How I saved my failing coffee shop in 2017

In 2016 I owned a failing coffee shop in NYC. After losing money on it for almost two years I was ready to call it quits. Right before shutting it down I decided to throw a hail mary and do something drastic. It sounds unbelievable but this one change made it profitable practically overnight and completely turned the business around...


First, you might be wondering... Why would someone wait two years to shutdown a business that was losing money? Well for one thing, I was an idiot. This was early on in my career as an entrepreneur and since I had already been successful I thought everything I touched was going to work. I was wrong.


This coffee shop was not my primary business. My primary business was an adventure travel company I owned that was doing quite well at the time so I was using profits from that business to cover the losses on my side businesses (big mistake - I'll share more on this another time).


I talked to the manager who I had hired to run the cafe and told her that I couldn't sustain these losses any longer and it was likely all over, but before we did I wanted to try one last thing... She knew her job depended on it so she was game to try it. We launched an unlimited coffee subscription for $49/mo. All the coffee, cappuccinos, lattes, cold brew, tea, etc you could want for one low monthly price.


For context, normally we charged $4.50 for most espresso drinks (give me a break, it's NYC) so someone who was buying one per day 5x per week at $4.50 was spending $90/mo and some folks would even buy multiple per day. Needless to say, I was terrified to try this...


Keep in mind by this point it was early 2017 and no one had really done this before. I believe now there are a few brands out there doing membership coffee/drinks, but at the time it was mostly unheard of.


There were only two rules; you could only get one drink at a time and one per hour, that's it. Otherwise go nuts. Immediately something crazy happened... The signups started flowing in like crazy. First $1k MRR, then $3k then $5k then $10k and eventually we got up to $12k MRR at the peak of the membership program.


But what was even crazier was that our regular monthly sales didn't drop. I was certain this membership would cannibalize our regular sales. IT DIDN'T. Why? We just had more customers overall and more people buying extras like pastries, drinks, sandwiches etc. Once the word got out we basically stole every customer from every other coffee shop in a 3-4 block radius. Think about it... A coffee shop with a moat other than brand moat? It worked!


It ended up adding $10k MRR on top of our regular sales, which was exactly what we needed to save the business. I ended up keeping the coffee shop for another 3 years until 2020. Once 2020 rolled around I saw the writing on the wall and figured it was time to finally shut it down.


So why am I telling this story? First because I've never told it before. Only to a few people over drinks. But the real reason is because this story is the reason we switched Job Boardly from saas subscription pricing to one-time payment. Job Boardly was doing fine with modest growth but nothing too special. We liked it, but we didn't love it. We were suffering from "grass is always greener" syndrome. That's when this story popped back in my head. Let's do something BIG. Let's be completely different from everyone else. Why the hell not. We're still early on enough that we can afford to experiment. We switched from $49-$99/mo to $297 one-time payment. And guess what? It worked again.


The business became instantly more profitable and we're having fun again. I'm not saying you should go and do something drastic for the sake of doing something drastic, don't do that. I'm actually not saying anything at all, only sharing my experience. However, if you find yourself at the same cross roads I found myself at before calling it quits or convincing yourself that there's something better out there. Ask yourself how you could switch things up. Be as creative as possible. There isn't one way to build a business or price a product. Give yourself permission to experiment.


I was able to find our old Stripe metrics. We ran the daily sales on Square so what you see here is just the subscription revenue.

Mystery man made me tens of thousands of dollars

I did a text interview on IndieHackers.com with in 2017 ​

What came out of it improved my conversion rate for years to come... ​

First, some background -- It's a little cringe for me to go back and read but still some good nuggets in there. At the time I was 29 and my travel business was doing $125,000/mo. ​ I had no idea my life and my business was about to come crashing down on me one year later (I'll tell that story another time, it's a doozy). ​

From the article:

"First think about how you're going to distribute your product, then work backwards from there. ​ I borrowed $10,000 from one of our largest vendors, who had a lot to gain by helping me create Sourced Adventures [my former business]... ​

Within a couple months I'd sold 5,000 tickets to our first ski bus trip [...] The cash from that first season pretty much gave me enough to keep it going from there. I had no idea it was going to work. In fact, I was pretty sure people would not be interested since we had no reputation online." -- ​

Here is the full article: https://indiehackers.com/post/identifying-consumer-demand-before-building-my-travel-service-73l8NFmUIyOnmoJo42Nj… ​

What happened next was very lucky and gave our conversion rate a big boost... ​

The article ended up on the front page of Hacker News for a couple days ​ (separate thing but several people tore my website to shreds in the comments which is still one of my favorite bootstrapper moments to this day) ​

https://news.ycombinator.com/item?id=14763831… ​

Suddenly I received a mysterious email from an anonymous gmail account. ​

It said, "hey I saw your interview on Indie Hackers and I have some advice for you. Can I give you a call?" ​ At first I thought it was spam but it was juuust mysterious enough that I had to see... ​

I jumped on the phone with this stranger and he told me that he used to be the head of growth for one of the largest travel websites in the world. I won't say the name here but think of one of the biggest online travel sites that everyone knows and uses, it was one of those. ​

He told me that one of the things he spent a ton of time testing was the call to action for the book button. ​

He had tested this over hundreds of millions of sessions and said of everything that he tested "Check Availability" was the highest converting call to action. ​

I had no way independently verify this as he prefered to stay anonymous and wouldn't give me his name. ​ But for some reason I believed him. ​ I checked the site he claimed to have worked for and indeed every book button was "Check Availability" rather than "Book Now" or something else. ​

I immediately went and changed all of our CTAs and sure enough our conversion rate popped. ​

He was right! It worked! ​

I'm trying to improve my "building in public" skills... It doesn't come very naturally to me yet but when I think back on stories like this it just goes to show how much good can come from putting your work out there or increasing your "luck surface area" as they say. ​ In this case I would have never received this anonymous tip had I not shared openly. ​

There is obviously a flip side to this as well, as we all know, but deep down I feel it's worth it to put your work out there into the world and see what comes back to you. ​

Lastly, to my mystery man from 7 years ago... If you're out there and somehow you read this post I just wanted to say, thank you sir!