THE BLOG
04/25/2016 11:57 am ET Updated Apr 26, 2017

The Secrets of Today's Reigning Lifestyle Entrepreneurs

"Let's get right into it--let's talk about the boobs," says Renae Christine, a platinum blonde Vegas-dwelling mother of three who makes videos where she talks about eating Easy Cheese and tripping over her shoelaces--all while doling out solid business advice.

Christine is what's known as a lifestyle entrepreneur--a career you and I are idiots for not having. When I first heard the words "lifestyle" and "entrepreneur" together, I assumed a) that the person who said it was kidding and b) that this was a job description for someone who helped entrepreneurs decide whether they should buy the Porsche 911 or the new BMW electric. It turns out the lifestyle entrepreneurs are actually the ones buying the luxury cars.

Once I found out about this career, I asked the only logical question: how can I become one of them?

These are people who have figured out a way to earn serious passive income (sometimes up to eight figures) so that they can go about living the lives they want, whether that means surfing every day or training to become a professional athlete or feeding the pigeons in the park. They may not be celebrities in the traditional sense, but in their world, they are rock stars. Rock stars, that is, who are making far more money than most rock stars today.

What these folks are doing to earn their money and title is, for the most part, putting themselves out there, through books and podcasts and online courses, as experts on putting yourself out there, through books and podcasts and online courses. In other words, their job is to teach you how to become them.

Renae Christine sits atop Rich Mom University, a class she's created that teaches people how to make money through a handmade business. She's set to make a cool million this year, has 27,000 YouTube subscribers and receives nearly 6000 emails a month from "besties" who want advice or to just to thank her for her guidance.

But back to the boobs. Christine's are big (while she's too classy to tell me the size, she did admit that they're the same as mine when I confessed that I was 34D). When she started out, Christine was self-conscious about her skin--she says she was prone to acne--and so all her videos were shot from far away. Though she was providing the same solid business advice she does today, the boobs were distracting people from her message. "You get comments from women, like, 'Oh you're skanky' or 'You can't be a real business coach' while men will write the dirtiest things imaginable," she explains. She had, by this point, posted roughly 700 videos.

Then, one day, she stumbled upon a course on teaching online courses and everything changed.

***

Create Awesome Online Courses is the brainchild of David Siteman Garland, a St. Louis-dwelling married father who launched a web show and podcast in 2008 called The Rise to the Top, where he interviewed entrepreneurs like Seth Godin and Tim Ferris; within a few years, it had been download over seven million times.

After years of doing these interviews, Garland noticed one thing: a lot of the people he talked to were miserable (not, it should be noted, Godin and Ferris--they are patron saints of this world).

"Entrepreneurs would say, 'I am making X dollars but I never see my family, I sleep when I go on the toilet and I gained however many pounds in the last two years," Garland says. "I didn't want that. I loved the idea of creating a business around my lifestyle and not the other way around."

That's when Garland accidentally uncovered the world of online courses. This was back in the online course Dark Ages--that is, before someone like Garland was out there showing people how to create courses. But after "obsessing like a crazy person, finding anything I could get my grubby little paws on," he was able to unearth a lot of information.

At this point, he'd done over 300 interviews for his show and so he built a course around the "thing that was right under my nose." Create Awesome Interviews sold for $297, and though he had a relatively small mailing list of 400 people at the time, it made $19,800 in its first five days. Within a year, it had made $250,000 and within two years, a million.

Now that Garland was an expert in creating online courses, he created a class that broke down every single thing he did to make his course successful, and priced it at $997. Today he has seven courses, co-owns a course software company and runs a private Mastermind group for his top level students, which costs $20,000 a year to join.

In 2015, he made $2.5 million.

***

When Christine found Garland's class, she was broke. It wasn't that she didn't have pertinent information for those wanting to make money from handcrafted goods; her problem was that her videos were free and while part of the online class business model involves giving out a lot of the information gratis (more on that in a bit), Christine would choke when it came time for the "sell."

"I learned through David's training that I have a natural tendency to apologize," Christine says. "But he gave me a script for what to say and I followed it." Her first launch after taking his class brought in $1700 and though she now has six-figure launches, "the $1700 meant more because at that point I was looking at homeless shelters," she says.

Christine, like many people I spoke to for this story, speaks of Garland with reverence. And while he's helped launch many now successful lifestyle entrepreneurs, Christine says he has a special knack for working with women. This, according to Christine, is because he talks to women the same way that he talks to men. "He supports you but he doesn't allow you to make excuses," she explains. "If I said to him, 'I have three kids--I don't have time,' he's going to say, 'Well you need to do x,y and z' and not 'Oh, because you have three kids, you only have to do x.'" (Other prominent female lifestyle entrepreneurs who learned from Garland include "Communication Stylist" Nikki Elledge Brown, expert social media strategist Debbie Saviano and Smaller Size Bigger Life founder Heather K. Jones.)

Garland, who's known as "Uncle DSG" to many of his students, is part of a new pack of lifestyle entrepreneurs, which includes Facebook and webinar maven Amy Porterfield, podcast king John Lee Dumas and LinkedIn go-to guy Lewis Howes. They're following in the footsteps of many of the people he used to interview--not only Ferris and Golan but also people like Gary Vaynerchuk, Marie Forleo, Brendon Burchard and Jeff Walker. Yet Garland is clearly a ringleader in this second wave, having coined (and copyrighted) the word "mediapreneur" to describe what they all do. And he's created the airtight online course system that the rest follow.

This, in short, is the Garland system: Come up with your course based on whatever topic most people ask you about. Then email the people you have on your newsletter list, the size of which doesn't matter, and explain that you're always being asked about this topic so you want to know if they have any questions about it. This, Garland says, is not just to get ideas for your course but also because these are folks who will be emotionally invested once you release it.

Next: create a "lead magnet"--typically, videos packed with enough information that the person watching it could theoretically learn so much that they might feel like they don't even need the class. This, in turn, will make them trust you. Then start sending them regular emails but instead of spamming people with the kind of newsletters that make them reach for unsubscribe before they've even hit open, pack them with highly relevant and helpful content. Only then do you hit them with your course.

When it comes to the actual course, use words like "system or "step-by-step." Create a Facebook group for the students. Price your course with a 7 at the end--$247, $497, $997 and other odd numbers (though this move isn't specific solely to lifestyle entrepreneurs; supposedly, ending a cost with the number 7 converts more). Finally, make sure the course is only available at select times because the scarcity factor motivates more people to bite (he recommends doing a five- or 10-day launch several times a year).

It's safe to say that Garland's methods have paid off. He makes a great living, is able to employ his dad to run his business and has a slew of successful students to show for himself. But he also has the time to go to Cross-Fit for roughly two hours a day, spends a good hour every morning playing with his daughter and recently returned from a family vacation to Mexico where he didn't check on his work the entire time. "David is a shining example of what works in this world because he's not pushing and struggling, but instead thinking and strategizing while other people are just staying busy," says James Wedmore--the creator of the hit online YouTube marketing training program Video Traffic Academy.

According to Wedmore, lifestyle entrepreneurs do best when banding together; his most successful course was the result of a partnership with his number one competitor. "I reached out to him and said, 'I think we'd be more valuable if we worked together,'" Wedmore explains. "People can be your competition or your greatest ally."

Ally-hood, you could argue, is crucial here because promoting one another is part of the business plan. They all have massive newsletter lists--Wedmore estimates that his contains around 170,000 names but the number is ever-evolving since he gets about 300 sign-ups a day and as many as 20,000 a day during launches. But because each has a slightly different audience, when DSG promotes Wedmore or vice versa, they're reaching a new group of people. And the cut in these affiliate promos would make a Hollywood agent cream: profits are divided 50-50.

One of the more satisfying promos for both parties is when one of the people involved is largely responsible for the success of the other. This is the case with DSG and Nick Stephenson, a British author who began publishing books in 2011 and then had an epiphany few authors seem to: instead of writing more books, why didn't he try to find more readers for his existing work?

And so Stephenson started writing freebie books and including large graphic ads for them in his regular books. As a result, his newsletter sign ups increased from roughly 12 people a month to 50 and his sales began to steadily increase. Soon, other authors were emailing him and asking for advice on how they could build their audiences.

Stephenson bought and watched one of DSG's courses in a day and, nine months later, his course, Your First 10,000 K Readers, had a six-figure launch. Interestingly, two of the life-changing nuggets he gleaned from Garland were, at first glance, counter-intuitive: one, the higher you price your course, the greater its chance of success and two, the more it's geared toward as specific an audience as possible, the better it does. "You can have a course called How to Market but it's better to have it geared toward authors or plumbers or ballet dancers or whomever," Stephenson explains.

Since Stephenson is an author, it of course makes sense that this is his target audience. And yet, since entering the online course world, he's had to seriously back burner his writing. "Books are still bringing in six figures a year," he says, "but the course is bringing in multiple six figures."

Rest assured, Stephenson doesn't take this money for granted. "I went from a full time job, where I was at the office from 8-6 to being the dad and the business guy at the same time," he says. Now that he can afford full-time help, he can not only work from home but also has the freedom to work whenever he damn well pleases.

Free time is a crucial part of the lifestyle entrepreneur model. Jenny Blake, a former Google employee now living in New York, makes a living through a combination of writing (her second book, Pivot: The Only Move That Matters Is Your Next One, is due out this September), business coaching and her online classes. Despite this juggling, she starts every day with an hour of meditation and contemplation and then reads for another hour. "I only do calls between 11 am and 3 pm because I'm no good after that," she says. "If your body is operating at 50%, so is your brain."

Perhaps because brainpower is so crucial in this world, these folks don't tend to be globetrotting or hitting hot spots. You could actually argue that the lifestyle these people lead is sort of the opposite of what the title "lifestyle entrepreneur" would invoke. DSG uses dorky phrases like "Captain Obvious." Ranae Christine is thrilled to be able to buy her kids new shoes. James Wedmore admits that his office is across the street from the beach but in the same breath says that he really loves working. And in talking about the luxuries his lifestyle allows, Stephenson says, "It's nice to know that I can go see a movie at 11 am in an empty theater if I want."

The rock style lifestyle? No. But I'll take it. I just have to remember to hide my boobs.