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.


One thought on “My Biggest Mistakes – What I Wish I knew as a New Entrepreneur”

  1. Great blog Ryan! When you can finally take a step back and admit to your shortcomings and ask for help, it allows you to finally grow and succeed. In music, I seems “talent” is the same as “smart” because hustle>talent. And reliability and not being a jerk>talent. I especially like the part about making a product people want. As artists, we constantly struggle with putting out music that is artistically what “we” like but not necessarily what anyone else wants to hear. I learned that I can be an artist in my garage and play for free, whatever I like, but I should invest money into something with commercial value. Like you said, it’s a business! So happy for you bro! Hope to see you soon, I’m moving back home!

Leave a Reply

Your email address will not be published. Required fields are marked *