Failure 🧘🏻

It's time for builders #1

My newsletter is back!

7-8 years ago I was writing about big political trends, books, and trips.

Now I’m going to talk about my journey as a startup founder.

I took the title “it’s time for builders” from Italy’s president Mattarella.

If you’ve been automatically added to the mailing list, it’s cause we had fun moments together and I know I can count on your support and feedback 😉

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The first edition is about failure, which seems a pretty gloomy start but in fact… it’s a natural, constant presence in the life of builders.

So what happened, and how do I feel about it?

1. it's a clear failure: for 2 years we tried to build an alternative to LinkedIn; out of 10 MVPs, Peoplerank went better than all others but it was far from enough.

2. it's my fault: I take full responsibility for the failure, starting from the arguably reckless choice of the bet.

3. disappointment, not guilt: I am disappointed in myself for not delivering on what I pitched, but we gave it our best and we know failing is part of the game.

4. not giving up: we will keep building. All three of us are now freelancing while we look for the next problem to tackle.

5. thank you: I am really grateful for the support, patience and presence of my family and friends, team, investors and early users of our products.

Drawing a line

Building means uncertainty.

Knowing when to keep going v. pivoting is always a puzzle.

You might have seen this image before:

There are three main reasons I stubbornly pushed to keep going for 2 years

• I had many opinions on what a LinkedIn alternative should look like

• Each domain is complicated, and it takes years to become an expert in a single one

• Our MVPs got better: Peoplerank was built quickly and it was simple, catchy, controversial enough to spread via word of mouth

We ran out of strong ideas and money though, while we realised how hard it is to force a peer-to-peer platform to go viral. We were definitely far from the end of digging shown in the picture.

So, we are stopping here, but we’ll root for anyone else trying.

LinkedIn delendum est… it took some time for Rome to take down Carthage, but eventually it did happen.

Taking stock

There are things I’m proud of!

• personal runway: before taking the jump, I minimised my downside: I got married, bought a house, saved a lot. Plus, I never adjusted my spending to my wage level while at Plug and Play, and it was easy for me to go super frugal again. I am damn cheap 😂

• team: shoutout to Jan and Vic for grinding with me. We were the right team for the product we were trying to build, and shipping was never the issue. We had lots of fun. We stuck together through many difficult moments, even if we were in remote most of the time.

• investors: we’ve been through many iterations and pivots. That’s what the 0-to-1 phase looks like, but it’s understandably worrying for investors. Ours, however, kept cheering us on and helping us whenever we asked. Each of them leveraging some of their unique assets - visibility, network, advice, community events.

• product marketing: in terms of my own skills, the thing I was mostly curious about shipping a software product - after years of selling services. I started from scratch and the learning curve was super steep, but I am somewhat proud of the progress. Peoplerank was in many ways well done, refined, sleek.

Of course, I also screwed up big time 😅

• team’s personal runways: Milan is a very expensive city for my cofounders to move to. Even harder for Vic as she needs a visa. It’s been 2 years of travelling, moving places, getting documents and living under uncertainty all the time for them. They are only money problems, but money is very relevant for startups.

• business model: maybe you have heard the inside joke “first-time founders think about the product, second-time founders think about distribution”. This definitely applies. Building product was the newest part for me, plus B2C / peer to peer distribution and monetisation are just so hard. I was too naive.

• not playing to my strengths: at Plug and Play, I sold €16mln in enterprise contracts. Sure, it was consulting, and an established brand, but the learnings of B2B sales would have carried over. Quite frankly I thought - I had never done sales, run for office, or led big teams, and I got them right at the first shot. How hard can it be? Well, very hard it turns out.

• crushes: for 2 years I went from one product crush to another. It’s quite similar to love, or sales: never go from exploring to doubling down before you have strong early signals of a fit. Meaningful tests, however, no matter how lean, require significant amounts of effort. It’s a very hard balance to strike.

Redefining my identity

Obviously, failing sucks! A lot.

We all take defeats personally and, in the case of startups, this identification between the founder and the failure is maximum because startups by definition require a maximum level of ownership, attachment, emotional investment.

It is very easy to go from “the startup failed” to “I failed” to “I am a failure” to “I am a total failure at everything”.

I did have a brief but intense phase like this 10 years ago, and compared to that this time I have great people around me and the memories of professional success - so it’s been easier to put a hard floor to this self-defeating loop.

My inspiration is from one of my favourite thinkers right now, in this case (bonus) holding the ancient Romans as an example:

I am a husband, father, son, friend, citizen. I build things but I also write, network, consult others.

Building is my main focus, and naturally I have had successes and failures in many different fields - I will have many more.

Some people that make it are great, some are lucky, most are both.
All those that fail were not good enough.

Still, trying always shows courage. If I could go back, I would take the jump again.

Fortuna audaces iuvat.