Exactly 6 years ago, in October 2013, I got a new job. Well, two jobs actually: I became a digital communicator and events manager at How To Web and TechHub Bucharest.

That’s how I got hooked on the world of startups. 

At How To Web, I got to learn from and work with some of the best people in the ecosystem – investors, founders, mentors, and all sorts of specialists. What fascinated me is that working in a startup and creating a business from nothing pushes you to learn, to work, and to think differently. 

I was never into the hustle culture often associated with working with startups, which is why I loved working with the community at TechHub Bucharest. It was a completely different environment and I got to witness and contribute to the development of the local and regional startup ecosystem.

It was an intense personal development experience for me, one that I’m very thankful for.  

From there, I went on to work for startups and now, as a freelancer, I work with startups, the kind built on solid foundations by people who I respect and learn from every day. 

Throughout these years, I’ve stayed close to the How To Web community and today I have the opportunity to share with you the decision-making process of a startup investor.  

Listen to this episode to learn:

  • The know-how of coaching and what it takes to support people to achieve their goals
  • How commitment can “move mountains” if you have patience and choose your “game” wisely
  • How we can develop multiple intelligences and why it’s helpful to do so
  • How Alan became a startup investor and why
  • The importance of personal values, identity, and branding to successfully achieve any goal.

About Alan Clayton:

Alan Clayton, my guest for this episode, is a Roaming Mentor at SOSV. He’s spent the last decade coaching founders from across the world. As part of the SOSV team, Alan invested in over 800 startups globally, having met thousands of founders.

To help them build businesses that make a real positive impact on the world, to challenge their thinking and become more than just managers to their teams, Alan developed the Wholebrain Methodology .

With a strong business and marketing background, Alan became a coach to give company founders a truly helpful hand. He’s very dedicated to solving the human part of any issue. Not only does he believe in multiple intelligences, but he also calls attention to how important it is to give people an alternative perspective.

As humans, we tend to be very subjective and it’s built into our genetic makeup. People need someone who can take a step back and see the problem with less emotional involvement. A good coach sees the issue objectively and gives you perspectives you didn’t even think existed.

Talking to Alan was a privilege and I hope you’ll listen to his words of wisdom with intent. Even if you’re not a startup founder, there’s just SO much to learn from him!    

Here are some of the concepts and ideas from our conversation that inspired me to reflect and dig deeper. 

“We develop favorite types of intelligence”

Alan mentioned the work of Howard Gardner, developmental psychologist, co-founder of The Good Project at Harvard, which encourages excellence, ethics, and engagement in education, and Senior Director of Project Zero, an educational research group at the Harvard Graduate School of Education dedicated to understanding and enhancing learning and thinking.

Howard Gardner is best known for his theory of multiple intelligences (extra details on Wikipedia and in this summary), which makes for a fascinating read. 

As a big believer in coaching and its very real results, I asked Alan how he uses his background as a coach to help startup founders grow and make increasingly better decisions. 


“Coaching helps people reengage with some of these types of intelligences that they may not use as regularly as they could.”


There’s a lot of mimeticism in the startup world 

Another key concept Alan touched on is René Girard’s mimetic theory

I found this Stanford Magazine article about Girard to be intriguing which made me want to read more about this theory and its implications: History is a test. Mankind is failing it.


“Girard’s theory—a long thought played out over decades—suggests that mimesis is the basis of all human conflict, and that the resolution of conflict through the public sacrifice of a scapegoat was the very foundation of archaic religions and civilizations. But the ancient formula no longer works, he says. The world may be headed for an impasse.”


One of the things Alan works to help founders is help them understand how the short term skews perspective and how it impacts the medium and long term. 


“In the startup world there is this built-in sense of urgency to create success or at least to create financial return, so trying to inject a little bit of patience into the system is difficult.”


To do this, Alan tries “to offer startups some kind of experience away from just working on their project.” This distance is one of the key ways to cultivate long-term thinking, something humans find difficult because we haven’t done it for a very long time. 


“People often have a strange idea about how their work life is separate from their home life, which I think is a bit bizarre because what I do at work has a huge impact on everything I do outside of work and vice versa.”


This reminded me of James P. Carse’s book, Finite and Infinite Games, which I highly recommend you read. 


“In the startup world, really all you have to play with is your money and your time. And the truth is that you could probably get money but you certainly can’t get more time.”

A few ideas that stuck with me:

  • A good coach takes a step back and helps others look at their problems from a different perspective.
  • Competition is a core issue and we aren’t even aware of it.
  • Most people focus on the short term and this is the cause for the many unsolved problems in the world.
  • When we start investing in projects, we should focus on those critical problems – hunger, the lack of water, and medicine.

How Alan became a startup investor

Alan’s candid account of how he became a startup investor will give you the real-life version of the story. 

He’s not afraid to point out the faults in the ecosystem, calling attention to the fact that the startup world is often dominated by short term interests and greed. 

Listen to the episode to find out how the industry is admitting its problems and some ways it’s trying to solve them.

“Some things just take time”


“Young people struggle to believe they can make a real impact in the world.”


When Alan said this, it instantly echoed my personal experience and I think the same may happen to you. 

Realizing we need to solve real problems takes time, as Alan says. That’s why the average age of founders in SOSV programs is higher than it used to be 10 years ago, reaching 35+.

His experience of working with startups and having spent the previous decade coaching people in large organizations taught Alan that: 


“It boils down to a small group of people with a vision and a massive commitment to deliver it.”


He reminds us of this famous quote from  cultural anthropologist Margaret Mead:


“Never doubt that a small group of thoughtful, committed citizens can change the world; indeed, it’s the only thing that ever has.”


“There’s nothing you have to do”


“Things seem obvious but only in retrospect.”


With that in mind, Alan talks about neurological levels in NLP and how they can help us constantly assess whether the destination we’re heading towards is what we want for our future selves, irrespective of our current job/role/situation.

This is key for better decision-making and for ensuring the legacy we create for ourselves is one we’ll be grateful for 5, 10 years from now. 

This was a delightful episode to record and I’m thankful to the current How To Web team for making it happen! 

If you want to learn more from Alan Clayton and a bunch of other fantastic humans beings (and truly impactful leaders and specialists), join me at How To Web next week

I’ll be there, soaking in wisdom and striving to apply it every day.

Connect with Alan Clayton:

Resources mentioned in the episode:

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