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Improving productivity is such a hot button topic. You’ve read all the articles and know why it’s important. So you’ve tried different tactics to wage war against your to-do list.

But, that dastardly to-do list continues to grow!

Here’s the problem: implementing productivity tactics are just so damn hard! It’s not so easy to change your habits and every productivity trick is essentially a change in your habits.

Want to wake up earlier to improve productivity? That’s a habit change, and therefore extremely difficult to do.

Want to start writing down your goals? Another habit change.

How about exercise each…


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Photo by Brooke Cagle on Unsplash

In the startup world, you hear a lot of talk about your first ten hires. Your first ten hires will, in all likelihood, end up being your leadership team as you scale. They’ll get the most equity (roughly one point each) and play the biggest role in growing the business.

The logical takeaway then is that you need absolutely incredible people to fill this role.

It’s why Y Combinator preaches to their founders to spend ~50% of their time on hiring, and why “Thiel’s law” is that a startup screwed up at the start has no chance of recovering.

But…


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Photo by Annie Spratt on Unsplash

Let’s level-set: it’s incredibly difficult to predict which startups will end up growing and which will collapse. There’s a whole venture capital industry based around figuring out which startups will see hockey-stick growth. If you are great at it, you’ll end up being a billionaire.

I’m not a billionaire, so it’s hard to claim that I’m great at picking startups that will grow.

But after years working at and consulting for dozens of startups, there is one similarity that really rings true about the startups that really seem to grow.

Here’s what the best startups have in common: they cannot…


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Photo by Mike Kenneally on Unsplash

Unlocking productivity improvements is a huge topic. There are thousands of very-well written articles here on Medium and other online resources. Hell, I’ve written a curated story here on Why You Should Trade Sleep for Productivity.

Most of the articles, including mine, focus on how to eke out a little more efficiency. After all, if you can finish your to-do list in 10% less time, then you are improving your productivity.

But, reflection on the past couple of weeks has changed my perspective on that.

In looking at my past few weeks, the most productive part of my day hasn’t


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Photo by Christin Hume on Unsplash

Leadership is a topic I write about quite frequently. It’s a topic I believe is really important and is worth all of us studying to figure out how to be better leaders.

It’s why I wrote about your very own personal leadership development plan and your proven ten minute exercise to be a better leader.

Even though I’ve studied, and practiced leadership, for years, there is always more things to learn.

In fact, I just had to tell my former boss that he now is working for me.

So, why does he now report to me?

The reality is that he isn’t performing where he needs to be…


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Photo by Yuliya Ginzburg on Unsplash

There is nothing in this world more important than self-improvement. No matter who you are, or where you want to go, nothing will happen without a complete focus on getting better.

That claim holds true no matter what your goal is. Whether you want to start a billion-dollar business, send rockets to Mars, or be the best parent you possibly can be, you need to be dedicated to self-improvement.

Think about it this way: a baby just born has zero possibility of achieving any of those things. …


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Photo by jean wimmerlin on Unsplash

One crazy thing that seems to come up constantly in the workplace is conflict. You know the kind: it’s a conflict between two employees who just don’t see eye to eye and they don’t want to collaborate.

As a leader, there’s often nothing more annoying than needing to deal with two employees on your team who don’t get along.

Unfortunately, I had this happen not too long ago with a team I lead.

Two employees who don’t like each other isn’t the biggest deal in the world. After all, there are always people we don’t like and who rub us…


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Photo by Perry Grone on Unsplash

As a startup, your product launch date is exciting. After all of your work, the hope is you launch to great fanfare. You finally unveil your product, the market loves it, and you rapidly grow. The New York Times notices your launch and writes a big story about you.

You know, just like Airbnb.

Or, not like Airbnb. They famously launched themselves a dozen times because nobody noticed the first couple of times they launched.

Either way, a product launch is a big day. You doubtlessly had months of effort and work to get ready. You want people to see…


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Photo by Joshua Ness on Unsplash

A few months ago, I was on the phone with a business associate of mine. He’s about 20 years older than me. He makes more than a million dollars a year, and it’s not an exaggeration to say that decisions he makes impact billions of dollars.

Essentially, he is an influential dude. He should run all over me in every conversation we ever had.

But, in this case, I was on the phone with him while pacing my apartment. My girlfriend was listening to my side of the conversation.

I got off the phone, and she looked over. She cocked…


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Photo by Christian Wiediger on Unsplash

The other day, I saw the Amazon commercial where a young man is taking care of his grandfather while listening to music through an Alexa device. He leaves for the day, and returns home to his grandfather playing the same song on the Alexa.

It’s a really cute commercial. It tells a cute story while also demonstrating the value that Alexa can add to your life.

But, here’s the crazy thing: that was maybe the 100th time that commercial has come across the TV. What made this instance unique was that I could now recite every single word of that…

Dean Woods

Startup executive, recovering consultant, Wharton Grad. I write about real startups (my venture backed day job) and micro-startups (my bootstrapped nights)

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