contents · 5 dumbass mistakes (otherwise smart) entrepreneurs make 3 to my fellow entrepreneurs,...

5 Dumbass Mistakes (Otherwise Smart) Entrepreneurs Make

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www.JayRookeCoaching.com

Contents

1. They have a pre-conceived notion of what running a business “should” look like ............... 4

2. They don’t get that it actually is their first rodeo (but everybody else does) ....................... 7

3. They’re trying to play the field, but they need to settle down ................................................ 10

4. They let their inner-critic replace them on the org chart ......................................................... 13

5. They don’t get the support they need and try to do it all themselves .................................. 15

Author’s Bio:

A member of Forbes Coaches Council, Jay Rooke, J.D. is a trained executive and business coach who resides in wine country in Sonoma, California. In addition to 1x1 coaching, he facilitates Mastermind Groups for kick-ass business leaders and entrepreneurs.

Jay also runs a podcast titled Know Pain, Know Gain, where he interviews successful entrepreneurs; and he serves as a Startup Grind Chapter Director.

A former attorney for the City of New York, Jay later spent a decade in corporate, working for big companies like Merck pharmaceuticals and NBC Sports, down to small startups, as well as owning his own restaurant.

Jay is the Co-Founder of GivingKicks.com, a charitable initiative to provide 1,000 shoes to 1,000 underprivileged kids when they go back to school. He is a member of Rotary, and sits on the Board of Directors of the Sonoma Boys and Girls Club.

http://www.jayrookecoaching.com/


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To My Fellow Entrepreneurs,

I'm fortunate enough to work with really bright clients, but like any cohort, they seem to run into common challenges and pitfalls, oft-repeated by their peers.

Pay attention to anything long enough and you'll start to see patterns. Once you start tracking patterns, you can start to draw insights.

What are the biggest mistakes that I see the majority of my clients make, and what are the techniques to steer clear of those pitfalls? These are the questions I've tried to answer in this playful, but cautionary e-book to serve you as you navigate your entrepreneurial journey.

I salute you and wish the best--you guys are my heroes, BUT DON’T BE A MARTYR AND TRY AND DO THIS ALL ON YOUR OWN!!! I invite you to consider joining our tribe of talented and crazy black sheep and entrepreneurs at www.JayRookeCoaching.com, and roll with a community who knows exactly who you are.

And remember: if you’re not the lead dog, the view never changes.

Warmly,

Jay




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1. They have a pre-conceived notion of what running a business “should” look like—and then they run it

that way.

isten, I was raised by nuns, I know all about how things “should” and “ought to be” done. But there’re two types of people in the world: those who know how to run a business and have done it, and everyone else.

Here’s the problem: there’s only one “should” that the business should adhere to—that the business should make money. Everything else is pretty much up for grabs. Unless you want to “play” business, this is the only rule that matters and you need to get your head around it quickly.

A lot of high achievers were historically trained to equate success with doing everything that is asked of you and doing it well. Unless you have funding to burn, I can almost guarantee you that that mentality will wash you out of the game quickly.

L



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If you want your business to succeed you need to quickly accept the fact that you cannot please everybody all of the time, and that exceeding everyone’s expectations in every realm is a game of diminishing returns.

So…if you got 4.0’s in school and participated in a ton of extracurriculars, this is where you need to take a lesson from that dude who missed 50% of the classes, studied hard the night before the exam, got a C, and ended up with the same degree you did. Pretty is as pretty does. Conquering to-do lists and responding to all those emails and saying yes to all those requests for help does NOT make you a go-getter in the entrepreneurial world—it makes you a dumbass.

Get clarity around what value you have at your most specific core, figure out how to make money at it, and pursue that myopically until you get your business to a level that it’s making real money (whatever that means to you). Once you get there, you’re free to re-evaluate, tweak and re-engineer, but here’s the big difference, when you do re-evaluate, tweak and re-engineer, you’ll be doing it as a VIABLE business.

And I don’t want to hear it from any of you heart-based businesses and B-Corp ballers—you are passionate about what you do and you have a soul mission that drives you every day. I get it—in the words of Macklemore, “If I did it for the money I would have [stayed] a fucking lawyer.” Perhaps dissonance is driving you away from the corporate route and you want to make a go of it. I applaud you and want to support you. But here’s the deal: until you have a viable business that is literally profitable, you don’t have shit.

And I’m not being overly capitalistic here. If your business folds, then whatever your big-picture mission was folds with it. All that good you thought you were going to do turns into literally zero impact. Your #1 focus needs to be to make the business viable—just because you don’t give away 10% of your profits in your first year doesn’t make you bad people—just amortize that forward. What’s your collective positive impact if you stay open for 20 years and scale? That’s where to keep your eye on the prize. You’re lying to yourself otherwise. Outsmart the game, don’t try to beat it—I’m all for the fight, but don’t be a kamikaze your first time out.

This mindset change can be an awkward growth phase for the employee-turned-entrepreneur. For example, as an employee, maybe you should respond to every e-mail you got, but as an entrepreneur, you will need to learn how to actively ignore many of the demands that are placed on your time, especially when they draw you away from revenue-generating activities.



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When we fixate around the concept of “should,” by definition we deviate from focusing on what’s “necessary.” No bueno. The energy of “should” also invites judgment; eg, “if I complete my to-do list, I have value, and if I didn’t finish it, then I’m not a good person.” When we do things based on “should,” we don’t enlist our own creativity, nor do we structure a business based around our strengths. In the should model, we unconsciously adopt someone else’s perspectives of the business world, irrespective of whether or not we actually hold those principles true. Worse yet, we adopt a business model that was meant for someone else.

Takeaways: 1. Don’t get caught up in the game of appearances or dogma. Map out specifically

how the business makes money and revisit it monthly. Whatever your answer is, structure all activities in support of this initiative.

2. When we operate in the world of “should,” we narrow down the ways in which success can occur. Here’s a newsflash: ESPECIALLY during your first few years, NOTHING goes as it should. If you adopt a “should mentality” you’re going to eviscerate your self-confidence and your ability to lead your organization because you will always be thinking that things are going wrong because you’re not achieving your “shoulds.” Instead, move your measure of success to evaluating how well you navigate your challenges. When we operate from a constantly renegotiated perspective of “what is possible from here?” we enlist all our creativity and resources, and have the awareness to identify and capitalize on opportunities. And let’s be honest—running a business from the other mindset is fucking misery—for you and everyone included. Get crazy—throw predictable to the wind from time to time—have some fun—you did this to be happier, didn’t you?

3. If you’re coming from the corporate world, you most likely operated within some level of structure. On its best day, your first year is going to be a three ring circus shit show. Chaos will rule. Make peace with that. As the saying goes, let go or get dragged behind. You can’t operate at an A+ level across all disciplines. Choose the 1-2 areas that you need to perform at an A+ level, and identify the areas where you can coast at B-. Conserve your resources, young buck—you’ve got a long race ahead of you. Impact is much more important than achievement.



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2. They don’t get that it actually is their first rodeo (but everybody else does)

In many disturbing ways, entrepreneurship bears resemblance to having children—it destroys your finances and your social life, encourages weight gain and takes years off of your life from stress and worry. But I digress….

IMO, the notable way in which entrepreneurship impacts us like having children is that if you’ve got a notable flaw/blindspot, or haven’t worked out some long overdue shit you’ve been avoiding, that issue almost always get intensified once you have kids. Entrepreneurship is the same way—trust me.

Scared of failing? Risk averse? Have issues around confrontation? Have a challenging relationship with money and debt? Engage in any unhealthy coping mechanisms? Ever get absurdly hard on yourself? If you said yes to any of these, you’re in for a treat.



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Entrepreneurship is a wicked mistress, and she knows exactly how to push. All. Your. Buttons.

Remember the first time you transitioned from student to employee? And then from employee to manager? Remember how radically different it all became each time you made a shift up? More importantly, once you had the benefit of retrospect, could you see how nothing could have prepared you for the experience, other than the experience itself? Launching a business represents a similar leap, with the punishing difference that there’s zero room for error in the learning curve, and you don’t have a built-in support team in place. So, yeah. Have fun with that, right?

Here’s the deal: don’t view running your own business as a linear progression from your previous step. It might look that way on your 5-year plan, but you won’t experience it that way. Remember “practicing” for your first sexual experience, and then what it was actually like? Do I need to say any more?

So, you may ask, how do I successfully navigate an experience that I can’t really prepare for? I have no fucking clue.

But I’ve got decent guess:

Recognize that deliberately or not, you are shaping your voice and style of leadership. My suggestion? Do it deliberately. Otherwise, you’ll probably be a mess. Seriously.

Here’s how to be deliberate about cultivating your leadership style:

1. You need to up your self-awareness. My two fastest ways to craft your true leadership essence: meditation and enlisting an objective, external resource to serve as your confident, consigliere, Sherpa, counsel, caddie, rabbi, etc. (this might be a peer, a coach, a mastermind group, whatever—bottom line: someone that doesn’t have any agenda, wants to see you succeed greatly and has zero incentive to be anything but 100% honest.

2. You can’t put together good recipes if you don’t know your ingredients—learn about yourself: Take the BOSI assessment, check out SuccessDNA, Myers-Briggs, the Enneagram, etc.


http://bosi.in/Vjndk


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3. Make personal growth part of your DNA as a leader. Yeah, you probably “can” get “there” on your own, but the faster you get to “there,” the faster you can get to whatever is next. Invest in your growth. You wouldn’t hire employees or lock arms with partners if they never evolved, so how can you lead if you don’t set the example?

4. Corporate culture matters. If you don’t believe me, remember how shitty life was when you worked some place toxic? Even solopreneurs’ businesses have corporate cultures—it all starts with you. I highly encourage you to write down what your business’s values are, as well as your operating principles, and check in with them often as a reminder of what type of business you’ve chosen to be. When you observe a delta, don’t hate on yourself, just course correct.

You might notice that none of the actions listed in this article directly relate to the execution of the business. Which means that if you believe in the value these commitments will deliver, then you need to figure out how to work them into your way of doing business.



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3. They’re trying to play the field, but they need to settle down

If you’re early-stage, you’re probably still in the honeymoon phase of your launch where you’re wildly excited about your business and rather than narrowing down your target demographic, you keep seeing new opportunities for ways that prospects could use your project or service. And that’s a super fun time in life, but….

STOP IT. Seriously. Figure out who you love to serve, and commit to them.

Here’s why: unless you have Comcast’s marketing budget, you simply cannot be all things to all people.

Think about it from the perspective of prospect attraction and client conversion. Play with me here: pretend you’re a realtor and you’re in the market for a new website—I’ve got two questions.



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1. Who would your first call go to? The guy who builds websites for small businesses, or the guy who specializes in making websites for top-performing realtors?

2. And once you’re having that exploratory conversation with each website builder, which one makes you feel safer about your upcoming investment? The builder who asks what you want and then responds, “yeah, I’ve done something like that before,” or the one who says “I’ve worked with realtors who have been in your exact position, and I know certain tricks in your industry through my realtor referral team, and I can grow with you as you get to that next level of performance. I’ve worked with [insert 5 of the top 10 realtors in your geography].”

Get it? Focusing matters. You need to recognize that when you focus your business, you’re deepening your business, not shutting down revenue streams.

I don’t mean to be Captain Buzzkill. I’m not saying to cease entertaining and exploring serving different demographics or client challenges.

Ideally, you’ve figured out your niche before you launched your business, but for some (including yours truly), we need a little more time to experience the landscape of what’s out there, because we’re still figuring out where we want to play. IMO, that’s fine, BUT it has to be done with an awareness that this period is exploratory, and that you’re actively evaluating each customer scenario/avatar for likes and dislikes so that you move through that period as quickly as possible.

Here’s why that’s SO important to not dwell in the zone of not having a well-defined niche :

◉ It’s EXPENSIVE (marketing is much more costly because you’re having to scatter shoot versus sniper shoot). You’ll also burn through your operating capital more quickly because you’re diluting your impact.

◉ It’s EMOTIONALLY EXHAUSTING. Unless you’re in the Members Only Club, you’re low on cash flow. Which means you’re overburdened because you’re trying to do a ton yourself, or with a crazy-lean team. The business is not going to do great when you’re not niche-targeted, which is going to sap your drive and sense of optimism (both of which are tough to sustain for ANY entrepreneur).

◉ You’re a PAIN IN THE ASS to network with, and I won’t refer anyone to you. I ask you what you do, and 30 seconds later you’re still telling me about your “businesses.”



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◉ It’s SIGNIFICANTLY TOUGHER to scale. I don’t know about you, but it took me a LONG ASS time putting in a LOT of hours before I got the cash-flow machine working. Think about how hard it is to do it in one arena, let alone several simultaneously. (As an aside, my business did not take off until I narrowed my niche).

Bottom line: specify as soon as possible. If you need to have a fling before you commit, do it, but know what you’re getting in for. And remember: you’re always going to have a halo effect around wherever you plant your stake. Just trust me: you have a much better chance of making it through the year-one gauntlet if you have a niche for both demographic and situation.



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4. They let their inner-critic replace them on the org chart

I remember when I used to spout some dumb-ass shit like “nobody is harder on me than I am on myself.” Sigh…. Experience has taught me that launching a business is a straight-up street fight, but I watch a lot of entrepreneurs confuse “being tough” with being “tough on themselves.” In the end, it makes for a very unhappy, unconfident, scared, catastrophising mess of a leader that usually creates a very toxic corporate culture. Life hack: don’t be that guy.

I’m by no means saying to go all kumbaya when adversity and challenge show up at your door. Sometimes a situation needs to get kicked in the jimmies. But what I am saying is that entrepreneurism is going to tear at you in ways you’ve probably never experienced—just don’t tear yourself up with it. You can’t be your own hater during your first years—this is a departure from standard operating procedure for the majority of us.

So…if you were raised tough, if you consider yourself tough, if you haven’t become an ascendant master yet, etc., this mantra of “outward toughness, inner softness” is going to be a challenge for you. Respect it appropriately and dedicate time and support to evolve. Ignore this advice and I promise that you will pay the price for it, and it’s going to fucking sting.



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Here’s why it’s important: think about when you’re scared, unconfident, anxious and worrying about avoiding failure? Tell me about the caliber and quality of your decision-making during that phase—how good was it? It sucked, right? You make A LOT of decisions in your first year of business. Like mucho, mucho decisions. The quality of those decisions determine the trajectory of the biz. Need I say more?

The first year is no joke. When you’re exhausted and think you can’t, how much energy do you have? You need to be your best friend and biggest cheerleader at all times, and if you don’t know how to do that, you need to work with someone who can teach you. You don’t have the time nor the resources to be going after yourself. And guess what? ESPECIALLY if this is your first run at a business, you are going to make A LOT of mistakes—there’s really no way around it. If you’re not compassionate with yourself, celebrating your wins, honoring your emotions, and allowing your learning curve to unfold, you’ve already got your back against the wall.

So how to you make traction on this one? Here’s some suggestions:

◉ The research is this is beyond debate: you need to be meditating. IMO, mastering the emotions of the first year is way harder than mastering the business. If you want to be an impactful and effective leader, you need to learn how to master your head and heart so that you can perform to the best of your abilities under extremely challenging circumstances. Check out The Art of Mindfulness by Thich Nhat Hanh, and try out an app called Insight Timer. And don’t forget the Stephen Covey quotation: “To know and not to do, is really not to know.” So don’t gimme any of your “yeah, yeah, yeah, I know I should be doing that” bullshit! Become a doer/practitioner, not just someone who can recite the wisdom.

◉ Are “fuck it” the last words that go through your mind before you make most decisions? Don’t kid yourself—the first few years are an emotional roller coaster—what’s your action plan for how you’re going to navigate that volatility and ensure that you lead as a leader, and not succumb to inner-critic sabotage? When’s the best time to dig a well? Before you need one. Get a support team and check-in process in place before you open the doors, or asap if you’re already doing business.

◉ Take an inventory of yourself and get it up on a vision-board (or whatever the hell the kids think is cool these days). Who’s your best self? I.e., once you identify that your inner-critic has taken the helm, where to do you pivot to? If you don’t know where you’re moving to, it’s tough get there! Map out what you look like as a leader. You’re in pioneer territory at the sharp end of the spear. You’re literally making this up as you go, but your operating style is toggle: proactive or reactive is your dominant mode. Be a pro.



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5. They don’t get the support they need and try to do it all themselves

There’s this absurd, fantastical stereotype that being a self-made entrepreneur means doing it “all by yourself.” This couldn’t be farther from the truth, and if you don’t want to be a statistic, you need to get this into your head.

Unless you’re some freak anomaly, you will survive your first year, by one way, and one way only, and that is with the support of one serious loyal tribe of mofo’s. Whether they are relatives, investors, customers, partners or some mix of those four, your ability to draw deeply from those wells will dictate whether you pull this off.

If you’re one of those hard-ass types that tries to get all tough guy and buck this—I implore you to focus your pride on your outcomes and not on how you got it done. (I can’t wait to hear the martyrs pipe up in the comments on how they did it all on their own. I call bullshit!)

There’s the ol’ Thomas Edison quotation to the effect that most people had no clue how close they were to success when they chose to quit. In my opinion, when most entrepreneurs closed their businesses, they had no clue that they were surrounded with all the help necessary to support their business and keep it alive—unfortunately, they turned inward when they needed to have been focusing on turning outwards.

Especially if this is your first go of entrepreneurship, what in the world makes you think it’s a good idea to go this one alone? Ego? Pride? Bad relationship with money? They’re all just stories. You are 100% responsible for your business outcomes, and as

Christmas, 2016: I bought a tree so big I couldn't get it out the front door so I chain-sawed it into pieces while our 2 year old twins

watched in horror.



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such, you are 100% responsible for enlisting whatever support you need in order to achieve your mission.

I understand that the thought of doing it all yourself brings with it a short-term sense of satisfying self-approval. But you know what’s fun? Running a successful business. You know what sucks? Bellyaching at a bar at 11am about how you “used to have a business once….”

Repeat after me: “polished executive functioning is critical to my success.” Build your role around your strengths. Intimately know exactly what your role is in the business and in the business model. What are your areas of giftedness, and do you structure your time to spend as many hours of the week as possible leveraging those talents? What support do you need to make the business explode and how are you going to get it?

I bet you can name at least four aspects of your business that you 1. Don’t like, and 2. For which there is someone out there who can execute those functions faster, cheaper, and better than you can. Get the support you need—delegate, outsource, cease and desist. Focus the majority of your hours on what you do great, and avoid taking ownership over tasks or projects simply because you “can do it.”

I also bet there are several areas of your personal growth or entrepreneurial evolution for which you could use a mentor. Have you ever heard of teaching yourself wisdom? Of course not, it doesn’t work that way. Get the support you need to grow and scale as quickly as possible. From an ROI point of view, it’s often well worth it. Join a mastermind group. Hire a coach. Get a book keeper. Retain a digital marketing expert. Ask a few businessmen and women you respect to be on your personal advisory board.

You know best where you need extra firepower—write up your wish list and start asking for referrals to build out the team you need to get through the danger zone of growing a business as quickly as possible.

Think about it—even Tiger Woods has a swing coach.



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To my dearest entrepreneurs,

If you saw yourself in this book, if it made you laugh, hell, if it even remotely made sense to you: surround yourself with some like-minded folks and join us at www.JayRookeCoaching.com. We’ve got all sorts of resources like an online community, an entrepreneurial assessment (c’mon, you know you love those “which one am I?” tests!!), blog, my podcast, etc.

I’m also going to be sending a few freebies your way, so keep an eye for the next email.

Until then, think about what your business most needs right now; then commit to working on it for the next month.

Deliberately create a culture of change and growth—especially if you’re a solopreneur, and remember the corporate culture you create starts with you. So don’t operate in a silo ☺

Warmly,

Jay Rooke

PS: If you thought this e-book was “the message you needed to hear in the way you needed to hear it,” let’s try and abolish average—please forward the signup page to someone who needs to hear it. Thank you for all your support!


contents · 5 dumbass mistakes (otherwise smart) entrepreneurs make 3 to my fellow entrepreneurs,...

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