Why did you choose to freelance? How did you get started?

Honestly, freelancing was the most obtainable path that I saw  to quit my job and work for myself. I had a knack for writing, a drive to work with startups, so I combined the two and started getting clients. Soon after, I built a company around those efforts called PubLoft. Once I had the name and domain, I had the "business owner mindset" and got 20+ customers through cold email to get it off the ground.

Who is your entrepreneurial inspiration? How did you find out about them?

My big inspirations are Gary Vaynerchuk and Sam Altman. These were the two people who who I was into at the same time I was getting into startups.

Gary taught me to just get in the game, and showed me the qualities that a good business person should have. He's also just a hype machine, and when getting started, sometimes you need a hype machine to keep you going. I heard about him through his book, Jab, Jab, Jab, Right Hook.

I learned about Sam when I heard he took over Paul Graham as President of Y Combinator.

sam altman y combinator open ai
Sam Altman

Sam taught me how to be a good startup founder. Right after I got into startups, I watched the class he put on at Stanford backed by Y Combinator—How to Start a Startup. This is when I was thrown into the deep end of startup land. I’ve learned more about startups from Sam and YC than all other sources combined.

What’s your biggest pet peeve?

I strongly dislike when people complain about things not being “fair,” even though free markets by definition are objective. Complaining can make someone feel better in the moment, but objectively, it does nothing to advance them to where they want to be.

There are those people who turn lemons into lemonade. Then there are the people who take lemons and squeeze them into their eyes. My question is why?

What are you currently reading?

I’m reading High Output Management by Andy Grove, the founder and long-time CEO of Intel. So many VCs recommend this read to their founders—I now understand why. It’s showing me that there is a science to management, and that Andy cracked it before everyone else.

What’s your favorite holiday & why?

Halloween, because I get to dress up in funny outfits and eat candy. What else is better than that? 👻

Yep, that’s me in an American flag suit.

Where do you live? Would you rather live elsewhere?

I live in Phoenix. I would rather live in Colorado and hike 14ers or in live San Francisco and build out my network in tech. One step at a time. 😋

mat sherman hiking 14 thousand foot mountain colorado
Me hiking a 14,000 ft mountain in Colorado!

What’s your top advice for freelancing/self-employment?

Keep an even keel. When things are going well, try to curb your excitement. When things are going poorly, just know that they aren’t as bad as you think they are. The more even-keel you stay, the more rational your decisions will be.

Jeremy calls this “tightening your suspension,” like with a vehicle, so you don’t feel so out-of-control during the twists and turns of entrepreneurship.

I’ve been working on this personally, and always happy to talk about it with others who struggle with the mental/emotional challenges. I’m here to talk!

Thanks for reading! Hope to read your story one day :)


Mat Sherman is a cofounder and the CEO of GigLoft.