Forked: Founder vs. Early Employee

It’s funny how much hero worship there is out there about being the “founder” of a startup company. That’s not to say I don’t appreciate it – to some degree. But the reality is that how different is it to be the “founder” or the first group of folks to really put your shovel in the ground versus on of the early team to pour the cement, build the frame and get a roof on that building?

Is it better to take your shot as a founder or join up as an early employee?

For me, I’ve wondered about that question after announcing I was leaving Zaarly. Lots of great folks have asked if I’d join their company, go to the dark side (as an investor), cofound something with them or simply help lead something that was moving up the hockey stick. All of these were great opportunities and things that made me pause. In some ways its that proverbial “fork” in the road for me and my career. And so I’ve been forced to ask, “What makes sense for me at this point in my life?”

The last part of this is where I found the most insight: ‘at this point in my life.’

And here’s what I’ve realized: founding something is a great learning experience. It truly truly is. BUT, I learned more about how to found something from my experience at Appature (learning from the founders Kabir aand Chris who’d closed their Series A a few months before I joined) and working with dozens of founders as a lawyer. And now as I start the process of founding my next company, I realize how much collectively I learned going through the process at Zaarly and all those experiences before.

So it isn’t if you should found something, but more like when… and if you think about your journey as a founder in those terms, turns out its much easier (non) choice you’re making.

So, Which Fork?

Obviously, I don’t pretend to sit here and give prescriptive advice to anyone… turns out startups are a challenge whether you found it or you join it early on. What I’ve learned about myself is that as a founder you must be able to be a teacher and inspire confidence. From my first hacky side project startup to Zaarly to my new project, each time I’ve gotten more confident, more experienced and more knowledgable. That isn’t to say I can control the outcomes any better, but perhaps I’ll just make fewer of the same mistakes… again.

As I thought through my opportunities, I asked myself these questions:

• Are you able to teach others that work with you something?
• Can you lead people towards an ambiguous aim?
• Will you be better able to convince others to follow your lead in one to three years?
• Are you convinced you are ready to take this shot?
• Do you have the resources (time, money, support) to go for a while without a paycheck?
• Describe how this fails? Does that scare you from doing it?

All of these come down to the question of timing (and confidence in that timing answer), in some form of another. Maybe it’s now or maybe it’s later, but most of these are experiences, skills or resources – and all of which require you personally believing now is the right time.

For me, I decided to forgo other opportunities because it feels a little like I’ve been preparing for this for my whole life… and that’s the answer I needed to know I was ready to go back out for another swing.

Turns out, it’s hard. So don’t make it harder.

So do you found or not? I think the answer is yes (if you are asking the question), of course you found… but the question really is about when do you found it. That’s not easy to know, but it’s something that will become obvious as you begin your journey. If you are confident you want to found something, make your journey about answering those questions – with the right experience, knowledge, connections and resources.

The truth is, I love startup people and the guys and gals I meet who are taking the risk to do a startup. But I often wonder why there is the infatuation with being “the” founder and not part of that early early team? It’s lessons learned doing the startup grind that ready you to found – but rather than “pay their dues”, people move forward with founding. I wonder if you’d get more out of learning from a successfully founded company than struggling through your first one without any prior experience. Not every situation is the same, but there are some very common lessons along any startup journey.

For me, I’m totally enjoying the process of founding another startup. I truly am. It’s way harder than I remembered, and takes extreme patience, but that’s okay. At the same time, each day I realize how MUCH I didn’t know just a few years ago before my first startup. Little things like tricks, timelines, structures, hacks, shortcuts, mistakes to avoid, quirks, etc. You can get some on the fly, but others are just so much easier learning from/with others.

Life’s all about preparing you for that moment.

It’s awesome to see all the enthusiasm for starting companies – we probably have a few guys like Steve Jobs, Mark Zuckerberg and Bill Gates to thank for that. But if you look at their journeys, they each had figured out the right time for them to found something… whether than meant putting in the time in school, in another company, via a hobby or just in life.

But founding a company isn’t about if, its about when. And if you know you want to do it… create that plan and that path to actually do it.

Cuz it’s terrifying and awesome on this journey. Wouldn’t be anywhere else.