Craig Clemens: How I Went From a Broke Salesman to a “Lucky Bastard” Entrepreneur

Craig Clemens: How I Went From a Broke Salesman to a “Lucky Bastard” EntrepreneurCraig Clemens: How I Went From a Broke Salesman to a “Lucky Bastard” Entrepreneur
Every entrepreneur has been there- rock bottom. With no money and nowhere to go, the only way up is to build yourself to success. Is it hard? Harder than anything you’ve ever done before I’ll bet. Is it doable? Absolutely.
I recently had a chance to sit down with renowned sales copywriter and entrepreneur Craig Clemens for an interview. If you’re unfamiliar with Craig’s work, he’s literally the definition of “started from the bottom, now we’re here.”
Craig began in sales when he was 21, bounding around jobs including “boiler room-esque” phone sales jobs, selling credit card merchant accounts, and Direct TV subscriptions, but found himself at 24, completely broke. He specifically recounts one month where he had to sell his TV for $50 to make rent. He also used to go to McDonalds with coupons to get $1 off the value meal for lunch. Talk about being frugal!
After discovering that his friend Eben Pagen was making $70,000 a month selling an eBook called “Double Your Dating,” Craig set his sites on learning from him, and was eventually offered a job with Eben starting at $3,000 a month. At the time this was life-changing money for Craig, but the real value would come in the form of knowledge. Eben was one of the world’s best sales copywriters, and Craig would have the fortune of learning directly from him for the next four years.
Why is this such an important skill in business you ask? Here’s what Craig had to say:
“Learning to write winning sales copy is perhaps the most important thing you can learn in business, as it’s a skill you will use for the rest of your life, whether your actual “job” involves writing or not. Career-wise, it’s recession-proof – every company needs sales, so the demand for great writers who can bring those sales in will always be high no matter what the economy. Sure, you may have to shift from selling yachts to selling economical cars, but there will always be companies needing your service! A great writer can charge 25K or more plus royalties for a single copy package, and smart entrepreneurs will happily pay it, as they know the right sales material can turn their idea into gold.”
Eben’s business eventually grew to $20 million a year in sales… impressive considering all Eben was selling were programs showing men and women how to have better relationships. Who knew?
Craig and Eben parted ways in 2009, and since then Craig has started multiple internet businesses, partnering with his two brothers and a friend named Josh. He also had a run as a club promoter in Hollywood where he learned about deal making and building a quality network of people.
Today, Craig is the definition of a successful internet entrepreneur. He lends his marketing talents to a  company he and his partners recently acquired that specializes in organic cosmetics and skincare treatments. Read on as we discuss his secrets in sales/marketing, the best way to build a quality business network, and the kind of relationship that every young entrepreneur needs right now.

What are some of your tips when it comes to sales & marketing?

“The biggest takeaway would be from a guy named Eugene Schwartz; one of the greatest copywriters of all time… and that would be that in order to sell, you must first enter the conversation your prospect is having in their own mind.

Many make the mistake of trying to “convince” people to buy something they do not want, but this is simply not possible. Unless you are addressing a dream or desire they already have, your prospect will be reluctant to buy from you or even listen to you. That’s why it’s important to create your marketing around things your prospect is already thinking about – they will then see your product as the natural solution for whatever problem they are facing.

Speaking of problems, a big mistake I often see newbies in business make is trying to sell, “prevention.” There is an old adage in marketing that people will not buy prevention unless it is for their children. They only buy once they have a problem that needs to be solved. For example, if I tried to sell you an umbrella right now, it would be a hard sale – who wants to spend money on an umbrella? But if it was raining out I could sell you a fancy custom umbrella and you’d probably fork over double what it’s worth! Along the same lines, no one buys a burglar alarm until their’s or a neighbor’s house gets robbed.

People come up with all kinds of crazy ideas that violate this principle. I think that’s why none of these hangover remedies have been very successful. No one is going to stock up on that in advance, and when you do actually have a hangover, the last thing you want to do is leave the house!

So when you’re thinking about what market you want to enter, I suggest you find one that tackles areas where people have pain and urgency – an immediate problem they want to solve. Health, money, love… or something they are very passionate about, such as their pets or their hobbies. Create unique and valuable solutions to real, immediate problems and people will beat a path to your website!”

What is the best way to start building a quality network of people?

“One way that has been very effective for me is throwing dinner parties. Anyone can throw one, you don’t have to have a big budget. Find a friend who’s a good cook who is also interested in networking and invite all of the best people you both know that are interested in success.

They don’t have to be uber successful entrepreneurs, just get ten like-minded people in a room and exciting conversations will start. Then the next week have each friend invite a guest they feel can bring something to the table. That will get the ball rolling, and it will build from there.

There is a guy named David Gonzalez in Austin, Texas who started this thing called the “Internet marketing party.” David wasn’t crazy successful, he just started throwing this thing to get fellow marketers together every Wednesday night, and pretty soon he got twenty people going to this bar, which then turned into 50, and soon he was having bars beg him for business and top marketing gurus coming out to speak at the parties which were soon 200-300 people. It’s quite amazing what he did and this could be duplicated in any industry… or just keep things small and intimate. Either way, give it a name like the “Monday Marketing Mastermind” or whatever, and start doing it consistently. As the degrees of separation branch out, you’ll end up getting people in there who are high-level and great to learn from. Not to mention a group meeting like that, imagine where the people who started it are going to be five years down the road. Those who are started off as newbies, three to five years down the line, many have their own successful businesses and learn many valuable lessons to share along the way.”


Tell us what your passion is.

“My eventual goal is to spend all of my time helping people learn to live their passions and make money doing so. Right now I’m trying to build my own success so I can one day be a better teacher to others. I’m launching my blog soon,, where I’m going to begin posting tips on how to get in the position where you are carving your own life path and waking up with a smile on your face every day because you are free to focus on doing the things YOU want.”

You don’t consider yourself an “entrepreneur”, why is that?

“I’m a direct response copywriter by trade. When it comes down to business, honestly I’m not that good at much else. I’m bad with numbers, a terrible manager, and I can’t build a website to save my life. But what I’ve been fortunate to find are three great business partners who excel in the areas I suck at (read: everything but writing copy!). So a big message I want to get out there… is you don’t necessarily need to want to be a CEO to have your own successful business. Take whatever skills you’re best at and find people who complement you. So let’s say you’re not the CEO type but you have great marketing ideas or product ideas… then  find someone who is an executor to help you drive your vision. Find an operations person who knows how to get things started and partner with them or hire them. Let them do the nuts and bolts while you can be the creative visionary guy. Or vice versa, if you’re the type who is good at getting shit done, partner with an idea guy, then you run the machine and they tell it where to go.”


Tell us about your new reality show “Lucky Bastards” on Esquire Network.

“Lucky Bastards is about six guys living it up in Manhattan. It follows our business and personal lives, and it’s quite hilarious whether you are laughing at us or with us!  It’s totally unscripted and the conversations we have are just outrageous… it’s a real look into what goes on in the mind of men and it’s not always pretty!”

What is the craziest thing you’ve ever done?

“Hmm… tough to narrow down! I did the world’s highest bungee jump off the Macau Tower… many consider that to be crazy, and don’t get me wrong, it was fucking nuts! But I don’t consider that the craziest because no one has ever actually died doing it or anything like that. That ten second free fall will shake you up though! It’s 761 feet up this tower and you’re looking DOWN on the Wynn Casino. I was mentally prepping myself for two months, but once you get up there you realize there’s no amount of prep that can keep you from being scared. So that was very intense.

What are your thoughts about entrepreneurs being in relationships?

“I heard a story about a recent conference where they had the most self-made billionaires ever together in one room. Someone posed the question, “What is the most important thing that you would say it takes to become a billionaire? What do you all have in common?” After a short debate, they all came to a unanimous agreement: The one thing most responsible for their success was having a great partner. It wasn’t setting goals, or time management, or being in the right industry. All of those things helped too of course but they all agreed… having a great, long term partner was critical to their success. So I think if you’re wanting to build a business, absolutely a relationship is a way to go because one, you’ve got someone there to support you… And two… Speaking as a man, it takes your mind off trying to get laid all fucking day long! Which can get you very distracted from your business!”

Do you have any advice for any young success seekers out there?

“We are living in an age right now where you have more opportunity to make money with your passions than there has ever been before. There are opportunities to create businesses around so many different things. For instance let’s say you love being a photographer and you also want to make a million dollars a year. Well that was pretty hard back in the day, but these days with the internet you could start an online business that trains other photographers or you could start a company that sells cameras and equipment, and thanks to the internet you can do either of these without raising money or having any type of business experience whatsoever. I think we’re living in a unique time where you can make a lot of money following your passions, whatever they may be. So don’t think you have to settle for, “Oh I can do what I love but I’ll have to survive on thirty grand a year for the rest of my life”… that’s not true anymore. Hey, if 30k is what you need to be happy then more power to you, but thanks to the internet you are no longer limited. Google search something you love – see all of those websites? Many of them are making good money! It’s never been easier to do the same, so take advantage.”


Follow Craig on instagram @craigrclemens
Watch the first episode of Lucky Bastards on YouTube. The series airs every Wednesday at 10PM EST on Esquire Network
Photography by Daniel Nguyen
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