3 Life Lessons From My Entrepreneurship Journey

Hawaii Entrepreneurship HAVEN
Hawaii Entrepreneurship Journey

I recently had the opportunity to share my Entrepreneurship Journey at a speaker session hosted by PACE. Before I got there, I asked myself why I went to the PACE speaker sessions as a student? The answer was that I wanted to learn more about the entrepreneur — their triumphs and tribulations, their experiences both good and bad, and any lessons learned, especially the hard ones.

I separated my journey into three phases. Each phase has one key takeaway, theme, or lesson. Also, each phase builds on the last — meaning I didn’t get to the next phase until I mastered everything in the phase before it. The three phases are (1) The Creator, (2) The Operator and (3) The Leader.

Hawaii Entrepreneurship Creator

The Creator

The Creator Phase is exactly what the title suggests. It’s about creating. Being a creative. Being a creator. When I first started HAVEN, I didn’t know what the heck I was doing. I didn’t’ write a business plan. I had no real guidance, no part-time job – nothing. I just had something to say and the graphic design, marketing and visual communication skills to say it. So, with just $500 in my pocket, I printed my first batch of graphic tees and sold them out of my backpack around campus. I bootstrapped the whole operation and reinvested everything back into the company.

Show up! That was the key lesson during this “Phase.” I could have spent days, weeks, or months second guessing and doubting myself about why I shouldn’t or can’t do what I did. Eighty percent of success in life is just showing up. Initially, I considered myself a pure creative — I just wanted to make stuff, you know? But as shirts started selling and I started to gain some traction, HAVEN went from a hustle to a full-time operation.

Hawaii Entrepreneurship Operator

The Operator

In 2015, I picked up a wholesale account with Blue Hawaii Surf at Ala Moana. Then, a few months later, I picked up a wholesale account with Local Motion Hawaii. I saw my designs placed on the shelves of seven retail stores across the state. I learned very quickly that it wasn’t just about CREATING something. It was also about OPERATING it. Business Ops are the “non-glorious” behind-the-scenes tasks that no one ever knows about but have to be done. And Operating a company takes a lot of hard work. More work than most people have the capacity for. It’s putting all your effort into your company and then digging deeper and putting even more effort.

One of my favorite books is called Grit by Angela Duckworth — she says that: achievement = skill x effort. We know what effort is, but how do you actually define skill? Angela goes on to explain that — skill = talent x effort. You develop “skills” with some degree of talent multiplied by the amount of effort you put into developing those talents. If you substitute skill with (Talent x Effort) in the achievement formula, you’ll see that effort is in there twice. Society puts a lot of emphasis on talent. But talent will only take you so far. It’s the effort you put in that really, really matters. If you look at the formula, talent only counts once. Effort Counts twice. That’s the key takeaway/lesson of this Phase — Show up first. Then work your ass off.

Hawaii Entrepreneurship Leader

The Leader

No matter what kind of leadership experience you’ve had in the past, nothing will prepare you for leading your own company other than leading your own company. It’s a huge responsibility – leading people into an uncharted territory without a map or a compass – just a machete. In retrospect, I had a lot of learning to do. Just last year, I put together a team gave everyone roles and responsibilities – and just was not able to manage all of it. My first team — I failed them. I wasn’t ready. But that’s a common theme as an entrepreneur — you will be asked to do things on a daily basis that you aren’t yet capable of doing. The Leader Phase can be summarized with the phrase “Fall Seven. Rise Eight.” That means – Failing others. Failing yourself. Then dusting yourself off and resolving to learn and continue.

There are thousands of books written on Leadership. I’m no expert, but I truly believe that the foundation of Leadership is based on two principles: (1) continuous learning and (2) rising to every occasion (stepping up). It’s an inside out approach to Leadership. Being a leader means not really think in terms of disappointment. Instead it’s about thinking that everything that happens is something you can learn from. Then taking that mindset, leading by example, and inspiring those around you to do the same.

Hawaii Entrepreneurship Lessons
Hawaii Entrepreneurship


In summary there are no quick fixes in life and anything of real worth will necessarily take a lot of struggle and perseverance. Show up. Work really, really, really hard. Learn, fail, learn, and grow. And persist. And remember that 97% of the population is employed by the 3% that did not give up.

One Comment

  • David Holt says:

    This is awesome! Looking forward to your next post. Love how you broke it up into Creator, Operator, Leader. You must master one before moving on to the next. I would like to learn more about your transition from creator to operator… that seems to be a place where a lot of entrepreneurs (especially students) get stuck or overwhelmed. Thanks for sharing!

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