Entrepreneur and world traveler Chris Guillebeau shows how to start your own business for $100 or less.

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I’m really starting to believe that there truly has never been a better time to start your own business.

Here’s why:
- The bad economy actually helps … you no longer have a blanket of security with your job
- There is a career revolution going on … more people working freelance, more freedom in the workplace, the ability to work remotely
- Tons of support for startups … meetup groups, funding, kickstarter, skillshare, etc
- Everything you need to get started online is either free or cheap … web hosting, email, blogging platforms, photo and video editing programs, etc.

So why haven’t you started your own business?
Or at least a side passion project?
Are you still skeptical?
Maybe you think that’s for OTHER people?

Great question.

You might be able to find the answer in a new book called the $100 Startup by Chris Guillebeau.

In researching the book, he interviewed 1,500 people that fell under the following qualifications for their business, of which about 50 made the final cut for the book.

- Cost $100 or less to start
- Generating at least $50,000 in revenue per year (which happens to be about the average HHI in the US)
- Willing to provide full disclosure of that income
- The business couldn’t require highly specialized skills
- Less than 5 employees
- Drawn from case studies worldwide

Why I love the IDEA (as well as the content) of this book.

First off, I love the concept of this as a book idea. Is there a widely-held belief that it is difficult to start an online business? BAM. Do some research, find a whole bunch of people that HAVE done it, interview them, and then present the case studies along with other valuable information about how they’ve done it.

There, I just gave you your next book idea. Are you passionate about cupcakes? Does everyone you know feel that it’s a passing phase and think you can’t have a successful cupcake business? Go interview the top 50 cupcakes stores in the US and dispel those myths and reveal the key to success.

Same thing for taking good photos, losing weight, learning to speak a foreign language, overcoming asthma, or creating an app for the iPad. Find a bunch of people that have done what you want to do, and figure out how they did it.

Here’s what we’re going to do today. I got to meet Chris in person but he was incredibly busy in the middle of his book tour, so he was nice enough to do an interview over email. I have a few topics around the book I’d like to discuss first. You can see the outline below, or play the podcast to get the full content. Then, we’ll get to his questions.

Thoughts around Chris’ marketing style and books

1. The phenomenon of getting on someone’s radar
a. How did I become aware of Chris?
b. What is the World Domination Summit, and who is speaking there?
c. What is The Art of Nonconformity?
d. My meeting with Chris at SXSW
e. How I became aware of the $100 Startup

2. The power of connecting with an individual
a. What Chris did at the book signing that surprised me
b. How a busy author responds to email
c. The importance of taking time to answer reader questions

3. What all that means
a. Taking a long view of marketing your business
b. Every interaction counts; people remember the small things
c. Build out many touch points
d. Build a strong network

4. The Art of Non-Conformity
a. Set your own rules, live the life you want, and change the world
b. Is there a better alternative to grad school?
– Option 1: $32,000, 40 hour thesis, 3 readers, slight expert recognition, “Good job” from 3 people, diploma
– Option 2: $9/month for hosting, 40 hour manifesto, 100,000 readers, broad expert, thousands of comments, speaking/boo
c. Chris’ amazing goal for World Travel

5. The $100 Startup – take aways
a. The Mattress story
b. Should you really “teach a man to fish?”
c. The “frequent flyer mile guy” story

Jim Interviews Chris Guillebeau about the $100 Startup

Jim Hopkinson: Describe yourself in 3 words

Chris Guillebeau: Persistent, flexible, caffeinated.

JH: “I want to travel more” is at the top of almost everyone’s bucket list, yet the average American spends more time in the bathroom than on vacation. You’re nearly complete with your goal of visiting every country in the world. What’s something the average person can do to break their paralysis and get started?

CG: Just go somewhere. Seriously. It’s easy to let aspirations get out of control to the point of paralysis. Most everyone can conjure up a fantasy vacation, like hiking Kilamanjaro or ten days in the Seychelles, and so they delay travel until the day they’ll take that trip (for which they’re really not planning, anyway).

Meanwhile, taking a quick trip to Canada or Mexico is much more likely to get the ball rolling for prioritizing travel than planning a once-in-a-lifetime getaway that you might never end up taking.

JH: Like you, I’ve seen a very strong trend in people pursuing their passion and discovering a career lifestyle. Do you feel this is truly a new thing, and if so, what has been the main driver of this?

CG:I think that this career “lifestyle” might just be a new iteration of a trade in the way that one’s craft or work used to be an expression of person’s lifestyle and skills. We’ve only been on the assembly line for a century or so—and I think most everyone is sick of it.

Technology, the economy, and of course the personality of the Millennial generation have all converged at just the right time to allow people to begin to do exactly what they’ve been wanting to do for decades. For many of us, that means getting out of the factory and getting back into the world.

JH: Marny from NY Creative Interns was at my Reboot Workshop Conference and donated your new book to us to give away as a prize. When I asked her about it, she said she had an extra because they asked you to donate 20 books, but they were thrilled when 120 showed up. Classic case of under promise, over deliver?

CG:Well, they should have actually received 200. So if they received less, that’s more like underdelivery—which hopefully wasn’t the case!

JH: I’ve been promoting the advantages of launching an online business for years, but people always have their doubts. In your new book, The $100 Startup, you interviewed 1,500 entrepreneurs, each making more than $50,000 a year based on businesses that cost less than $100 to create. Was there a common thread among the people you spoke with?

CG:The case studies were diverse and came from many different backgrounds. What they had in common was an ability to create something useful to the world, not just something that they were personally excited by. In addition, I think it’s fair to say that most of the unexpected entrepreneurs were fairly curious (they wanted to know everything about their topic of interest) and also somewhat persistent (if the first idea didn’t work, they shifted to something else).

JH: Once someone has created an online business, in your experience what has been the best way to market your product and get the word out and drive revenue?

CG:People often underestimate just how much momentum it can take to get attention. It’s important to understand, though, that relentlessness isn’t some major commitment you make to incessantly bug the heck out of people; it’s really more a determination to systematically build relationships and alliances that ultimately work together to create a movement that’s bigger than yourself.

I always recommend you start with people you know. When you think about it, you probably know lots of people. How can they help? Is there a way you can invite them to participate? Then once you have one customer, treat that customer like the most important person in the world. Chances are, they’ll lead you to others—if you do your job right and improve their life.

JH: What’s the most valuable piece of advice you can give to people looking to start their own company?

CG:Think long and hard about what you can make, offer, or provide that other people will value enough to pay for. All successful businesses, no matter how large or small, come from this model. And here’s a bonus: Don’t wait. Every day you wait puts you a day further away from freedom.

JH: I am attending your World Domination Summit in July. What should I expect?

CG: You should expect to have a good time, meet fun people, and be challenged. WDS is centered on the question of “How do we live a remarkable life in a conventional world?” Everyone answers that question in their own way, and everyone participates in helping others.

Hopkinson Report Disclosure: I received a free, pre-release copy of the $100 Startup when I saw Chris speak at SXSW, but otherwise was not compensated for this interview in any way. Amazon.com affiliate links used where available.

Today: The importance of owning your own domain name, and suggestions for alternative website names.

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What happens when someone Googles you?

Seems like an innocent question, right? But go ahead and ask 10 random friends and see what they say.

- Some are confident and know that the top results are their own website, or a LinkedIn page or Facebook.
- Others have a popular name, and thus can’t quite make it to the frontpage.
- Some have positive results come up, such as a listing at a conference or something with the college alumni, but nothing special.
- For the unlucky, an unflattering photo or comment appears near the top of the list.
- And for some segment of people nothing comes up, and they don’t care.

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You’ve quit your job and are ready to start a new business.

What are 10 things you can do to make smart decisions without breaking the bank?

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If you’re reading this blog, there’s a good chance you’re thinking about quitting your job, you just made the conscious decision to do so, or the choice got made for you and you were laid off.

No matter what your situation, you may be thinking, what the heck do I do now?

The idea of starting your own business or transitioning to a freelance lifestyle can be overwhelming, so today I’m going to tell you where to start. Here are my suggestions for:

The first 10 things you should do when starting your own business

1. Define and control the message

The first thing you need to do is decide what happened and what your basic plan is moving forward. If you were laid off or fired, definitely check out The Hopkinson Report Episode 180, You’ve been laid off: What to do in the first 60 minutes.

It’s very important to be able to speak to your situation clearly. In some cases, it’s easy, not to mention fun. Your message might be, “After 21 years in the corporate rat race as a lawyer, I’ve decided to leave my role as an attorney and focus on my passion for helping others, by starting a non-profit that helps inner city parents get legal help that they need.”

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Haters gonna hate! How to handle negative feedback on the internet.

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“Hey Jim, I wanted to let you know your first post was live. Thanks again and I can’t wait to read more.”

The email came from my new editor Aaron over at Salary.com, where I’d signed on to write a few columns per month. I was excited to see my first post, which was titled “Foul Ball: How One Interview Question Can Lose You the Job.”

It was a fun little article that really dug into a single aspect of my intern hiring process when I was at Wired. In a nutshell, after listing quite a few qualifications that I was looking for in a candidate, from marketing savvy to technical know-how, just for fun, at the end of the ad I listed a bonus question: What is my favorite baseball team?

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Jim talks with short-term peer-to-peer rental company Roomorama to find out how you can host or rent an apartment anywhere in the world.

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It’s been recently called “The Third Office.” The lines have blurred, as people “work” from their office, their home, and more and more frequently, from a third office, which could be a local coffee shop, an airport lounge, downtown Singapore, or anywhere you can get a mobile signal. Sometimes it’s a coffee shop IN Singapore, minutes after landing in an airport.

One of the companies leading this new “Gig Economy” is Roomorama, a peer-to-peer short term rental marketplace. The concept is simple… anyone can rent out their apartment while they are away and collect income, and they can just as easily stay in one of Roomorama’s 36,000 cities worldwide. The benefit? Usually much less cost than a hotel, while keeping a local flair.

Since I “buried the lead” a bit in the interview, I want to congratulate Roomorama on their breaking news:

Roomorama And Lofty.com Merge Online Rental Sites, Take $2.1M Seed Round (via Techcrunch)

This is great news for the team, including my friends and co-founders Jia En Teo and Federico Folcia, who I interviewed way back in Episode 26 in October 2008.

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Losing your job can be a traumatic experience. What you do in the first 60 minutes can have a huge effect on how you handle it.

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It’s the relationship equivalent of “We need to talk.”

You stroll into the office on a Friday morning that seems like every other, upgrading to a large coffee to push away the headache from last night’s extra glass of wine at dinner. You comment on some reality show drama to your co-workers, then head for your desk to start the day.

However, your boss catches you just as you’re about to sit down, surprising you with the innocuous request:

“Can you step into my office for a moment? I need to chat with you about something.”

Ten minutes later your world is crashing around you. You know that your supervisor specifically explained the situation – it was as if they were reading off a script – but your brain couldn’t process all the buzzwords like “hierarchy restructuring” and “corporate reorganization” and “economic budget constraints” because your mind was racing trying to process the one truth that was abundantly clear:

You’ve lost your job. What you do in the first 60 minutes is crucial.

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Photo above: The sold-out crowd at the premier Reboot Workshop Conference.

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Jim sits down with business partner Nate Cooper to talk about how they created, planned, and got sponsorship for a successful conference in less than 60 days.

Below are the highlights from our conversation. Listen to the audio to get the entire lowdown.

In this podcast we answer the question:
What the heck were Jim and Nate thinking planning a huge conference with no experience?

We break down the steps as follows:

1. Choose the right business partner
Hear the back story of how Jim and Nate connected. Working with the right business partner can make all the difference in the world. We were connected through two different mutual friends, and found ourselves in a position to help each other out.

- Nate wanted to learn more about book publishing.
- I wanted to pick his brain about entrepreneurship.
- We both wanted to quickly get to work on something awesome that would help people and maybe make a little money.

While Nate had a background running events at Apple, and I’ve run large events at SXSW and well, everything from fraternity parties to impromptu roofdeck concerts in Manhattan, we just knew that we could pull it off.

Most business partners are like the odd couple: The sales guy and the tech geek. The CEO and CTO. The person that is good with numbers and the person that is good with people. However, I’d say that Nate and I share far more similarities than differences. While he brings a laid-back Brooklyn vibe and more technical street-cred and my more corporate background matches my Manhattan address, we both are geeks at heart, love to teach, and both brought a very large network of friends and business connections.

2. Come up with a good name
We talk about how we came up with the name Reboot. Like true geeks, we didn’t start with a concept, or something quirky… we started on the web. What is a name that we could come up with that represented the conference, but was also an available URL.

We went through a brainstorming session, throwing out words like bootcamp, career, kickstart, jumpstart, and so on. In the end we had our winner because we were able to secure RebootWorkshop.com (for our 1 day event), RebootWeekend.com (if we want to expand to two days), and RebootNation.com (for when we take over the country).

3. Decide on the format
I think the thing that really made the conference work was our unique format, which was culled together from various sources.
a. The main structure was based partially on the Startup Bus Accelerate “unconference,” which Nate had attended recently.
b. We wanted the day loosely structured, so that we could change things on the fly and adapt to what was working
c. We needed to introduce our 10 speakers and give an overview, but wanted to avoid death by Powerpoint. I suggested the twist of “Ignite-style” presentations, which forced presenters to get their message across in 5 minutes flat. Every speaker had 20 slides, which auto-advanced after 15 seconds. It was a little nerve-wracking to present, it was fun, and it worked.
d. Allow time to network. This was built in during lunch, in between sessions, and afterward.

4) Secure speakers through our personal network
Nate and I talk about how getting amazing speakers was actually the EASIEST thing for us. Both of us brought a strong network to the table and we quickly listed out a group of 15-20 people that might be interested. From there, we narrowed down dates, availability, and relevance to the topic. The list of speakers is available on the Reboot Workshop website.

5. Sponsorship
We knew that we had a valuable audience, but would a sponsor step up to the plate for a brand new conference? We were going to find out.
Here are the steps we took:
a. Create a media kit talking about the audience and the speakers
b. Reach out to your network
c. Divide sponsorships into levels
d. Be willing to exchange sponsorship status in exchange for promotion

Saul Colt stepped up right away and said that Freshbooks would be a premier sponsor of the conference. Now, was this “cheating” since Freshbooks was already a sponsor of this podcast? I say no. We still had to have relationships in place, we needed to bring a targeted audience, and we needed to pull off a 6 hour event without a hitch.

We also named THIRTEEN contributing sponsors that helped us out in many different ways, from promoting the event to their audience, to donating supplies and prizes.

6. Location
When it comes to location, let me tell you it is NOT inexpensive to rent out a large space in New York City. Thus, once again we worked connections, decided on a space and lined it up early. We went with the New Work City co-working space, which is where Nate was working from as a freelancer. Tony and Peter were amazing and gave us access to set up the night before, and the huge loft was great for our purposes. Plus, the key was that everything we were talking about in the conference — leaving your job to go out on your own — gelled with what New Work City did, which is support independent workers.

7. Create a web presence
With any modern business, you need a web presence. Nate and I talk about how we did so quickly in three steps:
a. Built on a low-cost premium WordPress theme
b. Hired a designer for a professional logo treatment
c. Build the site based on best practices from other conferences

8. Collecting money
OK, now that you have a product, how do you collect the money? Once again, we didn’t want to reinvent the wheel. We wanted to use an established site such for commerce that would easily integrate into WordPress, so we chose Eventbrite.com. One of the main advantages, was their ability to give custom, trackable discounts.

9. How do you market your conference?
What did we learn from marketing the conference? How do you get the word out? We touch on several topics:
a. Using each speaker’s extended network
b. Networking at meetup groups based on the conference topic
c. No magic bullet, you might have to go to an event of 200 people to make 2-3 key connections that will attend and tell friends
d. Hire a photographer and video person for future marketing
e. Partnering with key groups around the city and offering unique deals to spread the word

10. Pricing
One somewhat controversial decision was pricing. We made it just $40 (including lunch) so that it would be accessible to all and make it a complete no-brainer to attend. Our goal as unknown entity for our first round was to keep a low barrier to entry and then blow people away with value. Still, others urged us to make the event free -or- charge upwards of $200 or more. Download the podcast to find out the one key move we made halfway through that encouraged earlier signups.

11. What didn’t go right?
Of course, we’d be lying if we said everything was PERFECT. In fact, I don’t think we even mentioned that I got violent food poisoning the night before, to the point where I lost my voice, barely made it through my speech, and at one point lost hearing in my right ear! We explain the one thing we’re definitely going to outsource for the next round.

12. The future of Reboot
With the success of our first conference, we’re excited to not only do more, but to make this a real business entity. We’re focusing on three things:
a. Reboot Newsletter sponsored by Emma email, to let people know about future events and speakers that support the Reboot brand (sign up here)
b. Reboot Happy Hours used for pure networking and fun, held regularly to build the brand and promote the conference. Find Reboot Happy Hours on Meetup.com
c. Quarterly Reboot Conferences, maybe even a summer getaway conference

Get more info at RebootWorkshop.com
Want to become a sponsor? Email nate [at] rebootnation.com

Jim kicks off the newly branded Hopkinson Report Blog and Podcast, highlighting three powerful workplace trends

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WOW.

I am SO excited to be back doing The Hopkinson Report podcast.

JUST WOW.

Where to begin?

I think a good way to do this would be to look at the past, present, and future.

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Over the weekend of November 11th, I experienced what seemed like a once-in-a-lifetime trip. I was fortunate to be chosen as one of several “new media influencers” to try out a new service called “Lux Delux.”

But in reality, treating yourself to an amazing experience filled with top of the line customer service doesn’t have to be once-in-a-lifetime; Lux Delux aims to be the chosen service for anyone that wants this experience throughout the year.

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Discover the three best ways to engage with readers on Facebook

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Facebook continues to be the social media giant. It’s funny to look back at Episode 105 eighteen months ago back in May 2010 when I wondered whether recent privacy events could signal the fall of Facebook, and I went through 7 reasons the mighty giant might fail.

Needless to say, they’ve recovered from some of the issues I posed, including privacy concerns and revenue generation. In fact, the New York Times and Wired ran a stories about a group of students that were taking on Facebook with a new product called Diaspora, and it gained some pretty good buzz.

Where are we 18 months later? Well, Diaspora seems to be in alpha release still and in retrospect, was just a tiny fly on the back of a Rhino. And that Rhino would be Google Plus, which Facebook seems to be going head-to-head with and still winning.

Of course by now if you’re a brand, you have already have a robust Facebook page. You’ve updated some graphics, built up your following, and have widgets on your website to drive people to Like you on Facebook.

But now that you have fans on Facebook, how do you engage with your audience?

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