3 Things I Learned from The Keys Podcast Guests

This content was originally prepared for a discussion I was a part of at Chaco’s HQ during their team building week. I’ve adapted it for a blog post.


Q (Chaco Josh): Tell us about The Keys. How did it come about and where did you get the idea for the podcast?

A (Josh Perez): People have been insanely kind to me in my own journey, and I have had some things happen to me in my life, where I just felt that I needed to give back in some sort of way. I’ve had some some hardships too, but I couldn’t keep all the good things to myself. The podcast is a way for me to give something back to the world for free. I hope it helps our audience develop and grow in their own journey to becoming key players.

I also spent years listening to podcasts or reading books about startups and founders which sort. of frustrated me, great brands become great because of the people behind them. I’m not trying to knock founders and all of the hard work and risk they put into starting these companies, but you don’t scale without amazing people. And their stories matter.

I remember listening to a story once, of this intern at Lyft, who came up with the name. Lyft was previously called Zimride, and Harrison thought it was horrible so he presented the founders a new idea. What the heck happened to Harrison, what is he up to these days?

Q (Chaco Josh): You’ve interviewed some incredibly distinguished and talented individuals from well-known companies. Who are some of your stand-out guests? And what would you say are the values or qualities that set apart these key individuals from the pack.

A (Josh Perez): Roberto Ortiz was the first person I ever interviewed for the podcast. Roberto is from Philly, from the hood of Philadelphia. Grew up with a single mom, five kids, his dad had passed as a child. He wasn’t set up for the “American Dream,’ we can say that. 

But at 14 he bought his first computer and taught himself how to design and how to do basic coding. At 16 he was recruited by Lockheed Martin. He eventually started his a fantasy sports app on the side that was acquired by Yahoo. He was recruited by Google at around 28-29, ended up working with Surgey Brin, Co-Founder of Google. 

What stands out to me about Roberto is his vision for the world as a better place. He now does a lot of work to empower minorities in the tech industry. Obama administration had invited him to be a guest at the White House, and he’s doing amazing stuff with non-profits in South America to help build tech down there.

As for the three things I have learned from our guests on the podcast:

They all cared, they had enough integrity to care. - What I mean by that is that they owned their positions without anyone having to tell them to. You have to care.

Mackey Saturday was a middle school teacher who stepped down because he knew he wasn’t serving kids well if he wasn’t passionate about his teaching career. He taught himself graphic design and worked his tail off until he ended up ultimately designing the Instagram word mark. 

Mackey later became a principal at NYC design firm Chermayeff & Geismar & Haviv. He was on track to be a partner. But, after three or so years, he cared enough about them and their clients to step down, because he knew it wasn’t the best fit for him. There is a difference too between quitting and stepping down in the way he did it.

Take ownership of whatever position you’re in. If you’re going to do something, own it. 

Be curious. Embrace the growth mindset.

“Just enough is not enough.” - Roberto Ortiz

Don’t just settle for whats in front of you.

Roberto went back to school when he was 26 and decided to get a business degree because he had already developed himself as a designer. And it was hard, it was a whole new subject. The easy route would’ve been a degree track for design. Be curious and don’t settle.

Take risks and make the right sacrifices.

You have to weigh the risks for yourself and know when it’s the right time to make those sacrifices, but be willing to do so.

“For anything great to happen, you have to be willing to make choices.” - Mackey Saturday

I also think about Ben O’Meara, who moved to San Francisco from the Northeast to be an early employee at Huckberry. He left the finance world and took the risk because he found a company he believed in. 

Q (Chaco Josh): Any parting wisdom or parting thoughts to leave with this group?

A (Josh Perez): I’m going to be cheesy here and use a quote from the office …

I wish there was a way to know you’re in the good old days, before you’ve actually left them. - Andy Bernard, from The Office

It’s easy to get caught up in the day to day and not be aware of the magic thats happening around you. Especially if you’re not in the field. 

I guess for parting wisdom, remember to take a step back be aware, cause you might be in the good old days.