EntrepreneurshipGrowing upPublished on The Startup

A Letter From A Failed CEO: What I Learned From Founding A Startup That Didn’t Make It

By January 28, 2019 November 11th, 2019 No Comments
Don Quixote fighting windmills

Yes, you guessed it, this is an emotional one. This post is how I’d like to put closure to a 4-year business endeavor that has seen more downs than ups before taking its final dive. In a way, I’m not sad that it’s over, but I’m not relieved either. I guess that when you’ve been taking hits for too long, the one that finally puts you away doesn’t feel any different from the ones before it. You learn to be numb to the things that don’t help and that’s how you keep going. So if I’m not down-selling this, it just feels like another day at the office. Except I’m not in the office for there is none anymore. So without further ado, here’s what I’m taking with me.

Lesson 1: Rebel a lot, but not on everything

There is a reason things are the way they are

There’s a reason why things are the way they are, and most of the time, it’s a very good one. In nature, we call it Entropy. Systems naturally evolve into a state of equilibrium. It doesn’t matter if the arrangement is to the best of each party ’s best interest. It just matters that it’s stable.

Entrepreneurs are built like rebels. Beware

Most of us entrepreneurs don’t become entrepreneurs when we get a great idea and stumble upon a big opportunity. Most are born with that spirit, are raised to have it, or acquire it early on in life, years before we apply it to a legitimate business. We are good at problem-solving, identifying needs and coming up with solutions. We might experiment with these skills here and there, but until we launch a business, that whole potential stays largely untapped.

So when the day comes when we decide to strap on a pair and embark on our first serious entrepreneurial journey, whether be it a startup or an agency, that potential overflows. We rebel against every standard, we challenge every belief and we go out of our way to solve any problem that we can think of. That’s a slippery slope, and you only come to realize it when you’re writing your own version of this article, god forbid. Here’s an example of a time when I didn’t listen and wanted to challenge the status quo more than I should have.

Listen to reason

People told me that you can’t start a company with no capital. You can absolutely start one with very limited capital, but you can’t with zero capital. What I learned is that they actually were wrong. You can very much start a business with zero capital, but it’s very difficult, even in tech where it’s all websites and apps on the cloud with no expensive physical assets. That’s why startups have a clear funding model. It’s because people tried and failed. And through those trials and errors came the funding model that isn’t necessarily in the best interest of startups, but it’s stable and it often works. I rebelled on it even though I didn’t need to. It wasn’t my brightest moment.

Funny thing is that this tends to happen very early on. When you think of it, it makes perfect sense because when you’re starting out, you’re not going to listen to anything that hints to the possibility that you’re going to fail.

Don Quixote fighting the windmills illustration

Don’t fight the windmills

I’m not saying that you shouldn’t try to launch a business with limited capital. All I’m saying is that one should recognize the challenge and address it, not turn a blind eye to it and go full Don Quixote. Go make some money before you invest yourself in your project. I know it always seems that you’re running too late and someone is going to beat you to it. But odds are, someone already did beat you to it and someone else is working very hard to beat you both.

And even if this isn’t the case, would you prefer to arrive at the battle early or well prepared? Because you can always find another idea, but the years you’ll invest in something that’s not going anywhere can’t be replaced. I’m not saying you should go find a job and slave away in it for several years until you have a hundred thousand bucks in the bank. Just make sure to have a little runway for your business because you even if you can survive without cash, your business can’t. I needed to learn to stay focused on the mission and not let my problem-solving prowess get the best of me. Don’t turn a blind eye to the challenges, address them. it’s easier like that.

Lesson 2: Business drives close people closer, and far people further

I wish this lesson could do you any good, but I’m afraid it can’t. The reason is that when you’re starting out, you don’t know if you’re actually close to your co-founders or not. The good thing is that at least when you’re closing shop, you really know for sure.

Pairing tech with social isn’t enough

People gifted in technology should always partner up with those with more social skills, and vice-versa. But that’s the easy part. That’s the obvious part. The rest is a little more complex. It’s not enough to partner with someone because of their skillset. Partners need to share the same vision, work ethic, culture, values and at least be in the same ballpark when it comes to goals and ambitions. That’s the tricky part, especially in this day and age and I’m going to give you an example as to how exactly this can be an issue.

It’s all about the subtle values

You see, if you’re a startup founder or founder-to-be, chances are that you’re in love with some silicone valley unicorn that you want to be like someday. Your idea of a perfect organization would resemble the Googles and the Amazons of the world. You learned that being successful is all about quality and execution so you start your journey with these unyielding high standards. That’s all dandy. But the road to where all of that is possible isn’t. And I can assure you that it doesn’t have a single bean bag on it.

Struggles bring out the truth

When you’re struggling to keep paying your hosting fees and your employees, let alone yourself, quality starts to matter a whole lot less. Chances are, people gave you a lot of money because you promised them certain milestones under certain timeframes and when those start creeping up on you, you tend to start sweeping things under the rug. That’s when your values are challenged. Or shall I say that’s when each one’s true values surface? If one is more quality-oriented and the other person is all about immediate results, nobody can be happy because you can’t have it both ways. You can’t pace yourself and be full speed ahead at the same time. Being either this or that is a matter of personality and goals. It doesn’t matter if you’re this or that. What does matter is being on the same page. Having a match at the beginning helps a lot. It’s a lot is easier if everyone is rowing in the same direction. That’s why I said that it drives close people closer, and far people further. This is just an example of how sharing a value can make or break a team.

Flexibility helps. But backbones are essential

I believe that no matter the area, being flexible helps. After all, moderation is always key. What I’m arguing for however is the fact that people shouldn’t do things that are not aligned with their values, not because they’ll be miserable, but because it doesn’t work in startups. We’re launching our business because we want to exercise our values, not see them fade away. The more flexible you are, the more time you’ll be miserable before you fail. If this sounds like it’s coming from personal experience, it’s because it is coming from personal experience.

Lesson 3: It doesn’t have to be hard. Most of the time it is. But it doesn’t have to be.

I would like to expand on this but I guess the title says it all. It doesn’t have to be hard. But it usually is. I think I know why. there’s something called Parkinson’s Law and it states that

Any task will inflate until all of the available time is spent.
_C. Northcote Parkinson

Apply this law to a bunch of entrepreneurs high on startup pills and it sounds somewhat like this: Any entrepreneurial project will inflate until all of the founders’ energy is drained. This translates well into my first point about challenging every standard. We keep expanding the project by spinning wider or digging deeper until we can’t manage.

There’s nothing wrong with having a small mission and executing it well all while being happy. It’s ok to have a weekend off for a change. There’s nothing wrong with being able to leave your phone at home every once in a while to disconnect. There is nothing wrong with taking a breath to enjoy where we’ve gotten and deciding that we like it as it is and not wanting to grow it anymore. Businesses that don’t grow die, but not everyone has to 2x every year and not every business supports a lot of scale.

We just keep convincing ourselves to do more, until we’re miserable and end up not wanting to do anything at all. What good does that do? You can shoot for the sarts but take it one step at a time. This is where the values that I was talking about come into play.

Lesson 4: You learn a lot, but a startup is not for learning

A startup is about fulfilling a mission and making money. It’s not the best place to pick up a career path. It seems pretty straightforward right? It isn’t. When you’re starting out with your cofounders, everyone will have to learn new things, generally the closest thing to their background. You might have to learn accounting, design, social media, digital marketing, SEO, supply chain, recruiting and many more things. Everyone on the team will find themselves learning new things and some will develop a taste for it and enjoy it very much. But be not fooled: Just because you picked up a digital marketing class on Skillshare doesn’t make you fit to fulfill such a pivotal role. Similarly, just because you know some Javascript doesn’t make you a legitimate developer capable of building whatever you’re building. You can help for sure. But stick to your job.

You will not pick up a trade

You can learn a lot through the lifecycle of a startup, but you simply will not become a developer, you will not become an accountant, you will not become a salesperson if you were never one before. Sure, you might discover a talent or a liking to it, yes. But these things take time and a startup is not the ideal place to learn because you’ll have so much else to do and so little time before you run out of gas and go out of business. You can learn some coding, you can learn some accounting, you can fill some sales roles, but that’s the extent of it.

Your business probably can’t handle your learning

On the other hand, let’s suppose your business can survive a few years tolerating your learning efforts, you can become a kickass developer or a fine salesperson during that time, but you’ll cost your business so much more to your sole benefit. This means you’ll be a great developer or salesperson right after you drive your business to the ground for not being there for all the other things that needed doing.

Lesson 5: Write things down, from day one.

You know, if you learn just one thing from this article, please let it be this one. Unlike the other lessons, this isn’t a blab that you have to figure out how to apply. This is one solid piece of advice that you can simply do today. Sit down with your co-founders and write things down. Here’s a list of what you absolutely have to write:

  • Vesting plan

    If you don’t know what this means, you’re setting yourself up for a very uncomfortable situation sometime in the future. In a nutshell, vesting shares is basically a plan for when one of the equity holding founders decides to leave before the project reaches a major milestone such as an IPO or an exit. You need this more than you’d think. Here’s an article that you need to read very carefully before you decide you’re too cool to vest

  • This should be the answer to the question: What would constitute a success for this company. The more specific you can be the better. Give many cases because companies change. One day you’re selling potato peelers, the next day you’re inventing the world’s largest particle accelerator and your mission of peeling every potato in the world is moot. think about something in terms of growth, like financial milestones, hiring, reputation. I always said that the day I walk into the office and find someone that I don’t know working for us, that’s when I can hang up my boots.
  • Expectations from each other

    For example, you can say that you expect your co-founders to split any bill with you equitably. Another thing could be that you expect them to not work on any other project while still working on the one you have.

  • Red lines

    Could be things like religious restrictions, morality clauses, basically anything that you will never be open to and which to be put on the record from the get-go.

Write these things down. Do yourself a favor, write them down. If you could sign a contract (especially for vesting) it can be much better. Trust has nothing to do with this. As a matter of fact, this can help people trust each other more.

Lesson 6: Trust your instincts, they’re never wrong

This one is a cliché, but I became acutely more convinced of it. Here’s the dilemma: You have this feeling about this move and you can’t really tell why you’re skeptical. All the data and all the objective parameters tell you to go through but you still have this funny feeling about it. What do you do? I would like to argue that you should listen to your gut feeling.

That gut feeling is the sum of all your experiences, research, thoughts and efforts trying to tell you something you already know and you should listen to it.

If you know yourself to be a very wary person, or if you know yourself to be the adventurous, gambling, shoot first ask question later type of person, then maybe you should take a raincheck on the whole instincts thing because it’s not for you. But for the rest of us regular folks out there, it’s our best consultant.

We were taught to be humble, to listen, and to be objective and I’m all for that. One isn’t an expert at something until they do it successfully. Then they don’t need the expertise anymore because they’ve already done it. We fear to trust our inner voice because: what do I know right! Wrong. You do know. And when you know, you know that you know. I find it especially helpful with people because with people we can’t quantify everything. We can’t quantify anything.

A few last words

You know, I’ve been writing this on the span of a few weeks now and I still can’t finish it. I don’t have enough time and energy to sit down with my thoughts, ponder on how things have gone by and write. I’ve been so busy running my new life and I must say: I’m ashamed. I’m ashamed of my new life, and the new me. The new me is an employee, and it’s killing me. There’s nothing wrong with being an employee. But there’s a lot wrong with me being one.

But then I guess that just because your project doesn’t work out the way you planned and you end up giving it up, that doesn’t mean you stop being an entrepreneur. Entrepreneurship is an attitude, it’s a way of thinking that you can’t give up even if you tried. What’s exceptionally challenging, however, is the life of an entrepreneur while they don’t have much to work on.

Entrepreneur are going to be entrepreneurs

Nowadays, things don’t feel right. I think that until I embark on my next mission, they will never feel right, they shouldn’t ever feel right because there’s something clearly wrong. And please spare me the “there’s no shame in failing” and the “failing is a sign of trying” hokum. I am well aware of it. But that doesn’t make it feel any better. What does, however, is recalling how events unfolded and figuring out what could one learn from them. I guess that in that regard, I’m consoling myself just fine.

I guess my attitude about this whole thing is similar to Jim Coudal’s when people used to ask him which one was his biggest failure. He always answered: “ I’m working on it right now, it’s gonna be awesome”.

Lastly, my message to any founder is this: Don’t be a hero. You don’t have to learn all these lessons on your own. However, If you think you’ve proven one or many of these lessons wrong, please do write to me. I’d love to hear it.

Ghaith Ayadi

Ghaith Ayadi

I’m Ghaith Ayadi [ɣaajθ ʕajadiː]. I am an entrepreneur who writes and designs. I specialize in Product Design and Branding and write about design, entrepreneurship, growing up and other things that matter. I currently do freelance work while I’m working on my next big thing. Reach me on:yo@ayadighaith.com