What's up, everybody?
This is Cortland from IndieHackers.com, and you're listening to the IndieHackers podcast.
More people than ever are building cool stuff online and making a lot of money in the process.
And on this show, I sit down with these IndieHackers to discuss the ideas, the opportunities, and
the strategies they're taking advantage of so the rest of us can do the same.
So we're going to talk about water cooler trivia.
You've been emailing me for like a year and a half, and I almost never invite anybody on
the show who comes up for email every now and then.
But here you are.
And it's because of the way your emails progressed.
It was like 2019.
Hey, Cortland, just an interview on IndieHackers, making like $10,000 a year, I think it'd be
good for the podcast.
It's like, oh, wait a little bit.
And then like every few months after that, it was like up to $50,000 a year, up to $100,000
a year.
What was the last email you sent me?
I think you're like $200?
Probably $200 or $250.
I don't know when I sent you the email, but yeah.
Yeah, $250,000 a year.
So I was like, oh, Jesus, Collins crushing it.
I don't know what happened during the pandemic, but like your app is blowing up.
What is water cooler trivia?
So water cooler trivia is a weekly trivia app.
It's basically that simple.
I love that I feel like I can explain it to my grandma because my grandma gets my monthly
investor letters and reads them and always gives me feedback, which is lovely.
But we send a weekly trivia quiz to work teams.
And so it's typically over email or it's over Slack or Microsoft Teams.
And you answer 10 questions or more or less, it depends how you customize it.
And then the next day the results come out.
So it's sort of asynchronous.
Fill it out during the day, Monday results come Tuesday and there's a leaderboard over
time and it's just something that's fun and easy.
I think that's not a chore.
And so people have latched onto it and it happens to work really good in both virtual
or physical or hybrid virtual physical or whatever we're going to call it moving forward.
But it was just a random idea that was what we really called beer money idea, like bootstrapped
it for two years with friends two and a half years before any of us took a full-time lead.
Yeah, it is super cool.
I'm on your website right now and the description really is as simple as you make it.
It says your team's new favorite weekly ritual.
You choose a trivia schedule and categories.
We write the questions and we grade the results.
It's all automated.
It's asynchronous.
Couldn't be easier.
And you've got like some pretty cool customers on here.
You've got Strava, Amazon as a customer, Impossible Foods, the Dallas Mavericks.
I'm just imagining basketball players playing trivia, but I'm sure it's the back office.
I wish it was actually like Luca Doncic and Mark Cuban, but this is one of their marketing
teams.
I have to confess.
Yeah.
I mean, you got Nike on here, Warby Parker.
You've got Lyft.
Is Lyft on here because you used to work at Lyft?
Yes.
I mean, also because they're a paid customer, but that was one of the easier sales to make.
It's different at every company, which is kind of fun.
Like Amazon, I think it's six different teams each have their own trivia group.
And it's a DC and Queens, like a distribution center in Queens, the staff there.
Or it's like a, one of the Amazon logistics teams of tech workers, whereas something like
Impossible or Strava, it's the whole company and like one group, a couple hundred people,
you know, competing each week.
It sort of depends on the company size.
So how does it feel to know that everybody at Impossible Foods is using your trivia app?
It's pretty awesome.
I mean, it's not, I'm not changing anyone's life and I'm totally cool with that.
We're just making the week a little more fun.
Our initial slogan, which we removed was make Monday suck less because I think the Sunday
scaries are so real.
And we default to Monday, so it's just a Monday morning trivia quiz.
And so I like saying it's the one email you don't dread in your inbox.
And that was the whole goal all along.
It was like to have something you don't dread in your inbox.
And so I feel really good that thousands or tens of thousands of people a week have their
week just a tiny bit better.
Let's talk about some of the finances behind this because you're making 250 grand in revenue
every year.
But you're also like, you know, doing a lot of work.
You're coming up with trivia questions, you're grading these trivia questions.
What are the expenses like to run something like this?
Yeah, it's funny.
You know, we're bootstrapped and I studied finance and accounting.
So I feel like I have an okay grasp on that stuff.
So I'm comfortable just using Google Sheets as our financial software.
But the line item is literally COGS.
And the only thing I consider COGS, Cost-A-Gritzold, is trivia writing and quiz grading and everything
else that falls into other categories.
And I think it's probably like the only P and L on earth where the COGS is just writing
and grading trivia, like $1 to $2,000 a month for grading and $1 to $2,000 a month for writing
trivia questions.
For the vast, vast majority of the company, I've written the trivia questions.
So I've written something like 6,000 trivia questions.
And there's really an art to it.
There's a lot you learn really quickly and like what is and isn't a good trivia question.
And then also what is and isn't a good trivia question in terms of wanting the responses
to be auto-graded successfully by our algorithms, because everything that gets manually approved
or like moderated is expensive.
Yeah.
I mean, you've got a ton of people using it.
You said you've got, I think, 800 paid companies as clients, 4 million people have responded
to trivia questions.
It's a lot of grading to do.
It's like 100,000 people responding every week.
And this is like a free-form answer.
People aren't choosing...
They're not taking a box on a multiple choice thing.
They're like writing in their answer.
They can write any sentence they want to.
And then you somehow have built system.
I'm sure they put like funny jokes in there.
They put probably some obscene stuff in there.
You got to look through how do you auto-grade these free-form answers?
Before I jumped on the call with you, I had an email from a customer that I think is a
great example.
It was a question about some famous movie speech, and the answer is Independence Day,
the movie where the character gives a really rallying speech when the aliens are invading,
and it's now the world's Independence Day.
And the person had written on their answer sheet ID4, period.
And so our algorithm said, that's wrong.
And then our content moderator said, yeah, ID4 is not the answer.
The answer is Independence Day.
This person emailed me today showing me a picture of the original movie poster from
1996.
And they said, hey, this movie was actually marketed as ID4 in all of the marketing collateral
25 years ago.
And so I went back and I was like, all right, you get credit.
You clearly knew the answer to that question.
So I think that's a really good answer.
So basically, when we add that question to our system, we say Independence Day is an
acceptable answer.
We say the Independence Day is an acceptable answer.
And then when we're grading what people submit, we are basically stripping out vowels.
Sometimes you'll strip out consonants.
You'll do some fuzzy matching stuff, but we have a really high bar for wanting low air
points.
Tell me about the process of coming up with questions.
Because if you've written 6,000 trivia questions, I'm sure you've learned a ton about what makes
a good trivia question and what makes a bad one.
We do a thing where you can use a personalized category.
And so as an example, like a corporate finance team at Walmart literally writes Walmart.
And so their last question every single week is a question about Walmart.
Or Warby Parker in New York has NYC.
So their last question each week is about NYC.
And so these personalized categories make our life much harder.
It's kind of a classic, like do things that don't scale.
Like I have to write a question about Cadillac Fairview, which is a Canadian real estate
conglomerate.
And I've done that for 26 straight weeks.
It's getting out of control.
Are they paying you more to do that?
No.
Any group that signs up can have a personalized category.
We've taken a bunch of like, what I would call clever things.
So we don't make it as clear you can write anything in, there's a shuffle button that
shuffles what seem like random categories, but actually it's things we have a deep bench
questions for.
And there's other clever tricks like that.
But I love that you can get a question about anything.
Like a company that focuses on fermentation gets strange biology every week.
And so coming up with a question that actually makes it a lot easier.
The hardest part of a trivia question is you don't know anything.
I mean, I live on Wikipedia and we make sure to donate to Wikipedia every year.
That's one of our business expenses because we wouldn't exist without them.
What kind of person do you have to be to love writing trivia questions as much?
I mean, I think the prototypical Andy Hacker wants to basically automate everything.
You know, hire someone from the Philippines to basically write all these questions and
pay them like almost nothing, you know, just like, how do I automate all of this and basically
just collect the cash?
But you're writing thousands and thousands of trivia questions, you're scrolling through
Wikipedia, reading a bunch of random facts about like Walmart and strange biology.
Tell me about you.
I grew up loving trivia.
One of six kids and we would watch Jeopardy was in Chicago and Jeopardy is down at 330
there every day.
But it was right after school.
And so I'd come home from school, bring a couple of friends, get a couple of siblings,
like a parent or two would be around and we keep score, write down our answers, which
can get pretty aggressive.
And it ultimately unfortunately is just like who's the fastest reader because we don't
wait for it to finish.
I knew you had to be like a huge trivia nerd to do something like this because yeah, it's
a lot.
It sounds like a lot of work.
This is how they deal sort of born.
Like you did so much trivia.
You're watching so much Jeopardy.
You're hosting trivia nights.
You decided like there just needs to be a trivia app and internship at Bain and company
like big consulting firm.
And I wanted to like make my name known around the office, honestly, like as a 21 year old
in your first office job or 20 to 21 year old.
And I would send around a Google form each week to the whole office.
I got approved by like the social committee and it was Google form of 10 trivia questions.
And then I would hand grade the responses and put together like a crappy Photoshop of
like, you know, a partner's face on a Jeopardy podium if they won.
And then email that around.
And it was just a way to kind of get my name out there realistically.
But I thought it was so funny that the people who played most regularly were partners like
super senior people who I would assume are busier, but I was wrong.
They're the least busy people.
Their whole, their whole job is to outsource and delegate everything.
Yeah.
And I realized that, oh, this company likes it too.
And so eventually the kind of funny thing is I was thinking that I was doing Mailchimp
and Google forms just on my own kind of hacking away.
And I went to corporate drink with a friend on like a Wednesday night and it was the same
friend I hosted trivia with in college.
And this was like four years later and I was like, Hey, I have this idea.
And he said, I have a software engineer looking for a side project like of a roommate.
My roommates, a software engineer, like more side projects.
So I was kind of like, Oh, that's too Kismet.
Like I have to meet it.
So yeah.
Then we just hacked it together in late 2017.
I'm checking out your prices on your website.
And you're mentioning you don't raise prices on people who want the custom trivia questions.
And the pricing is you get four courses each month.
So basically one a week.
And it's $1 per user per month.
You know, teams of probably hundreds of people, we're paying hundreds of dollars.
You have teams of a tiny amounts of people who are paying just a few bucks.
Does your pricing start off this way?
If you like raise your prices since you started, or is it always been as cheap as $1 per user
per month?
We've never changed.
It's for sure a problem.
We know we should charge more.
It's so cheap.
Like we're very aware.
And honestly, it's even cheaper because we do a 50% nonprofit and school discount.
And we actually have a lot of schools and nonprofits and not like for students, but
a group of teachers at a high school.
So the principal pays and then like the teacher says something to talk about in the break
room.
That's really fun.
And then they'll pause for three months over the summer.
I was really afraid of the disincentives.
I think I'm just wrong and it's okay.
But the disincentives of adding someone new, if it increases your price, so like very typical
usage based pricing, right?
Like add Cortland to it, and then it's one more dollar per month.
And then we're varying.
Last month, we charged you $18 this month, 17.
Like that just scares me.
It's too much to think about.
And so we said tiers up to 10 people, 10 bucks a month, up to 25, 25 a month, up to 50, 50
a month.
That's smart.
I like the tier system, but yeah, $1 per user per month seems super cheap.
But I guess it depends on who you're talking to.
And if you're selling to Lyft, they're like, yeah, they could probably pay like 10 bucks
a user, not even blank.
If you're selling to like, I don't know, a group of construction workers who play after
the job, like they probably don't want to pay more than a dollar.
Yeah, it's opened up really different markets, which is good and bad.
I mean, not just any hacker, but any business.
We make a lot of mistakes in terms of people say like, you need to know your ideal customer.
And to me, I'm kind of like, I don't know.
As you saw, it's the Dallas Mavericks or it's a group of high school teachers or it's the
team at Lyft.
But like, it's pretty wide range and the price point is what enables that.
So walk me through like the very beginning of starting an app like this, because I mean,
in your head, you're like, I want to do trivia for people that'll be cool.
But as I understand it, you're not a software engineer.
You're not necessarily, so I have enough to build like this whole app from scratch.
You're just a trivia fan, right?
You're also probably not like a sales expert.
You're not sure how to like land a deal with the Dallas Mavericks, etc.
So what's like step number one for building water cooler trivia?
I mean, step number one for sure is when I sent around that Google form in my internship
that taught me the most important parts.
It was what's the right cadence weekly, not monthly, because weekly you have something
to look forward to.
It taught me that you can make free response work.
I think everyone's too afraid of it.
And that's why everything is multiple choice typically.
Like I get it.
It's really seductive that you can create things in real time and multiple choice, but it's
also less fun.
You don't feel as much joy because you're not pulling it out of the top of your tongue.
You're just pulling it out of choosing C every time.
And so that's how I started.
And then when I wanted to get more serious, I used MailChimp in Google forms.
And so then I had like a variable for the company name and that was with four teams.
My girlfriend at the time was at Macy's, like on a buyer department.
I had a friend who was at a consultancy and friend who has an ad agency.
And then I was at CityBike.
So we were four different ish companies and there were variables in MailChimp where we'd
change the company name, but send the same questions to all them.
And then on every Monday night, I would hand grade the responses in Google sheets with
like a yes, no, or like a checkbox column.
That was enough, honestly, but when we wanted to make it real, then it was just sitting
down and doing sort of the, what I think is appropriately celebrated as like the most
fun part of the app is like whiteboarding what you want it to all look like.
And so we basically said, look, we want to do that.
We want to be able to add questions to a database.
We want to be able to have a leaderboard that shows Cortland has won three of the last eight
times.
We want to be able to see the roster.
We want a billing page.
So I didn't realize it at the time, but it was product specs, I guess, but I would make
all my design mockups and all product specs in Google slides.
So that's what I knew.
I would move shapes around and like crop like crazy.
Yeah.
And like inspect elements on a page because I didn't know how to install a font and then
change the words on that page, take a screenshot of that page, paste that into Google slides.
So it was really turning what I was doing with no code, I guess, MailChimp and Google
forms into product specs and my design tool of choice is Google slides.
And then fortunately the engineer and my partner I was working with was good enough to turn
that into real things.
Wow.
That's insane.
Because I mean, you've done a lot of actual practical work to do all the research to figure
out how do you do trivia?
Well, how do you do open ended questions, et cetera.
And the other thing that's interesting about that is that for your two co-founders, I mean,
it's like a side project for them still.
They're both working full time jobs and you are 100% of your time on water cooler trivia
because you eventually quit your job at Lyft.
Yeah.
So basically it was really slow, like really slow.
We built the thing and we were too afraid to turn pricing on so it's free.
And then four months later we said, screw it, like let's turn pricing on.
And then someone paid and that was a miracle.
And we actually even hosted a trivia party where we pasted like seven, 70 questions on
like folded pieces of paper in my apartment in Brooklyn and like people would walk around
and like keep score and like, just cause we made a $200 sale.
I definitely spent more in like construction paper in time for that celebration.
So in 2018 it went from $0 to about 10 K ARR and we would meet Tuesday nights.
We all had real jobs and then 2019 went from 10 K to 20 K ARR.
So we all got a little more serious at our real jobs, I guess.
So now we were meeting every other Tuesday, basically meeting in person in New York, a
lot of 1 AM city bike rides across the Manhattan bridge.
I just felt like no one was churning out, like it was a really sticky product.
We had no money and we didn't know how to grow and so people were just kind of finding
out word of mouth, but no one was churning.
So I was like, there's something here.
So I made the decision to leave Lyft where I was as a product manager, I go full time
on March 7th of 2020, which I mean, that's a week that everyone remembers for obvious
reasons.
And my plan was to go full time into watercolor trivia.
They both stayed at their jobs.
I wrote up a one page contract that the three of us signed and so they agreed to grant me
more equity and like won't get into the specific terms, but they get it.
Like you'd rather own a smaller share of something worth a lot more than a bigger share of something
worth essentially nothing.
And so they were cool with that.
And they said they kept working full time.
We've still met once a week on Zoom throughout the past year, but the one year contract just
ended of like, we're giving Colin this much of our equity for committing one year.
And so now I'm in like, what happens now phase?
What was going through your mind at the time?
I mean, like for you to quit your job, you're looking at the numbers, like no one's churning,
but how big do you think this could possibly get?
You know, like it wasn't at the point where it was like probably anywhere near your full
time salary at Lyft.
No.
So I had a really specific time-boxed goal.
So my goal was to 10 exit and go from 20K error to 200K error in 12 months.
So you know, it's nice cause you know, you need to pick up each month in gross dollars
or in percentage growth, whatever you did math.
We even wrote down, I wish we wrote down the odds we thought of hitting it, but we wrote
down here's the three paths that could happen.
And then here's our default for what we do if we hit these targets.
So one was like, get to 200K, scratching and clawing, used everything in our arsenal.
It was so hard.
And that would be default sell the business.
It was after six to nine months, like it's just not happening.
We've tried everything we can think of and like, we're not even at 80 or 100K yet.
And that would be default sell the business, call and find a job.
And then the third option, which lo and behold somehow happened, was hit 200K and still growing
it.
We even wrote numbers crazily.
We said hit 200K within 12 months and still growing it greater than 4% month over month
ARR.
At that point need to really think about doubling down and like, don't just look to sell like
this thing is working.
It's pretty cool that you mapped it out though.
And you like pretty clearly cleared your goal cause you're at 250K, which you're getting
like 25% over your goal.
What do you, what was your plan at the beginning to hit that goal?
Cause it's easy.
Like I've been in this situation plenty of times at startups where I'm like, I'm going
to get to this number and writing down a number on a page is very, very different than having
a plan for like how you're going to get to that number, you know, are you going to build
more features?
Are you going to ramp up sales or like raise prices?
Like what was your thought?
If there was any sales to ramp up, I would have been all over that, but I don't even
know what that would mean.
I'm definitely a huge believer that distribution matters, not more than product, whatever.
That's like a false dumb binary, but I knew we were not going to have a ton of new features.
Like Ryan was the only engineer.
He has a real job.
It's serious engineering job.
He's awesome and he knows our whole code base cause he's written it all so he can add new
features, but not regularly.
And so it's basically the worst possible ratio.
If you think of me as just a product manager, it's like a one to 0.1 product manager to
engineering ratio.
It's like all right.
I have like stacks of things I want to build that have not gotten built, you know, fully
designed to Google slides, except I've graduated Figma now.
Honestly, it was just blind faith on the concept of elbow grease.
I was like, I'm pretty sure only two things matter, elbow grease and throwing darts.
Like you have to be able to just keep throwing darts.
You're going to miss most.
That's cool.
Just got to keep grinding.
So for me, that meant putting a demo button on the website.
You know, we were afraid of it at first, but then I probably did three entry demos in the
past year and that helps.
It is kind of scary to put stuff like that on your website.
Again, for the same reason that I was talking about earlier, like that prototypical Andy
Hacker doesn't want to have to do a bunch of manual work to sell their app.
You know, ideally people would sign up and just click buy and that will be it.
It truly was elbow grease and throwing darts.
And that's what we guessed.
And we were right.
Like some ROI was really good, but some could be a red herring.
Like we sponsored.
I listened to a podcast on the rise and fall of HQ trivia and I listened to the first episode
like last May.
And I was like, this is amazing.
It's just really well reported long form narrative journalism.
I love it.
And also it's fascinating story.
And there were no ads in the podcast and I was like, this is insane.
And so I DM'd the host on Twitter and I was like, Hey, can I sponsor the whole series?
And it's from the ringer who just bought bought by Spotify.
So I'm like, this is part of some serious ad operation, right?
Or whatever.
And it turns out it was not.
She was like, we're in the process of like moving our ads to Spotify, but it hasn't happened
yet.
So like, we don't really know what's going on.
I mean, it was a little more professional than that, but like, anyway, I sponsored the
last five episodes of like the six part series for 2,500 bucks.
It's super paid off.
They were host red, really good ads.
We got like this amazing ROI on it, like a five X ROI or something.
And it's like still in the podcast.
So we still have things coming 10 months later and then it was in the like best podcast list
end of the year, blah, blah, blah.
And so we were like, this is amazing.
Let's double down.
And so we also sponsored this like rise and fall of WeWork podcast that Bloomberg put
out.
We're like, this is it.
And we spent like five or six times as much money and complete dud, like literally zero
sales.
No one cares.
Oh my God.
Oh, what a red heron.
We were like podcasts for the future.
And it turns out just like the alignment with people listening to HQ and remembering doing
trivia with their coworkers in the office was so perfect for our product.
Did you like do like a step three?
Like let's go find other podcasts to talk about trivia.
We have over the years sponsored like super niche ones.
There's a thing called Trivial Warfare.
That is I won't speak to their numbers because I don't know them, but it's a very small investment
on our part and we love sponsoring them because they're awesome.
They just are a couple of friends who do a trivia game each week on a podcast.
There's this other one that I've gotten obsessed with.
And if anyone road trips, it's called Pod Quiz.
He's done over 800 episodes over 15 years, this guy I've written and it's like really
high quality.
And it's my fiance and I have driven a lot this year and we've done hundreds of episodes
and you can like keep score for yourself.
Our best is like 18 out of 20.
It's super fun.
I emailed him.
You have no sponsors.
I love what you do.
It's amazing.
And I mean, bless him.
He's like, I don't do ads.
I'm pure.
I mean, he didn't say I'm here, but it's kind of like what I turned into it.
Right?
Yeah, I love Pod Quiz, but they didn't want our money, which is fine.
Was there any like one dart you threw in particular that just like has been responsible for you
being able to grow your revenue 10X or have there been just like a few, you know, like
that podcast ad really worked out and like maybe a few other things?
Like it's like the plurality game, not a majority game, for sure.
SEO helps.
We invest in content marketing, but stereotypes are grounded in truth and the stereotype that
SEO takes a long time is real and you've got to put a lot of content out there for a long
time.
So it feels really good like all of the endorphins fire in my brain when an article goes to the
front page of Hacker News.
But then, you know, you typically get zero to one free trial signups out of it.
That's a good example of what I think feels like good marketing versus isn't actually.
We sponsored a thing called HR Summer School, which was like a series of lectures.
We did like a lunch break trivia game every day and there were like hundreds of HR professionals
there that helped.
Slack featured us in a couple posts.
PR is super helpful, like just to put the numbers in perspective for folks.
We were in a fast company article recently, just listed as like one of five things to
do virtually.
I don't know.
It was not literature.
It was a listicle.
It drove the equivalent of like just this mid-article placement of us, like 3K and ARR,
just based on like all our conversion and funnel stuff.
So I mean, you did the math backwards there and it's like, oh, it's probably worth investing
in PR more.
But we paid for PR for a minute.
They got two not very good placements for us.
And then all of our really good placements was just me cold emailing journalists, just
straight up elbow grease and just badgering them.
It's cool having a low-turn business where it doesn't really matter where you get your
customers from.
You tend to keep doing trivia because it means that you can kind of rest easy not having
found this one channel to end all channels that works forever until the end of time.
You'll be like, oh, this is the end.
It's kind of stopped working.
But that's fine because all the customers I got are still going to stick around.
And you just got to keep doing the elbow grease thing, as you'd call it.
Keep hitting different targets, keep hitting different channels.
And you know that you're kind of slowly filling up this bucket full of water, I guess literally
full of money, to get to some goal.
What is that goal for you?
Why do this?
How big can water cooler trivia get?
I actually think this can be so much bigger.
So the product right now can tend to 20X, no doubt, no question, no improvements.
Doesn't mean it will happen.
It certainly doesn't mean it would happen quickly.
But it can do that.
We only have eight entry groups, and the diversity of companies that use it is pretty remarkable.
But now I'm realizing we are super lucky with the tailwinds from work from home shift.
But it's opening up a bunch of doors, as everyone knows.
What is the future of hybrid work and this and that?
And one thing we did is it's asynchronous team building.
And when I look around, pretty much everything is synchronous.
And it's everyone get together.
I don't think people like having things on their calendars.
I think it's anxiety inducing for a lot of folks.
And if one of the benefits is remote and hybrid work is more control over managing the balance
between professional and personal lives, I think asynchronous everything is better.
I think team building doesn't have to be an exception.
And so we've really worked hard to build asynchronous team building as a core concept, where we'll
feature little anecdotes of how Cortland knew that really hard question in the results.
So you're still kind of getting to know Cortland and sparking conversation, even though he
answered the trivia with his morning coffee at 9am, and I did it over lunch with my fiance.
So I'm thinking a lot bigger now about asynchronous team building in general.
And I also think that a lot of trivia, trivia is a much bigger industry than people realize.
You don't really think of trivia as an industry, it just sounds silly.
It's not like databases.
But there's a ton.
There's so many virtual trivia event platforms, and I don't think a lot of them are very
good.
You kind of need Zoom and then a good Discord or Slack and then like Google Forms and like
this and that.
I think you can do a lot better.
And so working on a live event platform, basically, as like an add on to our subscription business.
And then I think there's a lot you can do within that.
I think there's more games you can do.
Not everyone loves trivia.
There's a lot of other word play games I'm a huge fan of, that we sneak in as fake trivia
questions sometimes.
Yeah, I'm thinking a lot bigger now, which is exciting and admittedly hard for me, like
I'm someone who I think thrives in working within constraints.
Yeah, constraints are good.
And it's smart to have constraints because they get you...
They're the things that have gotten you to where you are now.
And the danger is that once you get two starry eyes, you lose the constraints, you sort of
lose a little bit of your magic.
And I mean, I've dealt the same thing with indie hackers, right?
My goal was very similar to yours in the beginning.
Get to $10,000 a month in revenue.
I got somewhere close and then ended up joining Stripe and then it was like, all right, boom.
Your goals are completely different.
They're a thousand times bigger.
Yeah, and for you, you were at the beginning, I love trivia, I want to do this cool side
project with some friends, now you're thinking about, let's think about the entire trivia
asynchronous team building industry.
It's made me more opinionated, which is fun, right?
It's fun to be opinionated and feel like you can be opinionated.
I'm more willing to say I think multiple choice trivia sucks now than I was 12 months ago.
I'm more willing to, yeah, I guess have stronger opinions.
Are there any guiding philosophies or mental models or books that guide how you run your
company and how you live your life?
I have no idea where I read this.
I'm sure it's just basic science.
But that there's two kinds of stress, eustress and distress, like E-U-S-D-R-E-S-S and distress.
And that the more you can have more of the stress in your life be eustress and distress
and choose not obviously most important things in life you can't choose.
But the more you can think about stress as a positive and not negative thing, man, that
has been so liberating just in general for every step of my life from a presentation
in a company that I'm working at to personal relationships to anything.
But the biggest has probably been the book Moonwalking with Einstein, which is about
memory palaces and remembering things.
One of my favorites, super cool book.
Yeah, it's amazing.
Joshua Fuller, I mean, him and his two brothers are all phenomenal writers.
Joshua Fuller also founded Atlas Obscura, which is this super cool website.
The book's about memory palaces, but I don't really care about it in terms of that.
Like, remembering trivia facts, but it is this one line that's monotony compresses time,
novelty unfolds it.
And so I'm a huge believer in introducing novelty in any way, shape, or form to just
multiply the number of things you remember, because essentially our memory of our life
is just how many signposts you have to look back on.
And so if you do more weird, interesting, different novel things, you feel like you're
living a longer life, which ultimately is the most important thing.
People talk about biological time.
I want to live till I'm 90.
It's like, I would rather have a super densely memorable life to 70.
It just matters more.
There's a...
I did an episode maybe a year and a half ago now with the creator of an app called One
Second Every Day.
And the whole idea behind his app is basically you record a one second video every day and
then eventually you stitch it together and you got like, I don't know, like a six minute
video of your entire year.
And the cool side effect of it is not just having this video, it's that the video itself
motivates you to do more interesting things, because you don't want to have like the same
one, like, you know, in May during the pandemic, my one second video every day was me and my
computer.
I'm like, oh, this has got to change.
You know, and like a month later, I was on the road doing a road trip, looking at a bunch
of different stuff in part because I wanted my one second video to be different.
I wanted to actually like live a different life.
So I'm right there with you, like novelty, what did you say, unfolds time and gives you
just more memories.
And that makes it seem like your life is much longer.
Yeah.
So I have a thing, this is the sixth year right by a physical calendar, right, like
a wall counter.
I'll write one thing each day, and the only rule was it couldn't be about work.
And it's like in Sharpie, and it's like two words.
And like, literally, I have to write one thing each day.
But it's a tiny square, and I have a Sharpie, so like truly, we're talking like micro tweet
like things here.
And I can look back in the last six years and look at one thing every single day.
And like, I'm super flawed and imperfect.
So sometimes I don't do it for a week, especially when I've been on kind of the move this past
year.
And then I use basically the photos in my phone, my calendar, a runner fitness tracking
app to just like recreate, like there must have been one thing that day, like that.
And some days looking back, I'm like, Oh, how's a, how's an arid day?
Not much going on.
But it's so nice to look back and find things and it's like a, I think it was like a poor
man's, like a poor man's time hop.
But like, I'll look back to past year's calendar sometime be like, Oh, April 13th, 2018.
And it'll be like, lunch and walk with JU or something, so I just do initials for people.
And I'll text JU and be like, yeah, it's poor man's time out.
I know Facebook used to do that thing all the time where you would sign on and it would
say, you know, five years ago today, you and this friend were tagged in this photo, you
know, tag both of you.
And I'm never on Facebook anymore, but that was kind of cool.
It was like a good way to connect you to your friend.
Apple's been doing more and more of it where they put with like the widgets and stuff on
the new iOS home screens where they'll like surface photos to you that like, I don't know,
it's generous, probably call it machine learning, but I'm sure it is somewhere deep in the trenches
but I feel like they're trying to do that.
Yeah.
My Google photos is constantly, Oh, six years ago today, you were doing this, like this
fun thing.
Don't you wish you were back there?
And I'm like in my apartment during the pandemic, like, yes, as a matter of fact, I do.
Thank you for feeding me into your sentiment analysis algorithms.
I feel very taken care of.
I just Googled a U-Stress because I never heard of this term that you brought up earlier
like these two different types of stress.
It's totally real.
Because U-Stress is a kind of doable stress, as articles apparently written by a doctor
core.
So if they're a doctor, it must be true.
You're faced with a challenge, but a challenge that you know you can handle, and you actually
look forward to handling that challenge.
So you feel out of your comfort zone in a good way.
Yeah, let's do it live.
Yeah, we'll do it live.
And that, to me, like encapsulates kind of the startup journey, you know, you in March
of 2020 quitting your job and saying, I'm going to 10x my revenue and I'm not sure how
I'm going to do it.
Like, I'm looking forward to trying it, you know, like that's the good kind of stress
that you want as a founder.
I was talking to my brother about this actually yesterday.
He was talking about how so many people structure their lives to avoid having problems.
But what you really want to do is just have good problems in your life.
You want to have problems that you really wake up excited to solve because problems
are kind of the thing that pull you forward in life.
They get you like motivated to do something.
You know, if you have no problems, then what do you do?
You just kind of sit around and get fatter.
But if you have bad problems, then you just, you know, I guess that's distress and you
feel terrible, but you have good problems, then you wake up every day super motivated,
super excited, you know, you have something that you're running toward.
And I've tried to structure my life like that for the last 10 years.
You know, what can I, what problem can I have that I actually want to work on?
We were talking a few weeks back and you also mentioned another idea that I thought was
really cool, which is the peak end rule, which is like, you know, kind of a common idea from
psychology.
I'll let you explain it because you actually kind of woven it into the way that you live
your life, which is a lot more than I've done.
I just sort of read it, read it and then forgot about it.
But you've been like living the peak end rule.
Yeah.
So basically read it and forget it is my mantra for everything.
But then when you read it the sixth time, you, uh, it's hard to forget.
So basically, as I noted before, like I'm really interested in how we remember things
and not in a, like, I want to study neurons my whole life way, but just in a, like, how
does it impact my life and how can it make me happier and those that I love happier.
The way I think about memory is based on the psychological concept of peak end rule, which
is what do we remember from an experience?
So like think of one experience, like a sports game, you went to a life event or a job or
a grade in school, like a whole eighth grade or whatever.
You're probably going to remember two things on average, you're going to remember the peak.
So either the, like, I think it was like the spikiest experience, like the most bad or
the most good.
Yeah.
The most extreme part that happened.
Yeah.
It could be anything.
And then you think of the end, like people just think about their endings a lot and how
you typically remember that experience.
So like there's been psychological studies of how bad or good you remember that experience
essentially as the average of the peak and the end.
And so it's really hard.
It's impossible in a good way to control the peak of anything, right?
It's like going to a Cubs game at Wrigley field and like, I choose for there to be a grand
slam right now.
And the whole crowd to erupt.
It's like, no, you can't choose that.
It's going to happen or it's not, but I think you can control the ending.
And I think people can control the ending more and it ends up like weirdly, perversely,
improving your memory of so many things in life.
Like if you control the ending, you know, people talk about like going out on top, ending
too early instead of ending too late.
I'm a massive fan.
And like, I've seen it.
I listened to you a couple of weeks ago.
It really clicked for me in a business sense when I saw it with, I was at Bain and company,
like consulting company and people leaving, they just treat you so well.
It's like the greatest exit experience.
They like, there's for sure some self-interest there.
They want you to, when you're an executive somewhere else to hire them as a client or
to like, have you boomerang back as an employee.
So like, you know, it's not like purely altruistic, but they treat you really well on the way
out the door.
You know, people send really nice, thoughtful, goodbye emails.
You know, I know this stuff happens at a lot of companies, but even like the exit and
view process and helping you find a new job and this and that, it's really excellent.
And I think it's what allows you to be regarded as like a really good employer, just because
you control the end experience.
You're not going to control their peak experience because maybe they had a lot of 3am nights
in a row making slides, but you can control the end experience.
And if that color is disproportionately 24 months of labor, then wow, that's super good
ROI.
Yeah.
I have a friend who does this.
He came to visit me from Russia and he had a few people to visit in the States, but he
came from Russia.
So I was like, are you going to be here for like a week?
You know, a few days.
He's like, no, I'm going to be here for two nights and like two nights.
And he's like, look, always understay your welcome.
Never overstay your welcome because then the end is going to be like, it was too, it's
too soon.
You just got here.
Everyone's going to want you to stay.
And then the memory of that trip is going to be great, but you stayed for three or four
nights and people are going to be kind of like, oh yeah, it's, I'm completely ready
for you to go now.
And then that's like the ending of the trip and it sucks.
Yeah.
I think about it a lot for trips, especially.
And so one thing I do that I stole from someone is the alpha, the game at the end of every
trip I take.
So like my fiance and I just lived in New Orleans for months and we just did the alpha
game about New Orleans.
So you come up with some memory for all 26 letters to represent that trip and you do
like a long list.
So for a, you know, we like for B listed, but yay and this and then like 20 things.
And then we go back through it and choose one thing.
And now you have 26 things to remember that trip.
You do it in the airport or the car on the way out of town and then you take a picture
of it and you'd be like, make it a poster and not do whatever.
But like you have so explicitly controlled the ending of that trip by like summing it
up into the 26 best food items and inside jokes and places you went and like people
you met.
It's amazing.
And like that will color the entire memory of your trip, which is like a little internally
manipulative, but alas, are you doing this somehow with, uh, with water cooler trivia?
They're like ways that you're affecting the endings of you running this business to make
sure that it's a good memory.
One thing is I really want to do what we call it's such a lame name and I love it.
Quarterly learnings.
It's this feature idea that I've had forever.
So it's like quarterly earnings, but now and it's like the year in review from like Spotify
or like lift or whatever, but it basically just sums up the last three months of trivia.
Sweet email, like indie hackers team, like here's your quarterly learning.
It's like Cortland was the rookie of the quarter.
Like he was nude if it's even like did the best of trivia.
Like most improved was Colin and like the worst of geography was so-and-so and like
the best anecdote was so-and-so.
So I really loved the idea of like capping a quarter, um, just giving timeframe something
is really helpful and like perpetuity weekly trivia is really nice, but with like the leaderboard
that like resets every month and like being able to do short-term and long-term duration
simultaneously is like really important.
I think so.
I think about endings in that way.
Cool.
Well, I'm a huge fan.
I should sign up for indie hackers.
I've never done, I've never been really that good at trivia myself, but if, if we add a
custom category and get you making indie hackers related trivia questions, I'm pretty sure
I can do, uh, pretty well.
The end of these podcasts, I always ask the same question, Colin, which is what have you
learned from your journey that you think fledgling indie hackers who just getting started can
take away?
Yeah.
I mean, I think it is as not as simple, but I think it's as real as just say yes to life.
The reason trivia started is because what a trivia started because honestly, I went
out on a Wednesday night to watch a US soccer game and I invited this friend and then we
were just talking about these emails I had been sending and he was like, I have an engineer
roommate and I can't like reverse engineer a lot of what has gone well and really fortunate
for us.
But in terms of just saying yes to things like send a cold email, do the thing that
is an outside chance paying off.
I started it by at a bar one night writing down 10 questions.
I turned my phone off and I wrote 10 trivia questions that I didn't know the answer to.
That's the best way to write trivia.
10 things you want to know the answer to.
And it was just because like I was biking home and it looks like the bar looked fun.
And so I sat alone and wrote 10 questions on a napkin.
And I think the more you just say yes, the more I consider those darts thrown, like good
things can happen.
I'm not sure how much I believe in like luck is the residue of preparation or whatever,
but I'm certainly a believer in like good things is the residue of trying a lot of things
that could end up good.
Yeah.
Your framework, elbow grease and darts.
I love it.
Yeah.
Elbow grease and darts.
That's life.
That's life.
All right, Colin.
Well, thanks for coming on the show.
You can go to find out more about water cooler trivia and your very ambitious future plans.
So it's watercoolertrivia.com.
It is exactly what it sounds like.
We also recently purchased trivia.co.
So like T-R-I-V-I-A.C-O.
This is admittedly kind of massive buyers or more on this one.
The negotiation went faster than expected, but it's kind of cool that we're trying to
figure out what to do with it.
So next up, we are moving and shaking.
We are growing to a lot more teams and going to build probably additional games and introduce
our live trivia format sooner rather than later.
We are pondering how to grow the business capital wise too.
It's kind of like the problem that I think all indie hackers would love to face.
Do I raise some money?
Do I raise some debt?
Do I double down again?
But I took no salary the last year and you can only do that so many years and soon.
All right.
Well, I'll be following along and maybe you can come back on the show if you end up emailing
me and tell me you're at a million dollars in ARR.
Hey, Kortland, get me back on the show.
Well, thanks again, Colin, for coming on.
Of course, Kortland.
Yeah, thanks.