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.

As I’ve talked about many times, it’s easy for someone like me, living in New York City and completely immersed in all things media, to have a distorted view on a topic like this. Not only do I have a blog and a podcast and a book, but I actively own websites and purposely try to make sure my results rank high.

Just the fact that you are listening to my podcast or reading a blog like The Hopkinson Report, means that you probably have a certain degree of knowledge about your results, and are probably proactive in controlling it.

And yes, there are plenty of people that don’t know and don’t care.

However, there are maybe millions more that WANT to have a presence on the web, but don’t know how to get started. If that’s you, I’m going to show you how at the end of this post. But first off, here are…

4 reasons WHY you should own your own domain

(Listen to the podcast to hear me dig deeper on each of these topics)

1) Rank higher in search
If you’re establishing a personal brand or starting a business, you’re going to want to own your own domain. While major sites like LinkedIn and Facebook will bubble to the top for newly established people on the web, Google’s algorithm weighs exact searches heavily. So if your name is John Doe and someone types John Doe and you own JohnDoe.com and it is a legitimate site with good content on it, eventually that will bubble up to the top.

Ironically, I am a bad example of this. If you Google Jim Hopkinson, in most cases The Hopkinson Report.com shows up before JimHopkinson.com. The reason for this is that this site was established in 2008, and has hundreds of links back and forth to major sites like Wired, and tons of content. Meanwhile, I launched JimHopkinson.com within the last six months. But if you’re starting from scratch it might work differently for you.

2) Hide negative search results
It’s not always easy to remove that drunk photo from college that comes up in a search, but by registering your own name, you can make efforts to try and make sure that your domain comes up ahead of it.

3) It’s crucial for job seekers
Every job seeker should have their own domain. According to the NY Times article Social Media History Becomes a New Job Hurdle, “75 percent of recruiters are required by their companies to do online research of candidates, and 70 percent of recruiters in the United States report that they have rejected candidates because of information online.”

4) Reserve your name or children’s name for later use
Even if you don’t have plans for yourself or a business now, you might want to reserve your name so no one else gets it. Also, many parents are registering their children’s names, whether to put up some baby photos and videos, or just have it set aside if they become the next Bill Gates or Steve Jobs.

But what if your name is already taken?

IE, Your name is John Smith and JohnSmith.com was snagged long ago. Never fear. Here are…

7 suggestions for alternate website names:

(Listen to the podcast to hear me dig deeper on each of these topics)

1. Use another domain extension
Option: Register JohnDoe.net, JohnDoe.co, JohnDoe.org, etc.
Pros: Address remains short and easy to read.
Cons: You may need to constantly remind people that it is not the most common .com address. Be aware of what actually does live at the .com address, as at least some people will go there accidentally.

2. Add a middle name or initial
Option: Register JohnTDoe.com or JohnThomasDoe.com.
Pros: It uses the common .com extension and works if people are familiar with your middle name.
Cons: It’s a little more unwieldy and harder to remember.

3. Add a clever modifier to the name
Option: Register TheJohnDoe.com, YouveGotJohn.com, OriginalJohnDoe.com, TheRealJohnDoe.
Pros: Very “Twitter Celebrity-esque and works for some people.
Cons: Harder to remember, feels forced, and tells everyone you couldn’t get the domain you wanted.

4. Add an internet based word to it
Option: Register JohnDoeOnline.com, JohnDoeWebsite.com, etc.
Pros: Pretty straightforward and keeps your name as you want it.
Cons: Harder to remember.

5. Create a new word or company name
Option: Register DesignFroggle.com, DesignForSocialChange.com, etc.
Pros: Using a fun or generic word worked for Amazon, Google, and Yahoo. Just as easy to promote your company as yourself.
Cons: Harder to find unique names vs. back in the 90s. You still won’t own your name.

6. Tie your name to your location
Option: Register JohnDoeNYC.com, JohnDoeInSeattle.com, etc.
Pros: Ties your name and brand to a specific part of the country.
Cons: You can never move.

7. Tie your name to your profession
Option: Register JohnDoeDesign.com, ArchitectJohn.com, etc.
Pros: Ties your name and brand to your specific industry.
Cons: You can never change jobs.

3 things NOT to do

1. Use dashes
Option: Register John-Doe.com
Pros: Straightforward.
Cons: It’s one thing to see this written, it’s another to say it. Every time you tell someone your website, you’ll need to say “John Dash Doe.”

2. Use Numbers
Option: Register Website4JohnDoe99.com
Pros: Nothing.
Cons: Again with saying it out loud… you’ll need to say “The word website, the number four, john doe, the number ninety-nine.” You can do better than that.

3. Try and be really clever
Option: Register J0hnDoe or JohnDoh! or YouveGotSexyJohnny
Pros: You are clever for 1 minute.
Cons: People will be annoyed for a lifetime.

So how do you make that first step?

It’s easy to think about hiring a designer or installing WordPress or planning a huge web presence. But if you’re just getting started, you just want a simple landing page, or you just want something for companies to find while you are job seeking, here is my suggestion:

1. Buy your domain GoDaddy.com
2. Set up a free about me landing page
3. Redirect the url (yourname.com) to the landing page.

That way you look a little more professional and can put jimhopkinson.com on your resume and business cards and not about.me/jimhopkinson

This is incredibly simple, takes less than 10 minutes, and can be up and running in an hour, so I tell people.
Get Your Name Today!

And to make this simple, I created a website called, you guessed it,

www.GetYourNameToday.com

Two quick caveats
1. As of this post post on May 9, 2012 I’m still putting the final touches on the site and on the video tutorial, so depending on when you read this, it still might be a bit of a work in progress. But it’s about 95% done and functional, so check it out and let me know what you think. You can click the contact link on the header and send me an email, or hit me up on Twitter: @HopkinsonReport

2. I want to give full disclosure that I am a member of GoDaddy’s affiliate program, which means I earn a small commission if you sign up by clicking the link on the site. This does not in any way affect or increase the cost of your domain — think of it as a small ‘thank you’ if you found the information I presented here valuable and time-saving for you.

So don’t wait another minute to grab your domain because someone might snag it from you… Get Your Name Today.

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.”

If you were laid off, your message might be “My company recently restructured and my job as creative director was eliminated, so I am taking this opportunity to launch my career as a freelance designer helping photographers build websites to showcase their work.”

Additional things to add might be how people can help you out as you get started, which could include client referrals or testimonials for your website.

2. Relax and regroup

While the reaction for many is to immediately jump into action and attack this new stage of life, I think it is beneficial to take a break and regroup for a bit. I’ve heard from many people that took several weeks off after a layoff, just because they hadn’t had a real vacation in years while at their previous job.

Never got to take that 3-week safari in Africa that you’ve been planning for a lifetime? Take an honest look at your life. If you don’t take it now, will you ever find the time to go?

However, this time for self-reflection doesn’t mean you need to spend your entire severance check on a bungalow in Tahiti with an infinity pool halfway around the world. Maybe it’s just a few weeks around the house doing those projects you never got around to because you were too tired. Or maybe it’s a week camping with the family at a National Park and going on a nature hike to clear your mind. Take a little time for yourself.

3. Finalize Severance, Cobra, Benefits, Health Insurance

Take the time to make sure you fully understand any severance package your previous company has offered. If needed, have a lawyer go over any documents, and don’t be afraid to negotiate any items you feel should be included. Most likely, your employer wants a clean break and wants to avoid a disgruntled employee, so there’s a chance they’ll relinquish to make you happy.

Next, figure out your health insurance, as this can be one of your most costly expenses and a source of stress. The easiest method would be to change over to a spouse’s plan if that is an option. Otherwise, another alternative is to stay under your current plan via Cobra. Going on your own, consult resources like the Freelancer’s Union or speak with friends that own their own business to see what plan they recommend.

4. Assess money issues/unemployment

Once your health insurance situation is set, turn to the rest of your finances. If you are eligible for unemployment, sign up for that immediately and set up a reminder to claim your benefits on the same day every week. Speak with your financial planner if you have one, or sit down and do an honest assessment of where you are.

- What are your exact monthly expenses?
- What can you reasonably expect for income moving forward?
- How much savings do you have?

You might want to take immediate and sometimes drastic actions to cut costs. For example, cutting down on eating out, cancelling services like cable TV, excessive cell phone features, subscriptions such as Netflix, or any large planned purchases.

5. Get invested

However, it is important not to be penny wise and pound foolish. Even though your high speed internet access bill might be costly, you’ll need it to surf the web for jobs and network online.

This also might be a time to INVEST in yourself. For example, even though I had just lost my job, one of the first things I did was head to the Apple store and upgrade my aging 4-year-old iPhone to the newest model and plop down $1200 on a new Macbook Air.

Sound counter-intuitive? Perhaps. But I knew that as a freelancer, speaker, teacher, and consultant, I would be working around town and around the world with my laptop constantly at my side. Not only would the faster processor make me work more efficiently, but lugging my current 5 pound model wouldn’t be doing my back any favors. Lastly, because I’d be on my cell phone with clients on a consistent basis and not utilizing a landline at the office, I needed a phone and service I could trust without dropped calls or them yelling “You’re breaking up! I can’t hear you!”

There are a few more things you’ll want to invest in to present a professional brand. If it’s been awhile since you upgraded your closet, get yourself a few “go-to” outfits to evoke the image you wish to project. Once again, you don’t need to break the bank, so we’re not talking half a dozen Armani suits at $4000 a pop.

For me, it was an opportunity to go through the 7-8 suits and sportcoats I had in my closet. A few were in great shape and I brought them to the dry cleaners to be pressed. Several were outdated or never fit right, and I donated them to charity, making sure to take the write-off. Four of them were in great shape, but the sleeves were too long. For about 10%-20% of the cost of a new suit, I had them professionally tailored and the difference was amazing.

[Note: According to GQ's Style Guy, your cuffs should at least half-cover your watch, and a half inch of shirt cuff should show below your jacket cuff, just as a half inch of shirt collar should show above your jacket collar.]

Lastly, another great investment is your brand presence online. For just $12 a year you can secure your own URL on GoDaddy.com, and for free you can redirect to About.Me page or your LinkedIn profile. On the higher end, you can hire a designer to create an elaborate web presence, including a color scheme and design to carry over to business cards.

6. Get organized

In short, get your sh*t together. Clean up your workspace. Organize the files in your home and on the computer. Back up your hard drives. Throw away anything you don’t need, and put the important stuff where you can find it. If your home and life feel organized, so will your business.

7. Assemble your team of experts

Assemble your team. Even pro golfer Phil Mickelson has a swing coach, so don’t be afraid to ask for professional help. Although it doesn’t come cheaply, the following professionals can often save you time and money in the long run:

- Financial planner: For assessing your financial status and investments while you build your business and look for work or clients
- Attorney: Can help you set up an LLC or other business entity
- Accountant: Can help you navigate the tricky world of entrepreneurship and self-employment taxes
- Business coach: While they can be expensive and an experienced mentor can be a good substitute, often times a career coach can be worth the investment as they can help you accelerate your earnings

Also see: The Hopkinson Report Episode 147: The 10 people you need to successfully publish (or self publish) a book

8. Embrace community

Realize that if you are suddenly working from home after a long career in an office, you might be in for a culture change. Some people thrive on their own, but others miss the banter of the office and need a larger sense of community.

For some, the perfect answer is a coworking space. Whether it is a monthly membership or just purchasing a day pass and working remotely once a week, coworking spaces are a great answer to getting work done while interacting with others in your situation.

9. Network network network

I can’t emphasize enough how important it is to network. In fact, I set up 21 networking meetings in the first 60 days after I left Wired and started working for myself (yes, I kept a spreadsheet), and they were enormously helpful. Of course, not being in the office 9 to 5 and being able to take long coffee meetings at all hours of the day was a nice perk. But what was interesting was that this ended up not being just a one time set of meetings with my connections as I was building my business, but rather something that has continued on constantly in my business.

It’s also important to align yourself with key influencers in your network. Some connections will be more valuable than others and help you take your business to the next level, so be aware as you build this team of people closest to you.

10. Commit to your health

Lastly, there are turning points in your life when you can choose one direction over another.

- A month after losing my job I started having very bad back pain. Was it my bed? A sports injury? Stress? None of the above. I traced it back to the fact that I was now working at my home computer for 8-12 hours a day, and my chair was a basic wooden kitchen chair from IKEA.

The solution was to tap into several points I’ve mentioned… investing in myself, cutting costs, embracing the community, and committing to my health.

Rather than buy a cheap office chair, I did a ton of research on the best chairs on the market, tried several to see which fit my body type best, and decided to invest in a top-of-the-line Herman Miller Mirra chair worth $1200. However, I embraced the community of Craigslist, cut costs, and was able to buy the exact one I wanted from someone across town for $250 and a $10 cab ride.

- If you’ve spent years going out to lunch with co-workers at the fast food place near the office, only to put on a few pounds and get accustomed to that post-meal haze, if you’re working from home, you have a choice. Stock your fridge with healthy foods that will fuel your body throughout the day.

- Finally, if you’ve lost your job and are thinking about cutting out that monthly gym membership to save money, make sure it’s the right decision. Richard Branson, one of the most successful entrepreneurs of our time was asked to answer the question, “How do you become more productive?” His answer was a simple two word answer: “Work out.”

For myself and millions of others, working out leads to lower stress, better sleep, higher self esteem, healthier eating habits, better posture, and just a boundless amount of additional energy to out back into your business.

Once you have these 10 things in place, you’re ready to attack your new business.

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?

The goal was two-fold. First, to continue the fun tone of the posting and to find someone that had a sense of humor, and second, to see how many candidates utilized their internet research skills to get the answer.

The article goes on to describe how that single question surprisingly worked as an amazing reflection of the quality of candidates that made it through to the next round.

When I scrolled to the bottom of the article, I saw that there were several comments, and that’s when my heart skipped a beat. Let me share some with you:

The Haters

“I’m sorry, but this article makes you sound like a narcissist.”

“Sorry, but this article makes you seem like a megalomaniac.”

“I agree this article makes you sounds like a d-bag that no woman in her right mind would want to work under.”

“I read the piece… My deduction is that it was written by a stuck up self serving pompous person who considers himself to be “corporate elite”… I can only imagine what it would be like to have the author as an immediate supervisor.”

“You should be ashamed of yourself! This article really makes you sound like a horrible person!”

“Such an arrogant little man.”

Ouch. Those are some pretty pointed comments, right? What’s interesting is that salary.com uses Facebook comments, so the old defense that people are cruel on the internet is because they are anonymous doesn’t hold. Maybe that was worse! I could actually SEE the photos of the people looking back at me!

My first and most immediate concern was that I had written something technically incorrect or false or offensive.

Right now I am writing up to 10 articles a month, writing and responding to 5 different email accounts, managing 2 Facebook pages, a LinkedIn profile, Foursquare check-ins, and 3 Twitter accounts. Sometimes I write early in the morning before I’ve had coffee. Sometimes I write at 2am when my brain is shot after a full day. I am going to make mistakes.

Also, more and more of our opinions are displayed in the public eye, and with the 24-hour news cycle that we live in, people notice. It could be a politician with a camera phone or a talkshow host on the radio. One slip and you’re done.

Look at the example of comedian Gilbert Gottfried. His IMDB lists him in more than 100 titles. He was an Aflac spokesman for more than 10 years. He had sent more than 3,000 tweets. But he was fired based on a handful of inappropriate jokes on twitter. He’s a comedian!

It had a little while since I had received such immediate feedback from my writing, and to be honest, I climbed out on the ledge a bit, firing off an email to several trusted sources to get their take.

The Feedback

The editor: My first email was to Aaron. Because this was my first post on his site, I wanted his advice on how they handled things. Do they delete comments? Ignore them? Respond to them? Should I clarify something in the article? His advice was that his writers often jumped into the comments to interact with the readers, but advised me “not to start a flame war.”

Mentor 1: My next email was to one of my mentors at Conde Nast. I knew she’d be uniquely qualified to give me the perspective from the company angle to see if I had stepped over the line somewhere.

Former interns: Next, I went right to the source. Those close to me know that mentorship is a huge part of my lifestyle, and that I stay in touch with people that have worked for me. I wanted to get their take on the matter, and make sure I had the facts straight.

Friends and family: This was more of just sharing the story and looking for a little sympathy. The majority of the feedback was of the “Eh, ignore the haters” variety. My friend Phil said “Welcome to the World Wide Web. I’m a bit surprised you would send me an e-mail asking me about this, but I can also understand why. You of all people know that once you’re in a position like the one you’re in, and once your work is exposed to the masses, there’s BOUND to be a portion of the online population who you’re going to rub the wrong way. Don’t listen.”

Mentor 2: Finally, I had great talk with the current mentor that I speak with weekly, who helped me re-focus and put everything into perspective.

In the end, I’m actually a little embarrassed how much I let it get to me. I know from the book Strengths Finder that my personality has a cruel twist of fate… one of my strong characteristics is that I am comfortable teaching people and putting my opinions out there, but another is that I can be more hyper-aware about what others think about me.

The most important thing you can do from this, or any experience, is to learn from it. Here is what I suggest:

How to react to negative comments:

1) Ask questions
The first thing to do is go back and re-read what you posted.
- Is there anything you said that was inaccurate? If so, move quickly to correct it.

- Did you accidently say something that could be offensive? If so, issue a genuine apology.

- Is there any truth to their comments? You might have to dig deep to look at this one. Am I a horrible person, a terrible manager, or a little man? No. But could I be considered a narcissist? Well, lets look at the facts. I’m first born, I’m a Leo, I enjoy public speaking, and I started a blog and podcast in order to spread my ideas to anyone that wishes to listen. So while I don’t enjoy the term narcissist, lets just say I am not shy when it comes to expressing my opinions.

2) Consider the source
A comment from a CEO on a NY Times column should be weighed more heavily than one from BiggButtz93 on YouTube.

My mentor sent me an article called Is everyone entitled to their opinion? from Seth Godin, which sums it up very nicely.

If you like, you can also go deeper. What do you think the commenter was really feeling when they lashed out? I realized that my post was on a job-oriented website, and the gist of the column was a tricky interview question. It’s easy to take the leap to assume that some of the readers of that site might be suffering through a long bout of unemployment during this recession, and feel that the hiring process is fixed against them.

3) Have a plan
Look at your type of writing, your level of exposure, and your personality and have a plan.
- Are you the type to simply say “I will never read the comments.”
- Perhaps you’ll take the middle ground and read over the comments quickly to get some feedback, but not react to them.
- A third way to go is to jump right in and go toe-to-toe with the audience, explaining your side and engaging in a conversation.

If the discourse is happening on your own blog, or you are a community manager of a major brand, it’s helpful to have a policy in place. Have a terms of service that outlines what is and is not acceptable from users.

4) How to respond
If you do decide to wade into the shark-infested waters, do so with purpose. I can’t explain how important it was for me to have a support team in place to first get the perspective of those I really trusted.

The next thing you might want to do is to step away and give it some time. That can be extremely hard to do when people are attacking your brand, and there are times when you’ll want to respond immediately.

However, in my case, as the article circulated to a wider audience, a funny thing happened. As people saw the negative feedback and looked closely at the article, they stepped in to defend me. If I had come to the site 24 hours after it posted, I would have seen that only 20% of the feedback was negative, as opposed to the 80% when it first launched.

A good phrase to keep in mind regarding this is “Dilute, don’t delete.” What this means is that in most cases, you should not delete the vitriolic comment. This only serves to “feed the trolls” and make them angrier. Far better to have 5 positive comments appear to outweigh the 1 negative one.

The exception to this is when the comment is truly offensive. Where to draw the line? This is something you can outline in the policy in step 3. For example, some sites may ban comments if they contain profanity, threaten other users, or reveals personal information.

When replying, swallow your pride and leave your ego at the door. Respond from a position of helpfulness.

5) What it means
What could possibly be a positive outcome to people attacking your character? Well, it could mean that you’ve taken things to another level. Elvis Presley, MLK, JFK, and just about every other musician, politician, writer, or celebrity will tick SOMEONE off when presenting an alternative viewpoint. Congratulations, you’ve struck a chord.

A hearty discord mans you’re sparking conversation, moving people to action, and growing as a content creator. Trust your gut and use it as fuel to become even better.

Feeling overwhelmed? The 4 times in your life you should say Yes, and the 8 questions to ask before you do.

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A woman in the front row stood up among a large crowd of her peers to ask a question. She was young, stylish, and professionally dressed. The scene was a panel at the Women in Business Conference at American University, where I had the pleasure of running two workshops (salary negotiation and digital marketing).

I didn’t have time to write down her exact quote, but the context of her question was this:

“Sometimes I feel so overwhelmed. I’m working for this one company, doing projects for two more, I get asked to write for some other things, then a friend asks me to go to an event, then I try to volunteer for something, as well as keep up with social media and have time for family and a personal life too…”

“How do I learn to say no?”

The panel was made up of five alumnae of AU, all successful businesswomen with extensive career experience.

The topic of work/life balance is a common one here on this blog, and it was brought up several times at the conference. In my short time as a solo entrepreneur, I’ve talked to many people that have warned me against being overwhelmed. The great part about being on your own, is that you have so many awesome ideas, and can’t wait to execute on them. The problem is, trying to focus on what you like the most and what is going to pay the bills.

In countless conversations and blogs, I’ve heard people talk about the need to learn how to say no. Thus, I was looking forward to hearing the perspective of the people on the panel.

Which is why I was pleasantly surprised at the answer that was given.

“Now is the time to say YES.”

She explained that things are only going to get more difficult as she got older, as marriage and kids and more come along, and how important it is to do everything you could now to find the path in life that is going to make her most happy.

The answer really hit home for me, when I thought about my situation at that very second. Here I was, volunteering to speak at an event for free. It was a 5 hour drive each way, with expenses for tolls, gas, parking, and breaks at roadside Burger Kings. And while I stayed at a friend’s house for free, I paid them back with two excellent dinners. So why did I say yes, when it could have been easy to say no?

Upon reflection, I came up with 4 times in life when now is the time to say Yes.

1) Childhood
The football team, glee club, the school play, Boy Scouts, space camp, learning the trumpet, ballet, video games, rollercoasters … as a kid you should be up for anything. Your parents will play a big part of this, but you never know if you will be the next Julia Child or playing drums on Sweet Child O Mine if you don’t try a lot of different things.

2) College
College may be the ultimate time to just say yes. A single class, a single teacher, or a single chance encounter might alter the course of your life. Current CBS Sports broadcaster Jim Nantz used to do mock interviews with his roommate Fred Couples about winning the Masters when at the University of Houston in the late 1970s, and in 1992 their dream came true as Couples won the green jacket and Nantz was there for the interview. A friend of mine once told me, never say no to a road trip. That about sums up college right there.

3) Your first job
You’re the new guy on the block and everyone is watching you. If you’re like most people, you want to prove to your new company that they were right to hire you and that you are going to be an amazing employee. One way to do that is to take on a little more than you can handle – and then knock it out of the park.

I’m not saying dive right in with 80 hour weeks or consistently working till midnight, but you should make it a habit of learning everything you can from everyone you can. Ask to be introduced to people in other departments that you work with. Go out with the gang after work for a drink. Volunteer for the company charity event. Lend a hand on the new project that is getting all the buzz.

One great point that a panel member made however, is to let your supervisor know early if something is going wrong. They gave an example of someone that had a project due, and it was a week late. When the employee finally came to their manager, they told them that they were having a hard time learning something, and just didn’t get it. The problem with that, is that the week had been lost and the project was now way behind. If they had come to the manager earlier, they could have worked through the problem before it got to a critical point.

4) Your own company
The common thread here is saying yes when something is still new… your youth, your education, your career. I agree with the entrepreneurs that say that you need to find what your company does best and do it better than anyone else, and not let anything else distract you.

On a daily basis, you need to know what are the items that absolutely must get done, and say no to unnecessary emails, useless meetings, and time sucking social media.

In a broader sense, you need to be firm and say no to requests that don’t help you toward your goals, or detract from your personal relationships.

However, for someone in my situation for example, I am saying yes more than ever. Right now I know the message I am focused on (career development and new media), but am in the process of working through the medium. Thus, I am writing, speaking, teaching, podcasting, coaching, and hosting events.

What becomes really important, are the guidelines you put around what you say yes to. Questions you need to ask yourself are:

• Does it make you money?

Let’s face it, when you go from a full-time paycheck to hustling every week, the focus on bringing in revenue rises to the top. Should I write that blog post or go through my emails? If you’re getting paid to write that article, that comes first. The danger with the money issue is that it can lead you to do things that are not in your core strengths because it will pay the bills.

• Will it lead to making money?

Right on the heels of the first point, this question makes you take one step back on the equation. Let’s say you are asked to speak at a conference, and you won’t be paid for it. Before you say no, if you are able to secure future consulting clients, sell your products later to attendees, or meet someone there that will lead to a future paid speaking gig, then it’s worth it.

• Will you learn a new skill?

If you are asked to do something that might take up a lot of time or not pay, but you learn a new skill in the process that will help your business, you can view it as a long-term investment.

• Will it expand your network?

This is a tough one because it can be hit or miss. The panelist told the audience member “don’t worry about missing any particular happy hour or charity event or art opening because this is Washington DC, there are 100 of those every week.” When deciding on an event, look at the quality of the audience that is likely to attend. Will there be potential clients there? Businesses in related industries that you can work with? People you can learn from? I usually set the bar low with my “just one” theory, meaning that if I meet just one person at an event that can help me move things forward, then it was worth it.

• Will it help a close friend or family member?

This is another one fraught with peril depending on the strengths of your relationships. A coworker asks you to attend their book release party and you’re free that night? Sounds like a no brainer. Your brother-in-law asks you to help him move for 6 hours the day before an important project is due, that’s a more complicated decision.

• Will it take a lot of time?

There’s a big difference between stopping by a networking event for a colleague and agreeing to design a new website for company. It’s important to know what your time is worth and adjust accordingly.

• Is it fun?

A person has to have a little fun, right? Is the event you’re considering in Vegas or Miami? Does the app you’re working on have to do with helping people do happy things? I’m doing a speech to an obscure group next week because I get to hang out with one of my best friends from college in the process.

Here is a personal example based on all of the above. I was recently asked to teach a Twitter Marketing class at Media Bistro and had to make the decision. Here is how it breaks down:

Drawbacks:
- I was hesitant at first because it was outside my core focus. Although I had done years of social media work, I was now trying to focus on career development moving forward, so this was a slight step backward.
- As far as timing, I knew I had some previous presentations that I could pull from, so that I wasn’t creating the course from scratch. However, it would still be a 5 week commitment and a lot of research and development. As it turned out, I took a lot longer than I anticipated, including a few 3am nights.

Benefits:
- The course was taught online, so it gave me freedom to work on it when I wanted, and even do chat sessions from anywhere. I actually did one of them from DC the night before the conference.
- The class was half online chat, and half webinar presentation. Not only did I want to explore this format since I had never done it before, the webinars were produced using a program called Camtasia. This is something that I really wanted to learn, so this would force me to pick up a valuable new software program and add it to my skillset. I now feel I am an advanced Camtasia user, and could use this program to produce a webinar for my personal courses that I could sell.
- The class paid well.
- Since Mediabistro was a well-known, well-respected media company here in New York, being a teacher here gives me some added credibility.
- Additionally, I felt that if I did a great job, it could lead to more opportunities to work with them. Sure enough, even before I finished teaching the class, someone there had reached out to me with additional opportunities.
- As a bonus, I’m really having fun with the students. The chat lets me show my personality, and they’ve been super responsive, have asked great questions, and are learning a lot.

• Is it fulfilling?

In the end, this is the question you really want to answer. If you’ve built your lifestyle around doing something that you are passionate about, then all of the other things will fall into place.

I’m honored that my sessions at the Women in Business Conference were extremely well received. Every person that came up to genuinely thank me and tell me that they learned something lets me know that I am on the right track in building a business.

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.

This time around, I sat down with Lindsey Piscitell, Director of Global Marketing, and Nicole Padovano, Manager of Marketing and Partnerships.

Listen to the full interview to get the entire scoop, but here is what we talked about:

- Their expansion from 30 cities to 36,000 worldwide
- Lindsey’s background, including her “big break,” when she went to fashion event and one of the assistants at the event was a no-show, and she jumped in, did well, and ended up getting a job out of it.
- Nicole’s background, including never getting tired of talking about travel, and her would-be rockstar life.

How does Roomorama work?
- Roomorama is a peer-to-peer short term rental marketplace, catering to young, upwardly mobile, educated people who are not looking to rough it, but shy away from the hotel model and want to live like a local.
For the host – it is free to list, the Roomorama team vets the property, speaks to the host to make sure it exists, and then it is open for people to send in inquiries
For the guest – they are informed about inventory, understand it’s not 5 Star hotel, but will interact with enthusiastic people about their city, who are also more likely to show people around

- On the business side, Nicole works for with the perks program, which includes luggage shipping, car service for the airport, restaurants, spas, etc. She works on outreach in acquiring new perks, and also partners with art music and international events. One thing is for sure, people love give-aways, whether it is a tote bag or free concert tickets.

Handling the competition: The question that needs to be asked:
Coke and Pepsi. Apple and Microsoft. Avis and Hertz. Any good business has it’s competitors, and this marketplace is no different. Although they were founded within a few month of each other, Roomorama’s main competitor AirBnb grabbed a lot of splashy headlines when the Silicon Valley-based startup received (according to Crunchbase) $7.2 million in funding in November 2010 and $112 million in July 2011.

So while it might get annoying when people say “Oh! You’re just like AirBnb!” and assume that Roomorama is a new player to the game, the fact is that in many ways this has been helpful. This happens in business all the time, because people want to easily ground what a company does based on a model that they know. For example, “We’re the Netflix for video games” or “We’re like child day care, but for your puppy.” So I asked…

How has the presence of AirBnB affected Roomorama?
Lindsey explained that a great thing is that any press that they get, the benefit comes to them as well. My guess is that whenever a major publication is talking about the new trend in renting out your home, the party line goes “Online sites such as AirBnb, Roomorama, and others…” For example, this New York Times article Surfing for a Vacation Rental.

Additional reading: Is there room for more than one Airbnb?

Lindsey went on to explain that in many ways, the industry is still in a stage where raising awareness is important, so they to make the concept of Roomorama more familiar.

What makes them different?
- 80% of properties are serviced apartments or owned by property managers
- It’s less about sharing bedroom in someone’s apartment, vs. staying in a professionally managed property.
- Roomorama is a bit more premium and higher level service

With their concierge program, Roomorama might also be the better for business travelers, who expect things like wireless internet and a washer/dryer, and they have the people in each city deal with that.

Since Roomorama was bootstrapped by a NYC couple, while AirBnb was a Silicon Valley startup with $120m in venture funding, what differences do you see in how they are run?

There is still that last hurdle to get over… Handing over keys to a stranger. How do you ease that fear?
- Employees and founders do it
- Customer service works around the clock
- Verification process. Doesn’t go live until it has been verified
- Identity checks (since the beginning)
- Cancellation policy
- Certified guest status

How does the money change hands?
- Roomorama takes money and keeps it in escrow
- 6 digit payment code mailed to the guest when they book the location
- Once they go to the property, ensure that it is legit, they hand that code to the host, and the payment is released to the property owner
- Therefore, guest knows that if they show up and the place doesn’t exist or not what promised, they’re not going to hand over the code
- It protects both sides

What trends are you seeing in the marketplace?
- People are latching on to idea of “repurposing their space” (home, apartment, empty office space)
- People want to be tour guides in their city
- The “gig economy” is the future
- The “third office”

Examples of Roomorama clients:
- Some pay their entire mortgage by renting out their place
- A people quit their day job and only rent out their properties for work
- Big example… the co-founders Jia and Fede quit their day job for this company

How can I list my apartment to make it most appealing?
- Photos photos photos
- As much details as possible

The big news: Roomorama is merging with Lofty.com
- Lofty is based in Europe
- Largest aggregator of short term rentals in the world
- $2.1 million funding injection
- New company will be called Roomorama
- Perfect match since Lofty has incredible inventory, Roomorama has a great process

How do they maintain work/life balance?
- Nicole – startups can be hard work and long hours. Try to be out by 630, most likely 730
- Lindsey – often there till 9pm or longer
- Try to make work environment fun with high morale. Just remember because this is something that they care about and believe in and think is fun. Don’t let that slip away. Everyone should work at a startup at one point

How often are they looking at people’s postings?
- Part of the job (“regretfully”) have to pour through gorgeous lofts in Tuscany
- Always looking at cool new things

Favorite travel destinations
- Lindsey got to go to Singapore… then over to Bali for a week
- Nicole’s recent favorite: Spain
- Most popular destinations are global cities:NYC, London, Paris, etc
- On the rise: Southeast Asia and Australia… embracing the idea of opening up their homes
- Wildcard city… Phuket

Most valuable piece of business advice?
Lindsey – trust your instincts. In a startup, not a lot of experience in many areas. Troubleshooting all the time. But entrepreneurs also have something deeper inside. What makes sense to the mass market? Through all the trials and tribulations, trust your instincts and don’t lose site of that.

Nicole – Listened to interview with Ben Silbermann, founder of Pinterest, who said “Don’t take everyone’s advice”

Roomorama.com
Facebook.com/roomorama
Twitter/roomorama
Blog-o-rama

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.

Here is a 6-step action checklist:

1) Control your emotions

Everyone reacts differently in a crisis situation. In fact, emotions when losing your job are similar to unceremoniously getting dumped by your boyfriend or girlfriend: anger, confusion, disbelief, sadness, fear, and self-doubt.

We’ll start with the obvious and say that while angrily throwing chairs around might make you feel good in the moment, it’s going to reflect badly on your integrity down the line. Likewise for bursting into tears. Although it may be difficult, you’ve got to spring into action and think logistically.

Resist the urge to press for more details… Is this about my performance? What can I do to change this? What if I take a pay cut or vow to work harder?

In reality, all of these things have been considered already and the decision has been made. There’s nothing you can do about it, so focus on actions moving forward.

2) Evaluate your timeline

In cases with high-level executives or when sensitive company information is at stake, someone from Human Resources – and possibly security – may instantly appear to confiscate your ID and escort you out of the building.

In other examples, you’ll be asked to stay on staff for a few more days, allowing you to have a “soft exit,” wrapping up projects with existing clients and transferring knowledge to whoever will be taking over your job (always an awkward transition).

Determining which scenario is happening to you will dictate how quickly you need to do the rest of your tasks.

3) Back up your files

What a company fears most (besides the chair-throwing incident) is a disgruntled employee stealing private company information. To be clear, a scenario where a laid off salesperson grabs their “Rolodex” of client names with the intention of luring them away is both illegal and unethical.

Further complicating things in the digital age are the myriad of passwords that employees have for company servers or social media sites. With access to a company’s brand page on Facebook or Twitter, an angry employee can spread his displeasure to millions within minutes.

According to the 2008 FBI/Computer Security Institute Computer Crime and Security Survey, losses due to attacks from inside the company happened 49% of the time, resulting in an average loss per respondent of $288,618.

Again, I want to emphasize that I am not advocating taking any company property that doesn’t belong to you. The fact is, most employment contracts specify that everything you do and create while at the company is legally theirs. No questions asked.

However, what about retrieving personal information from your work computer? Is it a good practice to keep your work files and personal files completely separate from each other? Of course. But some people may not have a computer of their own. So if the only place the seating chart spreadsheet for your upcoming wedding resides is on your company laptop, your boss will usually understand.

In the middle can be a gray area. What if you work at a non-profit and there are photos of you at a charity event that you hosted for the company? What if you work at an advertising agency and edited an award-winning video, and want to use that in your portfolio? The relationship you have with your employer will dictate how these questions are answered.

4) Inform the people that work for you

When I was most recently laid off, it was very important to me that the four employees that I managed hear the news directly from me. They surely knew that something was up when they received an urgent request to drop everything for a meeting, and the news came as a shock to them. However, they felt better that they were able to hear the entire story first-hand, and then be able to ask questions.

5) Get everything in writing

There’s a good chance that the company is way ahead of you in terms of the details of your departure. Consider all of the possible elements:
• Determining your last day
• Receipt of your last paycheck
• Claiming unused vacation time
• Severance pay
• Bonus eligibility
• Continuation of health benefits
• Retirement savings accounts
• Unemployment assistance

There’s no way that you can process everything at once, so be sure they give you everything in writing. Do not sign anything until you’ve had time to go through all the details and ask any questions.

6) Control the message

This is one of the most important steps in the process, but one that few people consider. In the new economy, people are becoming their own media companies.

Even if they have a full-time job, they “market” and “advertise” themselves as they craft their own personal brand on Facebook, Twitter, online video, and photos.

What they need to do in this case is also be their own publicist.

It’s a sad fact that any kind of office turmoil will immediately be followed by office gossip. Human nature dictates that there will be some people thrilled to be the first person to inform everyone, “Did you hear the news? Joe and Sue just got fired!”

Rarely are all the facts correct as the gossip spreads, and the sentiment at best is “Poor Joe, he must be devastated” and at worst “I bet it was because he failed on his latest project.”

What follows is the outline of an email that I sent to employees in my department that I was close to, and the intention behind it.

“Hello, by now you’re probably aware that my job was eliminated this morning during the reorganization.”

[This addresses the situation, emphasizes the fact that it was a result of the restructure and not performance-based, and gives people words to repeat].

“However, I will be here through the end of the week to help with the transition. During this time, you don’t have to “tip-toe” around the issue so feel free to stop by.”

[When something like this happens in an office, people don’t know how to react. In my case, I immediately saw how awkward everyone was, as they didn’t know whether to avoid me or to console me. I broke the ice by telling them I was fine and this made sense to them since I cooperating during the transition].

“In fact, rather than feel sorry for me, you’ll probably want to wipe the smile off of my face since I’m actually really excited. As you know, I have a myriad of side projects including my book, my blog, and speaking opportunities. I’ve already started researching working remotely from Buenos Aires.”

[Is this bragging a bit and putting a PR spin on the story? Yes. However, the reason it works is that it was 100% true. People knew of my side interests, I had already started developing a plan to quit my job in the next 6 months, and I ended up keeping my promise – I was working from a café in South America exactly 6 weeks later.]

If done right, the sentiment can turn from “That poor person lost their job” to “Hmmm, I kind of wish I didn’t have to work either.”

The gossip crowd loves when someone is blindsided by news, so another alternative would be to say “I knew with this economy no job was safe, so fortunately I’ve kept my resume up to date, I have a wide range of professional contacts, and I’ve already started planning out companies that I am going to reach out to.” By doing so, you’re showing that you are being proactive about the news.

The final step I took was emailing a group of employees, vendors, and contacts outside of my immediate department. For me, this included the editor in chief of both Wired Magazine and Wired.com, the close staff I worked with in the San Francisco office, and all the various mentors and fantastic coworkers I had worked with in this large company over the past 5 years.

I quickly detailed the situation, said what a privilege it was working with them, and gave them helpful information on who to contact for my old obligations, and how to keep in touch with me in the future. Again, it really helps if this was true. I really did enjoy my 5 years there, and made a lot of good friends. High-level executives don’t like to be caught by surprise with information, so they appreciate being told the facts right away and being in the know. Everyone can be gracious when things are going well, but taking the high road when situations change shows your true character should your paths cross again.

By following these action items, not only can you avoid burning bridges, but you can actually build some on the way out. That’s a good thing for any kind of relationship.

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 interviews Nate Cooper, a former Apple employee that is now teaching technology in New York, and his use of kickstarter to fund his webcomic, skillshare and meetup classes, coworking spaces, and the startup bus.

- Download podcast: Via iTunes | Save to computer (Right click, Save As)
- Play it below:

The following are some excerpts from my awesome interview with Nate Cooper. Check out the entire podcast to hear the whole interview.

Nate’s background
After moving to New York City from California without a job, this ‘independent academic’ worked his way up from being a seasonal hire at Apple, to full time employee to event trainer. Jim asks what is it really like to work at Apple, and what was his greatest experience there. Nate talks about the fact that since the Apple brand can attract such a quality, creative workforce, the type of people he got to work with were really amazing. Many went on to some really high profile jobs.

The conversation moves to how Nate made the transition from working the floor at Apple to running their events and training, and the reason he decided to leave.

Meetup
Nate credit’s meetup.com as the online tool that inspired him to take the next step in his career. Because he was excited about teaching, here was a way for anyone to get online and easily organize people into classes around a given topic.

Jim wonders, “Are we spoiled in New York City?” The stats would seem to indicate so. A search for internet and technology meetup groups numbers 276 in the New York area, vs just 14 in Phoenix. Even major cities like Boston (47) and Chicago (55) have fewer than a quarter of the number of available groups. Ironically, it was our mutual friend John Murch (from Episode 146) — who I met at a meetup — who introduced us.

Our connection worked as successful ones often do… both parties benefitted.

- Nate contacted me because he was looking to turn his course into a book. As he spoke to his network about this, my name came up in 2 different conversations based on my experience with technology and publishing.
- Meanwhile, after getting laid off just days before, I was firing “what do I do now” questions at Nate, since he had been working independently for almost a year.

Freelance advice
The one thing Nate kept hearing over and over as advice for those trying to go freelance… You just have to do it.

In his first year, he has seen projects take off and others fail, but he has learned to adapt. A site like Meetup makes it easy to try something out and see how it goes. The downside of too many meet ups might be that there is TOO much going on for people to focus.

Key advice
I realized that Nate had hit on the very thing that this new direction of my blog was going to be about.

Between Wired and Apple, we were at some pretty great companies… names that people would die to work for. Living and working independently sounded like a dream, right? Everything you hear about working remotely, hanging out at home, and controlling your own hours. The only little problem is, how do you make money? We bonded because we were both teachers at heart with the same problems…

- Meetup and Skillshare were great, but how do you best leverage them?
- How do you find the sweet spot when charging for a class?
- How do you market it to get the word out?

Reboot Workshop
We start to talk about why and how do we decided on the Reboot Conference. Advice he got was to learn by doing, so we figured maybe we just get a bunch of people together that we like and see how they do it. We handpicked things like accounting, storytelling, social good, got all these people together, and just went for it. See the next episode for a full analysis.

Startup bus
Our thoughts then turn to the Startup bus. Like SXSW, some people are like hmmmm, what’s that? While others are speechless with excitement.

For those not in the know Startup Bus is a “hackathon” on a bus. It’s a 72 hour trip from various cities (NY, DC, Boston, etc) to the SXSW Interactive conference in Austin, TX.

During the trip, the riders put together a company, completing as best they can by the time they pull into Texas. What was surprising was that it wasn’t just a bunch of website geeks, but actually hackers, designers, programmers, and even [gasp] business people!

Kickstarter
Nate’s flagship course is “website bootcamp for creative professionals,” a course that is not really HTML, not really servers, but weaves in and out of the themes. There are a lot of people that need help and know certain terminology, but don’t know what other things mean or how they work, like FTP or whatnot.

His Issue?
The class has been successful here in New York, but he had no way to reach people outside of the city.

He had already been writing a book, and since he wanted to get it across to a non-technical audience, he had a seminal moment: make it into a comic book. He teamed with talented illustrator Kim Gee and is funding the project through Kickstarter as a way to teach a technical subject to a broader audience.

What is Kickstarter?
It’s a new social media way to raise money, sort of a grassroots way to fund a passion project. If you don’t need ton of venture capital, just some help starting, pitch your project to the crowd and they will tell you if it is good or not.

Key takeaway and advice
In a microcosm, Nate had illustrated the exact steps that someone can take to lead a better career lifestyle:
1) Experiment with your core skills. Nate knew he wanted to be a teacher and was good at it, so he used free services like Skillshare and Meetup to rapidly test his ideas.
2) By doing so, he knew what was successful and what wasn’t within days and weeks, not years.
3) Once he knew what resonated, he was able to hone it with each successive class
4) Finally, once he had a great product in person, he could then reach people outside New York by creating a digital product

The other huge piece of advice was building relationships. We know someone at almost every co-working space in the city, yet have remained “workplace agnostic” with our business ventures. Coworking functions as the modern day coffee shop – with the difference being that people go there because they WANT to run into others.

Jim says, in a major corporation, you’ve got your collection of management, low level employees, slackers, new people, and old farts.

But in a coworking space, every single person is outgoing and exciting and working on 17 projects at once. Amazing connections continually happen.

Wrapping up, we discuss:
- As a newbie, what is Nate expecting at SXSW and what are his goals?
- What would he do other than his current profession?
- How do you maintain a worklife alance?
- What websites do you visit every day?
Answer: Reddit and Jason Kottke
- What is the first thing he thinks about when he wakes up in the morning?
Hint – his phone is his alarm clock
- What book he puts out to impress visitors
Answer: Book he is reading right now: Where do good ideas come from? by Steven Johnson
- What advice do you have for those looking to start own company, or make the transition

Find out more about Nate at NateCooper.co and @natecooper

This is part of the series: How to work remotely from Buenos Aires

Working while traveling is great, as long as you leave enough time to do the fun stuff!

Here is a list of 10 things to do in Buenos Aires, Argentina:

1. Chill out, eat, or work from one of the many great cafes.
Two favorites for me included Mott with their impressive bar (Top photo, above) and Bar 6.

2. Indulge in amazingly grilled steaks and fine Malbec Wine
Restaurant recommendation: Campo Bravo

3. Have a drink or dance at one of the many clubs and bars.
BA is a night owl city… several times, no matter how late I tried to stay up, I couldn’t even make to the clubs before they OPENED (one night I was there well past 11 and they didn’t open until midnight; at another I was there past 1:30am but it wasn’t going to get going until 3am).

There are enough places along Honduras Street in Palermo for anyone to choose from.

4. Running or walking in Parque Tres de Febrero, their version of Central Park,

5. Recoleta Cemetery
A cemetery is a highlight? Oh yes. The architecture and history is impressive and experience was better than expected in the place that Eva Peron (Evita) is buried.

6. Taking Tango lessons
Definitely the highlight of my trip, I enjoyed the rush of trying to learn something completely new being taught to me in a language I didn’t understand with people I didn’t know in a crowded, sweaty, basement at La Viruta in the Armenian Cultural Center.

7. San Telmo street fair
Not the most exciting thing in the world unless you are really into antique and crafts, but still on the “must do” list. Check out San Telmo and wander around on a Sunday.

8. The colorful buidlings in La Boca
Very hyped and dripping with tourist traps, it’s still a must-see location, especially for photographers.

9. The government buildings of downtown
Touristy sites to see include the “pink house,” the obelisk, riding the old school subway and other things.

10. Taste a bit of home
There are Ex-Pats from every country scattered throughout the city, so if you need to feel at home again, I was even able to catch an NFL playoff football game at Casa Bar.

Note: the one thing I was DYING to do was to see a soccer (futbol) game. However, when I was there it was the height of their summer, so now I “need” to go back.