3 Lessons From Failing My First Startup

3 Lessons From Failing My First Startup

About a year and a half ago, I heavily invested myself in founding my first tech startup, Yepic — a venture that ultimately failed. It was supposed to be an app for spontaneously finding things to do and finding people to do things with.


Screenshots of the Yepic User Interface

A Very Brief Background

Over the course of roughly a year, I recruited a technical co-founder, raised some money, built a small team of advisors, and hired a few contractors. Ultimately, at a tiny fraction of cost compared to most app startups, I got functional Yepic apps (with a UI I am very proud of) built for both iOS and Android — even though I’m not a programmer.

However, mid-way through my startup’s journey, it became clear I was more committed than my co-founder and we had a fallout. Following this turning point, I contracted other developers in attempt to continue my co-founder’s work and fix several significant bugs that were preventing Yepic from an official launch.

I hired three different developers, but after much struggling for each of them, they all came to the conclusion that my co-founder’s code was too messy to work with and that Yepic would have to be written from scratch — something that would take lots of money and time. My money, time, and motivation had dwindled to an all-time low. I realized without recruiting another skilled technical co-founder I got along with or without going for tens of thousands in new investment, the road ahead did not look good. Although I still believe in the potential of the idea, I decided to quit the project.

3 Lessons From Failure

I did many things right — but in the end, I failed at even getting Yepic to official public launch (though I did quietly launch and beta test this version with some bugs on the app store). Failure isn’t fun, but it teaches you a lot. Here are the 3 major lessons I learned from my failure.


1) Start small

Be minimalistic. Entrepreneurs often dream up grandiose visions of their app / website / business, and then spend tons of time readying their product — only to run out of money or to find out that there really wasn’t the market they were expecting. It’s important to begin with the end in mind, but trim down the features of your business concept or product to as barebones as possible — a Minimum Viable Product. (As an example, Yepic could have started as a social planing Facebook group — or just a simple iPhone app rather than both complex iPhone and Android apps). This will save you tons of time. It enables you to ship a product 10x faster, focus on quality of features rather than quantity, and quickly test a product’s potential. I really wish I had followed this philosophy more carefully.

Prove your worth. Anyone *good* willing to work with you (co-founders, team members, investors) will want to see you’re capable of skills essential to getting the startup off the ground. Before trying to woo others in, first do as much as you can on your own to show them you’re someone worth working with. I did a good job of this by lining up some investment, designing mockups, and building a static prototype. I should have done more though… such as building and marketing a large and active Facebook group or similar. The more you do alone before recruiting others to join you, the higher quality talent you will attract.

Fail as quickly as possible. It is best to launch your product super quick, get feedback, and then continuously iterate based upon what is working and what is not. Treat everything as an experiment. The sooner and quicker you fail and then improve, the closer you are to success. If you want to change the way people do things, do not hold onto a reputation of playing it safe… If you’re not willing to lose big, you won’t win big. Try big ideas quickly and see if they work before you waste a ton of time building something that doesn’t gain any traction (like I did). I even now apply this philosophy to friendships and dating (see this somewhat relevant Tim Ferriss article) — just make mistakes, break things, fix things, and go forward.


2) Invest in only amazing relationships

Find the right people. Choose to work with people who you love and who really care about the vision you have, not just the potential payoff. My technical co-founder and I probably wouldn’t have been good friends if not for the startup tying us together. I cared passionately about the mission of the startup whereas I think my co-founder was more interested in it because he just thought it was an idea that might take off. Startups are tough and take thousands of man hours, with lots of ups and downs… your early team needs to be compatible, persevering, and really believe in the vision you’re fighting for. (AirBNB founder Brian Chensky firmly believes in this concept and “looked through thousands of people and interviewed hundreds” before hiring AirBNB’s first engineer.) My co-founder and I were not the right fit, and our relationship ended up straining the startup instead of propelling it forward. Learn from my mistake here and only invest in amazing relationships that you feel great about.  

Go 50/50 — with a cliff. One of my Silicon Valley advisors strongly suggested I offer my co-founder 50/50 equity — and implement a cliff (which is SUPER important in case a fall-out does occur). He said, “it’s better to have a little of a lot than a lot of a little”. I totally agree with him now and really regret not following his advice at the time. I should have offered my co-founder 50/50 monetary (but not control) stake from the onset, giving him feelings of ownership and skin in the game. Instead, I valued myself as more crucial to the company which (right or wrong) set things off on the wrong footing and helped set us more against each other than together against the world. Evem though a 50/50 equity split is not always the right decision, make sure you do not come across as greedy when working with others.

Create accountability. Keep everyone accountable and on the same page regarding expectations and what happens if expectations are not met. Incentivize success. Part of accountability means having the discipline to make challenging decisions if objectives are not being met — and knowing this now, I should have cut my losses with my co-founder months and months before we eventually split. I should have also made sure he was accountable to creating clean code with notes so that another developer could take over if need arose — which it did. Create clear agreements with others that have clear consequences if specific objectives are not met.


3) Be a decisive leader

Deal with sensitive issues. Being a founder of a startup requires making many decisions. You will make good calls and bad calls. Don’t be afraid to make mistakes, but do be afraid of timidity and indecisiveness. You have to learn a lot “on the job” when forming your own company, but this should be no excuse for not making decisions confidently and bringing small issues to the table before they become big ones. When negotiating equity with my co-founder, I was really bad in wanting to keep pushing things off. A leader should resolve issues quickly and take initiative in making respectable win-win decisions, not be weak and avoid any potential conflict. I learned a lot here.

Know when to cut your losses. Sometimes the circumstances just aren’t right and you need to throw in the towel, for yourself and for those following and / or investing in you. You should be getting a certain amount of output for your input. Things started off great with Yepic, but really fell flat at certain point — even though an official launch day always seemed only a few bugs away (an illusion). Looking back, I should have cut ties with my co-founder much earlier than I did and I should have abandoned the idea of working with his code much earlier than I did. Some mistakes are less fixable than others. But other opportunities always exist and you can take what you’ve learned other places. Because I value perseverance as one of my strongest qualities and became so passionate about the project, this lesson (especially quitting at the end) was my hardest.


My journey has been a rough ride, but there is no doubt that it has been an amazingly valuable educational experience. I am very appreciative to everyone who has been supportive: my investment partner, advisors, friends, and Yepic’s beta testers. I may re-evaluate coming back to this project another time, if someone else has not already figured the spontaneous social planning space out. But for now, I am moving on to other projects.

I hope this post has been somewhat helpful or inspiring (failure is inspiring) — or at least interesting. My advice to anyone thinking of starting up their own company is… do it. Go, dream big, have fun, and figure it out as you along. You may or may not succeed, but even if you don’t, you’ll learn a lot — and you’ll be more prepared for the next time.


Thanks for reading and I very much welcome any thoughts or feedback below…
Mexico, Part 1: A “Dangerous” Land

Mexico, Part 1: A “Dangerous” Land

I chose to travel to Mexico – alone, with almost no Spanish skills, and with an unconventional travel philosophy involving hitchhiking and sleeping in strangers’ homes through Couchsurfing.

I was warned so many times not to do this, so choosing to cross the border was a big test for me of guts, persistence, and clear mental thinking. Some say I failed the mental thinking test, but I disagree.

Traveling Central America has been a goal for me several years now – in order to experience different people, cultures, and ways of life. And, despite quite a few odds and despite many people discouraging me (which happens for most of my best ideas), I am now on a journey that I have long wanted to go on. 


Why you should never, ever, ever go to Mexico

Now, being in Mexico for three weeks, I find many of people’s fears about Mexico humorous. I find it funny how people fear the unknown. I find it embarrassing how, before I left, I was scared. But I was scared. 

Why was I scared? Because when I started talking about visiting Mexico, people from all backgrounds and all parts of the USA made it their personal duty to give me every reason not to cross the border. For you to get into my initial mindset, here are 4 highlights that particularly gave me the shivers:

1. “You will get drugged, kidnapped, or beheaded by the drug cartels.” This is one of the most common conceptions about Mexico. A number of people found compassion within their hearts to show me brutal YouTube videos of drug cartels beheading and mangling victims in public and leaving them in the streets. In addition, I was told grueling statistics of how many tens of thousands (including many tourists) die each year from Mexican drug violence.

Some cartel members. Many cartel members in this gang are former police and military officers, and they are known to have a higher tactical degree than official Mexico police forces. Needless to say, police in Mexico have a strong reputation for corruption.

2. “You will be shot dead while walking in the woods or camping.” This warning came to me particularly alarming, mainly because the guy telling it to me was Mexican (one of the first Mexicans I ever talked to) and he also happened to be a United States Marine. He said, “If you go exploring around in the mountains, one of two things will happen: 1) You will wander onto private property and be shot dead. 2) You will wander onto someone’s marijuana field and certainly be shot dead.” I told him I had already bought a new tent. He followed up by laughing and saying “you got some big balls man,” a phrase, earned or unearned, that was to be heard many more times during the course of my trip.

An armed guy and a marijuana field. This would not be a good camping experience. 

4. “The culture in Mexico is animalistic.” People told me the Mexico culture is harsh. Even my uncle, who I deeply respect and who has far more adventure experience than me, warned me not to go to Mexico. “There is such poverty there. People there are animalistic because they lack the basic human necessities. It is not safe.”

My grandmother, one the master worriers of the universe and an ESL teacher for Spanish students, notified me of other horrors: snakes and vicious animals, extreme temperatures in the mountains, deadly viruses, and other miscellaneous Mexican travesties sure to kill me. She also suggested that I might die first by being hit by a car. “If the Mexicans hit you with a car by accident, they ram into you more until you are dead. This way they don’t need to pay your medical bills,” she said.

I was made led to believe that all Mexican people are evil vampires.

4. “Ariel, your Spanish is horrible.” This was probably my biggest concern. I took a year of Spanish in high school and briefly used Rosseta Stone, but that was all a few years in the past. Before heading to Mexico, I only knew around 20 Spanish words somewhat confidently. And most of the words I knew were pretty useless… like “hola”, “como estas”, “adios”, “gracias”, etc.

It would be one thing to have to deal with all the dangers listed above, yet quite another to have to deal with all of those dangers in addition to not being able to communicate. I imagined myself being trapped in dangerous situations, like being kidnapped by a drug cartel, and not even having a fleeting chance of talking myself out of trouble. What could I even say to them? “Hola amigo, como estas?” If I couldn’t win cartels over by friendship, maybe I could pull a “donde esta el bano?” and just make a run for it.

Assuming that I would not get immediately held hostage or die by snakebite, other questions remained. How would I buy a bus ticket to Mexico? How would I book a hotel room? If I went to to Mexico and miraculously survived, I would need to become a master of charades or learn the language very quickly.


Thoughts before Mexico: “Ahhhhh! I’m gonna die!”

Overcoming Fear of the Unknown

Was I scared? Was I nervous? Yes. When people from all across the United States nearly unanimously tell you that somewhere is extremely unsafe, you are inclined to believe them… at least I was, but probably not as much as the people who care about me hoped. When I told people of my plans – which are of course quite different than your average tourist itinerary – they gave me looks like I was crazy, had invincible teenager syndrome, or was just plain naive. 

As I traveled the United States and got closer and closer to Mexico, the warnings of others increasingly echoed in my mind. I seriously considered not going or at least finding a travel partner to go with who could speak Spanish. I searched for an impromptu travel partner for a week, but nobody was available or crazy enough at the time. (Now I am glad I am traveling alone now, though).

” HA-OOH! HA-OOH! Mexico, bring it on baby.”

I thought my options over, but my excitement and curiosity conquered my fear. I thirsted to see a different way of life, I desired to expand my worldview and perspective. I knew I needed to see what poverty looked like. I knew I needed something new.

How could I run away from something I felt called to do? The answer was I couldn’t. I was reminded of a quote by Ambrose Redmoon:

“Courage is not the absence of fear but rather the judgement that something else is more important.”

One late April morning, I woke up on a stranger’s couch in Texas and my thoughts materialized. I said, “I am going to Mexico.” And that was it. I was going to Mexico.

Still Alive

Having been in Mexico for nearly a month now, I will save more details of my adventures for later posts. But I want to assure you that I am still alive, and have survived all of the dangers Mexico has thrown at me so far. None of the above warnings have been issues for me. Mexico is considered dangerous because there is a lot of violence, but locals tell me that it is like any country… there are good parts and really bad parts. If I am going to go to the really bad parts, I will save them for later. Nearly all the places I have visited so far feel safer than an average American city. I feel comfortable walking alone at night. 


This cow did not like me, not at all.

 But just because I have not had any drug cartels kidnap me, does not mean I have not run into a few “dangerous” situations. I list here 15 of my most dangerous experiences so far:

  1. Crossing into Mexico through a border city that is headquarters for Mexico’s most powerful gang.
  2. When my bus arrived in Mexico, it dropping me off late at night in the wrong city.
  3. An angry cow charging at me atop a mountain in Guanajato.
  4. Riding in taxi in Mexico City with a driver who drove as if he was a stuntman for the Fast and the Furious.
  5. Developing a severe sunburn that took 15 days to heal.
  6. Learning how much college debt I might acquire.
  7. House-sitting for a friend while he was gone for a few days, and his landlord coming to demand rent that day.
  8. Not being able to find vegetarian restaurants or food anywhere.
  9. Touring a cathedral that only allowed access to the bottom floor, and then climbing four flights higher.
  10. Stepping out of hotel in Mexico City late at night and getting surrounded by Mexican prostitutes, one of whom I am quite sure was a man.
  11. Getting followed city to city, hostel to hostel, by a mentally unstable and potentially dangerous dude.
  12. Almost getting led into a secluded alleyway by a pretty girl, which may or may not have been safe.
  13. Staying with a small-time Mexican drug-dealer for two weeks, then watching over his house for a few days and having his landlord come to me to demand rent.
  14. Growing a really big beard (learn why in a later post) and then looking at myself in the mirror.
  15. Nearly getting bitten by a really big, really vicious stray dog.


A view from the top of a cathedral I climbed.

Closing words: What I have learned

Mexico has treated me far more nicely than most people led me to believe it would. In fact, Mexican people overall are the friendliest and warmest people I have come to know. I don’t think people in the USA were purposely lying to me about the dangers of Mexico, but I do think they were biased and misinformed. And who can blame them? TV and the media love to pick up on all the bad stories (even if they are only a few) and focus on them, because it excites peoples’ emotions and gives them comfort into thinking they understand the unknown.

And there are bad stories in Mexico, some very bad ones, but by keeping your head up and following common sense, one will be fine. The same goes for hitchhiking, Couchsurfing, shark-diving (okay, I don’t know about that one), and most other “dangerous” activities. Just because there are a few horror stories out there, that does not mean that the activity at hand is not overall very safe. That is what I think anyway… and guess what? I haven’t died yet!


If you have reached reading this far, thank you and sorry this post has been soooo long. This is my first blog post ever. Please let me know what you think!