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My Leadership Insights are rooted heavily in 15+ years of experience in the training and personal development industry. In my day-to-day life, I help both individuals and corporations empower their growth through knowledge and career education.

What You Should (And Shouldn't) Do as an Entrepreneur

By Jeremy Tillman Jan 14, 2019
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Do's and Do Not's Entrepreneur

I'm often asked what are some of the MUST-DOs and the absolute NEVER-EVER-EVER-DOs as a business owner. And so, some of the best advice I can give to new (and seasoned!) entrepreneurs is this:

These are the things you SHOULD be doing... Not occasionally, but always, always, always!

1) Don’t let anyone squash your dreams

It’s in the nature of entrepreneurs to dream -- it’s essential. Along the way you will encounter naysayers.  Don’t worry, use their doubt as motivation but also learn from it. Consider their perspective, tweak if you need to but never give up. 

2) Trust your elders

For the most part, anyway, and seek out one or two mentors. Entrepreneurship is a tough and rough road to travel alone.  You are going to need people around you who’ve been there and “endured” that; those who can provide wisdom, counsel and encouragement

3) Build an amazing team

Never settle! Be relentless in your pursuit of great people who align with your vision and are smarter than you. You can’t get there alone.  (I learned this the hard way of course.)

And now for a few things I encourage you to NOT DO -- EVER!

1) Forget to plan for failure

There might be a double-negative here, BUT it's important to understand it in this context -- If you FORGET to plan or explicitly choose not to plan for failure, then YOU WILL LIKELY FAIL. Again I speak from experience -- I built plans that required perfection and used every drop of capital we had in pursuit of them, the problem was I left no room for failure.  My plans required 98% success and we hit maybe 85% success on most of our objectives, but still found ourselves fighting from behind.  Rarely, rarely, rarely will a plan go exactly according to plan especially if it’s one that spans multiple months.  So plan for things to NOT go right.  Plan for things to take longer, plan on growing from your mistakes because they will happen.  Adjust your plans frequently especially when you know you are deviating. Hard work and long hours won’t bail out every plan that hits an unexpected detour. Make wiggle room your very best friend.  

2) Forget to consider the customer

Sometimes we get so wrapped up in our ideals we forget to fully consider the customer’s perspective. Great entrepreneurs must first be great listeners.  A solution that doesn’t solve a customer’s problem isn’t a solution at all.  The only way to know what a customer really needs is to seek out and listen to their perspective.  There are so many tools now that allow you to interview customers, model the customer, A/B test and so forth.  One of the things I like to do from time to time is answer support calls.  I almost always walk away with insights and ways we can improve.  As leaders we should never get too far removed from our customer. 

The first version of TrainUp.com was so awesome, you had to click 8 buttons before you could hit search.  An engineer must have designed this.  Adopt quickly to the market and what you learn from customers.

3) Take things too personal

As entrepreneurs we must have thick skin, we must be humble, we don’t know it all and we can’t take feedback of any kind too personal. It's also important not to let positive feedback go to your head and to allow negative feedback to stay there.  Look at every situation as a learning opportunity -- Even the insults.  I’ve had plenty of them in my career.  I started TrainUp.com young and I remember one of the first trade shows I had an executive come up to me and say something to the likes of "...what could a 24-year-old possibly know about enterprise HR?"  I kept the offense internal, took it as a challenge.  I asked them on the spot for their top HR challenge and immediately gave them my 24 year old perspective... They went on to implement that very solution. 

This strategy works at home too.  I tell my wife sometimes you have learn to “play the game” when someone assumes something about you or offends you, as our first reaction is often to be defensive.  It’s so much more fun and relaxing to take it lightly.  For instance we were at the DMA (Dallas Museum of Art) not too long ago with our 2-year old son Miles, and one of the workers approached us and said "so it’s your first time here...?"  We’ve been members for 5+ years and have visited at least 50 times so my wife took it a little personal.  I just laughed and let the worker finish her spiel and we did in fact actually learn something new.  You never know where that great insight or spark is going to come from so don’t take things too personal.  If I’m honest it hasn’t been easy as an African American in business but I never use that as an excuse nor allow myself to be overly offended when something is assumed because of the color of my skin or any other bias.

My final advice is this: don’t try to win every battle.  Just the most important ones. And when you figure out the difference between the two, give me a call…

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My Leadership Insights are rooted heavily in 15+ years of experience in the training and personal development industry. In my day-to-day life, I help both individuals and corporations empower their growth through knowledge and career education.

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