Why some can, and why some can’t

“Those who cannot govern themselves are condemned to forever seek others to govern them” – Steven Pressfield

I recently read (listened) to ‘The War of Art
‘ by Steven Pressfield. Great book, filled with a myriad of great quotes like the one above but the one above really stuck with me. Since I began trying to start businesses as an adult 10 years ago, I’ve spent a lot of time trying to put my finger on what separates those who are successful as entrepreneurs and those who aren’t. The stats are there, 9 out of 10 businesses fail. So what separates the winners from losers? I’ve realized long ago that anyone can do what entrepreneurs do, but at the same time, not everyone can. Why?

Why can some people start a business and go on to have success while someone else with the exact same credentials fizzle out jaded and emotionally scarred? Upon reading ‘The War of Art’, specifically that line it all became pretty clear.

The entrepreneurs who make it, have learned to govern themselves and the ones who don’t never did.

Since we’re thrown into the school system just after we barely learn how to walk and talk, we’re taught to do as we’re told. Do as you’re told and you’re rewarded. However once you’re out of school, there isn’t anyone there telling you what to do anymore. So what do most people do?

They seek out new masters.

New people to tell them what to do. Governing your life is now scary because for 18-22 years, you’ve been pounded with the idea of “do as you’re told and you will be rewarded, don’t and you’re punished”.

No one ever teaches you to tell yourself what to do. And this is why some can do it and some can’t.

Because of this it’s easy to seek out a master, leave them the hard decisions and take no responsibility for the outcome. No matter what happens, it can always be master’s fault.

The normal person seeks out masters, and this is why normal people will fail at business. I’ve said it before, business is the ultimate form of self expression. You get to bring an idea, something that exists nowhere in the physical world and turn it into a real creation of your own design. Self expression, not an expression of ideas and input from others. If you run a business, you call the shots, you accept your defeat and you claim your glory. Win our lose, whatever the outcome, it’s because of you.

Self governance is the hardest thing to do and I don’t think its something you can ever truly master. It’s something you battle with every day. Even people who own businesses, myself included battle for this hallowed ground daily. The temptation to put hard decisions on someone else is so tempting, what do the lawyers, accountants, consultants, mentors say? It’s so much easier to do that, often times they may be right, but it should never displace your personal instincts.

Those who learn this win the ultimate prize, freedom, and those who don’t will not even know what freedom looks like.

Well That Escalated Quickly…


I am honestly quite shocked with the amount of people who took the time to read my diatribe on the Hawaii tech startup scene. To me, it was just an off the cuff outlet of the frustrations I’ve had from working in this industry locally for close to 10 years. I expected close to no one to read it as the case with most of my posts on my blog. I’m humbled and grateful to everyone who took the time to read it and passed it along.

While I regret that blog post may have been the first introduction I’ve had to many of you (not my best look), I’m actually happy that it started the discussion that it did. In addition to some comments saying I was out of touch or off base, I received many emails from people that basically summed up to “Thank you, finally somebody said something” or “This is the same discussions I’ve been having in private for years.” The fact that people came out so passionately on both sides of the argument; that equal amounts of people thought i was a complete moron or someone speaking the silent truth was surprising and enlightening to me as to how many others view what I am seeing.

There are a few people I feel I should acknowledge who brought up some very valid points which have helped me gain a better feeling towards the ecosystem as a whole.

Eric Nakagawa is a guy I’ve known for a long time. I first met him around 2005 at my first job right out of college and even with all his success he has been and still is just a really good dude. He made a great point that I could do more

I whole heartedly agree. It’s so easy for me to take my shots from the safety of Kauai. I am fortunate for things to have kind of worked out so far and I have a great life. Its easy to just sit back and essentially be a hater on people trying to do things. It’s not just easy its wrong. It makes me an asshole and a bully (something I’m trying to get away from). Taking shots, shining a light on things I think to be problems doesn’t actually do much of anything to address the issues.

So I’m working on something. Like everything I do, it’ll be a small start but I’m hoping to bring real value to people who want to learn how to build online businesses.

When I got started, I was fortunate to have some great mentors like my dad and other entrepreneurs I respect who built businesses off profits. But none were operating businesses like I was, so I struggled immensely. The problems internet entrepreneurs face are so different than brick and mortar or other types of businesses. Hell even the startup world of the late 90s is a vastly different game than today. I remember how tough it is to feel like the amount of things you don’t know but should know is just overwhelming. In fact I am still learning new things constantly. The learning never ends, but it should start with quality. There is so much information out there but how do you know what is legit and what is BS if you’ve never done this before? And trust me, there is a lot of BS out there.

So I’ll be setting up something to help bring quality mentoring at scale to up and coming entrepreneurs in Hawaii.

Eric has agreed to help and be one of the first to help with this cause so if you’re interested in learning from him please sign up for that mailing like to the right. I won’t spam I promise and I won’t be charging for it either. I’m doing it to help.

Also I’m grateful to Steve Markowitz for reminding me that we’re still early into developing the ecosystem here

The 221 tax credit which was a colossal failure to most people, was around 10 years ago and even if you count that as the first attempts to get the startup ecosystem in Hawaii off the ground, we still have 10+ years of work to do to really create the ecosystem we all want. On any journey worth attempting, mucking is required, and even though we may be mucking around right now eventually there will be a day where we’re out and on to the inevitable better days.

So once again, thank you to everyone who took the time to read my rant. Thank you for all the feedback. And thank you for challenging me to do more to help.

The Clownshow that is Hawaii’s Tech Scene

This post will probably rub a lot of people the wrong way. I don’t really care, because it needs to be said.

There is way too much celebration of mediocrity and non achievement in Hawaii’s tech entrepreneur scene. There are also too many (not all, but too many) frauds who have no idea what they are doing very vocally leading the charge. I get it, people have egos that need protecting but this isn’t high school or college. This is the real world. This is business, not fantasy startup land where everything comes easy and everything always works out. Here are my three biggest beefs (I have a lot of them, but I’ll spare you).

The “Acquisition”

I’ve seen it over and over again, people get “acquired” and the local media writes all about that shit. If you’ve ever run a real business for any substantial amount of time and take even just a few minutes to investigate the details, you can read between the lines and see the truth. These companies failed and are being bailed out by someone who doesn’t understand what is really going on or feels sorry for them. They are buying toxic assets. Maybe the media doesn’t understand? More likely they don’t care and are fine with rehashing press releases that sound cool.

Failure is part of business. 90% of businesses fail so I’m not condemning failure itself. I’ve personally failed a ton. But every time I did fail, I never expected anybody to tell me “Good job!” or “Congratulations!”. This congratulatory attitude towards failure is toxic and it is absolutely the LAST thing we need here if we want to build a sustainable ecosystem. You seed false hopes into future would be entrepreneurs and even worse, you set a standard of masqueraded failure as acceptable or even praise worthy.


I’ve written a whole post about it before, but it wasn’t aimed at anyone in particular. This time, I’m fire shots. Most tech investors / angels / VCs in Hawaii (the ones who are investing in Hawaii companies anyway) have absolutely no idea what they are doing. And it PAINS me, because these people are literally throwing money away. literally. And most of the time, it’s not even their money!

The facts are, 99% of funded startups fail (maybe this is why everybody celebrates the acqui-hire / bailout). The few that make it usually have a stacked deck in their favor. Yet for some reason people here that more funding is the answer.

Here the only investment in Hawaii that would make sense to me, and its not rocket surgery.

1. A company that is already showing major (and I mean major) traction pre angel round. They already have something built and running before asking for money. Their product / service has so much traction that their costs to operate (servers, apis, etc) are on the verge of killing them. I don’t understand why this isn’t common sense.

2. In the round of funding there are other legitimate investors who can leverage their connections to aid a startup with the areas they need the most help.   Not an entire round of dumb money.

3. This help should be majority connections and introductions and deal making to scale growth / profitability and movement into other verticals or markets. Investors should always offer more than money.

I do not see this shit happening with the tech startups in Hawaii. Instead I see people who have such a poor grasp of where the world is going investing in the things they can understand. Which by the way all happens to be things rooted in the past.

The (Want)”Entrepreneur”

The “entrepreneurs” are to blame as well. I see a perpetuation of the plantation mentality that people here have blamed for generations. Waiting for someone to give them approval to build their business. “We can’t build our company because we  can’t get funding…” “I need to find a technical co-founder”. If these things truly stop you from building your business, good, you’re not cut out for this line of work anyway.

For the ones who do get funding, congratulations, you made it to the starting line of the marathon. Now run! Funding gets you to the STARTING LINE. Why don’t people realize this. Getting funding means the real work is now to begin. Stop celebrating! Get to work!

To me this shows what the real problem is here, it’s not a lack of funding or opportunity, its a lack of real entrepreneurs in the tech sector (we have them in the tourism industry). There are a few that I have met that I think have built / can build real companies, but they are few and far between and most of them are bootstrappers like me and don’t issue press releases because they’re too busy serving their customers.

If we’re to truly build a sustainable tech / startup ecosystem in Hawaii, we need to be honest; publicly but more so with ourselves. Everyone, the entrepreneurs and the investors. We need to stop seeking out approval (funding) to build businesses. We need to stop celebrating failure. We need to stop being dumb with other people’s money. Show entrepreneurship for what it really is.


Entrepreneurship is not cool. It is hard and shitty a lot of the time. If you really want to do this, be prepared to sacrifice a lot of your life, your time, your friends, your ego, your pride.  It’s not for the weak willed. But for those who seek it, it’s the truest form of self expression available. Then maybe we’ll have the right people come out to grow this thing.

How to Make More Money

Anything that won’t sell, I don’t want to invent. Its sale is proof of utility, and utility is success.” – Thomas Edison

I think a lot of people have the wrong views on money and it’s one of the main reasons people have difficulty making money or even if they do manage make some money, are unhappy. I see this when people choose careers based on the salary they expect to receive or in others who do dumb or hurtful things to others just for the sake of making a dollar. It’s my goal in this post to help people gain a better understanding of what money really is and how it should be treated.

Continue reading…

You can Always Unquit


In 2005 I started and failed at my first business. I was a cocky, insecure 23 years old and it was called Island Music Network (see part of it via archive.org. I am face palming linking to this, I was so pathetic). It basically was a website that had no real business model that I spent a bunch of money on hiring people to film a few live performances for me. But at the time, I thought I would be retired in just a few years. I fell into the trap I think many first time entrepreneurs fall into. When we’re inexperienced, we read all the cool stories of quick success, and the lifestyles of successful entrepreneurs. We envision futures where we’re the ones telling our story to magazines and on TV. Of course it’ll happen, we’re geniuses right? Our ideas are awesome right?

Continue reading…


As an adult, I’ve come to learn the quickest way to insult, enrage, or quickly lose friends and make enemies, is to challenge someone’s ego. Challenge the perception of what that person believes themself to be.  This doesn’t even need to be done on purpose, it can even be done on accident and the effect is the same. The ironic thing is our egos are rarely, if ever accurate. What we think of ourselves is often not even close to reality. Need proof? Try and record yourself talking for 30 seconds, it’s NOT going to sound like what you think you sound like. You probably will hate it and that might make you a little irritated. The juxtaposition of ego and reality is never pleasant.

We create our egos because we as humans inherently long to be something. We WANT to be good at things, we WANT to be good people, we WANT to be smart, funny, charming, good looking, athletic, great singers, all these things we want. And if our ego is untouched, unchallenged, we can be those things.

But the moment someone shines a light on your ego, shows you how far it is from reality, that your are not that ripped athlete, or genius prodigy, super entrepreneur, genius marketer, or super model, and instead you’re the equivalent of that troll from Ernest Scared Stupid (seriously, that movie was the scariest thing i watched when I was 9) when compared to what you wanted to be, we get mad, upset, or hurt. We feel these things because our egos represent what we truly want to be and seeing that we are not what we thought we were is crushing.

Nothing hurts more than seeing the disparity between your ego and reality.

I know this is fact. So I try my hardest to keep my ego in check. I know am a D+ entrepreneur (at best). I had 6 businesses fail prior to Ukulele Underground. I’m not great at playing guitar, I don’t even know my scales. My voice is annoying (speaking and singing). I have very little patience. I’m often rude because of my terseness. I’m often really rude because if I find people uninteresting I cannot fake being interested. I’m not a people person. I have issues with my mother. I got shitty grades in college not only because I drank and partied a lot, but because I probably am not very smart as well. I suck at tennis. I suck at pretty much every video game I’ve ever played. In fact, I suck at pretty much everything I enjoy. As well as UU is doing, there are a ton of companies that are doing way better and they’re run by way smarter people. I’ve made a ton of bad deals. I’ve lost lots of money trying to make more money. I’ve made a ton of mistakes in the past. I’m embarrassed by many of my past actions.

I can go on and on with what I suck at and what is wrong with me, there are a few things I think I am ok at, but I’m not really great at anything. In fact, I’d be lucky to qualify as mediocre at anything. And thats OK. By definition we all can’t be extraordinary.

I asked my wife tonight what she thought of my hypothesis that the reason I have anxiety these days is because I’m not as delusional with my ego as I used to be. Maybe ego is necessary to deflect the harshness of reality and a more realistic ego is not healthy. Maybe I should pump my ego back up because I seem to get just as mad when I interact with people who can’t acknowledge their own egos. Who knows. All I’m hoping is that maybe if I can get my ego totally inline with reality one day, that I can finally cast it off  and be totally free of its burden. The burden of this imaginary thing that I created. Think about that,  the only one who agrees 100% with your egos is you.

In the end, our egos die with us, we’re remembered by our actions not what we thought we were.

I hope I don’t come off as depressed or anything in this post because I’m really not. I’m still laughing that I remembered Ernest Scared Stupid. This is just some random ramblings that was going on in my brain after a rough day. As mediocre as I am, I know that I got lucky and what I have going in my life right now is pretty amazing. Perhaps I should think about that more than ego, but  ego probably wouldn’t like it.

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.


Back from Japan, Ready to Crush it

A few months ago, I wrote a post about how I was feeling a little burnt out. The truth is, I wasn’t just a little burnt out at the time, I was extremely burnt out. So much so I think I was experiencing generalized anxiety.  I was worrying about everything, everyday, and totally unmotivated to continue to build my businesses. Luckily, my wife convinced me to take a vacation to Japan for a little over a week. This was actually the first vacation I’ve had in about 7 years. I’ve traveled a lot in the past 5 but it was always for work and left me more exhausted than refreshed. I always felt guilty of leaving the business for a vacation. I tried once last year, it was a miserable failure. I didn’t even understand why people traveled if that is what it left them feeling like. This trip was different. I was a nervous wreck on the airplane going over, and over 10 days, I regained my perspective on life and came back more refreshed than I’ve been in years.  My anxiety was gone, and has been gone for weeks (I’m still amazed at how much my life has improved from just 1 vacation). And more importantly, I am working harder in my businesses than I’ve worked in over a year. Here is what I wrote to my facebook when I returned about my experiences. It’s more casual than most of my blogs but it deserves to be here, for nothing else but to remind me that I need a vacation once in a while.

From Facebook:

Back from Japan. It was a truly spiritual experience for me. The last time I was there, I think I was just too young to truly appreciate the trip. This time was different. I was overwhelmed with two powerful feelings there. Being of Japanese descent, visiting Japan made  me so proud of my heritage. Everyone there seems to be honestly trying their best to perform their jobs to the best of their ability no matter their station in life. There was no complaining no matter if they were a janitor, policeman, teacher, or working at the hotels, restaurants or tourist spots. Not only are they trying their best, but they all seem to take pride in their work. Even to the point where I think they would feel shame if they are perceived to be doing their job poorly. If only more people in America could accept this attitudes at their jobs, I think our country would be a lot better off.

At the same time, I was totally overcome with feelings of gratitude for my ancestors for having the courage to leave Japan to seek a better life for their future generations. There is a term that i learned in Japan called “datsusara”, which means leaving your corporate salaried job to pursue your passion (datsu = to remove, sara = salary). It’s kind of a novel concept in itself in Japan as not complaining about your job goes hand in hand with putting your own desires to the side. But here in America, individualism is celebrated, being brave enough to be the nail that sticks out is often rewarded if you are strong enough to stand tall when you are struck by society trying to put you in line. While there, I reflected about my own life and how it could be considered a prime example of Datsusara and how incredibly grateful for everything I have now. It also got me thinking of all my ancestors, who left permanently left their home in Japan to seek build their own dream life in Hawaii. That could be considered Datsusara as well. Accepting their station in life was not what they wanted either and they were also willing to leave not just their jobs but their country in search of their own fulfillment. Even after coming to Hawaii, my parents, grandparents, and great grandparents took risks, made bets on themselves to provide a better life for their families. Without their risk taking in the past, would I have ever been in a position to take my risks? Would I have had the courage to Datsusara myself? I don’t think so. And for that, I am forever grateful.


Do you own a Business or own your Job?

I live in a small community where the ideas of business, entrepreneurship, and self employment often get muddled and mixed together. I often I hear, “So and So owns a business where they fix cars,” or some other trade which they do professionally. I know it shouldn’t but it does bother me when the term, “business owner” is used to describe that such person. This person does not own a business, they own their own job.

There is only one simply difference, but it is a huge difference between owning a business and owning a job and its this:

The earning potential of a job, is directly tied to the amount of hours you work. The earning potential of a business however is scalable, unlimited, and hours and income are decoupled.

Now don’t get me wrong. There is absolutely nothing wrong with owning your own job. In fact, it often creates the freedoms many people are searching for when they say they want to start their own business. If you are enjoying what you are doing, are satisfied with your income, and are happy, then shit, you already won. You don’t need to start a business.

But for many, they often fall into the trap of “I thought I started a business but ended up with a job”. They’re not making as much money as they thought, or they now are making a lot of money but they have to spend all their time working and have no time for anything else. They become jaded with their “business” and may even come to resent it after the initial excitement wears off.

If this sounds like you, you have your own job. But its not the end of the world. Most businesses start as your own job. So what do you to fix your unhappiness and scale from a job to a business?

The two main ways to scale from an owned job to a business is

1. Offload your work to employees or contractors

2. Implement methods to reduce or automate redundant tasks

The good news, is that if you are making money, it is easy to scale because both additional help, and technology usually cost money. The one you should choose first depends on what your primary problem is.

If you want to increase revenues by adding more business, utilize subcontractors, part time employees, or if you can afford it fulltime employees. One important note, NEVER hire until you absolutely need to hire. I see many people make the mistake of hiring before you need it. Hire ONLY when you absolutely need someone to help you. Always try to max yourself out before hiring.

If on the other hand you feel like you need more time to get to the work that actually makes you money, invest into systems that cut down redundant tasks from your daily schedule. For example, if your customer support / maintenance calls take up a large portion of your day, hire and train someone to handle tier one support and invest into a support system like Zendesk or Grasshopper. If you absolutely hate doing sales, maybe you should find someone to work on commission to generate leads (though I would highly recommend ALL business owners to lead their marketing message. It will set the public perception of your company. The last thing you need is some scummy sales person ruining the image of your  company). Same rules apply here as the first one, do not incur any additional expenses until you are overwhelmed and absolutely need it.

For both of these to work, you will need to develop a crucial skill of hiring the right people and firing the wrong people. This comes with establishing a strong company culture that resonates with your personal values. Highly recommend reading ‘Delivering Happiness’ by Tony Hsieh CEO of Zappos  for tips on creating company culture. I’ve learned the hard way that company culture is the single most important aspect of building a fulfilling company. Trust me, you want a fulfilling company because as an entrepreneur, your company is your life. Even your business partnerships, sub contractors and VAs should fit in with your culture. Ideally after you scale your job into a business, you should be spending the majority of your time doing things you enjoy while your team does things you don’t enjoy so much. When you find yourself in this position congrats you’ve scaled out of your job and life will be awesome (well, honestly I don’t know how you will feel, but all things considered, it should feel awesome).


Additional reading of Scaling out of an owned Job

Anything you Want – Derek Sivers

The Four Hour Work Week – Timothy Ferriss