Category Archives: Motivation

My Biggest Mistakes – What I Wish I knew as a New Entrepreneur

Before Ukulele Underground took off, I had failed many many times in business. Each of these failures took a huge toll on me emotionally and psychologically. My ego was crushed every single time. When you fail in business, its hard not to equate it to just you being a failure. You begin to question your self worth. “Can I even do this? Or am I always going to be a failure.” You think about how embarrassing it is not only for yourself, but for your family and people who associate with you.

It took me a long time, years in fact, before I was comfortable enough with myself and my ego had recovered enough to look back at my failed ventures and try to figure out where I went wrong. I found a lot of mistakes and before starting Ukulele Underground I promised myself I would not commit these mistakes again. If you’re just starting out in business, or if you’re struggling like I was for so long, please please please not only read the following but apply them to your life and business. It will exponentially increase your chances for success. I know it did for me.


My biggest business mistakes from my past failed businesses

1. I didn’t honestly give it my all. – I wasted a lot of time when I should have been working. In my early 20s I played a lot of video games, went out a lot, didn’t spend a lot of time working on the business and it showed. Your effort is one of the few things in business you can control 100% so don’t waste it. There are so many more things you can’t control at all so maximize your effort. Do everything you can (legally) to make your business succeed no matter how daunting it may seem.

2. I thought because I was smart, I didn’t have to work as hard. – Hustle > Smarts. every time. period. If you’re like I was and think because you’re smart you will have an easier time in business think again. Success in business belongs to people who are willing to hustle. To work as long as it takes to get the job done. I would often see people who I thought I was better than having more success than me and this used to make me jealous and jaded until I realized that hustle beats smarts and skill every single time. If you are truly smart bring hustle to your game and you can become unstoppable.

3. My ego was too big. I didn’t know enough but was too ashamed to admit it. – I made a lot of mistakes early on because of my ego. Starting out in business is pretty scary as there are a lot of new things you need to learn very quickly. I made a lot of mistakes, some very costly ones, simply because I wouldn’t admit I didn’t know what I was doing. What I should have done, and what I do now is find people who have done what I want to do, then try to ask them for advice. It’s pretty foolish to think that your business is so unique that no one out there has faced the problems you’ve faced. More often than not, you can find someone who can help you along and get you to the next step. Don’t let your ego get in the way. Ask for help.

4. I thought I could do everything myself. This goes hand in hand with the last one. Because I was ashamed to admit what I didn’t know, I tried to do everything myself. This takes time away from the important things. Things you should be focusing on to build the business. In the beginning you can get away with this and honestly probably should try to do as much as you can to save money, but there comes a point where you need to let go and put certain tasks into the hands of more experienced and talented people. When the time is right, ask someone you respect for referrals to help offload work that is taking up time that you should be using to focus on building the business.

5. I wasted a lot of money. Treat money sacredly. This again goes back to ego. When I started my first business, my grandma gave me $5000 to get it off the ground. I spent it all on stupid stuff and it was all gone before I knew it. That company never made a cent. $5000 may not sound like a lot of money, especially to people who are out looking for funding, but every dollar should be treated as sacred. That experience is probably why I am such an advocate of bootstrapping. It’s easy to spend and waste a lot of money. Money is the easiest, laziest, and least efficient way to solve problems. With Ukulele Underground, we purposely started with just $300 to make sure we didn’t have any money to waste. We had to use our brains and brawn to make things happen. I am so proud of the creative solutions for problems we figured out on a shoe string budget in the early years. We learned to be efficient with capital and make every dollar grow. Even today, we still operate the entire business for a little over 10% of our total gross income. And that is something I am very proud of.

6. I built things nobody really wanted – No matter how cool you think something is, if nobody wants it you don’t have a business, you have a project. If you’re going to be in business, you need to solve other people’s problems, not just do cool things, or think about solving your own (money) problems. Entrepreneurs solve problems for money. If you want to be an entrepreneur solve problems.

7. I always gave up – This was the biggest revelation to me and what finally go me from failure to success. Whenever things got a little rough or tight in my past businesses I gave up. Business is not easy. You’ll often hear the saying that, “it’s a marathon not a sprint” and its very true. You need to be in it for the long haul. There are many roadblocks, broken bridges, and pitfalls on the path to success. There will be many things that will seem unfair, that you feel should not happen. You will feel cheated at times, and you will be frustrated by the lack of progress. Deal with it. Keep pushing towards your goals. It took us with Ukulele Underground years before we made enough money to be even considered middle class. We lived on well below minimum wage income for a few years before we broke through. Did it suck? Hell yes it sucked, but we didn’t quit (even though I wanted to at certain points). Even though I started out this post by saying I failed many times, in truth I didn’t. In all of my past businesses I gave up. I gave up many times because things got a little bumpy. The only difference between UU and all my “failures” is that this time I didn’t give up. Don’t give up.


The “Right Plan” Letter

I originally wrote this letter to give out at a college and career fair at my old high school. Due to scheduling conflicts, I was not able to attend to hand this letter out to the seniors there. It may have been for the best as it’s probably not something the teachers would want the kids reading.


Dear __________________

You may read this letter now, but you probably won’t think much of it. It’s just some piece of paper some old guy handed you at the career fair at school. Getting a job, starting a career, or any of that boring stuff may be the last thing on your mind right now and that’s cool. You’re young and should enjoy being young. All I ask is that, if you think this letter is boring, stop reading it, but please don’t throw it away. Just put it somewhere in your house where you know you will be able to find it. A year later, 2 years later, 5 years later. Whenever that time is when you have to think about starting your real life, find this letter and read it.

There’s this concept of the “right plan” that most adults will try to convince you to do. Go to school. Study Hard. Go to college. Study hard. Get a job. Work hard. Get promoted. Rinse. Repeat. Retire. Ride off into the sunset. Sound familiar? How many people do you know personally who followed this plan? Your mom, your dad? Maybe your older brother, sister or cousin is in the process of following this plan. Of those people how many of them do you think are frustrated with life? Hate their job? How many of them complain about work constantly or maybe people that they work with. How many of them wish they didn’t have to work but feel they have to? How many of them feel stuck. How many of them are waiting for retirement. This is the result of following the “right plan”. This plan is full of crap.

This plan is full of crap because it tries to make you believe that life is about reaching a destination. Get a job! Hooray you made it!

Then reality sinks in.

You realize that this is not the finish line you were hoping for. You get upset. You feel cheated. You feel lied to. You followed the plan, you did everything you were supposed to. You’ve “arrived” and yet this is nothing like what they promised. You’re frustrated but you don’t really know why. This is what causes mid-life crises. This plan was a hoax.

Now, I’m not saying the “right plan” is the worse plan. There are far worse ways to live your life than the “right plan”. I’m just saying that what it promises is a lie and nowhere near the best plan. There are much better plans available. Like the one I’ll propose in this letter.

The “right plan” is full of crap because in reality, life is NOT about the destination. Life is about the journey. The point of life is to gain experiences, make mistakes, learn from your mistakes, become a better person and try your best to make your life one that brought value to the world. When you bring value to the world, you create meaning in your life. By bringing value to the world, your life has a purpose. You’re no longer just existing, now you are living!

So how do you make your life one that brings value to the world? 

Well the first step is to get to know yourself. Try to truly understand yourself. What are your strengths, weaknesses, what brings you true joy and happiness, what pisses you off that you want to change / need to change, what brings fulfillment to your life. Self discovery is something very few people do, yet understanding yourself is the first true step in becoming an asset to the world. By understanding your strengths, your passions, what truly makes you happy deep down inside, you can focus on those things and those things alone. You can take a stance and choose a direction. Some people refer to this as “Finding your Calling”. Most people who follow the “right plan” never do this and live their whole lives without discovering what could have truly make them happy and fulfilled.

The second step is once you discover what you truly want to do, to put yourself into positions where it is possible to fail. Anything worth doing in life usually comes with the chance of failure. Success and failure are yin and yang and chances for each usually grow proportionally.  Most people are terrified of failing. So terrified, that they forfeit their opportunity to achieve true happiness in an attempt to completely avoid failure. I am not saying that failing is great. It is terrible. It sucks to fail, but you should never let the fear of failure deter you from the possibility of achieving something you truly want. You cannot hit a home run without swinging the bat. You may strike out, but living with regret that you never took a swing is much, much worse.

Step three is to persevere. Don’t give up. Trying to do anything worth while always comes with adversity. Creating anything that makes a difference in the world does not happen over night. You WILL fail. It is inevitable. The important thing is to always, always get back up.  Learn to appreciate the process of growth, this includes failure. There is tremendous value if you can learn from your mistakes.

Most people will quit after failing once. “Quit while you’re ahead…” They’ll say. Bullsh*t. How are you ahead? Did you accomplish anything by giving up so fast? Most likely not. The funny thing about life is, people tend to forget about all your failures if you end up succeeding. Do people remember the Wright brothers as those guys who crashed a bunch of times? No. They remember them as the first people who flew in an airplane. Do people remember Mark Zuckerberg’s 3 or 4 other failed projects before Facebook? Persevere. People will only remember you as a failure if you give up. Never let a failure be the last thing you do.

I hope this letter will help you in your life’s journey. We all have the choice of how we want to spend our years on earth. You have the choice to live or to exist, to bring value to the world, or take value from it. It’s up to you if you want to have a life filled with fulfillment and purpose or one that is not. It truly is up to you and don’t ever let anyone and their “right plan” tell you otherwise.

Kauai Tech Startup Group

I was fortunate to be flown to Oahu to last month to attend a software industry skills development panel. It was a great experience as I got to meet a lot of people who are passionate about the same things as me; entrepreneurship, tech startups, developing a software based industry to transition Hawaii away from its heavy dependence on tourism (which I personally have a long standing beef with).  It sadly was the first time I had experienced that in Hawaii.

During the event I got to hear all the exciting things that are developing on Oahu and Maui and I have to admit it got me a little jealous. Hackerspaces, Meetups, Conferences, just the ability to easily meet up with and hang out with like minded people, that’s something I’ve wanted since we started UU 3 years ago that Kauai really does not have. Though Hawaii as a whole is still very far away from becoming a geek hub like San Francisco, Seattle, Boulder or Austin; Oahu and Maui seem to be taking steps in the right direction while Kauai… well ignorance is part of its charm.

After exchanging some emails with Russel Cheng, I’ve decided that if no one else is going to hold the flag for Kauai, I’m going to have to so I’ve decided to start a monthly Kauai Tech group.

The mission of the group is simple. To help culture the tech (Web Ap, SaaS, mobile ap, interactive content) scene on Kauai and develop a true startup culture here on the island.

The monthly meet ups would be a way for like minded people to get together and share their projects, get feedback and help each other grow their businesses. On an island where the only thing you do with computers is IT (at least according to most here); finding people might be a little difficult but I think I can wrangle 5 or 6 people together for a test run. It might take a while to get traction but like any venture the most important thing is to start. Will keep everyone updated on the progress as we work towards our first meet up.

The Fear of Failure

Something strange happens as we grow older; we become deathly afraid of failure. Though brought into this world fearless, we’re conditioned over time that failure is bad, failure is something to be avoided at all cost, that failure can be avoided if you “just do your homework”. This fear often prevents us from doing the things we always wanted to do. We may get very excited about something yet after spending a little time talking to others, and doing our homework, we convince ourselves that it wasn’t such a great idea, or that we can’t do it for whatever reason; we aren’t good enough, not smart enough, don’t have enough money, don’t have the connections to make it work. Excuses are always an easy way to say, “I wouldn’t have failed if _______ hadn’t ________.” Even worse is those who try and stumble and refuse to try again.

This whole concept is completely contrary to the best way to learn anything. NOBODY is an expert when they start. The best way to learn, is to do. If you fail, you get back up, learn from your mistakes and try again. Its the process of doing, failing, and trying again that creates real world expertise.

Don’t be afraid of failure. Conquer the fear and try to fail in the most spectacular way possible. Most importantly, when you do fail, get back up and try again. The path to success is comes with scraped knees.

I’m going to start an interview podcast

I’ve been tossing around an idea in my head for a while to create something that will help inspire and guide a new generation of entrepreneurs, artists, and movement leaders. Inspired by the work done by Andrew Warner at and Jason Calacanis at This Week in Startups, I want to start interviewing entrepreneurs who’s ventures were built on passion.

I hope to accomplish a few things by doing these interviews:

  1. I want to champion the idea of pursuing your dreams and following your passion. If you choose to pursue your passion, you will probably bring more value to the world than if you didn’t. Money is how the world tells you that you are bringing value to it. Follow your passion and you will be rewarded. Its so ironic that the people we idolize are the ones who are doing what they love, yet our whole lives we are constantly discouraged from doing so. I want more people to realize this fact.
  2. I want to inspire people to start something. I want to show them that they can do it. That they are smart enough and will succeed if they are willing to work hard. It is especially important to me that the youth of Kauai realize that with the internet, they have all the same opportunities that anyone else in the world has. Nothing is impossible anymore. Everyone has a shot. It’s up to you to take it.
  3. I want to learn from these people about how to grow my own businesses. What I could be doing better and some of the hurdles any successful person must fight through and overcome. I’ve made a lot of mistakes in business and I’m sure many could have been prevented by learning from those who have been through it before. I also think by listening to those who have done it before, I can pick up some new idea on how to grow my own business.

If you have any suggestions on who you would like me to interview, please post them in the comments below and I will take a look and try to get them on. I will probably start close to home and with people that are accessible to me.


Gary Vaynerchuk Web 2.0 Expo Keynote

Gary was (and still is!) a big inspiration to me when I was stuck in a rut late 2007 trying to figure out why I was so miserable and what I should do with my life. His passion for life showed me that there was absolutely no reason I should do anything that I did not love. The more I hear him speak or read things he’s done it just gets me fired up all over again.

For the uninitiated, Gary Vaynerchuk is the Director of Operations at Wine Library, a retail wine and liquor shop based in New Jersey and the creator of Wine Library TV, one of the hottest video blogs on the internet.  He is quickly “changing the wine world” with his unique approach to wine and how you enjoy it. While in middle school he had a lucrative trading card business, pulling in $1000 every week at card shows, only to be forced to give it up and  work in the family business, a liquor store, for $2/hour. In his early 20s, he grew that liquor store into Wine Library, a $50M retail company and one of the largest independent liquor distributors in the United States. Upon turning 30, in his own words, “he freaked out” and began doing Wine Library TV which has lead him to appearances on Late Night with Conan O’brien, Ellen, The Big Idea, and Mad Money.

He is a strong believer in finding your passion and executing on it. His approach to business of passion first, is a concept that has resonated strongly with me and lead me to eventually leaving my job to dedicate more of my time to my companies. A decision which I do not for a second regret.