Why Chris Guillebeau Believes A Startup is Less Risky than a Corporate Job + His Best Alternative

Why Chris Guillebeau Believes A Startup is Less Risky than a Corporate Job + His Best Alternative

chris guillebeau 100 startup

“Your possibilities are unlimited, but it all begins with the deliberate choice to think differently.”

— Chris Guillebeau

Can a Startup be Less Risky than a Normal Job?

I spent some time with Chris Guillebeau last week hearing some pretty interesting ideas – his answer to the above question was one of them.

He was on tour for his new book, The $100 Startup, which recently hit #3 on the WSJ and #6 on the New York Times bestseller lists.

His message is powerful and he does a damn good job turning some conventional wisdom on its head (where most of it belongs :)).

Chris has done more positive work for the area of creative careers and living life on your terms, than possibly anyone else out there – through his Art of Non Conformity site, The World Domination Summit, Travel Hacking Cartel and The $100 Startup, aside from all kinds of charity work and mentorship.

I have no idea how he does it all.

On top of that he’s just a really good person who genuinely wants to help. It’s an honor to consider him a friend and have his thoughts to share with all of you.

By the way, I have another post planned for later this week on How World Travel Creates Entrepreneurs (in prep for a big trip to Turkey I have coming up), but for now I think you’ll enjoy hearing some of Chris’s ideas. And since he is on a quest to visit every country in the world by age 35, I figure it’s pretty good timing (he has about 10 countries left).


Chris Guillebeau on The $100 Startup, Understanding Risk and Creative Self-Employment:

Scott: What is your vision for this book and the $100 Startup Movement? How specifically do you hope this helps people?

Chris: My hope is that the book will inspire readers to take measurable action toward greater freedom, whether an all-new business, a side income, or improving an existing business. Before the book came out there were already a lot of general, motivational resources, which are fine and can probably help people get fired up—but The $100 Startup isn’t one of them.

Instead, I wanted to create a plan that was highly actionable, something that readers could follow to start a “very small business” for the first time, or improve an existing business. The book will be a success if people read it and then take action, not just read it and say “Oh, that was interesting.”

Scott: I’ve heard you talk about entrepreneurship being conservative and less risky than traditional employment. This sounds crazy to most people. Can you explain how you see starting a business as a safer option than working for a big company?

Chris: Entrepreneurship has traditionally been viewed as risky because it involves investment and uncertainty. But these days, you can start a business in a short amount of time, using the skills you already have and without spending a lot of money. Even if success takes a few iterations to achieve, there is very little downside.

Contrast this reality with the reality of today’s job market. Real unemployment among young people, even college graduates, is often 15% or more. Many people are underemployed by working at Starbucks or taking other low-level jobs because they can’t find work in the field for which they trained. Layoffs are rampant, and most “real jobs” allow for little flexibility or real advancement.

Which is the safer choice?

Scott: Who is this not for? What type of people are not fit to be starting and running a micro-business?

Chris: Well, I don’t know if it’s a matter of fit. We talked with 1,500 people from all over the world (all ages, backgrounds, etc.) for the study. All of them had found similar success through different approaches.

However, I think it’s also fair to say that there are some people who are genuinely happy in their jobs and don’t have any desire to go it alone. If you feel like your position is secure and you love what you do everyday… no need to read The $100 Startup.

Scott: You interviewed and interacted with over a thousand entrepreneurs in the past couple years. The case studies cover the gamut. What was the most inspiring story (or at least one of the top five)?

Chris: I’m a bit of a renegade, so I’m personally drawn to stories of other renegades who were determined to go it alone no matter what. I like the story of Megan Hunt, who was just twenty-years-old when she stepped out to work on her own as a clothing and wedding accessories designer. Four years later, she now owns the co-working space she works from, and takes her young daughter to work every day.

However, most of the people I talked with for the study weren’t like Megan. Most were a bit older and had been established in some kind of traditional career. Then something happened—several had lost their jobs or otherwise had a big, scary transition moment. The scary moment turned into an inspiring story as they ended up starting a business instead of returning to the traditional workplace.

Scott: You talk a lot about web and information businesses, such as blogs, as being low cost startup options. But there are so many new blogs and sites every day. At what point is that space too crowded?

Chris: It’s funny — you were at the San Francisco $100 Startup gig, which was indeed a great night with a strong turnout. But I noticed when we did the QAA (Questions and Attempted Answers) that almost everyone asked questions about blogging and information businesses. In most places, like Santa Cruz the next night or L.A. the night after, almost no one asks about those things. I do think there are many more opportunities than the “professional blogger” model that some of us follow.

To answer your question directly, though, I don’t think it’s a matter of the space becoming too crowded. The fact that multiple people are pursuing projects in similar fields is usually a positive sign instead of a negative one. The market of people desiring to improve their lives is essentially unlimited.

Scott: As entrepreneurs I think we often underestimate how intimidating the first few steps can be. What’s your best advice for getting started with your $100 startup project? Especially for people still working jobs they don’t enjoy, with family obligations and a full schedule.

Chris: One thing I’ve learned is that most “business ideas” we have are actually too general. So the one thing your smart readers can do is convert their general ideas into specific offers. What will you actually offer the world, and how will you get paid for it?

Starting a business isn’t that complicated. You don’t need an MBA or a 60-page business plan that no one will ever read. You do, however, need a few things:

a) A product or service

b) A group of people willing to buy it

c) A means of getting paid

When thinking about business ideas, always think in this framework: what it is, who it’s for, and how you’ll get paid.

Bonus points: for those working day jobs, you have an added benefit. Instead of having the luxury of extra time to mess around, you have to make your limited business-building hours count. It will greatly help you to focus primarily on the income side of your business, understanding which tasks you choose to complete will get you closer to increasing income as opposed to simply keeping the wheels turning.

Scott: If you were starting The Art of Non Conformity and your business today, what’s one thing you’d do differently given what you’ve experienced in the past few years?

Chris: The main thing isn’t so much doing anything differently, but rather wishing I had started earlier. I love what I do and find myself very fortunate that I can make a living through travel and connecting with people.

On a practical level, I probably shouldn’t have branded my main website as ChrisGuillebeau.com. For some reason, people have difficulty spelling my name! But fortunately, many of them do find it eventually.

[end interview]


Thinking Differently…

I’ve spent a fair amount of time with Chris’s book since it came out (and given a lot of copies as gifts) and I genuinely feel it’s one of the more foundation pillar pieces of content of the last few years, if not more. It will no doubt help a lot of people and it’s a very powerful compliment to the work we’re doing here at Live Your Legend.

You can grab a copy or learn more about Chris’s $100 Startup book, which recently became a NY Times Bestseller, over at 100startup.com. His book trailer is damn inspiring too. Oh and in case you’re wondering, I don’t get paid for promoting this, I just believe it will be a lot of help to our community here.

Doing work you love can be a lot less risky than you think. 

There’s only one way to find out.

It starts with thinking differently.

We’re here to help.


P.S. Keep an eye out later this week for a fun post on how world travel made me an entrepreneur. Been wanting to share it for a while!