Starting a Business is the New “New Job”

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My career started out very exciting. I got fired from my first job out of school. Twice. Which, while I was sure that meant the end of my professional career (I was 11 months out of college) resulted in the happy accident of finding myself at a string of startups. I didn’t know it at the time, but this was the dot com era and it was a REALLY exciting time to be a software developer. Life was good.

15 years later I found myself sitting on the floor at a conference. Surrounded by discarded magic markers from a workshop that had ended hours ago with a giant piece of paper in front of me on which I’d charted out the joys and highlights of my career.

Career Happiness Chart


Something had gone very wrong

This wasn’t working. My career felt broken. The more experienced I got, the more miserable my jobs became. I wanted to quit corporate life and just work for myself. Teach on the side. Move someplace quiet and relaxing.

I don’t know what I expected, but it certainly wasn’t to end up teaching workshops at MIT and Harvard on how to start your own business. Or to be working for myself while living on 8 beautiful acres in a peaceful little town 90 minutes north of Boston.

But here I am. Still figuring things out, to be sure. But doing it on my terms.

I think sometimes we just have to take control and recognize that somethings gotta change…

Starting a Business is the New “New Job”

I believe that no matter how great our careers are, we all reach a point where we outgrow our current job options. Where we’ve accumulated more talents and interests then our employer could possibly accommodate and where it’s difficult to find any jobs that would be able to.

And so the purpose of this series is to help you start your own business. As a side project or a full time gig.  To give you options beyond what others ever could. And… I hope, to let you hit new levels of joy in the chart of your own career.

Each article will cover a new topic in helping you start your own business – be it part time solopreneur working from home in your pajamas or the next Facebook. I’ll share what I’ve learned from helping hundreds of entrepreneurs before you, as well as my own still-in-progress journey.

Let’s start with the #1 question on anyone’s mind who ever wanted to start their own business…

Tip #1: The Punk Rock Secret to Getting Customers

Imagine that you have an idea for a travel app that’s going to make you rich.

If you go into the app store and search on travel, you’ll get over 90,000 apps. Some of those apps have been around for years. They’ve been updated and enhanced through version after version. Accumulated hundreds of customer reviews, thousands of downloads.

How will you get your app noticed? A handful of reviews from friends, a few dozen downloads. Not a whole lot of features because you want to get it out quickly so you can start bringing in the big bucks…

OH. And you want to charge MONEY for it?

With so many free travel apps out there?

You have fewer features, fewer customer reviews, nobody has ever heard of you before or seen anyone else using your app. AND you want people to pay for it?

Hah! Good luck even getting them to download a free trial.

How are you going to stand out?

I don’t care if you’re building the next Facebook or selling your services as a freelancer, there is one proven way to stand out. And that is to do what goes against everything that you want to do.

Start small

When you try to build a product or service that appeals to “everyone” (my travel app is so universal, it can help everyone who wants to travel!) it’s kind of like being one of those people who wants everyone to like them.

BORING. Uninteresting. Forgettable.

Instead, imagine that kid in high school with the spiked hair, black eyeliner, and combat boots. You know, the one you can still remember even as your 20th reunion rolls around.

Punk Rocker

THAT is who you want be.

In other words: forget doing a travel app for everyone. Instead, make a travel app for the smallest group of people possible.

How about only people who want to travel for their honeymoon?

Good start, but that’s still a LOT of people. How can you make it more specific?

People who want to honeymoon in Hawaii.

Maybe. Although, as one of the top honeymoon destinations, that’s not terribly punk rock.

Keep digging until you hit interesting

What about adventure travel honeymoons? Extreme sports? You know, when you strap on your skis, get into a helicopter and have it drop you at the top of an untouched snow covered mountain? Or cave diving. Or volcano surfing, where you slide down active volcanoes! (apparently this is a thing. Internet, I love you.)


Okay, THAT is interesting. An app for extreme sport honeymoons. I hope one of you reading this builds it because I totally want to check it out.

Now, 99% of the people searching for travel apps won’t give a damn about your app. But for those newlywed adrenaline junkies – which is going to be more interesting to them? A generic travel app to help them plan their trip? Or an extreme sport/adventure honeymoon app where they can pick the most romantic erupting volcano?

Your customers will Love it

Oh my god, if you can give them a single place to find and book honeymoon themed extreme sports, just imagine how fast word is going to spread to their heliski buddies.

It will so much easier to market. So much easier to create a delightful experience because you know exactly what people will be using it for (imagine an instagram type feed of volcano surfing videos in place of the typical text based list of airfares). And it’s so much easier to reach your customers because you know exactly where to find them – sporting goods stores and ski shops and adventure websites and helicopter rentals.

Not at all Exactly like Facebook

But there’s only SO many couples who want to go on an extreme sport honeymoon. This feels SO limiting. You could never do anything big like become the next Facebook with this strategy.

Oh. That’s right.

Because Mark Zuckerburg started with the ginormous potential market of…. Harvard students.

Starting small is not the same as staying small

Just because you start small does NOT mean that you have to stay small.

Once you get traction with those first customers, it will be SO much easier to expand what you do to provide offerings for more customers. Or maybe to provide more offerings for your existing customers (his and her volcano sleds!).

Would everyone have jumped on Facebook if it was initially available to everyone in the world? No way! When was the last time you downloaded a social media app that you never heard of, that no one you knew was even using? Facebook gained traction because – by going after such a small group of people, they were able to build something those students specifically wanted and to a small enough audience that word spread quickly.

By the time they’d dominated the Harvard student base, word had started getting out to other universities. They were able to slowly open it up to select universities, and then all students, and then everyone in the world. And now weirdly your mother is hanging out in the same place that your friends are. There’s no way in the world they could have STARTED there and been successful. Nobody wants to go hang out with their mom, their crazy uncle, that cousin they never talk to, and all their best friends in the same place.

And yet. Here we are.

But, I’m not into anything as punk rock as extreme sports

Exactly! That’s the whole point — to only appeal to a very small number of people.

The goal is not to try to find the most hard core thing. It’s too find something so incredibly specific that you can make it really interesting.

Make your app about honeymoons for senior citizens. Or honeymoons you can bring your dog on. Honeymoons for people who don’t want to leave their homes. Or honeymoons for knitters.

It doesn’t have to be sexy. It just has to be specific.

Rock n Roll Knitting Grandma


What’s YOUR idea? Share it in the comments below if you’d like feedback!