A 25-Year-Old Entrepreneur’s Guide to Going Big

By Liza Corsillo
Photos by Jace Lumley

It’s a rare thing for a 15-year-old boy to spend his free time meeting with clients and building his dream career. But that’s exactly what Reilly Newman was doing in high school—on top of swimming, running cross-country, redesigning his school’s newspaper, and competing nationally in graphics and communication through SkillsUSA. The now 25-year-old business owner, husband, and father got started early in the world of graphic design, and his hard work has more than paid off. A self-described brand artisan, Newman transforms businesses into full fledged brands and helps regular people (lots of them) get their foothold in a market driven by social media and lifestyle storytelling. He also spends a fair amount of time giving back to the community that helped him get his start—Paso Robles, California.

But for a man who on the surface seems incredibly traditional, Newman got to where he is today by ignoring convention and making himself the squeakiest wheel in all of central California. And in a world where most people his age eat, drink, and sleep on their phones Newman’s old-fashioned values are pretty darn refreshing. We picked the young workaholic’s brain for professional gold nuggets any man in any industry can use. Be warned: Newman doesn’t believe in shortcuts to success. What he does believe in is incremental progress and learning from failure. Here are seven lessons from our new favorite creative.


1. Don’t Be Afraid to Email, DM, or Straight Up Call Your Heroes


“When school would get out, I’d go have a client meeting, then go home, bust out my homework, and then do client projects. I got accepted to Westmont College down in Montecito, California, and they told me that my business was already up and running and that if I came there they would essentially be teaching me what I was already doing. So I gave myself a year to grow my client base and not go to college. I reached out to those who would have been my professors and asked for the curriculum and what books to read and they actually sent it over. So I just read and read and read and I had a couple of mentors along the way and my business has grown year over year ever since.

“I’ve had phone calls with the old CEO of Starbucks and I’ve talked to Seth Godin who’s the most popular marketer alive. I was literally 15, 16, 17 years old and I was emailing people like James White and other big designers. My strategy was to just be the squeaky wheel. Like, ‘Hey, I’m a teenager and I want this information. I’m curious what books should I read?’ Starting to write these emails I was pretty young and this was before Instagram [Newman now boasts a healthy 13K followers]. Since then I’ve gotten better and better at it.”


2. Commit to Your To-Do List

“In high school I would make to-do lists, and the way I would go about doing my school work was different than a lot of the other kids. To this day, I write a to-do list every day on paper. I remember when I was like 15 or 16 I heard Sarah Blakely in an interview and she said ‘I just focused on doing two or three things that would get me closer to my main goal, just do two or three of those things every day.’ So whether it’s inch by inch or maybe you move a foot one time, it’s about that constant dripping water hollowing out the stone. That’s where a lot of people lose it. I’m 25 now but I’ve been in big meetings and had experiences that a lot of other people haven’t had and worked with people who were literally twice my age. So I had to either jump in and do it, or just get out because I was playing in a league that I was kinda not supposed to be in.”


3. And Your Reading List


“I don’t waste time watching or reading the news. I’ll get most of that from Twitter or some other digested form. But I read a lot, two or three books a month. I listen to a lot of podcasts. I can listen to podcasts while I work on logos or admin stuff and still be able to digest the information because it’s not visual in nature. I like “Freakonomics” or “Planet Money.” I don’t really enjoy industry-specific podcasts because they’ll just talk about the same things over and over. But I do like more psychological and abstract ones as well as ones that are more business based because I work with countless clients in totally different industries and they have totally different problems. I’ve learned how to solve problems that apply to lawyers and dentists and everyone in between. All these mysterious ways that things coexist in our economy and interact is just fascinating to me.”


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4. Invest in Local

“I love investing and I always think long term with macro vision. I think the Central Coast in California has the most upside in growth. Los Angeles and San Francisco are still growing, but I do feel like they’re almost tapped out. So Paso Robles has huge opportunity; we’re halfway between San Francisco and L.A., and I love being able to get people to see what’s possible here. I’m on the executive board for the local chamber of commerce, so I’m able to be part of the community and help improve the livelihood of local people. I’ve been talking with the mayor and the city planners about growing our city and doing things to boost small businesses and the wine industry so we can actually help them win in the long run.”


5. Redefine Work-Life Balance


“When I’m with my family I’m with them 100%, and when I’m at work, I’m working 100%. You know all this talk about work-life balance, there’s no such thing. You can’t win in both areas, because it just doesn’t work like that. I’ve been doing this for more than half my life—literally. There are sacrifices and my wife totally understands that I’m entrepreneurial and that I have to do these things, but I also want to be there for my kids and for my wife and make sure they’re happy and safe and comfortable. So, I would say it comes down to that discipline and that grit that we talked about. I’m a workaholic by nature, and I know I can’t expect that out of others. Like over the weekend I was working and got three and a half hours of sleep Friday night, four hours of sleep Saturday night. I know that that isn’t the average, especially for someone who’s 25.


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6. Get Comfortable with Failure

“I don’t think you can teach entrepreneurship. For the most part entrepreneurs have that grit mentality. Failure has to be seen differently. To me failure’s just part of the road to success and the people who are afraid to fail won’t ever start on that road. I think creativity is a muscle and we’re all given the gift, but it’s about working it out and seeing where you thrive and pushing it to the next level. For my daughter (and for our next kid on the way), I want to give them as many opportunities as possible but still help her realize that failing can be a good thing. Because what I’ve learned in my failures has been life changing.”


7. Find Your Menswear Uniform and Stick to It

“I keep things really simple. My dress code is that I maintain a certain feel and vibe, I have just a handful of different things that I’ll throw together and it’s like my uniform. I think that’s how you become more memorable. You keep a certain style in place and people associate that with you. It also helps with productivity; there are studies that show that putting on a uniform helps you set your mind in the right direction and says to you OK, it’s work time now.’ I also wear an analogue watch every day because I want to balance being contemporary and young with a kind of timeless professional style. I think it’s a very consistent statement piece that a lot of people have taken for granted.”