Alignment with Co-Founders - Lessons Learned From Past Startups Pt. 2

Last week I wrote about how aligning your idea with your current life situation, skills, and interests is really important.

This week, I'm going to talk about about how important it is to be aligned with your co-founders, which may be the most important aspect of your startup.

Man, have I learned some lessons here.

Mistakes with Dokkit - Getting Married Before Dating

My first startup was Dokkit, a smart calendar app where you can find your interests (e.g. the New York Yankees or the 9:30 Club) and easily download their event calendars to the calendar of your choice.

Dokkit didn't get very far because the co-founding team wasn't aligned at all.

This was completely my fault, because I recruited three engineers to join the team really quickly, and we didn't take the time to feel each other out.

In essence, we got married before dating.

This led to a number of issues.

First, we had different work styles that didn't mesh at all.

Next, all of the engineers had full-time jobs, while I was primarily working on Dokkit. So our schedules and time commitments didn't align.

Finally, we just had different visions of what Dokkit could be.

It's no wonder why Dokkit never got anywhere.

After Dokkit and Ribl

After we stopped working on Dokkit, I wanted to make sure that I had a strong relationship with anyone I might work with as a co-founder in the future.

My next co-founder would be Jeff Thorn, the CEO of Thorn Technologies, whom I worked with on ribl. I consulted for his company (and am now its CMO) for a couple of years before started ribl. So I knew that we worked well together, and we still do.

We launched and grew ribl, and it came and went. Oh well.

After we stopped working on ribl, we worked on deciding what our next startup project would be.

After almost a year of tossing around ideas, we couldn't agree on anything.

Why not? I think this is where our alignment, or lack thereof, came into play.

I was more interested in products in the marketing and sales space, since that was where my expertise was strongest. He and the rest of the team were more interested in building tools for coders, since that is who they are.

I had a bigger appetite for risk. I could go a few months without a paycheck, while Jeff could not.

I wanted to move faster and dedicate more resources to launching a product. Jeff had a services business to run.

So while we're still working together at Thorn Tech, we're no longer working together on a startup.

Conclusion

Bottom line is that you gotta have alignment with your partners.

Do you work well together? Do you want the same things? Are you willing to sacrifice the same amount of time, money, and sanity? Are you on similar timelines?

If one of you wants to build a company that grows really fast while the other wants a lifestyle business, it ain't gonna work.

If someone wants to sell the company within 5 years while the other wants to build a generational company, it ain't gonna work.

If one wants to risk it all while the other is more conservative, it ain't gonna work.

Founder alignment is so important. So don't rush into getting married with a founder. Take the time to make sure you work well together and are aligned on most if not all of the aspects we discussed.

I've made multiple mistakes here. Learn from me and avoid these gaffes!

Have you had co-founder alignment issues like I have? I'd love to hear your story!