Dealing with Shame

In todays world, starting a business is sexy. Shows like Shark Tank are all the rage and get millions of views. What these shows don’t do, is show the reality of what it takes to start a successful business and the consequences of failure.

I've been a hustler since the day I was born. At the age of 6, I would buy a box of 300 fortune cookies for $8 from a restaurant and sell them at my school for .25 cents a cookie. That’s a 9x return. 

I guess I get my hustling nature from my childhood. I was always poor. I wanted to become rich. So I did whatever I could to get there. 

That led to some good decisions, bad decisions, and terrible decisions. Most of the people who read this know my story, so I won’t focus on my terrible decisions, but if you would like some context, you can read my article here. 

This article will focus on my second business, Byte Size Moments, and the hardships along the way. In truth, I’m long overdue on writing this article because of my shame. 

Early 2015, I entered a program called Defy Ventures as an EIT (entrepreneur-in-training). Defy is a non-profit that teaches people with criminal histories how to harness their “illegal hustle” and turn it into “legal hustle.” It was here that I came up with the concept for Byte Size Moments. 

Byte Size Moments started with a simple idea. How do you personalize long-distance gift giving? Studies show that 90% of the “joy” that people receive when giving a gift is the expression from the person receiving it. Don’t ask me how they came up with this metric. 

So I came up with an idea to allow people to record a video, we would hand deliver it, and record the reaction of a person receiving their gift. You can see an example here. 

This idea led to me winning several business pitch competitions and even being invited to pitch on MSNBC. Link here. 

Throughout the process, investors kept centering on one subject. Scale. Before, I had no idea what that meant. I simply thought, lets start a business and grow our customer base. I soon learned that “scale” from an investors perspective was, how do you take your service and grow it to millions of customers. 

I hadn’t thought about that. So in the effort to “scale” and get the millions of dollars that I was asking for to grow my business, we switched over to a tech platform. 

To make a long story short, 12 months after switching to the tech platform, I became an alcoholic, dead broke, suffering through severe depression, with all of my possessions sitting in my car in California. At one point, my car was towed with everything in it. I walked 3 miles to find the place where they had taken my car. I stopped into a local Starbucks to grab some wifi and took a look at my bank account. I had $24 left. I cried. 

This wasn’t the first or last time that I would cry over my company. I remember waking up in the middle of the night, dripping in sweat, thinking about the people that were working with me to build my dream and how my failure would affect them. I remember laying down in the middle of the street in front of my house, crying my eyes out, seriously contemplating jumping off a bridge. I thought about my most recent kickstarter campaign and how there was no way that I would be able to fulfill my promises to the people that entrusted me with their money.

January of 2017, I finally decided that it was time to close up shop. I did this in secret. Filled with shame, all I wanted to do was hide from the world. 

My identity and my business had collided together to form who I was. You couldn’t think about Byte Size Moments without thinking about me. You couldn’t think about me without thinking about my business. I viewed my failure as an entrepreneur as a failure of who I was as a person. 

That’s the point of this article. Being an entrepreneur is not sexy. It’s a hard grind, with you feeling in survival mode at all times. That being said, I wouldn’t trade it for anything in the world. 

It’s now 2 years after hitting rock bottom. I’m happy to report that I am no longer an alcoholic or depressed. I ended up starting two other ventures and they are both doing well. Much of that success is attributed to the people that I’ve surrounded myself with. 

I can’t thank my mentors, Bob Frankenfeld, Catherine Hoke, and my fiancée Kami enough. They stood by me when I was a shell of who I was. I'm grateful for my teammates, Kami, Chloe, Craig, Landon, and Wandrille for putting up with all of my crazy ideas. I'm grateful for my customers and funders who trusted me to deliver. I'm grateful for the endless stream of mentors that chose to dedicate their time and wisdom. And I'm grateful for Matt Mochary, Andy Bromberg, and Jason Green, who are guiding me on my newest venture, FreeWorld. 

Here are the 5 lessons I learned from my experience.

1. Entrepreneurship is all about peaks and valleys. You have to be persistent, but you also have to know when to call it quits. 
2. Learn to sift through the noise. People will tell you what you should or shouldn’t do. It's your job as the Founder to pick the best direction. 
3. Failure is okay. You are not your business. Your business is not you. Humans have an incredible ability to adapt. You will live on. 
4. Don’t pursue a business based on selfish, short-term thinking. Pursue a business because you’re obsessed with delighting your customers.
5. Being vulnerable is freeing. For the first time in a long time, I feel free again.