The Entrepreneur Puzzle

Putting all the pieces together is a lifelong journey

From the very first day you get the bright idea to try your hand at entrepreneurship, you start playing one of the most complex, multi-level games of problem solving.

You start by understanding yourself then puzzling out your ideas. After that it’s all about your people, the strategy, the execution, managing success and mastering life after business. Entrepreneurship is the ultimate Rubix Cube so be prepared to be unprepared, roll with the punches until it’s time to strike, plan for some shit but always keep the hope alive — if you can learn to love the puzzle then you will learn to love this life.

Personal Perplexity

It all starts with you. The first challenege is decoding your purpose, direction, skill set, internal drive, committment, and tempermant. I’m sure there are more, but these are some good pieces to get started with.

Why are you doing this and what made you want to be an entrepreneur? While there are really a ton of different answers, in my mind it can be narrowed down into two main groups. You’re either a passion project entrepreneur — someone who is in this game for their art or love for one business, industry or project. I see this a lot with restauranteurs or musicians and other artistic types. The other group are the creators — this type of entrepreneur sees business as more of an overall game. They think in scale, build many different business, and often move from industry to industry for new challenges. Again, I realize there is some middle ground, but if you can make this distinction and figure out which side you are leaning towards, you will have one big piece of your personal puzzle figured out.

Your skill set and direction are like two sides of the same puzzle piece. Being self aware at this stage is crucial, a lot of people want to jump into a business, which is trendy or interesting, but they have no real skill to accomplish the job. This stage is about finding the things you genuinely love to do and how your skill set crosses over that line. This is your sweet spot and it will give you clarity as you move forward.

Self motivation, internal drive or committment — how are going to keep that fire burning inside you for the next 30 years? Motivation is fleeting, very much like a glass of water, you probably need eight doses a day to keep a healthy mind. In my experience, this becomes the habit of self motivation after a few years, so there is some light at the end of the tunnel. Your internal drive is really work ethic. Will you work 12 hours a day and will you stay committed long enough to put in 43,000 hours to be the greatest at whatever it is you choose to do?

Temperament is one of the last personal pieces, but I have used a very broad term to describe a puzzle in and of itself. This is really about your attitude, maturity, ego, emotional turbulence, ability to manage others in crisis and keep a level head whether things are going great or really fucking bad. This is an ongoing battle that truly never ends. Each day and every situation will challenge you in new ways, you just really need to have a strong moral compass, kill your ego 100% of the time and be sure that every experience you have adds to your arsenal of personal communication skills. I truly believe that your Emotional Intelligence (EI) is fed and developed through experience so don’t be afraid to make some mistakes and upset a few people while you’re growing. Just be sure to make pr0gress and learn from every one of them.

Big Idea Battle Ship

So, you’re an entrepreneur, tell me about your big idea.

What do you love? What are you good at? Where is there a gap in the market? How are you going to fill that gap and what is your value proposition or unique trait? Finally, who is leading the market and which competitors should you keep an eye on as you move ahead?

I love this part of the process becasue I find it to be the most creative aspect of your journey. There are no limitations on what you can do and how you want to do it. We briefly touched on this before, what do you love and what are you good at? This is ocean of thought that your big idea should come from. You want to love the space you’re getting into so your passion is always on high. We’re also going to take a page out of Gary Vaynerchuk’s book and say, fuck your weaknesses, double down on your strengths. While the creators will inevitably jump industry, starting off where you’re most comfortable and confident will go a long way towards your success.

You have your market in mind, so now you have to figure out the problems you’re going to solve. Is there a gap in B2B sales or a new technology that you could bring directly to the consumer? Maybe you’re going to shake things up and come to market with a completely different platform. I say ‘Fuck it, shoot for the stars!’ This is such a broad arena to work in, but the more you know about your business the easier it will be for you to solve the big industry problems.

When working to fill the gap, I would design a few iterations and do some testing. See how easily your new idea or plans can be adopted into the market and how interested the end user is in adapting to the change. This step can range from quite complex to quite easy, it really depends on whose problem your fixing and for what reason. Your value proposition needs to come into play here, what are you offering, who are you offering it to and how will they get better value going with your brand? This is key to carve out a segment in the market. Blue Ocean Strategy is a great book for anyone who wants to understand more about creating an open space in the most treacherous looking industries.

The competition — while I hate to pay attention to others, if your value proposition is not strong enough or another, larger competitor can rip your idea in 20 minutes, you need to know before launch. Do your research on these guys and gals, I don’t think this needs to be a long term study, but it is quite important out of the gates.

Team Building Tetris

Perhaps the most important and complicated puzzles of them all is building your team.

Early on, it is essential that you find the right people to connect with you not only in vision and direction, but passion and ambition. You need to find great number 2’s, 3’s, and 4’s who want the roles their in, they need to feel appreciated, the team synergy has to be on point and trust has to be as clear as day or you’re fucked.

Then you need to find a way to keep this train moving as you expand and add everyone from employee number 5 to 500. How do you plan to build and hire? What is your management strategy and how will you keep your people driven, motivated, creative and perhaps most important — happy?

If I had a bit of advice to give someone hiring their first 4 or 5 employees it would be, hire people that you have great synergy with and who believe in the long term vision. Don’t just hire friends or family or some guy because he has the skills, a ton of people have skills. Startups are tough and if your core team doesn’t connect on a deeper level than just work, I fear for your success. Walk in knowing what you’re looking for in these people, create that vision before hand so you know when you’ve found the right team members.

So you have the core team in place, and everybody has their hats to wear, but now you need to create a culture that fits both your corporate values and the management style you plan to employ. I think a lot of companies get this step wrong and just try to follow industry trends. Like foosball tables, free snacks and a little meditation are what creates culture (btw these are great if they actually represent your culture). Often you see these perks but the management style in no way fits the design. This is misleading and will bring the wrong employee expectation through the doors on day one. Companies often lose sight of what they are really all about and what type of employees they’ve hired to work for their company. If you understand who your company is from the get go, this is an easy thing to carry forward — it will permeate into your hiring, how your employees treat one another and essentially how your company will represent itself. Culture can and will change over the years, but you need to cultivate a certain environment or you will have a challenge maintaining consistency under your roof. Now you can take this core and culture, and hire from 5 — 500 with these parameters in mind.

Keeping people driven, creative and happy — at scale — is probably the most challenging and ongoing task as a leader. Early on, you have to tap into each individual employee and understand what makes them tick. What drives them? Is it money, power or success? How are they best appreciated? Is it through individual praise, group recognition, friendship or financial gain? You need to know when their having a bad day, when they need some space, and what their primary strengths/weaknesses are…essentially you are a full time leader and part time psychologist. The Steve Jobs dick approach is just not my idea of solid management. Think of how you would feel if someone treated you like shit? I’m not taking away from Steve’s amazing accomplishments, I’m just saying — you catch more flies with honey. As you scale, this becomes more challenging, but until you’re at 500 employees, you should make an effort to connect with your people and let them know you care…otherwise how can you expect them to give a shit about your company every day?

The Enigma of Execution

How do you operate from day to day, month to month, year to year, etc? There are obviously standard business practices, but there are unique challenges from day one, like on-boarding new employees properly, prioritizing tasks, building systems and meeting deadlines…and this is just the beginning.

You need to have a clear plan, a proactive plan, on how you are going to go from idea to execution. How you plan to hit the market, product testing and iterations, marketing and sales channels, packaging services, manufacturing and distributing products, handling customer, employee and systems issues?

How are you going to mitigate risk across all these channels and deal with the unforeseen issues that arise? What is your financial strategy for you’re up and down — where do you cut costs? where do you spend to improve?

I’m a big fan of building a wire frame or outline for every step that I know will come into play. I don’t over plan, but I recognize what I’m up against and I have a strategy in place to manage each step. A lot of this will be a fill in the blank game for your first run at entrepreneurship, but you want to be aware of things as simple as employee on-boarding or they will slow you down when the time comes.

Here’s is your strategy: Sit down with some or all of your core team, they all serve a different purpose so their experience/expertise can be crucial here. Spend one full day at this — notice I gave it one day, there is no need to over plan — and walk through each step from incorporating your business and on-boarding to product iterations, ad testing and distribution networks. I mean really dig into the process from the first step you make as a leader to the satisfied customers. For every step of the process, have a crisis management plan so that you are prepared for the inevitability of fuck ups, but also to avoid panic mode when shit hits the fan.

The other thing you want to do here is create a linear or somewhat linear system of execution so that you are not prioritizing tasks or making purchases that are out of sequence with your operation. For example, don’t go and strike a distribution deal with FedEx on day 1 when you won’t start shipping until month three — this sounds silly, but I’ve been apart of this stupidity before. Another example is, let’s say you built Uber, you want to be sure you’re not bringing on too many riders before you have any drivers or that customer base will fall off and likely never come back due to a bad first impression. You need to be sure your efforts are balanced so the Uber community builds most effectively.

There are a million more examples, my point here is spend a day with the team, make a road map, consider all the speed bumps and growth opportunites then move forward.

Solving Success

This is an interesting and often underestimated quandary for a lot young entrepreneurs. Having success sounds like the easy part, but it can certainly come with its very own set of problems

First, how do you know you’ve hit success? What does your success look like? People aren’t clear so they often keep chasing the carrot. Have a vision for what you want in life so you can enjoy closing this chapter in your life.

Managing wealth without an improvement in your financial consciousness can be a disaster. You may also need to be self aware so your ego doesn’t fly too high and you Justin Bieber your business. I mean really, how many cars, boats, houses, exotic animals and parties do you think you need to do before you’re satisfied? You’ve won the game so there is a slight bit of awe, don’t let this shit get to your head.

This may sound unorthodox, but one thing I’m very big on is knowing what your success looks like. We’ve all heard or know of the money hungry entrepreneur who has sacrificed all for the dollar — family, friends etc. I believe the best way to curb this behaviour is have a clear picture of what your success looks like before you embark on this journey. For me this has a two-fold value. For starters, it gives you a big goal to work towards, your pie in the sky if you will. Now all of your actions and intentions are driven by this set of goals. The second part is the end game, when you know what success looks like — whether it’s $50 million or 100 restaurants — you will be able to slow down, take a breath and move on once you’ve hit it. Yes, this vision might grow or change slightly over the years, but it will go along way to motivate and also keep your life in check as you hit your stride into success.

Another big challenge that comes with success is money management. If you’ve never had money, but now all of the sudden you’re sitting pretty, you need to acquire the right mindset to properly manage it. There is certainly a time to enjoy the fruits of your labour. Go buy the Ferrari you always wanted, the castle on the hill and a yacht with a heli pad. That said, when does it stop? When is enough, enough?

We’ve all heard of the professional athletes horror stories where their earnings top $100 million over the tenure of their career, but they filed for bankruptcy. If you haven’t Google; Terrell Owens, Marion Jones, Mike Tyson, John Daly or Allen Iverson… Their faults vary, but the similarities are ego driven purchases and piss poor money management. You hire a lawyer for legal matters. An accountant for filing taxes etc. Well you should hire a reputable broker to help you manage your wealth, yeah it will cost you a little, but it will make/save you a lot more. As for ego, stop giving a shit about what everyone else thinks of you! They’re not even thinking about you, they’re too busy thinking about themselves so don’t just spend to impress.

Be true to yourself with your money, your decisions, relationships and ego. Try to continue being the great person that got you to where you are, only better.

The Mystery of Mastering Life After Business

This is for the long term, this is the puzzle that will take many years and change shape many times. In many ways, this is sort of the puzzle that never ends as we continue to grow, change and progress over the years.

I wish I could give more advice through personal experience on this stage, but I am still on my journey so the very best I can do is make you aware of what you’re up against.

The first big step is your exit. How do you keep your business going in such a way that you can step back and it will still maintain order, synergy and success?

Money management, which we just covered, is another big retirement factor. You want to be sure you invest or coordinate funds in a way so that your money is always making you money. This way if you live to be 244, you still have a steady stream of revenue to support your 8 generations of family.

Then there is the challenge of simply turning the page and redirecting your efforts in life to family, children, personal development and philanthropy. It’s such a change of gears for most people that it can be a the hardest thing to do.

I’m a firm believer that life is full of different chapters. Going back to your success stage, I think it’s important to be clear with yourself so that you know when it’s time to turn the page for good.

Mastering life after business is really about fully actualizing your life in every way. To me, this includes health, wealth, happiness, success, confidence, love, self love, giving back, and in the end, leaving behind a legacy. I believe each phase is going to be its own Rubix Cube, so just be prepared to tackle all of these puzzles along the way and life will be yours to master.


From start to finish entrepreneurhsip will challenge you with riddles, conundrums, enigmas and quandaries, but it is one of my very favourite things in this world.

Thanks for reading! :) If you enjoyed it, hit that heart button below. Would mean a lot to me and it helps other people see the story.

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