Jumping back into the FastLane

[kaizening]

Hey everyone,

I've read a lot of your posts over the past couple of weeks and I've picked up some great advice on mindset and tactics. So first off, thank you to MJ and everyone else who contributes to this forum.

I'm not into talking about myself or my accomplishments, but seeing as that's the point of this thread, I will indulge. In fact, this is the first place I'm telling this full story. (MJ, if you want proof for anything below, just message me

I doubt many people read these intro threads anyway, but I figure it would be fun to document my story so far before I jump into a new Fastlane business, so here we go:

I'm 25, living in SF, and am a self-employed software contractor.

I grew up riding dirt bikes in Virginia. My pride and joy was a whiplash-inducing motocross bike with a sweet dual exhaust (CRF 250R for the gear heads).

When the entrepreneurial bug bit me at age 17, I decided to sell it to fund development for a software business.

HA! "Software business."

In reality I kissed my sweet ride goodbye just so I could pay some guy in Jordan $6,000 to build a mediocre soccer fan site.

Then, when I needed something changed on the site, more $$$$ out the door.

So that motivated me to learn how to code. I learned how to build web apps in PHP and started booking freelance gigs on Elance. This was back in 2010. I landed a contract for $17k to build an app and I thought I was filthy rich.

I bought a new laptop, apple monitor, fancy chair, etc. I blew through that cash like it was Weimar Germany.

That taught me how quickly cash can disappear and just how little satisfaction you get from blowing cash. Creating stuff is where the real satisfaction lies.

Over the next year or so I kept slinging spaghetti code for dough from my dorm room.

Eventually I got tired of freelancing and decided to try a few "startups" in school with my buddies. One of them was an SMS marketing company. I built an app that would send exclusive deals to students' cell phones. I was going door to door selling to local businesses, trying to get them to pay for ads.

I remember showing up at a pizza join in a shirt and tie, complete with pit stains from the summer heat. They asked me if I was a jehovah's witness.

I gave up on that idea pretty quickly and moved onto the next one.

This time I decided to connect students with cars to those without cars. The ones without cars could pay to be shuttled around or to have an errand run for them. This was pre-Uber and Instacart.

During the first month, my partner and I ran a promo for Chipotle burritos delivered to your door for $5. Just to get people using the thing. We hadn't signed up any drivers yet so I figured I would just use my car to deliver.

About an hour after the promo went live, word got out. We couldn't keep up. We were about to be bankrupted by hungover Chipotle fiends.

By the end of the day we were delivering piles of cold burritos hours late. I was exhausted, but hopeful we would have some traction, or at least some notoriety.

Alas, it wasn't to be. My co-founder decided to drop out of school to pursue a startup opportunity in SF, and I was about to move onto better things myself.

I joined another startup at my school as a technical co-founder. They already had $20k in sales, but the guy who built their prototype had bailed on them and took the code with him. I owe him a thank you card.

I went on a coding rampage and rebuilt the app in a weekend. We launched on time and that was the beginning of my first successful entrepreneurial adventure.

Fast forward through a year and a half of grinding out code after class and during the summer, and it's senior year. We have big clients like Bose, Microsoft, Coke... and we're talking to investors! Basically living the startup dream. My co-founder and I were wined and dined by potential investors (we got bonus points for being young, no doubt). The world was our oyster... Speaking of oysters, we got tons of 'em for free at our law firm's summer rooftop parties. Life was grand.

Then we got into TechStars. HO-LEE-SHIT it was happening! Except, there was a catch. TechStars wouldn't take us if we were still in school. So we had to drop out with ONE semester left. Our parents were less than thrilled, but ultimately supportive.

So while our friends finished up classes and enjoyed the best of Senior year, we were living off iced coffee and the slim hope of raising money on demo day. We were determined to grind harder than anyone in the TechStars office. We would ride our bikes through early morning traffic in Boston to get to work first, and ride back across the river from Cambridge at 3am. It was not sustainable, and worst of all:

We failed to raise money on Demo Day.

Instead, we raised the day before 😀 😀 😀 (my co-founder and CEO deserves all the fundraising credit - I was fully focused on the product by this point). We brought our total funding to a smidge under $2 million - just a few days before graduation day.

Since I only had a semester left, my school still let me walk at graduation day. Instead of a diploma they gave me an envelope with a letter inside - "We regret to inform you that you have not completed a sufficient number of credits to receive your diploma."

I smiled with smug satisfaction.

From then on we were full on adults (sorta) running a company. We probably spent a little more on office space than we needed to at first... We had the top three floors of a beautiful tower overlooking Fenway Park in Boston. The middle floor was an indoor basketball court sandwiched between two industrial looking office spaces with floor-to-ceiling windows. All the trappings of startup "success."

After ~3.5ish years as CTO, I entered a terrible phase of my working life. Burnout. All the long hours of coding, mixed with a sense that what we were building didn't have much meaning to me, lead me to lose all motivation to work. Truthfully, I was jaded and couldn't see the long-term picture anymore. Add to that a certain level of immaturity and lack of character, and I was ready to jump ship.

I spoke with my co-founders and we agreed to part ways. They're still great friends to this day, and the company is up to ~40 employees now. I admire them for their grit and determination. I still have my shares, and in the case of a liquidation event, I'll owe them big time.

After that I went on a 3-month solo backpacking trip through Europe to blow off steam and do some much needed reflection.

I came back feeling refreshed and ready to jump back into coding. After three months without an income, I was ready for some paychecks. So I started trading time for money (albeit at a premium rate) and told myself I was happy to be out of the stressful startup world.

A couple of months later, one of the companies I was working with was accepted into Y-Combinator.

I just so happened to be the one who built their core tech so they asked me to join them. Another gold gumball out of MJ's Gumball Machine.

To go through YC, you need to own at least 10% of the company, so that meant equity and right back into the startup grind.

Long story short: YC was fantastic, we raised money, I moved in with my girlfriend in a sweet apartment in SF, and .... the business floundered. I was one of four co-founders and we had to stop taking a salary (if the pittance we were taking home each month even qualified as a salary) just so we could pay our contractors.

Cue the quarter-life crisis. I was about to turn 25 and I had somehow found my way into another startup, only this time I never really believed in it. I joined full-time because of the glamour of YC and because I liked the co-founders. Now I wasn't getting paid and was bleeding cash thanks to signing a lease at the height of SF's housing market. So I had no choice.

I went back to trading time for money. I've been doing it for about a year now. Steady, hourly work on fun projects for easy-to-deal with clients at a fantastic rate - with plenty of time on the side to do whatever I want. I have no complaints.

EXCEPT ONE! I'M AN ENTREPRENEUR AT HEART!

I love the thrill of building things. I love the excitement of knowing that something I create might impact thousands or potentially millions of people.

So, I'm jumping back into the game. I've learned a lot about myself over the past year. I've spent a lot of time reflecting on my values, refining my personal philosophy, and building productive habits. TMF and Unscripted have been great motivators as well (THANKS MJ!).

I've recognized that although I'm great at building things, I've always been a SELFISH entrepreneur. Every idea I've had in the past has been something I thought was oh-so-clever and tried to force on others. Rather than listening for a burning pain and soothing it with a solution.

Oh, I'm also dogshit at sales and marketing. Luckily, I've just started digging into that side of the business and find it fascinating. Especially when I realize just how ignorant I have been all along.

This is the beginning of a new journey. A different one from years past. I am entering the arena once again, but this time I'm focused on the customer's needs first and foremost. And here's the big one: I will not write another line of code on an app until I have pre-sales for it. If you're a developer, you know how hard this is going to be.

That's it for now. If you read this far, I'm impressed. This ended up being a more of a personal reflection for me. A nice little narrative I can look back on and say "ah yes, this was the turning point."

Now back to being rather more introverted.

- Chase

 

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