Things that didn’t work

8 complete failures and a few things learned along the way.

I’ve always found the way the startup community talks about failure to be a bit odd. I absolutely agree that a healthy outlook on failure is great. In fact, it’s been required during my life as I have tried a lot of things that haven’t worked. I hope we all know by now that failure is not the end of the world and life does go on, yadda yadda. However, a re-brand to “a learning experience” is too much for me.

Personally, I’m totally OK with calling something a true, 100% certified, undisputed failure. I feel a deep need to recognize and own all of my failures. I’ve found that applying the “failure” label to something helps bring closure. Calling it a “learning experience” feels a bit too fuzzy. It’s as if there’s still a sliver of the door still open inviting you to jump back in and apply what you’ve recently learned to turn it all around. Nah. For me, a failure means it’s the end. It was fun while it lasted but we’re done here.

That hole wasn’t always there…

Now that doesn’t mean things weren’t learned along the way. Things are always learned but that’s a part of life. I learn things doing mundane shit all day. Yesterday, I learned that my cat has been eating the bottom of one our living room chairs. He’s eaten most of it actually. Now, I learned that while cleaning. If asked what I had been doing all afternoon I would have said cleaning, not learning. I see failure the same way. You can learn things along the way but things either end in success or failure.

In honor of failure, I’ve recently been wanting to list out a few of mine. Specifically, a few ideas I chased while a student or as a side hustle. The list is wide and varied. I’m embarrassed by most and definitely think some could have made me a Bezos but we’ll never know. I’ve paired some learnings with my failures but please do not be mislead! These are painful failures 💀 .

For each idea I’ve decided to share when I began working on it, how it developed, how it died, and some quick learnings. These are not meant to be full lifecycle stories. I’m sticking to the cliff notes.

We’ll kick the list off with the undergraduate era. I studied Industrial Design in Boston and the following ideas were my first foray into the software world…

Let’s Play mock ups for a pitch deck (ha)

Let’s Play

When: 2008

Problem: Difficult to find a pick up soccer match in Boston as a student.

How it began: As a freshman in Boston I wanted a way to find pick up matches over the weekend because everyone needs friends! I had tried Craigslist and Facebook but it was always a bit of a mess. I had this idea of creating an app that allowed people to start a pick up match and invite others to claim each position. Once all positions were filled on both teams the game could be scheduled at a location nearby to everyone. I built mockups in PowerPoint and showed people on my iPhone 3G. Yea, it was a while ago. Over two months I showed it to roughly 600 people — easy to do when you’re in school. Feedback was strong and it seemed like I could expand to other sports really easily. I hooked up with a few local CS students to make an early prototype and we had a beta version of the app within a month.

How it failed: From day one, maybe even hour one, we tried to expand too quickly. We wanted to connect people trying to start bands, set up soccer matches, play chess, do yoga, or any other activity under the sun. The UX was confusing and it seemed like we had no real core user we were solving a problem for. In hindsight we could have solved this problem by simply narrowing the focus of the app. Unfortunately, we didn’t think of that. I was so set on it being the “connect with someone to do anything!” place that I didn’t see the narrower yet stronger opportunity in front of me. Bummed I couldn’t make it work for everyone the “company” fizzled out after about four months of effort.

Learnings: Don’t try to be everything to everyone. Find a user you can really serve and conquer them.

Not my image


When: 2009

Problem: Finding a date as a student is time consuming.


How it began: Got dumped by my now fiancé (true story) and dating was a new world for me at the ripe age of 19. Being a nerdy student at the time the idea of fending for myself in a sweaty and loud college bar in Boston seemed pretty unbearable. Still does. The goal of Let’sGrabPizza was to know who was up for grabbing dinner on a Friday night around me. Hopefully, one of those people would be a lovely single lady and love would follow soon thereafter. I printed flyers and effectively tried to start a Meetup for singles that loved pizza. Pretty tragic stuff. After nobody attended I pitched an online version to the same crew that helped me build Let’s Play and we were off. We built a quick Wordpress site and shot it around to friends. You could submit your name, Facebook profile link, and pizza preference. We would then manually match people on Facebook info (interests, location, relationship status, school, etc) and, of course, pizza preference.

How it failed: Sh#t was creepy. Unsurprisingly, young college students didn’t want to beg for dates online. Our society had yet to break that dignity barrier it seems. After spending about a month tweaking the site we decided to bail. The feedback survey’s were extremely poor and it seemed like we didn’t have an experience that could compete with simply meeting people at a bar.

Learnings: We didn’t know how to communicate our service or who to communicate it to. During the Let’s Play saga we struggled with telling too big of a story. With Let’sGrabPizza we didn’t say enough because I think we thought the appeal was so obvious. Main learning here is to really think about the story you want to tell and help people achieve that a-ha moment.

Really wish I had an example of the site. It was a beauty.

Random note: Not sure why I was so into the “Let’s<<insert something>>” naming model. Thankfully ditched that moving forward. 🙏

Kinda miss the Industrial Design world 😭


When: 2011

Problem: Honestly, there was no real “problem” that inspired this one. I thought it would be a cool idea. However, my best attempt at summarizing the opportunity would be to give kids the Tamagotchi experience with real plants.

How it began: I worked on this concept as part of a school project that tasked us to create a product we could 3D print. The Gru would give kids a way to grow a small flower in a portable pot and then trade it with their friends. Ideally, it would teach kids about the earth, looking after things they own, and help them be social. I printed a few versions of it and sent it to family and friends who had kids. The initial feedback was really strong. Kids loved playing with it and parents appreciated what the product was trying to teach them.

At this point in world history Kickstarter was the place to be if you had a physical product startup idea. Outside of class, I worked on building a campaign and set a goal to launch before Christmas holiday.

How it failed: Before publishing my Kickstarter campaign I decided I needed further research to pad my campaign. Unfortunately, during my research I found that kids weren’t sharing or swapping their pots. Almost every kid that I gave a Gru to left it at home or lost it. Thinking about the core actions of my product, swapping them was top three. Losing it was definitely not up there. Seeing how quickly kids forgot about the product wedged doubt into my mind and the project lost steam. I iterated over the next couple of months but the excitement had been drained. Once the class finished the idea died.

Learnings: Define the core actions of your product and ensure they are completed. If your user only does a quarter of what you hoped they would you probably don’t have a product they are willing to make a part of their daily life. Also, be wary of making a product for a user you know nothing about. It’s hard to literally and metaphorically put yourself in a kid’s shoes.

The following ideas were worked on during graduate school. I was lucky enough to meet a group of like-minded individuals at Carnegie Mellon and we started the “Masters of Product Development Startup Group”. The crew was Kevin Brown, Raphael Bouchard, Ross Woodworth, Tomas Alvarez, and Hannah Kim. They’re all doing very cool stuff now.

BOMB logo 💣


When: 2012

Problem: When taking a Jaeger bomb the shot always whacks you in the face and it hurts.

As a user, when I’m taking a jaeger bomb I want the shot glass to stick to the bottom of the glass, because I can’t afford dental work at the moment.

How it began: I’m not sure where this idea came from within the group but it became popular very quickly.

We used the house Kevin and I lived in as the startup war room. The Jaeger bomb idea was the first of many, many ideas we’d work on there.

Since the group had a mix of Industrial Designers and Mechanical Engineers we quickly made a few mock ups to have something to test. It was effectively a normal beer glass with a magnet welded to the bottom that would hold a metal shot glass in place when you took a Jaeger bomb. We made a few prototypes and did some incredibly serious user research. Research in the form of throwing parties at our place and distributing questionable amounts of booze.

All participants were 21 years or older.

How it failed: It really wasn’t a problem and Jaeger bombs aren’t that popular. Our business model was to sell cases of the glasses to bars and within our own online shop. After speaking with a few bars we quickly found that nobody wanted to pay for a premium glass to serve a rarely ordered drink. Additionally, drinkers thought it was cool but not amazing. We quickly realized that at best, our product was going to be sold in the gag section of Urban Outfitters. After a few weeks we packed it up and moved on.

Learnings: Sell pain killers not vitamins. We created the perfect solution to a problem that didn’t really exist. Additionally, during our development we focused entirely on the drinking experience (shocker). We ignored the bar owner perspective and that proved most deadly.

No clue what the explanation text is attempting to explain.


When: 2012

Problem: There’s no way to get an understanding of the crowd at a bar before going there.

How it began: The area around Carnegie Mellon has very limited bar options. Very, very limited. Silky’s, our local, barely had lights. It did have a great G&T for <$5.00 though. Anyways, when thinking about where to go out at night we wanted to chose wisely before making the haul into the city. We realized that we didn’t have a way to understand how packed a bar was or what the crowd looked like before getting there. We set out to solve that by making an app that allowed people to check in at bars and rate the current status of things. Checking in would get them a drink and we’d help bar seekers find their way to a watering hole that met their needs.

We set out to do research on the eve of Halloween. You can see me interviewing a foxy school teacher, a grateful dead band member, and a saucy sailor above. The user research was proving successful. Seemed like everyone we spoke to wanted to know what a bar was like before getting there.

How it failed: We quickly found that the crowd and demographics of a bar had little impact on your selection. Most people care more about who they are going to a bar with than who they are going to encounter. Also, most of our research revealed that the main use case was for guys to discover bars that had an abnormally large amount of single women packed inside. As you can expect, we weren’t all that interested in solving that problem and so we left this idea behind after a month of work.

Learnings: Before setting out to tackle a problem, define what your goal is. Our team was swayed too easily by our research because we didn’t have a strong vision. Additionally, be careful doing research with people who will simply confirm your ideas. We didn’t push hard enough to find users that weren’t all that interested in our idea and that gave us a lot of false-positives.



When: 2012

Problem: Restauranteurs struggle to sell meals during the week day.

How it began: After moving away from Buzz and the B2C world, we wanted to try something B2B. Inspired by a trip to a local burger joint, we began to wonder how a restauranteur could fill their restaurant when everyone is at work during the week. We spent a few weeks picking apart different parts of the problem and arrived at a simple opportunity: people may go to a restaurant during their lunch hour if it’s easy and affordable. With that hunch in mind we set out to arm restaurants with an app that allowed them to create lunch time deals. We designed an MVP and showed it to a number of local spots around downtown Pittsburgh. After the initial round of research we set out to begin building our beta.

How it failed: This idea never saw the light of day. We worked through it and got the app to a point where a few local restaurants could give it a spin for feedback. At the end of the day, restaurants were tired of having to give discounts to get people into their doors. Additionally, our app didn’t tackle the biggest issue for the restaurant goers which was having to get to the restaurant in order to take advantage of the deal. We killed the idea after about two months of work. It’s no surprise that food delivery services are so popular now.

Learnings: We never took the time to truly understand our user. We saw an opportunity where technology could wedge in between two different parties and charge money doing so. Poor user understanding and weak business value killed Kiwi before it even began.

Mailo Landing Page v1… WOOF


When: 2012

Problem: Once a month I was driving from Pittsburgh to New York City and back to see my family. The trip typically cost $200 and as a student that was a ton of money. During one of my trips I began wondering how I could make money off my long drive.

How it began: After reaching New York City during one of my monthly trips I immediately began creating a quick site that linked to a delivery request form. The site displayed the route I was driving each month and allowed people to submit requests to drop stuff off along the route. Users would punch in their name, the pickup and drop location, what the thing was, and how much they were willing to pay. I printed out some flyers and hung them in the local Giant Eagle (grocery store in Pittsburgh) to drum up interest. Over the next few months I received close to 60 requests to drop off a wide variety of stuff. Stuff like cabinets, moving boxes, bikes, people(!), and pets. Imagine picking up a random person in your own car and delivering them somewhere. Crazy idea 😅.

Over three months I completed a few deliveries and documented the process. It was exciting to actually go through with a delivery. I took cash and those three deliveries were effortless. Convinced this could be a big idea, I spent my holiday break rebuilding the site and mapping out the product roadmap.

How it failed: The tech required to pull off the idea was more than I could handle. To really pull off the idea I needed to map my trip, allows users to pick a spot for pick up and drop off, describe their item, manage the space in my car for multiple items, track drop off progress, check items to make sure nothing was dangerous, take payment, check the shipper wasn’t a known criminal, etc. It quickly became a huge product that well surpassed my amateur coding ability. Quite honestly, I reached a point where I was extremely intimidated by the idea and was unsure if people were going to be willing to trust that random people would safely deliver their stuff. After a few weeks of debating the idea internally, I lost confidence and let the idea lose steam.

Learnings: At this point in my life, I had not yet developed the confidence to take the plunge into an idea. Mailo felt good and the early engagement suggested that maybe, just maybe, something was there. Could it have been successful? Who knows. Probably not. However, I never pushed hard enough to see it through and so this is the only idea I truly regret bailing on. Main learning here is to map out what success may look like prior to starting on an idea and if you start seeing things form have the guts to make it happen.

We’re now entering the side hustle era. I worked as a designer at IBM and the following idea was my first part-time effort…

StreetStyles Landing Page and Shopping UI


When: 2013–2014

Problem: Putting together a cohesive outfit is tough and the traditional shopping experience doesn’t make it easy to shop by “looks”.

How it began: I like to dress well. Not loud or super fancy but I like to dress thinking that I could meet the president, martians, Jessica Biel, or my fiance’s parents randomly at any point in the day. In 2012 I was obsessed with the site The Sartorialist and my big idea was to make that site an e-commerce experience. Users could upload looks, other users could identify the items at different price points, and you could buy the full look in one go. I personally built the first version of the site (the Let’s Play and Let’sGetPizza guys wouldn’t answer my calls at this point) in three weeks. It was very rudimentary and relied on me uploading content (straight from the Satorialist) and sourcing the clothing options. In the early days it was purely a click through shopping experience — we had no shop of our own. This was the first time an idea of mine had proper usage. I launched the site and had about 1,000 visitors a month. Visitors were clicking through and commenting that they bought the items. The idea was working! Instead of continuing down that path I wanted to actually manage and store the clothes being bought. My goal was to own the full user experience. I spoke to clothing distributors and inked partnerships with a few. I began stocking full looks in my small apartment in Austin, Texas.

How it failed: After a few months of practically giving clothes away for free I had to shut it down. The costs were overwhelming and as a young professional I didn’t have, nor want to invest, the capital to sustain it. I shut down the site and sold the remaining clothes on craigslist.

Learnings: I never truly mapped out the costs of my idea and it was just too damn expensive. The costs of buying and storing the looks was immense and I didn’t have anywhere near the amount of traffic needed to empty my apartment of clothes. I failed to create a business plan before starting and unfortunately logistics, and my ignorance, killed this idea.

Final Thoughts

Reflecting on the ideas I’ve tried to build is pretty embarrassing. Most of them are boring and been done a bazillion different times. It’s no surprise they all failed. When I talk about this period of my life with others I like to refer to it as the “cover band” era. I had to try my own version of a bar finding app, restaurant deal app or clothing store site to get a feel for how I work. I was slowly learning how a startup could function and more importantly, how to properly approach new ideas. I hate to say it but I learned a lot along the way.

If I were to summarize what I took away from the cover band era it would be…

  • Make sure the problem you‘re trying to solve is a real one.
  • Perform deep user and competitive research before starting.
  • Understand and document all aspects of your business model before you begin.

I was lucky enough to take these learnings and apply them to a few successful endeavors. It’s easy to say the painful failures were maybe me needing to pay my dues. In any case, what I truly learned is that failure hurts. And if it doesn’t, you never really cared about the thing you were chasing in the first place.

Thanks for reading! I’d love to hear about your “cover band era” and the ideas that failed. Comment below 👇 to share.