The hard thing about being a leader is NOT knowing what the next “hard thing” will be. A little while back a friend recommended that I read “The hard thing about hard things: Building a business when there are no easy answers” by Ben Horowitz. I was grateful for that suggestion. Anyone who wants to be a leader – or needs to – should read this book. Without spoiling the punch line if you haven’t read it, here is my takeaway from that book:

Being a leader is very hard, so you better be harder than very harder to succeed.

Tough As Nails:
Leaders should be emotionally as tough as nails. Why? Because entrepreneurs repeatedly face rejection, criticism, competition, legal battles, negotiations, and possibly worst of all – doubt. Some people may be genetically tougher or more oblivious to some of these challenges. For example, many successful entrepreneurs exhibit mildly autistic behaviors, which may help them reject emotional challenges (both external and internal). Others grew harder through experience. Hopefully you were born with a certain level of thick skin and grew thicker skin through life experiences.

Not How but Why?
There are many ways to grow tougher. But even more important than the “How?” is the “Why?”. If there isn’t a reason to grow a thicker skin, why would you suffer to build callouses? Some people feel trapped, so they grow thicker skin because they don’t see any other choice. The job requires it. But some vague notion of necessity can fail you in hard times. In hard times, you need to know why you’re putting up with major pains. You need to steel yourself with a reason to soldier on.

It may seem obvious, but it is worth mentioning … if you’re not passionate about your customers or the problem or the technology, you will probably burn out. Passion keeps the engine running even when you’re rebuilding your pitch deck again despite flying on the most uncomfortable redeye of your life to see yet another VC for this round of funding. Take time to remember what you’re passionate about and why you’re passionate about it. Remind yourself on a daily or hourly basis. Leave yourself visual cues as a reminder of why you’re passionate about your startup. Maybe it’s a picture of your favorite customer or a nice comment from one of your peeps. Surround yourself with anything that builds your passion.

For My Peeps:
Some of the hardest people I know will walk through fire for others, but not for themselves. This type of entrepreneur doesn’t build a company for herself. She starts the company for the customers and she continues growing it for her employees. Each employee has a dream, family and friends. Struggling on for your employees can be a great motivator. For example, laying off a third of your employees almost becomes bearable if doing so saves the other two thirds. If it were just you, you might crumble and throw in the towel. But because you have the other employees to look out for, you stay strong.

Rise to the Challenge:
Some people shine when they are faced with a challenge. Olympic champions are the gleaming example of holding up under pressure. Startup C-suite execs are another great example. If you’re the type of person who stands out when the pressure builds, then you’re suited for startup leadership. If you’re the type of person who seeks out the opportunity to overcome challenges, then you’re suited for startup leadership.

Path of Least Resistance:
Having just stated that leaders need to step up to a challenge, I’m about to contradict myself. I always recommend that the leadership avoid as many challenges as possible and focus on the few they can nail. There is an important distinction between pursuing a challenge because it’s necessary and pursuing a challenge because it IS necessary. Early stage startups can only afford to pursue the challenges that are necessary. By avoiding certain obstacles, entrepreneurs can be tough and strong on other trials that inevitably pop up.

Being able to find the path of least resistance is a crucial trait. This is true for the entire leadership team. Use the tech that will help scale fastest. Find the pivot that has the least barriers to entry. Find the roll-out plan that will grow fastest with the lowest acquisition costs. Leaders need to have a 6th sense for the right path to choose.

Toughness the Studio:
As a CEO of a startup Studio, I’m very focused on evaluating the toughness of our leadership teams. At Boulder BITS we focus on minimizing the obstacles for our co-founders. But, there is no entrepreneurial path that is easy. Because of this, we build teams that are passionate about their customer’s needs. This creates the foundation for toughness. We also challenge our teams to evaluate how they respond. Do they pull together and stand up to the challenge? Or do they shy away? Do they work harder for each other? Do they follow the path of least resistance? We only form and fund startups when a hard-as-nails team is aligned with the path of least resistance towards a scalable goal.


Fun Bits:

  • Some of the best traits to have as a leader are to have confidence, communication, commitment, positive attitude, creativity, and intuition. –Forbes 
  • It’s extremely important to have passion as a leader, if your having trouble finding it try pumping up your creativity, talk about your dreams, do what interests you most, or try practicing being mindful. –Marthe
  • Some of the best ways to lead a team is to: lead by example, be personable, stress your companies purpose, push the team’s limits, encourage personal growth, and to be accessible. –Jonathan Long




Author: Jesse Lawrence

Founder and CEO of Boulder Bits. Sci-fi lover, game theory strategist, and idea generator.

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