#18 Gary Stewart

Founder & CEO at FounderTribes, Advisor at Included VC. Ex employee #2 & Director at Wayra (Telefónica's innovation hub with 185+ investments & $1B+ total portfolio valuation)

We are Pol Fañanás and Gerard Garcíatwo friends passionate and curious about tech, startups and VC sharing high-value views from people creating the future. Thanks for reading!

Gary Stewart is Founder & CEO of FounderTribes, an EdTech platform that helps founders to unlock finance and revenue.

He is also member of the Board of Advisors at Included VC, Venture Capital Fellowship created to empower diverse outliers with potential of having significant professional and social impact in the world of venture capital and entrepreneurship, through tier 1 education, mentoring and access by the hand of great supporters of the initiative such as Creandum, M12 Microsoft Ventures, Notion Capital and Seedcamp, among other names totaling $3.5B+ AUM and 320+ exits.

Previously, Gary was an early employee and Executive Director at Wayra Spain and Managing Director at Wayra UK, innovation hub of Telefónica (public listed world-leading Spanish multinational telecommunications company with $49B annual revenue in 2020 and 113k+ employees). At Wayra, he focused on creation and scale-up of startup acceleration activities in Europe and Latin America, investing in 185+ projects that got to reach $1B+ total valuation.

Before Wayra, he was an Associate Professor, Entrepreneur in Residence, and Venture Lab Director at IE Business School. And before that, he was the Co-Founder & CEO at Nuroa Internet, a real state search engine that raised $4M funding and got sold to vertical search website operator Mitula Group, which in turn got sold for €118M a couple of years later.

Gary is originally from Jamaica but grew up in the Bronx, where as a kid he took a test and got into one of New York’s City’s top magnet schools, The Bronx High School of Science. After graduating as a debate champ and president of his high school, he attended Yale University, where he graduated magna cum laude, Phi Beta Kappa and Yale Law School, where he was an executive editor of The Yale Law Journal and published an article that has been cited 178 times.


  • 👤 Brief intro: Jamaica, the Bronx High School of Science, Yale, investor, founder

  • 🥇 Win: think of yourself as a startup, do what you love

  • 🚫 Fail and lesson: 1st co failed, 2nd co exited, failure is an opportunity to learn from your mistakes and improve

  • 🚀 Ideal founder: good risk equation, build a great team, be a little bit ruthless

  • 💸 Ideal investor: real-world operating experience

  • 📈 Markets: new categories in health, education, environment and cybersecurity

  • 🦄 3 startups: Stacey Abrams, Impossible Foods

  • 👍 3 investors: Chris Tottman, Reid Hoffman, Anne Wojcicki

  • 📖 3 books: more constant diverse info sources like NYT, WSJ and Masters of Scale

Could you give us a brief intro about you and your origins?

Born in Jamaica and raised in the Bronx, New York. There I got into one of the few Magnet schools at that time, after passing the required tests.

I studied at Bronx Science, a public school in a tough environment but a really good one, with even some Nobel Prizes as graduates.

I did not interact with many white people before but eventually I found I could do well in those type of communities. I became a debate champion in New York while in High School and managed to go to college. Specifically I got into Yale University to study Political Science and it went well, with stuff such as debate competitions ending up being really useful, and ultimately obtaining some really good grades and graduating top of the class as Magna Cum Laude. Following that, I started at Yale Law School, one of the most competitive law schools in the US.

I was on the right track, the Obama track, except for one small detail - I was gay. In New York there were too many expectations and pressures and I wanted to be free, to live. So I moved to London after law school. But London was too cold and wet, and I met a Catalan partner from Barcelona, got to know really good weather, nice people, good food and good quality life, and I convinced my law firm to be sent to Spain to do M&A, IPOs and securities projects.

After 4 years I came back to London and launched a startup. My first one was a real state business with presence in Spain, but we had a bad business model with no recurrence and we ended up failing for a variety of reasons. Then I started an online real state search engine in 2005, raised more than $4M via public and private financing and sold it in 2009, after the Spanish crisis affected real state heavily and we overcame significant challenges.

Back in Madrid I joined IE Business School as Associate Professor, Entrepreneur in Residence and Director of the Venture Lab, working in how we could push entrepreneurs in Spain in order to build global projects. There I had the chance to be close to great influences in the Spanish ecosystem, invited corporates like Telefonica and asked them about innovation, talked on panels and events, and everything around that.

One day, Telefonica came and asked me to come to a place where they were going to start Wayra, first Madrid and then Barcelona, and I got offered to be employee number 2 at Wayra. I joined them in 2011 as Executive Director until 2014, when after a successful kick off, we realized there could be a relevant opportunity in the UK that was being overlooked. “American and English native speaker? Just go there”. And I did.

I became Wayra UK Managing Director and we expanded Telefonica’s accelerator for digital startups, invested in 185+ projects and played a role in creating $1B+ in total value.

However, 2019 arrived and after 9 years at Telefonica I was not clear about what the future held for me. I was nothing else than the innovation guy, but I am American and I need constant growth. I did not see that opportunity where I was and I realized it was time to go.

I left and created a new company from my lessons of working as a founder and as a corporate. Right now, with FounderTribes, I am working on an innovative learning platform empowering founders to raise capital and upskill their business. Why now? It is a space that avoided disruption and we can do it better.

What would you say has been the biggest win in your life?

As my great mentor Jesus Encinar once told me: “You won’t last 2+ years at Wayra. Good salary, big brand, good lifestyle, but is it your passion? Always do what you are passionate about.”.

At FounderTribes, I took a huge pay cut, travel a lot less, and don't have a personal assistant, but I love being the owner of my own destiny and working every day to solve the problem I think I was sent to this earth to solve -- that is, leveling the playing field for all entrepreneurs so that both talent and opportunity are equally distributed. 

There was a professor at IE who helped to shape my view of my career. Reid Hoffman would later articulate the same idea and call it "the start-up of you". In both cases, the idea is to think of yourself as a business. You are the owner of your own fate, so you need to take ownership and control of your career. You are your most important asset. Your client might change, whether it is IE Business School, Telefonica, or even your own startup, but you always need to be clear about how you are creating value, help others to understand your unique selling proposition, and ensure that you are always evolving and adapting so as to not become irrelevant.

I am my own startup. Working for other people is not a safer option. The idea of job security is an illusion. You've simply given other people control of your fate

Related to the above, and your biggest failure?

I reflected a lot about this in my life.

Failing in Spain was painful. The system seems to assume that “everybody is a crook, so you have to catch them and make it hurt”. That approach inhibits entrepreneurship if failed founders are never allowed a second chance because your company's liabilities become your personal liabilities. A failed founder can be treated worse than a convict. And until recently, there wasn't the same upside potential for risk-taking entrepreneurs as in other markets. So failing in Spain as an entrepreneur was particularly painful, and it was meant to hurt.

The lesson? Failure of a company and failure of a person are 2 different things. If someone has the guts to dream big and set up a business, but it fails in its first iteration, the person should be encouraged to try again.  Twitter's founder, Jack Dorsey, failed multiple times before getting it right with Twitter and then Square. The co-founders of Skype failed multiple times and shared a flat with their wives before succeeding with Skype. That's the way entrepreneurship tends to work. Success is an iterative process of trial and error, but errors can't be insurmountable because the system punishes and disincentivizes risk-tasking or entrepreneurship. 

We should avoid making failure so painful on a personal and professional level and pushing institutions to lower penalties for failing, if the goal is to create a generation of European companies that are able to compete with Google, Facebook, etc. 

What is your ideal founder profile?

After being a founder, with 1 failure and 1 exit, I’d like to highlight a couple of lessons.

First, don’t take all the risks by yourself. Don’t be stupid. Come to the table with an idea, passion, ability to be persistent, resilience, overcoming obstacles … Know in advance that the process is going to be painful and disorienting, but limit the risk to your family, kids, etc. Mitigate risks. I’ve been in meetings with other investors telling founders to bet the house to go the extra mile, to get second mortgages on their homes if needed and I was like “What? Hell no”. You should have skin in the game, but you don't need to bet your entire future on a risky idea that statistically is likely to fail. Balance out risks with investors. Most of the time, they aren't really investing their own money and their limited partners have only put up money they can afford to lose. Understand the rules of the game, and don't do anything too crazy. 

Second. Build a good team and be a little ruthless about it. In the past, I think there were situations where I was like a Mother Theresa with people. Truth is, now I believe that if I don’t think you are better than the average person on my team, I have to consider if it makes sense for you to stay. At the same time, reward greatly outstanding employees. As a CEO, my job is to identify talent and ruthlessly get rid of people who are not contributing to winning, because then they are contributing to losing. It is not a question of being a good or bad person, but more about “I need to run fast and you either can help me or hurt me”. There is no neutral option. As Reid Hastings points out, startup teams are more like a sports team than a family, because if someone in your family goes to jail, you still have to love him unconditionally. But a start-up is more like FC Barcelona; if you recruit someone who can not score goals, how long would they stay on the team? If I win to win La Liga, I need the best team in place. I have to be very strategic about it, hire the very best that can accelerate my chances of winning, and always be on the lookout for great talent.

What is your ideal investor profile?

A successful entrepreneur who is willing to share his or her experiences and insights. I even prefer failed entrepreneurs to folks who never had the guts to get in the game, even as an employee in a start-up.

In the UK, 90+% of investors have never worked in startups or in tech, and it becomes increasingly unclear what value can be added to founders other than money, which is still very useful, but not as ideal as money, experience and insights.  Folks with backgrounds at consultancy firms like McKinsey can be brilliant, but there is nothing like actually having done something before you try to advise others on what they should be doing themselves. For example, I would never go to a doctor who had never studied medicine or previously operated even on cadavers. As a lawyer, I studied at Yale, but to really learn how to be a lawyer, I had to practice as a junior associate in top law firms. I don't think you can learn entrepreneurship from reading a few blog posts or watching a few YC videos. I'd prefer someone who can relate to and support me based on real-world experience.

In the US, the majority of VCs have some type of operating experience and you can see the added value, people like Reid Hoffman, Linkedin co-founder and partner of Greylock, or Marc Andreessen, Netscape co-founder, doing great things with a16z.

There is a really interesting study from Maddy Cross from Erevena and ex-Notion Capital, where she examines the characteristics of unicorns. One of the key conclusions is that even when two companies raise equal funding at Series A, what ultimately determines success is the quality of the management team - teams with employees with relevant experience in venture-backed companies perform much better than their counterparts, because they know better what they are doing, they have experienced fast growth and that experience materially increases the chances of success.

You can't give advice if you don't really know what you're talking about. I watch a lot of tennis, but I would never think that I'd be able to be Serena William's coach. You probably need to have played the game at an elite level to be able to offer her real value. Similarly, I believe if Europe grew towards that, the ecosystem would see better returns.

What present and future markets are you most interested in?

None. I remember watching Larry Page in 2002, pre-Google IPO, being asked tips for entrepreneurs. One of his replies was do not follow VCs, because most of them will tell your project is good only if it fits into a space they currently see as sexy .

My advice is that founders should solve problems they believe that they are uniquely capable of solving and that it's better to try to change the world while doing it. Don’t get influenced by trends and don't get dissuaded by naysayers. We founders are the crazy ones that believe we can see the world a few steps ahead, kind of like expert chess players. We don't always get it right and need to be humble enough to analyse feedback and learn from our mistakes. But that is not the same as blindly following the advice of people who can't see what you can see. If they could do what you could do, they'd probably be entrepreneurs themselves, and most of these naysayers don't have the courage to even try. 

With all of that in mind, I really like founders trying to address big problems. Healthcare, education, cybersecurity and environment are 4 examples of those. Spaces where we, as species, have huge problems, and we need our most brilliant, entrepreneurial minds to help us find the solutions. 

Could you share with us 3 startups you like and why?

  • Stacey Abrams. As I mentioned earlier, from the premise of a person being her own startup and entrepreneurship beyond the concept of Silicon Valley, I find her great. She saw a problem in getting minorities into politics by ensuring that all citizens have equal access to the vote,  and she devoted her life to solving this issue. Sometimes, she uses politics, sometimes she uses non-profit organizations and sometimes she uses for-profit entities, so the “how” can vary, but she's a great friend, and I find her trajectory and approach really interesting. She lost the election to become the first black female governor of a US state in 2018, but she didn't despair, she just founded a non-profit to protect voting rights. She didn't allow failure or naysayers to get in the way, and in the process, she has maintained control of her own destiny.

  • Impossible foods. A good example of how false it is that only young people can be founders. A biochemistry professor launched a plant-based meat start-up at 57. Experience cannot be discounted or undervalued. He's now raised more than $1.4 billion. This is a situation of a clear and powerful idea, a really smart, passionate person, great execution and big, global problem. Stories like this inspire me, especially when founders can disprove the myth that you can't be both mission- and profit-driven. A desire to change the world doesn't mean that you have to be poor. I grew up in the working-class Bronx.  I'm not trying to go back. I want to change the world, but I also want to make some money in the process. 

Could you share with us 3 investors you like and why?

  • Chris Tottman. My favourite. Investors can be scary. At Wayra I talked with a lot and one day I reached out to him, he said to grab a coffee and he told me his story - vulnerable, transparent, authentic. He said to stay in touch and I was OK but that never happens in the end. Yet he kept in touch genuinely. Eventually we formed a Whatsapp group, then I connected with Nikita and got more involved in Included.VC. Chris invested in FounderTribes and became an advocate of me. He has done well and he continues to do so, but he is also a driving force for others. He's an example of a good person who has worked his way up from humble origens to find tremendous success. I like the Chris Tottman model of changing the world and realizing that if you're not part of the solution, you're probably part of the problem

  • Reid Hoffman. I admire him a lot and got hooked on his story, mix of entrepreneur and investor as well as side hustles like the podcast Masters of Scale. He's a billionaire founder who still loves entrepreneurs and genuinely gives back, not like “I made a lot of money and screw everybody else”. Member of the PayPal mafia, founder of LinkedIn, great investor with Greylock, and still giving a lot back with Masters of Scale, sharing high-quality insights - it's a great public service! I believe we need more of this type of profile in Europe, we need a bigger culture of paying it forward.

  • Anne Wojcicki. Founder and angel investor. When I spoke to her, it became clear that despite all the privilege you might associate with her being the ex-wife of Google's co-founder, Sergey Brin, and despite her own success as the unicorn founder of 23andMe, she still seems like she is just getting started. She pays it forward, because she is driven not by money but by a genuine desire to change the world. She is endlessly curious and action-oriented,  with a big focus on solving relevant problems and a willingness to put her money where her mouth is. She was so down-to-earth and relatable. It was a genuine pleasure to speak with her.

What are the 3 books you feel everyone should read and why?

I won’t recommend any books.

I remember when I started at Yale Law School, I was so impressed by Michael Farbiaz, easily one of the smartest people I had met at that point. I asked him: "How is that you have an informed opinion about almost everything?" He said “I read lots of newspapers every morning.”

Since that day, I followed his lead. I wake up early and I read a bunch of newspapers. I focus less on tech that on life in general. I believe intelligence is connecting the dots that other can’t, and to do that you need to be able to see the dots, to know that they exist. In that sense, it's useful to be aware of what is happening in the world. Then your brain starts making connections, you start being able to process lots of info and synthesise it properly, and the more sources of information, the better.

So I’d recommend:

  • Newspapers. Be aware of current events and read newspapers.

  • Podcasts. I try to walk 2 hours a day and listen, make connections, allow my mind to free associate.

  • Movies, tv, music. I draw inspiration from movies,  tv, art and culture generally. Always question everything. If I watch a movie, I try to understand why the director wanted to tell this story and why audiences reacted to it. You can learn from almost everything. 

Multiplicity of sources is a great asset, from technical stuff to pop culture. From NYT to The Wall Street Journal to El Confidencial. I believe there is still amazing potential in traditional journalism, even as the model has suffered as news has become entertainment and click-bait.


Why is diversity important and what can we do to improve it?

I recently read a story …

8-year-old homeless refugee from Nigeria wins NY State chess championship beating well coached, private school kids, readers donate $250k and a home to his family and now he is a national chess master and Paramount Pictures has optioned a movie about his life”.

Talent is equally distributed, opportunity is not. We need to work on giving folks equal opportunity, which is the real passion behind FounderTribes.

Another example: Jay Z was an ex-offender, deemed by some as a failure of society. Now he is a billionaire changing the world. If you write people off because they don’t look like central casting. 

And it's not just anecdotal instances like these two. Research from well-respected companies like McKinsey prove how business with great diversity are significantly more profitable. Ethnicity, sex, socioeconomic background - you name it. 

I am a Jamaican immigrant from the Bronx and yes, I have faced people that care too much about my race or other demographic traits, but I've also led an incredible life. It is in all of our interests to work together to make the world a fairer place, where your success is based on how hard you are willing to work, not on race, geography, gender, ethnicity, religion, sexual orientation or anything similar. I created FounderTribes, because my passion is to use technology to level the playing field for all founders so that we can stop throwing away so much human potential for what, in the final analysis, are really silly reasons. 

Big thanks Gary for sharing your views with us !

Big thanks to you, reader, for your time and interest !

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