EP 08: Challenging Culture and The Underdog Path with Chris Howard

Chris is a Harvard University & MIT alum with 6 startups under his belt. His first tech company, Libboo, was founded in 2009 to help authors succeed without the need of major publishers by leveraging the psychology of advocates in getting their content out there. In 2013, Chris then led the launch of MassChallenge UK - a non-profit startup accelerator supporting high-impact entrepreneurs globally - helping founders of companies who 'think differently' and aim to create progressive change within their industries. A few other less interesting companies later, Chris is the co-founder and CEO of The Rattle - a re-imagined hub for artists, technologists, and creatives to help these talented inventors of cultural change become successful founders of their own creative companies. Chris is also an active investor and speaker supporting the 'underdogs' in their industries.





  • When everyone says this is the way something should be done we are always supposed to be the annoying child and say: why?
  • If someone says this is what’s right I would always be the annoying person that says why?
  • What’s important is not subjective, to society it’s important or it’s not.
  • I tend to define culture as society’s voice. It’s the voice of the underground, of people’s beliefs combined. And you must challenge people, ask them, are you adding to that voice?
  • Challenging culture is challenging why somebody thinks it’s cultural as opposed to challenging culture itself.

Culture should be the voice that asks those questions of everyone, are we being good on behalf of society as a whole?


  • Culturally important it stops someone in their tracks, you’ll make something that pauses someone’s attention and they go ‘wow’ I never thought like that before. That doesn’t mean that they agree with it but it challenges somebody’s attention, challenges somebody’s belief that the world’s static and says perhaps the world is changing.

The top three things I would like any underdog to at some point in their lives to embrace are:

- Talking to people shouldn’t be painful; learn to have a conversation.

- Celebrate what you are fucking amazing at.

- Don’t do things by yourself.

These are the 3 questions I ask anyone who wants to start a similar journey to mine:

- Are there a group of people you really care about that aren’t being helped right now?

- Is there something you can do not many other people can do or something you know not many other people know?

- Are you prepared to work really hard and manage but never chase enormous risk?

  • Underdogs need to know that there’s a group of people out there that they feel they can professionally help in some way, shape or form and they bring something very unique to the table. You have to be amazing at something and if you can point that amazing thing to an unsolved problem, even if it’s not obvious, you have the beginnings of an incredible startup.
  • You have to get comfortable with people not liking you.
  • Being scientific means I look at evidence before coming to a belief. There are two principle ways people come to a belief, the first is they will use their intuition to form a belief system and then they will look for evidence to support that belief system; the second is the scientific belief system where you create a hypothesis, where you create a test, and then you use the evidence of that test to form the basis of a belief.
  • I will try my absolute best to never internally believe something unless I have see the evidence for it.
  • I’d very happily form theories and act on those theories if I can’t find evidence.
  • There’re two principles in psychology that many founders fall into a trap off: cognitive dissonance and confirmation bias.
  • You have 40 to 60 seconds to make a first impression and it’s really difficult to change it after that.
  • It’s not how sociable you are that matters, it’s about how valuable you are. Do something that other people can’t do.
  • The second you start helping others to not make the same mistakes you made it feels fucking great.
  • All of us we are not that different from an intellectual and a capability point of view. We are born more or less with roughly the same capabilities. It’s how we are nurtured that really matters when it comes to developing the superpowers.

You have to be fascinated with something, utterly obsessed. Find that thing you are obsessed with and become brilliant at it then use that skill to solve a problem that hasn’t been solved.


Connect with Chris:




The Rattle




Share this post

Leave a comment

Note, comments must be approved before they are published