How Startups.co Became My Dream Job

Here’s the short version:

I created Startups.co as my dream job. There wasn’t any magic to it – but I had to be painfully honest about how I really wanted the rest of my life to play out.

This is how I did it.

Imagine this: as of today, you are now working at your dream job.

What would that look like?

Get really detailed with it: How would every hour of the day go? What would you get to do? What would you never, ever, ever, ever have to do again? Have you written all of this down and made a plan around it?

Yeah, neither did I – for about 18 years in a row.

And then I did, and it was the most profound and relatively simple change I ever made. So much so that I have dedicated the rest of my life to helping my fellow Founders align what they care about with what they do for a living.

The process took some time, and it may take you a few iterations, but I can promise you it will be the best investment you ever make.

First, a Quick History

In 1994, I started one of the first interactive agencies – Blue Diesel. Since then, it has merged so many times with so many entities I don’t even recognize it. What I do know is that when I started I thought that if the agency ever became “big” I would have my dream job.

The agency did in fact get big. We grew to about $650 million in billings in over 5 years with 600 employees worldwide. We did all of those things you dream your company would do some day.

So at that point I should have had my dream job. I should have been super-mega-ecstatic-happy-guy right?

Nope. I walked into work one day and thought, “I hate my job.”

At the time, it terrified me to say that. I was 27 and had accomplished far more than I ever thought that I would, and yet at the finish line of my dreams I was plagued with dissatisfaction. I wasn’t unhappy or depressed, I was just deeply dissatisfied. And it pissed me off.

So I Tried Something Else

Thinking that maybe it was just the agency business that was boring me, I tried something else. Anyone who knows me knows that I’m just a manic ball of ideas, so I thought maybe the issue was just that giving all of my ideas away to clients was the problem.

A year later I started an incubator to launch all of the random ideas in my head. We launched 8 companies over the ensuing decade, and although doing totally new things was fun, I still didn’t find myself to be truly satisfied.

Now I Was Really Frustrated!

At this point I had burned nearly two decades of my life and had 9 shots on goal with starting new companies only to get to the same crappy conclusion of “OK great, now this choose-your-own-adventure leads to me getting eviscerated by the Platinum Dragon as well.”

 

I wanted to just figure out a way to skip to the end to figure out how the story plays out.

Transition Time

So, at the tender age of 37, I sat myself down and said, “Enough is enough. I’m not exerting any more energy doing anything until I figure out exactly what it is that’s keeping me from being satisfied.”

Being a serial startup Founder, I did what I do best when faced with a problem: I took to the whiteboard and started writing furiously. I figured I’d be there for at least 2 hours.

I was there for 2 months.

 

My tendency to get a little OCD can be a superpower or a curse. In this case, I was devoting every waking moment to writing down potential directions to expend my energy. I thought about starting a charity, or making video games, or shrinking my costs to zero and adopting a bohemian lifestyle.

I spent hundreds of highly caffeinated hours thinking about this challenge. What I finally boiled it all down to were two big categories:

1. What I Never (ever ever ever) Want to Do Again

2. What I Really Care About

This is where things got interesting for me.

What I Never Wanted to Do Again

When I talk to Founders who are thinking about what they are going to do next, I often ask, “What don’t you ever want to do again?”

This is a lot easier to react to, because we can readily identify things in our life that just suck. And the thought of never having to go through that pain again brings us all so much relief.

I wrote down dozens of quips, frustrations, and annoyances. The list got really long – not because I’m so easily annoyed, but because I personally spend an inordinate amount of time internally deconstructing my emotions.

I distilled my thoughts into three primary themes. I also learned I like to number things and put them in convenient thematic buckets.

Theme #1: I never want to answer to anyone else.

I suck at being told what to do.

It’s the genesis of everything from my awful academic career to only really being able to work for one person: myself. The irony is that I love to get feedback and I’m hyper critical of myself. I just don’t like having to answer to someone else.

The agency business brought this out in me. I appreciated our clients, but I hated being in a business where my days were dictated by the whims and emotions of any one client. I had the same experience with having venture-funded companies. I had great investors who were very good to me, but I hated knowing that the entirety of my future was not solely my decision.

This lead to Startups.co being entirely independent. We self-funded the business, which was a hard fought luxury, but allowed us to maintain total control of our own destiny.

Theme #2: I never want to work with people I don’t like.

When I look back at all of the most amazing times that I’ve had in my career, I’ve noticed a few surprising trends. The first is that “good times” were rarely synchronous with “things were going really well at the company.”

Take a look at the photo below. That’s me, sleeping under my desk in the middle of the day while trying to build my first company. I didn’t care that it was difficult or that I was so tired that I needed to sleep under my desk in the middle of the day. I was around awesome people and that’s all I remember.

 

Conversely, what I also remember are the jerks, know-it-alls, annoying cynics, and the fundamentally negative. I don’t have a single fond memory of building a business with these folks, no matter what their contribution or outcome.

I regret now that in the past I developed a very high tolerance for these personalities, because I always believed it was for some greater good. And in reality, I’m sure more than a few people would classify me in the same category – I’m no hot fudge sundae either.

 

Being in the business of starting over—and over and over—I tend to give everyone the benefit of the doubt. But there are some people that are hard-coded to be jerks. They would leave me and go on to every one of their other companies as the same jerk. I vowed that I would do everything in my power to avoid being in their company, no matter what the cost.

So we built Startups.co with a simple cultural goal: work with people we like. The result? 30+ people who absolutely love working with each other.

I love coming into the office because I get to work with people who are awesome. Zero jerks. No politics, no infighting, no bullshit.

We have managed to align people with different views, but are just fundamentally good people who want to get along well. It’s nirvana, and something I wished someone had forced me to focus on 20 years ago.

Theme #3: I won’t sacrifice my goals.

My life up to this point was riddled with sacrifices.

I sacrificed the freedom of my youth to build a company. From the day I graduated high school at 17, until I was about 26 years old, I didn’t take a single day or hour or moment away to do the things I could have enjoyed doing.

 

I sacrificed my time, my freedom, my happiness, my income, my family, my friends, and countless other pleasures in the service of work. While you could call me a vocal proponent of sacrifice, I would counterbalance that by saying at some point you have to have a payoff. Otherwise it’s not sacrifice – it’s just flat out loss.

Therefore I made a single commitment: I will not sacrifice the things in life that I hold most dear. No matter what the opportunity lost, I will find solemnity in the focus toward my goals. It doesn’t matter if it pays more, if it’s easier, if all the forces of the world tell me otherwise; I won’t sacrifice my goals. Life’s too goddamn short.

Of course, it helps to know exactly what those goals are in the first place, which led me to the other side of this exercise: what I really cared about.

What I Really Cared About

It turned out that removing all the things I didn’t want to do was far easier than finding the things that I cared about most.

This radical brainstorming occurred when I was just starting a family, so obviously spending quality time with my family was incredibly important. I knew that whatever I did had to support my focus of “family first” or it wouldn’t make the cut.

But I wanted to go beyond that. I wanted to figure out what I would enjoy doing so much that I didn’t even think I was working anymore. I tried so hard to frame this question so that it actually made sense.

Theme #1: I want to make my workday like a Saturday.

Finally it hit me: “What do I love to do on a Saturday more than anything?” The idea was that given the freedom of a weekend, and nothing to do with retirement or extraordinary wealth, how do I just love spending my time?

As it happens, I don’t play golf or ski or enjoy other leisure activities that involve tying a sweater around my neck. The most enjoyable time that I spend is when I’m talking to other Founders about creating something, preferably with a vodka gimlet in hand.

 

It doesn’t matter what that “something” is. It can be designing the menu of their restaurant, the technology stack they are thinking through or the brand story of their apparel company. I just love the energy that two Founders generate when they are in a creative zone. I wanted to do that all the time.

At that point it clicked. I erased everything else on the whiteboard and simply wrote “I want to be creating with Founders every day for the rest of my life.”

That was it.

It wasn’t a business idea per se, but it was the focus of a business idea which would ultimately lead to Startups.co. What I had been missing all along was a North Star that would simply guide me to where I was supposed to be headed all along.

Theme #2: I want a long view.

My experience has shown me that most Founders are manic, anxiety-laden freakshows like me who are constantly living in fear of the sky crashing. That manic behavior provides some turbo power to our lives that drives us forward.

It also drives us insane.

After meeting with countless Founders, I found that the ones that I had admired the most were those that had a long view of their lives and their companies. I don’t admire the “build it and flip it” mentality, even though I’ve regretfully shared it far too many times.

I didn’t want to run on a hamster wheel of “get big fast in order for something magical to happen later.” I tried that; nothing magical happens later.

I wanted to find a goal and just devote the rest of my life to working on it. In my case, it’s helping Founders get started. That’s what I’m going to be doing for the rest of my life. It doesn’t matter how long it takes, because it’s the only thing I’m ever going to do.

There is an amazing serenity that comes with aligning your life’s work with the long view. It’s very zen. Everyone around me, especially my wife, has noticed that my outlook and personality has changed dramatically by adapting the long view. I am no longer in a hurry for the sake of being in a hurry.

It’s like I’m living a different person’s life, and it’s fantastic.

Theme #3: I want to fundamentally change one thing I care about – forever.

The first two decades of my career were spent building things that were transformational: from designing some of the first Web sites on the Internet to upending business models in everything from subprime credit to casting for television to building enterprise software.

(That sounds even more bizarre now that I see it written down….)

The challenges always fascinated me, but one consistent thing plagued me: I wasn’t working on problems that I connected to on a deeply personal level. They were fun, but not fundamental to me.

At SwapALease.com, for example, we created liquidity in a multi-billion dollar market to let people get in and out of car leases with ease. It solved a painful problem, but I never jumped out of bed saying, “I can’t wait to help more people get out of car leases!”

By aligning all of my time and output toward helping Founders pursue their aspirations I feel I am actually helping to lay the seeds for millions of ideas to flourish. It’s an outcome and a change that I can’t even comprehend the magnitude of.

I really can’t articulate the feeling it brings me, but I can tell you what goes through my head every time I see another Founder become successful: “F*ck yes!”

Creating Focus Made a Dream Job Obvious

In retrospect, I had the power to create a dream job all along – and I suspect many of you do as well.

It wasn’t some brilliant idea or glamorous profession that did it. It was being very honest with myself about what was important, and being willing to eliminate any paths that didn’t facilitate that goal.

Once you’re doing what you’ve always wanted to do, the anxiety of financial payout or achieving short term targets changes dramatically. I don’t think any force of nature could curb my manic energy, but now I’m channeling it toward meaningful personal fulfillment.

I get to spend every day of my life now with Founders who are doing amazing things. We get to talk about the world together, and I get to do my part in helping them achieve their goals. I get to build a platform every day that will help make the lives of millions of Founders just a little bit easier for generations to come. Nothing compares to the satisfaction this brings.

I got here through alignment – that’s it. But now that I’m here, I’d like to do everything I can to help as many of my fellow Founders find their own path. I hope this helps you find yours.