This post is part 1 of a 3-part series.  See part 2 here and part 3 here.

Photo courtesy of gearjunkie.com

When I run, I don’t wear much clothing.  Just my tighty whities and an old pair of Umbro shorts.  I don’t wear shoes. Why I don’t wear shoes while running is another topic, but by the looks I get, you’d think my man bits were flopping around in the breeze for all to see.  People will sometimes let out a faint gasp and point at the freak running by. I’m not naked of course, but I feel exposed and at times uncomfortable with the looks I get.

But this series of blog posts isn’t about running barefoot per se.   It’s about the lessons I’ve learned founding and selling two companies as well as my work advising start-ups. Barefoot running happens to be a great analogy to illustrate the secrets I’ve learned.  In fact,these tips can be applied to accomplishing any activity, which, like running,requires focus, stamina and skill…that’s pretty much everything.

So what did I learn exposing my feet to hundreds of miles of hot asphalt?

Lesson 1:  Feel the street

“But what if a nail or a rock jabs into your foot?”  This is the most often asked question I hear about barefoot running.  It’s a good question until you actually take off your shoes and experience what the ground really feels like under you.  You realize the human foot is perfectly adapted to run this way.  Running barefoot utilizes different mussels to tread lightly with each step.  Your feet adjust as you run, padding your way and giving you instant feedback about the terrain.

Getting real-time feedback is paramount to both running and business.  But we feel more comfortable when we cushion ourselves from what is really going on.  Our padded athletic shoes put layers between our feet and the street, just as corporate life can shield us from the uncomfortable things we’d rather not worry about.

So what’s wrong with being comfortable?  Too often we trade real work for short term comfort, and this inevitably leads to people getting hurt.  66% of runners suffer race ending injuries annually and most businesses fail within the first 2 years. Although seemingly unrelated, both occur when people stop feeling what is really happening underneath them and choose to overly cushion themselves.

Here are three examples I’ve observed of how people insulate themselves to their own detriment and what to do about it:

Engineers tend to focus on the code and not enough on the cash.  I’ve seen way too many smart engineers working on really dumb projects. They let the “business people” prioritize projects and get accustomed to taking orders, thus cushioning themselves from having to answer the tough question of, “is my work really benefiting the business?”  By padding themselves from answering tough business questions, they are complicit in allowing management to waste precious time and resources. If you are an engineer, it is time to get out of your text editor and onto the street.  Ask the tough questions to understand the business model, market size and strategy of your company.  Most importantly, get out and meet your customers.  Really go talk to them.  If you are at a B2B company, insist on going to a sales presentation.  If you work in consumer internet, get out of the building and talk to some real live users yourself.  Get to know what the customer really cares about; it may not be what you expect or what you’ve been told by your product owner.  You may prefer to stay at your desk and that you think of yourself as an introvert, but that’s no excuse.  By getting outside the building and really feeling your customers’ pain, you’ll know if your company is actually making something people want as well as discover innovations you never considered before.

Marketing and sales people tend to cushion themselves from the technology on which their companies depend.  Too often they have not invested the time to understand how their technology really works.  They lob requests over to the product team to build more features without understanding what it takes to build them.  If you think of yourself as a “business guy or gal” and you work at a company that relies on technology, learn some freakin’ code already!  At least understand the basic mechanics of how your products work enough to be able to recommend how to improve them.  By relying on your engineers to cushion you and without a rudimentary understanding of the technology, you won’t know if that killer technical capability you’ve been touting in your presentation actually matters to anyone.  When you learn the technology, you’ll be able to do more than demand features, you’ll know how to build them for yourself, increasing your responsiveness to customers’ demands and finding opportunities you never saw before.

Finally, entrepreneurs cushion themselves when they focus on distractions and tactics, which actually have no impact on what really matters to their business.  Entrepreneurs are better served focusing on the road under their feet, the uncomfortable stuff you know matters most.  Asking the question, “do people love my product?” and dealing with the potentially uncomfortable answer, is all that matters.

Two huge distractions that cushion entrepreneurs from having to do real work are business development and fundraising.  I see too many small companies spending time entertaining calls from big companies looking for partnerships.  More times than not,partnerships with big companies waste time and produce few results. Instead,focus on your own users and their needs. If you’re a small start-up talking with a big company before you’ve reached product / market fit, you’re just serving the need of the person at the big company to look busy.

Raising capital is another area where entrepreneurs get sucked into a time wasting vortex. Sure, capital is often needed for growth.  But many entrepreneurs see raising money as a sign of validation and pursue it way too soon. They think, “If investors give me money, it means I must be right.” Wrong!  Remember that investors are wrong more often than they are right about an investment outcome.  If you raise money for a business making a product no one really needs, you are squandering the most precious thing you have, your own time.  Raise money only when you’re truly ready to scale, meaning you know that the money will go into getting your validated product into the hands of customers who really want it.

Feeling the road and facing the hard reality of what really matters can hurt.  But by being close to what matters, namely yourcustomers on the street, you build stamina, better judgment and skill.  It’s only by listening to the street that you will know if you are heading in the right direction.

This post is part 1 of a 3-part series.   See part 2 here and part 3 here.

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