and they're done right like
00:28:03.640
they're done yeah and Stephen King a bunch yeah yeah and it's like their day is done because they
00:28:08.280
know that they've that's the best you're gonna get from me today and that's amazing and so we
00:28:12.080
We looked at it and said, well, what are we doing for 40 hours?
00:28:17.720
And what is the, you know, are we getting our best work done?
00:28:23.260
So we did it as an experiment to say, I'll just drop a day
00:28:26.900
And it wasn't a forcing function in some ways to get the focus.
00:28:33.360
For me, it's like so productive because you're trying to get.
00:28:41.760
And most of the time, it's on the extreme to just see what breaks.
00:28:50.080
And so I think we just, we're big on just testing it and not hypothesizing all the ways in which it's going to fail.
00:28:58.160
It's like, let's just see what happens and what's the worst that happens.
00:29:01.420
So what was the byproduct of the four-day work week?
00:29:09.080
my team may be thanking you in like a week because i might do it i mean here's the thing i i think
00:29:16.220
we all make this is the same with like you know having somebody help you around the house right
00:29:21.100
those are choices we're making choices in how we spend our time and those and what we work on and
00:29:26.800
those are those are conscious choices everything you say yes to you say no to something else right
00:29:30.200
like they're conscious choices and so we looked at it and said okay well if we're only working
00:29:35.080
four days a week what are we working on and why and that became this like driving force right and
00:29:40.600
it's like where are we spending our time are you focused are you getting enough hours right are you
00:29:45.320
you know on a remote team in different time zones it's very uh it's not talked about a lot but
00:29:51.080
meetings are way more disruptive because they're in different time zones and they could really
00:29:55.560
impact somebody's ability to get into flow and have really focused work so my 9 a.m could be
00:29:59.880
somebody's 2 p.m. or somebody's noon right or whatever those things are and that could just
00:30:05.980
completely derail right like an 11 a.m. meeting for somebody in my view is almost a complete
00:30:10.600
derailment unless they're a morning person and they got like a solid couple hours in the morning
00:30:13.860
yeah right at 10 30 right like my morning's gone i'll do some busy work too brilliant right because
00:30:20.020
it's like what do you i want my creative time exactly and so you know really reimagined and
00:30:25.920
re-evaluated meetings and how we function and energy flow yeah i'm just such a focus worker
00:30:32.980
i love that you you um you didn't just do it for yourself but you said hey this is what i want for
00:30:40.880
people that want to work here and let me create that environment because yeah i wild bit is the
00:30:47.100
product of 28 really incredible people and i'm excluding kristen like like they are the reason
00:30:55.160
it exists they are the reason it all the products are as good as they are the reason our support is
00:30:59.140
world-class the i mean they're everything and my job is just to create an environment where they
00:31:05.520
can be really really successful i mean that's all that's all i do that that's why i exist right
00:31:09.820
to create this space environment so like it's all for them what happened when you turned off
00:31:15.600
slack for a month you know i bought slack a long time i thought this is a distraction i'm the same
00:31:23.280
like how to do email properly so that, you know,
00:31:25.080
and I don't like when they're super responsive.
00:31:29.880
Yeah, but it's just like, then Slack, I was like, oh,
00:31:33.280
I can see a few use cases where it makes sense to kind of
00:31:41.240
Did you guys ever use like Campfire back in the day?
00:31:43.720
So Slack's not interesting to me as a product in general.
00:31:46.060
Yeah, it's actually interesting that it's successful now
00:32:07.580
The Slack experiment is interesting because for us, this second time around,
00:32:15.220
that was super impactful where we realized how much we used as a whole the team uses slack to
00:32:23.220
procrastinate so it's not even the disruption like we're pretty good at keeping the noise down
00:32:28.700
everybody's got their notifications they'll plug in when they want it yeah but the distract the
00:32:33.200
procrastination enabler was wild and it was basically like i found myself people were saying
00:32:39.200
like i found myself faced with a hard problem right that part of your brain's like i want to
00:32:44.000
do a hard problem let me find something that feeds it right and they would like flip to slack slack
00:32:48.500
wasn't there and it's like oh i got up and went to take a walk and you tell me what's better for
00:32:52.980
solving that hard problem like scrolling through slack or taking a walk right i mean it's the same
00:32:57.720
slack's no different than like facebook obsessions and instagram obsessions i deleted all that shit
0.95
00:33:02.200
i don't have any of that stuff anymore and it's like they're just not valuable depending on what
00:33:08.020
you're going for but if you're going for the ability to have creative thought to work as
00:33:11.860
little as possible because you're getting such good work done then like that stuff is useless
00:33:16.920
the second time around so we learned a lot in that one week and everybody kind of adjusted their
00:33:21.820
expectations the second time around for the month we actually missed it and there is and so it's
00:33:28.760
back but we are a remote team and that is how we connect you know for better or worse and it's not
00:33:34.720
a good way to connect but there was just this feeling of loneliness that everybody had almost
00:33:40.240
collectively everybody had even if we weren't actively in it there was just that was a thread
00:33:46.120
that connected all of us all over the world to like a single home and that i think is still
00:33:51.780
really important but i just don't i don't want that to come off like slack is the solution to
00:33:57.580
loneliness and remote work because i very much believe slack is enabling loneliness and remote
00:34:01.440
work because so many companies are just relying on that to be like oh we have slack and a general
00:34:05.240
channel and a you know in a cat meme channel or whatever right like all this stuff but our
00:34:11.640
experience has been that you have to be really intentional in remote work and creating opportunities
00:34:15.720
for people to connect i call it like the intentional water cooler like you have to
00:34:19.560
really really work hard yeah all these things if you just leave it people i mean you basically get
00:34:25.720
a general head hey hey hey bye bye you know it's like i mean it's it's useless right it's completely
00:34:31.960
useless because especially in different time zones you know and if you're optimizing focus
00:34:35.800
work you don't want to have slack open all the time so for us only because we're obsessed with
00:34:41.180
that stuff like we had removed all the typical slack issues like having an inbox you know second
00:34:46.520
inbox where people are posting things you have to read back like we don't slack has always been for
00:34:50.520
disposable conversation yeah never for anything permanent never for anything that anybody ever
00:34:56.100
has to read back it's it's it's it's uh synchronous communication that's it it's not historical
00:35:02.700
anything and we err on the side of asynchronous as much as possible so that people can work in
00:35:07.940
their own time and on their own schedules so it was actually fine i mean we need we need something
00:35:12.120
that connects the whole team that was the big learning for me something that like is a single
00:35:15.820
thread that you know you just know that if i need it to it's kind of like a security blanket if i
00:35:20.440
I can go plug in to feel connected to the team.
00:35:33.200
How did you find the person, and what did they do to help you?
00:35:37.100
Chris and I have been going through this for the last, I guess,
00:35:40.200
four years, going through this journey of elevating the business
00:35:49.160
right it's like a mature thoughtful business that involves everybody that
00:35:55.940
doesn't you know if Chris and I fall out of an airplane like because that's a
00:35:59.120
risk I mean if something happens like you have 28 people who I don't want them
00:36:03.440
to have to just sell the thing okay right and like I don't you know I don't
00:36:06.620
all that so that is an extreme example but also like I want the business to not
00:36:13.520
need me like I'm a bottleneck in so many areas so that especially four years ago
00:36:16.580
So we went through this kind of big soul searching, and it's been like a full circle of everything.
00:36:24.460
And it started with really like, what are our roles?
00:36:27.660
Like there was before that, before that coach, before we started working through stuff, we were in every decision together, every meeting together.
00:36:39.700
We didn't have titles, and it was just Chris and Natalie.
00:36:46.580
everything and just because you didn't know any different no well you know
00:36:54.580
that coaching was very much like marriage counseling in a sense where it was i can see
00:36:59.220
that those are hard conversations that you know you you don't you got to tread lightly on them
00:37:04.660
you have to be really intentional around them like what do you actually want to do you know i
00:37:08.260
this is chris's business for a long time like that's how i always viewed it this is chris's
00:37:11.220
business he started it i came into it you know all these things and and having those like really
00:37:16.100
meaningful conversations were like no actually natalie like i don't want to do it i want you to
00:37:20.420
like run the company i just want to work on product like that's what you know and having
00:37:24.100
those dialogues around like you know chris will say like i don't think the business could ever
00:37:28.340
gotten to this point if it was just me like it was just him because i don't want these things
00:37:31.860
that we do you know i wouldn't be able to be good at these people things and culture things and all
00:37:35.700
these things that like i really enjoy so we're lucky in that way but the coach was really you
00:37:40.020
know one of his first things was like so tell me what you guys do here it's like well we do all the
00:37:45.140
of eggs and he's like okay well co-co-ceo is a thing but let's just you know let's keep working
00:37:50.080
through that and it's not even that he had like a process or it was just i was saying this to
00:37:55.960
somebody earlier it was the value of sitting down for a day focusing on the business i couldn't you
00:38:02.960
know i was paying him to come here so like i needed his help and i'm gonna make an effort out
00:38:07.840
of it yeah and just asking a lot of questions making us think about things and so that was
00:38:11.840
kind of the big first step was okay ceo cto got it this is your responsibility we like drew it out
00:38:16.300
we mind mapped it we did all tons a ton of stuff to just really grasp like what is that in a day
00:38:21.080
to day what is your team asking you for that they were much happier when they knew which one of us
00:38:27.140
to go to that was much that was a huge shift because it was like well product for example
00:38:32.660
chris is deep deep in the product and then all of a sudden it's like natalie jumps in
00:38:39.340
at the 11th hour and I have a really good eye for stuff
00:38:43.560
but they'll send me something at the end and I'm like that doesn't make sense
00:38:45.840
you know or that flow and it's like well should we have
00:38:49.640
it's just like this whole confusing thing and now it's like
00:39:03.780
a thing and then it was all the people stuff right like
00:39:07.880
flat until January of this year. So January 2019. Before that, we were flat. So it was like,
00:39:12.180
who's my manager? Was it Chris? Is it Natalie? Who do I talk to when I have a problem?
00:39:17.600
Right. And it's like, what do you do with that? That's just crazy. So that was really
00:39:20.340
huge. And then we just kept working through, I mean, as recently as last year, like through
00:39:25.200
working through an operating system. What, how do we want to operate? How do we plan?
00:39:46.040
And so I look at Wildbit as its own very important product.
00:39:54.880
Yeah, when you said that I didn't want to fire anybody
00:40:03.640
a lot of companies, it's an idea, a founder, co-founder,
00:40:07.600
So that idea is the thing that's holding them together.
00:40:19.540
Like we've had more than just the suite that we have.
00:40:28.980
I've never shut something down and fired people.
00:40:31.800
But it's also, we have incredible longevity on the team
00:40:34.640
And I really attribute that to the ability for people to move around and work on different things.
00:40:40.080
You know, there's like this real people have worked on conveyor who now work on Postmark, who've worked on Beanstalk, you know, and there's just this this flow.
00:40:47.440
And while we say like we don't put people in boxes.
00:40:49.700
So there really is this not just you can't be you don't have to be working on the product.
00:40:54.300
You can also if you don't want to be a developer, you know, or work in this stack, like, let's talk about that.
00:40:59.040
Let's figure out how to help you work in a new stack or or maybe you want to write for a little bit.
00:41:04.300
You know, whatever those things are, we try to find out.
00:41:06.160
But because we have the space and, like, the capacity to say, hey, there's this and there's this.
00:41:12.420
So you get a little more startup-y here, a little more growth-focused here.
00:41:16.760
And you can really just, to me, that's not only diversifying our risk, but also it's creating an environment where people almost can get new jobs and not leave wild.
00:41:31.260
As you look back over the 19, almost 20 years, well, not 16, sorry,
00:41:37.100
but it'll be 20 years, 16 years being CEO, co-founder with Chris,
00:41:41.860
who did you need to become to continue leading this organization, like the company?
00:41:54.300
So you go, I went through this whole, you know, I'm actually really young.
00:42:00.520
And so like when I said you just turned 27, 33, you never told us, we didn't ask 33.
00:42:11.000
And so like there was a tremendous amount of imposter syndrome that I struggled with
00:42:17.520
I'm also not a developer and I'm running in, you know, I'm pretty knowledgeable now
00:42:21.740
because i've been doing this for so long but i'm not a developer and so there is just a tremendous
00:42:26.640
amount of imposter syndrome and with that comes that insecurity of like are the things that i
00:42:32.960
really strongly believe in are they valid you know and and i you know i can say now that like yes
00:42:41.520
like so much of what wild but is is like my my beliefs and how people should be treated how
00:42:46.420
how work should should happen why you know the the kind of what i call like the audacity to think
00:42:52.840
that we can be responsible for 30 families right and and that's a lot of people and like all these
00:42:57.820
things is is very much for a long time was this i just i felt really insecure about who am i and
00:43:04.820
why am i why do i think i i can do this and there's like just a tremendous growth that was
00:43:10.700
really necessary and it was hard at times I think what's happening now is I'm realizing that I've
00:43:17.100
also had this very singular experience where I you know I've worked with people who have to say yes
00:43:24.440
to me right let's just call it like they obviously we have disagreements all these things but at the
00:43:28.060
end of the day I'm their boss I've created an environment in my community you know in this
00:43:33.400
space where people respect me and listen to me and all these things and that's not really the
00:43:37.520
real world like there's a lot more I can and I should experience to not be in that space so I've
00:43:43.700
been trying over the last two years really to get out of to create opportunities where I'm not just
00:43:49.380
solely like in this space wherever you know my thoughts are really great and everybody loves them
00:43:53.500
and it's like okay cool and start making myself a little more uncomfortable again and almost kind
00:43:58.240
of creating that imposter syndrome again to to see how better I can develop and being a better
00:44:03.200
leader and a better, like more well-rounded person. So I've been doing some work on some
00:44:08.760
nonprofits. I'm the chair of the board of like a small nonprofit school that I'm really passionate
00:44:13.740
about. And, you know, that's an example where I'm nobody, right? Like I've got 15 volunteer
00:44:20.580
board members who are really excited about the school, but they have their own jobs. They're
00:44:26.040
very successful. You know, there's, I got to get on the phone and talk to them, right? I'm not like
00:44:31.200
And I do this thing called EO, which is Entrepreneur's
00:44:36.440
that you meet with seven or eight other entrepreneurs,
00:44:40.340
That's the whole mission is that you're in different industries.
00:44:45.060
But we have the same problems, but in a different lens.
00:44:46.980
And that helps ground me a little bit to be like, yeah,
00:44:52.960
And those, I think I've been trying to force myself,
00:44:55.500
and I enjoy them very much, but trying to force myself
00:44:57.580
into these other experiences so that I can be more well-rounded.
00:45:02.780
I was having a conversation with somebody recently about how we've built this
00:45:06.560
business of people that like we've surrounded ourselves with customers and
00:45:10.760
employees and vendors, everybody that we like, that we respect, right?
00:45:14.960
I don't allow nonsense. Like our 10th value is no, don't be an asshole.
1.00
00:45:18.420
Like I just don't allow, I don't allow in my personal life, right?
1.00
00:45:21.420
Like, you know, I don't have friends with drama. Our family's really stable.
00:45:24.900
like we when something happens that is outside of that it pierces me like completely paralyzes me
00:45:32.100
I'm just I don't have the experience like if somebody's trying to pull something on you know
00:45:36.800
or like we're negotiating something or something and the person's not ethical yeah I'm I lose it
00:45:42.920
I have no like I cannot I don't have those experiences that people have to be able to be
00:45:48.540
like okay I'll deal with that and I I don't that's probably not like I have to start building that
00:45:54.320
thicker skin to have those experiences to be better at reacting to them to to look at them
0.64
00:45:59.540
as Ray Dalio sitting like as another one of those right like I need to start having and so that's
00:46:03.580
been really important with bigger problems which is different problems right I you know I was the
00:46:08.920
conversation I was having was like talking about negotiating like a real estate thing and you know
00:46:14.020
the person at the other end of the table wasn't was you know maybe they read art of the deal I
00:46:18.940
don't know but they were very much like I'm gonna squeeze every last ounce out of you and it's just
00:46:24.020
the way i work it's not the way i think it's like i'm happiest at a deal we're like both excited
00:46:28.820
and we're like yeah like this is great right and i'm a great negotiator that's not the point but
00:46:33.220
it's always around like let's let's come to something that we're all excited about
00:46:36.660
and in that scenario i was basically like just take it i don't i don't it's just too much like
00:46:42.100
too much it's too much for me i don't want to deal with that type of person i'll never deal with you
00:46:46.740
again and like that was it i'd like to be a little better at handling that because i probably you
00:46:53.800
But those are the kind of experiences where, for some people, it's just run-of-the-mill.
00:46:58.640
You know, I always have these conversations where I get, like, how can this person be like this?
00:47:01.840
And I'll talk to somebody, and they're like, what do you mean?
00:47:08.520
But I just, I think it's just a, it'll create a more well-rounded person.
0.84
00:47:12.640
It'll make me a little bit more able to react to these things so that they're, so that they feel as natural as some of the things I deal with at work.
00:47:23.800
is like, oh, I have to deal with this people thing.
00:47:54.060
That's the only one, just Natalie Nagel on Twitter or Natalie Wild.
00:48:01.720
Well, thanks for watching this episode of Escape Velocity.
00:48:05.660
Be sure to like and subscribe and leave a comment with your biggest insight from our conversation.