Why Operating At The Edge Of Legality Is The Best Way To Become A Billionaire

But you might get yourself arrested along the way…

Chris Herd
4 min readJan 31, 2018


Just ask Sean Parker!

When looking for ways to innovate and disrupt I look towards opportunities which straddle legality. I seek the things which visionaries are working on that are so far ahead of their time there is no regulatory framework to govern the evolution of what’s occurring and explore the possibilities that arise.

The best ideas generally look terrible at conception due to the obstacles they must overcome to achieve success. To build innovative and revolutionary products or services you need to be pursuing things that are counter intuitive and often things which appear to be destined to fail or aren’t legally permitted.

When I say ‘aren’t legally permitted’ I don’t mean things which are illegal. I mean things which there is no legislation against but know you are operating against the spirit of what the existing legislation says is permitted.

I find what is currently legally permitted and explore the consequences of taking that a stage further

In many way’s the biggest evolution’s that have occurred in recent years have happened because of this. You see the rise of Uber and recognise that it was operating on the border or legality in every jurisdiction. The taxi industry is a heavily regulated and scrutinised industry for obvious reasons — the public interaction — but Uber thought they could provide a better service at a lower cost to the end user.

So they just did it

It’s far better to ask for forgiveness having done something wrong than to ask permission and wait for it to come not knowing whether it ever will

Airbnb done exactly the same thing. The blow-back you are seeing now in relation to companies operating in the ‘Gig-economy’ is simply a manifestation of legislators trying to catch up. These companies innovated quicker than the government could keep up.



Chris Herd

CEO / Founder / Coach @FirstbaseHQ Empowering people to work in their lives not live at work ✌️✌