Startup Therapy podcast

There is a podcast that has been helping me a lot in the last 12 months.

It’s made by Startups.com‘s founders, two very serial entrepreneurs who started 14+ companies (yes, amazing) in their lives and talk about all the aspects you go through as a founder and CEO. The podcast name itself is amazing: https://www.startups.com/community/startup-therapy

There are great episodes that will clearly makes sense to you if you have started a company before, it doesn’t matter of which size, venture backed or bootstrapped. Will and Ryan, the two founders, do a fantastic job describing how you feel as a founder as they describe what happened to them in several companies. Most of the times you will find yourself saying “Fuck yes!”, as they clearly have been through a lot themselves and are able to explain what to do and not to do. Not just that, for a founder it is not easy to understand that what is happening to you, it’s normal and it’s common for other people in your role as well.

If you are building a company I highly suggest this podcast. Most of the things they talk about are really things nobody will understand if not other founders, and I know how difficult it is to find support and talk to someone who has been through this before.

I was driving home tonight and I just listened to “Bouncing back from failure” that is a fantastic one!

What’s so hard about Leadership

Leadership is a never ending discovery of yourself and that comes with lot of challenges. But what I always admired the most about true leaders is how good they are at protecting their people while things are bad. 

It’s incredibly difficult to be positive, not letting your team down and be present while things are bad. Even more when you don’t believe you will be able to fix that. Your investors, a bad board meeting, that customer you were supposed to win last month, payrolls knocking at your door and so on. There are moments in your company where everything goes bad and it gets worse day by day. It’s incredibly hard to show up to your all-hands and be strong, positive, smiling. It took me years to manage myself into that and understand that be there for my people was the most important thing to do anyway.

It’s incredibly difficult to be a shield for your people.

It’s something I still need to get better at, but every time I see a founder dealing with it, it reminds me what’s really difficult about leadership and why it has such a toll on you as a person.

People to avoid while building a company

This is something I would love to tell to a younger Stefano. I recently (finally) met a great mentor who reminded me how important it is to surround yourself with the right people while building your company.

While you build your company you should ignore 3 types of advisors/mentors:

  • Corporate guys: they are top manager in a BigCo, never been entrepreneurs and never will be. Almost always useless for entrepreneurs as mentors/advisors unless they want to buy your product or invest in your seed round but even then it should be it, don’t give them control/board seats etc. They don’t understand what you deal with but they will pretend to and give you more issues than benefits.
  • The wannabe“: I met many in my journey. This is a tough one. They might present themselves as entrepreneurs but once you dive deep they will likely be involved in 34 different things at the same time, they are advisors, mentors, CEOs and talk like they have seen it all. They are always looking at a conference to attend and ideally speak at. They are building their brand and trying everything to see what works but they are usually clueless. The first rule for an entrepreneur is to focus on one and one only thing. They will waste your time and sometimes do also damages, mostly due to their inexperience, like saying things they shouldn’t about you to other people or give you (really) bad advices on how to manage your company.
  • People that are doing it for the money: the best advisors and entrepreneurs help other people because they enjoy it and love it. It’s a great way for them to give back and something that they naturally feel the need to do. Yes, they absolutely need to be compensated (don’t commit a mistake here, always pay them, mix of cash/stocks with clear expectations) but they are genuinely involved because they like you, believe in you and have really something to say. They probably don’t need your money but paying them (stocks, with vesting, is the best thing), even something small, makes a difference in your relationship. The best people in this category do something amazing for entrepreneurs: they will be there for you when you need them but they are humble enough to step back when they don’t know/understand something and they will be transparent about it.

Why a mentor is so important is something for another post 🙂

The extra mile

Credits: Mylene.Savard @Flickr

I always struggle with people that think that great and very unnatural things can be achieved by following old and tested rules, like if everybody could do that simply repeating a playbook. In Europe, we tend to think this way more than in other areas of the world, and ultimately I think the US are the ones that master this better than anybody else. While I write this I am thinking about business and entrepreneurship, but this is true in a lot of other human contexts.

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Lions, founders and large companies

This piece from Paul Graham is just a great read and a beautiful way to start thinking about your career and why you don’t necessarily need to work for a large company. Also, a great read for founders.

I particularly love the reference to building confidence for founders, it all starts there when you decide to build something 🙂

All the difference in the world

  1. I am reading “Dear Founder“, a great collection of letters for founders by Maynard Webb, a famous investor and board member who spent years working with the best companies and founders in Silicon Valley. I had the pleasure of meeting him a couple of years ago at Vertex Ventures.
  2. A friend of mine just posted this on Facebook. There is no better way to express it. I copied it here.
  3. A few weeks ago a young entrepreneur asked me “Who should I hire in my company in the early days?

All of them are connected to one crucial thing I learned the hard way. Continue reading