• September 22, 2015

Before VENTUREAPP, there was HitUp

Before VENTUREAPP, there was HitUp

Welcome to VENTUREAPP’s Transparency Series, a weekly blog written by VENTUREAPP CEO Chase Garbarino, providing an honest look into the inner workings of our company. We believe increased transparency in the tech and startup community will help more entrepreneurs succeed. We hope this series helps you in growing your business.

Last week I gave everyone the rundown on how we founded VENTUREAPP. It’s typical for founders to wait until a company hits a homerun (or strikes out) before sharing that kind of detail, but we’re all about giving it to you upfront so you can learn from our experiences. And part of what we learned when founding this company began with an entirely differently venture altogether.

Quick reminder from my last post: in the spring of 2014, I began kicking around a side project on the weekends with Kevin McCarthy and Greg Gomer called HitUp. The three of us have always kicked around random startup ideas since we founded Pinyadda, a failed social news platform. In the past, we would always find some reason why the idea wouldn’t work, and we were always too busy cranking on Streetwise to ever take them anywhere. This idea got us excited though, and we put in a little more work on the nights and weekends to develop the idea more so than other ideas we have riffed on. We became interested in the messaging space, particularly the implications it would have on social planning. HitUp, our latest concoction, would be an elegant combination of messaging and a very slimmed down calendar experience.

Now there are literally hundreds, maybe thousands, of social planning app corpses in the app store. Everyone has a different take on what’s important – discovery of events, knowing where your friends are going, knowing who is at a venue, etc. For our thesis, we spent a lot of time texting with friends to make plans, and most calendar apps for mobile were pretty poor (Sunrise was probably the best to date). We didn’t want to create a new user behavior, just elegantly combine two that we believed should have been combined a long time ago. After I mocked up the first version of the prototype (pics below) one Saturday night, we decided there was enough in the idea to have a professional take a crack at what the product would look and feel like.

This slideshow requires JavaScript.

Kevin and I are graduates of Hamilton College in central NY and heard that Intrepid, a local mobile dev shop, was run by a Hamilton alumni named Mark Kasdorf. Mark had also created an app called Timbre with some other Intrepid folks that raised money from Boston Seed, an investor of ours at Streetwise. After meeting with Mark and the team, they developed an interactive prototype of the concept (much prettier designs than mine below).

This slideshow requires JavaScript.

Shortly after Intrepid finished the interactive prototype, we decided to show it to some people who we trust in the Boston tech community and who are smart when it comes to consumer tech: Nicole Stata, Pete Blacklow and Dave Balter – our friends at Boston Seed, Ryan Moore at Accomplice, and Jeff Bussgang at Flybridge, where Greg is an advisor. Most of the group felt pretty positive about the product and Jeff introduced us to some fabulous people in the social and mobile spaces in San Francisco, where Greg and I were traveling for Streetwise to cover the NVCA conference. The overwhelming majority of feedback we received was “REALLY tough space, but we like the product and the angle you are taking.”

At this point we didn’t really have a plan for HitUp. It was just something cool we wanted to use in our personal lives and we had spent very little time on it. Pretty quickly, a few investors showed strong interest in funding the project and we had to take a step back and think about the project as a potential business. There were a number of questions we had about HitUp at the outset. Who is the initial user? 20-something singles in urban areas that still party, or the uber-planned young Moms in their 30’s? How do we acquire our first 1k users? If we get people using the app, is it something you can monetize early or do you need scale?

Consumer apps is a tough business, which didn’t bother us, but since we were occupied with Streetwise we had some concerns and had to think all of these things through. Then came the Apple event in June 2014 where they announced a slew of new iMessage updates, including many more social features and some calendar integration. At the time it seemed like a slick product feature, but now I don’t think I have ever used it.

After the Apple event, we decided to dig pretty deep into consumer tech trends and discovered a few things: 1) A first mover advantage doesn’t seem to exist (Google, Facebook, etc.), 2) The next big hit is typically one to two standard deviations off of a current product in market (Snapchat was picture sharing that disappeared and to a smaller group – small but significant changes), and 3) winners tend to be 2-3 years ahead of the bigger players that might come into the space. Apple’s iMessage product was what our target demographic used everyday. Their announcement was enough for us to bail on making HitUp a business.

From here we had to let people know that we were not going to pursue the project, which is less than ideal because you never want it to seem like you quit something. Luckily, most understood our reservations and saw firsthand how we cranked at Streetwise.

While HitUp might have felt like a false-start from an outside perspective, it really revved us up for our next idea. It reminded us just how much we loved developing new concepts and turning them into actual companies. Each experience doing just that teaches us something new about ourselves and the business world around us. It also helps us create a checklist of procedures and considerations that should be brought to each new founding position. We were in a good place to give some critical thought to what it is that we truly love to do – connect with and help the startup community. And thus, VENTUREAPP was born.