The Founder’s Evolution Stage 2: The Startup Entrepreneur

I have a brilliant practice golf swing. You know, that obligatory fake shot you make before you step up and hit the ball. I’m great at that fake shot. It’s smooth. It’s powerful. It looks good. And I imagine the ball going right where it’s supposed to every time. 

It’s so good that I’ve concluded that it’s not my swing that is the problem. The real problem is when the ball gets in the way. That thing has a mind of its own.

Many brand new entrepreneurs and founders face this same feeling. They’ve thought and dreamt of starting their own organization over and over again in their mind. They’ve seen the freedom they can have. They’ve smiled as the thought of success rose to the surface of their mind.

And then they start. They make the leap. They step up to the ball. And instead of that beautiful straight line off the tee, the ball slices hard to the right. And now they’re in the woods.

The wonderful thing about it is most of us are fine with that. Much to our family and friends’ bewilderment, we’d rather be hacking away at a ball 40 yards into the woods and be in the game. That’s infinitely better than hitting perfect shots on the driving range, or even worse, watching someone else hitting perfect shots in their own game.

Is that a smile?

And so, if you were to go out and ask any random startup entrepreneur how the new business is going, you will get a huge smile followed by a whole list of superlatives. “It’s wonderful.” “It’s amazing.” “I’m loving it.”

They’re going, and the adrenaline is flowing. And in many ways, it’s a truly wonderful time. 

Simultaneously you feel like all your life has prepared you for this moment, AND like you are way in over your head.

Because you are.

And despite the smile you show everyone around you, inside, you are plagued by the question: What was I thinking?

What was I thinking?

My favorite definition for the word entrepreneur is someone who quits working 40 hours for someone else to go work 80 hours for themself (and get paid less to do it).

Even though our news media and podcast heroes all celebrate the seemingly mythical wonder-world of entrepreneurism, all the fluff has a way of disappearing when you are still up at 2 am trying to finish a project, prepare a shipment, or find out how you can hang on to enough cash to make it until your next sale.

The collective mythicizing of entrepreneurship is a profound disservice to those brave souls who were willing to put the safety of the sidelines behind them and get in the game.

Most of us walk in blindly and are in for a rude awakening. It’s for this reason that my advice for the question, “Should I start this business?” is always, “No.” If there is any other way to achieve the end you have in mind, take it.

Because entrepreneurism is hard, and starting something from nothing usually fails.

But don’t for a moment think that I am anti-entrepreneurism. I love entrepreneurs. I deeply respect founders. And I will bend over backward to help those already in the game obtain all the success they desire. And if you choose to leap, I’ll support you too.

I just want you to know what you’re getting into ahead of time because it’s not going to be easy. We call this stage for the organization Early Struggle, which is best described as waking up each morning, finding a sharp object, and banging your head on it again and again.

The goal is to stay in the game long enough to figure it out and win!

Okay, I’ve admittedly been a Debbie Downer so far because that is a message most people won’t hear anywhere else. But now that you know what you’re getting into let’s take a look at how you can succeed in the second stage of your entrepreneurial journey.

The Star Player

And succeeding at stage 2 is all about becoming the star. It’s about becoming great at what you do. It’s about building a better widget. Closing better deals. Marketing to those missed by the masses. 

It’s about stealing victory from the jaws of defeat, and you do that by being the best yourself.

It’s hard work, but it’s a lot of fun. The better you get, the more the world opens up to you. There’s recognition. There’s compensation. And there’s proving to the whole world you have what it takes.

This is what makes a star a star. They do what they do better than anyone else. And that’s why they win. That is, quite frankly, why they make the big bucks. They are the best of the best, and the game heavily rewards the best. 

Much effort goes into finding players with the best builds, the best stats, the best training, and the best instinct for the game. Winning is physical. It’s tactile. It’s concrete. 

It’s all about what you can do.

It’s also not about a lot of other things. Even good things.

You don’t have to be a great leader to be a star. You don’t have to be a great manager to be a star. You don’t have to be a great strategist or predict every move your market will make. You don’t have to think “team first.” You don’t have to plan every move of every play. Star players aren’t encumbered by all of these other thoughts. And it is precisely that focus that makes them great at what they do. 

The essential strategy for Phase 2

And that is the essential strategy for Phase 2 of your Founder’s Evolution. You need to focus on getting better at what you do. It’s not as much strategy as it is tactic. In fact, too much strategy at this stage can be counterproductive. Instead, embrace the relative simplicity amid the maddening busyness. When you do, it allows you to shorten your focus and excel at executing on the fundamentals repeatedly.

So hyper-focus on getting better at what you do. And if you’re wondering how, here are a few suggestions.

Get clear about what it is that you do

This seems obvious. So obvious that it is often overlooked. But you would do well to have clarity about what you do. Or better you what you actually should do. Often getting clear about what you do will help you realize there are some skills you are seriously lacking. Things like sales, marketing, time management, and prioritization all surround the “thing we do” and, if not dealt with, can quickly sabotage the effectiveness of “what we do.”

Develop you

There is a return on selfishness in these early days. Your work is so central to the success of your organization that it is right, even necessary, to focus on developing yourself. You need to produce more, in less time, with fewer distractions.

When looking for help, you want to find people who can specifically help you get better at doing what you do. 

You may have a few other employees around you at this point. If so, that’s a blessing. Enjoy it. But don’t feel too much pressure to develop everyone together. 

The ideal (read most effective) scenario is often where you make the plays, you are the star, and you bring people around you who can make you better.

Sure this can be an ego thing for some. But it’s just as much about ego if you won’t do it simply to prove you don’t have an ego.

The key to success in stage 2 is to orient your organization around you doing what you do best and everyone else filling in the gaps.

Finish things

You’ve got to get the proverbial ball across the line. That means you need to finish what you start. There is an endless opportunity to start and try and explore new things. Those who succeed the most in this stage do so by trying some things and finishing most things.

And this is actually one of the greatest gifts that stage 2 has to offer. You have the greatest capacity to quickly finish the tasks you start. Years and decades from now, you’ll look back on this time from your corner office suite and think fondly of how nice it was to simply do what needed to get done. You don’t have to ask anyone. You don’t have to get anyone’s buy-in. You don’t have to coordinate 40 people to get them all moving in the same direction.

It’s point and shoot. And while for most founders starting is a lot more fun than finishing, if you’ll let it, finishing can create its own satisfaction. And as hard as it is now, at some point in the future, you’ll look back on these days and quietly wish for them once again.

Transitioning Out of Stage 2

The transition out of stage 2 is a curious one. We long for it to happen. But when it does, we wish it hadn’t happened so soon. 

You see, stage 2 is one of the best stages to stay in for a very long time. It’s great to be a star. Once you get to the top of your game, you’ll want to stay there. It feels great. Unlike the world of sports, where a player’s primacy is limited by their physical capacity, the world of business (or nonprofits, etc.) offers much greater longevity to its stars.

Many founders spend the rest of their careers in stage 2 and love it. Of course, time spent as a Startup Entrepreneur is no panacea, but it can be incredibly rewarding and fulfilling.

And the next stage, though it brings progress in your journey, doesn’t feel quite as good as you make the transition to Stage 3: The Reluctant Manager.

So keep Stage 2 going for as long as you can. Keep things simple for as long as you can. But if your vision requires more than you can achieve alone or with a few others, it’s time to make the transition to Stage 3. And to do that, you need to hire or promote a #2. The title for this role doesn’t matter. But what must be true is that they also need to be a star player. Bringing in another high-capacity individual will create room for further focus on what you do and how you succeed personally. You will also create a whole new host of growing pains that will stretch your leadership as you take the next step on your Founder’s Evolution.