October 20th, 2020
“It's supposed to be hard. If it were easy, everyone would do it.”

This cliche applies to everything in life, but today, I’m talking about dating apps.

What has your experience been with dating apps? For me, 4 out of 5 people I met on there were losers.


1 - No barrier to entry

There is no barrier to entry to join the app-dating pool. 

Anyone can join these apps. The world is full of losers, so it makes sense they join the apps (everyone wants to find love, right?).

In the real world of dating, there are tons of barriers to entry. In the real world, you need to build up the courage to talk to people you’re attracted to. In the real world, you need to build the social skills to be able to court someone. You need to display confidence, status, and worth. 

That stuff’s not easy to do. It takes years of practice and failure. With an app, you get to skip much of this (which is bad for the long-term).

If it was easy, everyone would do it!

2 - Reactive People

Another point. The typical desirable person on a dating app is usually “reactive”. Because they have so many matches, they can “react” to the algorithm or the matches that come to them. They are less interested in searching for love and being proactive about it. “Why go to the bar when you can swipe Tinder while taking a shit?

They’re satisfied with love being “handed to them”. They’re not go-getters. I want to be with a go-getter

3 - False Sense of Progress

Dating apps also give their users a false sense of “progress”. When I was on the apps, I would match and chat with people and “feel good” about my worthiness as a mate, yet I never left my house! 

This is obviously not real progress. 95% of my matches would actually never turn into a date, and those dates were never with the matches that excited me the most in the beginning.

I’m not saying “dont use dating apps” but rather “use dating apps as a tool”

Dating apps can be helpful to put yourself out there, and I know a few people that have met their life partners on the apps.

But there are other channels to meet people that might be more effective (less time & effort & better results). They might just be a bit scarier to do at first.

Lastly, using the apps is a huge time suck!

Disclosure: I’ve been on dating apps for years. Yes, I’m a loser too.
October 19th, 2020
I didn’t start getting any solid work done today until 1 PM.

Most of my morning was spent texting, catching up, and FaceTiming with friends and family.

You know how it is… One catchup leads to another, and along with a few good long text conversations, your whole morning is a wash and the coffee has worn off!

Usually, I’d feel quite guilty about this, but less so today. 

Each time I felt guilty about not working, I’d remind myself just how much more important the people in my life are than the items on my todo list.

For work, there’s always tomorrow. For people, there might not be.
October 18th, 2020
This weekend I went to Siesta Key, a beach in western Florida. 

The sand is pure white, it’s cool to the touch, and it crumbles like flour. I’ve never seen anything like it.

Americans hate Florida, but this place is pretty nice... Nice people and great weather.

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October 16th, 2020
The key to managing people is giving them ownership.

  • Instead of you planning the project, give it to the newbie.
  • Instead of you writing the code, let them write it.
  • Instead of you running the meeting, let them run it.

Let them get all of the credit. All of the stakes. Let them own it.

Ideally, these tasks are things you know you can do, but are out of their comfort zone.

Once they realize this ownership, they’ll do a fantastic job. 

They won’t feel like they’re being told what to do, which is what all employees hate. They will feel like they have power, and volition, and freedom.

They’ll also feel challenged and fulfilled. That is what people want out of a job. If they don’t feel challenged, they will slack off or leave your company to go be challenged somewhere else.

If they do a bad job, that’s your fault. There’s a glitch in your teaching, or the systems you built. 

In the event that something does goes wrong, you should never say “I’ll just do this myself”. Fix the problem with them, and learn together, along the way, so it never happens again.

By giving ownership, not only will you have a happy, productive team, but you will have less work on your own hands.

Ever met someone that’s on back to back meetings every day and must respond to hundreds of emails? They are actually bad managers! They put everything on themselves, and cannot delegate and give ownership to their team.

A manager’s job is to build more managers. “Teach a man to fish”.

If I look back on the best bosses I had, that’s how they treated me. They trusted me and let me lead. They gave me ownership, and I always ran with it.

I just went on LinkedIn and looked up these old bosses to see where they are at now. They are all now VPs, high-level execs, or started very successful companies.
October 15th, 2020
It takes time to get what you want.

Let me provide a trivial example.

When I moved to NYC in the beginning of the summer, I wanted to pick up tennis.

But I was new to tennis and had nobody to play with…

I searched “tennis club new york city” on Google and it all seemed so complicated

“It costs $100+ to play for just one hour?”

Then I heard about the public courts, and it seemed even more complicated

“How do I wait for a court? I have to wait hours to play? Who will play with me?”

I gave up, for two weeks.

“I guess it isn’t all that realistic to pick up tennis in a city like New York...”

Then I ran into a friend who told me he’d been playing. I asked if he would play with me and he said yes. 

We met up at the court, and while waiting for a court, I met a girl who was also waiting. I set up time to play with her the following week. 

After playing with her a couple times, I met another guy. We started playing weekly.

A couple weeks later, after finishing up a game with him, I saw an old friend’s twin brother waiting for a court. I introduced myself and we started playing weekly.

While all of these random connections were happening, my IRL friends also started to get involved. My roommate got a racket. And then my best friend got a racket. And then his girlfriend got a racket.

I had even more people to play and learn with.

Then, their friends, and friends of friends wanted to get involved, too. So many people that we started to have to play doubles. I continued to meet more friends of friends who wanted to play.

By the end of the summer, I had dozens of tennis partners. Dozens of people I could text anytime and ask to play, or they would text me and ask to play. 

Too many people, actually! I started playing twice a day, 14 times a week! But I loved it.

This is all a silly example, but my takeaway here is it takes time.

In the beginning of the summer, I felt hopeless and didn’t know where to start. But through small, consistent effort, I built this tiny little tennis community and made dozens of friends and ended up with endless opportunities to play tennis.

And that brings me to today...

I’m in Tampa, a new city, and I still want to play tennis regularly. I’m frustrated that I have no one to play with, and finding even one person to play with feels daunting…

But I must remember that it takes time!

I should just focus on finding just one partner, rather than expecting to have what I had in New York. 

Start small. One partner at a time. From there, I will build.

It all starts with something. Want to write? Start with one word, one sentence. Start a business? Start with one simple task.

You don't set out to build a wall. You don't say 'I'm going to build the biggest, baddest, greatest wall that's ever been built. ' You don't start there. You say 'I'm gonna lay this brick as perfectly as a brick can be laid,' and you do that every single day, and soon you have a wall.” - Will Smith
October 14th, 2020
My favorite thing about playing tennis is the anticipation of the opponents’ serve.

Right before he lobs the ball in the air, my mind races. Races with uncertainty. “Whats going to happen? Where’s the ball going to go?” Sometimes, I have thoughts like “I’m going to fuck up and forget how to hit the ball back”.

But every single time, all of those thoughts wash away the moment the ball is barreling towards me.

My mind becomes blank. It goes into instinct mode. My only concern is hitting the ball back, and my body goes into autopilot.

I don’t think, I just “do”.

That’s why I love playing tennis. I become present without even trying. I become present out of necessity.
October 13th, 2020
Today, I met up with a fellow founder friend.

We met in the middle of the “workday”, at 11 am, played tennis for a couple of hours, and got lunch.

We both acknowledged how awesome it is that we have this kind of freedom. 

We don’t have to ask anyone’s permission or request any time off. We just choose what we want to do, right at any moment.

But right after we acknowledged this, we also agreed how much we already take this freedom for granted.

With this freedom, we now stress about how we’re not being productive enough with it. We’re focused on the “next milestone” or that shiny new thing in the distance.

Just a couple of years ago, we dreamed of the idea of owning our schedules, being our own boss, and getting paid to build cool shit.

Now we have it, and it feels so damn normal. 

“Was this all it was really cracked up to be?”
October 12th, 2020
Drake has a series of songs titled 9AM In Dallas, 5AM in Toronto, etc.

Instead of coming up with traditional names for those songs, he likely just wanted to give the listener an idea of where he was at the time of writing...

I’m up early in San Diego, I’m visiting. I’m used to east coast time, so it really feels like 8AM.

The people I’m staying with won’t be up for a couple of hours, so it’s nice to sit here and get my writing done for the day.

Yesterday, we were talking about COVID and how crazy things were just 8 months ago. Back in March in San Diego, they wouldn’t even allow you to go to the beach. Cops were patrolling the beach and kicking people off.

There was so much fear back then. Everyone (people, businesses, governments) were forced to make decisions and take such drastic measures.

I was one of those people who was very filled with fear. “Everyone should lockdown, do nothing for months.”

But nowadays, I actually feel the opposite. I feel that people must move on. 

Not really for economic reasons, but personal reasons. For mental health.

I know a lot of people that “moved home with their parents” during COVID. On paper, moving home sounds like a great idea (save money, spend time with family, etc), but the reality was much worse.

With everyone I talked to, it was not a great experience after 1 or 2 months.

When you move home, you’ll likely lose your social life. Meaning no friends, no parties, no bars & restaurants, no dating, no job/coworkers, etc.

If you think about it, that’s very unhealthy.

I think that maybe we took being social for granted. Humans have a biological need to be social. To meet people, spend time together, laugh together, work together, love together. You take that away, and your brain gets fucked up.

Most people I know that moved home realized this and realized they needed to “get back to real life”.

Many people are making it back to New York City now. They don’t have to move back (still remote) but they are choosing to.

As the people trickle back into New York City and pick up where they left off, they actually seem a bit socially awkward! I think it’s because they spent so much time in isolation! (NYT has a piece on this)

The issue now is that people are ready to get back to normal lives, but they are afraid to announce it.

I know so many people that go on vacation but won’t post anything on social media because travel is still a bit taboo. I also met a girl who told me she doesn’t like it when people post on social media about their wedding because “of all that is going on in America”.

It’ll be interesting to see what happens next. COVID will still go on, but people will (silently) pick their lives back up, I think. I wonder how that will impact social media, and mental health, and politics.
October 9th, 2020
There’s this really neat feature on the iPhone that will auto-create a montage for you from photos and videos in your camera roll.

It will use the location and time and facial recognition technology to make pretty decent videos. It also adds music to it as well.

It’s basically an "automated vlog", which I think is so friggin' cool.

After exploring this feature, it's inspired me to take more videos

More specifically, to take videos of more random stuff in my everyday life. Videos of hanging out with friends, cooking, relaxing, and playing sports.

Taking 4K video is now possible on most iPhones, and these days, you can whip out your phone and film stuff and no one will even notice. It just looks like you're snapping a photo or doing an IG story.

I’ve always wanted to have a vlog, but it's always been too much work to do all of the editing... 

I think that Apple is onto something here, and this technology will get even better. I also thing there is a good business idea here: automated vlogs / video creation / video editing...

Here’s the automated vlog that my iPhone created, from videos I took one day in France. Pretty cool, right?

October 8th, 2020
Today, I’m unfollowing everyone on Twitter.

When I started on Twitter a couple of years ago, it felt like a goldmine of people, connections, value, etc.

It doesn’t feel like that anymore (for me).

When I scroll through my feed, I have very cynical feelings.

I also don’t like the recommendations that Twitter puts in my feed, as well. It pushes up many tweets that make me compare myself to others (business milestones, specifically).

I also want Twitter to be less about status games, like “who follows who”, who liked my shit, etc. I want to use Twitter as more of a place of free expression.

Ethan explained to me the feelings of liberation after doing it:
If I unfollow you, I hope you understand it is only for these reasons.

(I’d be lying if I told you that it didn’t offend me when I got unfollowed, so please know it comes from a good place)

If you unfollow me, I 100% understand.
October 8th, 2020
I realized yesterday that I’m very excited about mental health. 

What caused this? I think it’s COVID! The pandemic is a reset. It has stripped down my life to something that is more bare-bones.

I’ve been talking to Pieter about this, and he said it best:

“Covid dried the lake and now we get to see what's at the bottom.”

If you asked me about mental health last year, I would have said something dismissive, like “mental health is becoming a buzzword”. If you asked me 5 years ago, I might have dismissed it completely.

When you’re 25, especially as a male, you’re so focused on your career that you can mask any mental health issues by burying yourself in your work.

There is nothing wrong with that, but at 30 I’ve got some of that career stuff figured out, and I realize I’m still fucked up in the head… 

So where do I go next? The only place I can go is internal. It’s scary as fuck but it’s the only option!


My 25-year-old self had a lot less empathy for mental health.

My mom (a therapist) once told me that when guys get older, they can lose some of their ambition. 

When I heard this, I couldn’t wrap my head around not being ambitious.

But now I realize how naive and unempathetic I was. This naivety might have caused pain with my friends and family, and regret that.

When people opened up to me about their mental health issues, my first reaction was to offer a solution. I would often “advice” people on how to fix their mental health problems.

And after I gave them this advice, and they came back a few weeks later without making progress, I would think:

“Why didn’t you take my advice from last time? You didn’t listen! Why are we going over this again??”

Ugh! What a fucking asshole I was!! 

I did this because (1) I couldn’t empathize and (2) I was ignorant of facts and research (e.g. depression is a chemical imbalance in the brain).

I try to keep this in mind now, and just let people vent.

Venting leads to learning, and it’s not fair for you to cut people off when they are venting, because it prevents learning!

People vent in different ways. Some people vent to their loved ones. Some people vent at the gym. How unfair would it be to end someone’s workout halfway through?

I vent internally, like through this blog you’re reading right now. By venting through writing, I’ve been able to work on many of my mental health issues.

When I post a particularly vulnerable thing on here, I can’t stand it when people send me emails with unsolicited/unconstructive advice! 

“Don’t you know I’m just venting?”

I’d rather you tell me you read it / related to it / are here for me / or have some good constructive feedback. That’s what actually makes me stronger and keeps me going.

Now I realize I used to be “that guy”, but IRL, to my closest friends and family...
October 7th, 2020
Question from a reader:
I think you have a very healthy outlook, believing there are “too many opportunities”. You are probably very optimistic about the future, which is one of the most important things in building a business.

Truth is, most people believe there are “no more opportunities” / “everything has already been done”. 

Most people believe this only out of ignorance. They haven’t spent the time to dig a little deeper and see just how much opportunity there really is out there. There are still millions of successful businesses that haven’t been done yet.

So I think you’re many steps ahead of the game just by having this mindset.

When I first started out, I started a million projects and failed at all but one of them. 

Anyone who’s smart and experienced will tell you to only work on one thing.

That’s the right advice, but it’s also very hard to follow as a founder. At least it was for me. I went against this advice for years.

My advice: learn this the hard way. Start lots of projects. Overwhelm yourself. Understand the pain of running multiple businesses and not being able to focus on one. 

Once you make those mistakes, you won’t make them again. Right now you have so much energy that you can probably do this and still be successful.

You’ll learn so much in the process. I think you’ll learn and grow more than if you just stuck to one single project. Keep going!
October 6th, 2020
A couple months ago, I wrote about finding the truth through writing. The main gist:

The fastest way to transform yourself is to become obsessed with the truth

The faster we can uncover the truth, the more we can accomplish. This goes for everything in life: business, relationships, sports, hobbies, skills, and personal happiness.

As I’ve gotten older, I’ve gotten faster at identifying the truth.

This has helped me loads as an entrepreneur. I’d argue that truth-seeking is the greatest skill an entrepreneur can have. It allows you to solve problems and move quickly.

When my business isn’t working, I can fix it when I seek the truth as to why it’s not working, which gives me the answer on how to fix it.

I’d like to get faster at solving the truth, though. How can I do this?

What prevents me from solving the truth? Ego, beliefs, and wanting to be 'right'.

When I fall back on my ego, I’ll run in circles. I’ll beat around the bush. I won’t make progress.

But in the end, I’ll always land on the truth. The only thing I can change is how long it takes...

I can find the truth in 10 minutes, or I can find it in 10 years.

It’s my choice to spend 10 minutes or spend 10 years. That is completely in my control. Which one do I pick?

If I choose 10 years, that’s 10 years of pain, of wasted time, of not being true to myself. If I choose 10 minutes, I’ve done the right thing.

If I can solve one truth in 10 minutes, I can solve 144 truths in one day. That’s 52K truths in a year, and 525K truths in 10 years.

Compare that with 1 truth solved in 10 years.

This is just an example, but the point is still there. Seeking the truth is progress. It’s growth.

I found this amazing tweet today (the reply):

October 5th, 2020
“Have you thought about starting a podcast?”

If I had a nickel for every time someone asked me this over the years, I’d probably have around $10.

Is starting a podcast a good idea? Probably.

But a good idea is not enough. Good ideas are a dime a dozen.

There’s a famous Steve Jobs quote about focus:

“[It’s not about] saying ‘yes’ but learning to turn down the smart, interesting work that takes people away from their most important priorities. Focus means saying no to the hundred other good ideas.” - Steve Jobs

So when I think about starting a podcast, I think: 

Is starting a podcast the best use of my time and will it yield the greatest results with the least amount of effort?

The answer is no.

If you’re building a business, you probably have friends / colleagues / investors / employees / people-on-podcasts giving you advice about some interesting new "good idea" that could work for your business.

99% of the time, the answer to these ends up being no. The better, more realistic answer is: “someday”:

“Someday we’ll do that, but right now we’re heads down and focused on our current plan.”

Often times, it’s easy to say no. That’s fine. But where it gets hard is saying no to the things you really want to do. Or saying no to things that are clouded in vanity, ego, and looking good for others.

Saying no (to stay focused) is the key to success in business.

“The difference between successful people and really successful people is that really successful people say no to almost everything.” - Warren Buffet
October 4th, 2020
Traffic: I’m most excited about our growth in traffic. Last month we saw 156K uniques, a 29% increase over the previous month (which was already our biggest month ever).

(again, this is a GA data, according to our other analytics tool, we had 312k visitors!!)

To show you this growth (especially in the latter part of the month):

We are seeing massive growth in SEO, hitting over 200k impressions in Google search results per day, a 100% increase over just one month ago:

This is thanks to all the work we’ve been doing with new content over the last few months, and how we are approaching “content experiments”. 

One of these experiments has done so well that it’s bringing in over 2,000 visitors/day to the site! Here’s the growth for those posts in particular:

Going forward, we will continue to take this approach: Finding content opportunities through experiments and then doubling down on them (if they work).

This growth is very exciting because it has opened up ideas for so much more content that we can scale with. Here are some more things we are currently experimenting with:

  • Calculator posts
  • Templates/downloads posts
  • Business formation content (LLC)
  • State-specific content
  • Lists of quotes
  • Slogan ideas / generator
  • Pros & cons of starting XYZ business

Revenue: Last month, we crossed $15K in recognized revenue, our biggest month ever, and a 21% increase over the previous month!

Gross revenue was $12.7K. Unfortunately, we were down again in net new signups for the subscription. MRR for our subscription is $3.9K.

We switched back to more “lifetime” deals for the membership (rather than first-year discounts) and we believe these perform better.

Email list: Last month saw 3K net new email subscribers and the email list is at 25.3K. This month, we hope to optimize email collection more so that number might go up.

Content: We had a goal for 240 new pieces of content, but only published 174, a 12% decline over last month. Although we didn’t hit our goal, we spent a lot of our time coming up with new content ideas, which should be followed by lots of published content.

September Numbers

- Monthly revenue (accrual): $15,398 (+21%)
- Traffic: 156k unique users (+29%)
- Content published: +174 (-12%)
- New email subscribers (net): +3,000 (+11%)
- Email collection rate: 2.40% (-9%)



In October, we will come up with and ship several new content ideas.

For example, we will ship something like “26 Most Inspiring Warren Buffett Quotes”. While this content is simple, it adds “people” to our database. Everyone has people that inspired them to start a business, we’ll soon have structured data on this, such as “Pat Walls Was Inspired By These 14 Entrepreneurs” or “Warren Buffett Inspired These 48 Entrpreneurs”.

^^ This is a simple example, but it’s a part of our strategy of a data-driven content approach, and growing our database to be the “Crunchbase/Investopedia of entrepreneurship”.

Another goal for October is to build streamlined backend dashboards that our freelancers will use to easily add more data to our database and generate content on the fly. Will have screenshots for next month’s report.

One last goal for the month is to increase our email conversion rate.


We are continuing to push towards our goal of 500k monthly uniques by the end of the year.

Every day, it feels like the opportunity gets bigger! We are just barely scratching the surface on how big Starter Story can be.

And I’m not even talking about the opportunity with other media such as video or podcasts. The opportunity is written content, and it’s where we plan to double down.

The question is not how big can we get, but how fast we can get there. We need to focus on building systems, hiring, vision, delegation.

How can we scale this thing without hiring a million people and a huge burn rate? How can we make this operation 10x bigger through code, automation, and systems?

It’s a unique approach, but I believe it will work. That’s what I’m thinking about now, although I have a lot to learn. If anyone has any suggestions, please send my way.

Thanks for reading! (past monthly updates)
October 3rd, 2020

This post is purposefully rough and unedited because lately I’ve felt a lot of “expectations” from this blog, and feeling pressure to deliver amazing posts with “big takeaways” every day, but that's never what I intended for this blog...

As I said in my very first blog post:

I'd like to write every day, and I plan to make that a commitment going forward. It doesn't matter how long it is - I want to treat this more like a diary. 

I can literally type two sentences, or I can write 3000 words, or I can record a YouTube video, or even a tweet. Maybe, it will often just be updates on what I worked on that day, really boring stuff :)


I think I might be burnt out.

The last few weeks have been a drag. I can’t get myself to work on much.

I’ll start my day with ambitious goals and todos, and then it will devolve into scrolling Twitter, writing this blog, and chatting with friends.

As I write this right now, I just have such a mental “fog”. I don’t feel that “energy” which I’ve often felt helped me work so hard over the past years...

I’m not interested in the idea of starting new projects. 

Responding to basic emails and DMs feels like pulling my own teeth out…

Pieter thinks it’s “coronapression”, but I’m not so sure. I’m in NYC and surrounded by people and there’s a lot going on here…

After this post, I had a few other founders reach out to me and tell me they are going through something similar.

When the pandemic started in March, I put my head down and told myself I was going to work my ass off. I did that and it kind of worked. But now we are like 7 months into the lockdown and it’s still very bad. Still so much uncertainty about everything… 

But I also went through a similar burnout patch in May. I did my think week and things got so much better. Is it normal to have burnout twice in one year? I don’t think I’ve ever had burnout before 2020…?

I know what I need to do to grow my business to whatever I want it to be. I just need to do XYZ and I can get there. But lately, it seems like I don’t even want it? If I did want it, I would be doing XYZ with motivation and volition.

This makes me sad because it seems to go against what it means to be an entrepreneur… to be successful at all costs. There are some opportunities I could take that could make me very successful, yet I don’t feel like taking them on.

So what’s exciting to me lately? Not much. I really like playing tennis. I really like this writing stuff, but even that has felt like a drag as of late…

I’m not sure if “taking time off” is going to solve my problem because, to be honest, I’m not even working that many hours lately. My life has been balanced. Also, I took some time off in May for the think week, and it seemed to work for a couple months, but here we are again..

I think I need to just keep talking and writing through it.

I know that moments and phases like these always lead to breakthroughs for me. Better to embrace it than run away from it.
October 2nd, 2020
Social media followers are the result of putting your best work into the world.

How to grow your social media:

  • Step 1: Put your best work into the world
  • Step 2: Receive followers on social media

Most people skip over Step 1. Why? Because they value followers more than they value creating their best work.

They optimize for “hacks” to grow their following, like: 

  • posting woke-isms / jumping on trends (virtue signaling-type tweets)
  • sparking controversy (e.g. cancel culture)
  • Posting sexual images (Instagram influencers)

Where it goes wrong is when they start to focus more on these “hacks” than on the original work they wanted to share on social media in the first place.

It’s easy to find these people. Just log onto social media! They post every day, if not multiple times per day. 

Examine their posts. Are they sharing their own work in a humble manner? Or talking about others’s work? Criticizing? Ridiculing? Trying to sell you something?

For these people, social media is their work.

These people might have followers today, but they will be forgotten tomorrow. Because people aren’t following them for them.

If you create your own work, people will find you and follow you for it. 

Create your own music. Write your own jokes. Build your own business.

That’s the real long-term growth strategy. Kendrick Lamar has only tweeted once in 2020 and has 12M followers. He has this following because he created amazing music, not because he kept everyone updated on how he feels on Twitter.
October 1st, 2020
I remember reading Tim Ferris’s advice on how to write successfully. He said something like this:

“Instead of writing for a wide audience, write your book/blog for one specific person.”

For me, I think that person is an engineer or creative type who’s hoping to start their own business or has already gotten started. They might also be in a job or doing work that they know they won’t be doing for the rest of their life.

^^ (this was me at one point)

When I’m writing, I try to think about this person and how my words will make them feel, and how my words can help them, inspire them, and change their mind.

If you read this blog, I’d love to hear. Where are you at? Got any questions for me? Are there any topics you’d like me to touch on? Email me directly, anything goes :) 

I will try to answer your questions on here, too, anonymously of course.
September 30th, 2020
Two days ago, I went to a fancy restaurant in a t-shirt and running shoes.

I didn’t do this in a cool, counter-culture way either, I did this because I don’t travel with a nice button-down or fancy shoes, and it was too last minute to borrow/buy one.

I felt embarrassed. It made me ask the question that I ask myself almost every day: 

“Am I too old for this?”

“Am I too old to be working on apps? Am I too old to be traveling? Should I settle down in one city? Should I own a car, a watch, fancy clothes, a Peloton, an Equinox membership? Should I get a dog? Should I just go get a ‘real’ job?”

If you’re also an entrepreneur, you'd probably tell me I'm talking crazy.

But to most “normal” people, I probably look like a "lost teen"

What’s a “lost teen"? It’s someone who hasn’t figured out what they want to do in life, wandering around, not making progress, and wasting time.

This is a constant struggle for me. It’s so hard to explain to people what I do. Some of my closest friends still have no idea that I’m even making money. They still think I quit my job to work on a stupid blog…

A Story

A few months ago, when I was back home, I ran into the “popular girl” from my high school.

Her: “Omg Pat I haven’t seen you in 10 years. What are you up to!?!?”

I was with my sister, and she jokingly told her that I still live at home and I’m not employed, which at the time, was technically true.

While I laughed, my high school instincts kicked into high gear. I wanted to blurt out that I actually run my own successful company. I wanted the popular girl to respect me.

But I didn’t blurt it out. I didn’t need to prove that to her. I just kindly asked her what she’s up to, and she went on for about 20 minutes about how she’s getting her real estate license.

In that moment, I was afraid that she would view me as a lost teen. I was afraid she’d think that I didn’t make any progress since high school. Since I was never cool in high school, I wanted the cool girl to not think of me as a loser.

But the reality is, she doesn’t care. 10 minutes after our interaction, she probably forgot all about me. I likely never crossed her mind again. My fears of being viewed as a lost teen are only in my own head.

Embrace Your Lost Teen

I have to remember that being a lost teen is what leads to success, in all cases.

If I didn’t act like a lost teen, I wouldn’t have started a rap group in high school. I wouldn’t have moved across the country to California at 17. I wouldn’t have done the coding boot camp. I wouldn’t have traveled the world. I wouldn’t have started a company.

In my 20s, it was socially acceptable to act like a lost teen. But in my 30s, it’s getting a lot harder. I need to push back on this narrative even more now.

Anthony Bourdain didn’t succeed until he was 46. Bourdain is the epitome of a lost teen: He traveled the world for a living, yet, he’s also one of the most respected people of our generation.

My dad is also a lost teen. He lives in Wyoming and does yoga every day. He only owns one pair for $30 jeans. He started multiple businesses in his 50s and 60s.

I have to push back on the narrative of having things all figured out by 35. If I’m still a lost teen at 64, I’ll have won the game of life.

So let’s wear our $10 t-shirts with pride, because that’s exactly what these lost teen billionaires are doing:

September 28th, 2020
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