May 29th, 2020
Over the next few days, I’ll be writing more about my think week, and some of the things I thought deeply about. Here are some.

Does time == money?

Much of the guru advice out there is about maximizing your time, maximizing your day, and being the most productive person you can be.

Productivity is an addiction - it feels amazing - it’s something we all chase - certainly something I’ve chased in every job, startup, and project I’ve worked on.

We all want to be more productive.

For example, if you’re a full-time software engineer, what is an example of a good, productive day? 

“Being able to code for 6 hours straight, uninterrupted.”

After you code for 6 hours straight, you feel like a boss, like you conquered the day.

However, 99% of the time, I believe this is unproductive.

The only way that would be productive is if you knew with 100% certainty you were working on the right thing, with the exact right specs. We all know this is almost never true.

Unless you’re a software engineer at Facebook working on scaling emojis, those 6 hours were likely an utter waste of human energy.

How much of our work/code that we've written is still being used today? Maybe 10% (for me).

So, are you sure you’re working on the right thing?

You might be 80% sure, but that’s not enough.

To be successful, you need to be able to (1) become self-aware of this and (2) learn to ask the right questions:

  • Are we working on the right thing?
  • If we don't know, how can we quickly test that we are working on the right thing?
  • How can we do this 80% cheaper and faster?

Even if it’s not in your job title, asking these questions makes you a better human and will lead you to more success and happiness in life, in your career and personal life.

Chasing the feelings of productivity is selfish, and it’s something I’ve suffered from a lot. 

As a programmer, I hated meetings and being interrupted. But looking back, those meetings were far more valuable than I knew at the time. 

I wish I was more proactive about bringing these questions up, because often, nobody even asks them.

As entrepreneurs, it is our duty (and a pre-requisite of success) to constantly ask these questions

Asking these questions leads to running experiments and evolution in your business - if your business doesn't evolve it will die.

When you stop asking these questions, you become comfortable - which is the most dangerous place to be if you’re running a company.

Time does not equal money, it’s far more valuable. But it’s less about how you spend your time, and more about how you take back your time. 

Don’t maximize your day, maximize your decade.
May 28th, 2020
I just finished watching True Detective again - one of my favorite shows.

Starting a business, or rather being an entrepreneur, is like being a good detective (in the movies).

To crack the case, you must have an open mind, and you can't go into it wanting to be "right".

Your own personal bias and "gut feeling" can lead you down the long road, but it is also really important.

I think that goes for anything in life, being a great politician, lawyer, doctor, etc.

It's not about being right, it's about cracking the case and serving justice.

Being right is ego - and ego will limit us from being the best at anything in life.
May 27th, 2020
I took almost two weeks off.

Two Thursdays ago, I just got in my car and drove.

I started in SLC and drove to a new town every day.

Every morning when I woke up, I went on my computer and picked a new city, and a new hotel.

I spent most of my time driving, which led to a lot of thinking, and a lot of new ideas and what's planned for my future.

I plan to write more about this, but I just wanted to write a short thing and announce that the daily journal is back.

And if you're someone considering taking some time off, please please please do it - more to come.

My route in 10 days

May 22nd, 2020
Approaching the last couple days of my think week.

Going to go offline for the remaining few.

Last night I had to fix an urgent issue for a customer, which led to checking email, Twitter, and a myriad of other things.

I want to end this time off on a good note, so I'll be going fully offline for the next couple days.

I just wanted to write this so I can mentally commit to that.
May 21st, 2020
I'm now a full week into my think week.

The first couple days were weird, had a lot of anxiety and wondering what I'm doing with my life.

After 3 days in, I had a lot of "aha" moments. Fueled with energy and excitement about the future.

Now, I've hit a bit of a downturn. A lot of boredom, not so much energy, and a bit of sadness.

When I started this, I wanted to read 1000 books and watch classic movies. But what I usually do is watch YouTube and Netflix and sneak in some Twitter.

I wish I was the type of person that could get "lost in books", but I can't.

The important thing though, I am not doing any work, and I am not checking email, at all.

I haven't pushed any code, or looked at my codebase for over a week now, other than to fix one super urgent bug that a paying customer had.

I thought about checking my email this morning, but decided against it.

I know I have some stuff in there that will feel really urgent and stressful.

I have some things in place so that if there is something super-crazy urgent, I will be notified and I can take action.

When I checked my email on Tuesday, it turned into an extra 1.5 hours of work.

Now that I'm in the boredom stage of my think week, I'm antsy to get back. But a part of this feels like I'm not ready yet, like, I don't feel like I really know what I'll work on when I get back.

One thing I do is create "master plans" - for this think week, I'm making a concerted effort NOT to make a "master plan" for when I get back.

These "master plans" never work because they are rooted in hypotheticals and things you might be influenced by in books/podcasts/what you heard from someone else. Right now, I'm driving around the United States - any plan/ideas that I come up with are probably not going to work.

The only thing that is going to work is if I can come back to work with a new mindset and way of thinking that I didn't have before - a new way to approach every day that helps work become more exciting and where I can get out of bed in the morning feeling like I did in the early days of starting my own side project. I miss that.

Change is the only constant. I have to change myself, my outlook, my ideas, etc if I want to move forward faster and with more excitement.

Sitting around and doing "more of the same" does not invoke change and it does not lead to happiness for me.

If there's one thing that is true about the last 29 years of my life - it's that I've constantly changed and adapted for the better.

When challenges were presented to me, I rose to the challenge - this always led to overall happiness and fulfillment.

There are other times when I didn't rise to the challenge - and I regret those moments. I only regret them because, eventually, I rose to the challenge, but it took longer.

Because, for me, I'm the type of person that eventually has to get over those challenges - I can't live with myself if I don't.

The part that I struggle with is when it takes weeks/months/years/decades to actually accomplish these things, when I know it could have been shorter.

I'm reading a book right now about startups. One of the main themes is that failing at a startup should not be about the learning experience.

The more important thing is to have those learning experiences happen at the fastest velocity possible. 

So, in other words, fail fast. Ask yourself how you can fail as fast as possible. Look deeper into why it's taking 6 months / 1 year / 3 years to fail at one idea, when you could fail at 10 ideas in that same time frame.

Because anything else is just wasted time. We can make the excuses that "we learned something" and that makes us feel like "we're OK with failure" which is, definitely, a good thing and par for the course on your first startup try.

But failing like that is "failing blindly" - if someone asks you why you failed, your answer will be rooted in hypotheticals and blurry logic. There are ways to fail faster with clear understanding (based on numbers, talking to real people, etc) - and I think the hurdle between failing blindly and this is our ego and our fear of failure.
May 18th, 2020
One thing that's holding me back is my stubbornness and my unwillingness to "compromise my vision".

Maybe other entrepreneurs can relate to this, but I'm afraid that changes I make to my product / strategy / customers will lead me to build something that strays far away from my "vision".

I'm scared of that because I don't want to build a business that I "hate".

I'm scared of becoming that founder who's (years later) depressed, and slogging away at a business that he/she never intended to build.

So, to prevent that, I think I take actions (or inaction) that negatively impact the success of my business as a potential sacrifice for my happiness later.

I think that, in a lot of ways, this is a good thing. All founders must make sacrifices like this.

But I think this logic is flawed.

The worry should never be about the "vision" - because the "vision" has nothing to do with the implementation.

If your vision is to revolutionize the hotel industry, then don't worry about how you will do that. You might have an idea, but is it good? You can't decide that. Only the market can.

Test that idea, and then change it - test more ideas. You're still following your "vision" of revolutionizing the hotel industry, but you're just finding a better way to do it.

As I learn more about being an entrepreneur, I think a lot about this.

When I look back on some of the reasons why I wanted to start my own business:

- to build cool things, 
- to create something out of nothing, of my own,
- to get fame, status & make money, 
- to own my time & freedom

I'm starting to realize that the road to success has little to do with those things. Those things are more of the "outcome" - they are just some of the awesome things that might happen if you are successful.

If you let the "how" (your ego and preconceived notions) get in the way of the "what" (the vision), then it might break your business and/or cause you to burn out.

I'm the biggest offender of this, and it's what is causing me (and my business) pain.

Picking the most effective "how" is the job of the entrepreneur. I think that's probably how VC's and investors judge entrepreneurs. Not on their idea, but on their ability to identify the best "how".

"My way" (or "your way") might be a good place to start, but it won't be where I will end - if I want to make a bigger change than myself.

But it is also important to balance this. The flip side of this is the greedy entrepreneur that starts with a good business and eventually develops a pyramid scheme.

That's where the vision comes in. Don't compromise the vision, but be ego-less when it comes to how you accomplish that vision.
May 17th, 2020
I just got off of the phone with my mom.

She's going to buy a house - and was pretty serious about it over the last few days.

She sent my family a text today about how she won't be moving forward with that house, for a bunch of reasons that seemed trivial.

I'm pretty sure I know the real reason why she didn't want to buy the house - because she didn't love the house. But once she got further into the process of making an offer, it probably got harder for her to say that.

I just know my mom really well and this is a thing she does - she probably didn't want to let down the realtor, or the seller, or whatever. But it doesn't matter, that's not the point of the story.

After I hung up the phone (just now), I realized I did this thing that I always do - I had to be right about my theory. I had to try and "get it out of her" that she didn't really love it, and that she would have made it work if she really loved the house.

Every time I do this I feel horrible. What does it matter if I'm right? Especially in this scenario.

But why do I do this? I think it's because I'm self-concious because I do the same thing as my mom (in some other aspect of my life).

I make up excuses that dodge the root of the problem, maybe in business, maybe in my relationships.

Making up excuses not to do something is a weakness, and when I see other people do it, I want to call them out on it. But deep down, I only see this as a weakness in others because I suffer from it the worst.

If I didn't suffer from it - I probably wouldn't care / it probably wouldn't have even crossed my mind.

I have a friend who often talks about his brother and how he's unhappy because he didn't take enough risks after college (finding the right career, etc). The reality is... my friend is so critical of his brother because he's actually self-conscious about his own adversity to risk.

He admits this though, and I think that's the most important part.

Sometimes we don't care about being right - but I think that usually means we're just indifferent, or we've "solved" that area of our own life.

For me, a good example is diet. I don't eat much meat, but I also don't care if you eat a steak in front of me. And I'm never going to argue with anyone about the benefits of a vegetarian diet. I just know that's what I like.

I do know people that will argue/talk for hours about being vegan, or why you should only eat meat, etc. The question I think about is "why do they care so much to impose their own personal choices on others?". 

For people like this, there's something deeper that causes them to be this way. 

Why do they have to be right?

I don't want to be right anymore. 

For the things I'm fiery passionate about, I don't want you to think I that I'm trying to be right. Because when I do this, I just look like an asshole.

You can't change people. You can only change yourself.

If I can let go of this, my life will be 100x better. Working on it.
May 16th, 2020
It took 3 days, but now I’m starting to get some clarity.

I need to extend this time off for another week, I think. Keep driving, keep thinking.

What is the root of this burnout? When people ask, I say a lot of things to make excuses for myself.

But the root is in my new business that's not doing very well.

It has been really hard.

I think it’s been hard for a number of reasons:

  1. My previous business success was a lot of luck - I got lucky in a few ways
  2. The previous business had a much lower level of difficulty
  3. I’m getting stuck in my own way - my own vision and ego are harming both businesses

How to fix this?

The first thing I want to say is that I won’t be giving up. 

I won’t be giving up because:

  1. I have had some success with all this. It’s not a complete failure.
  2. Starting over is a crutch. I can switch and change things without starting over, and save time in the long run.
  3. I’m still obsessed with the problems I’m trying to solve.

I just need a better framework to make decisions and change these things.

It's especially hard as a solo founder. Instead of having someone to bounce these things off of - you must go internally & look inside to make change.

This can be a good thing because you can make change without friction (w/o fighting with your cofounder). But this can be a bad thing if you simply never change.

And I won't change unless I can become more self-aware, more open to feedback, and most importantly, letting go of my ego.

Instead of thinking “this is how it will be in 5 years”, think about “how can I find the right customers, talk to them, and get more feedback and change and tweak things”.

How do I build a framework for this?

I already have a baseline. Starter Story - it’s a massive benefit. Income coming in every month, lots of users, and a platform to work and try and experiment on new things.

Just like DHH and Jason Fried at Basecamp - they have a successful product and personal following and ways of thinking - but they constantly are evolving and releasing (and often failing) at many products.

I need to be more on the ground floor, open to feedback, and finding the right customers.

I need a framework.

Been watching some videos on “The Lean Startup” - and I really like some of the ideas there. The “Build, Measure, Learn” idea as well the “pivot or persevere” idea.

What I need is to dig deeper there and actually try out these frameworks - to be more on the ground floor. I did this early days with Pigeon and actually made a ton of progress - but as of late I haven’t.

More to come.
May 15th, 2020
What do I want out of life?

I’m 29 years old. I haven’t figured out what I want to do with my life.

I don’t have a “thing” that I’m passionate about. I want to have a mission in life, a North Star, something that can drive me.

I’ve been watching “The Last Dance” (great show highly recommend), and for Michael Jordan it was basketball and winning championships.

What is it for me? 

I feel like I’ve been stuck in this place, for years, where I don’t know what I want out of life.

It’s always changing. One year I want one thing. The next year I want another. Music, college, a degree, corporate, engineer, starting a company.

There are some things that I want out of life, for sure, like freedom and autonomy. But it doesn’t feel specific enough.

I know that I want to create - but I can’t really be sure about much more than that.

But I think that’s OK. It’s never so black and white.

I don’t think that I can be so specific. Only in the end will I know what it is that I accomplished.
May 14th, 2020
I'm starting my think week early.

Need to just take a break and get out.

I just drove four hours away from Salt Lake City, to a remote town in Utah.

I'm staying in a hotel, by myself.

No work, no email. Just thinking, and reading, and watching old movies that I torrented.

I'm not sure where I'll go tomorrow, but I'm thinking I'll go to the Grand Canyon. It's about 6 hours away.
May 13th, 2020
Too much of a funk.

Taking the weekend off. Off from all internet, work, email, everything.

Planning on doing a "think weekend".

Inspired by this.

Will report back soon. I will probably still write on here.
May 12th, 2020
If you've been reading my posts lately I've been in a funk.

I chatted with Harry Dry today a bit about the situation.

Maybe I need to do more "fun things" - more side projects, more YouTube videos, more personal stuff.

But at the same time, when I do those things, it feels like a disservice to my customers, the people that work for me, and to myself.

One thing that Harry reminded me is that I have this thing right now called time.

When I had my full-time job and was grinding on Starter Story, all I wanted was to own my own time.

Now I own my own time. I don't have a boss. I can do anything I want.

Yet, I'm taking that for granted now.

I have to remember all of the work that got me here. I don't have a fucking 9 to 5 job!

Now that I own my time, am I becoming lazy? Or maybe being lazy is the "next step" when you own your own time? 

Maybe being lazy and having less to do is what is supposed to happen?

But I don't want to be lazy. I want to achieve big things. So much more that I want to do.

Maybe I'm becoming complacent? I don't want to be complacent.

Harry had a great idea. Take a full day off. Recharge completely.

Do more of the things I "love" - or learn to "love" the things I don't, yet.

It's unlike me to ever feel this way - so I think it might be a fluke. Time heals all.
May 11th, 2020
I'm in this really weird spot right now, which I've mentioned in previous posts.

What next?

  • I don't feel very motivated about work
  • Nothing feels "important" to work on
  • I don't feel like tweeting (or more importantly writing)
  • I don't want to read any books
  • Everything is just about "tweaking" now

What I mean by "tweaking" now is just that the things that feel important to work on are a bit boring... Content marketing, onboarding optimization, looking at analytics a lot, outsourcing, etc.

But the bigger issue is that I'm not really that content with where I'm at with the business from a financial perspective.

So that's why I think this might be a sign of "burnout" - because I do know for sure that the business has so much room to improve. Usually, these kinds of things would be running through my mind, but lately they are not.

Maybe it's because of the quarantine? We've been locked up for so long... Too much of the same. Too much of nothing.

Deep down there's this yearning for "something new" - like a new project, or new business, or maybe even something new in my personal life... I don't know. 

I do know that I need to be careful with that kind of thinking. I can't jump around for my whole life.
May 10th, 2020
Took pretty much the whole weekend off. 

It's been hard to find "work" to do. I don't feel so motivated.

Maybe I'm burnt out... Or maybe not working so much is a good thing.

Usually these kinds of things are just phases for me - sometimes I go through periods of low productivity and focus and direction...
May 8th, 2020
Came across this video.

It's the story about how a guy got into YouTube, eventually went viral, and how that changed his life.

The part that really struck me is this part.

You will never beat the numbers. Ever. You can celebrate 100K views, a million views, 10M views, a million kajillion views, but the numbers will always win. You will be chasing something that doesn't exist.

This is something I've also experienced.

I remember back when I had my full-time job - I thought that when I got to 1,000 email subscribers, I would be happy. Or when I got 100K monthly visitors on the website, or when I made enough money to quit my full-time job.

But when I reached these numbers-based milestones, I didn't feel satisfied! By the time I got there, the novelty had already worn off and I was already thinking about the next "big number".
May 7th, 2020
New Joe Rogan interview.

Elon Musk is *already* the greatest entrepreneur that ever lived, and he's just getting started.

What I love about Elon is that he is a company builder for life. Even after building successful companies beyond our wildest dreams, he is still building companies.

In this interview, he mocks Warren Buffet as being a bore - and alludes to his "job" being dull - staring at paperwork and deciding whether he should invest in Coke or Pepsi this year (paraphrasing).

It's true though - some people choose to work a lot less hard and make a lot more money. And that's fine.

But Elon is not interested in being an "investor", and he's not interested in being rich. He's interested in changing the world. That's why he put all his own money on the line to build his companies, years after he was already "rich".

If you ask me, that's what life is about.

Life is not about "becoming a lawyer", "getting an exit", or "making passive income like Warren Buffett". We can all get these things with relative ease before we're 30 if we wanted.

But what about after that? After you become that lawyer, doctor, or become a millionaire. What's the next challenge?

Elon's answer? Going to Mars.
May 6th, 2020
In a world full of growth hacks, marketing funnels, etc, we forget the real key to building a business - talk to your customers.


  • Chat with your customers
  • get on calls, do demos
  • Ask them why they're interested in your thing
  • help them with unrelated things
  • meet them in person
  • share updates
  • ask them about their business
  • ask them about their life
  • Chat with prospects
  • talk to people that tried and didn't buy
  • Talk to people that hated your product
  • Ask what they need
  • Ask how your product can improve
  • Ask them what they love about their product
  • Ask them for testimonials
  • Chat with them on Twitter
  • Respond to emails from desperate bloggers/marketers
  • Respond to emails from budding entrepreneurs


  • Automate away customer interactions
  • Put them through funnels
  • Try to trick them with clever marketing
  • Hide things from them
  • Ignore their emails
  • Ignore their ideas and feature requests
  • Ignore their support requests
  • Take anything personal that they say about your product

I came across this blog post - it reminded me that I need to keep talking to my customers. 

It's cool that someone signed up and paid for Pigeon today and I haven't had to have any interaction with them - but that shouldn't be my mentality. I should be reaching out to them - getting to know them - asking them "why Pigeon?".
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.


- 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!