Matt Michaelson

The journey is hard. It’s supposed to be hard. If it weren’t hard everyone would do it and you should surround yourself with people and resources to keep you at your best.


Matt is the co-founder and CEO of Smalls. He grew up in Portland, Oregon before attending Northeastern University to study entrepreneurship, and then moving to New York to work at THINX, where he led growth and digital marketing for its first two years in business (pioneering many of the acquisition strategies used by startups on paid social channels today). Then, Smalls.

Where did the idea for Smalls come from?

Calvin and I noticed that there were several dog food start-ups, but no one seemed to be speaking to the unique needs of cat owners. Having grown up with cats this rubbed me the wrong way. At the same time I prefer to walk down the road less traveled so the stars aligned in delving into this untapped market

What does your typical day look like and how do you make it productive?

Calvin and I start many mornings with a meeting we dubbed breakfast and feelings. This meeting gives us a chance for us to open up and talk about where we’re at without an agenda. From there we’re in the office taking a few meetings with our respective teams and doing some independent work. More and more I see my role as designing the way our team works. We’ve become much more thoughtful about what warrants an email vs. a meeting, how to have a productive meeting and rallying around goals.

How do you bring ideas to life?

Everything starts with our brand filter. There are millions of ideas, but the first step is understanding how they relate to our values as a company. We only take on projects that we know we can handle and do a good job. From there, we prioritize which ideas will have the greatest impact on our customers.

What’s one trend that excites you?

The trend to rethink or question the norms of how a product or industry came about, and do it differently. Take women’s health for example and the explosion in femtech, which is addressing the long history of “shrink and pink” men-centric products. Our analogy to that is the pet food industry has primarily been a dog-first industry and cats have been an after-thought. We believe that by celebrating and catering for cats’ unique needs, we can change this outmoded norm.

What is one habit of yours that makes you more productive as an entrepreneur?

Protecting personal time is key. There’s only so much productive energy in the tank, so it’s crucial to make sure to complete your to-do lists when that energy is there.

What advice would you give your younger self?

Seek out an army of mentors and don’t be afraid to be vulnerable with them. People will see your vulnerability as strength, not weakness.

Tell us something that’s true that almost nobody agrees with you on.

Cats aren’t mysterious creatures. They are perfectly knowable but we haven’t put in the energy to understand them.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Therapy. The journey is hard. It’s supposed to be hard. If it weren’t hard everyone would do it and you should surround yourself with people and resources to keep you at your best.

What is one strategy that has helped you grow your business?

Constant prioritization and editing down to the few things that will really move the needle has been crucial to our ability to grow.

What is one failure you had as an entrepreneur, and how did you overcome it?

Not moving on from team members fast enough. A cliché, I know. The right team, working well together against the right goals is all that matters.

What is one business idea that you’re willing to give away to our readers?

Faire for bodegas. The business of making it easier for businesses to buy things.

What is the best $100 you recently spent? What and why?

Coffee machine. We finally bought one for our office and its saving time and increasing team happiness.

What is one piece of software or a web service that helps you be productive?

Asana. We run our entire business through Asana.

What is the one book that you recommend our community should read and why?

Why We Buy — Understanding why people buy your product on a much deeper level will lead to dozens of new ideas on how to sell better.

What is your favorite quote?

“Don’t ever forget the moment you begin to doubt transitioning from fitting in to standing out.” —Drake

Key Learnings:

  • Building a business is not a science experiment. Sometimes you’ll just have to jump in head first and believe.
  • To build a team you need to understand two things. The first is obvious. What does the business need? I think people talk about the second a little less, which is what kind of people do you need to be around to be at your best and to be happy to go to work every day. If you’re building a puzzle. What puzzle piece are you? Not just on a functional level but an emotional one too.
  • As a consumer business brand is everything. The metrics should follow.