I asked my good pal Mary to join me at Startup Weekend as I thought it would be good to have someone to chat with during the event. I thought Mary might also make some new connections of her own as she’d just retired and was looking for something new to do.

I was glad that she was there because pitching at Startup Weekend brought me so far out of my comfort zone, you’d have to steal a spacecraft to get there. I didn’t really have a good concept of what the event was going to be like and how real starting a company in a weekend would feel. It was great to have a friend by my side.

I met Mary shortly after moving to Tucson six years ago. She is a Celtic harpist who can play traditional tunes by ear, like me, and then more. When we play together, it is just lovely. Before Mary, I hadn’t played with anyone who was able to put their own spin on traditional music so freely. She is a masterful improviser with amazing stage presence. For awhile, we did gigs here and there as a duo. Mary was instrumental in introducing me to the Celtic music scene in Tucson. We passed gigs we couldn’t do to one another through the years as well.

She is what I think of as a “mensch”; a person of integrity and honor. She is also generous, kind and warm. She’s raised three children, is an ex-kindergarten teacher and loves babies. She is creative, smart, an excellent writer, a voracious reader, great with people and knows almost everyone in town. She really is the life of the party; if you’ve ever been to one with her, you’d remember.

So when I decided I wanted to make iTipArtists a go after Startup Weekend, there was no one else I trusted to try this with except Mary. And honestly, after the whole experience of iTipArtists, the startup, I found that the reasons I wanted to work with her were spot on. She really is a mensch.

But, I made an error of believing that since we’d worked together so well playing music, we’d easily be successful doing something else vastly different. When we practiced music together, I would play a piece and she would fill in and improvise, making the music fuller and even more beautiful. It was as if I threw a ball in the air and she threw it back. That was all we needed to do to be a success at creating lovely and unique music.

However, it wasn’t so easy starting a company together. While we had played music together before, a new company has so many more types of work. Yes, we had to be creative to put together a viable product; but we also had to learn a ton of new practical business related things, go to quite a few meetings at the Arizona Center for Innovation, meet with and research our customer, network with the Tucson business community, make presentations and keep up with our field’s current issues (read, read, read), to name a few. This was a whole lot more than being creative together.

We did our best but it became clear to me that we saw things very differently early on. Both of us come from such different backgrounds and have worked on vastly different types of projects. Apart from music, I have not worked with anyone else in a creative space, nor have I been required to network and constantly meet so many new people before. I don’t believe Mary has worked on such a large and technical project before.

We never fought, or had bad feelings pass between us. However, I don’t feel we accomplished what we set out to do efficiently (though we worked off our patoots day in and day out!) We had yet to develop a great workflow between one another.

I believe that if I had more time to dedicate to the business, we would have been able to get into a good groove. I have trust in my friend, as she is a mensch. I think it was a challenge to both of us for growth.

For me, this was clearly not the reason I decided to leave the business, but it was a lesson learned:

Working with someone in one sphere does not wholly inform you about how they will work in another. People have subtleties when it comes to work that are easy to miss.

I think it is likely that it will always be a surprise how you work with someone else in a startup if you have never worked on a startup together before. It will be tough going at times. You have to trust the other person and be as honest as you can with them.