December 31st, 2019
At the end of last year, I wrote a blog post called The Best Year Of My Life: In 35 Tweets. I loved writing that post because 2018 was such a crazy year for me.

With that post, I felt like I was coming out to the world about some really big life and career changes (quitting my job, starting my own business, going digital nomad, etc). It was a really exciting time for me.

Fast forward to today - there’s just one day left in 2019, and I feel like I have to write one for 2019.

But 2019 was not “the best year of my life” - maybe I wish it was - so I could write a post that would top last year’s.

2019 was just very different. It was my first year working full time on my own business, setting up the foundation for a (hopefully) prosperous next 20 years as a founder.

This recap probably won’t be as exciting or inspiring as last year’s, but here it goes…


The good:

  • Hit $100K in ARR (yearly revenue)
  • Started building a team and hiring people
  • Started a new, ambitious project
  • Starter Story hit 100K+ Monthly Users
  • Met and worked with Kanye West
  • Ran over 1000 miles

The bad:

  • Digital nomad-ing didn’t work out
  • Got rejected from YC (again)
  • Isolating and depressed at times
  • My new project (Pigeon) has been harder than expected

Going digital nomad

In January, I started the year in Chiang Mai, Thailand.

I was bright-eyed about the idea of being a digital nomad. Everything (food, hotels, etc) was so cheap. I was spending $1,500/month max.

I spent most of my time working from coworking spaces and learning some of the ins and outs of the digital nomad lifestyle (finding apartments, visas, etc).

My $150/month apartment in Chiang Mai, Thailand

In February, I made my way to Bali.

I drank beers on the beach with Pieter Levels, Andrey Azimov, and Marc Kohlbrugge - it was surreal.

I met countless other people I had only known through Twitter and made some amazing friends and relationships.

But I’ll be honest, I sucked at being a “digital nomad”.

I found myself getting pretty depressed. I had this weird dichotomy where I really wanted to travel and experience new things, but I also really wanted (and needed) to work on my business.

So, although I was in these new amazing countries and cities every month, I was pretty much just working all the time.

Looking back, working on my own and not having a job was just so new to me, that I couldn’t comprehend or justify not working. I couldn’t relax.

I worked a lot.

Since I didn’t have a “real job” I lost the concept of normal working hours, and of weekdays, holidays, etc. All the days started morphing together into this crazy blob.

Looking back, I feel like I needed to go through that pain and confusion and learning “how to work”, because nowadays I have a far better sense of how to be productive and feel like I’m in much more control of everything.

Through that trial by fire, I’ve become much more productive with less hours, learned how to outsource and build a team (more on that later), and started running a lot.

A photo I snapped on a run in the rice fields of Ubud, Bali

Killing off all the extra projects

In March, I found myself overwhelmed with the amount of projects I was running.

Fresh off 2018, I had launched multiple 24 hour startups and I was running 4-5 different projects at the time.

It was cool to build and launch so many new things, and it looked great on my Twitter, but it was not realistic, and it did not result in a lot of money, which I need or else I’m back to being a software engineer.

So I decided to make some hard decisions and kill off all my extra projects.

I knew it was time to pick one project and focus nearly all of my energy on it. That was the very early beginnings of what turned into Pigeon (more on that later).

I also sold one of my apps!

Picking up running again

In March I also ran a half marathon at an active volcano in Indonesia.

I really started to get serious about running this year. I ran over 1,000 miles this year! I ran two half marathons, and a full marathon!

Such a hot and humid day. I also met this guy running. He was a cop from Indonesia.

Focused in Vietnam

In April, I got to Vietnam, where I immediately got food poisoning.

The peak of 48 hours of food poisoning.

I spent most of April building and launching my new app Pigeon. I had committed to a small group of customers that it would be ready May 9th. There was so much work to do.

I just remember being really focused in Vietnam. Same routine, nearly every day, for almost two months.

I quit social media (complete cold turkey) for a whole month which was a really fun experience. I quit EVERYTHING - Instagram, Facebook, Linkedin, Reddit, YouTube, everything!

I found myself with so much extra time, and I started reading lots of books! I think I read over 10 books in one month.

My favorites:

  • Digital Minimalism by Cal Newport
  • Can’t Hurt Me by David Goggins
  • Never Split the Difference by Chris Voss
  • The Millionaire Fastlane by MJ Demarco
  • What I Talk About When I Talk About Running
  • Start Small, Stay Small by Rob Walling
  • Principles by Ray Dalio
  • Shoe Dog (Nike memoir)
  • Zero To One

I’m not off social media anymore, but I still don’t have the Instagram or Twitter app installed on my phone. I also muted every single person on Twitter, so I no longer have a feed and I’m pretty out of the loop these days.

I also started a YouTube channel which was really fun. Although I haven’t uploaded in like 6 months (will get back into it in 2020!).

A video I made about how a piece of paper changed my life.

Launched Pigeon!

And on May 9th, I also “officially” launched Pigeon to a small set of early customers.

It was a small, “soft launch”, but it felt like a massive milestone.

Building a team & learning how to manage

I spent most of June hiring and building a team for Starter Story.

While Pigeon was new and fresh, it was taking up a lot of my time, all while Starter Story was (and still is) going really strong.

At this time, I was still doing all of the work myself for Starter Story. I realized the only way to scale (both Starter Story and Pigeon), was to get help.

So I spent most of June hiring and onboarding a small team of freelancers to help run the business.

Nowadays, the Starter Story team consists of 3 (+ me) people who do outreach, review and publish the interviews, manage email, and handle most of the day to day tasks.

It was one of the best decisions I ever made, and I can’t imagine being sane without this team (thank you to Gemma, David, and Ella if you’re reading this!).

Starter Story is now a machine that runs on its own, and I think that’s really cool! We are publishing more content than ever before.

At first, it was hard for me to imagine anyone else being able to do these tasks that seems so “proprietary” to me, but I quickly learned other people could do it, and they could even do it better.

I also learned a lot about how to hire people, manage, and onboard them! This process gets me excited about the future and how I can take myself out of a business once it’s running smoothly. It’s really fun.

10 Paying Customers!

In July, Pigeon hit 10 Paying Customers!
Ending my digital nomad journey

In July, I decided to end my “digital nomad” journey and come back to the USA.

What I thought would be many years traveling the world ended in about 6 months.

For me, I realized that what’s important to me is freedom from a job and to build my own thing. I don’t need to be in Thailand to have that. I can still have that in the United States, but I can also have all the benefits of being around family and friends.

When I realized that, I knew it was time.

What’s beautiful about it all is that I’m still a “digital nomad”, because I can still work from wherever I want.

After coming back to the US, I spent a month in New York with friends, a week in SF, and a week in San Diego too. I also went to Europe for a month!

On my 29th birthday in San Diego, CA


In August, I went on the Indie Hackers podcast, which was a pretty surreal experience because it was the website that inspired everything for me.

I also ran a half marathon in Idaho with my dad and set a PR.


In September, I was featured on The Hustle, a really popular online publication.

Starter Story also hit 100k visitors!

I met Kanye West, I’m never going to fail

In September, I also had a very, very lucky opportunity to work with none other than Kanye West, who is my #1 idol in life.

I got to meet him and help out at his new Wyoming ranch for a week.

And I finally made my way back to New York for a whole month. It was amazing to get back.

Beers in Brooklyn after an 18 mile run


I took the whole month of October off and traveled through France, Spain, and Portugal with my dad.

Wine and cheese with dad in Paris

It was a great trip, and I’m grateful to be able to take this kind of time off and be able to spend it with my parents.

Self guided bike tour in the South of France

Rejected from YC, again!

I applied to YC, just for fun (kind of) for my new app, Pigeon.

After my YC rejection a couple years ago, I never thought I would actually get an interview.

But while traveling in Europe, I woke up to this email:

I spent a couple weeks preparing, doing mock interviews, all that stuff, and found myself extremely stressed out about the whole thing.

It was honestly a really hard time for me. As a solo founder, I had to explain to really, really smart people about how Pigeon is a company that will make hundreds of millions of dollars.

And that was really hard. I didn’t think about those things until I got the interview, so I was scrambling.

I felt like I was “faking it”, acting bigger or smarter than I actually was, and they could probably see that.

I was rejected.

The interview was a really intense experience, but I’m glad I did it. I learned a lot.

I know Pigeon will be big, but it’s going to take time. I was sad for a couple days, then I moved on. Back to building a business.

YC HQ in Mountain View on interview day.


In November, Starter Story crossed 100k uniques and almost 140K visitors!

The newsletter also crossed 10,000! Starter Story continues to grow every month!

Starter Story traffic in November, our biggest month ever

In 2019, we published over 500 interviews, and that is all thanks to the team and the work we’ve done to scale the project.

We also became one of the biggest websites in the world, our Alexa rank reached 30k at one point. A bit of a pointless stat, but it does mean that we are in the top 0.002% of websites in the world. Kind of crazy to think about.


I’ll be honest, December has been a bit tough - mainly because Pigeon hasn’t had the success that I wish it had.

Although we had a solid launch, we suffered some big setbacks like the Google security audit, and experiencing some churn.

When users churn, I take it personally, because I put so much of myself into the product and into the future of the business.

But, I’m getting better at that. I’m trying to focus more on the things I can control and I’ve been feeling really good these last few weeks.

With the Google security audit out of the way, Pigeon is now out of beta and open to the world, and I feel really good about 2020.

Over the year, I’ve definitely gone through a few slumps. I don’t think it’s depression, but I think it’s part of being an entrepreneur and the highs and lows that come with it.

When my business is doing well, I’m on top of the world, but when something bad happens, it can ruin my day. I attach myself to the business, it is a part of my ego.

I’m trying to work on that and be more mindful and detached from the day to day of the business.

If you haven’t noticed, I also went a bit quiet in 2019 in terms of social media and how much I share about my business. I still do monthly updates, I just don’t tweet about them or tell many people.

I went quiet for a couple reasons. I’m trying to stay away from social media because it genuinely makes me feel shittier. I often compare my own success to others success and that always brings me down.

The other reason, to be totally honest, is that I wish I had a better story to tell - I wish there was more growth, success, money to talk about. But that’s life.

I also started writing more and plan to in 2020. About a month ago, I started writing an online daily journal, you can find that here.

Next year

I’m really excited for 2020.

As far as the business side of things, I am confident 2020 will be the breakout year for Pigeon, and Starter Story will continue to grow and scale.

I’m running the LA Marathon in March.

I plan to move to New York City for the summer, I miss that place and want to live there again. So if you’re out there give me a holler.