Quit your job

Paul and David talk about the early stages of commitment to your startup (i.e. quitting)

What is Bad Startup Advice?

Bad Startup Advice is a parody of the ego-bloated founder-worshiping world of venture-backed tech startups.

Each episode begins with authoritatively phrased (but ironically bad) advice on difficult & nuanced issues every founder struggles with. After the jokes, we put our serious hats on and discuss the topic more honestly.

Your host is Paul Koullick, founder at Keeper. Guest appearances on every episode of other venture-backed tech founders.

Paul: Hey David, I've
got my startup idea.

Should I quit my job?

Yeah.

,
Thank you so much.

.That's really helpful actually.

That's really, I really, I know
you're really busy, so I really

appreciate you taking the time.

Welcome to Bad

David: Startup advice.

Paul: The structure of each episode
is that the beginning we're gonna

make it sound like we know everything,
and we're gonna give you the worst

possible advice we can think of.

And then we're gonna transition
and we're gonna just give the

regular version of advice.

Today's episode is focused
on whether you should quit your

job , so onto the bad advice.

So

David: Paul

.
Here I am at Google working
from 11 to 3:00 PM every day,

and it's but I just have this itch

Paul: look, so what I always recommend,
is, you should have quit yesterday.

The thing about a startup is in order
to quit, you don't need an idea.

You don't need a co-founder.

You don't need money.

, you don't even need a plan.

You

David: just need

Paul: to quit

But you have to do more
than that too, right?

Because you are committing, you
need to create the space in your life

for brilliance, you gotta cut out
your girlfriend or your boyfriend.

Yeah.

You can't, you don't have time for that.

And look, they'll get it.

You just need to explain like, you don't
have an idea yet, but you will soon.

And they're just taking
up too much of, and

David: they'll, there will come a
point in your journey where they

can come back into your life.

Yeah.

Like you've iPod.

You can explain that to them.

Yeah.

They'll get it.

Paul: Just tell 'em to wait
I don't know, 18 months.

18 months.

And then you can get back to together.

It's pretty normal.

So you gotta cut off
your partner obviously.

You also gotta cut off your family.

Family.

Family doesn't help in
these types of situations.

You're gonna be fine if you got a kid.

It's not too late to put
them in to drop 'em off.

. Yeah.

So I, the thing is it takes commitment

So let's talk about what
you're clearing out space for.

In, in one word, it's brilliance.

So what I usually do, so you
wake up in the morning, you put

on your black turtleneck, right?

You do your gratitude journal,
you meditate for six hours, right?

And then you just sit there and you think,

so you're just ideating
for, at least three months.

And at this point I, I try
not to leave the house.

And I just sit right on the toilet.

And that way if I do have happen to
have excrement that isn't brilliance

and startup ideas, then it just,
I, it's just super efficient.

I don't, there no, there's
no interruption of your flow.

I like to actually, write it to the
press release that I will now be

starting a billion dollar business
and that I cannot be reached, that all

of my prior friends are just hangers
on my family, my partner, all that.

And I try to just go ahead and
announce to everyone just so

that it's clear what's happening.

I, I would hate for it
to turn into a situation

where, , they try to reach out to

David: me.

Yeah.

And what channel do you prefer?

So do you use LinkedIn

Paul: or do you use Twitter for that?

So all of the above YouTube and Twitter
and TikTok and Instagram and but I'll

also just travel around the country
making speeches because it's old

school, but I think there is a magic
to handing out your business cards.

So my business cards will just
say, Paul, a hundred x founder.

A hundred x founder.

Yeah.

Yeah.

Idea inbound.

Should we transition?

Yeah.

Okay.

. Cool.

Let's talk earnestly.

. So here's the earnest version
of should you quit your job.

There's a lot of doubt and
self-confidence quandary you're

early stage, it's really hard.

And so people use quitting as a way to
bolster their own confidence, right?

It's a way to show that
they are committed, right?

See, they've quit their job.

And it's unfortunate because it
doesn't, quitting doesn't really

help you like with some of the
really big, hairy difficult things.

In fact, it makes them a lot harder
because now you have a clock, right?

Yeah.

Maybe we can share our story
of how we started Keeper.

. But let me share, my story before you.

Okay.

I was 25, . I

was at this company called Stride I, had
worked there for two and a half years.

And so I think I did the thing that
we devoted all that bad advice to,

which is I quit without an idea.

I quit without a co-founder, and I
announced to all of my coworkers and

all of my friends that I was starting,

yeah,

Paul: I actually, I did make a
speech to the company . You did?

I did, yeah.

On my departure, I, in my speech, I said,
okay, I'm now going to be a founder.

And I Oh, you gave a speech
or you wrote an email?

No I gave a speech.

It was a give a speech.

Yeah.

They gave me the microphone and I
used that time in the spotlight.

To announce to everyone that I was
gonna be, wait, we're no longer

the satire part of this podcast?

No, this is what I actually did.

I see.

Yeah.

And, let me tell you, David, it felt
so good to quit . I felt that day

or maybe half of that day leading up
to the decision to quit felt great.

Yeah.

And then it just went downhill.

, so here's what I, here's what I did.

I started interviewing for jobs
right away cuz I was just scared.

, I was scared and rightfully so
because I didn't have anything.

So right away I was already distracted.

I just felt the pressure every
week I've got, like I, I talk to

my parents and every week they
were saying, oh, how's it going?

Is this turning into something?

And every week I had nothing.

David: So how much time did you actually
spend, I don't know, coming up with

Paul: ideas?

Yeah.

So I probably spent a month and a half.

Don't get me wrong I had an
idea, it just wasn't thought out.

I hadn't, I had a Google document
that was a page and a half long that

described how I was going to build
up some product analytics thing.

And it's very difficult on that
stage to like you, you start to

meld your own ego with the idea.

And so I felt very sensitive.

When people ask me for details, I felt
like I didn't really want to, I just

didn't have everything figured out.

So I didn't really wanna explain it.

So I had this Google doc,
but it was a little abstract.

Yeah.

So I was doing that.

I even then took a vacation.

So I told myself that I should
take a week long vacation, cuz

I've been working hard for so long.

I was working super hard up
until that point, and it was

the worst vacation of my life.

I went to Mexico City and I sat inside of
a hotel room for eight days and then the

other thing I did is I did hustle, right?

I did want to start a company,
but I realized that I am

someone who needs a co-founder.

I realized that I just, I don't know,
I don't have the mental and emotional

fortitude to go off and do this on my own.

So I, talk to every one of my friends
and acquaintances, and I tried to get

them to quit their jobs . And as it
turns out, when it actually comes to

getting someone else to uproot their
life for you, it's very difficult.

And it's one thing to be talking
about it and say one day, and it's

another thing to say, do it right now.

. Especially when they don't have
any investment in it, right?

Sure.

People, other people in your life
might wanna be founders, but they don't

wanna work on your shitty idea, right?

So I was caught in between this
rock and a hard place where, , I

needed to sound confident.

Like I knew what we were doing.

And so I wanted to pitch my idea.

And then everyone I was pitching
the idea to was like, oh, cool, I

don't really wanna work on that.

, let alone quit my job for that.

It's

David: also the timing thing.

You can't get someone to quit
like at that exact moment,

Paul: generally.

Yeah.

So that was my personal story there.

I ended up getting another job
and you ended up getting to work

on the thing you wanted to work
on, which was the amplitude.

Yeah.

That actually, that, that
is funny how that worked.

Yeah.

I realized that I had this passion for
product analytics and then I went to

work for a product analytics company.

And, at that point, I got
a little smarter , right?

So I had made a huge fool of myself to
everyone I knew, and I felt terrible.

I I had been utterly humiliated.

, but I feel like I did learn something
and I learned that I will not quit

my next job, until I actually
have some semblance of a plan.

Yeah.

And so I did, I went into Amplitude
with a, commitment to working on the

startup and just doing nine to five.

So it was the first time ever that I
had just I had a job and I did my job.

I didn't go overboard.

I didn't like, try to get the
fastest possible promotion ever.

I just did my job.

You felt like you went overboard,

David: or you went over the top

Paul: at the other two?

Yeah.

So I think coming outta stride, I quit
only when I was I was so exhausted.

I was like putting my weekends
and my nights since this company,

this startup or my job rather.

And so when I quit, it was just like
a finally some silence and relief and

I was telling myself that the reason
that I had to quit was cuz I couldn't

possibly scale back my work , at Stride.

And I actually think
that's a common fallacy.

I've heard other people say that too.

It's oh, this job I have is
taking too much bandwidth.

Emotional and mental bandwidth.

And the reality is no, I could
have scaled back my hours at Stride

and I could have made it work.

. But I just, I felt easier to
just So you quit more out of

frustration, burnout almost.

Oh, for sure.

Yeah.

I quit entirely out of
ego and frustration.

Yeah.

No, that makes

David: sense.

Paul: So then continuing
on the chronology here.

So I was at Amplitude
for exactly one year.

Enough to get stock options.

Nice.

And during that time, David
reached out independently.

Oh yeah.

. You remember what happened exactly.

David: I like reached out
to just what was the deal.

Paul: You, I think you said you wanted
to potentially wanted to start a company.

Oh, I think you were in the same kind
of like ambiguous place that I had.

but at least now we had
a little bit of headway.

We both knew that we were maybe interested
in this by the way you told me that you

were potentially interested in serving
a company or going to grad school.

. I see.

Or getting a new job.

It was one of those three, right?

Oh, I see.

Yeah.

Okay.

That sounds about right.

And it was for me too.

I like the thing is no one like, yeah, I
don't know very many people who are just

like, this is the only path for me ever.

Especially these, if you're a
whatever ambitious founder type,

you're gonna have optionality.

But we had this, we had the
very seedling of commitment.

Yeah.

David: I had finally reached unlike
Paul, I had only been working at

one job since college, and I was
finally getting rather tired of it.

So I, I was definitely itching
to, to do something different.

Paul: So we were both running away
from something, actually that is true.

. It's of undeniable.

It's not like we were
running towards taxes.

This is true.

This is true.

It wasn't like

David: we had a dream.

Yeah.

Paul: and candidly, I think a lot
of, there's this stigma associated

with Oh, you want to be a founder?

Just cuz it's not, cuz you love
the mission of your company, it's

because you just want to be a founder.

Yeah.

And I think the answer is,
yep, , that's most people.

It's definitely gotten

David: more, I think now
that the that's true.

Yeah.

It's partially because being
a founder is now pretty sexy.

Like it is an NBA alternative
I think for some people.

Paul: Yeah.

But so I think if you fall into that
camp and be honest with yourself, right?

If the actual reason you wanna start a
company is because of like ego stuff and

because you hit your job, that's fine.

, just take it slowly, don't do
what I did basically at Stride.

So David, what happened next?

After we got into, got in touch,
this was about a year before

we actually started Keeper.

Yeah.

What happened next?

We started just

David: working on random stuff.

I don't know if you remember this,
but for a very short period of time.

. We were working on my like
social media trading app.

I do

Paul: remember.

Yeah.

David: I think more than like the fact
that was an actual business or something

that we were, like, it was a test
drive of like our working relationship.

We we actually made some
design mocks together.

We talked to some folks.

So by the time we worked
on the next thing, we had

actually already been in touch

Paul: like for a couple months I think.

Yeah.

Yeah.

And okay.

Just for context, David and I actually
are friends since high school.

Like we were classmates in
high school and we were friends

there, so we had a backstory.

but that wasn't a professional backstory.

It's not like we had ever, maybe we
had worked on some projects together, I

don't even think we had in high school.

Yeah.

To be honest.

So in some ways like it's
almost worthless like

being friends with your founder, it's
fine, but it's not exactly like the thing

that's going to define your success.

Yeah.

I think I, it, it helped me respect
your, like I knew David was super smart.

I knew like that Sure, that helps.

But it wasn't that different than
I think if we were just coworkers.

Yeah.

So let's talk about that phenomenon
that happened with us, where we

worked through four different
ideas together, all on the side.

I think that at the very beginning
of the journey, all you have is ego.

And it is gonna power you
for a little ways, and you,

it's actually of useful fuel.

But what those, the reason why we had to
iterate so many times to get to keeper

was because I do think that part of that
ego spills into the way you pick ideas.

And there was an element
of this is my idea.

. Yeah.

This one's, so David obviously
has a background in trading.

Yeah.

And I've had a background
in consumer software.

So I think we went back and forth.

It was like now David's idea.

Get to go.

And now, and yeah.

Yeah.

I think we hadn't decided, had we
decided who was gonna be the CEO

and who was like, no, we hadn't re

David: we were just building
stuff, which frankly was actually

of my goal at that stage too.

Yeah.

The whole like, oh, is
it gonna be grad school?

Is it gonna be a new job?

Is it gonna be.

being a founder, I was okay, I'm gonna
learn how to code like everyone else.

Oh yeah.

That was

Paul: My deal actually.

You were learning how to code.

Yeah.

But I do think that over the course of
those four different startups, we gained

humility, and we gained a bit of humility
nothing's easy, there's no free lunch.

I think over time you just,
okay, this didn't work, this

didn't work, this didn't work.

And then by the fourth time,
you're like willing to do anything.

Yeah.

Which is actually the perfect place
to be if you're gonna start a company.

Cuz usually the things that are exciting
and fun are about terrible ideas.

Yeah.

Yeah, exactly.

You start, so for us, we started
off just picking random stuff, we

were like we don't know anything
about this, so that's perfect.

So let's go with that idea.

Yeah.

And Yeah.

And slowly got the ego
kind of pounded out of us.

Yeah.

Over time let's talk about our schedule.

How did we actually do it?

We at the

David: beginning we actually just
had a call basically once a week,

Paul: At the very beginning.

Yeah.

Maybe for the three months.

Yeah.

David: And we would just
do most of the stuff async.

It would just be like, we had a
meeting, we'd be like, all right,

so this is the current idea.

Here's the list of things
that we need to do next.

Yeah.

And we would just do them and then check
in over, Facebook messenger or whatever.

Paul: and there was a process here
and I think actually maintaining

a process is really important.

what we needed to do was we needed
to de-risk and it was half of it was

de-risking, half of it was like waiting
until we were tired of it basically.

But over time we would do these check-ins
every week and, one person's job was to

build like an mvp and the other person's
job was to like, or maybe share a job,

was to find people on Craigslist and
show it to them and get their feedback.

And then after, after four weeks, you're
like, okay, this is clearly not working.

Yeah.

No one gives a shit about this idea.

Yeah.

And

David: you're, yeah.

Paul: Cool.

So the first three months were less
committed and then I think there

was this like ratcheting it up.

It's asking someone to be
your girlfriend, , where.

. David and I were both,
we had our optionality.

David, I think was, you were
applying to grad school, right?

?
David: Yeah, I I was like taking

Paul: G e g E.

Yeah.

And I was just interviewing
with different companies.

At one point you got a job.

Yeah, I got an offer at one point.

Yeah.

And so I think we had this moment
where we said, okay, let's take

this relationship to the next level.

And we did have serious commitments.

We worked, I worked, I left
work at five and I went to

this cafe called Workshop Cafe.

It's basically a co-working
space, so it's close, right?

It's, yeah, it's bankrupt, but, and
I would go there and I would work

till 9:00 PM every day, five to nine.

And on one day on the weekend.

Yeah.

Pretty much all day.

And that's, and so we we weren't
on a call the whole time, but

we were working the whole time.

Yeah.

During those hours.

And it's serious commitment.

And I was only able to do it because I was
able to set my, my job on the back burner.

, but that it was like six
months of that, right?

Yeah, that's right.

David: Yeah.

I was checked out for
a long time for work.

Funny enough, I was
continuing to do well at work,

Paul: supposedly Actually,
that's really funny for me too.

I got promoted.

Yeah.

And I got like the Ampl
Award or some stuff.

Wait, seriously?

Yeah.

No, I was like a model
employee for some reason.

I think it was because I cared less.

I got promoted too.

,
David: do you remember this?

That's how I became head of
like analytics and execution.

I like

.
Paul: This might be a life hack.

Yeah.

It turns out I cared so much about my job
before that, that I just was worse at it.

Yeah.

But yeah, it's funny that happened.

Some of my best like career highlights
happened during that checkout.

No, me too.

David: That's actually what's insane.

Paul: Yeah.

Yeah.

Yeah, so we were, we had six
months of real diligence and you're

holding each other accountable
and, and I was dating my.

El Paa, my wife at that time, and I did
have that conversation with her about

listen, I'm gonna do this every day and
we're gonna see each other on Sundays.

, and that's what we did.

So let's talk about the final.

So let's talk about keeper,
how that actually started.

So we had gone through three
ideas and I think we were pretty

frustrated at that point, right?

We were like, how did you remember
how you felt at that point?

Yeah, I was

David: Yeah, it was basically, this
was right after we had done the H one

B and we had kind had called it off.

Yeah.

And we kinda had nothing.

We had no path for it wasn't like
we had this long stack of like, all

right, we're definitely gonna try Yeah.

X, y, and Z.

We were like, just like, all right,

, Paul: I think that we were at the
perfect state of willing to do

the thing that is obviously what
we should have done, the thing that

we actually had some expertise in.

But from the beginning I was
like so basically, okay, the

context here is Keeper is a
tax app for freelancers, right?

And I happened to have expertise
in that because I worked at Stride.

I had basically built a sim, a product
for a similar audience at that company.

And from the beginning I was
like, oh, I don't want to do that.

That's, that's boring, that's hard.

But then over time, like by the time
we were at our fourth idea, I was like,

okay, you know what I like, maybe we
do something that's not that sexy.

Maybe we do the thing that like we
actually kind know something about.

So we came up with this idea
to, automate expense tracking.

That was basically the concept is,
if you're a freelancer in the US you

have to track, business expenses.

And that process is laborious.

And we thought, okay let's
try to solve that problem.

And we actually came outta
the gate with an idea.

We didn't really start with like
blank slate let's go talk to users.

Because I had already,

David: You, we, very early on you had
the concept of let's just text them.

Yeah.

Every day.

Yeah.

I

Paul: think I was inspired by digit.

remember that.

Yeah.

The like savings, automatic
savings that company s hub.

I think they are around, they text you

David: every day with a different greeting
from the like 400 different languages.

Bonjour,

Paul: you say 4 cents day

Yeah, exactly.

So that was the inspiration.

And then it was like applied
to the space that we, uniquely

had knew something about.

And I, the other brilliant

David: part of the texting
thing was that it actually was

somewhat easy to build the mvp.

Yeah.

Yeah.

Building an app would've
been much more difficult.

Paul: Yeah, for us, and I guess
time, here's some, advice is

if your MVP requires building
an app, don't try, don't do it.

Try to try to find some creative way
because it's just so much work to, so it

takes so long to actually build something.

So yeah, try to find a way to not do that.

In our case, the idea for the product
was, you connect your bank account

using plaid, and then then our magical
software will automatically identify

tax write offs among your expenses.

And the interface would be text message.

So you wouldn't even have to
like, do anything, you'd just

reply yes or no to a text.

And the beauty of that idea is
that all of the hard stuff we

could just do manually, right?

So we, all we built was a, it was a
website with a button that connected

to plaid and then David and I would
just look at your expenses every day

and text you in the beginning it was
just, we created a Google Voice number.

I, in fact, I'm sure we
created a Google Voice number.

Okay.

Yeah.

And if you just, every day
we would just text you.

And I remember it was really I think
all we were trying to de-risk at that

point really was would anyone reply?

Would anyone reply?

Yeah.

And second of all, is it even possible
to look at someone's purchase transaction

history and decide that something was
a tax deductible business expense?

Is that even like something you can do?

Where do we get these users?

David, Craigslist.

Oh, that's right.

Yeah.

So we, okay.

Yeah.

So we ran should we even be saying this?

We ran these fake ads.

Oh yeah.

We figured out, we hacked Craigslist.

We posted in the jobs
section of Craigslist.

So basically someone who's
looking for a gig and instead

of a gig, your tax software.

It was tax software.

We said, Hey, we will pay you 20 bucks
or something to connect your bank account

to our like super sketchy website.

And it's amazing what
people will do, honestly.

So we just, we would hop on a quick call.

We would confirm that we're like
real people and smile and wave.

And I guess that conveyed enough trust for
people to link their bank accounts to us.

Yeah.

David: We had some, like those
first 12 users were real people.

That's

Paul: what They were real people.

Yeah.

And it was nice that it wasn't friends and
family, cuz I think the hard thing with

friends and family is users is they're
not really gonna be honest with you.

Yeah.

So yeah, these were just random
people we found on Craigslist

so we had our 12 users and that was it.

We also had to spend like

David: at least 30, 40
minutes a day texting them

,
Paul: right?

Yeah.

And that 30, 40 minutes a day turned
into three, four hours towards Yeah.

Until we actually automated things.

Yeah.

Yeah.

So we would do that every day and then and
that's what we applied to YC with, right?

Yeah.

It was just, we have 12 users and
the retention is 95% or whatever,

David: 11 outta 12.

I don't even think, I don't think
we had to give retention the first

Paul: It was bullshit point.

Yeah.

Yeah.

But I guess we, I don't know.

I think YC probably, that's
probably what they're sniffing for

is did you actually try it ? Yeah.

And we passed that sniff test.

I think we had good,

David: Yeah, so we applied the YC
and we got the interview and I think.

if I had to guess.

I think we had good foundry chemistry.

Yeah.

They recognize that we had
known each other for a while.

Yeah.

We did actually build an M v
MVP and could talk credibly

about a couple of early users.

It wasn't all made up.

Paul: But we basically, this whole time
during applying to YC for six months,

where we worked from five to nine every
day this whole time we were employed.

Yeah.

And I think we had started to
make plans for did for quitting.

You had your end of year bonus.

Yeah, that's right.

So David did, we had to
wait for David to get paid.

But I think I had it was one of those
commitment things I had said, I will quit.

Yeah.

No matter what.

Yeah.

And thankfully we, we got into YC and we
got some funding but yeah, it was a long

time before we actually quit our job.

It was probably like a whole,
it was close to a year.

A year.

Yeah.

Yeah.

Yeah.

And it probably would've been longer if
we hadn't, if we hadn't gotten to yc,

we would've dragged out yeah, for sure.

Yeah.

It was a year, but it wasn't
a year of oh, let's like joke

about it and talk about it.

It was a year of working
pretty intense hours.

Maybe the most I've ever worked.

Yeah.

David: Those first 2018, 2019 were

Paul: both pretty tough years.

Yeah.

Yeah.

Yeah.

So that's what I mean by the rage is
useful if you channel that ego and rage

into just working really hard, I think
that's a good way to get started, yeah.

David: I think a lot of founders have
a chip on their shoulder or Yeah.

Some reason that they feel the need

Paul: To go on this ridiculously
difficult, totally journey.

Yeah, totally.

So just channel that and you and into
something like kind of productive,

because it's not gonna last forever.

So in our case, David and I were
in different parts of the country.

David was in Chicago.

I was in San Francisco.

It was a big deal for you to move.

David: Yeah.

. And in keeping with our Batar
ice, I basically did abandon my

girlfriend cuz she was in Chicago.

Oh yeah.

For Roxy.

I moved to San Francisco and then we had
to do this long distance thing where we'd

have to fly to each other every three

Paul: weeks.

Yeah, but you're still
together, so That's true.

So yeah, obviously the best time
to quit is when you have funding.

You have your co-founder, you have your
idea, you have an mvp, you have an mvp,

you have some proof that it's working.

That's the best time to quit.

But if you can't do that, then
keep trying . I mean, maybe,

I mean, that might look okay.

I also know a lot of people who
quit and then figured it all out.

But it, boy is it hard.

I mean, those people,
like, they're troopers.