Ariel Diaz - The Artistic Way

A 4X founder takes a completely different approach

This month we have a very different interview. We are speaking today with my friend Ariel Diaz.  Ariel has started four companies in his career, and was most recently the CEO of Blissfully, a SaaS solution that helped IT professionals monitor and manage the all the disparate software being used within their organization. That company was acquired by Vendr where he was most recently their Chief Strategy Officer.

I always believed that there were basically two rough approaches to starting a company.

The first was the deterministic approach. Find a problem, devise a solution, and execute against a plan. Even if the business evolves or certain elements of the plan change over time, the core expression of the original idea holds true. Companies like Square, Opendoor, and Snowflake fit this mold.

The second is the heat-seeking missile approach. These businesses begin with a bit of a hunch, and evolve through testing and experimentation. The idea of the Lean Startup is associated with these sorts of companies. I’d also characterize some distribution-first startups in this bucket, as well as companies that emerged out of hard pivots.

Most startup founding stories I hear tend to fall somewhere on this spectrum.

But Ariel talks about a third way, and I kind of like it.

After starting three companies in the past, Ariel is now taking what he’s calling an “artistic” approach. It’s hard to describe, so I’d recommend just listening to the episode. We talk about lessons from taoism, pursuing projects for their own sake, and having a company drawn out of the founder in a way that seems “suspiciously natural”. We also talk about a couple Steve Jobs quips, including the idea that “artists ship” and that connecting the dots looking backwards requires that you created interesting dots in the first place.

Hope you enjoy this one! I really did, and continue to think about it even weeks after the initial conversation!