A Letter To Entrepreneurs, From Your Future Self

A Letter To Entrepreneurs, From Your Future Self

A Letter To Entrepreneurs, From Your Future Self

  By Christopher Lochhead, host of the Legends & Losers Podcast 

In short:

  • Way too many entrepreneurs are like a rock band who thinks if they just get good enough, they will be “discovered” one day.
  • But really, much of entrepreneurship’s decline is a lack of category design.
  • Keep at it, entrepreneurs, even though it’s hard. Keep fighting to bring something awesome into the world. Your work is worth it.

Dear Entrepreneurs of the World, 

As corny or bullshit-y as it may sound, your success in life means the world to me. Making some kind of a difference to you is my motivation.

The decline in entrepreneurship is crushing for me personally because I know that almost all job growth, innovation growth and opportunity creation comes from entrepreneurs. I have also experienced the self-actualization of creating the future of my choosing from thin air.

It kills me knowing that a major cause of entrepreneurial failure is a lack of category design. I see it everywhere. Sometimes I can’t take my own brain because I see the absence of category design everywhere, every day. 

A new deli opens up with just a name and a generic category: “Maria’s Deli.” Nothing about what makes it different. Not even a small attempt at a niche down positioning like, “Maria’s Italian Deli” or “Maria’s Authentic Italian Sandwiches & Deli.” And sure enough, Maria’s is gone in less than two years.

My brain screams this shit at me as I drive down the street! 

I know that tons of amazing companies, products and services die because the founder or creator thought that when she put her innovation in the world, the world would “get it” and she’d become a huge success. 

Way too many entrepreneurs are like a rock band who thinks if they just get good enough, they will be “discovered” one day.

But as we know, that almost never happens. “Build it and they will come” is an entrepreneurial belief that is so deeply rooted in so many people that it makes me feel like I will never be able to get people to see there is another way.

My dream is that one day, more people will focus on the exponential value of what makes them different instead of the incremental value of what makes them better.

For me, entrepreneurship was a way out. I had very limited options: My mum was terrified I’d be a bum, so I went for it. Knowing that you’re going for it — fighting to do something awesome for yourself, your family and the world — fires me up.

Writing and podcasting are labors of love for me. I pour myself into this “work” (over the past two years, it has rarely felt like work… I need a new word!) in the hopes of making a difference to people exactly like you.

My podcast, Legends & Losers, is built on real, raw conversations. 

But to be candid, I went to bed last night feeling like complete shit. I’ve been in a Twitter debate with a ding-dong venture capitalist at one of the top Sand Hill Road firms who believes the best product wins. The amount of Twitter support for his POV versus mine was shocking: I had forgotten how much the world really believes the best product wins. 

I said to my wife, “What the f*ck am I doing at 50 years old, fighting this battle? I should just f*ck off, relax, have fun surfing and fight training and f*ck this ‘work.’ ”

Sometimes I feel like I'm trying to explain that the world is round to people who “know” the world is flat. These product guys (don’t get me wrong: I LOVE great products and have helped to build many) are so busy stroking their Stanford engineering degrees that they can’t hear anything.

So for what it’s worth, entrepreneurs, you and I are doing the same thing at the same time: Trying to introduce the world to a new and different idea. And f*ckineh, that can be tough.

Tough as it is, I know the joy of making a category “tip.” Of knowing that you were part of bringing something legendary to the world. That’s what you’re doing, entrepreneurs. And that is f*cking awesome!

THANK YOU for having the courage to be legendary.

For being willing to slay the cynicism of our times with your dreams.

For being willing to risk being a fool in public to make something amazing happen.

Stay legendary!

Your friend,


Christopher Lochhead is a retired three-time public company CMO (Mercury Interactive, Scient, Vantive). Over 30 years, he co-founded three consulting firms and invested in over 50 Silicon Valley startups.

Christopher hosts the Legends & Losers Podcast, featuring real and authentic dialogue on life and business. He’s also coauthored the soon-to-be-released book Niche Down: How to become legendary by being different. He’s father to six chickens.