May 5th, 2020
Today I tweeted something and immediately regretted it.

It was pretty harmless/sarcastic, but overall, it was a condescending thing to say, with the guise of being clever and funny.

Looking back, it came off as "I'm better than you".

I don't want to be that guy. I don't want to make a living or be known for being critical of others.

Because, deep down, that's an insecurity of mine. I am really critical and judgemental of others, and I need to stop that.

One of the only ways I can stop that is by creating and working on my own things. The more energy I put into that, the less I'll care about what others are doing with their life.

If I can be less judgemental, then I will be a better person, I'll be more successful, and I'll live a happier life.

Maybe that will be my "hobby" for May. How can I be less critical/judgemental?
May 4th, 2020
(this is an excerpt of my monthly update email)

Note: Going forward, I want these emails to be less "matter of fact" and more genuine. More getting my thoughts on paper, and hopefully a more enjoyable read for you. (I will still continue to have full transparency as far as numbers).

April 2020:

April was a record month, for both traffic and revenue, which came as a surprise since March was so dismal. This was the result of (I think) two things:

(1) Coronavirus media mayhem has died down, but now people are stuck at home, on the internet, looking for something to do.

The response from 'How To Say No' has been crazy! The page has been visited over 50k times in the last month, and it continues to get traffic and people sharing it on Twitter every day. For me, this whole thing reinforces how important it is to think outside the box when it comes to marketing. Although the project is a bit silly, it has contributed to significant growth for both Starter Story and Pigeon. For Starter Story, it seems to have helped bump up our overall search traffic by at least 50%. And for Pigeon, it's driven ~300 users. I often think of Hubspot (a $5B+ company now) that attributes their early success to side project marketing.

A couple of big things on the Pigeon front:

(1) Pigeon is now a freemium product. I was a bit nervous about how this would go, but after seeing a month of data, I think it's the right move. We're seeing people sign up, kick around the product, become engaged with the product, and eventually pay for the product when they need some extra features, or reach a certain limit. I've also noticed a couple of other great things about this model: One, it's forcing us to think harder about onboarding, engagement, user experience, and design - we're now tracking things like daily active users, and cohort analysis and making decisions and goals from this data. This kind of thinking + freemium forces Pigeon to become a way better product, and that can already be reflected in the changes / new features we added in April.

(2) Pigeon will eventually be rebranded and become "a part" of Starter Story. I'm still thinking deeply about this and I don't know what we will call it, but the main idea is that I believe everything should just be "one company" and "one brand". Why run separate businesses? Starter Story will continue to grow into a big publication for business & entrepreneurship, and Pigeon is software that these entrepreneurs use to get their business off the ground. Content + software will be a really powerful combo, i.e. Hubspot.

On the Starter Story front:

(1) We tried launching a community for premium members, and it failed. The main issue was engagement, and we couldn't get people to write posts or contribute organically. We put a lot of effort into this, but after 2 months it felt like we should let it go. The obvious giveaway was when we had people signing up for the subscription, and not even joining the FB group... We will move away from the community and focus on what we do best - providing great (and premium) content on the website.

(2) We are doubling down on getting emails, email marketing, and overall monetization. Overall, we need to be more aggressive when it comes to marketing and selling, and letting readers know that we have a paid subscription. We made sweeping changes across the website (to get more emails) and are now collecting 3x the amount of emails than we were before. We also just built a real nurturing sequence to get people interested in the subscription. We also are testing out pages like this and this.


Numbers:

- Total Revenue: $9,184 (+6%)
- Starter Story Traffic: 700k pageviews (+42%)
- Pieces of content published: 104 (-4%)
- SS Email List: 13,500 total subscribers (+87% in net new subscribers)
- Starter Story Subscription MRR: $1.6K (+$100 MRR)
- Pigeon MRR: $1.3K (+$250 MRR)

Goals for May:

I'm trying a "less is more" approach to goals these days:

- 500 Daily Active Users For Pigeon
- Run a 10k every day
- Develop and scale more "automated" roundup articles for Starter Story ("business ideas for women")
- Develop and scale "templates" blog posts for Pigeon

Thanks for reading!
May 3rd, 2020
Lately, I haven't felt motivated.

Don't feel like I have "clear" enough objectives / I'm not really sure what I should be working on right now, or if I'm working on the right things.

I wish I had a clearer plan for the future - sometimes everything is so clear - sometimes it's not clear at all.

The days go slower during these unclear times, and I generally don't feel very happy or content...
May 2nd, 2020
Often I'll put off a feature for a while - often because it "feels" big.

Then, I'll go and build it, and then it's done in a couple hours.

Always happens to me.

Now, the harder piece here is determining if I should build these features in the first place.

I shouldn't build new features "just because" - or because one customer asked for it.

So maybe "putting off" these features is actually the right move. I put them off like this until it "feels" like I'm losing customers over it - or it "feels" really painful to not build the feature.

I don't think you can determine that right away. It's many days/weeks/months of customer feedback and then finally pulling the trigger.

Because, although it's easy to build the feature, this new feature is a new "weight" on the business. Technical weight, causes more bugs, more documentation, more changes in messaging, more onboarding, and potentially a more convoluted product...
May 1st, 2020
My main goal in life is to inspire people.

I don't talk about it much, but it is, deep down, the driving motivation for everything I do.

It's the reason I'm building businesses. It's the reason I'm writing right now. It's the reason I share my story.

Sometimes people tell me that I inspired them, and sometimes I get texts like these:

Text conversation with my old roommate


When I hear stuff like this, it makes it all worth it. No amount of money, followers, or social status can beat this.

This is true, organic impact that my story had on another human.

About a year ago, I wrote down my life goals. These are them.

My life goals

Why do I want to inspire?

Because there are people before me that made this decision - to inspire others through their art. It would be selfish if I only took in their inspiration, and never put that energy back into the world.

What matters is the people who are sparked by it. And the people who are like offended by it, it doesn’t matter. Because its about motivating the doers. Because I’m here to follow my dreams and inspire other people to follow their dreams, too.

- Kanye West
April 30th, 2020
I always feel like I need to level up, find the next "thing" to conquer, skill to learn, thing to improve.

Because my current situation is never "good enough" - there's always something to improve. Even if I had a million dollars, there would be a million things I know need to be fixed.

When, sometimes, you have to take a step back and realize what you already have.

Instead of looking for the "new thing", figure out the thing that's already working, and instead, get better at that. Focus more on that. That's where the real growth is.
April 29th, 2020
Everyone's got ideas.

  • Ideas for businesses
  • Ideas for how the country should be run
  • Ideas for how celebrities should act
  • Ideas for how a movie could be better
  • Ideas for how an artist could have made better music
  • Ideas for how people should live their life
  • Ideas for how relationships work
  • Ideas about God, religion, happiness, meaning of life, etc

If you have ideas, but don't go about sharing and representing them constructively, as well as executing on those ideas, then people won't respect you.

I went to the bookstore the other day and saw like 10 anti-Trump books featured on the shelf. Then, I went on Twitter and saw a bunch of people arguing about the latest politics thing/flavor of the week.

Nobody respects these authors/pundits. Nobody will remember these people.

The ones that will be remembered are the ones that had ideas and actually worked on those ideas their whole life.

I often think about this video on Bernie Sanders. Who cares about politics, left/right, etc - Bernie gets my respect because executed, for decades, mostly quietly. People will remember Bernie.
April 28th, 2020
For May 2020, I'm doing the 500 Challenge.

What is the 500 Challenge? I made it up.

The challenge is to get Pigeon to 500 DAUs (daily active users) by May 31st, 2020.

If I don't reach this goal, I will donate $1 for every DAU I don't have, below 500. Currently, we have about 100 DAUs.

'Daily active users' is what it sounds like: unique people actually using the product every day. It's not signups.

Why am I doing this? It's time to focus on growth. It's time to focus on driving users and retaining & engaging them. More on this throughout the month.

But this is my commitment.
April 27th, 2020
Making money while you sleep... 

I know it's a cliche thing to say - but it still blows my mind every time I think about it.

Today, I took a break from work, and went for a run, and then played video games for an hour.

In that hour:

  • over 300 people visited my website
  • a dozen people joined the newsletter
  • a few dozen people used features of Pigeon
  • a few people visited this blog
  • I made a few bucks

I didn't need to do any (direct) work for any of this. All the work has been done.

The thing is, what blows my mind is not that I "made money" while I wasn't doing anything - it's the fact that my own work, my own creation had some sort of impact on people that I will likely never meet.

This concept is not only about money - it's about being a creator - it's about creating art. Knowing that, while you sleep - someone landed on your website, subscribed to your newsletter, watched your YouTube videos, got inspired by your blog post, donated to your charity, etc - that's what blows my mind.

To laugh often and much; to win the respect of intelligent people and the affection of children; to earn the appreciation of honest critics and endure the betrayal of false friends; to appreciate beauty; to find the best in others; to leave the world a bit better, whether by a healthy child, a garden patch, or a redeemed social condition; to know even one life has breathed easier because you have lived. This is to have succeeded.

- Ralph Waldo Emerson
April 26th, 2020
I officially closed my DMs on Twitter. I also turned off direct messaging on LinkedIn.

It has come to a point where I need to do this. I don't get a million messages, but it feels like pretty much every morning I have a couple DM requests, emails, etc that I have to address.

I need to start taking my own time more seriously.

When I think of "really productive people" I think of Tim Ferriss - this guy is so methodical about how he structures his time. I imagine his own mother goes through his assistant to get to him.

How can you tell a good friend that you don't want to meet their other friend for coffee to chat about startups? Or decline a phone conversation with your friend who has a friend who wants to talk about coding boot camps?

I have to learn to turn these things down - it's easy to do over email - it's really hard to do to someone you love.

I have a college friend who texted me about startup related stuff, and I still haven't responded. It's been like 3 or 4 days now. 

After the "how to say no" project, it's become a lot easier for me to say no, or just ignore people. I don't feel as compelled to respond to everything. I'm really happy I made that project, it changed my life, because, before I made it, I thought I knew "how to say no" but I really didn't!!
April 25th, 2020
One thing I love about coding is how 99.9% of the time, the code is right and I'm wrong.

When I'm debugging something really tough, I have these moments of wanting the bang the computer against the wall, and "I'm 100% sure there is a bug in this library!!!".

Then, I take a step back, rethink things, dig deeper, start reading source code, start reading old Github issues, and then finally I get it.

And most of the time, it's for something really dumb - pure user error.

Today, I had one of those moments - I'm working on push notifications for Pigeon - I couldn't get them to work after trying (what felt like) everything. Then, after over an hour of pure confusion and frustration, I solved it.

Like an idiot, I had "Do Not Disturb" turned on on my computer - that's why I never got any notifications! Haha.
April 24th, 2020
Good week. Got a lot done. Been very focused.

Took some time off of video games during the week, getting too addicted.

However, I did make up for it tonight by playing like 5 hours straight of Zelda Breath of the Wild and finally beating the game. I think it's the best video game I've ever played. It's a perfect game. 10/10. Every time I play I'm in awe. It's so inspiring.
April 23rd, 2020
A couple months ago, I made this prediction.

And I think it's becoming more and more relevant. On sites like Indie Hackers, I continue to see "big success" stories from people selling content, courses, ebooks, etc.

In the next couple of years, I think we will see almost everyone trying to make money on the internet pivot to these kinds of models.

For a few reasons, I think:

  • It's becoming harder and harder to build an app (or more importantly grow an app)
  • Big tech companies are making it harder every day to build anything that "sticks" for consumers. For example, people spend 99% of their digital time using free Facebook and Google products (Instagram, Facebook, Chrome & Gmail)
  • It's very tempting to make "quick money" and once you make this kind of money, I imagine it's hard to not keep doing it over and over. For example, spend one week making a "course" and make $10k or spend 6 months building an app and make $1k..
  • Selling content on the internet has become more "accepted" - 10 years ago YouTubers would get canceled if they monetized their content - now it's weird if you're NOT monetizing

I think that the traditional business & entrepreneurship media has convinced all of us that the idea of "success" is building a "real company" - and it's probably convinced me. For me, if I built a business selling courses, I would not be happy with myself. 

Maybe that changes in the future, but to me, it's not my idea of success and it's not why I originally got interested in tech, learning to code, building products, etc. I'm a millennial, and I grew up on Wikipedia, Napster, Digg.com, Web 2.0 and the early days of YouTube - so my brain has been etched with "information should be free".

But I can see myself sometimes going in that direction with Starter Story... I need to make money and I need to eat, and when I see other people making $XYZ/month, it becomes so tempting to move in that direction.

But I think it's important to remember why I got into this whole thing. It's never been about making money. Sure, I want to be "rich" one day but I don't want that now.

I want to build something with IMPACT, something that changes the world. Maybe what I'm working on now isn't there yet, but I still have at least 40 more years to figure it out.

Some people just want to make passive income and have a nice life. For me, that obviously sounds nice, but I know if/when I get there I won't be happy. I would just start more things and keep trying to level up. 

So, for me, I hope to never need to make money selling my knowledge. Maybe it's because I, deep down, don't believe I have any knowledge that's worth selling. Maybe I will at the end of my life, but not now.

I'm not being self-conscious here. As an entrepreneur, I think you have to fundamentally believe that what you know isn't special. Everything can be learned, and it's usually never learned through a course or a book, it has to be learned by doing or through people you know or have a relationship with - and those things fundamentally cost nothing.
April 22nd, 2020
Today, I released a big new feature for Pigeon. Well, not really a feature, but a pretty big UI change.

I was a bit worried because, technically, this new feature changes the way Pigeon is presented inside Gmail, and it's a bit more "in your face" than it used to be. 

Part of the reason I changed it is because it makes Pigeon easier to use, which is very important. The other reason, is that it by being more "in your face" it will increase engagement and active users. But that's a post for another day...

Anyways... I was nervous about how people would react when I made the change. This made me work really hard on the feature to make it "perfect" and as visually pleasing as possible.

I deployed it and sent the announcement email.

What happened?

Nothing. Nobody complained. I only heard good things and people telling me how much better it was!

Nobody cares! Don't let people stop you from making important changes. And if you do fuck something up, you can always fix it :)
April 21st, 2020
A couple of weeks ago, I was talking about simplifying my todo list and moving to only three tasks/day.

Now, I'm pushing it down even more - to one task per day.

These "tasks" are different, though:

  • They are bigger in scope, they are more like a "project", a new feature, or a new process.
  • These tasks get finished to 100% - I try to solve all of the edge cases and set them up for the future (and so I don't have to touch them again)

These tasks aren't "respond to emails" or "publish new blog post" or "send newsletter". I still do those things, but they are busywork - they need to get done but they aren't a part of my "serious" todo list. They are just the day to day - and I need to keep thinking about ways that I don't have to do those things (through hiring, outsourcing, automating, or simply eliminating).
April 20th, 2020
As a bootstrapped founder, I have a close relationship with customers and people who try out my products.

They have a direct line with me, and when they have issues, they can message me. When they cancel, they tell me why. When they don't like something, they tell me.

One thing I've noticed is there's a specific type of customer that my business is not good serving. It's usually someone who has feedback about design, usability, and features compared to other tools.

Here are some examples:

  • "The setup interface required too many clicks"
  • "It doesn't work like my other tool"
  • "It's not as easy to use as I'd like it to be"
  • "It needs a dark mode"
  • "I will buy your product ONCE you have [INSERT NICHE FEATURE]"
  • "I'd like this to work like a relational database"
  • "I'm a developer, this would be really easy to implement."

Talking to customers and getting feedback is the cornerstone of building a great product, but this kind of feedback (while still valuable) may be a sign that it's not the right customer.

Sure, I can build an interface that requires fewer clicks, but that won't result in new customers, and for 95% of customers, clicking a couple of extra times is fine. It's not 100% ideal, but it gets the job done. The key is that my product solves a serious pain point for them.

When I started out, I took this kind of feedback really seriously, but over time I saw the same trend, customers who had this kind of "nitpicky" feedback tended to cancel anyways. Was it (1) the result of me not having a good enough product? Or (2) them not being the right customer? It's a bit of both, and when you have both, it will never work out, even if you improve things on the product side.

I think a common mistake we make as early founders is that we look at [INSERT BIG COMPANY IN YOUR SPACE] as having a shitty product and that we can easily build something better.

But as we build a company, we realize that:

  1. Better product =/= better design/UI/ease of use (i.e. Salesforce)
  2. Building a great product gets really hard, especially as you grow
  3. Almost all (big) companies have a shitty product

I still believe in building a great product, but as I've gone from software engineer to founder, my idea of a "great product" has started to evolve - and that's where I've had to make some tradeoffs.
April 19th, 2020
move the needle. (idiomatic) To change a situation to a noticeable degree.

  • Changing the layout of your homepage will not move the needle
  • Most new features will not move the needle
  • Switching from X to Y tool/platform will not move the needle
  • Small SEO tweaks will not move the needle
  • A Product Hunt launch will not move the needle
  • Emails will not move the needle
  • "That one big potential customer" will not move the needle
  • Meetings will not move the needle
  • Consultants will not move the needle
  • "That one growth course" will not move the needle
  • Implementing Vue.js will not move the needle
  • Rebuilding your codebase will not move the needle
  • Unit tests will not move the needle
  • Moving off of Heroku will not move the needle
  • "That one blog post" will not move the needle
  • Changing the copy of your call to action will not move the needle

As an early founder, I've found it very dangerous (but also tempting) when I'm prioritizing tasks like these over tasks that actually move the needle.

I'm not saying these things aren't important, but (in my experience) most of them don't have a high impact on the business.
April 18th, 2020
I always listen to music while working + noise-canceling headphones.

My criteria for the most productive music:

  • DJ sets
  • Music with no lyrics (or repetitive lyrics)
  • Classic hip hop albums / mixtapes

The best music is music that "flows" together naturally (like full albums and sets), rather than a playlist on shuffle. When music effortlessly transitions, I get lost in my code/writing/whatever.

I also find YouTube to be the best way to listen to music because they have the full DJ sets and albums, and their recommended is really good.

Here are some playlists/sets that always get me in the zone:


^^ A running list. If you know of other music I might like please send it to me!
April 17th, 2020
Today, I had a customer who was trying out Pigeon.

They had a bug so they messaged me through the app - we got to talking and we couldn't solve the issue. So I offered to jump on a screen share and look into the problem.

We got on screen share and then solved the issue.

Getting to talk to a customer organically like this is awesome, so I asked him why he was checking out Pigeon and what he did for work.

He started talking and telling me why, but for some reason, I got "spooked" - we started talking about competitors but I didn't want to come of like a "sales guy" so I just told him to let me know which product he ends up going with.

I wish I just kept talking, kept selling, kept asking questions about him, but I didn't.

And then, when the call ended, I immediately regretted not doing this. FUCK.

It was like when you see a cute girl, contemplate talking to her, you hesitate, and then it's over - and you think "what if" for the rest of the day...
April 16th, 2020
I've found that removing distractions from my everyday life is a guaranteed way to become a tiny bit happier.

And it sort of boggles my mind that not everybody does this.

You know that notification that you keep getting from XYZ app? Maybe it's iCloud letting you know your phone isn't backed up, or a new "like" on Instagram.

Or maybe it's MyFitnessPal sending you the same message every day.

IMG_4988.png 9.42 MB


Well, here's a guaranteed way to improve your day:

  1. Figure out how to turn that notification off
  2. Live your life for a couple more days
  3. Look back and realize how much better your life is without that thing

An example

I used to get email notifications whenever someone signed up for a free trial to Pigeon.

These notifications "felt" important - probably because they gave me a mini rush of adrenaline.

At best, I could see the email who signed up, and at worst it would put me on a 10-15 minute bullshit sidequest of distraction.

One day, I accidentally removed these notifications because I made changes to how free trials worked.

For the next couple of days, there were people signing up for the product and I had no idea.

But guess what? It didn't matter. Someone signing up to Pigeon does not (and should not) require any attention from me.

This may seem like a simple example, but you can apply it to everything:

  • Turn off Stripe email notifications for when you make a sale
  • Delete Instagram from your phone
  • Mute everyone on Twitter
  • Put on Do not disturb on your phone
  • Put your phone in another room
  • Don't leave Slack open on your computer
  • Unsubscribe from all emails
  • Filter out unimportant transactional emails

The list could go on forever.

From my corporate days

I remember when I started my first job in corporate America, there was this internal chat/IM program called Microsoft Lync (before the days of Slack).

99% of the company would be online ALL THE TIME on this. You could IM anyone in the company and interrupt them, anytime, and it was a big company (300k+ employees across the world).

After I started working there, I found that conversations on Lync tended to go on for way too long, and the majority of conversation was about nothing / complaining about your bosses or clients.

So, I decided to uninstall Lync from my work computer. Life was so much better without it, and I got so much more work done.

However, people at the company thought I was crazy. Everyone asked about it. And because I was never "online", many people thought I was fired.

It still doesn't make sense to me why people wanted this distraction in their lives.

I think that maybe people are just different. Some people enjoy chatting on IM and being distracted and complaining about their boss and generally dilly-dallying through their day... I'm just not one of those people.