The Entrepreneur’s Checklist


Friday, 2:15pm
Reno, NV
I read the news today, oh boy…” (John Lennon, “A Day In The Life”)


One of my favorite quotes from the legendary Gary Halbert: “There is nothing that cannot be accomplished by a man who refuses to face reality.”

You laugh, but he was dead serious. One of the reasons we became fast friends was our mutual outlook on life – whenever reality was inconvenient to our goals, we just ignored the facts, lowered our head, and bulled forward.

That photo, above, is me in high school (from the yearbook), taking a jump shot. I’m the guy in the thick glasses. I loved basketball, and was good enough to become the captain of the “B” squad my junior year…

… however, as should be evident in this photo, I ran into a brick wall trying out for the varsity a year later.

The guy guarding me as I took that jumper is taller than me by a foot. I was the smallest guy on the squad…

… and really, at some point a caring coach probably should have taken me aside and said “John, I know you love the game… but look at your family. No one is taller than 5’10”, and basketball is a sport for tall folks. You’re not going to magically grow into the size they want on the varsity team…

I wouldn’t have listened, anyway. I’m like a Jack Russell terrier – a big dog trapped in a small dog’s body. Tell me I can’t do something, and you get a prolonged snarl (and maybe a quick nip).

Eventually, in sports, my poor eyesight and lack of height stopped me…

… but I had fun for a couple of years in the meantime.

Later on, as I was gathering my courage to try copywriting, an actual professional copywriter earnestly informed me that I should not even try.

“It’s too hard,” she said. “You’ll never be a pro writer.”

That was, of course, the BEST thing she could have ever told me. I doubt I could have survived the first years without that internal motivation of needing to prove her wrong. It fueled me during the tough early years.

I call it “negative motivation”… and it’s actually one of the most powerful forces available for getting stuff done. I never saw that writer again, and don’t even remember her name…

… so it wasn’t a need to flaunt my success in her face. It was all internal for me – I used her as the “face” of the obstacles in front of me, and I even laughed when I later realized I was in a position to tell her “Fuck you, I made it anyway.

Yes, my internal ego is an immature twerp sometimes. Chip on the shoulder, testy underdog attitude, and an almost stupidly-aggressive and irrational refusal to face reality.

I am so grateful for it, too.

(By the way… I nailed that shot in the photo, above… and ended up with 20 points while also hitting the winning basket. Easily my finest moment in a futile, doomed effort to be a “real” basketball player. A has-been at 16.)

Now, you do not need to be a belligerent rebel to be a good entrepreneur…

… but it can help sometimes.

Certainly, given the choice of sitting down to dinner with the business types in suits, who are uber-polite and careful in their conversations…

… or the rowdy crowd of rule-breaking ne’er-do-well whack-job entrepreneurs who may easily get kicked OUT of the restaurant….

… well, you know which group I’d pick.

I was Halbert’s sidekick for a very long time, and one of the most enjoyable parts of the gig was strutting into a new client’s offices and creating massive chaos. In a rational world, none of the buttoned-up biz owners we dealt with would have tolerated us for more than a few minutes…

… but, because we brought the “magic” of ads that worked, they HAD to not just tolerate us, but sometimes coddle us and even pay us more than they were going to earn themselves in the project.

We weren’t mean. Perhaps arrogant at times. But both Gary and I had wandered into the entrepreneurial world precisely because we didn’t “fit” in the normal corporate environments. We were outlaws by nature, outrageous by temperament, and adventurers who ate risk for breakfast by choice.

Again – you do not NEED to be a half-crazed rebellious lunkhead to succeed in biz…

… though, I’ve noticed that a great number of the dudes and dudettes at the top of the entrepreneurial game don’t easily fit into nice, tidy molds. They don’t behave themselves in polite company. (Y’all know who you are.)

So I’ve been thinking a lot, lately, about what you DO need to be a successful entrepreneur. In my mastermind, there have been many members who were unclear on what it “meant” to be an entrepreneur…

… and we’ve helped every one of them get over their fears, stop obsessing on the wrong things, and become much more confident (and successful) marketers. Mostly, they are stunned by the magnitude of profit that comes from doing things right.

It’s all a matter of hanging out with veterans who can commiserate with your stumbles, help you correct the damage, and reveal the secrets of getting into a solid success-groove, and riding it all the way to wealth and happiness.

My goal is to, eventually, have a comprehensive menu of things you can do at every step of your business life. That’s gonna take a while, though…

… so, for now, I have a starter checklist here you might find helpful.

Let’s just get into it. Here (in no particular order) are the main things you’ll need in your “toolkit” as an entrepreneur:

[] Survival resources. This includes books (both the ones you read for general knowledge and put on your shelf… and the ones that stay on your desk, dog-eared, because they are tools that help in your day-to-day work)…

… an ever-expanding network of experts, mentors, colleagues and go-to-guys (including tech geeks, hosting services, spies, friendly competitors, and helpmates in your quest for animal-level contentment)…

… and whatever courses, seminars, and tutorials you need to attain a mastery of the details of whatever biz you’re in.

[] Goal-setting skills. You need to understand, clearly, where you’re headed and what you want from both your journey and your final destination.

It’s okay, early on, to not be clear on you ultimate goals. Sometimes, you work hard to attain something, and only then realize it wasn’t what you wanted after all. That’s how life works when you decide to swim in the dangerous part of the pool. You will constantly re-adjust your long-term goals as you go.

Short-term, however, you need to get good at breaking down the best path to your target, while also learning how to fix problems and deal with unexpected emergencies.

[] Thick skin. You simply need to put your ego aside when entering the entrepreneurial world…

… cuz you’re gonna get stomped, bullied, abused, insulted and assaulted. Often. In new and fascinating ways that your civilian pals will never believe possible.

Your motto must be “eyes on the prize”, at all times. There will be setbacks, disasters and breathtaking failures.

You know you’ve “arrived” as a true entrepreneur when all of this becomes just part of the process, and you even enjoy the constant challenges raining down on you. (You’ll have the best stories at the bar during seminars, too.)

[] Risk tolerance. This is what sets most entrepreneurs apart from civilians. Against the advice of your drinking buddies (who really do not want you to succeed, because that will destroy their own belief that the little guy can’t win)… and contrary to the fears of your family (who are terrified that your wild-ass biz plans will bankrupt the joint)… and in utter defiance of your own Red Flag danger alarms…

… you’re going to have to lay your reputation on the line, and climb into a fight with the forces of capitalism armed only with your wit, meager skill sets, and raw determination.

And no one else except other entrepreneurs will even vaguely understand what you’re going through. Working without a net. Daring the universe to slap you down. Going into situations, over and over again, where you’re a complete rookie, apt to make embarrassing mistakes.

In short, living with risk. And the consequences of risk, which can include failure.

Of course, a true entrepreneur regards “failure” as just another step on the rocky path to breakthrough success. It’s a process. Few get it right the first time.

So, you need to assess your capacity to accept, and deal with risk. If the very notion of taking a risk terrifies you into inaction, it’s probably a sign from God that you need to get a job somewhere safe.

[] Your basic bag of tricks. You may have to learn the basics from books at first, or by observation… but no matter how you learn them, you need to understand the fundamentals of a sales funnel (qualified leads are captured and closed)…

… the details of fulfillment and customer management…

… and how to craft a sales message that can be easily communicated to prospects.

It’s not rocket science, but you’re an idiot if you think you can “fake it” as you begin marketing your biz for real.

Fortunately, there are a lot of courses out there to shortcut your efforts…

… or, you can dive into the many books out there on these subjects. In a weekend, you can begin your self-education by reading one on marketing, one on sales, and one on writing copy.

Your first choices may be the wrong ones to read, but that doesn’t matter — because you’ll have started the process, and that’s the critical part of this step. Next weekend, read three different books on the same subjects. Rinse and repeat until you feel you have a toe-hold in each subject, at least.

The longest journey begins with a single step. Just try not to fall on your face immediately, all right? Read critically and intelligently, and continually seek out authors you can trust and identify with.

[] A budget, or war chest. You will need cash in your biz adventures. No getting around that.

I’m not a great role model. I started my freelance career with one last tank of gas in a rattle-trap car, one month’s rent paid, and enough spare change to feed myself for a couple of weeks. I had no Plan B.

Much better to have a planned budget, and the money to meet it for at least a few months. If you’re already in business, and you want to expand or get into a new project…

… then have a “war chest” of cash you can invest in the adventure. Don’t go in broke, or clueless about what you may need to pull out of your existing biz.

Most entrepreneurs hate budgets and planning.

Do it anyway. There are plenty of misadventures awaiting you in biz — don’t stumble on stuff like budgets, which you have control over and can figure out easily.

[] Ability to judge what’s worth doing, and what’s going to hold you back.

This is a biggie. You may suck at it right now, but one of your goals must be to get pro-level good at judging client requests, job offers, new projects, partner assessment (in both biz and love), and all the little and big decisions that will cascade upon your head every single day.

One tactic: Use the 1-10 “pain scale” measurement many doctors use in assessing patients. Use it on yourself: What level is the value… the risk… the reward… and the danger of any decision you encounter?

Is it a big deal, or a little deal of no lasting consequence?

Get good at this, as fast as possible. One of the main failure points of unsuccessful biz owners is a lack of prompt, good decisions.

[] Stress management. You’re going to encounter stress as an entrepreneur. That’s a given.

Ignoring this stress is a very, very, very bad idea. It will never leave, it will build up, and in due time it will fry your brain like an egg in a skillet.

You are not a superman. Your body and mind are vulnerable to the ravages of poor diet, lack of exercise, and constant hormone dumps of adrenaline and other bad chemicals.

Massage, meditation, lots of vacations, reading good books (not biz books) to relax, having “safety zones” in your week where you are free from the tentacles of your biz (no phone, no email, no nothing)…

… the tactics for battling stress are easy to find and experiment with. Find what works for you, and give it PRIORITY status in your life.

For example, I began getting weekly massages early in my career… long before I started buying better clothes, a newer car, or eating out more often. Massage “re-set” my physical stress levels, and I’m convinced it has saved me from ulcers and worse. And kept me mega-productive for decades.

I started out with a “business before pleasure” mindset… but included in “business” was de-stressing and being a good animal (loose, strong, well-fed, lots of restorative sleep, etc).

And finally (for this short “starter list”)…

[] Have an exit plan. Go after your goals like a terrier after a squirrel, with total focus and commitment.

However, realize that sometimes your goals need to adjusted, or even abandoned.

When the facts and circumstances change, your goals change. (This includes sudden changes in technology, like Google slaps… booming new opportunities that didn’t exist earlier… even realizing you no longer crave what motivated you so desperately before.)

I’m not suggesting you have an easy “bail out” plan, that you can take whenever things get dicey. Like Cortez burning his ships upon his conquest of Mexico, a lot of entrepreneurs do better when there is no turning back.

Rather, I’m talking about visualizing your life after success. Many entrepreneurs, right after “making it”, immediately begin to sabotage the biz. Because the fun is in the building up of the thing, the adventures of tackling challenges and working without a net.

Once you’ve been successful, you either need to pivot to management of the biz (yawn)…

… or consider the consequences of cashing out, selling your biz, moving into something else, or just becoming an “intrapreneur” like Steve Jobs did at Apple.

At least consider what your life will be like when you succeed. And consider lots of options for yourself.

Okay. That’s the starter list. Not a bad checklist to have on the wall above your desk as you move forward, either.

One last thought on reality: Yes, I ignored the reality of who I was, and what I brought to the game, as I plowed through life going after unrealistic goals.

However, there is ONE reality I never ignore.

That would be the reality of results. I love seeing how ads and tactics work, or don’t work, through actual sales numbers (and click-through and open rates, and so on).

However, I look at these results CRITICALLY. I don’t accept them blindly. They are tools for moving forward. Where did, or where could the ad have failed? Can we fix it? What other things can be done to navigate a sales problem? Where IS the main problem, anyway?

My stupidly-aggressive and irrational refusal to face certain realities has served me well over the years. If I’d listened to the nay-sayers, or even my own fears, my life would have been much less exciting and happy. And rich, in every respect.

Still, all vices in moderation. That’s my motto.

Find out what works for you.

I hope this list is a good starting point.

Stay frosty,


P.S. Did I leave anything off the list that should have been on there?

Love to hear your take on the matter, in the comments section below…

P.P.S. Need a good suggestion for a book to jump-start your quest for the Big Bucks?

Start right here on the blog, in the far right column. Grab “The Entrepreneur’s Guide To Getting Your Shit Together” right now on Amazon. Or order “Success Secrets No One Told You About”, also available digitally (and it costs just a couple of bucks).

And when you’re ready to join the best mastermind operating, check out the Platinum Mastermind. I’ve personally been hosting this notorious group for over 8 years now.

Don’t be that guy who refuses to help himself, with opportunity staring you in the face. I’ve been transforming the lives of entrepreneurs for over 30 years now… to conquer obstacles, earn massive success, and start enjoying life on all levels…

… and the FASTEST way to make it real for YOU, is to take advantage of the help I offer.

You’ll figure everything out so much faster (and with so much less grief) when you get some honest mentoring from a grizzled pro who knows his shit.

Again — love to hear from you in the comments. I hang out there often…

20 Responses to The Entrepreneur’s Checklist

  1. I enjoy and relate to about everything you write. We are about the same age, lived through similar situations, and played basketball as a “shorty”.

    This will be printed and cut out, cut up, and arranged in the order I like. Stuck on the wall for reference, and then start my “new” business.

    Thank-you for your valuable insights and unforgettable sayings/quotes/words that make me smile and say holy shit, I get it!

  2. I rellay enjoy now tell me why even if realy has never stopped me I am not as successul as you are maybe because I have a PJR and not a JR? Really great thank you (sorry for mistakes writing from Italy)

    • Naw, I think all Jack Russells have the same ornery streaks. Keep after your dreams. There are lots of other posts here in the blog concerning implementing plans and achieving goals. Keep searching…

  3. Every time I come here I leave with John’s boot-print on my ass.

    But also with a smile on my face and a better understanding of what I’m doing.

    It’s priceless, really. See you next month,


  4. John,

    You hit the nail on the head with this post.

    From setting goals and taking risks.

    I know when I start a new campaign I have doubts and we always have that person in are lives that’s the “…oh that will never work” person.

    And if we didn’t do things that were a little scary we’d always be thinking… what if?

    Bill Jeffels

    P.S. Always love the old Gary Halbert stories

    • Those lingering “what if” questions can haunt your life. I faced up to them when I hit my early 30s, best move I made. There are always regrets, but mine are of mistakes made, not mistakes never attempted.

  5. Many thanks, for always providing inspiration and common-sense strategies.

    I purchased Kick Ass Copywriting and have been hooked since.

    With your help, I have decided to start my own business.

    I can’t thank you enough and look forward to joining the Platinum Mastermind group next year.

    Again, many thanks.

  6. Awesome post John. Excellent starter checklist. I love reading your posts. Their fun to read and I often get jolts of awakening in mind reading them. I appreciate those moments. Thank you.

  7. Great post and so true. I love what you said about “Thick skin”, being an entrepreneur is not for the faint of heart and not for sissys either. Everybody including your spouse, parents, siblings and close friends would say this is wrong and dangerous. But you just gotta test, try and get ahead.

  8. CRUNCH! Joe, the tallest bully on our block broke my nose with a left forearm, and that was it for me and basketball. I was 10, a fat shrimp, with glasses, and suddenly a broken nose. So I left basketball behind and started selling the next day. Literally. I sold M&Ms, and later software, now I help non-profits but somewhere I became tamed. I was tamed by big bullies who like Joe wanted the game all to themselves and I became stuck. Your blog is like Joe’s left forearm shattering forcing me to make a decision . So, I guess I will walk away from being dignified and get back to selling.
    Thanks for inspiring!

    • Sorry about the nose, but glad it worked out. I’ve tried, as an adult, to level with the kids in my life (nephews, great-nephews and -nieces, kids of friends, and the occasional class I teach), and BE that Bad Uncle who tells the truth. I wish I’d had one in my life — sure woulda shortcut some of my more painful journeys…

        • It’s funny, but I set out, early in my career, to be “that” uncle to the many writers and marketers needing some sage advice (which I just happened to have handy). We all need a truth-teller in our lives, especially one who’s been around the block a few times…

  9. John,
    The truth is nothing is so motivating as proving someone wrong about you. Many times in my life stubbornness and persistence in figuring something out got me through.
    The secret seems to be getting out of your own way, being honest, taking feedback, trying again, and ignoring your doubters. Learned from my failures, and forgave myself too. Became a writer by writing ugly, and then editing, fixing and clarifying the point one more time.
    Good advice and keep sharing. Thanks again.

  10. I think balance is key when pursuing your own biz. My life is a little different in that I still have my day job, but have tons of flexibility at nights and on the weekend. That’s where I work on my biz. At the moment, I’m working on my biz, but also have outside hobbies that require lots of work…golf and tennis. So I completely walk away from my biz when doing those things (unless a light bulb goes off on 16 when I’m walking to my ball…then I’ll jot it down for sure.) Most of the times, I can come back to my biz feeling fresh. All three pursuits (biz, golf and tennis) are a grind. I’m finding that time goes by too quickly… So instead of hoping it to be three months from now when X, Y, Z will be finished, I’m just trying to focus on today. I’m 34 now, but will be 70 before I know it… The key I’m finding is to do work on each every day. You don’t need to look at it as daunting. A fellow lacrosse coach once told me, “I always earn my beers.” This guy was in freakish shape…The guy was in his mid-fifties and always got his workouts in. And, sure enough, each night he would be drinking his Buds. I’ve incorporated the same concept into my pursuits. Although, I don’t drink Buds every night, I definitely have some on the weekends. Doing the work each day of the week and during the day on the weekends allows me to really enjoy those…

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