Shot in lisbon, from atop a 300 ft monument, this man cast his shadow over the world. The shot has always inspired me to do something great.

Entrepreneurship Survival Guide

Thirty-one things I’ve learned so far

The idea for Mizzen+Main came to me nearly eight years ago.

The first real effort began two years ago. It’s been the longest two years of my life, and I feel like more has happened since I began product development than in the six years leading up to it. The easy part was the idea — a moisture wicking, wrinkle free dress shirt made here in America. The hard part is everything else. Here are thirty-one things I’ve learned since taking a crazy idea and turning it into what will be the next great American brand. Consider this a list of things to “pack” on your journey.

Disclaimer: These are lessons and thoughts from my experience. Have I figured this all out? Do I get it all right? Of course not. You should laugh at anyone that says they do.


  1. A sense of purpose. Do not set out on this journey without a larger understanding of why you are doing so. The hard times will almost certainly break you if you cannot keep your eyes on the “why” that drives you. If it’s making a ton of money, well, good luck. Let me know how many entrepreneurs that worked out for. Sure, you may get lucky just trying to make a lot of money. I wish you the best if that’s your strategy. Your chances are infinitely higher walking into a Vegas casino.
  2. Family. Plain and simple, you cannot survive this journey without family. My wife is the reason I’m still sane and my source of happiness and fulfillment on a daily basis, regardless of the ups and downs this absurd roller coaster brings my way. My parents’ never-ending belief in my pursuit and initial angel investment has gotten us to where we are now on top of life’s savings and our team’s efforts. Don’t have a traditional family? That’s fine — find a family that fits your life’s circumstances. Family can take many forms. Find one that will be there for you in your darkest moments.
  3. An incredibly supportive spouse. Or being incredibly single. Starting a company can be one of the most selfish acts you’ll ever do (not sure just how selfish you are…) You’ll invest everything you have and sometimes more. You’ll be foregoing nice things, vacations, amazing dinners and nights out on the town, attention your partner deserves, and so much more. Don’t ever let your spouse think you do not appreciate everything they enable you to do. You will, trust me, but strive to never have that be the case.
  4. The right partners. You cannot do it alone. Do not try alone. You almost certainly cannot do it with the wrong partners. Your cofounders will be the reason you succeed or fail. They will be your thought leaders and bring your idea and company to new heights.
  5. Great friends. Friends are a lifeblood, whether you’re starting a company or not, but especially if you’re starting a company. They’ll be there to help throw your launch party. They’ll be early evangelists. They’ll be there when you need to escape for a bit and just have a cold one. If they don’t support you, they aren’t your friends. If they support you only once you’ve made it, they were never your friends.
  6. An ego that balances confidence and humility. You must be your greatest advocate and put yourself out there. All. The. Time. Make sure, however, that you don’t lose your humility. It’s painful to watch entrepreneurs, at any stage of their journey, who have lost any sense of humility. It’s a necessary balance. Few get it right.
  7. Fitness and health. You cannot grind day in and day out if you are not healthy. That means physically and mentally. That means both fitness and diet. Take care of yourself or you won’t be able to take care of your company. I’d recommend CrossFit for all of the above.
  8. Perspective. Not everyone thinks like you. Remember that.
  9. Reality checks. It’s never as great or as terrible as you think it is.
  10. Ability to ignore reality. If you can’t ignore reality, you won’t even start your journey.
  11. Adequate savings. It will likely take everything you have and more. No one funds an entrepreneur and an idea. No one. If they do, both they and you will almost certainly lose everything.
  12. A plan. As crazy as it sounds, people undertake this journey without a real plan. Of course your plan won’t work out exactly as you expect. A ship does not stay on course at every moment. Waves push it around, storms may require a change of direction, and unforeseen circumstances may require drastic changes, but a ship must chart a course before leaving the harbor or it will never reach its destination. Understand your needs, from basic product development and general business strategy to finances and marketing, and make a plan.
  13. Adaptability to pivot 18,342 times. Before lunch. Things happen. Some of these things may be in your control, most are not. Ensure that you, and your team, are adaptable enough to find a way to keep moving forward, regardless of the obstacles. A rigidity or unwillingness to change course when necessary will likely doom your effort, whether it’s quickly or over the longer term.
  14. A social presence. It’s 2013. It’s far past time to have a meaningful presence on social media.There is just no excuse not to. If you think “no one cares what I had for breakfast, why do I need to be on Twitter?” then you have such a significant misunderstanding of social media, you may need address it before moving forward at all. To be clear, you do not need to be on every social network. If you’re going to pick, pick two: Twitter and whatever network is most relevant to your business.
  15. A physical presence. Big on social media? That’s great. Does anyone in your town know who you are or what you’re working on? A truly effective social media presence is a rare thing. Equally rare is a powerful and meaningful real world presence offline. Side note: both a social and physical presence are anything but built quickly. It takes a tremendous amount of time and effort unless you are a celebrity (instant influence) or incredibly rich and can throw a lot of parties and easily buy influence. Even then, to be effective, it’s still a fair bit of work.
  16. Gratitude. Find a way to be grateful, for everything. Ok, you don’t have to love the obnoxious driver who cut you off yesterday, but living your life with a sense of gratitude for life’s blessings, large and small, will have a profoundly positive impact on everything you do. I promise.
  17. Patience. This goes without saying. If you cannot be patient, you will lose your mind starting a business. Things go wrong, all the time. If you lose your head when something goes wrong, you immediately become ineffective, waste precious energy, and add stress in your life and those lives around you, thus weakening your ability to respond.
  18. Strength when necessary. When someone wrongs you or attempts to undermine your business, sometimes it’s not worth the energy or repercussions of responding, at all. Still, at times, you will have to respond, powerfully, in order to protect what you are building and ensure it does not happen again, from that offender or others. A mentor of mine early on in his 60+ year career made it a point to destroy anyone that intentionally wronged him and his business. Word spread soon enough not to cross him, even in a small way. This strategy may not work for you. He regularly spends more on attorney fees than the amount of the offense, but the lesson is clear to any would be offenders.
  19. A sense of humor. Laughter may or may not be the best medicine, but it is incredibly helpful in what is a very difficult journey. Find ways to laugh often. On your own. With family and friends. At yourself. Just be sure to laugh.
  20. Ridiculous optimism.
  21. Ability to shut down. Brains need rest. You must find time to shut it all down for a bit, spend time with your loved ones, relax, and come back better than before. Find a little time each day to recharge.
  22. A commitment to give back. It’s not all about you. Find a deserving cause and endeavor to make a real impact.
  23. An awareness of world affairs. You don’t live in a vacuum. Understand the changes in the world around you to be better prepared for later this year and later this decade. Nothing is immune from global changes.
  24. The gift of gab. The ability to talk and connect with others is invaluable. Warning: it takes practice.
  25. The ability to stay silent. Effective communication also includes silence. Know when to use it. Observe others. Learn from those around you. You cannot learn anything while talking. Warning: this also take practice… and is harder.
  26. Mentors. The wisdom you can gain from those who have gone before you is invaluable. Seek out mentors, put in the work to learn from them, and make sure they understand how much you appreciate anything they offer, most especially their time.
  27. Personal hygiene and appearance. I really shouldn’t even have to mention this, but time and time again, people prove that they need to be reminded to brush their teeth, take a shower, and use deodorant. Seriously. If you don’t look the part, why should anyone believe in you?
  28. An understanding that never give up may mean change course to reach your desired outcome. Some joke the definition of insanity is doing the same thing over and over again and expecting a different result. Determination is necessary. The intelligence to recognize you may need to adjust your plan of attack is even more important. Of course this doesn’t mean give up — just find a better way.
  29. Attention to detail. The details may not matter to you, but they do to your partners, suppliers, and customers.
  30. Speed and acceptance of failure. True, details matter, but do not drown in the minutiae and refuse to move forward to ensure that every single element is absolutely perfect. You’ll never get anywhere. I’d recommend reading the Lean Startup, whether you are an entrepeneur or not.
  31. Perseverance. No entrepreneur, no business, no athlete, no person has ever succeeded at anything, without an unhealthy level of perseverance. The quote below is a beautiful summary of the main reason entrepeneurs succeed against the odds and why other “virtues” fall short. Perseverance is interchangeable with persistence and means “steadfastness in doing something despite difficulty or delay in achieving success.” In the end, this is what it all comes down to.
“Nothing in the world can take the place of persistence. Talent will not; nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not; the world is full of educated derelicts. Persistence and determination alone are omnipotent. The slogan ‘Press On!’ has solved and always will solve the problems of the human race.” Calvin Coolidge

The road ahead. Western Australian Outback.