Get a Job: Essential Entrepreneurial Values You Gain from Having a Job

From the perspective of pretty much anyone who knows me personally or follows my social media profiles, the whole entrepreneurial thing has worked out pretty damn well for me. I lead a pretty the lavish existence; when I’m not working my own hours from a comfy home office or a gourmet coffee shop I have a super active social, dating and nightlife. I’ve already spent 60 days this year traveling and adventuring abroad and am planning another trip soon. No silver spoon here, this lifestyle is financed by my marketing and web development firm.

I’m part of a generation which increasingly believes that everyone should and can be an entrepreneur, that it’s as easy as reading a book, as coming up with a good idea, buying a domain name and heading down to your bank to form an LLC. Maybe I’m a just a crappy entrepreneur but I think it’s way, way more difficult than that. This blog will make the case that one of the most important steps to being an entrepreneur is to get a challenging job and working really hard.

Here is the brief, yet colorful history of my pre-entrepreneurial job experience. (I promise this isn’t just an exercise in narcissism, there’s a lot of useful lessons in here).

Grocery Store Courtesy Clerk

For 2 years in high school, I bagged groceries, cleaned public bathrooms and collected grocery carts from the parking lot during Colorado blizzards.


During the summers I served as a missionary twice on trips to an Indian reservation in Washington and a rural community in the dirty south of Arkansas. During these trips a disproportionally small amount of time was actually spent proselytizing, my days were filled with activities like painting old lady’s houses, fixing up community centers, putting on drama productions and helping out around schools.

Waiter, Buser, Cook & Dishwasher

In high school, I took a culinary class where we ran an actual small restaurant. During my senior year, I also worked in the ‘front of the house’ at a couple of restaurants and had many moments which you see in the ridiculous, comedy, satire film about of the hospitality industry, Waiting.

Car Salesman

With mediocre grades, zero college savings and a broke down old Porsche that I still owed $3000 on upon graduating high school, I decided the best course of action would be to take on one of the most intimidating jobs in America. Somehow with my youthful exuberance and clip-on tie, I talked the sales manager of a Hyundai dealership into giving me a job. I spent about a year in the industry and ended up selling at one of the highest producing Toyota dealerships in the country.

Door to Door Outside Salesperson

I also spent a couple of hard months walking miles a day (while wearing a suit!) knocking doors. This was a 100% commission gig so rain, snow or searing heat I would do my damnedest to sell bored strangers a $60 golf or spa package gift card.

Telephone Marketer & Mortgage Broker

I started as a cold calling telephone marketer and after becoming proficient at generating 1–2 hot refinance or purchase leads an hour I was promoted to mortgage banker. This was during the mid-2000s refinance boom times so it didn’t take long for me to go from a lowly telemarketer to structuring million-dollar finance deals and negotiating sophisticated relationships with real estate brokerages.

Personal and Business Banker

Around my 21st birthday, I decided to trade the feast or famine insanity of the finance brokerage world for some corporate security and became one of the youngest bankers ever hired by US Bank. My days were filled with account opening procedures, structuring loans for small businesses and trying to persuade my branch manager to forgive the ridiculous overdraft fees that bank customers accrued. The most exciting part of being a banker was the day we got robbed.

Corporate Advertising Account Executive

I spent 2 years working for a surprisingly good employer, Dex Media, managing the advertising accounts of small and not so small businesses.

Marketing Executive of Entertainment Company

Someone looking at my list of ever-demanding jobs might think I traded the awesome experience of college to be a workaholic. Nothing could be further from the truth during this time I had a ridiculous social life that kept me out past midnight 3–5 nights out of the week. I eventually parlayed my social network, sales skills, and marketing savvy into a position at a start-up entertainment production company. Planning events at the Denver Broncos football stadium, pitching sponsors, negotiating with venue owners, coordinating gorilla marketing campaigns, drafting contracts with bands and preparing lots of proposals. What wasn’t in my job description was dealing with the ridiculous antics of the company’s cocaine-addicted CEO and a highly emotional. deep-pocketed investor, financing the company who was (I can’t make this up!) also a clinically diagnosed multiple personality dissociative.

Lessons this entrepreneur learned from the jobs above:

Develop real skillsets.

There is a myth of dubious veracity that entrepreneurs don’t need actual skill sets. It goes something like this; an entrepreneur comes up with a really good idea, entrepreneur raises capital because they are passionate and have a really good idea then entrepreneur hires people who are smarter or more skilled than themselves to make the good idea happen. Many popular business books and media focusing on entrepreneurship, in many more words than the sentence above, spread this message citing examples of highly publicized entrepreneurs who luckily found themselves at the intersection market demand, technological innovation, and economic conditions. In the real world entrepreneurs need at least the following skill sets:

A technical or trade skill set — This is a skill set that is essential to the product or service that the business gets paid for. For example the computer programmer who creates a killer app that is the foundation of a tech startup, the skilled chef who’s culinary masterpieces attract customers to a restaurant, the scientist that creates a supplement that makes people healthier, the dentist operating their own practice, the engineer that creates a useful widget that makes people’s lives easier or just ask yourself how many bar owners have you ever met that DO NOT KNOW how to bartend?

Sales — Your product or service is most likely not going to sell itself and even if it does you are going to do a far superior job of selling it. The most direct path to increased revenues is almost always a flesh and blood person prospecting daily, doing needs analysis with potential customers, making pitches or proposals, overcoming objections standing in the way of the transaction and asking the prospect to buy. Until your company is large enough to hire and train a sales force that person should be you.

Marketing — Whether it’s video, word of mouth, print media campaigns, gorilla marketing, really great ad copywriting, or one of the myriad forms of online marketing you should be intimately familiar with at least one effective way to make your target customers aware of you what you have to sell.

Content Creation — An increasingly effective way of demonstrating that you know your stuff when it comes to your business is to create content about what you do in the form of written articles, videos, audio podcast programs or graphics. While some of the technical sides of content creation and syndication can be outsourced any entrepreneur should be prepared to spend some long nights pounding away at the keyboard generating free content that is helpful to their prospective customers. The two primary websites ( and I have for my businesses each have at least 50 unique articles and a dozen videos I’ve produced.

Accounting and Legal — Once the above skill sets actually make you some money, you need to start worrying about how much of it goes back into the business, how much of it goes back to you for working so damn hard and how much of must be rendered unto Caesar. While there are plenty of accountants and attorneys who will gladly help you figure this all out for +$100 an hour, my experience has been that unless you have a particularly exotic business model, reading a few books on accounting or corporation formation, lots of Google searching and occasionally getting a free 30 minute consultation from an attorney will get you by just fine in the accounting and legal department.

Going back to the theme of this article, the trade or technical skillset as well as the marketing and sales skill sets are almost always better to acquire while working in a job than while in the middle of starting your business. Your business doesn’t start when you incorporate, build your website or order your business cards, your starts when you make your first buck. If learning a technical skill so you can provide a service, learning to manage your own marketing campaign or being able to convince people that your product is the best stands in between incorporation and profitability, your chances of succeeding in your endeavor decrease. Those who see themselves one day as entrepreneurs should look for jobs that will teach them these essential three skill sets.

Tip: 100% commission jobs or gigs get a lot of grief, but they are unmatched as an environment wherein you will be aggressively coached and learn the sales and marketing skill sets, fast.

Do it because it is hard.

Entrepreneurs are consumed with a desire to find the path of least resistance and that’s a part of the reason why they change the world. Of course, it is more important to work smart than to work hard, but hard work is still pretty damn important to making things happen in business. While it’s certainly not the most efficient way to make a sale, walking 5 miles in a day, asking +200 strangers to buy your product builds a hell of a work ethic. When I started my own firm, my first few clients I acquired the exact same way, knocking doors. The point is that you have to get out your comfort zone to get places in life or business. Unless you are an exceptionally bold person naturally you are going to need some kind of mechanism to get you in the pattern of venturing beyond your comfort zone. While entrepreneurs are some of the hardest working and most committed people on earth, they often look for ways to circumnavigate their challenges when should be beating them to a pulp with a rusty crowbar.

Mindset life hack: ‘eat a frog’ every day, the classic sales and personal development guru Brian Tracey, created this strikingly disgusting metaphor. The very thought of eating a raw, live frog should give you a sensation of unpleasant disgust and fear deep in your stomach, it might even make your hair stand up. Now think about what there is on your to-do list for your business that you are avoiding because the thought of it is so unpleasant (although maybe not to the same extent as eating a slimy green, ribbiting reptile). Do that thing now. It might be a confrontational phone call, standing up for yourself, addressing a problem with your partner, firing an employee, collecting on an invoice, paying taxes, fixing a bug in your software or saying no to an unreasonable request. It won’t be easy but chances are that its bark (or ribbit?) is far worse than its bite, the anticipation of doing that hard thing is ultimately far more painful than the act itself. This is an amazing stress relief also.

The importance of first impressions, looking good and curb appeal.

A frequent mistake made by entrepreneurs is that we try to sell our products and services to Vulcans (The Star Trek aliens who make all decisions by logic alone, devoid of emotion), so to speak. We forget that our customers are human and that the hot cognition emotional triggers of sexy aesthetics, packaging, cleanliness, scarcity, and novelty are far more effective at impulsing buying decisions than feature-benefit charts and competitive pricing. Over the years I learned the chief importance of aesthetics and first impressions when it came to the things I was selling, whether it was my religion to a troubled kid whose school I was helping clean up, a pricey meal, a shiny new truck or a mortgage for a beautiful house.

Be very wary of taking investors money.

The siren song of investment capital tempts all entrepreneurs. The fact of the matter is that investment capital can actually be a real bain to entrepreneurs; entrepreneurs that operate on a shoestring, bootstrapped budget run their companies leaner and smarter than those who can afford to make mistakes because of cash backing, if venture or angel-backed companies do survive their first couple of years it often results in the company operating while constantly in debt and paying interest. A lot of entrepreneurs who accept investment capital or bring on a board of shareholders actually end up having a boss who ultimately has more power than the entrepreneur, think about Steve Jobs being fired from Apple, the company he founded.

Understanding and identifying with the vast majority of the people in the world.

I know a couple of entrepreneurs who have had the good fortune of ‘never having a real job’, while the creativity, intelligence and ability to recognize and capitalize on opportunity that these people have is certainly impressive they are generally douchebags in one way or another. As someone who has in the past 10 years had jobs ranging from basically untrained labor to sophisticated corporate sales, marketing, and management roles it’s pretty hard for me to meet someone who’s career experience I can’t relate to or empathize with.

The supreme importance of creating autonomous profitable systems.

Throughout my entrepreneurial career, I’ve had some very disheartening moments where I was flat broke or working ridiculously hard for an embarrassingly small amount of money. Contrast this to my stint in corporate America, where I was always handsomely compensated for my time. I was part of a system, a very profitable system that made money autonomously of how hard or smart I worked on one day or another. This reality serves as a constant reminder that the ultimate job of an entrepreneur is to create and improve autonomous profitable systems that make money.

Originally published at

Adventuring philosopher, Pompous pontificator, Writer, K-Selected Biohacker, Tantric husband, Raconteur & Smart Drug Dealer 🇺🇸

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