Lessons from My Failed Startup Experience

Mor Sela
Mor Sela
Jan 9, 2017 · 5 min read

“I may be going nowhere, but what a ride.” ― Shaun Hick

The company in which I had invested my life was recently closed (Docady — RIP).

It was not due to bad execution, nor an unclear vision. We had an aesthetically pleasing and highly-functional product that we were proud of, endless use cases, and loyal customers.

Our problem was that we wanted to be everything to the users: a one-stop shop, collector, organizer, manager and assistant for any and all of the user’s life needs. It was a grandiose scheme and… it failed.

We failed to stick to the most basic rule that new startups should be reciting in their sleep — a well-defined pain, and from that, a (somewhat) well-defined market.

At times, we were almost there. Users adored us for our basic document management skills which were something like a specialized personal Google Drive / Dropbox for managing your and your close relatives most important documents. Some were even willing to pay for it. But even then, it was too little too late — instead of capitalizing on the most promising use cases, we kept looking for the next vision-fulfilling-feature.

Personally, I took a lot from the experience, some appear simple in hindsight but were definitely not obvious at the time, at least to me. I would like to share 5 distinct lessons that I have taken with me for my next adventure.

(I) Start fast, deploy fast, learn even faster

I won’t say a lot on this topic — it is the first rule in the book. In retrospect, we should have done everything faster. It took us over a year to publicly launch the product (~9 months ‘till beta), solely because we wanted it to be pixel-perfect ( and it was! Almost zero downtime and a beautiful UI). We had a vague idea of our KPIs but only partially built our plans around them. We didn’t try to adapt and learn from the data. We should have had fewer (but more important) KPIs and made them our core focus.

(II) Nourish your team

Since your team is the most important part of your start-up, you should manage your time accordingly. Plan compulsory monthly one-on-one or team meetings, not only because they need to see you, but because you need to see and hear them.

I am an engineer so I recognize the pure distaste many engineers have for meetings but that should not relieve engineers of important meetings. You should tailor yourself to creating a culture of precise & concise meetings. In Docady we used a “tool” borrowed from Onavo (compression startup acquired by Facebook) — any time a meeting / discussion / sync went offtrack and become a waste of time, any one of the participants could just say “!חדל” (Stop!) and the meeting would be either adjourned or returned to focus. That practice saved us days.

Another minor tip for all of you syncers out there — don’t sync next to your workstations. Use that 10–30 mins standup meeting to catch some sunlight / change scenery — it does wonders for both the meeting and participants, helping all to address matters from a fresh perspective.

(III) Cherish your technology culture

Another issue is that it is crucial to imagine and implement a “technology culture” as soon as possible. What is a “technology culture”? It is the sum of all technical frameworks, development methodologies, tasks, project management decisions and anything technically relevant that helps moving the organization forward. When it is defined properly, it is amazing to see how new engineers adapt quickly.

As a specific example — in Docady we implemented a lot of backend tests, not Test Driven Development methodology for the sake of it, but only as many tests as were needed to make us feel safe enough to deploy whenever/wherever we wanted. It takes time and effort to reach that deployable state, but it is worth it. The number of bad bugs in production we had was minimal and any developer could feel confident enough to change any part of the backend, because they knew that our comprehensive tests would fail if they did something too wrong.

(IV) Don’t overestimate security

Coming from a cyber-security background, this is a hard truth for me. Over the last two years, we invested around 16% of our time making everything as secure as possible — from greater than military-grade encryption based on Amazon KMS, moving secrets to Vault, encrypting client application DBs, discussing Zero-Knowledge protocols and even more bombastic acronyms and technologies. In the end — all that work was futile .

You, the managers and founders of early startups, should take a moment to evaluate: a) what is the real risk? b) what is the sufficient minimum security measure that one can take in order to get on with the real task at hand? My answers now would be minimal compared to before — Use a password manager (e.g. 1Password), use two-factor authentication everywhere, use HTTPS and educate your staff regarding security hazards. That’s it.

Once you’ve achieved a tangible market fit and appropriate company size, it’ll be time to rethink your security options.

(V) Naming is everything

“As names have power, words have power” — Patrick Rothfuss, The Name of the Wind

One of the first things we did at Docady was to decide our naming convention. Ideas ranged from animals to whiskey types to superhuman beings. Eventually, we went wild and choose IKEA furniture lines as the key naming convention in the company.

We took the time for it, not only because this is fun, and a great gamification tool for developers (let a developer pick the name of his project, and you will lose him for a day :) ), but also because nobody wants to be that company that has multiple projects that could not be discerned (e.g “old backend” and “new backend”), and good naming can help you make things coherent, both internally and externally.

The vision behind Docady is still alive and kicking — just think of how many manual, repetitive, ‘could-be-automated’ personal tasks you do each month! I’m personally eager to see who will be the next to pick up this heavy gauntlet.

Being part of a failed startup was never my dream, I always expected it to grow more and more. It was an enlightening and sobering adventure, which gave me a lot, and took a lot. The next big adventure awaits!

To my colleagues I’ll say this — Learn your lessons (preferably sooner), always be critical, and never stay still.

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