December 28th, 2019
Last year, I set really ambitious goals for 2019. Although I hit a lot of them, the goals were too expansive and specific, like hitting $X/month in revenue, running 1000 miles, publishing X YouTube vidoes, etc.

It was good for last year because I didn't really have a good vision for what I wanted to do in life. But in 2019, I figured out my more "overarching goals" which are to build a successful business, spend time with family & friends, and fitness stuff. My goals are more about the next 5-10 years and I'm very focused on that.

I'm also a lot more confident in what I want out of life and I really don't need "goals", because I'm dedicated to working on these things every day and they are basically habits for me now. So, I'd rather set monthly goals and these often become weekly and daily goals embedded into my brain.

So, for 2020, I'm not going to set goals like that. I'm not really going to set any goals.

However, one thing I want to get better at is spending my free time on more interesting things and improving myself as a person, as well as learning new things and keeping my life interesting and my day's invigorating.

So in 2020, I want to dedicate each month to learning a new hobby or subject, or trying something new, and just "immersing" myself into it.

This is my personality - I find something new and get obsessed with it. I really enjoy learning about new things. So, I want to take advantage of that (but also not let it take over my daily life).

So, on evenings after a long workday, I want to have some new hobby to look forward to that is productive. Something to do with my extra hours that gets me excited.

Each month I will pick a "thing" and research it and execute on it.

I don't know exactly what they will be yet, but here are some ideas:

  • cooking
  • drawing
  • stand up comedy
  • graphic design
  • coffee roasting
  • learn an instrument
  • make beats
  • learn a new language
  • skateboarding
  • public speaking
  • Run 10 miles/day
  • 5am wake up
  • Read x books
  • get into anime
  • get into short stories
  • schedule my entire day
  • something with vlogging/Youtube

As the year goes by, I will keep thinking of more based on new things I learn and get excited about.

At the beginning of the month, I will pick something and create a mini-plan, and plan to dedicate some time to it every day, if needed.

For January, I pick cooking. It's good timing for me because I am living at home with full access to a kitchen and I'd like to save money, learn more about meal prepping, and I'm counting calories to lose weight for my marathon in March.

Subject to change though! More to come soon!
December 27th, 2019
I came across this blog post yesterday which felt like a bit of a wake-up call.

Especially, this excerpt:

To keep growing, to keep living even more deeply and authentically into what makes you come alive, invite yourself to risk what brought you to where you are today.

2018 felt like my breakout year. I took massive risks, built a new business off the ground, quit my job, launched some huge projects like the 24 Hour Startup.

But 2019 didn't feel like that.

It felt a bit like I crawled into a hole and hid away. I picked a new product to work on and didn't talk much. I didn't tweet much. I didn't put myself out there as much.

I think this is partly due to fear of what people thought about me.

I'm not regretting it, but I think my success shocked me a bit. It made me feel like I needed to keep "one-upping" myself.

This is not necessarily a bad thing - the new project I was working on was the antithesis of this mentality. It is a project that takes time, and there will be no breakout success. So, going heads down is essential sometimes, all creators do it. 2019 was about working hard and not talking much.

I'm really hard on myself. Because I'm so focused on building Pigeon, I tend to forget about my success and all of the things I've done in the last couple years.

When people ask about how things are going, lately, my answers are something along the lines of "good, not great". But the reality is that things are going great if you compared them to 1 year ago.

It's just that the novelty has worn off that "I started my own profitable business, live my own life on my own terms, and make almost $100k/year doing it." I don't even want to tell anyone anymore that.

It's never enough - sure that is a good poisition to be in right now - but will it be there next year? Could it all fall apart? Yes, that's why I need to focus on bigger to make up for that. I don't want to "do OK for myself" but have to go back to the corporate world in 10 years. I work so fucking hard right now so I don't have to work ever again past 40 years old.

All I care about is the success of my new project, and I won't be happy until I can tell people that it's successful.

The issue is that the "success" of Pigeon has taken longer than expected, and may take another 1-2 years. I can't sit in silence that long. I think about how I'll finally "come out and tell the world" when I hit $5k or $10k/month, but that might be a really long time, and I need to figure out a way to put myself out there while I work on that.

Because the reality is that putting myself out there is the best thing I can do, both for myself or my business.

I need to remember that nobody actually gives a fuck. I have this impostor's syndrome that my Twitter following will see me as a fraud, because I couldn't be successful with my new project as fast as the next wildly successful SaaS founder.

I need to be comfortable with losing it all. With losing all my "cred".

From the article:

Who are you willing to continue to become, even after you’ve accomplished some success? What are you willing to risk, to continue going in the direction that is calling you?

Will write about this more. I think there is an easy solution to conquering this, just need to think about it a bit more.
December 26th, 2019
Just got an email from the security auditors. Sounds like I’ll be getting the letter any day now!

Back to actually working tomorrow!
December 25th, 2019
Been taking the last two days off work and spending time with family.

Merry Christmas!

Heading to Salt Lake City tomorrow and will spend a month there. Really looking forward to the new year.
December 24th, 2019
Today, I did Orange Theory with my sisters here in Jackson, WY. Then, we went cross country skiing out in Teton National Park and it was snowing one of the hardest I've ever experienced.

Then, we had a sushi making party and opened Christmas presents. Waking up early to ski tomorrow.

Happy holidays! Back to work on Thursday I think.
December 23rd, 2019
(this is a note I wrote today as part of my plan in 2020 to focus on marketing for Pigeon)

While I was traveling for a couple months, I didn't have much time to spend on development. I think that gave me a glimpse into all of the shortcomings of Pigeon, especially with onboarding, design, and features.

So when I got back, I decided it would be a good idea to focus solely on product. It's been about two months, and we have come very far. Added some massive features, way better documentation, etc.

It was great timing because of the security audit, but now that is finally about to be over.

Product is important, but I think marketing and customer support is more important right now. We came a long way in the last few months with product, I feel so much better about the product right now.

Product is also relatively easy to improve. We can always improve product. But getting the foundations for the marketing is more key right now.

But I remember what it was like when we were posting on Quora every day. That was a bit of a "validation" phase, but it also was great marketing. A lot of experimenting, but now I see the benefits of that relatively small marketing push.

In other words, it's time to focus on marketing. It's time to change my mindset about how to grow this thing.

I know I have some of the skills to have a marketing success, and I think those skills are:

  1. Automation and outsourcing - use those skills to build a marketing machine
  2. I know how to pump out content (from my experience at Starter Story)

How much time should I be spending on marketing? I need to keep myself accountable.

I should be spending 75% of my time on marketing and customer support. 25% of my time on product development.

I need to keep myself accountable for this.

TODO: add a weekly reminder to roughly track activities

How much budget can I be spending?

Put all Pigeon revenue into marketing. Which should mostly be for paying for writers (for content). will address that in a bit.

What are the ways we can "kill it" in marketing in marketing?

It's important to stay focused on a few different ways, but still keep it diverse and try new things, and of course keep it fun!

Here are the things we should focus on:

1. Quora post & blog strategy (25%)

Just like we did before, post on Quora 5 times per day. Find the blog posts that perform the best in google search, where Quora performs the best and build blog posts around those. really easy to automate this one. Outsource/automate as fast as possible. Just need to be careful about spamming and that kind of thing.

2. Blog posts and tutorials (how to X) (specific to use cases) (25%)

These are blog posts that show off the power of pigeon or show users how to do something that would be beneficial, like how to get on podcasts or something similar. These will also be specific to use cases that I pick and deem worth going after (which will be determined soon). Do this myself until I find systems to automate/outsource.

3. Case studies with customers (10%)

This is an easy one. Offer users a free month of Pigeon if they can answer a small questionnaire. This gives them a nice backlink, and I also get to learn more about what they do and how Pigeon helps them. It's a win-win. Easy to automate/outsource.

4. YouTube videos (tutorials) (25%)

These will be mostly recycled from the blog posts and tutorials (always do both). YouTube is a massive channel. let's plan for some fun stuff here too, like emailing all congresspeople or something like that. Take advantage of memes!!!

5. Alternatives page (one-off project)

Super easy to do and it's mostly a one-off. - do this myself and get it done.

6. Side project marketing (chrome extensions) / publicity (10%) - weekend projects

This is a huge one but should only be done as weekend projects because I don't want to get carried away. First example will be "Block Sender". Launch on Product Hunt, Hacker News, etc. Do it all on my own site, and with Pigeon branding, like "Block Sender by Pigeon"

7. Email marketing / build an email list (5%)

Send update email every week, no matter what. Stay humble, be funny, keep it interesting.

Find use cases and get specific

One huge problem with Pigeon is we don't have a specific market, my plan for that is to find some. So, the goal is to go after 3 different markets with the Quora, blog posts, and YouTube videos, and many more.

I will test these for 3 months. If one doesn't pan out, will pick a new one - if one is working out - then just keep going with it. Always have 3 different running at a time.

(those use cases / segments will be determined by the end of the year)

Set a plan

At the beginning of the month, create and set a plan for how much content we will do. A plan could be like this:

I put about 60 hours / week into Pigeon or 240 hours per month. 75% of that 180. Meaning I should be spending 180 hours on marketing things.

In the first month it might look something like this:

  1. Fully automate and outsource quora strategy
  2. 10 blog posts (that are Quora copycats)
  3. 4 case studies with customers
  4. 4 pillar blog posts / tutorials
  5. 4 YouTube videos
  6. Release a chrome extension
  7. Deploy alternatives pages

What should I be doing (every day)?

My focus should be to automate and outsource as much as possible. I should be trying things, seeing if they work, and then building process and outsourcing them. As always, learn myself and start small with a limited budget, having people work on the smallest things first.
December 22nd, 2019
Since some big life changes over the last couple years, my "going out" and drinking life pretty much evaporated.

I used to be a big drinker, going out at least twice a week and sometimes having 6+ drinks.

I'm not really sure why this happened, but overall, I just started feeling way less interested in going out. Even when I was with friends and we went out to dinner, I would often bail out before the "big" drinking started.

Or I would just opt out of events that were clearly "drinking just to drink". That's the difference to me. I enjoy going out and doing things, but if it seems like drinking is the focal point of the event (going to a club, house party, etc) then I'm way less interested.

However, I love going to concerts, sporting events, dinners, or even just going to bars with friends where you can actually talk.

One reason why I went out less is I couldn't really justify the hangovers anymore. Having a hangover all weekend is OK if you have a 9to5 job because your schedule is basically built for it. But if you run your own business, your hangover is a liability. Each night out (+hangover) steals 8-10 hours that you could be using to improve your business, or to take some quality time off.

As I stopped going out, I would watch my roommates in pain every Sat/Sunday morning at 10am, vegging out on the couch, ordering takeout. Meanwhile I woke up feeling fresh, got a couple of hours of work in, or even a good run!

And although I might have had some FOMO the night before, I never regretted it after hearing what actually went down because I realized never really missed anything.
December 21st, 2019
Because I missed a journal entry today, I'm electing to support James Ivings and Danielle Johnson, two makers that built Leave Me Alone and a few other cool apps.

Recently, they launched a Chrome extension called Subscription Score, and I'd like to see how that works, so I committed $5/month for it.

December 20th, 2019
It's been over a year since I quit my full-time job.

That means it's been over a year that I woke up every day and made my own choices on what I wanted to do, what I wanted to work on, and how I would plan out my day.

It feels so normal now, but I think it's nice to write about it every now and then because I don't want to take it for granted.

In the words of Freddie Gibbs:

This how it feel to wake up and you don't owe nobody shit.

Doing your own thing gives you confidence, it gives you a purpose and meaning. You are your own person. You don't owe anyone anything, other than your own choices and decisions you made (i.e. you have customers because you built a product).

I can't imagine it any other way.

I have friends who have great jobs. Doctors, lawyers, tech executives. When they tell people about what they do, it sounds impressive.

I don't have that. 

But they have to go into work every weekday on a schedule. They have a boss who tells them what to work on. They have to plan their holidays and ask for time off. They have to work through office politics.

Working hard for someone else's dream. To put a fancy logo on their resume. To say, "I do [INSERT FANCY JOB TITLE] for [INSERT FANCY COMPANY NAME HERE]".

I don't have that.

But what I do have? I have that "fire", the passion for what I do that no employee can ever have. And if an employee does have that kind of passion, they are likely naive or new in their career.

Which is why I have so much respect for artists, creators, entrepreneurs, philanthropists, etc. It's not about money, it's about impact. It's very uncommon to hear of highly impactful employees, I think - so for me - I have no interest in being an employee ever again.
December 19th, 2019
One of my best friends from high school is trying to make a career in music.

Back in high school, we worked on music together. I moved on and did other things, but he never moved on. It's been over 10 years and he still has the ambition and is working to make it in the music industry.

I have so much respect for him and how he had the same vision for so many years.

He never changed. He always kept it real.

For me, I've always changed, for better or worse. Maybe I change too much, and give up on things too easily.

Recently, it seems his career has been on the "up", and a verse from one of his songs really got me inspired.

Sometimes I think
All I been doin is tunin' these strings
I should just quit with these stupid ass dreams
I should go with the current instead of swimming upstream
And then I see the sunlight shinin' on these tall ass trees (chuckles)
Even these muhfuckas grew from a seed
I can't lose my steam
I keep on doin' my thing, I'm doin my thing.

I feel this way too.

When most other people are out here with their normal jobs, life, and Instagram posts, I feel like I'm taking the hard route to pursue some wild ass dreams - to run my own business and build something bigger than myself.

Some days/weeks/months you feel like you aren't making serious progress, or sometimes even taking steps back.

But you have to see the bigger picture, see it as the tree that grew from a seed, that took 20 years to become what it is.

Don't worry so much about next month, or next year's sales/numbers/progress. Look at the 20 year vision. Follow those stupid ass dreams, anyone can make them happen in 20 years.
December 18th, 2019
I stumbled on an article on Hacker News today.

It was called "A Failed SaaS Postmortem". As someone who is in the middle of building a SaaS, it sounded interesting so I gave it a click.

I started reading and found that this guy had worked on this project for 3 years. Feels like a long time - one day I'll be there...

Started reading more. All he talked about were his bad technology decisions and the minutiae of different technologies and micro-services.

He admits this was his downfall, but I found it interesting that he never really talked about why it really failed.

Of course, he mentions that it failed because he didn't listen to customers, but it sounded like he didn't even try to get customers. Like, he never made it past the technology struggle. How complex could the technology be that it kept you occupied for 3 years?

I read that article and had somewhat of a sigh of relief. It's hard to imagine giving a single fuck about that kind of thing (technology). 

It actually doesn't make sense to me. I am only interested in using the tools that I'm comfortable with - I have no motivation to even try new technologies. Sometimes I'll get caught up in some gem or library, but then I usually GTFO of there when things get complex.
December 17th, 2019
I started my vacation on a sour note.

I stumbled onto Indie Hackers right before the vacation started and I got really bummed out/jealous of someone else's success.

As my "vacation" started I kept thinking about it. Started by feeling crappy but slowly that faded away.

I was working a lot before this time off, and when I work a lot, I'm just constantly thinking all the time about my business.

So taking this time off it took a few days to get my mind off of things, but it was really nice to not think about it as much. Slowly, the constant thoughts faded away.

It felt rejuvenating in a way.

But I also had a lot of time to think, about Pigeon and the future. Because part of me feels like maybe I'm going down the wrong path or that I'm not making the right moves.

The real concerns are:

1. I made a product that does too many things
2. That's OK if the product does a lot of things, but can 1 person sustain it with support, engineering, and marketing?
3. Bugs are getting scarier
4. Onboarding/support is tough for a product like Pigeon

Overall, it's a feeling that the product is too ambitious. Should I have dialed it down?

This is certainly making things harder for me.

However, I don't think it makes things impossible. I still don't think it's worth giving up - I just need to be smarter about my future moves.

Regardless of all of this, I need to see these as mistakes that I needed to go through to learn.

Building too many things into the product was a mistake that I needed to learn.

And all of this hard work and pain will lead me in the right direction, whether that's a pivot, a different product, etc. It's better to keep going than to just give up and go back to the drawing board.

And you know what, I also had a mindset change last week - I'm not scared of churn anymore. In fact, I welcome it. This is a big turning point for me, I think. Being more indifferent is the key. Focus on what you can do to fix things, don't think too much in the past or let the ego get in the way.

Thing is, I know Pigeon can be successful, I just need to up the marketing and focus in more and more.

Every day, I'm working on new initiatives that are moving the business forward. I don't have a grand vision. Just moving slowly in the right direction, or at least what feels right.
December 16th, 2019
Took ~5 days off, and today I got back (for pretty much just a half day).

Wanted to reflect on my first time off in a while, but it's gotten too late after building some logic that lets Pigeon work on multiple tabs.

Now, I'm just going to relax and write that one tomorrow.

And I have an early meeting tomorrow. See ya tmrw.
December 15th, 2019
Last day of my mini break!

More full update tomorrow!
December 14th, 2019
Taking a break this weekend and not doing anything work-related.

Still want to get these daily updates out!

But for now, I'm headed to the mountain to go skiing for the second day in a row.

The time off is nice, and I've been thinking about a lot.
December 13th, 2019
Stumbled onto Indie Hackers today, saw the top milestone was from someone in the same space as me who just hit 100K users in the same timeframe as me.

Here I am with ~20 users.

Their product is far simpler than mine, and they likely don't have to go through a Google audit.

I get jealous when I see those things. What am I doing wrong? Seeing that makes me feel like I've done everything wrong.

This is why I don't like to go on Indie Hackers anymore, what's the point? It's just a distraction.

I don't gain much benefit from learning they are at 100K users. You could argue that you could learn something from them, which is somewhat true. After seeing it, I looked closer into their business and their marketing.

But you can also argue it's just a massive distraction and probably will leave you worse off.

Not only did it make me feel shitty, but it makes me rethink my business and second guess myself.

If you second guess yourself every day, then you will never make decisions forward or progress.

Learn by failing by yourself.
December 12th, 2019
The last few weeks have been tough, I'm finding that I'm becoming more "worried" about my businesses every day.

I'm nervous every morning I wake up and check my email. Will there be a new churn? A really bad bug? Will my employees quit?

To a degree, I think this is normal. When you run a business you always have that lingering feeling that it could all fall apart.

But it wasn't always this bad for me. It has definitely gotten worse.

Something needs to change.

I associate my own ego with my business. To me, my business is a part of me. So when something bad happens in the business, it affects my mood, my self-worth, etc.

When I was running Starter Story, I felt less like that. I think part of it was because I had a full-time job, so money wasn't an issue. The project could fail and I'd be fine. And also, I cared less about the idea and the market. I felt that I was more indifferent to the content and the idea, because I was interviewing other people. It was less of a representation of me.

But that is different with Pigeon. Each churn feels like a big blow, and I often take it personally.

Over the last couple days though, I feel I've been climbing out of this mentality. I need to accept the fact that all of my customers could churn tomorrow, go to $0 monthly revenue, and I would still be OK. And I still wouldn't quit with the idea, just adjust and keep focusing on the future.

I still have a successful project that is making money and enough runway for a couple years. 

I will always figure it out.
December 11th, 2019
Time and time again, I hear the startup advice... something along the lines of "don't build a product and find a market" but "find a market and build them a product".

I didn't follow that advice.

Well, I sort of did. I picked bloggers or people that run sites similar to Starter Story. But that market ended up being way too small, and way too early.

So I thought picking a userbase would be enough, Gmail users - because Pigeon is a Gmail CRM. That does give it a lot of leverage, as 1.5B people use Gmail.

But I didn't choose a market. And it's biting me in the ass right now. Churn is high and I'm building something for too many people.

Why didn't I do this?

  1. I'm stubborn and I didn't listen
  2. I thought I could "figure it out as I built it"
  3. I didn't have any idea what market to go for

The good news is that it's not too late.

As I continue to have the realization that I've been doing it wrong, I can work to change things.

How? Start looking for markets.

Now that I'm close to being done with the Google audit, the world is my oyster. I've built a great product and now I just need to find the best users for it. I can still keep the use case wide, because it's so flexible, but I can now pick and choose who I should go for, as long as I can plan it right.

Over the last hour, I created this spreadsheet:

A go to market strategy

Across the columns are questions, which can be answered on a scale of 1-10. Along the rows are different use cases and potential customers.

I've been scouring the Chrome store reviews for Streak to populate the rows. Total up the scores and maybe that can determine was use cases I should go for.

Once I know that, from a distribution side of things, I have some confidence that I can reach those people (with proper planning). I got Starter Story to 100K+ visitors, I think I can figure out some of the marketing stuff.

I'm excited about the future. Time to find customers that really need this tool.

(this spreadsheet/idea is a work in progress - I'll keep this updated on how it goes)
December 10th, 2019
Some of these recent days have been harder than in recent memory.

It kind of feels like things are just slowing down for me. In my businesses. I feel like I've lost some of the excitement that I had a couple years ago when starting my own business.

Maybe because it's December (and it's slow), or maybe I'm just too isolated these days.

I want to do something bigger than just have a programming job and go through life.

I want to be somebody. I want to have unique ideas and people to look back and remember me. I want to influence and drive change in the world, and people.

But on harder days, I think about how I could be making lots of money in a corporate job and live in New York and be getting married etc etc.

Am I too late for this? I'm 29 and going to be 30 next year. Do I have time to do all this stuff that I want to do? Build a successful business, make money, build a family, etc etc.

I'm working too much lately and it sometimes feels like I'm not making progress.

Whatever the case, I can't see myself going back to a job. For me, that is throwing in the towel, and would be a big setback. I will do anything to not be there. I will do consulting or sell courses if it came to that.

December 9th, 2019
I don't want to admit it, but I spent the last 5 days rebuilding the main data grid feature for my product.

I basically worked all day every day - I needed to rebuild it because of some big performance issues that customers were facing.

Why were we facing performance issues? Two reasons - I picked a "toy" library months ago, and I wasn't smart enough at Javascript to fix it myself.

This rebuild has been nagging at me for months. I needed to do it. This last week was the week to do it.

"Pick the best library"

I knew I needed to use a good library, but this time, it better be a "good one". So I did a bunch of research on the best table / datagrid libraries for React, and I decided to go with react-data-grid.

A couple hours into it, I was flying high. Everything was working great, I had implemented about 60% and it was looking slick. 

Then I found an issue. Then another.

Hours go by, I'm making progress, but a lot slower now.

I find myself scouring Github issues from 3 years ago, unresolved, stale. I see someone else is having the same issue as me, but nobody responded. Damn...

I find myself in an endless loop on the same Github issues and Codesandbox examples.

I stumble on a thread with dozens of comments about how the library is unreliable and the owner is unresponsive.

Eventually, I give up.

"Pick another library"

"Fuck, I'm 2 days in and I'm switching libraries? I'm a loser."

I'm going to a more low-level library, react-table.

This library looks promising, the owner is constantly making changes, the library is well-maintained and well supported.

And plus, a lot of the work I've done can carry over, implementing this new library should be much easier.

I go back into the zone, implementing faster than last time, I'm almost surprised at my Javascript skills?

I know a lot more than I did about Javascript last week...

I'm about 80% done, now I need to implement this last feature (spreadsheet grouping).

I cannot figure this one out! I feel stupid. I look at the examples over and over - they are using React hooks and memoization. I don't get it.

I put in debuggers and try everything. Hours go by, and I'm so frustrated.

I'm scouring Github issues and realize the feature doesn't work in the current version, they are working on fixes...


"Take a break"

I take a break for a couple hours, my first break in what feels like days.

I hop in the shower. It's a long shower. I'm starting to have shower thoughts, reflecting on my implementation and what I've learned. All I can think about is this project. I NEED to get it done.

With this sudden break in coding, I have a revelation: "Fuck it, I can just build this myself"

I scrap the lower-level library.

I implement it myself with pure React and javascript.

I do it in less than 2 hours.

"How was it that simple?"

I feel confident. I understand how the thing truly works.

I'm excited about the code. Adding features will be easy. I won't need to comb through broken documentation and closed Github issues when I want to add XYZ. I'll just build it myself.


Felt like I had to write this down, as the last few days were such a roller coaster.

But after ripping out my hair, yelling at my computer, screaming with joy, and dreaming every night about code, it's done now. It was all worth it.

Deploying tomorrow.