My first startup failed miserably

But I wouldn't trade the experience for anything.

My first startup failed miserably, but I wouldn’t trade that experience for anything.

Back when I was a sophomore at the University of Maryland, I was part of a few different entrepreneurship classes and programs. And just like any other guy who wanted to start a company in college, I thought I could build a better music app.

A bit ironic now, as I write this newsletter that spawned from a Spotify playlist (which kicks ass) — but I have always enjoyed finding and curating music for others.

I wanted to build an app built entirely around curation and music discovery (think Twitter meets Spotify). I called it JukeTree, and I spent way too much time designing this super busy logo. Kinda slaps though.

I think I got high and hand traced that tree in PhotoShop

Fresh off reading The Lean Startup I decided to create an MVP which was just a YouTube video where I walk through the functionality with some wireframes I created. This video demo is both hilarious and better than 90% of the demos I’ve seen from legit companies.

The real problem with the idea: who the fuck was going to build this?

I was studying Mechanical Engineering but had 0 experience building mobile apps. Neither did any of my friends.

I was in a bunch of entrepreneurship classes and programs and realized, none of these people actually had the skills to build their ideas either. Meanwhile right across campus was a top 25 Computer Science program.

🚨 Pivot 🚨

I dropped JukeTree (RIP) and convinced my friend and his twin brother to help build a platform to solve the disconnect between early ideas and the talent needed to bring them to life.

VentureStorm was born.

Step one was to actually build the platform. So in a way, we were kind of back where I was with JukeTree. But this time we all decided to take online courses and teach ourselves how to code using Ruby on Rails.

There wasn’t time to become experts, so we just began building and learning on the fly. No excuses, no waiting, just a pure bias towards action.

Fortunately my two co-founders, Taylor and Tommy, were studying Electrical Engineering and had a bit more experience with software. They definitely pulled more weight than I did when it came to building the early platform.

What an absolute crash course on life and business. A couple 19-year olds figuring out how to register an LLC, file trademarks, set up corporate checking accounts, onboard users, conduct user interviews, facilitate in-platform payments, and build literally anything users asked for.

Creating a two-sided marketplace was super hard. Because rather than just trying to acquire a single type of user, we needed to attract two totally different user profiles:

  1. Startups / entrepreneurs

  2. Software developers

We were students with $0 in spare funds, so we had to get super creative and scrappy. Here’s some of the things I did to try to get startups to signup for VentureStorm:

  • I would write super cringey blog posts on Medium to try and attract startups to the platform (they still exist).

  • We launched a college ambassador program.

  • I’d spend hours answering any entrepreneurship related question on Quora and always plug VentureStorm at the end of my answers.

  • Tried to get any sort of PR or press we could (like this article we got in the The Washington Post) !!

As for getting software developers to signup…

Universities would host “hackathons” where thousands of computer science students would spend their entire weekend in an auditorium coding and building a project that they would present to a host of judges. There were always massive corporate sponsors like Google, AWS, Microsoft, etc. They would sponsor booths to try and recruit the top student developers.

Given we had no money, we would befriend event organizers on Facebook, pull the “student card,” and sponsor these events for a few hundred dollars (vs the $50,000+ the other corporate sponsors paid).

Setting up shop at a hackathon

We’d leave Friday morning from the Maryland campus and drive all across the country to show up at these university hackathon events. If we were fortunate enough to know someone who attended that school, we would crash on their couch (remember: no money). Otherwise we’d find an empty classroom and crash on the floor (footnote: the empty University of Toronto classroom in January was very cold).

We sponsored events at Harvard, Cornell, Drexel, Michigan, Georgetown, University of Toronto, and a bunch more.

Being in a fraternity 🤝 wearing Timberland boots

We ended up building a decently robust platform with live chat and payments, had 10,000+ users, and some revenue. Most importantly, I had learned a whole lot…

  • How to code

  • How to take something from zero to one

  • How to be creative, gritty, and scale users with $0

  • How to always listen to the user and build what they want

  • How to make sacrifices (i.e. fun weekends in college) to pursue something you believe in

  • How to fucking hustle

But two-sided marketplaces are tough. The business model didn’t really make a ton of sense, we had no real upper-hand or experience in building this type of business, and the space was well-funded and competitive with other freelance-related solutions.

Fast forward to 2016 and I had just graduated with $125,000 of student debt, was living in my parents basement in rural Maryland, and was still making $0 in salary.

With my monthly student loan payments set to start in a few months I made the decision to step away from the company I just spent 3+ years tirelessly building. I began freelancing and building some Shopify sites for small businesses while looking for a full-time job.

Then one Saturday morning I was driving home from DC when I called and caught up with my buddy, Austin Rief. He mentioned Morning Brew (which he cofounded) was experiencing a ton of traction… but they didn’t have an engineer to build a few of the things he wanted.

He asked if I had some spare time to help, and the rest is history.

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The vibes in this office are nothing short of immaculate. Granted, the 3 hours prior to sunset the sun is probably a total pain in the ass. Worth it for this (fake) pic though.

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Turn on, tune in, drop out. Click on any of the tracks below to get in a groove — each selected from the full Big Desk Energy playlist.

Some of my favorite content I found on the internet this week…

  • I’ll be speaking on a virtual panel today (!!) with a few other heavy hitters about newsletters. Register for free here.

  • Las Vegas released a report on the economic impact of last year’s Formula 1 race (Twitter)

  • LinkedIn is testing TikTok-like short-form video feed (TechCrunch)

  • Robinhood is launching a credit card made out of legit gold that gives you 3% cash back on all categories and 5% back on travel (Robinhood)

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