« post-mortem: what did I learn from the painful downfall of a startup

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I started my first proper gig as a CTO in July 2017, today is my last day and I am leaving with a heavy suitcase full of learnings: technical and non-technical, this post focuses on the non-tech ones.

Getting Hired

It’s common to get hired by early-stage startups thanks to networking but because of this you will lower your defences: a head hunter taught me this and it’s absolutely true. 
You won’t notice little clues during interviews, you won’t ask enough questions, you won’t look at the past of the company with a critical eye.
In retrospect I also was too keen on being a CTO, I wanted that title for years (titles are BS!), thinking I could do a better job than many CTOs I’ve met in my consulting life. In reality, it’s fair to say that I’ve been at best a tech lead, a DevOps, an Architect, a QA, a BA, a FE engineer, a BE engineer but rarely a CTO in my last two years. Part of if it is intrinsic to be at an early stage but because we never scaled then I also never stepped away from the code and pushed hard on CxO to elevate myself at that level.

Early Stage Startup?

One of the many mistakes I’ve done was not looking deep enough into the company houses website, look at the balance sheet, look at what the founder had done before, look for how many years they had been trying to make it. Don’t confuse perseverance and stubbornness with mastery.

Who are the investors?

The seed investors will influence the future of the startup: if they are not digitally savvy but just people with pockets full of money they won’t help the founders to steer towards the right direction. They will also pull out easy once they smell that the ROI won’t be met.

Who are they, are they ethical? Would you borrow personally money from someone that you don’t dig at an ethical personal level?

Expect, push back, deliver

If you are part of the executive team you should demand to always know:

• Runway
• Current Company Evaluation

If you are part of the executive team you should always request:

• Vested options with cliff
• Participate at board meetings

I had no visibility on the first two points, I had pointless EMI options and I got pulled out from board meetings in the last 6 months:
the excuse was that I was too busy, as it turns out, in hindsight, those were the days when the cash flow was low but I was unaware until one month from zero cash in the bank.

No lies, no vanity metrics

CPA, LTV: are you creating a feasible business plan or you are just trying to attract investors? Are you lying to yourself, your employees, your investors, for the sake of following a dream? Step back, you will never achieve that dream with lies. You will achieve it with hard work, flexibility, verified assumptions, iterations, controlled experiments, empowering your tech team, taking risks.

Focus

Focus. On customer happiness, when the majority is not getting what they subscribed for, pivot, change direction until you find a sweet spot where your customer segments match your offering.
Learn to walk before running, have a sustainable growth plan. Focus on quick wins, cheap gains, run the current mile looking at the moon but don’t invest time, money, people in trying to land on it.
Be the customer and be the customer support team. Focus on your users, in early stages keep customer support close to the engineering team in order to learn by osmosis what works and what not. 
You are building a product for your users, not for yourself, do not ever forget that.

UX/UI

There is not such a thing as a startup which doesn’t embed a UX expert and a senior tech team from the early stages.

You can probably get away with it only if you are doing only backend work on a B2B product!

Changing the UX/UI/branding won’t fix your product, it’s an expensive exercise. During my time there, we did at least 3 major designs, I know of another two before my days. In none of those iterations, we ever excelled at executing it or measured properly impact and gains.

Data Driven

Someone in the team needs to know how to look objectively at data, they need to master Google Analytics, Spreadsheets and potentially at least a query language or a tool to extract insights. And then make decisions based on those findings.

Chief Technical Officer

I haven’t done a good job, if a startup sinks it’s everyone’s fault, exec team more than anyone else. I thought top tech choices were enough, execute fast, us techies always see the world with a techy eye, we think we are the best, that if the tech is cool then everything will flow. 
It turns out tech is the spare wheel in the car. I’ve seen so many companies succeed with horror IT systems, maybe they won’t strive, maybe they will struggle at some point to compete if they don’t keep tech stack at state of the art, they will have to pay a high price someday for that tech debt hanging there but at least they will have a validated business proposition. 
MVP -> real revenue -> pay the debts, this should be executed in months not years!!!

Code, architecture, tech: it matters to a point, as a CTO you are like a tightrope walker on a wire balancing quality (strategic decisions) and getting stuff done (tactical). I wish I coded less and pushed back, chatted, convinced more. At the cost of stopping the line: put the tech team in code strike until a few basic decisions would be accepted.

Hiring

Don’t compromise when hiring, it’s better to be short on engineering team than having a dysfunctional engineering team to deal with, there’s no energy or time to deal with underperformers, people who don’t row the same way, people that are misaligned from a tech, quality, process perspective.

Get Help

I’ve got help, I talked to a few people, I might not always have listened to them, but if you know people who have been there before, go for it, make it a habit. If you don’t know anyone there’s plenty of CTO meetups, it might be a good start: you are not alone.

Are you dumb? This are basics!

In theory, I knew all the things that are in this post, I’ve read the books, I’ve got years of experience in the field, in reality, once you are in the trenches it gets harder.
You need to have the experience and the training to be able to perform well at full speed. It’s easy to judge from the outside, it’s easy to say, don’t do this, it’s a different story once you are swimming in murky waters. 
My weaknesses are probably around convincing, pushing back, stepping back. For the first time in my career, I just didn’t quit, I insisted, I stuck around, and I am proud of that. But I’ve read somewhere that as a CTO you should threaten to quit from time to time. I probably should have done that. I think it wasn’t clear enough that the tech team wasn’t enjoying themselves, that we were forced to build something we disagreed with it, most of the times.