Jonathan Smalley

Jonathan is the Co-Founder & CEO of Yaguara, a platform that helps commerce companies create a single source of truth for their teams, using real-time data and predictive analytics. Yaguara is backed by Foundation Capital, Gradient (Google), and the founders of Warby Parker, Harry’s, and Allbirds.

On his morning routine.

I naturally wake up between 5 and 5:30 most days.

Ideally I’ll meditate right away, followed by a coffee and a quick workout. Then I dive right into my email workflow while planning the first few hours of my day. 

I also like to wake up my wife, Grace, by making her coffee. This is the singular constant in my morning ritual no matter what’s happening in the world.

It’s our sacred time.

On fitness as a reset.

As a result of the pandemic, I’ve definitely had more time to workout.  

Most days I’ll do yoga or head out for a run, and more often than not that workout’s pretty early in the morning.

Though I’ve recently begun taking breaks throughout the afternoon for a quick walk or workout, which is equally useful for sweating out frustration or stress.

It’s critical to find time in my day to press pause, breathe, and reset.

On his source of ambition.

My motivation comes from a couple of places. 

I’m the youngest of four, so I was always competing against my older siblings. Sibling competition, along with intrinsic motivation, really informed my competitive nature. I got into tech when I was young and was consulting by the time I was in high school. 

My father is a major source of inspiration. Growing up, I saw how my dad, who’s incredibly smart, was always stuck and frustrated at crappy jobs. 

Companies would pass him up for promotion even though he worked harder than most. This really inspired the mission behind Yaguara: help people find a better way to work so they can make an impact while building truly meaningful things. 

My grandfather was also a huge source of inspiration. He was always identifying new opportunities and constantly learning.

My great-grandfather was an abusive alcoholic, so my grandfather realized pretty early on that he had to step up and support himself. 

He started working on the railroad when he was 14.

Then he fought in Korea and used his GI bill to start an electrical maintenance company. Today, that company employs over 150 people.

On customer centricity.

I’m a product person at heart, so doing consumer research is something I enjoy.

I love talking to customers about products and solving their pain points.

It’s just fun for me. When I’m focused purely on solving problems, it feels less like work and more like play.

Whenever I’m stressed out, I focus on a product and think about design. I always ask myself, how can I improve the design’s functionality and reduce frustration for our customers?

On his evening routine.

I always kick off my evening with a nightcap, usually wine, whiskey, or a cup of tea. Then I’ll sip it as I finish up my emails and wrap up work. 

Most nights I’ll throw on a movie or basketball in the background. Around 10 or so, I put away all my tech and screens and switch on do not disturb. Then, my wife and I block out time to just hang out together.

We’ll run through our days and just talk and relax. When I make time for each of these rituals, I sleep really well.