Design Leadership in Startups

Soleio Cuervo is more than a chin on the internet. He’s more than an early design leader at Facebook and Dropbox. And he's more than an epic angel investor. 

He’s a truth seeker and truth teller. Or at least the truth as he sees it. 

Soleio was one of Facebook’s earliest designers, joining in 2005 when the company was still finding its identity. During his six-year tenure, he helped shape Facebook’s culture of “move fast and break things,” where mistakes were acceptable but slowness was not. This philosophy was crystallized during the controversial launch of News Feed, which showed that transformative products could succeed despite initial user resistance if the team moved quickly to address concerns.

After Facebook, he joined Dropbox, first as an angel investor, then full-time in 2012 to lead design when they had just a handful of designers. The transition revealed stark cultural differences - while Facebook was a paranoid, competitive insurgent focused on speed, Dropbox prioritized reliability and stability, aiming to build “space shuttle quality software.” This experience taught Soleio how company culture gets set early and is deeply influenced by the business model and founders’ personalities.

Following his operational roles, Soleio had great success an angel investor before building Combine, a hybrid venture firm and design studio. However, the “Happy Meal” approach of bundling investment and services proved too complex, creating role confusion when advising founders. He ultimately returned to angel investing, finding it provided more authenticity and freedom to give direct advice without the constraints of managing outside capital. His investments include Figma, Vanta, Vercel, Replit, Perplexity, and many more. 

The parts of this conversation I find myself continuing to reflect on are just how formative company cultures are and how often that's taken for granted by otherwise overwhelmed entrepreneurs. In our first post about indie we wrote:

Like cement, the cultural foundation for new projects and companies sets early. Those who focus on raising outside capital and achieving fundable milestones have a very difficult time getting off that VC treadmill.Those who focus on creating value for customers and generating positive cash flow from the very beginning are able to make their own decisions independent of competing outside interests.

This is true of fundraising, product, and execution. As Soleio says so eloquently in this conversation - Culture is the deepest moat one can create. 

The "culture of Soleio” seems to contain a bunch of contradictions — care for craft with an obsession for speed. A clearly massive ambition coupled with a desire to be a “trim boat” that can be lean and focused. 

With Soleio, you can’t spell culture without CULT, and in this conversation, he mentions a piece of writing that had a profound impact on him that we would be remiss not to share here: 

The Cult of Done Manifesto by Bre Petis and Kio Starks

There are three states of being. Not knowing, action and completion. 
Accept that everything is a draft. It helps to get it done.
There is no editing stage.
Pretending you know what you're doing is almost the same as knowing what you are doing, so just accept that you know what you're doing even if you don't and do it.
Banish procrastination. If you wait more than a week to get an idea done, abandon it.
The point of being done is not to finish but to get other things done.
Once you're done you can throw it away.
Laugh at perfection. It's boring and keeps you from being done.
People without dirty hands are wrong. Doing something makes you right.
Failure counts as done. So do mistakes.
Destruction is a variant of done. 
If you have an idea and publish it on the internet, that counts as a ghost of done.
Done is the engine of more.
You may be piecing together a theme here that I hope comes through loud and clear here. 

Accelerating your time to done is the ultimate informant for what’s next. If you can master that loop, you’re well on your way to having the impact in life and culture that you aspire to. 

This conversation with Soleio is a good reminder of that, and I hope you enjoy listening as much as we enjoyed recording it. 

Happy New Year!