Real Deal Gurus: 6 Freelance Experts Who Are Actually Worth Following

Written by Bethany Johnson on December 6, 2017

As a freelancer, I’m targeted by every online guru who wants to “funnel” (no, really, funnel) me into a sales pipeline to get me to buy their book, e-course, coaching program or access to an “exclusive community.” The only problem? I don’t really believe most of these gurus are much more than hyped-up hype.

And I’m not the only one who sees it that way. The coaching industry has taken off with “freelance experts” who’ve gotten pretty good at generating passive income — that sweet stuff that keeps rolling in even when you’re digging your toes in the Cancun sand.

But since there’s no barrier to entry, many gurus skip the years of hard work needed to, you know, speak from experience. Instead, they jump straight into creating an e-course or book to sell.

The good news? Some standout freelance experts really have learned by doing — and they lift up their fellow freelancers by teaching newbies, encouraging dabblers and applauding successful indys. Why don’t we shine a spotlight on them, instead?

Jenny Beres

Topping my list is Jenny Beres, whose “Pitching Masterclass” is the only freelancing course I’ve ever bought. Really. After going through it, I was all tooled up and confident enough to make it on my own. She and her co-guru, Alex, offer an ongoing support and learning academy that churns out enthusiastic, high-earning freelancers on the regular. Plus, she’s the only coach I know who rails on phony coaches as vocally as I do.

“Alex and I always tell our freelancers that you must take advice from those who have already accomplished what it is you want to do,” she says. “I see so many people who want to make six-figures freelancing, but who take advice from people who’ve never been able to command more than $100 per project.” Yes, it’s as dubious as it sounds. A quick look at a coach’s portfolio — of freelance clients, not coaching clients — can tell you everything.

Len Smith

Next up is the celebrated “copywriter for hire,” Len Smith. Smith’s signature teaching style is something over 60,000 freelance writers have come to know and love, though his emphasis is on basic copywriting, white paper writing and SEO writing. His courses can be found on the Udemy teaching platform, and they’re usually on a flash sale. You truly don’t need to spend a fortune on the world’s best freelance writing advice.

Brennan Dunn

What makes this website-designer-turned-coach worth following is his story. He started coding for clients as a side gig after hours. As his client list and pipeline grew, he made the leap into full-time freelance work and continued his success. But the only thing holding him back from becoming a top freelancer was himself. So Brennan learned to outsource by hiring help and investing in others. He eventually found himself running a downtown office with 11 full-time employees, pulling in millions of dollars in revenue each year.

Brennan teaches many facets of the freelance lifestyle, but my biggest takeaway from his site, Double Your Freelancing, has been his emphasis on creative diversification techniques for freelancers. Using his advice, I’ve targeted (and won) business in ways my competitors haven’t even considered.

Rosh Sillars

Freelance shutterbugs, rejoice. Rosh Sillars’ website is a deluge of useful and actionable information. I first found his site by searching how to price out photography gigs. Sillars’ site popped up, and the most comprehensive post possible — over 8,000 words worth of assistive information (accumulated over years) — appeared on one page. Here was an e-book’s worth of knowledge I didn’t need to pay for, work for, ask for or even “opt in” for. His generosity shines through every product he creates. From his regular posts to his podcasts, social presence, coaching and corporate training, altruistic benevolence is his signature.

Carol Tice

Another longtime writer and teacher, Carol Tice, is a name all experienced freelance writers have seen and heard. She tirelessly urges freelancers to know their worth and charge clients accordingly. And it’s not just motivational hooey. You see, what sets Carol apart from other mentors is her deep knowledge of where and how to find quality work. Her contributors keep updated, running lists of which outlets are paying writers, how much each gig offers and where to apply. And that’s just on her site.

Ed Gandia

Want to consume your advice without slowing down to read? Ed Gandia’s High-Income Business Writing podcast started as just that — an audio show for writers — but has since morphed into a show for B2B (that’s business-to-business) indys in all creative disciplines. So if you sell your services to a business, it’s the show for you. I’ve learned so much in the last few weeks, all while folding laundry and shuttling kids to school. Start listening, and you’ll learn how to prospect for new work, how to stand out from the competition and why and how to take risks as a freelancer.

Finding Your Own Guru

One of the biggest reasons many freelancers fail to launch is an overload of pricey information. While know-how is necessary, you shouldn’t be emptying your bank account over and over to feed the self-declared freelance experts out there. With the right teacher, you’ll learn the important lessons together so you can get on with building a successful business.

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