The Simplest $250K ARR Startup You've Ever Heard Of with Collin Waldoch of Water Cooler Trivia

Courtland Allen: 0s

What's up, everybody? This is Courtland from indiehackers.com and you're listening to the Indie Hackers Podcast. More people than ever are building cool stuff online and making a lot of money in the process. On this show, I sit down with these indie hackers to discuss the ideas, the opportunities, and the strategies they're taking advantage of so the rest of us can do the same.

We gotta talk about Water Cooler Trivia. You've been emailing me for like a year and a half. I almost never invite anybody on the show who comes over email. Every now and then, but here you are. It's because of the way your emails progressed.

It was like 2019, hey Courtland, just did an interview on Indie Hackers making like, you know, $10,000 a year, I think it'd be good for the podcast. I was like, we'll wait a little bit. Then like every few months after that, I was like up to $50,000 a year up to a hundred thousand dollars a year. What was the last email you sent me? I think you were like 200.

Collin Waldoch: 57s

Probably 200, 250. I don't know when I sent you the email, but yeah.

Courtland Allen: 59s

$250,000 a year. Jesus, Collin’s crushing it. I don't know what happened during the pandemic, but your app is blowing up. What is Water Cooler Trivia?

Collin Waldoch: 1m 7s

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.

We send a weekly trivia quiz to work teams. It's typically over email or it's over Slack or Microsoft Teams. You answer 10 questions or more or less, depends on how you customize it. Then the next day the results come out.

It's sort of asynchronous; fill it out during the day Monday, results come Tuesday. There's a leaderboard over time and it's just something that's fun and easy I think that's not a chore.

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. It was just a random idea that was what we really called beer money idea. Bootstrapped it for two years with friends two and a half years before any of us took a full-time leap.

Courtland Allen: 1m 59s

it is super cool. I'm on your website right now. The description really is as simple as you make. 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.

You got some pretty cool customers on here. You've got Strava, Amazon as a customer, Impossible Foods, the Dallas Mavericks. I'm just imagining it was matching the basketball players playing trivia, but I'm sure it's the back office.

Collin Waldoch: 2m 25s

I wish it was actually Luka Dončić and Mark Cuban, but this is one of their marketing teams, I have to confess.

Courtland Allen: 2m 33s

I mean, you got Nike on here, Warby Parker. You've got Lyft. Is Lyft on here because you used to work at Lyft?

Collin Waldoch: 2m 39s

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. Amazon, I think it's six different teams each have their own trivia group and it’s a DC in Queens, like a distribution center in Queens, the staff there. Or it's of the Amazon logistics teams of tech workers. Whereas something like Impossible or Strava, it's the whole company and one group, a couple of hundred people competing each week. It's sort of depends on the company size.

Courtland Allen: 3m 6s

How does it feel to know that everybody at Impossible Foods is using your trivia app?

Collin Waldoch: 3m 11s

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. Cause I think the Sunday scaries are so real and we default on Monday. So, it's just a Monday morning trivia quiz.

I like saying it's, it's the one email you don't dread in your inbox. That was the whole goal all along. It was to have something you don't dread in your impacts. I feel really good that thousands or tens of thousands of people a week have their week, just a tiny bit better.

Courtland Allen: 3m 42s

Let’s talk about some of the finances behind this cause 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 to run something like this?

Collin Waldoch: 3m 55s

Yeah, it's funny, you know, we're bootstrapped. I studied finance and accounting, so I feel like I have an okay grasp on that stuff. 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 of goods sold - is trivia writing and quiz grading and everything else falls into other categories. I think it's probably like the only P & L on earth where the COGS is just writing and grading trivia.

$1,00 to $2,000 a month for grading and $1,000 to $2,000 a month for writing trivia questions. For the vast, vast majority of the company, I've written the trivia questions. I've written something like 6,000 trivia questions. There's really an art to it.

There's a lot, you learn really quickly 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 moderated is expensive.

Courtland Allen: 4m 45s

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 the trivia questions. That's a lot of grading to do. It's a hundred thousand people responding every week. This is free form answers, and people aren't choosing, they're not ticking a box on a multiple-choice thing. like writing in their answer. They could write any sentence they want to, and then you somehow have built systems.

I'm sure they put funny jokes in there. They put probably some obscene stuff in there you got to look through, how do you auto grade these freeform answers?

Collin Waldoch: 5m 12s

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 in fading and it's now the world's Independence Day.

The person had written on their answer sheet ID4. Our algorithm said that's wrong. 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.

They said, hey, this movie was actually marketed as ID4 in all of the marketing collateral 25 years ago. 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.

Basically, that question to our system, we say Independence Day is an acceptable answer. We say the Independence Day is an acceptable answer. Then when we're grading what people submit, we are basically stripping out vowels. Sometimes they'll strip out continents. You'll do some fuzzy matching stuff, but we have a really high bar for wanting low error rates.

Courtland Allen: 6m 13s

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.

Collin Waldoch: 6m 21s

We do a thing where there’s a personalized category. As an example, a corporate finance team at Walmart literally writes Walmart. Their last question every single week is a question about Walmart or Warby Parker in New York has NYC. So, the last question each week is about NYC.

These personalized categories make our life much harder. It's kind of a classic do things that don't scale. I have to write a question about Cadillac Fairview, which is a Canadian real estate conglomerate. I've done that for 26 straight weeks. It's getting out of control.

Courtland Allen: 6m 50s

Are they paying you more to do that?

Collin Waldoch: 6m 52s

No. Any group that signs up can have a personalized category.

We've taken a bunch of what I would call clever things. 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 bunch of questions for, and there's other clever tricks like that.

I love that you get a question about anything. A company that focuses on fermentation gets strange biology every week. 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.

Courtland Allen: 7m 25s

What kind of person do you have to be to love writing trivia questions as much? I mean, I think the prototypical indie 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.

Just like, how do I automate all of this and basically just collect the cash, but you're writing thousands of thousands of trivia questions, scrolling through Wikipedia, reading a bunch of random facts about like Walmart and strange biology. Tell me about you.

Collin Waldoch: 7m 51s

I grew up loving trivia. One of six kids, and we'd watched “Jeopardy!” We lived in Chicago and “Jeopardy's” on at 3:30 there every day, but it was right after school. I’d come home from school and bring couple of friends, get a couple of siblings, a parent or two would be around and we keep score, write down our answers just can get pretty aggressive. It ultimately, unfortunately it's just like, who's the fastest reader because we don't wait for Trebec to finish.

Courtland Allen: 8m 12s

I knew you had to be a huge trivia nerd to do something like this because it's sounds like a lot of work. Like you did so much trivia, you're watching so much “Jeopardy!”, you're hosting trivia nights, you decided there just needs to be a trivia app.

Collin Waldoch: 8m 23s

I had an internship and Bain & Co, the big consulting firm. I wanted to make my name known around the office, honestly, like as a 21-year-old in your first office job.

I would send around a Google Form each week to the whole office. It got approved by the social committee and it was a Google Form of 10 trivia questions. Then I would hand grade the responses and put together a crappy Photoshop of a partner's face on a Jeopardy podium if they won and then email that around.

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.

Courtland Allen: 9m 1s

They're the least busy people. Their whole, their whole job is to outsource and delegate everything.

Collin Waldoch: 9m 6s

Yeah. I realized that, oh, this company likes it, too. Eventually the kind of funny thing is, I was thinking then I was doing MailChimp and Google Forms just on my own kind of hacking away. I went to grab a drink with a friend on a Wednesday night and it was the same friend I hosted trivia with in college.

This was four years later. I was like, hey, I have this idea. He said, I have a software engineer looking for a side project. I have a roommate. My roommate is a software engineer looking for a side project. So, I was kinda like, that's too kismet. I have to meet him. Then we just hacked it together in late 2017.

Courtland Allen: 9m 40s

I'm checking out your prices on your website. You mentioned you don't raise prices on people who want the custom trivia questions. The pricing is you get four quizzes each month. Basically, one a week. It's $1 per user per month. You know, teams of probably hundreds of people who are paying you hundreds of dollars and you have teams of tiny amounts of people are paying you just a few bucks, three bucks.

Did your pricing start off this way? Have you raised your prices since you started, or has it always been as cheap as $1 per user?

Collin Waldoch: 10m 6s

We've never changed. It's for sure a problem. We know we should charge more. It's so cheap. 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. Not for students, but a group of teachers at a high school, so the principal pays and then the teacher’s talk about in the break room, that's a 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, very typical usage-based pricing, right? Add Courtland to it and then it's one more dollar per month. Then we're varying. Last month we charged you $18, This month $17.

That just scares me. It's too much to think about. So, we said tiers up to 10 people, 10 bucks a month, up to 25, $25 a month up to 50, $50 a month.

Courtland Allen: 10m 55s

That’s smart. I like the tier system, but yeah, $1 per user per month seems super cheap, I guess it depends on who you're talking to you. If you're selling to Lyft, they're like, yeah, they could probably pay 10 bucks a user, not even blink. If you're selling to like, I don't know a group of construction workers who play after the job, they probably don't want to pay more than a dollar.

Collin Waldoch: 11m 11s

Yeah. It's opened up really different markets, which is good and bad. I mean, not just indie hacker, but any business, we make a lot of mistakes in terms of people say you need to know your ideal customer.

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 a team at Lyft. It's pretty wide range and the price point is what enables that.

Courtland Allen: 11m 32s

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'd be cool. As I understand that you're not a software engineer, you're not necessarily savvy enough to build this whole app from scratch.

You're just a trivia fan, right. You're also probably not a sales expert. You're not sure how to land a deal with the Dallas Mavericks, et cetera. What's like step number one for building Water Cooler Trivia?

Collin Waldoch: 11m 56s

I mean, step number one for sure is when I sent around that Google Form at 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. I get it. It's really seductive that you can create things in real time in 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.

That's how I started. When I wanted to get more serious, I used MailChimp and Google Forms. Then I had a variable for the company name and that was with four teams. My girlfriend at the time was at Macy's in a buyer department. I had a friend who was at a consultancy, had a friend who has an agency. And then I was at City Bike. We were at four different-ish companies. There were variables in MailChimp where we changed the company name, but send the same questions to all them.

Then on every Monday night, I would hand grade the responses in Google Sheets with a yes, no, or 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 the most fun part of the map is whiteboarding what you want it to all look like.

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 Courtland has won three of the last eight times. We want to be able to see the roster. We want a billing page. I didn't realize it at the time, but it was product specs, I guess, but I would make all my design mock-ups and all product specs in Google Slides, because that's what I knew.

I would move shapes around and crop like crazy. Then 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. It was really turning what I was doing with no code, I guess, MailChimp and Google Forms into product specs. My design tool of choice is Google Slides. Then fortunately the engineer, my partner I was working with was good enough to turn that into real things.

Courtland Allen: 13m 53s

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. The other thing that's interesting about that is that for your two co-founders, I mean, it's 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.

Collin Waldoch: 14m 17s

Basically it was really slow, like really slow. We built the thing. We were too afraid to turn pricing on, so it's free. Then four months later we said, screw it, let's turn phrase again. Then someone paid and that was a miracle. We actually even hosted a trivia party. We pasted like 70 questions on folded pieces of paper in my apartment in Brooklyn and people would walk around and keep score and just because we made a $200 sale. I definitely spent more on construction paper and time for that celebration.

In 2018 I went from $0 to about $10K ARR. We would meet Tuesday nights. We all had real jobs. Then 2019, went from $10K to $20K ARR. 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 1:00 AM, City Bike rides across the Manhattan bridge.

I just felt like no one was churning out. It was a really sticky product. We had no money, and we didn't know how to grow. People were just kind of finding out word of mouth, but no one was Churning. So, I was like, there's something here.

I made the decision to leave Lyft where I was as a product manager and go full-time on March 7th of 2020, which I mean that's a week that everyone remembers for obvious reasons.

My plan was to go full-time on Water Cooler Trivia. They both stayed at their jobs. I wrote up a one-page contract, the three of us signed. They agreed to grant me more equity, won’t get into specific terms, but they get it. You'd rather own a smaller share of something worth a lot more than a bigger share of something worth, essentially nothing.

They were cool with that, and they said, they kept working full-time. We still met once a week on Zoom throughout the past year, but the one-year contract just ended up like we're giving Collin as much of our equity for committing one year. Now I'm in what happens now phase.

Courtland Allen: 15m 58s

What was going through your mind at the time? I mean, for you to quit your job, you're looking at the numbers, no one's churning, but how big do you think this could possibly get? It wasn't at the point where it was probably anywhere near your full-time salary at Lyft.

Collin Waldoch: 16m 12s

I had a really specific timebox goal. My goal was to 10X it and go from $20K ARR to $200K ARR in 12 months. So, 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 on 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.

One was get to $200K scratching and clawing, used everything in our arsenal. It was so hard. That would be default, sell business. It was after six to nine months, it's just not happening. We've tried everything we can think of and like we're, we're not even at $80 or a $100K yet. That would be default, sell the business and Collin find a job.

Then the third option, which lo and behold, somehow happened, was hit $200K and still growing it, we even wrote numbers, crazily. We said it hit 200 K within 12 months and still growing at greater than 4% month over month ARR. At that point we need to really think about doubling down and don't just look to sell, this thing is working.

Courtland Allen: 17m 15s

It's pretty cool that you've mapped that out though. You pretty clearly cleared your goal because you’re at $250K. You're getting at 25% over your goal. What do you, what was your plan at the beginning to hit that goal? Because it's easy, I've been in this situation plenty of times in startups, I'm like, I'm going to get to this number.

Writing down a number on a page is very, very different than having a plan for how you're going to get to that number. Are you going to build more features? Are you going to ramp up sales? Raise prices? What was your thought?

Collin Waldoch: 17m 40s

If there was any sales to ramp up, I would've been all over that. 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 a false stem binary, but I knew we were not going to have a ton of new features.

Ryan was the only engineer. He has a real job. It's a serious engineering job. He's awesome. He knows our whole code base because he's written it all so he can add new features, but not regularly.

It's basically the worst possible ratio. If you think of me as just a product manager. It's like a 1 to 0.1 product manager to engineering ratio, which is awful. I have stacks of things I want to build that have not gotten built. Fully designed Google slides, except I've graduated to 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. You have to be able to just keep throwing darts. You're going to miss most. That's cool. Just gotta keep grinding. For me, that meant putting a demo button on the website. We were afraid of it at first, but then I probably did three hundred demos in the past year and that helped.

Courtland Allen: 18m 40s

It is scary to put stuff like that on your website. Again, for the same reason that I was talking about earlier, the prototypical indie 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 would be it.

Collin Waldoch: 18m 50s

It truly was elbow grease and throwing darts. That's what we guessed and we were right. Some ROI was really good, but some can be a red herring. We sponsored, I listened to a podcast “On the rise and fall of HQ trivia”. I listened to the first episode last May. I was like, this is amazing. It's just really, well-reported long form narrative journalism. I love it. Also, it's fascinating story. There were no ads in the podcast and I was like, this is insane.

I DMed the host on Twitter and I was like, hey, can I sponsor the whole series? It was from the Ringer who just got bought by Spotify, so I'm like, this is part of some serious ad operation, right. It turns out it was not. She was like, we're in the process of moving our ads to Spotify, but it hasn't happened yet, so we don't really know what's going on. It was a little more professional than that. But anyway, I sponsored the last five episodes of the six-part series for $2,500 bucks.

It's super paid off. They were host-read, really good ads. We got this amazing ROI on it, like a 5X ROI or something. It's still in the podcast so we still have things come in 10 months later. Then it was in the best podcast list end of the year, blah, blah, blah.

We were like this amazing let's double down. We also sponsored this rise and fall of WeWork podcast that Bloomberg put out and we're like, this is it. We spent five or six times as much money. Complete dud, like literally zero sales. What a red herring, we were like, podcasts are the future. It turns out just the alignment with people, listening to HQ and remembering doing trivia with their coworkers in the office was so perfect for our product.

Courtland Allen: 20m 18s

Did you do a step three, let's go find other podcasts to talk about trivia.

Collin Waldoch: 20m 25s

We have over the years sponsored super niche ones. There's a thing called Trivial Warfare. 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 star 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. If anyone road trips, it's called Pod Quiz. He's done over 800 episodes over 15 years. It’s this guy in Britain, and it's really high quality.

My fiancée and I have traveled a lot this year and we've done hundreds of episodes and you can keep score for yourself. Our best is like 18 out of 20. It's super fun. I emailed him. I'm like, you have no sponsors. I love what you do. It's amazing and I'm in. Bless him. He's like, I don't do ads. I'm pure. I mean, he didn't say I'm pure, but it's kind of what I interpreted into it. Yeah. I love Pod Quiz, but they didn't want our money, which is fine.

Courtland Allen: 21m 12s

Was there any one dark ether in particular that just has been responsible for you being able to grow your revenue 10X or there been just a few, you know, like that podcast ad really worked out and like maybe a few other things?

Collin Waldoch: 21m 24s

It's the plurality game, not a majority game for sure. SEO helps. We invest in content marketing, but stereotypes are grounded in truth. The stereotype that SEO takes a long time is real. You got to put a lot of content out there for a long time.

It feels really good. All of the endorphins fire in my brain when an article goes to the front page of Hacker News, but then, 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 a series of lectures. We did a lunch break trivia game every day and there were hundreds of HR professionals there that helped. Slack featured us in a couple of posts.

PR is super helpful. 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 mid article placement of us, $3K in ARR just based on all our conversion and funnel stuff.

I mean, you can do the math backwards there and it's like, oh, it's probably worth investing in PR more. We paid for a PR firm, they got two not very good placements for us. Then all of our really good placements was just me cold emailing journalists, just straight up elbow grease and just badgering them.

Courtland Allen: 22m 42s

It's cool having a low churn business where it doesn't really matter where you get your customers from, they tend to keep doing trivia because it means that you kinda rest easy not having found this one channel to end all channels that works, you know, forever until the end of time. You'd be like, this end has kind of stopped working, but that's fine because all the customers they got are still going to stick around.

I just got to keep doing the elbow grease thing as you call it, keep hitting different targets, keep hitting different channels. 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?

Collin Waldoch: 23m 19s

I actually think this can be so much bigger. The product right now can 10- to 20X, no doubt, no question, no improvements. It doesn't mean it will happen. It certainly doesn't mean it would happen quickly, but it can do that. We only have 800 groups and the diversity of companies that use it is pretty remarkable.

Now I'm realizing we got 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.

One thing we did is it's asynchronous team building. When I look around, pretty much everything is synchronous and it's everyone get together. I don't think people like having things in their calendars. I think it's anxiety inducing for a lot of folks.

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.

We've really worked hard to build asynchronous team building as a core concept, where we’ll feature little anecdotes of how Courtland knew that really hard question in the results. So, you're still kind of getting to know Courtland and sparking conversation, even though he answered the trivia with his morning coffee at 9:00 AM and I did it over at lunch with my fiancée.

I'm thinking a lot bigger now about asynchronicity team building in general. 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 trivial 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 a Slack, and then Google Forms and this and that. I think you can do a lot better. We’re working on a live event platform basically as an add-on to our subscription business.

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 wordplay 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. I'm somebody who I think thrives in working within constraints.

Courtland Allen: 25m 15s

Constraints are good. It's smart to have constraint because they are the things that have gotten you to where you are now and the danger is that once you get too starry eyes, you lose the constraints.

You sort of lose a little bit of your magic. I've dealt the same thing with Indie Hackers. 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. Then it was like, all right, boom. Your goals are completely different. They're a thousand times bigger.

For you, you’re like 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.

Collin Waldoch: 25m 53s

It’s made me more opinionated, which is fun. 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 that I was 12 months ago. I'm more willing to, I guess have stronger opinions.

Courtland Allen: 26m 10s

Are there any guiding philosophies or mental models or books that sort of guide how you run your company or how you live your life?

Collin Waldoch: 26m 17s

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. 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 not a 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 two personal relationships to anything.

But the biggest is probably been the book “Moonwalking with Einstein”, which is about memory palaces and remembering things.

Courtland Allen: 26m 55s

One of my favorites. Super cool book.

Collin Waldoch: 26m 57s

Yeah. Joshua Foer. I mean, him and his two brothers are all phenomenal writers. Actually, Foer 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 and remembering trivia facts but there’s this one line that's monotony compresses time, novelty unfolds it.

I'm a huge believer in introducing novelty in any way, shape or form to just multiply the number of things you remember. Essentially our memory of our life is just how many signposts you have to look back on.

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. I would way rather have a super densely, memorable life until 70. It just matters more.

Courtland Allen: 27m 42s

I did an episode maybe a year and a half ago now with the creator of an app called One Second Every Day. 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've got a six-minute video of your entire year.

The cool sort of side effect of it, it's not just having this video. Instead, the video itself motivates you to do more interesting things because you don't want to have the same one. In May during the pandemic, my one second video every day, was me and my computer. I'm like, this has got to change.

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 live a different life. So, I'm right there with you, like novelty, what'd you say unfolds time and gives you just more memories and that makes it seem like your life is much longer.

Collin Waldoch: 28m 28s

Yeah. I have a thing. This is the sixth year where I buy a physical calendar, a wall calendar. I'll write one thing each day. The only rule was it couldn't be about work. It's in Sharpie, it's two words. Literally, I have to write one thing each day. But it's a tiny square and I have a Sharpie, so truly we're talking micro tweet things here. I can look back in the last six years and look at one thing every single day.

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. Then I'll use basically the photos in my phone, my calendar, run or fitness tracking app to just recreate, like there must have been one thing that day. Looking back, I'm like, arid that not much going on, but it's so nice to look back and find things.

I think of it as a poor man's time hope, but I'll look back to past year's calendar sometime and be like, oh, April 13th, 2018. It'll be like lunch and walk with JU or something cause I just do initials for people and I'll text JU be like, yoooo. Poor man’s time hop.

Courtland Allen: 29m 33s

I know Facebook used to do that thing all the time where you would sign on and it would five years ago today, you and this friend were tagged in this photo, tag both of you. I'm never on Facebook anymore, but that was kind of cool. It was a good way to connect you to your friend.

Collin Waldoch: 29m 44s

Apple's been doing more and more of it where they put, with the widgets and stuff on the new iOS home screens where they surface photos to you. I dunno, 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.

Courtland Allen: 29m 59s

Yeah. My Google photos is constantly, six years ago today, you were doing this this fun thing. Don't you wish you were back there? I'm in my apartment or in the pandemic, like, yes. It's a matter of fact.

Collin Waldoch: 30m 9s

Thank you for feeding me into your sentiment analysis.

Courtland Allen: 30m 13s

I feel very taken care of.

I just Googled eustress because I'd never heard of this term that you brought up earlier. These two different types of stress. It's totally real. It says eustress is a kind of doable stress. This article’s apparently written by a Dr. Core, so if they're a doctor, it must be true. 
 You're faced with the challenge but a challenge that you can handle and you actually look forward to handling that challenge. So, you feel out of your comfort zone a good way.

Collin Waldoch: 30m 38s

Yeah. Let's do it live.

Courtland Allen: 30m 13s

Yeah. We'll do it live. That to me encapsulates kind of the startup journey. 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 but I'm looking forward to trying it. 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, right?

You want to have problems that you really, you wake up excited to solve because problems are kind of the thing that pull you forward in life. They get you motivated to do something. 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 I guess that's distress and you feel terrible.

But if you have good problems, then you wake up every day, super motivated, super excited. You have something that you're running toward. I've tried to structure my life like that for the last 10 years. You know, what could 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 kind of a common idea from psychology. I'll let you explain it because you actually have 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 and then forgot about it. But you've been like living in the peak end rule.

Collin Waldoch: 31m 49s

Yeah. Well, I mean, basically read it and forget it is my mantra for everything, but then when you read it the sixth time, it’s harder to forget.

As I noted before, I'm really interested in how we remember things and not into I want to study neurons my whole life way but just in 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? Think of one experience, like a sports game you went to, a life event or a job or a grade in school, like the whole eighth grade or whatever. You're probably gonna remember two things on average. You’re gonna remember the peak. I think it as the spikiest experience, the most bad or the most good.

Courtland Allen: 32m 27s

The most extreme part that happened.

Collin Waldoch: 32m 28s

Yeah. It can be anything. Then if you think about the end, people just think about their endings a lot. How you typically remember that experience, there's been psychological studies of how bad or good you remember that experience essentially as the average of the peak and the end.

It's really hard. It's impossible, in a good way, to control the peak of anything. It's going to a Cubs game at Wrigley Field, and I choose for there to be a grand slam right now and the whole crowd to erupt. You can’t choose that. It's going to happen or it's not.

But I think you can control the ending. I think people can control the ending more, and it ends up weirdly perversely, improving your memory of so many things in life. If you control the ending, people talk about going out on top, ending too early instead of ending too late, I'm a massive fan.

I've seen it. I think I mentioned 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 & Co, consulting company and people leaving, they just treat you so well, that's the greatest exit experience. 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 have you boomerang back as an employee. It's not purely altruistic, but they treat you really well on the way out the door. People send really nice, thoughtful, goodbye emails.

I know this stuff happens at a lot of companies, but even at the exit interview process and helping you find a new job and this and that, it's really excellent. I think it's what allows you to be regarded as a really good employer, just because you control the end experience.

You're not gonna control their peak experience because maybe they had a lot of 3:00 AM nights in a row making slides, but you can control the end experience and if that color is disproportionately twenty-four months of labor, then wow, that's super good ROI.

Courtland Allen: 34m 9s

Yeah. I have a friend who does this. He came to visit me from Russia. 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? He's like, no, I'm going to be here for two nights. I’m like, two nights?

He's like, look, always under stay your welcome, never overstayed your welcome, because then the end is going to be like, it was too soon. You just got here, everyone's going to want you to stay. Then the memory of that trip is going to be great, but you stay 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. Then that's the ending of the trip and it sucks.

Collin Waldoch: 34m 43s

I think about it a lot for trips, especially. One thing I do that I stole from someone is the alphabet game at the end of every trip I take. My fiancée and I just lived in New Orleans for a month, and we just did the alphabet game about New Orleans.

You come up with some memory for all 26 letters to represent that trip and you do a long list. Then we go back through it and choose one thing. Now you have 26 things to remember from that trip. You do it in the airport or the car on the way out of town. Then you take a picture of it, and you make it a poster and do whatever.

You have so explicitly controlled the ending of that trip by summing it up into the 26 best food items and inside jokes and places. It's amazing that will color the entire memory of your trip, which is a little internally, manipulative, but alas.

Courtland Allen: 35m 31s

Are you doing this somehow with Water Cooler Trivia? Are there ways that you're affecting the endings of you running this business to make sure that it's a good memory?

Collin Waldoch: 35m 40s

One thing that I really want to is do what we call, such a lame name and I love it, quarterly learnings. It's this feature idea that I've had forever. It’s like quarterly earnings, but with an L. It's like the year in review from Spotify or Lyft or whatever. It basically just sums up the last three months of trivia.

We email, like the Indie Hackers team, here's your quarterly learning. Courtland was the rookie of the quarter. He was new to the team and did the best. Most improved was Collin and the worst at that geography was so-and-so and the best anecdote with so-and-so.

I really love the idea of capping a quarter. Just giving timeframes on things is really helpful. Perpetuity weekly trivia is really nice, but we have the leaderboard that resets every month and being able to do short-term and long-term duration simultaneously is really important. I think about endings in that way.

Courtland Allen: 36m 23s

Cool. 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 we add a custom category and get you making Indie Hackers- related trivia questions, I'm pretty sure I can do pretty well.

At the end of these podcasts I always ask the same question, Collin, which is what have you learned from your journey that you think fledgling indie hackers who are just getting started can take away?

Collin Waldoch: 36m 47s

Yeah. I mean, I think it is not as simple, but I think it’s as real is just say yes to life. The reason Water Cooler Trivia started is because honestly, I went out on a Wednesday night to watch a US soccer game and I invited this friend. Then we were just talking about these emails I had been sending and he was like, I have an engineer roommate.

I can't 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 has an outside chance of 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 it. That's the best way to write trivia, 10 things you want to know the answer to.

It was just because I was biking home and the bar looked fun, so I sat alone and wrote 10 questions on a napkin. I think the more you just say yes, the more I consider those darts thrown, good things can happen. I'm not sure how much I believe in luck. Luck is the residue of preparation or whatever, but I'm certainly a believer in good things is the residue of trying a lot of things that could end up good.

Courtland Allen: 37m 50s

Your framework, elbow grease and darts. I love it.

Collin Waldoch: 37m 52s

Yeah, elbow grease and darts, that's life. That's life.

Courtland Allen: 37m 55s

All right, Collin. Well, thanks for coming on the show. Can you let listeners know where they can go to find out more about Water Cooler Trivia and your very ambitious feature plans?

Collin Waldoch: 38m 4s

It’s watercoolertrivia.com, it’s exactly what it sounds like. We also recently purchased trivia.co. This is admittedly kind of massive buyer’s remorse 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.

Next up, we are moving the chicken. We are growing to a lot more teams and gonna 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 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? I took no salary the last year. You can only do that so many years.

Courtland Allen: 38m 51s

All right, well, I'll be following along and maybe you can come back on the show if you end up emailing me to tell me you're at a million dollars in ARR quarterly, get me back on the show. Well, thanks again for coming on.

Collin Waldoch: 39m 2s

Of course, Courtland. Thanks.