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 🙂

Looking back

2018 has been a tough one. I learned a lot, not always in the gentle way I would have loved to 🙂 It looks like 2019 will be as challenging as 2018, hopefully in new ways. I am not a huge fan of this kind of posts, but I have been thinking about what I learned in the last months.

The ability to trust my gut, to follow my will even when everyone told me I was going in the wrong direction. This way of looking at things has always been part of me, for some reason I lost that a bit in 2018, at times I felt I had to stay within the limits, for something, for someone at times.

Looking back, I can feel how much I missed that. It’s been a great lesson, 2018.

Will Artificial Intelligence impact the cloud?

A candidate asked me this question yesterday. “How do you see artificial intelligence impacting Cloud Academy?“. The short answer is that I don’t have a precise answer but I think businesses like Cloud Academy will define a new category in the enterprise business software. Let me explain why.

AI is already impacting cloud and infrastructure management, and that will grow in the next 2-5 years: most of that is already happening for AWS or Microsoft Azure within their managed services (think Amazon RDS), but I expect that to be the norm for every type of infrastructure, private or public.

But Cloud is much more than infrastructure today, cloud computing is how companies build and operate their software and services. If you are a junior developer today you will likely start building your application using something like AWS, Google Cloud, Azure or Salesforce and your application will be deployed on these ecosystems. Today, the common enterprise cloud stack is already quite complex and it goes from infrastructure to SaaS, with several layers that need to communicate to each other and need to talk to your legacy systems. Keep in mind are still living in a world where a bit more than 10% of software is SaaS, there is still a lot of legacy stuff running in private data centers ready for disruption. So what’s AI role? It will likely help companies to automate more and more in their infrastructure and we will see several titles disappear forever, think of database administrators, sysadmins and storage administrators  but ultimately enterprise companies in every industry will keep hiring more and more software engineers as the real challenge will increasingly be about creating competitive digital solutions for your own business, building on top of hundreds of frameworks and vendors that are providing resources and APIs to do it. 

In this context, companies will have to not only invest billions in developing and updating tech skills for their teams, but they will also need to have a platform that allows them to collect data, insights and understand skill trends in their IT organizations. That’s why we keep building Cloud Academy focusing on technology first, our final goal is giving enterprise companies an Operating System to manage technology skills, at scale. 

LinkedIn has a nice report on how AI is impacting the job market and which positions are getting hurt by artificial intelligence. Nice read. Stay tuned….at Cloud Academy we are close to releasing a nice set of tools to understand a bit more how the cloud computing jobs market is changing 🙂

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