Bootstrap Hawaii

Apologize for the lack of episode last week. Caught a cold from my kid so I didn't want to just have an episode of coughing. Just a quick update on the progress of Lesson Underground and a digression into an experience getting some insight into what someone who is new to creating an online business might approach some commonly encountered scenarios.

Really short episode today. Not much to report but I just wanted to talk a bit about how beneficial meditation can be for entrepreneurs.

First off just wanted to thank my buddy Jason Rushin at Aloha Startups for writing a small piece about this podcast. I think he oversold me a little but I am grateful nonetheless! :) I apologize for this episode, I'm running on a few hours of sleep this week because my wife caught a cold and I've been on full time toddler duty. I don't really have a write up with notes for this episode but here are some of the things I talk about: Progress of teacher idea discovery phone calls for Lesson Underground Next steps moving on to the MVP phase of this reboot Digressions into why sometimes not knowing whats impossible is a huge advantage My history as a professional musician More of my thoughts on funding

Hey we're on iTunes now! This week, I'm continuing to do customer calls for Lesson Underground. I got another 4 calls with students in and also 3 calls with teachers. I talked about it in a previous episode, how the general rule of thumb for  customer development / idea extraction / idea validation / whatever you want to call it is, you keep doing these  calls until the answers start sounding the same. This is starting to happen with my calls and its very exciting! It's beginning to look more and more like we are moving away from the initial marketplace idea for Lesson Underground and moving towards a concierge / matchmaking service for teachers and students. The general idea I'm getting from students is: 1. They want to get better at X (X being whatever they're working on. it varies but they all have something) 2. They want to find 1 teacher that they get along well with and is capable of helping them with their X and stick with that teacher for an extended period of time 3. They for the most part are

The title of this episode should give you a good idea of what its about. Hopefully it can prevent you from making the same mistakes I made. I began doing idea (re)validation calls with existing Lesson Underground members this week. I was able to talk to 6 people so far and am hoping to continue to get more feed back and collect more data points. While doing these calls, it quickly became evident that what we had built was just not what customers were looking for. I talked to my partner Aaron about the things I was hearing from these customers and we both independently came to the conclusion that it would just be too expensive to try to retool what we already have and paid for to effectively solve the problems the customers are telling us they have. Thus we are essentially starting over, throwing away a $50k investment. As bad as I felt for wasting our money, I feel equally as bad about not using the app Sudokrew had developed for us. Sure we paid them, but no one likes seeing something they worked really

In this episode, I talk about what we did wrong so far with Lesson Underground, what we did right, and most importantly what I'm going to start doing now. Cutting to the chase, we did a lot wrong, but the root cause of it all boils down to one thing. Laziness. Specifically due to having money to spend on this project. In the past, we never had much money so we would be forced to figure out how to do things in the most cost efficient way. Now that UU is doing well, we got really lazy with a bunch of things and kind of threw money at problems which lead to extremely sloppy execution on our end. Here is just some of the unspeakable and embarrassing things we did / did not do We assumed product / market fit due to the small traction we had with a similar but not exact product within Ukulele Underground. We failed to validate the delivery method of the solution (skype lessons) We failed to validate the pricing of lessons with customers before launch and set expectations with customers properly We failed t

The start of a new company and a new journey. In late 2015 my friends and I launched a new company called Lesson Underground. We invested around $50,000 to building a bare bones beta of the app and launched it to a small pre-launch mailing list. Unfortunately, it did not take off as we hoped which brought about this podcast. I've wanted to do a business / startup focused podcast for a while now but I never felt I knew enough to be one of those gurus doling out advice to the masses. I also feel like I don't have as much success as needed to be one of those types of people. When Lesson Underground did not work like how I expected, it provided an opportunity to create a concept where people who are interested in building an online business or startup can come along with me for the ride. My plan is to share and document as much as I work to build Lesson Underground from an idea, into a profitable business. Even though we've been in business with Ukulele Underground for 8 years now, there is still so much I don'