How To Avoid My Business Mistakes


The final text was sent. I lowered my head  and let out a long sigh.

Looked up at my wife and said, “It’s done…”.

I had just shut down the business I had started almost 2 years ago called Samson.

For those of you who don’t know, Samson was a service that allowed Barbers to manage their schedule through text messages.

Samson started out as a typical mobile application before pivoting into something else.

Now it’s shut down.

I’m not saying this because I want pity. I’m not trying to contribute to the vast amount of “failure porn” on the internet.

I’m writing this as a reminder, mostly to myself, about what to not do during the next time at-bat.

How To Avoid My Business Mistakes

Here’s a list of everything I did right:

  1. Quickly Moved From Idea To Execution – didn’t get slowed down or procrastinate with long list, business plans or anything like that.
  2. Attempted to Market From Day One – attempted to get the word out before the product was even built.
  3. 7-Day Startup – had some revenue within the first week.
  4. Knew My Target Market – knew who I was trying to help and had a general idea of how to find them.
  5. Cross Industry Innovation – attempted to bring innovations from other markets into a less “sexy” one.
  6. No Worries About Vanity Metrics – Tracking things is good but not everything that people tracks matters.
  7. 100% Bootstrapped – didn’t try to raise capital or take out a loan. Spent less then $50 dollars to set everything up.
  8. Kept My 9-to-5 – Stayed at my current job the whole time and didn’t think about leaving before having another option.
  9. Did Business With Friends – knew the first customer personally before launch. My wife also helped my at times with the business.
  10. Wasn’t Afraid To Pivot – Wasn’t married to my original idea.


And a short list of what I did wrong:

  1. Problem Wasn’t Painful Enough – the problem I was trying to solve wasn’t painful enough for potential customers.
  2. Didn’t Jab Before Throwing Right Hooks – Didn’t build an audience while building the product.
  3. Tried To Run Before Walking – Wanted it to be a product but probably should have just built out the service first.
  4. Didn’t Hustle Enough to Get the Word Out – sometimes the hardest thing to do is just to ask the first question.
  5. High Technical Learning Overhead – Tried to build a software product while learning a new programming language and new coding framework.
  6. Didn’t Talk To Customers Enough.
  7. Low Interest In The Industry – I wasn’t in the target demo and didn’t really want to be.
  8. Worried Too Much About What Others Would Think.
  9. Too Much Time On The Website – was thinking about a/b split testing, hosting providers, and design before I had 10 customers.
  10. Didn’t Stay Disciplined – For me it’s better to work 10 minutes every day on something then 2 hours once a week.
  11. Focused On The Little Things – I worried about things that didn’t matter that much at the beginning.
  12. Didn’t Cut Bait Early – In a way ending up doing this twice, the trending in the right direction. The first time 12 month before the pivot and then 6 after.

That’s the short and sweet version of the situation.

Less list are in no order of importance. Some of my wins and losses were bigger than others, but the net result is still the same.

Just remember to try to do more of the things in the “right” list and less of the things in the “wrong” list.

Even a mistake may turn out to be the one thing necessary to a worthwhile achievement. -Henry Ford

Alright so you can leave now, but if you want to stay for the full story continue on.

There’s Already An App For That

The idea for Samson come to me in October 2015 but I should probably back up a bit more. By a bit I mean almost a full year. Let’s head back to 2014.

My barber, let’s just call him John, was complaining about the scheduling apps on the market. There wasn’t one specifically built for barbers that he loved, because the user interface on most scheduling apps was overly complicated. John just wanted an app that was sleek and simple.

My ears perked up when he started talking about this pain point.

I felt like I was on a gold mine. Here I was talking to a business owner who had a simple problem that no one was solving well.

To boot John was willing to pay money for this solution. In fact he already was paying a subscription for another app that was about $30 a month. So being a Software Developer I promised to build the scheduling app he always wanted. Who wouldn’t want something like that?

So the plan was set in motion. I was going to build a mobile scheduling app with a clean and simple UI, specifically tailored to young barbers.

Did I know anyone else in the industry? Was there others with the same problem? Seeing that other scheduling apps where in the app I decided yes.

Naturally I went home and started coding (Tried To Run Before Walking). I decided to build the application using AngularJS as the programing language, Firebase as the backend and Ionic as the front in framework (High Technical Learning Overhead).

After I was ready to hand over the code. What happened? John didn’t like it (Didn’t Talk To Customers Enough).

Can advertising foist an inferior product on the consumer? Bitter experience has taught me that it cannot. On those rare occasions when I have advertised products which consumer tests have found inferior to other products in the same field, the results have been disastrous. -David Ogilvy

The app which I was tentatively calling BookingBlade was a step in the right direction but needed A LOT of work. I have code in a private repository on Github, but I’m embarrassed to show it. Maybe some day it will see the light of day.

Ok that’s fine I could make those updates, but after weeks of “hard work” I was starting to lose interest in the project (Low Interest In The Industry).

The one saving grace was that every few weeks I would need a haircut and have to go see my barber again. It was these short moments that would launch me into fits of coding, just to have something new to show during my next cut. Sadly, right after the cut I would take a break that extended weeks until my next cut was up (Didn’t Stay Disciplined).

In the end I felt like I was just building another “Me Too” application which I was. What’s worse is that it took me 12 months on and off before trying to change things up (Didn’t Cut Bait Early).

The Pivot

So I was listening to podcast, something I do almost everyday, and decided to steal the Productized Services  idea from the guys over at the Tropical MBA Podcast.  I was thinking that I could turn my barber scheduling app into a service. Things were starting to brew in my mind, but didn’t get fare.

Later on I came across the ideas for an invisible app from this article in TechCrunch article, The Burgeoning Invisible App Market.

For some reason things just clicked, I wanted to create an invisible app that allowed barber to manage their schedule via text messages.

All a pivot is is a change is strategy without a change in vision. -Eric Ries

So I started doing more research, because I wasn’t sure if it was even possible technology wise. However I started finding all kinds of things.

A lot of inspiration for the pivot was found by copying pieces from multiple application in this list of invisible apps on Product Hunt. Seeing that a few invisible apps have first names as product I decided to steal from that also. Which brings me to the name of the new business… Samson.

At first I was thinking of the biblical story of Samson and Delilah, Samson was too busy try to get you scheduled for a haircut that he didn’t have time to cut his own. However I quickly discovered Samson from Half-Baked after first contact with Barbers and people in the industry. Either way I spent too much time on naming (Focused On The Little Things).

So I pivoted, and yes things got better.

A Quick Ramp Up That Stalled Out

I hit the ground running… 10 days after thinking of Samson the site was up with an email capture form.

3 days later, John had paid and signed up for the service. This was my first online sale ever. Definitely a personal milestone.

Success is a lousy teacher. It seduces smart people into thinking they can’t lose. -Bill Gates

A second barber signed up two months later, and a third barber signed up four months after that.

Won’t go into all the details, but it was very difficult to get new barbers to sign up. In the end it’s probably because the problem I was trying to solve wasn’t painful enough (Problem Wasn’t Painful Enough). It could also be that I wasn’t able to properly communicate the value of the service (Didn’t Jab Before Throwing Right Hooks).

I tried multiple channels to get reach out to new barbers. Twitter, Instagram, Email, Cold Calls, etc. One thing I thought was asking friends and family for introduction to their barbers, but I never pulled the trigger (Worried Too Much About What Others Would Think).

I think you’re getting the idea. Things started up fast but plateaued very quickly.

After doing a lot of thinking I came to the realization that this wasn’t the type of business that I personally wanted to run. Which lead to Samson eventual demise.

Feel Free To Take This Idea

Steal like an artist. -Austin Kleon

Here’s the rub. In the next 12 – 24 months a newly launched mobile first scheduling app for barbers could have some legs. It’s just an idea at this point, and without the right execution it won’t work. Trust me I know because I tried to execute on this idea during nights and weekends and I wasn’t good enough. I stepped in the ring the market punched me in the face.

That doesn’t mean it couldn’t work for you. Take this idea and run with it.

Long term “invisible app” will become the new normal. The idea of messenger bots already starting to trend. Even though Samson was human powered, the main vision was to get to the point where it could be 80, 90, even 100% automated.

I can see a day where the main interaction with a device is through something like Apple’s Siri, Amazon’s Alexa, or the Google Assistant. Whether that’s in voice or written form has yet to be decided. All and all “Dumb AI” is already here and it’s not going away.

I’m not 100% sure what I’m going to do next, but hope to learn from this experience fully. I hope you’ve learned something from my mistakes also.

Have you had any recent missteps let me know in the comments below?

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