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Home/The SaaS Podcast/Episode 65
Why Startup Traction Means Retention Not Signups
Walter Chen, iDoneThis

Why Startup Traction Means Retention Not Signups

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Episode Summary

Walter Chen quit his job as a big-firm lawyer, built a side project called iDoneThis, and turned it into a SaaS with investors including the CEOs of Zappos, Shopify, and Wistia. But his biggest lesson about startup traction almost came too late.

In this episode, Walter reveals why obsessing over signups nearly killed the business, how a single customer email led to Shopify's CEO investing, and the co-founder mistake that nearly collapsed the company right after raising money.

Walter Chen is the co-founder and CEO of iDoneThis, an email-based productivity tool where teams track what they accomplished each day. You reply to an evening email reminder with what you did, and the next day everyone gets a digest of what the team got done.

Walter started as a lawyer at a big New York firm before quitting to build software. iDoneThis was never supposed to be a business - it started as a side project to help his co-founder Rodrigo stay accountable for diet and exercise. They launched it on Hacker News, got hundreds of signups, and realized they had stumbled onto something people actually wanted.

The team went through AngelPad, raised $380K, and started building startup traction through content marketing. But Walter learned the hard way that signups are a vanity metric. iDoneThis had a retention problem - the daily commitment model made users feel guilty when they missed a day, and once they dropped off, they rarely came back.

Walter also shares the costly mistake of bringing on a random co-founder who quit during AngelPad, nearly causing all their investors to pull out. And he reveals how noticing that Shopify CEO Toby Lutke had signed up for the product led to a visit to Ottawa, a relationship, and an investment. The same pattern with Zappos brought Tony Hsieh on as an investor after a content piece on Business Insider caught his attention.

Topics: First Customers|Product-Led Growth

Key Insight

iDoneThis co-founder Walter Chen grew the product to 1,000 paying customers by using Hacker News content as the primary startup traction channel, but learned that total signups were a vanity metric hiding a serious retention problem. The real traction came from noticing high-profile users in their support inbox and building relationships that turned customers like Shopify CEO Toby Lutke and Zappos CEO Tony Hsieh into investors.

Key Ideas

  • Launched on Hacker News with a coordinated upvote strategy, then drove repeat front-page appearances with weekly content articles
  • Focused on total registered users as a traction metric while ignoring a retention problem where daily commitment made users feel guilty and drop off
  • Noticed Shopify CEO Toby Lutke had signed up, emailed him, flew to Ottawa for a week, and turned the relationship into an investment
  • Zappos CEO Tony Hsieh found iDoneThis through a Business Insider article, which led to a meeting in Las Vegas and an investment
  • Brought on a random co-founder during AngelPad who quit, nearly causing all investors to pull out of a $380K raise

Key Lessons

  • 🎯 Startup traction is retention, not signups: iDoneThis focused on total registered users as a vanity metric while ignoring that users dropped off once they missed a day. Real traction means people keep using and paying for the product.
  • 🤝 Read your support inbox to find startup traction opportunities: Walter noticed Shopify's CEO had signed up by personally reading the support inbox. He emailed Toby Lutke, flew to Ottawa, and turned a customer into an investor.
  • 📉 Never casually assign the co-founder title: Walter gave a college roommate the co-founder title without thinking through consequences. When Jay quit during AngelPad, investors nearly pulled $260K because the team had changed.
  • 🚀 Double down on the startup traction channel that already works: After Hacker News drove iDoneThis's first hundreds of signups, Walter wrote weekly articles to stay on the front page instead of trying unproven channels first.
  • 💰 Content can attract investors, not just users: A Business Insider article caught Zappos CEO Tony Hsieh's attention, who forwarded it to executives. That single article created a chain that led to an investor relationship and a high-profile logo.
  • 🧠 Side projects can become real businesses if people care: iDoneThis started as a personal accountability tool for Walter's co-founder. They never made a conscious decision to turn it into a business - they just kept building because it was the first thing anyone actually used.

Chapters

00:00Introduction
01:40Walter's personal background
02:23What motivates Walter
03:49iDoneThis target customers and pain points
05:00From big-firm lawyer to software entrepreneur
07:01How the idea for iDoneThis started
08:37When the side project became a business
10:11How early users found iDoneThis
11:23Joining AngelPad accelerator
13:00How much funding was raised
13:43The co-founder mistake that nearly killed the company
17:29Lessons about choosing co-founders carefully
18:26When meaningful traction started
19:50The retention and churn problem
20:33Customer acquisition through content marketing
22:52Reaching 1,000 paying customers
23:29Why simple products win over copycats
25:44How iDoneThis landed Zappos, Shopify, and Uber
29:32Turning customer relationships into investments
30:42Building genuine connections vs networking

Episode Q&A

How did iDoneThis get startup traction with its first users?

Walter Chen launched iDoneThis on Hacker News with a coordinated upvote strategy and optimized subject line. The post hit the front page, The Next Web picked it up, and hundreds of people signed up immediately.

Why did Walter Chen say iDoneThis had a startup traction problem despite growing signups?

iDoneThis was fixated on total registered users as a vanity metric while ignoring retention. The daily commitment model made users feel guilty when they missed a day, and once they dropped off, it was nearly impossible to bring them back.

How did Walter Chen turn content marketing into startup traction for iDoneThis?

After the initial Hacker News launch worked, Walter doubled down by writing weekly articles. He studied what subject lines performed best, replied to all comments, and eventually expanded content distribution beyond Hacker News to publications like Business Insider.

How did Shopify CEO Toby Lutke become an investor in iDoneThis?

Walter noticed Toby had signed up by reading the support inbox carefully. He emailed Toby, asked if the team could visit Ottawa for a week, and Toby said yes. They spent a week in the Shopify office, met the exec team, and Toby invested.

What co-founder mistake almost destroyed iDoneThis during AngelPad?

Walter casually gave a college roommate the co-founder title without vetting the decision. When Jay lost interest and quit, investors who had committed $260K nearly pulled their money because the team composition had changed from what they invested in.

How did a Business Insider article lead to Zappos CEO Tony Hsieh investing in iDoneThis?

Tony Hsieh read an article Walter wrote on Business Insider and sent it to his executives. One of them, Will Young, signed up for iDoneThis and connected Walter with Tony. After visiting Zappos in Las Vegas, Tony invested.

Why did Walter Chen quit his job as a lawyer to build iDoneThis?

Walter had coded for fun since childhood but went to law school on a whim. After practicing for a couple years in New York, he reconnected with friends in tech around 2009-2010, kicked around startup ideas, and eventually quit to build software.

How much funding did iDoneThis raise through AngelPad?

iDoneThis raised $20K from AngelPad directly, plus $100K from two VCs alongside the program. After completing AngelPad, they raised another $260K, bringing total funding to $380K by end of 2011.

What did Walter Chen learn about the difference between vanity metrics and real startup traction?

Walter realized that smart founders laser-focus on retention and usage as traction indicators, not total signups. iDoneThis kept adding users but had a churn problem, meaning they were spending resources acquiring users who would not stick around.

Links

  • iDoneThis: Website
  • Omer Khan: LinkedIn | X
Full Transcript

Omer (00:11.840)
Welcome to another episode of the SaaS Podcast.
I'm your host Omer Khan and this is the show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business.
Today's guest is Walter Chen.
Walter is the co founder and CEO of iDunthis, an email based productivity tool that allows people to track their productivity with a daily email reminder.
You reply to an evening email reminder with what you did that day and the next day you get a digest with what everyone on the team got done.
The company was founded in 2011 and its investors include folks such as the CEOs of Zappos, Shopify and Wistia.
Walter is a software engineer and a former big law firm lawyer.
This is part one of the interview with Walter and in this episode we talk about why Walter quit his job as a lawyer to launch a SaaS business.
How I done this was just supposed to be a side project, not a business.
Why?
Bringing on a co founder was one of Walter's biggest mistakes, the single most important metric that many startups ignore, and how a single email to a customer resulted in a high profile investor.
So with that, let's get back to the interview.
Walter, welcome to the show.

Walter Chen (01:40.430)
Yeah, thanks for having me.
I appreciate it.

Omer (01:42.670)
Now I gave the audience a brief overview of your product and business, but tell us a little bit about yourself personally.
Who is Walter when he's not working?

Walter Chen (01:54.350)
Yeah, you know, I'm 31 years old.
I used to be a lawyer and a software developer.
So I used to code for fun and that kind of thing.
And in my free time now I mostly hang out with my girlfriend and play soccer.
Grew up playing soccer.
So yeah, so I'm just your average software developer plus lawyer plus casual soccer player.

Omer (02:23.760)
We like to kick things off with the success quote to better understand what drives and motivates our guests.
Now I know you're not a quotes guy, but what, what drives and motivates you?
What gets you out of bed to do what you do every day?

Walter Chen (02:40.080)
Yeah, that's a good question.
You know, I think it is actually sort of a deeper question than sort of like a one off thing.
I think one of the things that really motivates me is just doing right by the people who trust in you and who put their confidence in you.
So sort of try to make your parents proud and your friends and your employees and your investors.
That's like one of the main things.
And yourself.
And that's one of the main things that sort of Inspires me and gets me going in the morning.
But you know, some days you forget like why exactly you're, you know, why exactly you're doing what you're doing.
And so for me, like, and we recently had kind of one of those moments where it's like, wait a second, why are we doing what we're doing again?
And so there's always like opportunities to reflect and sort of renew and find new reasons to do what you're doing.
So yeah, but I think at the core it's always sort of, for me it's like doing well by yourself, doing the best that you can and by the people who care about you.

Omer (03:49.060)
Now let's start by giving the listeners a better understanding of I done this.
Who are your target customers and what's the pain point that you're trying to solve for them?

Walter Chen (04:02.100)
Yeah, it's a great question.
So most of our target customers, most of our customers are software companies, tech companies of size, two people, all the way down to two people, to thousands of people.
Most of them are in the range of 20 people.
And they really use this because it's a huge problem to just figure out what everyone's working on and what everyone's getting done.
So it's just that sort of syncing up problem.
Some people try to solve this with email or daily standups and for various reasons, those can often be inefficient or, you know, annoying painful in various ways.
So yeah, we make it really easy to know what everyone's working on.

Omer (04:43.320)
Now I want to talk about where you got the idea for this product, but before we get into that, I want to talk about your background because it's just so fascinating.
And how does a big firm lawyer become a software entrepreneur?

Walter Chen (05:00.840)
So there's actually, I actually meet a lot of people, former lawyers who are doing startups now.
So maybe it's actually kind of like a tight fraternity.
Maybe I know all of them.
But yeah, so I grew up, so I grew up coding for fun and I actually, my dad's a math professor, so I always did a lot of math growing up.
And when I got to college, like I thought, you know, I was trying to figure out what I want to do with my life.
One of the things I actually enjoyed doing for fun was, you know, coding and that kind of thing.
So I thought, hey, maybe I'll do computer science, maybe I'll become a software developer.
But I remember, you know, CS in college is like a lot of like, for whatever reason, I don't know, I can't Even remember why now.
But it's a lot of, like, staying up all night to finish projects.
You know what I mean?
It's like, you know, you're just, like, always pulling all nighters.
And during one of these all nighters, I was thinking to myself, here I am doing another all nighter, hanging out with a bunch of dudes in a sweaty computer lab.
I think I want to do something different.
So that gave me.
So it kind of gave me the idea.
I always liked to read and write, and so I thought, maybe I'll be a lawyer.
Maybe I'll go to law school and be a lawyer.
So it was kind of like on a whim.
There was no good reason.
I always liked reading John Grisham books growing up and watching Matlock and stuff.
Although those are terrible reasons.
I was gonna say.
Yeah, so.
But, you know, so I ended up going to law school and being a lawyer.
I practiced for a couple years, and I practiced here in New York.
And then, you know, I was kind of getting sick of what I was doing.
And I was reconnecting with some friends who were.
Who wanted to do something in tech.
This was like 2009, 2010.
It was like kind of 2008 to 2010.
I reconnected with some friends, and we kicked around ideas, and finally I decided to quit my job.
And that's how I ended up doing you back in sort of like software and technology after being a lawyer.

Omer (07:01.750)
So tell me more about how you came up with the idea for I done this.

Walter Chen (07:07.990)
Yeah.
So my co founder, Rodrigo, who is the CTO, when I quit my job in September of 2000, I think it was 10, we had this idea, Rodrigo and I.
He was doing a PhD in physics at Northwestern, and he wanted to drop out too.
So he had that.
We had this.
We kicked around a bunch of ideas, okay.
None of which were connected to, like, our own experience or anything like that.
They were just a bunch of random ideas, you know, that we thought would potentially make for a good company.
So one of those ideas was like, this apartment rental application thing.
And so we started it with this third guy, and I moved to San Francisco and we ended up building it.
But, you know, while we were doing it, we were just like, hey, we're not really that interested in apartment rental applications, doing them online, even though it could be an interesting business.
Like, we just weren't interested in doing it.
So I decided I was going to go back to New York.
But before I went, Rodrigo and I built this side project that was his idea that became My done list, which was basically, he wanted something that would keep him accountable for diet and exercise because he was, you know, at that time, he had become, like, pretty overweight and that kind of thing.
So he wanted something to bug him every day to keep him accountable.
And that is.
And I did.
So that became.
I done this.
I done this was just something for an individual to keep what they keep track of what they got done every day.
And then over time, it evolved into something that companies and software teams would use to stay in the loop on what they were working on.

Omer (08:37.330)
Wow.
Okay.
So you built this initially for Rodrigo.
At what point did you guys decide that this was gonna become a product and a business for you?

Walter Chen (08:51.220)
Yeah, it's an interesting question, because there was never.
I mean, you know, I think it's.
We never actually made.
And this could have been a mistake, but we kind of just fell into working on it more and more, even though we never really made a conscious decision like, oh, we're gonna turn this into a real business.
It was just, like, the only thing we had going on at the time.
So we just kept working on it more.
And so that's good and bad one.
It's like, you know, if I actually had put more thought into, like, what the point is, maybe I wouldn't have kept working on it.
On the flip side, like, you know, it's always good.
We always.
Later on down the road, we had these sort of crises.
Like, you know, why are we working on this?
We just happened to choose to work on this.
So what ended up happening was, like, it was the first thing we had built that anyone, not any, like, even a single person, cared about, because, like, everything else we had built before, it seemed like nobody cared.
But with Idunnis, we built it, and we had hundreds of people sign up immediately, and some of them kept using us and telling us that they liked it.
So that's why we kept working on it.
And so we launched it in January of 2011, and then we just kept working on it on the side.
And then eventually, In June of 2011, we decided that we were going to work on it full time.

Omer (10:11.260)
So initially, you were just, like, working on it and just making it better for Rodrigo?

Walter Chen (10:17.580)
Well, for Rodrigo and the few and the hundreds of people that were using it.

Omer (10:22.460)
How did those other people find out about it?

Walter Chen (10:25.740)
Yeah, so we didn't have any sort of brilliant launch strategy or anything like that.
And, of course, I'm not.
So getting 100 people to sign up is not.
It doesn't represent, like, success for Most people, it's just for us, you know, but the way we did it, we just put it on Hacker News, like that's all we did.
And.
Oh, we not only put it on Hacker News, but we got a few of our friends to upvote it.
So we got a few of our friends upvoted and we sort of did a little study on what the subject line should look like for a successful post and, you know, had a little bit of strategy around.
Okay, we're going to make sure we're on top of it.
We're going to reply to all the comments, people who commented, etc.
And so after it got uploaded to the front page, some other publications picked it up.
So the Next web wrote about it and some other people wrote about it.
And that's how it really, it sort of picked up Steam.

Omer (11:23.510)
Okay, and then what happened in June?
So you said you guys decided to kind of launch it as a product then?

Walter Chen (11:31.210)
Yeah, so we, we, we applied to different incubators.
Like for a certain group of people, like, the only way they know how to start a company is to like, apply to all the accelerators, right?
And that was us.
Like, we were like, we didn't know what to do.
So we're like, okay, we'll apply to like, you know, Y Combinator or whatever, you know, Techstars.
And we applied to this other accelerator called AngelPad based in San Francisco.
And.
And we ended up getting into AngelPad.
And it was.
The thing about AngelPad is it was run by ex Google people.
So a bunch of ex Google executives started this accelerator.
And so the reason why that's a connection or that's relevant is because at Google they had a system called Google Snippets, which was something that would send the whole company email every week asking what everyone was working on.
And it was very similar to, I'd done this at the time I'd done this was just for individuals.
So it was very similar to I did this except it was for the whole company.
And so these ex Google executives really loved it at Google and thought that it should be something that exists in the world.
And so when we talked to them, they were excited to fund us and have us focus on building a product for companies.
And so we, you know, at that.
So given that sort of validation, not just like sort of, we had, you know, grown the user base, but then we also had investors who were smart and who were interested in us, who, who had some vision, you know, who sort of like helped us cultivate a vision around it.
And then they funded us.
So we, you know, we.
And we turned it into a real company at that point.

Omer (13:00.880)
How much money did you initially raise?

Walter Chen (13:04.560)
So, yeah, from AngelPad.
So AngelPad was, you know, the typical, like, 20K deal.
And then alongside that, two VCs invested 100K.
So we had 120K.
And then.
And then we went through AngelPad.
And at the end of AngelPad, we raised another 360K.
So that brought our total to, like, you know.
Sorry.
We invested another 260k.
So that brought our total to 380k invested by the end of 2011.

Omer (13:33.050)
Okay, got it.
Looking back at those early days, what do you think was one of the biggest mistakes that you guys made?

Walter Chen (13:43.220)
Yeah, so one mistake that we made is actually funny.
You know, kind of funny to think about.
It is Rodrigo and I.
You know, none of this really makes any sense, like, when you think back about it, but.
So Rodrigo and I, we didn't really know each other that well.
We had known each other for a few years through a mutual friend.
But we had, you know, we had worked on.
I'd done this, and we had made it happen.
Right before we did AngelPad, I was in San Francisco.
This happens all the time.
This is just random stuff that happens in San Francisco.
I was walking around San Francisco, and I ran into my college roommate.
Okay.
Who I hadn't talked to since sophomore year of college because, you know, we lived in the same, you know, tiny room together and ended up hating each other.
Right.
As happens to college roommates.
I ran into him, but he's also one of the smartest guys I know.
So his name is Jay.
Because we were not only college roommates, but we were also CS partners in, like, you know, two classes, which was really stupid because, you know, we, like, learn to hate each other.
Anyways.
Anyways, he is still.
He was and still is one of the smartest guys I've ever met.
So I ran into him.
He had just quit his job at Yelp.
He was an early employee at Yelp.
He actually wrote the first version of the Yelp iPhone app.
So he was, like, legit.
He was doing his thing, but he was trying to figure.
He was kind of lost, so he was trying to figure out what he wanted to do.
So I said, hey, come work it.
I've done this without, like, you know, no, like, sort of thought behind it or vetting process.
To me, it was just like, here's one of the smartest guys.
I know he's slightly insane, but let's just Bring him on, See what happens.
Anyway, my co founder, obviously, Rodrigo, was really impressed by him because he's really smart.
And basically, through the course of AngelPad, the team disintegrated.
Jay, as he always does, lost interest in what we were doing and decided to quit.
And so when Jay decided to quit, we had already raised some money, but we hadn't put that money in the bank.
So they had invested based.
So we never thought that the title of co founder really meant anything.
It was like we could just give the title co founder to anybody, right?
But it turns out all these people because they had invested in a team of me, Rodrigo and Jay.
When it turned out Jay was going to leave, they were all going to take their money out, they were all going to not invest.
Right.
And that makes total sense to me, thinking back on it.
But when I was going into it, I was just like, yeah, I thought it was actually very possible that Jay would leave, but I didn't think that there would be any repercussions.
I'd be like, oh, yeah, if Jay left, we'll just get the code that he wrote for free.
You know, that would be awesome.
Right.
But it turns out there are real consequences because everyone invested.
Like, we had gone through everything thinking that we called Jay co founder.
Everyone thought that Jay was co founder.
And when Jay left, it was almost like, you know, everything was going to collapse.
And because Jay was in a three person team, like the team kind of, the team dynamics changed dramatically.
And Rodrigo and I almost didn't talk through the last couple of months of Angel Pad because, like, of the way the team dynamics changed.
So basically the whole team almost fell apart.
But at the end, Jay and I, sorry, Rodrigo and I got together, recommitted to working on.
I had done this, called all the investors and told them that the team was Rodrigo and me and told them to stick with us.
And they did.
And then Jay left and moved on to, you know, Jay left and moved on to other things.
And so, like, one of the big mistakes we made early on, in short, one of the big mistakes we made early on was taking on a random co founder and not really thinking about it and thinking there would be no consequences and then having, you know, and then having to sort of like deal with the fallout from him leaving.

Omer (17:29.629)
Yeah, I mean, that's a key lesson, right?
I mean, you've got to hire carefully, but you've got to be even more careful about who you bring on as a co founder.
Right.
And I hear a lot of people saying it's like getting married, right?
You've got to think of it almost like that.

Walter Chen (17:46.669)
Yeah, absolutely.
I mean, I think that's well put.
And so, yeah, you know, I think one of the harder, like, and you hear this all the time, it's like one of the hardest things to fix in your company is like your co founder relationship because, like, you can fix the product, you can fix like the market.
You can choose a different market, but like, if you choose a different co founder, you think you can do that.
Like if you, you know, you think might think going into it, oh, yeah, I'm gonna get this sweet co founder.
We're gonna raise 2 million bucks.
V leaves.
No big deal.
But like, it never plays out that way because like when the co founder leaves or, you know, it makes it much more difficult for you in the eyes of others and in reality

Omer (18:26.240)
looking, I guess that's not looking back.
We've done that.
So at what point did you feel like you were getting meaningful traction with the business?

Walter Chen (18:40.160)
Yeah, so that's a good question.
So for us, and you know, the standards have changed a lot, you know, so, you know, I would say actually it's a really good question fundamentally, because I would say this, like, we actually thought we had amazing traction just because even a single person used it and liked it.
You know, on the flip side, like, I think you can fall into a trap where it's like.
And we fell into this trap where it was like we wanted to add more users and we just thought that, like, that meant traction.
But early on we had a retention problem and so.
But we couldn't.
But we had just sort of like fixated on this idea, this sort of like vanity metric of like total number of registered users.
So whenever we were adding users, we felt like we were adding traction, even though, you know, we continued to have like this retention problem.
So I think the smart people, the smart people who look at traction early on really focus laser in on like, you know, retention and like usage and value.
I think people who.
Yeah, I think the mistake that I made and the mistake that a lot of people make is like focusing on big numbers and total number of signups and that kind of thing.

Omer (19:50.600)
So what was the churn problem that you guys were having?

Walter Chen (19:54.440)
Yeah, it's just that, you know, that people really loved I'd done this early on and because, you know, they're like, oh, wow, you know, I'm getting stuff done, but it kind of demanded that you do it every single day, you know, and like, imagine doing, using some app every single day for like the rest of your life.
Like, you know, it's, it's hard to imagine.
So once someone dropped off, it was hard to bring them back on.
So because it was kind of like this commitment accountability app.
So like it kind of made you feel bad about yourself when you didn't do it.
So I don't think that's like long term sustainable.
So that was sort of like the main problem there.

Omer (20:33.150)
Okay, so you've got investors, you know, you're getting through some of these challenges, I guess, both on the co founder side and the customer retention.
What kind of things were you doing to attract more customers?

Walter Chen (20:54.190)
Yeah, so what?
So I think the fundamental piece of advice on this that I got, that is true and this is obvious, 100% obvious, but sometimes you forget about this, which is just double down on what's worked.
So I told you early on we got, you know, we got on the front page of Hacker News and a hundred, you know, hundreds of people signed up.
Well, early on we're like, okay, let's get on the front page of Hacker News every week, right?
So we started writing this blog and you know, we would write articles about that were related to, you know, related to the stuff we were working on.
So like for example, there was this idea of like Jerry Seinfeld Productivity Secret where like, you know, every day Jerry Seinfeld would make sure that he wrote a joke and then he would put an X on a calendar when he did write a joke.
And getting a streak of X's on the calendar would motivate him.
So we wrote about that concept and put, and I'd done this kind of spin on it, wrote an article about it and then pushed it to the front of Hacker News using the same tactics that we had done in the very first launch of IDunless.
And so we were consistently able to appear on the front page of Hacker News with different articles.
And it would just drive more and more signups.
And then what that grew into was sort of like a.
But the problem.
So that was good.
It got us visible, it got hundreds of signups.
The problem was that it was like a, you know, it was like this sort of like hit based, kind of hit based acquisition model because like if the article didn't appear on the front page, you would have spent hours writing an article that nobody read and there would be zero signups, you know, so it would be either be hundreds or zero.
Right.
Hundreds, thousands or none.
Right.
And people started complain, you know, aren't always happy to see the same article.
You know, the same company have articles on front page of Hacker News.
So it sort of turned into this generalized content marketing strategy where we are creating content and not only getting distributed through Hacker News, but getting distribution through other channels and then driving, you know, signups through content.

Omer (22:52.170)
How many users do you have today kind of actively using the product?

Walter Chen (22:58.730)
So right now we're focusing on more, you know, paying customers.
So we have like a thousand paying customers.

Omer (23:03.690)
Okay, cool.
Now, one of the things that really struck me about I done this is it's such a simple idea, right?
And.
And, you know, I think, you know, a lot of developers might look at something like this and say, I could build that.

Walter Chen (23:28.620)
Right.

Omer (23:29.020)
It doesn't seem to be doing that much.
Right.
What do you think was behind you guys being successful with this idea?
And also as you've grown and got more visibility and success with this product, have you had to deal with, like, copycat products out there as well?

Walter Chen (23:53.830)
Yeah, so we have.
I mean, it amazes me, but yeah, there are copycat products where I've done this and they pop up all the time, and it sort of blows my mind.
You know, it's kind of funny.
I think the reason for our success that a lot of these copycats are missing is that one, whenever you're a copycat, you're sort of.
You're coming at it from.
You don't necessarily have an organic reason driving what you're doing.
So you're not always able to come up with new good ideas.
And I think the.
So I think the main thing that drives, like, our success, one of the main things is it's trying to come up, you know, it's trying to really look at our customers and, like, the problem we're solving and come up with our own original solution and reason for doing things and not and, you know, like, really serve our customers needs and not just sort of try to copycat or follow someone.
Like, you know, I'm a believer that, like, the simplest products are the ones that, you know, like, a simple product can really deliver a lot of value.
And so it's not sort of just like the simplicity of it.
It's really just like honing in on what customers want and need and trying to solve that problem.
I mean, it seems kind of vague.
I mean, it is super vague, but I always feel like we were able to articulate, you know, a reason for our product existence.
And this is part of, like, doing content early on.
It sort of makes you think a lot about, like, why you're doing things and what how you can express it in a way that's really interesting and compelling to people.
But it's like we were always able to think of like an interesting, compelling reason and twist on why I done this works and is meaningful.
That like, you know, that appealed to someone enough to sign up for it.

Omer (25:44.170)
You know, it's.
I look through the site and it's really impressive in terms of the companies that you have listed there from Zappos, Twitter, Foursquare, Shopify, Uber, Heroku, Reddit, the list goes on.
How did you reach these people?
Was it really all through Hacker News?

Walter Chen (26:08.070)
So it was a lot through Hacker News, but it wasn't, you know, it wasn't.
I told you.
Sort of we expanded Hacker News, sort of.
We started with Hacker News as a distribution channel for content, but we expanded.
So we ended up having loss of distribution for our content apart from Hacker News.
So for example, it turned out, you know, I ended up talking to Will Young, who's become a friend.
So Will Young is head of Zappos in San Francisco and he learned about I'd done this because the CEO Tony Hsieh read an article that I wrote on Business Insider and he sent it to some of his execs.
And so one of them reached out.
So one of them was Will.
And he ended up signing up for.
I'd done this and then we became friends.
So, you know, a lot of it is.
So a lot of it was that writing content in a way that was sort of like high brow enough that an executive would, an executive of like the quality of like Tony Hsieh, Zappos would read it and say, that's interesting, you know, that's interesting.
I want to learn more about this.
And that's interesting enough to send it to other people in the company.
And then the second part of it was I was always in early on.
I and the rest of the team, we were always in our inbox, our support inbox, reading it closely, learning about the people who are reaching out to us.
For example, like early on I was in the inbox and what, you know, it just so happened that I got an email from Toby Luque, the CEO of Shopify.
And you know, we, and as a team, like we recognized who he was.
Which, you know, it doesn't always happen.
Like, you know, if you hire a random support person off Odesky, they won't nest, they won't know who Toby is apart from any random person.
Right.
We noticed Toby, CEO of Shopify had just signed up for our product.
And so we thought like, you know, we emailed back and forth with him and he's an awesome guy and he gave great feedback and, you know, he like shared his thoughts.
And I was talking with Rodrigo and we came up with the idea, like, hey, why don't we email Toby and ask him, can we go up to Ottawa, Canada, where they're based, and go hang out with him for a week, see how they're using iDunnit, see if we can get to know him better.
He emailed me back and said, that's an awesome idea.
Like, I wish more startups would do that, come up to Ottawa.
And we went to Ottawa.
We flew up to Ottawa for a week and they had us in their office.
They gave us desk there.
They, we met with all of their exec team.
Like, this is before.
This is when they're 100 employees and when they were like, you know, a $200 million company, now they're a billion dollar company.
Ipoing, right?
And they invited us in and we got to know them.
And then Toby ended up investing in iDubbbz.
And so like, it was like the content, but it was also sort of being opportunistic and seeing that opportunity and thinking about an interesting thinking about an interesting and creative way to get to know them better.
Right.
You know what I mean?
And it's always.
And I think one of the hardest things about hiring is teaching them, like, if I were going to hire a customer support person, one of the hardest things is teaching them to jump on these opportunities and like to see the opportunity, jump on it and do it in a way that's interesting, distinct in a way that only like someone that I'd done this could do, not someone who's at a copycat clone company, you know what I'm saying?
It's like infusing the company with that spirit that like you had when you're founders, where you're doing everything and you see these opportunities and you embrace them in an interesting way.
So, you know, that's kind of like how we got to know these people and like how we saw the opportunities and how we jumped on them.

Omer (29:32.950)
And both those guys, Tony Hsieh and Toby, are both investors in your company now as well, right?

Walter Chen (29:37.750)
Yeah, exactly.
And so, like, for example, with Tony Hsieh, like, I got to know Will and he invited us to their Zappos, you know, we were emailing back and forth.
We kind of hit it off.
He invited us to Zappos office in San Francisco.
It was super nice of him.
I met Will we got to know.
I got to know him better.
And he was like, hey, why don't you go, why don't you come to Las Vegas and meet with Zappos, you know, in Vegas?
And so I brought, you know, we got the team.
We went up and went to Las Vegas and will set up a meeting with Tony Hsieh.
And, like, I mean, we got to hang out with Tony for a couple hours, which is, you know, which is something that everyone wants to do when they go to Las Vegas.
But, you know, not many people get the opportunity because he's a busy guy.
But, yeah, it's just, you know, it was just sort of like, get, you know, sort of relating.
It's, you know, some people might call it networking, but I think it's really just sort of like relating with people in a human way, getting to know them and trying to, like, make.
Make your customer successful, that kind of thing.

Omer (30:42.090)
Yeah, no, I completely get you with that because, I don't know, personally, with me, I used to hear a lot about, you know, people telling me, you know, you should network more.

Walter Chen (30:51.620)
Right.

Omer (30:52.100)
And I just hated that word.
It just seems so.
I don't know, just insincere, like, you know, just trying to go and get something from somebody, and then eventually, I can't remember what it was, but there was some experience or some book that I read where it really just changed my perspective in terms of, you know, what.
It's just about making connections.
It's about finding ways to help people without expecting anything back.
And, you know, I think.
What was the expression, Harvey McKay?
I think it was the guy who wrote the book about dig your well before you're thirsty.

Walter Chen (31:29.290)
Right.

Omer (31:29.610)
And I love that analogy about, you know, just.
Just go out and just do this stuff, don't expect anything back, and eventually the good karma will come back to you in some shape or form, right?

Walter Chen (31:40.330)
Yeah, absolutely.

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