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I left @prendalearn 2 months ago to start @fwdthinkingcity. To many, this appeared like a crazy decision. Prenda is a YC and VC backed company, growing at a rate faster than you could likely imagine, and it is likely going to be unicorn within a few years. Why leave?
A thread
A thread
First off, I am a founder to the core. Always have been. From 2008 --> 2014, I was bootstrapping a music career. I was putting videos on Youtube, selling show tickets, selling shirts with my face on them. My life was my music career. I only changed focus when i realized I sucked.
But if you look carefully at my music career, you see the same Mat you see now. A hustler, working his ass off to make it work. Someone who will outwork everyone, just to make his dreams work. Here's my YT channel I started in 2007 https://www.youtube.com/user/westbrook7221
When I realize I sucked, I needed something else to fill the void. Something to work towards. A mountain to climb. I always look for the next mountain to climb when i don't feel like my current one is the right distance or slope for me. So I moved making hype videos.
I sold my friends, local greek orgs, Relay For Life, all od these orgs to make videos for them. I had a nice camera, a GoPro, and a creative mind, and I needed to replace the hole in my right brain. I needed a hustle. So I made videos https://www.youtube.com/user/mshermantv
I did this for about a year, and enjoyed it. I started in June of 2014, and I worked on it up until July of 2015. I made some great videos. These were some of the best times of my college career actually. I LOVED making videos. Here's one of my favorites.
Now you might be asking, Mat, why didn't you stop making videos in July of 2015? Well, I had a question I needed to answer. Was this something I wanted to really dedicate to and be the best at the craft? Did I love making videos THAT much to commit to this being IT for a decade?
For some reason deep in my soul, was no. I knew I was good, not great. Just like a music days. And I had the potential to be great but it didn't seem hard enough. If I became the best videographer in the world, then what? I didn't feel like it was a mountain worth climbing.
I guess I got bored. There were the same type of edits. Same type of videos. Go on a shoot. Edit videos. Go on a shoot. Edit videos. I didn't love the craft. So I decided to try something else. Now, I am pretty pissed at myself at this point. I keep changing paths.
And everyone knows the value of compounding effects. The more time you spend in a career, you more people you meet, the better you get, and the more successful you become. And I so far sunk my time into things I didn't want to for the long haul. I was frustrated at myself.
I was a Communication major with ASU, no great grades, a failed music career and failed videography "career", with no plan for what I wanted to do after college. I was a senior in College at this point, in 2015. At it was around this point I got my first startup idea.
The origin story for my startup career is for another thread, but it's worth saying, but some reason I got really attached to this startup concept. I don't know what about it I liked. Maybe it was that I wasn't qualified to start one, and I like that. Maybe it was something else.
But I instantly dove into everything I could about startups. I:
- Listened the @sama's to How to Start a Startup Stanford Course
- Got dozens of books on startups
- Got involved in the local startup ecosystem
- And I tried my own startup, called Schmooz.
- Listened the @sama's to How to Start a Startup Stanford Course
- Got dozens of books on startups
- Got involved in the local startup ecosystem
- And I tried my own startup, called Schmooz.
I had no mentors in SF. No one to show me the way. I stumbled through Schmooz. Made all the first time founder mistakes I know see as stupid. Had
- A team of 10 to work on it, no one technical
- Wasn't solving a real problem
- Too focused on solution, not enough on problem
- A team of 10 to work on it, no one technical
- Wasn't solving a real problem
- Too focused on solution, not enough on problem
I also applied to YC two times while working on Schmooz. I was SURE we would get in. How naive was I. We got rejected both times, I was devastated, but I kept going. Schmooz went into post grad days for me. I was ubering for a living to make it work. It wasn't working.
So one day i walked into my apartment where I lived with my cofounder, Travis, and told him I was done. 1.5 years sunk into it, nothing to show for it. Just more wasted time. A failed music career, videography career, and a failed startup. ASU Grad. Comm major. Felt defeated.
Fast forward 6 months, I had gotten a job by this point, but wasn't satisfied. I wanted to try another startup. I also just didn't love working for someone at that point. So on April 10th, 2017, I quit my job at started @PubLoft. Time to make it happen, a second try.
In short. I got @PubLoft to $5,000 MRR from April 2017 --> Jan of 2018, then it died because I had health issues. Another failure. In this time, I also had applied to YC twice. Both times, we got rejected. I was struggling so hard. I was so mentally beat.
After a small break from Jan to June, I started it again with @rarelyJeremy in June of 2018, and we got it to $25,000 MRR by Jan of 2019. FINALLY, I am close to the promise land...success. We get into a great accelerator, and get a $100,000 investment. We made it, right?!
No, this is well documented, but PubLoft died later that year. From $25,000 MRR and a $100,000 investment to $0. Don't ask me about it. I was sooo fucking close to make all this work worth it. SO CLOSE TO THE PROMISED LAND. Yet, I fucked it up. Again.
In November of 2019, I reached out to Kelly, CEO of Prenda, asking him if he was hiring. He directed me to Rachelle. She interviewed me. I did well, and I joined the team. I immediately had an impact. Although the market didn't value me, I didn't learn skills that Prenda valued.
I did my WATZ thing on Prenda. Got them more organized through running meetings through Calendly, or implementing the pre-enrollment form for parents. Or coordinating around table in Flagstaff, figuring out to handle out most recent rush of parents.
Everything I learned on my failed startup journey, I was able to apply to Prenda. Dare I say, it was easy? Sure, it was easier. I was doing an impossible job as a founder with no experience building a startup outside of SF. I needed to learn the skills to survive.
but what was surviving in the market helped me thrive at Prenda. I realized I wasn't so weak after all. I actually had some skills to bring to the table, and I did. but there got to a point in Prenda, where it felt almost too easy. We were at 40ish people at this point.
It was really growing up, and all of my skills were in the starting up phase. And I put A LOT into these years. Some would stay I started in 2015, I would say i've been hustling since 2008. 12 years, no success. Only to find myself on this team bound for success. It felt wrong.
yes, I had some equity in Prenda. Yes, it would have taken 4 years to full vest. So I needed to decide if I was going to call my Prenda my home for four years, or try again and take all my failure and change the narrative I painted for myself.
Prenda was in some ways, guaranteed success, almost like it was given to me. But I had put 12 years into a founder journey, and I was better than i'd ever been at this point. Was I really going to just..stop? Call it quits, at least for now?
At the same time, the world is ON FIRE. This sucks for many reasons, but this is a prime time to start a company. So this felt like a crossroads for me. Pick Prenda scale up with it. Or try again w/ a startup, in this new consumer landscape. I decided to try again.
I couldn't do it on the side. If I was going to start a new startup, I need to put my all into it to ensure success. I needed to give it everything I had. I couldn't moonlight it. So this is what I did. So, Kelly and I talked, put in my two weeks, and i've been sprinting since.
I'm to this point where i'm so immune to the pain of being a founder, there is no way this won't win. I've gone $XX,XXX into debt for startups. I've sunken years into startups. All for nothing. @fwdthinkingcity is my last chance to finish the job I started in 2008.
If I am going to make all of this pain worth it, it is going to be BECAUSE OF ME. Not because I joined a rocketship and called it good. This is personal. The is me vs. me. Prenda couldn't give me that. I needed to be a founder to make the last 12 years worth the struggle.
Call me crazy. Call me irresponsible. Or just call me a founder. I'm not not in this for the clean story. I'm in it to finish a personal narrative. It's very personal to me. Will I regret this choice? Only time will tell, but i'm not counting on it.
