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.
December 8th, 2019
Woke up to the horrible news that Juice Wrld passed away.

When I first checked Instagram in the morning, I saw a photo from another rapper with Juice Wrld, and thought nothing of it. Just another photo.

Then I got to my computer a bit later and realized that it was because he died. At 21.

I was such a big fan of his music. Listened nonstop to both his albums for months on end. Such a visionary and talented musician.

It still just doesn't feel real.
December 7th, 2019
Here is a backdated post for a journal entry I missed.

This time, I am supporting Dianna Allen, creator of Budget Meal Planner.

She is awesome and I hope she keeps working on her indie products.

Screen Shot 2019-12-11 at 5.32.43 PM.png 267 KB
December 6th, 2019
Spent most of the day doing the rewrite of the spreadsheet for Pigeon.

Excited to get done with this - it's the last "big" project until I get back focused on marketing.

December 5th, 2019
fack, long day.

almost forgot to post.

too tired.

i'll hopefully have a better update tomorrow
December 4th, 2019
One quote that always stuckk with me is from the intro of a Dr. Dre song, it goes:

Fear. Fear's a powerful thing. I mean, it's got a lot of firepower. If you can figure out a way to wrestle that fear to push you from behind rather than to stand in front of you, that's very powerful. I always felt that I had to work harder than the next guy, just to do as well as the next guy. And to do better than the next guy, I had to just kill. And you know, to a certain extent, that's still with me in how I work, you know. I just... go in.

It's by Jimmy Iovine.

I really can relate to that quote, especially today. 

It just feels like I have to work so much harder than others to get the same results...
December 3rd, 2019
Typically I do monthly Starter Story reports, but I'd like to start doing this for Pigeon. Since they are two very different businesses, I'd like to do them separately.


Overall, I'm feeling really good about Pigeon - better than I've ever felt about it, I think.

This road of building a SaaS has been really hard - a lot harder than I expected. I've gone through some pretty depressing times - wondering if this is even worth it. But, I keep coming back to it, chipping away, and really proud to not have given up and gotten as far as I have.

If you go back and read some of my daily entries here, you'll probably find some stuff about this.

Signups for Pigeon have been really strong and MRR is at its highest right now.

This next month I will go through the Google audit and I'm really excited for 2020. It's going to be a big year.


Right at the end of October, I was rejected from YC. That really sucked, but a month later, I've mostly forgotten about it.

After the rejection, I put my head down and focused on building a better product. I improved a ton of UI/UX, onboarding, signup, and added a bunch of features.

I spent a lot of time on marketing this year and validating the product. Now, I'm confident it's validated. It's time to get serious.

YC Rejection Letter


MRR is at $783, which means 27 paying customers. This is up from about $667 last month, about 12.5% increase.

I also track active users, because I think it's more important than revenue.

Here's what a weekly graph looks like since we started in May:
Weekly active users since we opened beta in May.

Churn has been rough, although I think it's too early to look at the numbers too seriously.

Weekly newsletter updates

A big win this month has been the weekly newsletter I've been sending. I have about 300 people on my email list, who are both existing/past customers or people who are interested in Pigeon but have not become a customer.

Every Tuesday, I send out a newsletter about exciting new Pigeon updates, usually new features.

This has done a couple things:

  1. It's brought in new customers
  2. It's kept me accountable to ship new stuff in a consistent manner
  3. It's helped me ship faster and become more productive
  4. It's showing customers that we are dedicated to Pigeon

The Chrome Web Store

I remember talking to Ajay Goel from Gmass and he told me a lot of his growth came through the Chrome web store. I am starting to feel this now. Pigeon now gets 3-4 signups per day (which puts people on the waitlist). People are starting to find us through there.

One of the reasons I decided to start Pigeon was because it was a Gmail plugin. Being in the Gmail/Google ecosystem gives you access to a massive userbase (1.5B active users) and a free acquisition channel.

It's also easier to convince people to use your product because they are already using Gmail!

Features added/enhancements

We shipped a ton of stuff in November. Here's the main stuff:

  • Re-engineered the entire email templating engine
  • Made signing up much easier (oAuth flows, etc)
  • Quoted text in email replies
  • Email batching
  • Test sequences
  • Smart fields
  • Lead status updater in sequences
  • Gmail reply box reminders/sequence setters
  • General onboarding / documentation / product education improvements

Next month

Felt great about November, and I have some big plans for December. I will be mostly focusing on product and getting the security audit completed.

High level I'm focused on getting everything sorted for the new year, so we can hit 2020 and grow fast!
December 2nd, 2019
Today was a 12-hour workday.

Woke up at ~8am and pretty much worked until 8pm. Then I ran 3 miles.

It went by in a flash.

This week is crazy.

I need to get a big set of features out for tomorrow's release, then grind out this Gmail security audit, and then get all caught up on Starter Story stuff, and then jump right back into a big Pigeon project.

It certainly doesn't help that because of the past holiday weekend I missed 2-3 solid days of work. I shouldn't feel that way though, it's the holidays!

Although everything feels so hectic right now, I'm really excited about how I'm going to execute in this new month of December. Big plans. I wanna get a ton of shit done in anticipation of 2020 and set the year off right.

Most people "chill" in November/December. I'm grinding and getting ahead. I did this last year and it felt great.

It's starting to feel like things are coming together for Pigeon - it feels like more people are signing up every day or at least being interested. I just need to keep putting in this kind of work. It will all pay off.
December 1st, 2019
I apologize for missing updates for September and October.

I was traveling on and off, and when I did have time to work I was super busy and needed to focus on business tasks.

Before jumping into November, here's a quick glimpse on traffic for those months:

November - our biggest month ever

But this month is about November, where we hit over 100k uniques!

November 2019 Traffic

Much of this is thanks to a really big Hacker News post that went viral. You can see the 20k+ uniques we got in one day. Even without the big Hacker News push, this still would have been the biggest month.


In November, we published 57 interviews. I'd like to be publishing at least 60 interviews/month but this month had a holiday and November/December have historically been slow for us because businesses are focused on Black Friday and the holidays.

In the new year, I expect a big spike in traffic as well as content output.

Content calendar November 2019

Email subscribers

We are just days away from hitting 10k email subscribers.

However, email list growth has been really slow. I removed the CTA on the main page to put in the search box, which hasn't helped.

In December, I have a project to increase email optin rates, which I will use a bunch of tactics from this article.

I think it will go up a ton.

Daily subscribes to email list for November


Revenue for November was $7,594.

Big tasks completed

Nowadays, I'm more focused on "bigger projects" within Starter Story.

Now that much of the content and "day to day" is owned by our small team of freelancers, I'm freed up to work on development/experimental projects, scaling, and generating revenue.

We try to find a way to automate or outsource most things and stay as lean as possible.

Here are some of the big things completed in November:

Adding more Pinterest templates

I'm always looking for new ways to distribute content for Starter Story, and I've been running an experiment on Pinterest where I auto-generate image assets and post on Pinterest.

Been doing this for a couple of months now and it's starting to pay off, you can see the graph taking off in last 30 days:

Pinterest impressions over last 90 days

Improved social media

Our social media is completely automated, but I did spend some time making captions better and getting the auto-generated assets working properly.

I also added a LinkedIn channel to Buffer, and I post there regularly now.

Submit form

I added a submit form to the site.

We never had this before, as I always encouraged people to email me and go from there.

This new form brings in 1-2 legitimate interview opportunities per day. Pretty cool to see it working!

One of my goals for next year is to build a more "self-service" interview process. This form is one of the first stepping stones to get there.

Follow up stories

We are now doing many "follow up stories", as we call them.

These are interview "updates", i.e. we interview someone again 1 year later. This project has been really successful, and we have over 50% of founders agreeing to do one. Surprisingly, most of them say yes!

This is great because it's confirming that founders do see a nice benefit from sharing their story on Starter Story, and they're willing to go through the work to do it again.

I set up a Pigeon integration that would reach out to past interviewees to see if they want to do another interview.  And getting them to write good content is really easy since they've already been through the process :)

Testing out lifetime membership

For our premium membership, I removed the free trial and only included a monthly, yearly, and lifetime membership.

I thought that we would see a lot more people signing up for the lifetime membership, but that has not been the case - we haven't even had one lifetime signup since introducing it about a month ago.

Signups are very much down after removing the free trial, and overall, I'm not very happy with results. I will reassess at the end of the year and see it makes sense to bring back the free trial.

I also paywalled a couple more things around the site, such as filtering businesses.

Increased exposure for Klaviyo

Lastly, I added new ad spots for Klaviyo in an attempt to drive more traffic and exposure to their site.

Since they sponsor the site exclusively, I want to make sure to send them as much traffic as I can, so I added this to all interviews on the site:

New ad spot for Klaviyo

The results for that have been super good, driving ~3x more clicks for them across the site.

I hope you enjoyed this month in review! Lots of cool stuff planned for December.
November 30th, 2019
Today I am traveling from Salt Lake City to Jackson WY, where I’ll stay and work for at least a month.

More on Jackson life soon.