March 6th, 2020
I’m not one of those “I have imposter syndrome woe is me” type of people.

But I definitely experienced a little mini revelation about impostor syndrome.


Before my startup days, I worked as a software engineer. I learned coding from a bootcamp, a non-traditional route.

To be honest, I never thought I was a good engineer. I wasn’t a bad engineer, I was just very mediocre.

I was never able to talk “high level” with other engineers about programming concepts and technologies, so when our engineering teams would have discussions or meetings, I would feel inadequate and just shut down.

I was never good at code reviews. I couldn’t (and still really can’t) read code abstractly - in other words I’m not good at reading code on paper and understanding what it does. It’s better if I write it or walk through it with a debugger.

It always felt like I was moving too slow, and the other engineers were just a whole different level in terms of skill, speed, intelligence, etc - they could just pick things up faster.

After the boot camp, I got a programming job for $105K in SF. I always felt like I was overpaid - for the work I did. “This week I shipped only test code and make $X” or “this week I made a simple change to the settings page”.

I felt like my salary was so high that the company would finally have enough of me and let me go. 

I would get called into a 1:1 with my manager and I was certain I was getting let go, or given a warning about how slow I’m shipping.  Then, they would say “Pat, you’re doing a great job and we’re giving you a raise”. Haha! (Not a crazy raise just normal stuff though)

Once I got a programming job in New York City, I upped my salary again, from what I was making in SF.

That NYC startup had a much stronger engineering team, and I legit felt like I was the worst engineer on the team. However, I had this eerie feeling that I was making more than some of the extremely talented engineers.

This gave me even more impostor syndrome… Anyways, the list goes on but that’s not the point of the story.

Once Starter Story started taking off, I quit. Quitting felt almost like a relief - like I had somehow escaped my firing… I didn’t quit for that reason obviously - I quit to follow where my passion was and start my own business.

It’s been over a year since I quit, and I actually heard from a friend that they had some layoffs in their engineering team a few months ago. I laughed about this and said something like “if I was still working there I would have been one of those layoffs! Thank god Starter Story worked out”.

Anyways, the moral of the story is that this impostor syndrome was mostly in my head!!

Why?

Because today, I got an email from the CTO - he asked if I was interested in picking up some contract work for them. 

Me being asked to do contract work? As an engineer? Who the fuck would want to hire me for that!? Haha!

Getting that email was a nice feeling, a little pick me up that I’m not a good-for-nothing software engineer :)
March 5th, 2020
Today was one of those days where I felt so productive that I felt like I was high on drugs.

Sometimes, for me, the feeling of being productive is like a rush. It can be very exciting and enlightening at the same time.

Maybe it felt like this because of how unproductive I've been in the past week...

And as I was leaving the library after what felt like a great day's work, I kept thinking "man if I could be this productive and working on the right things every day I could get so much more done". Because I'm starting to realize it's even less about being productive, but working on the right things.

For me at least, when I first started to feel like I was becoming a more productive human, it was all about the systems - mental, organizational, etc - which is a great place to start - but I think as I develop as an entrepreneur I'm starting to see the most important thing is picking the most important thing and just working on it until it's done. It's that simple. It's so deceptively simple that nobody can even see it - I think 99% of people won't even realize it in their lifetime.

Instead of putting 20 things on your todo list like "clean room" and "go for a run", I need to put the actually most important things FIRST. Get those done now, and then I can "do my laundry". And knock those out by 9:30AM - the items that have been sitting on your todo list forever, but you keep putting them off because they are not fun, or they are scary and give you fear. Or maybe they are not even on my todo list because I'm so scared of them.

But if I can work on these things every day, I know I can get so much further. 

It's less about prioritization, and more about conquering my fears. For me, that could be something like launching a podcast, or asking that girl out that I think is cute, or public speaking. These are just examples, but they are things that I am (or have been) deeply scared of. 

And that's why I keep putting them off. 

If I can identify those, get them done, then I can be superhuman.

Writing this stuff really helps...

I heard this Peter Thiel quote the other day:

How can you achieve your 10 year plan in the next 6 months?

I can't stop thinking about it. What if I could actually get my 10 year goals completed in 6 months? Then I could get 20 10 year goals completed in 10 years! It's really a great question I'd like to ask myself more often.
March 4th, 2020
I need to do less "small things".

Lately, I can *feel* my tolerance for "small things" getting higher. I've been taking too many meetings, too many phone calls, and I'm generally too optimistic lately, I think.

I want to help more people, get more help, make more online connections, and be more involved in the community, but I also feel like these "small things" can be a huge detriment for me personally, just knowing how I operate. Hanging out on Telegram & Twitter & WIP.chat & etc has been awesome lately, but if I look closer, it's really preventing me from getting important stuff done.

I cannot multitask well. One of my best friends (and also extremely productive guy) crushes his todos while watching Netflix - I cannot wrap my head around that.

Yesterday, I woke up at 7am (been waking up early lately) and I got to noon and I had not done any of the big things I wanted to do that day. Just got 7 "small things" done. I realized I was 5 hours into my "workday" and I hadn't done shit!! I was "working" but it was like my brain was scattershot. Not focused. Not deep work.

Just small bullshit items like "reach out to X about failed payment" (an example) and "tweet about Y" and "add weekly calendar event for Z" and other non-essential things.

I've just given myself too many "small commitments" - for example - joining someone's podcast, or even this daily journal. Each little thing like that really does add up big time.

Maybe this is just one of my mood swings. One month I'm completely heads down and don't check Twitter for a month and pessimistic about the maker scene, and then another month "it's the greatest thing in the world" - probably all in my head and also tied to my own success, but yeah...

But it's pretty easy to fix this. What I've been doing lately is cutting my daily todo list from something like 12 items to 3 items. By cutting it down you have to pick the most important ones. The 9 "small things" can wait. OR, you should do them when you think about them. There is a book called Getting Things Done, that says "if you can get something done in 2 minutes, just do it right then" - I need to be better at that.

As always, I need to have a balance.
March 3rd, 2020
When I started writing this daily journal, nobody read it because I never really talked about it. I just wrote every day and I still liked the fact that it was public.

But over the last month, it's started to get some traction. I've been checking up on analytics, and even after the massive traffic of the Hacker News posts and $1K MRR update, the blog is now getting almost 1k page views per day!

The fact that I keep checking these analytics is bad (for me). I fear that optimizing my journal entries for views defeats the purpose of this thing, and it will make my writing worse, or less honest. Lately, I've also felt some more pressure now to deliver a great post every day.

I also think about some of the people that (I know) read this, and think things like "What will X think when they read it"? That is very bad for me.

However, I would be lying if I said that I didn't want people to read this. I would be lying if I said I didn't like that lots of people read it.

People reading it is a motivation for me to do it every day. If it were private, I probably wouldn't keep up with it. Part of the reason for that is probably my ego, and also, I want people to follow the journey, get inspired, and (one day) look back at 4-5 years of journal entries and see what it takes to build a successful business.

So, I won't be taking this private but I will be removing the analytics. I also won't be doing anymore self-promotion other than for milestones and stuff like that. If people read something and love it, they can share it (and I love that).
March 2nd, 2020
this is an excerpt of a monthly email I send to stakeholders

Feb 2020, tldr:

Although traffic was down slightly, Feb was the highest all-time revenue for all projects. Most of Feb was spent shipping features and increasing content output. For March and the foreseeable future, we are focused on adding more value to Starter Story and monetization, including launching a community for Starter Story mid-March. We will also be moving towards freemium for Pigeon (target mid-April).

the good

- A breakout month for pigeon ($1k MRR!)
- Implemented big features to add value to starter story premium (better explore page, csv export, deals on tools)
- Announced starter story community launch date (will be FB group)
- All-time record for starter story interviews (87 shipped interviews!)

the bad

- Traffic down due to slower month & no longer sharing on Reddit or hacker news
- Not making fast enough progress on UGC content - only shipped 1/8 planned (example)

Numbers:

- Total Revenue: $8,898 (88% Starter Story / 12% Pigeon) (+$351)
- Starter Story Traffic: 80K uniques / 106K sessions / 143K pageviews (-20%)
- Interviews published: 87! (highest all time)
- Email List: 12,061 total subscribers (+643 net subscribers)
- Starter Story Premium MRR: $1.2K (highest all time)
- Pigeon MRR: $1.1K (highest all time)

What got done / what went well:

- Onboarding email drip for Starter Story Premium
- Created a form where we ask people why they canceled
- Added discounts on tools (incentive to sign up to premium)
- Announced the launch date for Facebook group community
- Published 87 interviews
- Published 3 more pigeon case studies
- Added more tags on Starter Story backend
- added onboarding email drip for Pigeon (example)
- Pigeon: Added more smart columns
- Built MVP of new lead crawler for Starter Story

Goals for March:

- Launch the starter story community and get it rolling
- Get Pigeon freemium ready for april 10 launch
- Focus on Quora & content marketing for Pigeon
- Finish automated outreach project
- Finish the start page
- Self-service interviews MVP for starter story
- More roundups/UGC for Starter Story (8 posts)
- More content marketing for Pigeon (30 Quora answers, 4 case studies, 2 blog posts)
- Pigeon suggested actions feature
- Pigeon link tracking automation feature

Thanks for reading!
March 1st, 2020
Each month this year, I'm focusing on a new hobby.

So far:


I actually enjoyed the book as far as I got in, but I found it really hard to motivate myself to read it, at all. I wish I was more into reading fiction, but maybe it's just not for me... ? I don't know.

Anyways, onto the next "hobby".

For March, I want to get better at design, UI, and UX and learn more of the fundamentals and be able to implement into my apps.

How I will get better? I will start with some essential books and courses. I just tweeted about it, so let's see what people say.

I've already read Refactoring UI, but maybe I'll read it again.

More to come soon.

(if you're reading this and think I should check out some resource, please send to me!!)
February 29th, 2020
I was chatting with Armin & Melanie from Placid about building a bootstrapped SaaS/app.

We started talking about how it really is a "grind". You really have to do so much work to get 1 customer. You have to do sales, onboarding, support, product development, etc - all by yourself. It's actually kind of crazy how daunting this is in the beginning.

But somewhere in this mayhem, I think there might be a "matrix" or "system" that can lead to a successful product.

This is a really rough concept, but let's call this the Talk/Fix/Improve/Automate process. It goes something like this:

  1. A customer tries your product and does not know how to use it
  2. Customer reaches out with a specific question or feature request
  3. You respond to the customer with the best possible answer
  4. You make a decision if you should change the product, add more documentation, add that new feature, move feature up on roadmap, etc
  5. You automate what you can to prevent that conversation from happening again

And that's pretty much it! If you do this over and over, effectively, I think you can build a great product and a successful business.

However, it's vital that you make the right decisions in this framework. Sometimes, feature requests should be ignored or put into your "someday" box. Sometimes, a small "Help" icon in your product that answers that same question you keep getting can save you hundreds of hours down the line.

Being able to code these small changes quickly is a superpower. Being able to make a change in 10 minutes based on a customer request feels almost magical for the customer.
February 28th, 2020
I took the last 3 days off (during the week) because I was hosting a friend in my hometown.

When I planned for this, I (naively) thought I would be able to squeeze in some work in the early morning or at night.

But I didn't. And the whole time I felt really guilty and had almost a feeling of withdrawal symptoms.

For me, I have a feeling of betrayal to myself when I take time off like this. I feel that for every "missed" day, that's important progress lost. I feel like I will have to make up that time, and now it will just take 3 days longer to reach my goals.

I also feel like I'm betraying my customers, sponsors, etc. What if they knew how much YouTube I watched or knew that I took the day off to go skiing? That time could be spent building a new feature or doing more marketing.

^^ I realize these thoughts are pretty ridiculous, but it's the truth.

I can't imagine that I'm the only one here. I can only think this would be even worse if you had a really tough boss you wanted to impress, or investors/mentors that had money on the line on your new company.

During my "time off", I legitimately had to step away for a couple hours and "catch up" with the business.

I told my friend to take a couple runs and I just sat in the car on my computer and caught up on email, etc. I literally sat in my car outside the ski resort and worked for two hours. How sad is that? After I got that work done, I didn't feel any better either.

And it's funny - doing this, I realized that almost everything could wait until I was back, and the sense of urgency I had was 90% in my own head. But it was less about emails piling up, and it was more about me feeling guilty that I wasn't working.

But it's not all bad, moments like these really help me realize what parts of my business rely on me, and that I need to continue to outsource/hire/automate so that it doesn't need me. I consider these to be "holes" in my business.

I also need to get better at planning time off. If I plan some time off in advance, it will actually inspire me to "get ready" for this time off and fix a bunch of things so that they can run without me. When I took 3 weeks off last year, I hired someone at Starter Story to manage most of the editorial process - they still run it and it has helped us scale so much.
February 27th, 2020
Today, I had a, no joke, near-death experience with moose.

I took the day off to do a 14-mile hike through the snow with my friend.

The hike is through Jenny Lake in Grand Teton National Park. Right now the lake is snowed over and looks like this:

Jenny Lake in Winter


Because the snow is so deep we had to bring snowshoes, which help you stay above the snow but also make you walk really slow.

When we got to the lake we started to walk around the perimeter to get to our destination of the hike.

While we were walking we noticed huge moose tracks in the snow. I didn't think much of this, since I've seen many moose in my life and it's never been an issue. I thought "Oh cool, my friend will get to see a moose".

As we walked along the moose tracks we also noticed smaller moose tracks. I assumed that was from a baby or child moose.

Keep in mind we are in the middle of nowhere and there is nobody else around for miles.

We kept walking further and further.

About 6 miles into the hike I look up and a GIANT moose comes quickly prancing around the corner. The moose is only about 200 feet away.

At first I thought it was awesome that we were finally seeing the moose, but then it stared us down. I've never seen a moose stare me down before - usually they barely notice humans or don't seem to care.

I told my friend to just stand still.

The moose started charging at us.

Then it stopped.

Then we quickly turned around and started hoofing it the other way.

We looked back and the moose was charging us again.

Then it stopped.

Then it charged us again.

By this time it was like 100 feet away.

I'd never seen a moose agitated like this.

Since we were in the wide-open lake, and had no choice of outrunning a moose, we decided to climb into the trees on the edge of the lake to get some elevation.

The moose created a perimeter around us and started "prancing" like a horse. I've never, ever, seen a moose do this or move as fast as this one was.

It was at this point we got this one photo:

you can see how fast the moose was running by how are its tracks are apart


^^ The way the moose is facing up there, that was the way back! The moose had crossed over to the other side and was preventing us from going back where we came.

Then, all of a sudden the moose was gone.

We kept going into the trees and thought we could go around it. Then, we look up and the moose was in the trees! Just staring us down! Just 60 feet away.

It was like a stare down / face off. We had nowhere to go.

We felt stuck, powerless, it was so fucking frightening.

I called my dad and the national park helpline in that moment because I had no idea what the protocol was for something like this. They told me to just chill and stand still, don't move.

We stayed for about 20 minutes.

Then, in a bold move, we decided to trek back onto the lakeside and just made a run for it (with snowshoes on).

We ran at least two miles in snowshoes as fast as we could, looking back every 5 seconds to see if it was behind us.

Eventually, we got out.

One of the scariest things of my life.

Apparently, more people are attacked by moose than any other form of wildlife, and moose attacks are increasing.
February 26th, 2020
Trying to squeeze in emails today and stay afloat, but got a friend visiting still.

It's always interesting to take full days off and *see* all of the areas of your business that somehow seem to run fine without you, and then some of the things that don't.

Obviously the goal is to get to a point where you are totally removed from the business, but it's actually helpful to take these days off to really see those.

Hoping to sort of get there by the end of the year. Also, this year, one of my goals is to do a "think week". I just need to get a few more things sorted before that, like customer support person for Pigeon...

My journal entries will be back (in full form) in a couple days, cheers.
February 25th, 2020
placeholder - check back soon...

- the real lessons behind it
- hubris on twitter (people really hate that)
- being the darling company makes everyone hate you
- give credit where its due
- angry mobs
- hit pieces
- jealousy
- being humble
February 25th, 2020
Got a friend visiting and I had to take most of the day off yesterday.

We went to these natural hot springs by the Snake River here in Jackson, Wyoming.

They look like this:

Natural hot springs


We were there for over 3 hours.

We saw a bald eagle about 100 feet away it was insane.

I need to take more days off and unplug. After I got back I had a million emails but they all could wait.

Taking the next couple days mostly off! 
February 24th, 2020
This weekend was a wash. I got my running in, and I kept up with my journal, but I really didn't get anything else done in terms of work/projects.

I usually work on the weekend, so the issue for me is when I *plan* to work on the weekend but then I sit around and procrastinate it...

So I feel guilty the entire time and also get no work done.... Lol. I should just take the weekend off if this is going to happen.

I'm actually taking the next couple days off (for the most part) since I have a friend visiting. Maybe it will help to refresh.
February 23rd, 2020
Sometimes, I hear people talk about how they are always tired.

Some memes:


^^ I don't know why, but I cannot relate to this.

I almost never feel tired. I've only taken a few naps in my life. I never fall asleep in movies, or on the couch.

I can't even think of a time where I passed out involuntarily (other than if I was inebriated). I think it has something to do with being neurotic - and definitely connected with anxiety and ambition.

When I started training for my first marathon a few years ago, I noticed something. Running and regular exercise gave me even more energy! But, a better kind of energy - more alertness during the day, and easier to fall asleep at night.

You would assume that running 20-30 miles per week would make you more tired, but it actually made me less tired - that was one of those realizations that changed my life, and my perspective on fitness/exercise.

Another thing I noticed - working on projects that I'm excited about give me more energy as well - that's obvious but imagine that you work on something you are mostly excited about all day every day.

That's often the feeling while working at a startup - I can work 12 hour days and it goes by in a flash - it doesn't even feel like work. And I can't wait til the next day and just want it to be the morning.

However there's a flipside to all this energy - it's really hard for me to fall asleep. It's always been like that for me, ever since I was a kid. I'm not diagnosed, but I probably have some form of insomnia. Over the years I've built a lot of "techniques" to fall asleep. The best one is listening to podcasts or watching The Office - really, really helps me fall asleep.

Some other things I've noticed that increase my energy levels:

  • Cutting back on alcohol, or partying less
  • Fewer meetings. For me, meetings drain my energy like crazy.
  • Less social media.

One of my favorite songs.

Disclaimer: I realize that I don't have kids to take care of, or sick parents, or anything like that. I realize that it would be a much different story if that were the case.
February 22nd, 2020
There's the ol' phrase: "It's not about what you know. It's about who you know."

It's very cliche, but I think as bootstrapped founders and people trying to "make it" on the internet, we can take some lessons from that.

I consider myself to be "self-made". When I think about something I want to do or accomplish, I romanticize the idea of "doing it all by myself" - this will always be a part of me, and it is a part of my identity. It's also probably the reason I failed at having co-founders and had more success as a solo founder.

However, when you look closer at very successful people and companies, you actually see that there is a whole network of people that helped make them successful.

I've got a couple examples.

1 - I used to work for an enterprise software company called Anaplan back when they were a Silicon Valley startup.

I had a customer-facing role and one thing I noticed was that most of our customers were also in Silicon Valley, and Anaplan was often a customer of theirs! For example, we paid a lot of money for DocuSign's product, and DocuSign paid a lot of money for Anaplan's product.

Now, that doesn't mean companies will be successful that do this (you still have to have a great product), but Anaplan is now worth $8B, their stock tripled in the last year, and they now have customers all around the world.

Sure, Anaplan could have gone with a cheaper e-signature product, but they had a strategic relationship with DocuSign, and it's hard to quantify what came from that (more customers, more word of mouth, important product feedback). DocuSign also went IPO and doubled their valuation in a couple years.

2 - Pieter Levels is probably the most successful solo founder I can think of. One thing I've noticed about him is that he truly gives back to the community.

He buys other maker's products, he sponsored the 24-hour startup with $500, he retweets stuff from people early in their journey. I can't really think of other people that do this. The only time you'll see this is from like VCs who are just RT'ing companies they've invested in. The difference between Levels is that he gives back with no expectation of anything in return.

Personally, I've been on the other end of his retweets and they have definitely contributed to my growth/sales/followers/etc. I look back at those moments as "defining" for me and I will always see Pieter as an element of my own success and influence.

And I honestly do think this kind of thing has contributed to his own success. I mean, it is the reason I am talking about him right now and think about every now and then.

You can call it selfish, I think it's beneficial for me to support other people even if I don't need to. Whether that's: 

  • buying an indie maker's product even if there's a cheaper/free version built by VC backed company 
  • writing a nice tweet about someone's product
  • sending a referral someone's way
  • jumping on a phone call with someone to give/seek advice
  • sending someone a message to thank, appreciate, or congratulate them
  • or even just a simple retweet.

Because I truly believe it will come back to you - maybe not today tomorrow or even this year, but I know that most of my "peers" online will be very very successful in the next 20 years. And if we can all keep propping each other up over the years, it will only continue to help us grow.

So, this year, I've made it a point to try and support more of my peers in the maker/startup/etc space. I'm still working on how to cultivate this, but I want to support more genuine people that are working their ass off.

And when you buy someone's product, do remember that it's already 40% off, because of taxes, ya know!
February 21st, 2020
Some of you might know my story, but I’m the founder of Starter Story. Over the past year, I’ve been working on a product called Pigeon.

I built this product to solve my own needs for Starter Story as we needed a CRM tool built inside Gmail to help us scale the business, and the existing tools weren't cutting it.

Anyways, Pigeon just hit $1K MRR, and for me, it’s been a pretty crazy and unexpected journey, and I learned a lot. 

DISCLAIMER: If you’re looking for a case study about how to grow a SaaS fast, this is probably not the one. This is mostly a look back at how I slowly reached 40 paying customers, what worked, what struggles I faced, and what I learned.

To be honest, I didn’t expect how hard this would be.

Why? Because Starter Story grew a lot faster and felt “easier” to get to that $1K revenue milestone in the early days. Building Starter Story was not easy by any means, but I thought that maybe my “success” at Starter Story would enable faster success at Pigeon - that wasn’t the case.

Not all revenue is created equal, and for me, building a SaaS was a new type of challenge and I feel like $1K is a good milestone to reflect! And not because it’s $1,000, but because it equates to about 40 paying customers, which feels like a lot (for me).

It also feels like a big milestone because I worked so damn hard to get here. Every customer felt like a big win, and every churn, lost opportunity, etc felt like a loss.

So, I wanted to write my thoughts while they’re still fresh and show you the real truth & honesty behind the last 10 months.

Maybe it helps someone out there going through a similar thing.


Very slow growth

Growth was a lot slower than expected.

I was able to launch the product to about 7 paying customers in May 2019. This is because I had built up a small list of people interested in the product.

This gave me pressure to launch (which helped me launch faster) but it also led to some overconfidence since I was able to launch with about $300 MRR, I felt like I was on top of the world!

But in the month after I launched (June), I only added 1 paying customer!! 1 CUSTOMER!! It’s pretty crazy to be working so hard on something and you only have 1 person sign up in 30 days.

And the next month after that? 2 CUSTOMERS!! Haha!


But this isn’t a pity party. 

In my opinion, having even just 1 paying customer is a blessing, or at least I kept telling myself that. As long as *one person* is getting value out of your product, there’s bound to be more, you just need to find them.

Churn is real and it sucks

I've never built a SaaS before, so I never really experienced churn first-hand. 

Personally, every churn felt like a gut punch, especially in the early days, when things were less validated and I associated the success of the product with my own self-worth (I do that less now).

It also hurt because I built close relationships with my customers. For 90% of my customers, we started out with a video call before they even purchased the product (more on that later), and often had many support chats and emails back and forth throughout the onboarding process.

Eventually, I got better at dealing with “rejection” though (mostly). Some things that help:

  • Often, churn is completely out of your control, and can be due to something happening for the customer, like their business idea not working/pivoting in a new direction, etc. 
  • Don’t assume anything and try to get the answers. When a customer cancels, knowledge is power. Try your best to learn WHY.
  • Be empathetic and put yourself in the customer's shoes - if they are churning because they aren’t getting enough value from your product - that can be an opportunity. When I lost customers in the early days because I didn’t have XYZ feature - now that feature is a selling point!

Discouragement and self-doubt

Mentally, I also went through some hard times. Not all bad though, but there were definitely some days... Being a solo founder certainly doesn’t help here either.

I got a YC interview that completely sidetracked me, and getting rejected from that felt like a gut punch because of all the work I put into prepping. I didn’t expect to get in, nor do I regret applying, but the interview process consumed my mind for a 2-3 week period back in October. Not much work on the product got done during those weeks, and when I look back at that "YC time" I remember feeling very stressed and unhappy.

In general, the “slow growth” got to me, at times. Compared to Starter Story, it felt like I was working double overtime to make a nickel.

But I did find some coping mechanisms for this self-doubt, here are a few:


The Google Security Audit == Direct sales?

I’m not going to go into much of the minutiae of the Google security audit, but I didn’t find out about it until right before I launched.

Basically, this Google audit would force me to pay $15K+ before I could even launch and validate the product. This was another gut punch, and this bullshit initiative by Google consumed my mind for way too long. 

But I found a workaround.

Before paying this egregious sum, you can have an “unverified app” with up to 100 users - and stay unverified.

One issue - anyone authing to Google would get a massive error screen that looks like this:


I could make this work, but I had to accept a couple of things:

  • I could only accept paid users, would have to charge a decent amount, and could not have a freemium plan (because of 100 user limit)
  • I would have to convince people to click through this danger screen, as nobody would sign up for Pigeon on their own accord if they saw this warning.

How to get around the danger screen issue? Direct sales. I would do a Google Hangouts call with every new prospect to learn more about their use case and give them a demo. Once they agreed they wanted to try the product, I would explain to them the unverified app situation and hopefully still make the sale.
 
The calls were extremely time consuming, and often led to no sale (or even no shows), however, I think this may have been a blessing in disguise. I learned a lot about direct sales, customers, the market, and even made some personal relationships with my customers. And the product has made some massive improvements over the months.

However, I would just like to say that I think it’s ludicrous how Google has set this whole security audit thing up. In my opinion, this will kill innovation and indie developers will simply choose not to build apps on Gmail's APIs. If anyone has questions about the Google security audit - feel free to reach out.

What Worked


I hope that some of the stuff above here helps other founders. For me, the mental side of things were my biggest lessons learned.

But let’s talk about what worked:

Building an email list and constantly announcing new things

I've built up a small list (about 500 now) of people interested in Pigeon. I collected the emails pre-launch and through the website/Chrome extension.

Since the email list also includes active customers, I do weekly feature and product announcements to that list. 

This does two things:

  1. Announces new features to active customers
  2. Announces new features to prospects that might be waiting out for that feature, or just generally on the fence.

I try to send a newsletter every week, and my feature cycle started to groove with that. It actually acted as a nice productivity boost.

People love to see that you’re actively working on the product and improving it, whether that’s prospects or customers.

Every little thing (whether it's a new feature, blog post, or customer testimonial) is an opportunity for marketing! I also would take the email announcements and put them on Twitter as well.

Example newsletter from this week:


Talk to customers (not what you think)

Ah, the good ol' generic startup advice: "talk to your customers".

This doesn't mean you need to call your customers on the phone or meet them at coffee shops. Just put a chat popup thingy on your site and chat with them over email - it doesn't even have to be about your product.

For me, the chat thingy has been huge. It's served three great purposes:

  1. A great way to take support requests, feature requests, ideas from existing customers and also have a personal conversation with them. I try to see every customer chat as an opportunity to learn something or at least provide some great customer service.
  2. A great way to chat with prospects and learn about new use cases, feature ideas, where you might need more documentation, etc. I’ll even make a sale every now and then.
  3. If you can answer the chats from prospects quickly, it shows that you have good customer support and that you simply care about your customers. As a prospect/customer, it’s kind of cool to get a response from the founder rather than some generic support bot.

Direct sales

I talked about this in the Google audit section, but Google essentially forced my hand into doing direct sales.

Because I couldn't have people sign up on their own, I would collect emails as a "request access" call-to-action on my landing page:

Landing page before the Google Audit was complete

Once I got their email there, we would have a small chat over email, and then I would ask them if they would be willing to jump on a 30-minute meeting (through Calendly) and have a face to face video conversation about their use case and give them a demo of the product. 

I got this idea from Superhuman (kind of) as they require an onboarding video call session for every new user.

I did this "direct sales" method for the first 6 months. At first, I was a nervous wreck for these calls. But after about 10 of them, it was easy and natural.

These calls were not always successful. Sometimes nobody would show up. Sometimes people would say they'd buy the product, but never actually commit. However, these calls were invaluable in understanding my customers, building personal connections, learning how to sell, and to validate the product.

Quora

I have a lot of customers tell me they found me through Quora as I did a bit of posting there in the early days.

This was great, not only because it brought in many customers, but because it meant people were actually searching for the solutions Pigeon offered.

Great customer support

When I interview founders at Starter Story, I always ask how they keep customers and grow their business.

A common answer is to “provide great customer support and customer experience”. When I heard this, I never actually believed that support could lead to growth, but now that I'm on the other side, I can see that it can!

Customers really do appreciate great customer support and it does go a long way, and it may be the difference between someone picking your solution over another.

If you check out our ratings on the Chrome web store, you can see a lot of reviews talk about me and the care that I put in the product and customer experience.


I know this isn’t scalable forever, but it’s one of those things that is super easy to get right.

What’s next

Now that the whole Google debacle is settled (I’ve completed the audit) and we added a free trial, things *feel* like they are picking up.

In the past 4 weeks, MRR has gone up 40%, and while in the first month I got one new signup/month, nowadays I’m seeing more like one signup per day.

I recently came across this graph from Baremetics on how fast companies hit ARR milestones:


I wish I’d seen this before, because it really shows how much longer it takes to get from 0-10k ARR than $10-20k ARR. Although Pigeon's growth seems to be slower than the average, the recent growth I've experienced past $800MRR has been faster. This graph gives me confidence.

Over the next few months, I’m focused on delivering more features and improving the product as usual, and eventually launching a freemium version of the product. Stay tuned!

Thanks

I want to thank everyone that helped me along this journey - looking back it's amazing how many people I've met through this maker/Twitter/ProductHunt/IndieHacker community over just a couple of short years. 

Also thanks to all my customers (and ex-customers) who always have great feedback and ideas - the product has come so far since last May and that's only thanks to the feedback from you guys! 

If there's anything I can do to help you guys, please don't hesitate to ask.
February 20th, 2020
The obsession with "trends" is a bit strange to me.

Don't get me wrong, I think trends, data, and analysis are important - if you're an investor it's very important. If you trade stocks, extremely valuable. But if you're an entrepreneur, stay the fuck away.

While it may be valuable to look at trends when first starting out, you need to pick something to work on and give it 100% of your efforts.

Once chosen, I think it's best to consciously not look at new ideas until you've given your new one a fair shot. Any time spent looking at new ideas is time wasted on your actual idea and hurting your chances of being successful.

Trends and data will surface great info (to get started), but they can only tell you so much. Executing and being in the trenches will be the real tell for any business idea, validation, the market, competitors, etc.

Trends are exciting and I can understand why people get excited about it. But it makes me feel like shit when I see entrepreneurs talking about trends and data and not actually working on something. I think this obsession with trends is very harmful if you are an early founder or plan to be a founder.

So let's stop pretending like we're VCs and chatting around the water cooler about the latest industry trends.

(this is just my opinion)
February 19th, 2020
I wrote a whole thing and then lost it...

Don't have time to rewrite now, but this journal was about how it's easier to break up a large mundane task into small weekly recurring calendar events and chip away at it.

For example, if you want to reach out to 100 bloggers, set a calendar event on Mondays to do 5 per week. Each week, you'll get better at it and learn new things, too.

This strategy helped me get on a couple blogs this week (I want more businesses to come to us about sharing their story).

And the funny thing is, last week, I had no success. This week, we landed in two blog posts/Github repos. I will continue to do this every week now! It all adds up :)