The Unemployable life is all about being a digital nomad, maybe cruising around the country in a van, trusty laptop at your side, right? Well, for the last 20 years, I can’t say that’s been my experience at all.

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It can be easy to think that highly successful people have just ended up that way, fully formed. The reality is, almost every person deemed to have “made it” makes the same joke:

“I’m a ten-year overnight success.”

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Over the last 20 years, the way we work and collaborate has changed dramatically. The promises of a free agent nation from the early days of the internet have become a reality for freelancers and solo entrepreneurs around the planet.

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Over the last 12 years or so since I started Copyblogger, I’ve had an amazing journey. Along the way, I’ve also been fortunate to watch the journeys of those who started about the same time, as well as those that broke out in the following years.

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Late last month, I announced that StudioPress, our WordPress design and hosting division, was acquired by WP Engine. It was my first “liquidity event” ever, despite having started a string of companies over the last 20 years.

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Listeners to Unemployable are no strangers to the idea that one person, armed with the internet, affordable technology, and a network of fellow unemployable people can do big things. So you won’t be surprised to hear that the number of one-person businesses earning a million dollars or more a year continues to rise.

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Everyone discovers the power of content marketing in their own way. And ultimately, those who do it well take their own unique path from there.

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On his 30th birthday, Steve Jobs sent the following Hindu saying to his friends:

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It’s no secret that I’m a big fan of partnerships to effectively build businesses without investors. I’ve done it successfully over a half-dozen times.

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We kicked off the year talking about “leveling up” your business in 2018. It sounds desirable (and ultimately, it is), but it can also be a struggle.

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Email was the original “killer app” — everyone uses it, and that’s why it’s been the absolute best channel for digital marketing and audience building. And yes, that’s still true in 2018.

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When you’re working with clients, the goal is to make great money doing great work for great clients. That’s totally doable, if you take the right steps.

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It’s been almost two years to the day since Chris Ducker last joined us on the show to explain the concept of the “Youpreneur.” He’s been busy since then, running the branded Youpreneur community, and managing to write a brand new book on the subject.

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If you’re out there making it on your own economically, the depiction of entrepreneurism in the media likely has you scratching your head. Everyone other than you seems to have their act completely together, right?

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It can be nerve-wracking to negotiate your prices with a new client. Even simply presenting your pricing for the project can cause an uncomfortable squirm.

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Perfect timing can mean the difference between success and failure. But how does it happen? Is it blind luck, or some sort of genius skill that’s unavailable to the rest of us?

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In January 2003, Mike McDerment was running a small design firm when he finally snapped. He was using Microsoft Word to bill a client when he accidently saved over the invoice. It was at that point that Mike decided to build his own accounting software solution.

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Back when the Internet was young and dinosaurs roamed the earth, there was a new thing called pay-per-click advertising. And it wasn’t Google that invented it, although AdWords would come to rule the space.

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What if you could work the same amount as now, but make more money? Or what if you could work less and still make more money?

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Whether you identify as a freelancer, consultant, coach, or solo entrepreneur, there’s never been a better time in history to accomplish so much as a single-person company. Just your skills, some key technology, and a network of virtual assistants and fellow solos can accomplish big things.

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The online dating advice space can be fairly sleazy. Self-proclaimed gurus promise the dating-challenged that they’ll quickly become pickup artists if they just follow the system and play the game.

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When I look back over my almost 20 years as an entrepreneur, I can point to pivotal moments where advice from Seth Godin got me to the next level. So, when I decided to devote an episode to succeeding as a solo entrepreneur, he was the logical choice.

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The very first Internet buzzword, going way back to the 1990s, was community. As the online world moved forward, things became more tribal than communal, but the idea that the Internet allows like-minded people to come together is profoundly true (in good and bad ways).

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Webinars remain one of the best list-building and product promotion vehicles. The event nature of a live online meetup combined with compelling content is a winner, even if you don’t call them “webinars.”

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Since the beginning of the web, the promise of business websites has been that they are like 24/7 salespeople. Prospects can find you at anytime, get the information they need, and contact you.

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Nathan Chan took a familiar route when seeking to escape the corporate world. Like many, he worked his passion project on the side while he paid the bills with a job.

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It’s all about the data if the pundits are to be believed. The more you know about your customers and prospects, the better your business will do.

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More and more people are operating solo, outside of the confines of traditional employment. And thanks to technology and a ton of talented independent contractors, the solopreneur can bring in outsized revenue with a company of one.

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Back in 2009, Joe Pulizzi was one week away from giving up his entrepreneurial dreams and going back to a job. It was a dark time, both personally and in the broader economic environment following the financial crisis in the United States.

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More than 55 million Americans are freelancers — a full 35 percent of our workforce, according to the 2016 Freelancing in America report. And contrary to enduring myths, it’s not because “they can’t find a job” — it’s a conscious choice based on freedom and empowerment.

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It’s the bane of modern marketing. Any product can be replicated or reverse-engineered. Any service can be copied, leaving only execution as a true difference (which comes after the point of decision).

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Owning your own business can lead to the lifestyle of your dreams, but only if you’re very intentional about it. Only you can decide what that dream looks like, and only you can implement it.

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Just recently, Medium announced the intention to start charging a $5 monthly fee for an enhanced experience at the popular site. Also, Twitter is considering a subscription version of TweetDeck geared toward marketers, brands, and other power users.

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As digital marketers, we have websites to attract leads, customers, and clients to our businesses. So it makes sense that the more leads, customers, and clients we attract, the more money we make.

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There are plenty of self-proclaimed content marketing experts around these days. The only thing these experts have ever seemed to market, however, is themselves.

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Everyone loves a good listicle right? The entrepreneurial space is littered with 3 tips for this, 7 tactics for that, and of course the rock steady top 10 tips for “what have you.”

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I was in Austin last week speaking at a conference, and I had an interesting conversation with one of the other speakers. It’s a guy I’ve known for years on the web writing circuit.

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As I’ve repeatedly admitted, the inability to delegate earlier in my entrepreneurial journey was my achilles heel. I worked too hard, paid too little attention to my family, and generally wasn’t happy.

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We ended last season with an Unemployable episode featuring Darren Rowse of Problogger, in which he and I lamented that the kind of human connection that fueled the early blogging movement seemed to be getting drowned out with tactics and technology.

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Emily Thompson is no stranger to the independent business life. She started off with an Etsy shop, and soon began helping other indie business people build their own platforms with web design and coaching.

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Back in the early 2000s, social media was a very different thing. The term came out of the Web 2.0 movement, and the primary components were blogs.

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A few weeks back, we looked at a process that you can use to transform your business. The example I gave was for a freelancer to “productize” an aspect of their services into a neatly packaged product with a defined scope and pricing.

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This week, we’re shaking things up a bit. I took to Facebook and Twitter and asked for questions related to running and growing your business — and got a bunch of really good ones.

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What comes to mind when you think of an entrepreneur? Maybe it’s the gregarious and frenetic hustler, as personified by my friend Gary Vaynerchuk.

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You might notice from the title of today’s episode that I have a thing for alliteration. That’s a copywriting technique, which is not what we’re talking about today.

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Attracting and working with clients can be challenging. Implement the right practices and processes, though, and you can design a stellar small business and lifestyle.

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Last week we talked about the power of positioning when it comes to starting a podcast. We also touched on how sponsorships can become just one of the lucrative sources of revenue that comes from growing your audience.

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Work on your business, not in it.

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It’s been a year-and-a-half since I started Unemployable. And it’s just been recently that the show has started to take off.

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You’ve seen Pulp Fiction, right? It’s the classic 1994 black comedy crime film written and directed by Quentin Tarantino.

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In the beginning, there was blogging. And for businesses looking to build an audience that helped grow the bottom line, it was good.

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Many freelancers dream of the day that they’ll have sources of income other than from client work. Some hope to stop taking clients for good in favor of selling online training instead.

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It’s been almost two years since I started Further, my curated email newsletter about personal growth. And there’s no mistaking that the project was inspired by Dave Pell’s NextDraft.

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Tim Ferriss broke into popular consciousness nine years ago with the release of The 4-Hour Workweek. He’s gone on to create a series of books based on the “4-Hour” concept.

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Back in 2006, Gary Vaynerchuk started a daily video show that turned wine criticism on its head. More importantly, it took his family wine business from $3 million-a-year to a $60 million-a-year ecommerce juggernaut.

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The other day I was listening to the “classic alternative” channel on SiriusXM. Message of Love by the Pretenders was on.

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Many people go out on their own in pursuit of the perfect lifestyle. Of course, “perfect” is entirely subjective.

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Virtual conferences have been around for years. They provide the education of a live event, without the expense of travel, hotel, and other “real world” costs that live events bring.

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The ancient Greeks — notably Aristotle — used anecdotal observation to nail much of what we know about persuasion. The fundamentals of the art haven’t changed much in 2300 years, because human nature hasn’t changed, even as the context in which we operate has changed dramatically.

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In just over a decade, WordPress has become the most popular content management system on the web. And as with any hugely popular open source movement, there are plenty of for-profit companies providing premium themes, plugins, hosting, and support.

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As you likely know, crowdfunding is a way to raise money for a project or venture by pulling contributions from a large number of people, usually online. In 2015 alone, crowdfunding generated an estimated over $34 billion (USD) worldwide.

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Startup, raise money, cash out, repeat. That’s the narrative that Silicon Valley feeds you.

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Of all the components of a holistic online marketing strategy, search engine optimization (“SEO”) seems to mystify many the most. And it’s true that years back, the key to ranking well in Google was a form of dark art.

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As the leader of a virtual company of over 65 people located around the world, I wouldn’t have it any other way. Of course, I had a lot of help from my partners getting to this point over the last 6 years.

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We’re all familiar with the stereotyping of Millennials. Like my own once-denigrated Generation X, “these kids today” are lazy and entitled, right?

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Entrepreneurs and independent business people are always working on the next thing, often on the side while we maintain our current income. And as your mind begins to see the world in a more entrepreneurial way, you’ll spot opportunity everywhere.

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Henry Rollins is an actor, author, spoken-word artist, and musician. You likely know him as the iconic lead singer of seminal punk band Black Flag, which kicked off his enduring career.

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Whenever we get a heavy snow in Boulder and I share a photo of my buried patio, you’ll see an ornate, flame-carved fire pit in the shot (filled with snow, naturally). It’s a custom design crafted out of recycled propane tanks by artist John T. Unger.

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Jadah Sellner and her husband had a simple dream – to own their own business while spending as much time as possible with their young daughter. The couple’s child center on the Hawaiian island of Kauai seemed ideal … until it wasn’t.

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When it comes to creating digital products, software, ebooks, and online courses are what come to mind. But have you ever considered turning how you do what you do for clients into a product?

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There are a lot of artistically-inclined people in the world of freelancing and creative entrepreneurship. Writers and designers come immediately to mind. Hugh MacLeod of Gaping Void is certainly an example of a literal entrepreneurial artist.

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A month or so ago, we discussed the idea that entrepreneurs may have to be a little crazy to succeed. That perhaps the ability to execute on innovative ideas might come from a mental illness or psychological baggage that is turned into a positive.

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On Unemployable, we talk a lot about leveraging virtual teams and collaboration in order to achieve more. And we talk about building an audience that allows you build a bigger business than you could otherwise.

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Today we’re talking to Rand Fishkin, founder and Wizard of Moz. Confident, successful, and the person you want to be like some day … right?

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The other day I was listening to the “classic alternative” channel on SiriusXM. Message of Love by the Pretenders was on.

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Do you believe we were all born to do a certain type of work? More importantly, do you feel you’re doing what you were born to do?

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Have you seen the film The Big Short? It’s about the investor bets made against the U.S. housing market due to negligence and fraud involving mortgage-backed securities, which ultimately led to the “Great Recession” that began in December of 2007.

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As we’ve discussed before on the show, everyone at every level usually has a side hustle going on. It’s the process by which we leverage what we’re doing now to do the next, bigger, and more gratifying thing.

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It’s an amazing time to be a solopreneur. Affordable technology plus the reach of the Internet allows for outsized profits by a “company of one.”

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The saying goes that there’s a thin line between genius and insanity. But do successful entrepreneurs actually parlay mental illness into innovation?

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Freedom is a primary theme of Unemployable. Not everyone wants to “disrupt” and “dominate.” Rather, they want to do the things they want to do, and live the life they want to live.

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We’re big on systems and processes at Unemployable. Naturally, that’s the topic of the first lesson in the free Profit Pillars course that members gain access to when they join the tribe at no charge.

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When I started my first business in 1998, it turns out I did a lot of things right. It wasn’t until May of 1999 when I read a book called Permission Marketing that I realized what I was missing, which led to my first successful business.

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In 1997, a young man quit his job to become a writer. In January 1998, an article he wrote entitled Free Agent Nation appeared in a young magazine called Fast Company, and a career was launched.

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