The Only Life Option is to Make Mistakes

Say you’ve decided you want to try being an entrepreneur. Or that you want to try and make some online passive income.

The next thought that probably enters your mind is “where on earth do I start?”

Where do I start?

The thing that every successful entrepreneur knows is this:

There’s no 100% sure way to figure out what to do.

That’s a new feeling for a lot of people. Our entire lives in school and at work, we’re told very explicitly what we need to do to “succeed”. We’re given instructions for what’s expected of us.

But it turns out, there’s no syllabus for entrepreneurship.

People can show you what’s worked for them. We can talk about best practices and things one should definitely avoid. But no one knows for sure exactly what will work for you.

Which means:

You are going to make mistakes.

You’re going to try new things, and sometimes (most of the time?) they aren’t going to work out perfectly.

But that’s okay. That’s expected.

The trick is to readjust our internal expectations. We’ve been programmed to avoid mistakes at all costs.

For example, if you make a mistake at your job you might get fired.

So when you’re working for someone else you’re probably much less likely to try new things and experiment. You don’t want to make a mistake and they don’t want you to mess up, either.

But entrepreneurship and working for yourself is a completely different animal.

Do you think someone told Steve Jobs or Bill Gates how to make their companies? Or that they just always knew what to do? No way! They worked really hard, experimented, and made tons of mistakes.

And so what can we learn from them?

  1. Their mistakes never broke them. Aka they didn’t bet their entire companies on one project or “big bet”. They took calculated risks so that if, say, an entire project didn’t work out, they could continue working.Apple’s Power Mac G4 Cube is a great example of this. They built this great product that just didn’t sell. There’s lots of speculation as to why (e.g. was it too expensive?) but ultimately that doesn’t matter. Apple had to cancel it. I know for certain it wasn’t Steve’s first mistake, but it was one of his most public mistakes since he had become CEO of Apple.
  2. You cannot learn without making mistakes. More specifically, you can’t start a new company without making some mistakes. They don’t even have to be big! But it’s going to happen. And that’s okay.

Learning New Things

Remember the last time you learned something new (for some of us, myself included, it’s been a long time!). You can pick multiplication tables as a kid, learning to play an instrument, maybe learning a language. Or maybe cooking or some other hobby that you now enjoy.

I speak Spanish, so I’m going to use that as an example.
Have I always known how to speak Spanish? Duh, no. So what happened along the path between knowing nothing (literally being left Mexico and barely knowing how to count to 10), and speaking fluently today?

Of course I studied and practiced every day. And I went out and I talked to people. I tried to force myself to learn.

And what happened? Well, at first it wasn’t pretty. People were very nice, but they’d often treat me like a child (I was actually 19 at the time) because they didn’t understand me at all. And because I spoke so slowly, I often couldn’t get most of thoughts out before I was interrupted.

It was really frustrating.

Over time my daily practice and study helped, and I improved slowly but surely. It was hard to measure the progress day-to-day, but over a few months looking back I could start to notice people treated me differently. They could finally understand me!

All Learning Requires Mistakes

Now, if you went up to someone and asked them “do you think you can learn a new language without making mistakes?” they’d tell you “Of course not.” And obviously they’re right.

Starting a business is just like learning a new language.

The reason we’re often afraid of business mistakes is because, personally and as a culture, we treat learning a language (or playing an instrument, cooking, etc.) differently from starting a business.


It’s mostly because of money. People associate “business mistakes” with losing money.

The classic example is starting a restaurant. You pay a bunch of money to prepare the restaurant, buy food, hire staff, etc., and then if it fails you lose all that investment.

And for some businesses that’s true. Things like restaurants require a lot of upfront money, and so they’re inherently more risky.

But that’s not true about a lot of other businesses. There are tons of opportunities available these days where you can take a calculated risk and try something out, on the cheap, way before you have to spend a lot of money like you would with a restaurant.

My First App

For example my first app cost only $500 to make. Of course $500 isn’t exactly pocket change, but compared to starting a restaurant $500 is a steal!

If I’d tried the app and spent my 500 bucks and it completely failed, I’d have been out 500 dollars. But by taking a calculated risk, that was okay! I knew that if I lost the $500, I’d be okay.

And, even more importantly, at least I tried! Most people are so terrified of the unknown that they won’t even put themselves out there, personally or financially. So I told myself hey, if this goes belly up and you don’t make a dime, at least you tried.

(I have to insert one of my favorite quotes here, by Hellen Keller:

“Security is mostly a superstition. It does not exist in nature, nor do the children of men as a whole experience it. Avoiding danger is no safer in the long run than outright exposure. Life is either a daring adventure, or nothing at all.”)

So I was totally fine with potentially making a small, calculated mistake.

What About You?

You might read $500 and think “whoa, that’s a lot of money”. The good news for you is, fortunately, there’s plenty of businesses that require even less than that.

And maybe you read $500 and thought “oh hey, I can do that. How do I get started?” Which is great!

The most important part is realizing mistakes are part of learning, and that learning is part of starting a business. And, of course, mistakes can be calculated and controlled. There’s no reason whatsoever to bet the farm on something new.

If you can grok that, you’re emotionally ready to start your own business.

How to Judge Presidential Candidates

How can one person possibly have enough info to make a good choice about who to vote for?

The number of topics a president has to be informed in and good at is astonishing:

  • Agriculture
  • Business
  • Military
  • Education
  • Energy
  • Health Services
  • Homeland Security
  • Housing
  • Foreign Policy
  • Transportation
  • Treasury
  • Veterans Affairs
  • Law
  • Technology

To be an expert on any one of those topics would take an entire career of work. A president has a huge staff and cabinet to help, but as individual voters we’re lucky if we deeply know even a few topics.

What makes things worse:

  • The most we get to see of a candidate is a debate or speech
  • What should a president be good at? “Governing”? What the hell does that even mean?

Passing legislation?

LBJ was remarkably good at this, probably the best of the 20th century (FDR had the help of the Depression). But of course that doesn’t mean the policies passed are good policies. And that’s only part of the job, too.

Increasing US popularity around the world?

I think this is generally good, but taken to an extreme would just weaken our relationships abroad.

Following the wishes of constituents?

Initially I thought this was the answer. Best case scenario the elected has a history of doing what his/her electorate asked for. What else can you expect in a republic?

But then I thought of all the lifetime politicians who now take up space in Congress. The people who get reelected term after term probably do this, and arguably they’re a big part of our problem.

Somewhere I once read this great quote:

“Democracy and capitalism are the worst forms of government, except for all the others.”

I don’t have a good answer for this. But it appears no one from the previous few millennia of philosophy does either.

My 3rd Year in the App Store — Highlights and Numbers

April 22, 2015 was my 3-year anniversary in the App Store with my Spanish Bible apps. It’s been a wild 3 years!

(Quick summary for those reading for the first time: I made a Spanish Bible app in 2012 for $500. It did $1,500 in revenue the first month and has grown ever since. You can read my first year review here and my second year review here.)

Overall it was a terrific year.

Notable Events

I Crossed 1 Million Downloads

It happened sometime in January, so we’re way ahead of that now.

Our Peak Gross Ranking in Our Category was 3

#3 Grossing in Books, ahead of DC Comics, The Walking Dead, Disney, and many others

This put us above Disney, DC Comics, Scribd, and other well establish book apps. And remember, this is the US App Store and we have a 100% Spanish app. All the apps we’re beating are in English.

I Was on the Gimlet Media’s podcast Startup

This was the professional highlight of my year. I’ve been a big fan of This American Life for a few years, and Alex Blumberg was always one of my favorite producers.

When he left This American Life to start his own podcast company I was thrilled. And for good reason, because his first podcast, Startup, is amazing.

This is a longer story that needs to be told sometime, but eventually I ended up being interviewed for that show.

You can listen to it above. The whole episode is great (not to mention their other podcasts), but if you’re strapped for time my part starts at 10:54.

I had Exactly 15 Seconds of Internet Fame

Chatting on the Huffington Post’s Morning Show

About a month or so after the Startup episode aired, I woke up to a Facebook post from an old co-worker. Business Insider had written a post about my apps.

I jumped out of bed and quickly scanned the article. It was basically just a summary of what I’d said on the podcast.

But once Business Insider wrote their article, literally thousands(!) of other websites wrote their own summaries.

And then Fox News posted it to their Facebook page (twice), and did a segment about my company on their morning show.

And the Huffington Post asked me to be a guest on their morning show.

It was an intense 48 hours.

But then the weekend came, and by Monday the Internet had moved on, as it always does. Which was totally fine by me. I was happy to go back to working.

Adventures in Europe

You have to see it in person 🙂

I’d wanted to take this trip for a long time. Finally the stars aligned and my wife and I hopped on a plane to Stockholm to see Europe for two months.

I’ll share just one thing about the trip, my single most favorite moment: seeing Michelangelo’s David statue in Florence, Italy.

To be honest, I’d vaguely heard of the statue before arriving to Florence, and if you’d asked me what it looked like I would have had no idea.

I won’t be able to do David justice. It accomplishes everything art hopes to do and more. It is massive and breathtaking, beautiful and subtle. There’s 10 different ways you could tell the story of David and Goliath based on that one statue alone.

If you ever get a chance to see it, I can’t recommend it enough.

We Moved to Austin, Texas

Salt Lake City treated us well but it was time for a change. My wife and I are thrilled to be in a brand new place.

Austin has a great vibe and entrepreneurial scene, at a fraction of the cost of San Francisco or New York. And it’s in a business friendly state, one 3-hour flight from either side of the country. It’s a great place for us.

Sales and Download Numbers for the Year

Total Annual Sales

Best Month — Sales
January — $13,459.06

Worst Month — Sales
May — $6,889.35

Best Day — Sales
January 4 — $2,038.28

Worst Day — Sales
May 9 — $112.23

Best Day — Downloads
January 4–3,733

Worst Day — Downloads
December 24–951

Average Daily Revenue

Best Sales Day, every single week

Worst Sales Day, every single week


Updates Downloaded

“Current Version” Average Rating of our most popular app
4.5 Stars (256 ratings)

“All Versions” Average Rating of our most popular app
4.5 Stars (658 ratings)

Monthly Sales Chart

Sales by month

I’m as surprised as you that this ever grew to be so big. It goes to show that when there is a need in the marketplace and you fill it with a good product, you will reap the rewards!

Here’s to another great year!

How I Got Over 1,000 Subscribers in 50 Days

I launched my newsletter How It Actually Works in January and passed 1,000 subscribers a few weeks ago.

I’ve separated this into 2 parts.

IMO people often create a narrative about being successful without really knowing why something worked.

So to try and avoid that I’m doing this in 2 parts:

  1. Where I got traffic from (objective)
  2. Why I think people signed up (subjective)

This way you can separate what’s real, and what’s just me guessing.

Traffic Sources


The first thing I did was tell all my closest friends and family. This is easy. While this isn’t targeted traffic (i.e. your family has almost zero chance of ever being a paying customer) getting a quick win and seeing the numbers go up feels really good.

Morale & psychology is 80% of the game so don’t downplay this.


The newsletter comes out every Monday morning so I’ve tweeted out a few times on Sunday nights what I’m writing about. This has driven some decent traffic.

I also have some followers/friends with non-trivial numbers of followers who have retweeted me.

This post about Sam Walton

I wrote this originally as part of the newsletter but it got such a positive response I wrote it up for Medium where it now has almost 4,000 claps and over 24,000 views.

It ended up making the front page of Hacker News, /r/entrepreneur, and got seen by a lot of people on Twitter.

You might be thinking “ok that’s great for you but how is that a repeatable strategy?”

And I hear you.

But in the optionality driven internet where you don’t know what’s going to resonate with a huge audience, the strategy should be to grow optionality.

AKA give yourself more chances to get lucky.

You can do this by:

  1. Writing more
  2. Publishing more
  3. Building relationships (no matter the size of someone’s network)

And when you see something is working double down. I saw that people liked it and so posted it everywhere I could think of (various subreddits, etc.)

I even recorded an audio version… not sure what to do with it yet, but it exists. Also considering making a YouTube video of this in the style of CGP Grey.

Indie Hackers

Writing for Indie Hackers is great because I have the same problems as everyone else so it’s relatively “easy” to get into the mindset of this audience. I can almost write for myself as a journal entry and post it here.

You Don’t Need Another Tool got over 2,000 views, and this post about giving up a profitable business has over 4,000 views.

Sign Ups

So that’s what gets people to the page, but why do (I think) people sign up and open my emails?

Dead Simple Signup Page

I use Instapage for my signup page but you’d never know because it’s so simple. It’s all text and loads super fast, and it’s really easy to sign up on mobile too.

Maybe the lack of sophistication hurts? Who knows. My conversion rate is just under 25% right now.

Single Opt in

Since I’m so small I’m not worried about spam signups so this makes sense for now. I also get a text every time a signup comes in and if it’s obviously bogus I just delete it (this has only happened once or twice).

Welcome Videos

In the 1st few weeks I made a 30-second personalize welcome video for almost every person who signed up who I didn’t already know (sorry close friends and family!)

Welcoming Ramit Sethi to How It Actually Works
Welcoming Ramit Sethi to How It Actually Works

This got some great responses and is a fantastic way to be remembered better by people who only know you as a wall of text.

(I plan on doubling down on this in my professional life in general. What is the “normal” way of doing something, and how can I do something just a little bit better to help stand out?)


I got some unsolicited praise a few newsletters in and starting compiling a list. Now you can find almost all of them under the signup form. Social proof is obviously important, and I like having an easy, scrollable list of support.

BTW: most of the testimonials are men because AFAIK almost all my readers are men. If you’re a woman and like How It Actually Works I’d love to add you to my testimonial page!

That’s it. If you’re a reader I’d love to hear your honest feedback!

How NOT to Manage an Employee

When you hire someone as your employee they’re taking a HUGE chance on you.

Think of the literally hundreds or even thousands of other places they could work for. And yet for some lucky reason, they chose YOU.

Even though yes, you’re paying them. And yes, they have to do their job well to keep it, it’s basically a privilege to have people work for you.

That’s what I learned when I hired my first employee, Jennifer.

One month into the job, she quit.

I had tried to take extra special care to make sure I got everything right for her, so the only thing she’d have to worry about was doing her new job well.

The lessons are important because it wasn’t like I didn’t try!

But yet I still made mistakes.

So here’s what I screwed up that we can all learn from.

Mismanaged Expectations

When I interviewed Jennifer I said the job was 20 hours to start but would eventually be full time. The 20 hours was more of a “testing, learn the ropes together” period.

She understood this, but she also mentioned that she liked the 20-hours a week, and, while I didn’t fully realize it at the time, hinted at being okay at staying at 20 hours. She liked the flexibility, and she was recently married and wanted extra time with her husband.

To this end, she’d even recently turned down a full-time job with Yelp.

I was in such a hurry to get her hired that I glossed over this. So when a week into the job I asked if she wanted to come on full-time, she was kind of taken aback and wasn’t ready for it.

Horrible Timing

She also told me in the interview that she had a few vacations and a family reunion already planned for the near future.

Basically she’d work for me for a week, leave for a month, then come back and start work again. This turned out to be around the holidays, which didn’t help.

If I were doing this again, I’d just wait to have her start until after the vacation and holidays.

Pick Up the Freaking Phone

When Jennifer got back from her first trip she emailed me saying she had some concerns. Like an idiot, instead of picking up the phone to talk to her directly, I just emailed her.

She then took 2 days to get back to me. I was trying to be polite and let her take her time, but looking back it wouldn’t have been rude to just call. After all, she was working for me, and those were days when she should have been available.

I was so new that I was trying to be as flexible and easy-going as possible for her.

Mistakes, they happen!

Setup Employee Accounts BEFORE They Start

This one really irks me, because I did 99% of this great. You wouldn’t believe the time and money I spent making sure Jennifer had her email, payroll, and a bunch of other accounts all setup right, ready for her the day she started (Not to mention the legal hassle it is to hire someone remotely in a different state.)

The one thing I did NOT do, was get her a Google Voice number.

This was important because as a virtual assistant she’d be taking and making phone calls for clients.

It was on my todo list, not just something that I’d forgotten. I figured she was fine making phone calls with her cell for the time.

That was a poor decision.

Even if I had the best intentions (I’d happily repay her for any minutes used on her plan) she didn’t know that. I hadn’t communicated to her that I’d reimburse her or that a Google Voice number was on my todo list. So she naturally assumed that’s how it was always going to be.

It was just one more thing to make her feel uneasy and uncertain about. “Why is my boss making me use my own phone for work?”

It was a fair reaction.

Employees, Hiring, Mistakes

You can’t build anything great alone, so it’s super important to learn how to work with, hire, and manage other people.

That said, we also can’t let the fear of making mistakes get in the way of trying news things. You have to push on into the unknown.

I’m glad I did. Jennifer and I are still on good terms, and I learned a ton in the process of working with her.