Reflections and learnings as I turn 30

Today I turn 30. I’m not really sure why, but having revolved 30 times around the sun seems to be somewhat of a milestone. I’ll still take the opportunity to reflect on life so far, and what I want it to be in the future.

Sam Altman shared some really good stuff when he did, and I don’t plan on competing. I also don’t plan on releasing 1200+ slides like Ryan Allis did, even tho you should really check them out.

At 30 I find myself very happy in a period of total uncertainty, and wonder how I got here. My life certainly didn’t go according to plan till today, but I must admit I’ve had an unfairly easy time for now.

What I’m happy about is that I don’t have any regrets whatsoever. I’ve always taken decisions very fast and mostly based on gut feeling, and I think this is how I’ll continue to take them in the future.

From not pursuing a Masters degree, moving to SF, getting married, having a kid, moving to the mountains.. if you don’t take the decision, it will not happen. And if you wait for the perfect time or reason, it will never happen.

I found that inertia has to be actively fought, but that life gives you the right clues which are very evident. You just have to act on them.

The regret minimization framework

During these last years, I’ve questioned more and more what I do to make sure that it actually aligns with what I want to be doing and what impact I want to have on the world. I think this shows in the portfolio of Mission and Market, and in the motivations that led me to start Kickpay.

What I’ve found most useful to make these and other decisions is the very simple and probably obvious “regret minimization framework”, illustrated by Jeff Bezos when he explained how he decided to found Amazon.

Up to today, this has made it very easy to answer a lot of questions.

  • Would I regret marrying my wife so young? Hells no.
  • Would I regret having kids at a young age? Nope.
  • Would I regret burning my life working and not spending time with my amazing wife and family? Most definitely.
  • Would I regret trying to move to the mountains and live more in harmony with nature, even if it would mean saying no to a lot of cool business and work proposals? Definitely not.

And so now I’m once again left with the question: what would I regret (not) doing when I’m old?

What I’m starting to think more and more is that I would regret a lot not being more active in helping protect the planet from our own uncontrolled growth and consequent devastation.

Leaving a worse planet to my kids than the one I found seems to be too much of a burden to have when you’re old.

As much as I think government will be the #1 driver of change in this matter, I do believe that startups have a lot to say and do about it.

So given that this is all that I’ve been doing for the past years, I think that I’ll have to be more involved in finding, helping, investing in, founding, startups that have a clear goal to preserve our natural resources.

Fortunately this is getting easier by the day with amazing technological innovations happening all around us from nano materials to biotech, AI, financial technology, logistics, and more.

What I’ve found is that investing in companies like Aspiration, Clara Foods, Vitro Labs, has made me more proud than anything else I’ve done and thus think that this could be a clear indication of the path to take.

We’ll see where it leads.

Bonus: some random thoughts on different aspects (some of these are more reminders for myself, but maybe they can be helpful for others.):

On relationships:

  • Marry the smartest woman you can find. The advantages are so many more than the disadvantages.
  • Marry someone that is not like you but that likes the same things you do, and more importantly values the same values that you hold.
  • Nurture your relationship every day, it’s so easy to give it for granted and let it all slip until it eventually breaks. And you do not want that.
  • You only have two parents. Spend time with them and care for them. You’ll soon be in their position.

On money:

  • The best way to make more than you spend, is to spend little money in the first place.
  • The saying that money doesn’t buy happiness is a myth. Unfortunately our world still revolves around sovereign debt money, and to pay for what makes you happy you will need to have sovereign currency.
  • This is very different from saying that materialism produces happiness, quite the contrary — but in my opinion you need more than your basic needs to be happy.

My experience has been that happiness comes from:

  • 1) loving other people and being able to provide for them (money enables this).
  • 2) Having the freedom to live wherever you want and freedom to do whatever work you want (this is also usually enabled by financial security. Ingenuity is a part of it but without money it has too much risk for most people)
  • 3) Experiences: travel, sport, food with friends, etc. (all of which are enabled by money).
  • In short, money (not a stupid amount of it, but enough) buys happiness for me, but the line is short. Having said that, it’s better to not have much money rather than being miserable trying to make a lot of it.

On kids:

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Goodbye San Francisco, Hello Italian Alps

Marmolada and Bindel Path. Copyright

Exactly two months ago I resigned from Kickpay and we packed our luggages, sold everything that did not fit in our car, gave back the keys of our home and started an amazing two months trip through the US and Caribbean.

Now that trip is over, and these are our last few days as full-time residents of San Francisco, the feelings are getting weird.

San Francisco has given us a lot. We both quit our jobs in Italy and moved here in the summer of 2011 with absolutely nothing.

It’s pretty unbelievable what we’ve done and experienced in this short 5 year period.

We met some wonderful people, brought an amazing new person into the world, changed a lot, achieved a lot professionally, and made lasting friendships that will be with us forever and shape our lives.

But, sometimes, you have to change.

Sometimes, you have to realize what is the most important thing in your life and why you’re doing what you’re doing: for us, that is family.

We realized that having kids and being only childs with older parents 10,000km away is a bad decision for all parties.

Life happens for everyone, and the regret of not being close to family when it does is just too big.

So we’re packing our bags and moving to Trento, Italy!

London, Berlin, Paris and Milan all less than 3 hours away.

Why Trento? The list of reasons is endless, but we like to sum it as “Italy not in Italy”.

  • Trento is an autonomous Province which gets to reinvest 90% of its taxes, which it does very well.
  • Easily connected to Milan and Rome with high-speed trains, airport is 1h away.
  • Nature without equals: the most beautiful mountains in the world.
  • Very sport-y culture: ski, mountain bike, kite surf, etc.
  • Hundreds of lakes, including Garda, Levico, Caldonazzo, Ledro and more.
  • Extreme focus on the “territorio”, which means a mix of nature and the social structures present.
  • Very community-focused.
  • Part of “Triveneto”, highest industrial output in Italy.
  • Most innovative district it Italy, with very heavy innovation investments.
  • Amazing schools, bilingual in english and a lot of german.
  • Great food and our favorite wines.
  • Tons of parks in urban areas.
  • Tons of kids-focused events regarding innovation and nature.
  • Optic fiber in town and a plan to bring it to everyone soon.
  • Consistently rated for highest quality of life in Italy.
  • Very very decent weather with tons of sunshine (but much more rain than SF).

San Francisco is a pretty amazing city, but if you have kids, I don’t think you could design a better place.

Where we’ll spend our first month and a half

We’ll miss San Francisco though.

There are a lot of things we will miss about San Francisco, and we’re going to find so many more after we’ll have been away for a while.

Most of all, I will miss working on Kickpay. Leaving a company you’ve founded and poured all of your effort into is very hard. Fortunately, my two co-founders are awesome and will continue to work to bring our vision to life.

We will also miss all of our SF friends, who have become as a family away from home.

And then YC; having meetings every single day with amazing people; the public parks, free tennis courts and amazing playgrounds; the weather; the scooter commute; cheap gas; being “the one who left everything and flew all the way across the globe”.. etc.

But we’re insanely excited about getting to raise our child in Trento, in Italy and in Europe.

We are excited about:

  • being able to afford any additional children;
  • having infinite small nice towns around;
  • living in real nice houses not built of cardboard;
  • eating good genuine food with no crap and infinite ingredients lists;
  • cheap rent;
  • free childcare and good public schools;
  • free healthcare and no insurance stress;
  • not having to worry about paying for college;
  • a lot of beautiful and affordable mountain lodges (“rifugi”);
  • being close to the sea (where you can actually bathe);
  • obviously real espresso, gelato and pizza;
  • and so much more!

We are also extremely excited about getting back into a young and emerging tech scene where we can have real impact by bringing back what we’ve learned in Silicon Valley as well as continuing to invest in more awesome founders with Mission and Market.

Being at a stone’s throw from Berlin, London, Paris and any other amazing European is the icing on the cake. More on this on another post.

Related to this, I’m also very excited about the work I’ll get to do at my new job, which I’ll announce in the coming weeks.

Not running a startup full-time, other than enabling me to spend more time in nature and with my family, will also enable me to start writing more — so expect a lot more posts coming in the next months as we settle down.

If you’re in Europe and want to meet, say hi!

Farewell, Betable

Our first milestones champagne bottles: Recapping of Betable 1.0, my hire, Jeffrey’s hire, Tyke’s hire, Seed round, Mike Malone’s hire, new office + major deal, Richard Crowley’s hire. Unfortunately all of these bottles got thrown out when we switched cleaning companies, so this is the only picture that proves their existence!

After 3 years and half, today is my last day at Betable.

I gave notice 2 weeks ago, with a lot of mixed feelings.

Joining Chris in helping build Betable was probably one of the best decisions I ever made, and I’m incredibly grateful to him for taking a chance on a young crazy immigrant he’d just met.

I joined in the summer of 2011, with no product, no funding, no team (0 engineers) and no customers — now we’re an amazing team of almost 40 people, raised more than $23M and have a game-changing product.

I’ve been lucky to be able to see such a high-quality startup get started from scratch, and blessed to have been able to help.

As I leave Betable, I realize the company is in the best shape it has ever been — with an awesome and committed team, an insanely good product and a world of opportunities at its fingertips.

I’ve learned an insane amount over the last years from Chris and the rest of the team and I’m sure the learnings will all be invaluable as I embark for my own entrepreneurial journey.

But I, and Chris, always knew this moment would come. I could feel the itch building.

So now the feelings of freedom, excitement, fear, restlessness, pride, and a couple more are all mixing up.

Moving forward I will be working on a new company in the fintech space with two awesome co-founders.

But the feeling that trumps them all is excitement: I’m incredibly excited about our vision, the opportunity and the early backing of some awesome investors.

I’ll be heads down building product for the next couple of months, but I’ll try to share publicly what we’re up to soon enough.

In the meantime, if you want to chat — you should tweet at me.


Losing that once-in-a-lifetime opportunity

Everyone experiences rejection in their life: a girl you have a crush on rejects you for someone else, a club or society denies you access or membership, a group of friends stops calling you, investors pass on your company, you don’t get the job or promotion, etc.

It happens all. the. time. Sometimes it’s fair, sometimes it’s not. Sometimes you should experience it but you don’t.

If I try to sum it up for myself, I think I’m still on the fair side. I got rejected a lot, but I also got a lot of things I shouldn’t have. That balances it out ok.

But what happens when you think that this time it really was the once in a lifetime opportunity, and now it’s gone? How do you cope with that?

  • What happens if you’ve been madly in love with someone you think should be your life partner and they reject you?
  • What happens if you have a chance of getting the job you’ve always dreamt about and you get rejected?
  • What happens if you don’t get the investor you’re sure would change the fate of your company?
  • What happens if you don’t get the deal of lifetime?

Let me tell you what happens: nothing happens. It’s gonna be fine.

Most of the time, the reality is that what seemed like a once-in-a-lifetime opportunity, wasn’t in fact one.

Most of the time you weren’t even qualified or the right person/team/company for the opportunity, but you can’t realize that until much later.

It’s really hard to cope with it and put things in perspective immediately after being rejected, but it’s nothing else than a stepping stone to something better.

Another girl, investor or job will pass along at the right time, and you’ll discover they’re even better than you could have dreamt about.

Having been told no will make you stronger and if you keep on working hard towards your goals you will have the double satisfaction of showing them how wrong they were, or maybe (should you not have such an exaggerate ego) reconsider their choice.

“Business opportunities are like buses, there’s always another one coming.” — Richard Branson