Meet Mat Sherman

Mat works at Prenda, a startup that is rethinking education, is the host of the Forward Thinking Founders podcast, and the founder of PubLoft, a content marketing marketplace. Mat was an aspiring musician before diving headfirst into entrepreneurship. Here’s his story!

What is the current project or role that you find yourself working on?

Right now I am working on a couple of things. The thing that is taking up a pretty good chunk of my time is my podcast, Forward Thinking Founders. I interview one founder a day and talk to them about what they’re working on, what their vision is, and try to catch the next Steve Jobs before everyone knows that he exists.

I also have a pretty cool job at Prenda. Prenda is a series of micro schools based in Arizona rethinking education, and I think it’s going to be a giant company one day. I’m pretty excited to work on the team. I still help out with PubLoft a little bit, which is the company that I founded a couple of years ago, and I do some freelance writing.

How did you get here?

In high school, I was still in my music phase. I was a singer-songwriter for about seven years out of my life. I wasn’t really that good, but in high school, I didn’t realize it, and I still thought I was great.

Around the end of high school, I was recording videos, putting them on YouTube, trying to play shows, and trying to get recordings. Then, during sophomore year of college, I realized that I wasn’t that good and I stopped playing music “professionally.” Then I started trying to figure out what I was going to do next. 

I got into videography for about a year. Then I started to dip my toes into entrepreneurship; I wanted to start a social media agency, but never really did anything. Then I started my PubLoft, which is a content marketing marketplace for freelancers and customers to get their blogs managed. That was my true entrance into entrepreneurship, and it was wild. I didn’t plan anything that happened. I didn’t even know I was going to start a company the day before I started it. I just did it out of impulse and what a ride! 

From there, I was working on PubLoft and I scaled it to $5,000 a month, which wasn’t too much. Then I stopped working on it because I couldn’t really do it alone, and I was having some health issues at the time. I decided to start it again with my buddy and cofounder now, Jeremy, and we scaled it up to $25,000 a month. We got an investment from Jason Calacanis, which was awesome, but then we accidentally burned it all to the ground. So now we’re rebuilding it and Jeremy’s taking the reins on PubLoft at the moment. 

In the middle of the downward spiral of PubLoft, I decided to change ideas, which is not recommended. We started GigLoft, a school for aspiring freelancers. We did that for about three months, and we’re still kind of doing it, but there’s zero product market fit and very little traction. At this point, it’s just a cool idea. So, we realized that we had to put our focus back on PubLoft, which is a proven model, and make some money. For a lot of this year we didn’t make any money as founders, and it was a hard year. It was pretty insane to receive one hundred grand from the greatest angel that ever lived, and then burn it in a second. Not on purpose, of course, but it’s just part of the journey.

My podcast comes into this at the end of last year, when PubLoft was doing well, but it was having trouble breaking into San Francisco and the tech scene there. At the same time it was rejected from our Y Combinator for the fifth time. It was at that point that I said, “Alright, screw it. If I can’t get in, I’m going to make my own YC network.” So I emailed 20 YC founders to come on my podcast and I got a lot of them. Now the podcast has almost become a sort of vehicle to break into San Francisco. I have some other plans for it now, but I’ve almost gotten to the point where I don’t even want to do YC anymore because I already have the network!

What are your goals or plans for the next 5 to 10 years? 

I’ll answer this question in two ways. My plan for the next 18 months is to play it safe, pay down a lot of my debt, and try to make decisions that allow me to make a lot of money, even if it’s not that much in equity. I’m just trying to make a lot of money for the sole reason to pay down the debt that I accrued in the last three years, because I dug myself a pretty huge financial hole. I don’t regret it at all, but I still have to deal with it. In 18 months, hopefully I’ll be pretty much debt free and I’ll be able to take some major risks again. By then, my podcast will have become something that I can’t imagine, and I will probably already be working on my next startup idea, which I don’t know what it will be yet. It could be something related to the podcast, but it’s honestly hard to know. 

For the longest time, I knew what I wanted to do with my life. When I was working on Schmooze, my first startup which no one knows about, that was going to be my life. Then PubLoft was going to be my life and GigLoft was going to be my life. And now I’ve gotten to this point where I realize: life is long! For three products, I thought those were going to be my lifelong projects, so life is longer than I thought it was going to be—or it feels longer. So, I don’t know what I’ll be working on in 5 years or 10 years. I don’t know what the company is going to be, but what I will say is I am building the building blocks right now. Those building blocks will then allow whatever I end up working on in the future, whatever startup I build, to be successful. I’m networking, and meeting investors, not to raise money, but just for fun. And I’m preparing for the next thing that I start, whatever it is, to be the one that goes big.

What does growth mean to you?

What growth means to me now isn’t the same as what it meant to me at the beginning of my journey. If I would have heard someone say what I’m about to say, I would’ve called BS. But at this phase in my life, I think growth means failing, and then learning from those failures.

It’s very cliche, and a lot of people say that you have to fail to learn. I still don’t fully subscribe to that idea, because I think some people are too happy to fail. I really hate failing and I’m extremely competitive. I want to win at everything I do, but nobody in my immediate family has started a successful company, I didn’t go to business school, and I was never that great of a student. I’m not supposed to be able to know how to start a company, but I did it anyway and I made every single mistake in the book. I am still making those mistakes, and I have to do that because I didn’t pay my dues by getting an MBA or by learning these things in some other capacity. So I think growth, for me, means trying things that you probably shouldn’t be doing, that are a little out of your league, punching above your weight class, getting destroyed, and then getting back up, standing tall and trying again.  Then once you conquer that league, you try to move up to the next league and you get destroyed, but then you go back and you’ve adapted to that league. It’s just a process, and that’s what growth means to me. 

If you have nothing on your schedule or an unexpected quiet moment, how do you choose to use your time?

My instinctual initial answer is: unproductivity. When I do have a moment, I usually don’t realize it and I work on tasks that don’t matter. The thing that’s interesting is that sometimes you don’t know if the moment is just going to be a moment or if it’s going to be two hours. If it’s just a moment then I don’t feel bad that I’m not reading a book for 20 seconds, but if it’s going to be two hours, then that’s a waste of two hours if I don’t take advantage of it. 

Is there a book, podcast, or movie that has been particularly impactful to your life? 

The “How To Start A Startup” class from 2014 Y Combinator is a lecture series from Stanford about how to start a startup. When I was first getting into startups, it was one of the first pieces of content that I consumed, and it changed everything. It showed me what a startup is supposed to be and how it’s supposed to work. My first “startup” content was from the best startup accelerator in the world and that prepared me to be a force of nature in Phoenix, because my perception of startups was viewed through the lens of San Francisco. If I wouldn’t have watched that when I was first getting into the business, I have no idea how things would have worked out. 

Additionally, when “The Social Network” movie came out, I probably watched it 10 times in a span of a year. Obviously that’s not how it really works, but I just got the shivers watching Mark Zuckerberg take an idea and his skills and bringing people together to build this thing we now call Facebook. I thought it was a beautiful movie about entrepreneurship. It gets me hyped. It’s like my pre-game playlist for entrepreneurship. 

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