Thinking about starting a business? Think twice.

I made one of the most difficult decisions of my career last September when I decided to leave the company I helped start, Roniin (now Builders VC). It was made especially difficult by the amazing people I was working with, the great companies we started, and the momentum in our sails. It certainly wasn’t easy, and I continue to admire and respect my colleagues and the great work they are doing there. But in the end, I knew it was best for me to pave my own path. I needed to create a vision for making the world a better place and manifest it into something real and tangible. And as I embark further into this journey (in case you are wondering, I’m launching something that helps companies engage & inspire their employees through experiences that change the world. It’s still fairly stealth, but if you are interested in learning more, shoot me a note), I decided to take a moment and reflect on all the reasons not to start something new. At a time when technological advances make it easier than ever start a business, and when the cost to launch one is so comparatively low, it seems more attractive than ever to start a company. Yet unless you’re certain of certain things, you shouldn’t.

You shouldn't unless you care deeply about solving this one particular problem. When you start with a problem that you can’t imagine not solving, you’ll do anything to make sure it’s successful. That might mean failing a thousand times until you get it right. When push comes to shove, and when everything seems to be falling apart, you persevere because you know how important it is to solve this problem. Of course, the product may change, and the mechanism for solving this issue will evolve, but you never stray from your purpose. It has to start with a deep appreciation for solving this problem and doing everything you can to overcome the challenges. Deep down, you couldn’t imagine doing anything else. So unless you know the problem you want to solve and a burning desire to keep going until you’re successful, don’t start a business.

You shouldn’t unless you are ready to go through some of the most difficult times of your life. It’s not sexy, it’s not always fun, you may see your family or friends less, and you’ll definitely lose some sleep. Launching and growing a startup will be extremely trying. It takes discipline, grit, and commitment. If you aren't ready for that, you have no business starting a business. Don’t get me wrong -- being involved in a startup can be extremely rewarding. It can open doors you never thought existed. But that’s not the default setting, it doesn’t automatically happen. You have to approach it from the right state of mind. A state of mind that understands things won’t always go right, and that most days will feel like a roller coaster. So unless you at least acknowledge this, and approach it with the right attitude with the willpower and perseverance to overcome any obstacle, don’t start a business.

You shouldn’t unless you are ready to work on something that will stand the test of time. This should be one of the biggest commitments of your life. It should be something that you think of day and night and care so passionately about that you can’t imagine doing anything else. I’ve had too many conversations with people recently who want to start a business for the wrong reason. Don’t start a business with the motive to sell it in 2 years for a billion dollars. You are guaranteed to fail if that’s the thinking from the beginning. The objective of starting a business should be to create something that will stand the test of time -- something your kids will appreciate, and their kids will appreciate. If you are lucky, you’ll get to work on it the rest of your life, or at least a good portion of it. So unless you are ready to build something that will be around for the next 100 years, don’t.

You shouldn’t unless you have the confidence to do it better than everyone else. If you have an idea, there’s a good likelihood that someone else is already working on it. Very few companies are first to market. Facebook, Google, Spotify, Zappos weren’t first to market. They just out-executed. Being able to show market understanding, and demonstrating that you are uniquely situated to solve your problem, with a team that has a tremendous depth and commitment, is essential in building an amazing company. So unless you have this, or at least have the willpower to learn it & cultivate it, don’t start a business. 

You shouldn’t unless you’d still want to be doing it even if there was no money in it. Because there won’t be.... at least early on. Unless you are extremely fortunate or have a great track record, you’ll be working for basically nothing. Even as the company grows (or raises money), there probably won’t be a ton of money in it until there is some sort of exit or profitable hockey stick growth. So don’t start a company because you want to get wealthy -- in most cases, you won’t for many years. 

If, at the end of the day, you can say there is a problem you are passionate about solving, that you are uniquely situated to solve it, you want it to be around to stand the test of time, and you are willing to persevere through numerous hurdles and challenges for little to no money, then by all means, don’t hesitate. Start. In fact, you have no excuse. If you can say these things, then it’s time to stop talking about starting a company, and it’s time to do it. Your future self will thank you. I certainly hope mine will.

Why Failing Is Required

The best entrepreneurs I know are the ones that have failed the most. It’s been said plenty of times, of course, but it bears repeating -- failure, in a way that nothing else can, motivates the best to do their best. It’s in the avoidance of failure, and in the mere act of it, that we can we learn more about ourselves than anywhere else.

Obviously, no one aspires to fail. You don’t start a new business or product feature with the goal of not finishing it. And although many talk about the virtues of failing, what’s often overlooked is the importance of taking the kind of risks that often result in failure. If you never fail, or at least come close to it, then you aren’t on track to succeed. Sometimes, you’ve got to get booed off the stage enough times before you can successfully stand on it. If you allow yourself to accept that initial failure and never try again, you aren’t ever going to succeed, no matter what your definition of success is.  

Success starts by having your own positive attitude towards failure. It’s one of the most important things you can do as an entrepreneur (or, really, anyone). It’s hard to fall flat on your face, dust yourself off, and get back up again... only to fall flat on your face yet again. But having an insatiable, undefeatable attitude towards your failures can make all the difference in the world. The moment you start to approach failure as a positive, is the moment you start taking enough risks to become successful. I love working with startups for this reason. Only with a positive attitude towards our setbacks are we able to build something great and hopefully become remarkable people in the process.

I’m reminded of a story that took place during my early days at Lightbank when we invested in a first-time entrepreneur. Everything that could go wrong for the company did: customers weren’t buying, employees weren’t staying, money was running out, and spirits were sinking low. Like so many struggling entrepreneurs before him, he could have given up, succumbed to life’s hecklers and stepped off the stage. Instead, he persevered through the difficult times, kept a positive attitude through the failures, continued to take necessary risks, and led the company to an eventual acquisition (certainly not the definition of success, but a healthy outcome for the company nonetheless). The company failed so many times that it finally learned how to succeed.

We all fail at some point. Entrepreneurs probably more than others (a 90% startup failure rate almost guarantees this), but it’s imperative that we see our setbacks as building blocks and necessary steps toward any successful endeavor. When you peel back the layers of any great story, you’ll see hundreds of small failures stacked together to create the whole of one’s success. So take risks. Learn how to fail and appreciate failure. Maybe something good will come from it.

A Fleeting Thought

Life is fleeting. It’s unrelentingly brief. Every interaction, every conversation, every laugh, and every moment passes much too quickly. And just when we think we have time, when we feel things might be slowing down - everything can change in the blink of an eye, when you least expect it. 
I least expected it in high school, when I learned my older brother and idol, who got involved with the wrong crowd, would be locked up for the next 10 years of his life. Very suddenly, he was out of my life, and seeing him face to face meant driving 3 hours to a maximum security prison. Someone I saw every day, someone I learned so much from, and someone who taught me right from wrong, even if he didn’t know it, was locked up - our interactions reduced to mere letters and staged prison photographs. It hurt at the time, but it in a way I didn’t expect, it actually made us closer, and made me appreciate the time I did get to spend with him. 

It seems life throws things at us sometimes just to remind us how fleeting it can be. This again occurred more recently in one of the most tragic way possible, when a friend and former colleague, Adam London, passed away at the age of 27. In the days after Adam passed, the major recurring theme I kept hearing was how fleeting life can be. And it really is. Everything great can be taken away literally overnight. It’s not fair, and it doesn’t make sense. My only wish is that I had gotten to know him better, and everyone that knew him certainly wished they had more time to spend with him. But it also made me appreciate the interactions we did have and honor him in ways I would have never done otherwise. I had lunch with him a couple weeks before he passed, when his whole life was still in front of him, and everything seemed right. Then everything changed in the blink of an eye. 
You can try to make sense of things, you can try to rationalize and justify why things happen, but in the end, it’s sometimes impossible. All you have are the fleeting moments in front of you. This is why it’s so utterly important to make the most of it. Every interaction, every conversation, every laugh & every moment. You have to enjoy it. You have to embrace it. Even the boring, mundane and frustrating moments, you have to at least try to see the good in it. For you never know when it will pass. As the late David Foster Wallace said - it can be within “your power to experience a crowded, loud, slow, consumer hell-type situation as not only meaningful, but sacred; on fire with the same force that lit the stars: compassion, love, the sub-surface unity of all things.”
These fleeting moments, both good and bad, makes life so genuine. Understanding and realizing the delicate nature of life makes one optimize the time we have on things we enjoy. There are certain moments in life that make it clear that spending time on what matters, matters.  

These aren’t universal, and these platitudes are simply my own, but I know there are certain things I can do to optimize the moments I have:

Spend more time with those you care deeply about. Tell your parents you love them. Spend less time complaining and more time enjoying. Say please and thank you. Don’t be afraid to ask questions. Smile. Don’t take anything for granted. Read something. Play board games. Laugh. Give compliments to people you don’t know. Spend money on the experiences that make you happy. Send flowers. Spend time with your dog(s). Volunteer. Listen to music that makes you happy. Set a morning routine. Learn to play the guitar. Workout. Stay organized and set daily goals. Don’t be late. Keep your phone out of sight at dinner. Go surfing. Spend less time hungover. Laugh at jokes that aren’t funny. Eat food you normally wouldn’t try. Eat every breakfast sandwich you can get your hands on. Stay in touch. Don’t get distracted. Write. Do yoga. Meditate. Spend less time watching shitty TV. Spend more time watching documentaries (and Pixar movies). Unplug. Go on more walks. Take time to do nothing but think. As much as possible, help others. Buy food for the homeless and get to know their name. Integrate a charitable cause, somehow, someway, into your everyday work. Give high-fives. Spend more time face-to-face. Travel. Gain new perspectives. Go vegetarian for a month. Write a blog post because your best friends challenge you to do it.

I certainly have a long way to go to get there, but these fleeting moments are all we have, and what makes life so powerful.