We had met at a Startup Weekend in 2010 in NYC and quickly bonded. We founded Lean Startup Machine soon after and made some early strides. Word was beginning to spread and our events were getting larger. But as we sat in a dingy San Francisco dumpling shop, it became quite clear to my partners and I that we all had very different goals.
“What do you want to get out of this?” our mentors asked each of us.
I wanted to build a SaaS business. Another partner wanted to travel around the world. A third wanted to scale an events company. That’s when I began to realize that life presents infinite possibilities, yet we’re very much finite. In reconciling this, I finally accepted that “rolling with it” wasn’t such a great strategy.
For us entrepreneurs, this can be a tough pill to swallow.
You want your company to be dynamic and diversified, and imposing constraints seems counterintuitive. But it can actually help you accomplish more. This certainly wasn’t obvious for me starting out, but in learning from both my successes and failures, I’ve settled on a few basic guidelines for launching new projects, choosing new partners and defining my own role.
DON’T be a jack-of-all-trades—forever
One of the biggest traps we entrepreneurs fall into is trying to do everything on our own. When you’re first starting out, this makes sense because assuming a bunch of different roles is a great way to really understand the business you’re getting yourself into. But once things begin picking up, it’s important to shift out of that mindset and focus on the areas that truly demand your attention.
I’ve always been most passionate about developing technology and products, but since I also have a background in writing and design, it seemed natural that I should handle marketing and communications too. From there, I figured since I was already building the product and developing the messaging, it wouldn’t be a stretch to run the business too.
I was CEO, CTO and CMO and quickly learned to hate two-thirds of every day. Eventually, I realized that aside from being unhappy, I was only doing an average job. I had three roles, was passionate about one, and stretched too thin to excel at any. Today, I stick to technology.
DON’T build a startup that sounds like a startup
This tip is pretty basic and something I fully learned from experience. A while back, I was involved in a company called The Hancock Project, which was basically a service that converted handwriting into web fonts. I still think it sounds like a cool idea, but as I discovered, cool ideas don’t always translate into a real business.
The simple wisdom here is if you’re not addressing a real pain point with your product, then it’s probably not a real product. We made some revenue with Hancock, but eventually hit a wall and recognized we were going down the wrong path.
DO look for collaborators, not friends or personalities
Until fairly recently, I didn’t really know what to look for in a partner and defaulted to criteria that seemed relevant at the time. Did I like the person? Did our personalities click? Could I see myself having a beer with them? Those were more or less the questions I asked before embarking on the project I alluded to above, Lean Startup Machine.
We were four guys who hardly knew each other and for a while, things ran smoothly, but as the company grew, we needed to decide on how to scale. That’s when it became painfully obvious that all of us had completely different goals and work styles. Eventually, I walked away, though I’d still have a beer with any of them. We were friends, but sucked at collaborating together.
Another mistake I made early on was focusing too much on personality traits. I took it as a given that an effective businessperson should be an overt alpha—an assumption that backfired rather spectacularly on a few occasions.
DO identify your core strengths and weaknesses
While it’s obviously important to get along with your business partner, the key to choosing a good collaborator is knowing your own strengths and weaknesses and what skills/roles a particular project requires to WIN.
For any project, you should define the work that’s required and map your skills and experiences to those needs. It helps to literally do this on paper.
Have each person take a few minutes to write down his or her individual strengths (Strength A, Strength B, etc.). Next, rank the strengths in terms of proficiency (awesome, decent, mediocre, etc.). Next…
If you’re being honest with yourself, there will be holes that you can’t fill on your own, and those will be the skills and traits you should look for in a prospective partner.
The bottom line is none of this is a science, but if you heed the tips above, you’ll have a much better chance of picking people and projects that WIN.