The Opposite Of Weakness Is Vulnerability

LinkedIn has turned our careers into beauty pageants. The truth is that entrepreneurship is really hard. Each week I share my experience, strength and hope with a strict no bullshit policy. I hope it empowers others to be more authentic and empathetic. It’s tough out there - but it’s easier when you go through life as your whole self. 

In this first column I share some guiding principles of my life and work as well as some vital stats about who I am. 

If you’ve heard of me it’s probably because of my book or my prediction. I wrote the book This Might Get Me Fired which shares my journey from startup entrepreneur to Wall Street intrapreneur. That book inspired a cult following of bold, punk, empowered badasses to move mountains. They’re my heroes and I love them. Twelve years before my book came out, in 2006, I made the first public prediction of the 2008 financial crisis. Because of that prediction I was one of those pundits that you see on CNBC and in the Financial Times talking about stocks. In 2009 my startup Innovest got acquired, and I made the tough transition from entrepreneur to employee. My job title is usually something like product strategist, innovation director, or business designer. Over the course of my career I’ve launched over thirty digital products at Google, Uber, Bloomberg, Nestle, PWC, and many other companies. Some of them worked, lots of them failed, I’m proud of them all.

New York’s my second wife, Pauline’s my first. My beautiful Scottish wife, Pauline often gives me shit because of how much I love NYC. I grew up in Queens in the ‘80s and still get nostalgic for when New York was a hellhole. Punk, old school hip hop, and rows of abandoned buildings make me feel oddly warm and fuzzy. I gravitate toward people who are unafraid to share their raw truth - even when it’s ugly or uncomfortable. And I get a rash from pretense and posturing (which makes it hard to be a public speaker sometimes). I attribute those qualities to the city where I grew up and still live. 

The opposite of weakness is vulnerability. I have spent much of my entrepreneur life launching new products in companies run by an older generation of men. These companies often have all the technology that money can buy. But they don’t have a language for the pinstripe executives to connect with the punk entrepreneurs. There’s a generation of executives who came up during a time when power was synonymous with invincibility. Their dads fought in WWII. They hand down directives and KPIs and strategic goals and demand that they be implemented. That might have worked on a Ford assembly line - but it backfires in the disruption economy when new startups reinvent the rules every three months. Leadership today is having the courage to admit that there’s a big problem and you don’t know how to solve it. It invites entrepreneurs in your company to step forward and do their best, most creative work. There’s tremendous untapped power in vulnerability. If you hear a CEO calling themselves an entrepreneur or talking about innovation - and they’re not sharing their own vulnerability then they’re probably lying (to themselves).

True Thought Leaders Are Survivors Not Superheroes. We live in a time when expertise can be manufactured and not earned. Many of the “thought leaders” on leadership, innovation, and entrepreneurship haven’t led or invented anything other than their own brand. Social media amplifies their false prophecy, and millions of people who need actual help start holding themselves to a false standard of performance. It screws with our egos, our ability to be authentic, our ability to form real connections with others. And it means that millions of people take on work work based on their number of followers rather than a real understanding of their true strengths and limitations.

The thought leaders who can actually help are harder to find. They are survivors - not superheroes. Fast Company and Forbes doesn’t know what to do with them. They’re still doing the work of building new things and changing old things and therefore they still get knocked down. They share how they get unstuck. Stephen Gates, Josh Higgins, Joe Toscano and Jody Medich all come to mind.

I want to use this column to amplify their message, and make it easier for the people who need their help to find it. (If there's anyone else who belongs on the list please let me know.) Maybe the term for it is indie thought leadership. It’s intentionally raw - therein lies its power.