Jacob Goodman (Edition # 2)

Jacob Goodman (Co-President and Owner of Fresh Prints)

** Please note that when this interview was released, The Takeoff was called Casting Ventures. We have since rebranded to The Takeoff. **


We are excited to release this interview with Jacob Goodman (Co-President and Owner of Fresh Prints) as The Takeoff: Edition 2.

If you’re a student looking to get involved with the Fresh Prints Campus Manager program, apply here.


Michael: To start off, how did you come to find yourself interested in the world of entrepreneurship? And, if you can remember, what was your first entrepreneurial experience?

Jacob: I went to college at Washington University in St. Louis, which is definitely a very pre-professional school. I remember I felt all this pressure of what I was going to choose as my major and, subsequently, kind of my life from the first day I arrived on campus. So, I just ended up thinking, while everyone from New York is in finance and it seems like a lot of people from WashU go into finance, maybe I’ll go into finance. At the time, I asked myself if I even really knew what a career in finance meant and realized the answer was no, which got me kind of alarmed. 

That was really when I started thinking about what I wanted to do critically, and what I knew about myself. Through talking with other kids older than me at school, I started to fall in love with the idea of entrepreneurship and building something from the ground up. You know, WashU obviously has a fantastic StEP program (the Student Entrepreneurial Program) that helped accelerate how quickly I was able to get into it. I definitely owe a lot of credit to the University for that.

Michael: Awesome! I know that you were involved with and even ran several companies while still in school. Could you maybe explain a little bit about what your experiences were like running those businesses and what it was like running commpanies while also having class?

Jacob: Well, this definitely isn’t good advice, but the whole class piece definitely fell off for me, especially towards the tail end of school. At first, I came in and was super motivated, particularly when I thought I wanted a career in finance. I was super motivated to do well academically and did well probably for my first three semesters. After getting involved with UTrucking and getting involved with Fresh Prints, I ultimately stopped going to class quite as much and really began putting a lot of emphasis and energy into the businesses.

Michael: What was your favorite part about being involved with those companies while still in school? What made you really interested and motivated to get involved while you were still a student, whereas some other people may want to wait until after they graduate to get their first experience running a business?

Jacob: The first great part is that it felt like we could fail and it wasn’t going to matter. Right? There are obviously a lot of downsides of running a business when you’re in college. From a skill development standpoint, we didn’t really have any skills. From a capital standpoint, we didn’t have any capital. From even a network standpoint, when it came to hiring other people, we didn’t have a network. So, that was very difficult. But, the freeing part was that we felt truly like we had nothing to lose. If it all went to zero and we had to either shut down the business, then that was alright. As students, we didn’t have a family to feed, and we were very fortunate that our parents were paying for the majority of our lives, which was definitely a very freeing component.

Michael: Off of that, do you have any advice that you would give to someone who is a student now who is either (A) working on a business or idea now or (B) interested in getting started with something but doesn’t quite know if they’re confident/comfortable enough doing so while also being a full-time student?

Jacob: If you would have asked me this question a couple years ago, I would have been very, very firm on the advice to just take a leap of faith, jump in headfirst, and go forward in college. At this point, I definitely think the answer is a little more nuanced. It definitely depends on the individual. Obviously, the best thing you can do if you’re really interested in entrepreneurship in college and want to start a business is talk to peers and surround yourself with people who are starting businesses or have started businesses. These types of people exist on every single campus around the country. Just through talking to those people, you can figure out if there’s an opportunity to work together on something.

I honestly very rarely hear people take the path that I took where they purchase a stake in the business as their first step, but you know, I think that’s an option that people can look down, too. You can buy a very small business, get a couple partners, and try to see if you can raise some money from friends and family or get a loan in some way. It’s obviously a route that is not commonly traveled in college, but that’s what we did and it worked for us. So, I do encourage people to take a look at that potential route as well.

Michael: Really great advice there! I’d love to find out more about what you’re doing now. Could you discuss more about what you’re currently working on and maybe give a glimpse of what your day-to-day looks like?

Jacob: I am currently one of the Co-Owners and the Director of Sales for Fresh Prints. We are a custom apparel company. We print any apparel or promotional products that primarily collegiate organizations need decorated but also do a lot of corporate work as well. We have a team of 70 full-time employees and have a Campus Manager program of just over 300 Campus Managers across the country, who are responsible for a large portion of our sales.

The Campus Manager program is meant to be a platform for student entrepreneurship. We try to find students, kind of relating back to your last question, who are very interested in entrepreneurship, very ambitious, and want to take that first step but don’t really know where to look. The Campus Manager program is meant to be that first step into entrepreneurship.

We aim to teach the foundation of business development and sales to our Campus Managers, which we ultimately think is the cornerstone of pretty much any venture. As the Director of Sales, I oversee that entire team. All the Campus Managers report up to Business Development managers, who report up to me.

Michael: If a student wanted to get involved with the Campus Manager program, how exactly would they go about that?

Jacob: We’d love for students to get more involved. On our website, at the bottom in the footer, there’s a link that says “Apply to be a Campus Manager.” You can fill out that form and enter your information. You’ll then be scheduled for an information call, where you learn more about the position, what the expectations are, what the commitment is like, and some of the things we think you’ll get out of the role. Then from there, a potential Campus Manager will go through our application process and then subsequently our training process, before they’re actually launched live into the position.

Michael: I hope that many of our followers are interested in getting involved with the Campus Ambassador program and check out that amazing opportunity. It seems like a really amazing way for students to get involved with entrepreneurship and to get experience growing something while still in college. 

What has the growth looked like so far for Fresh Prints?

Jacob: I’ve been running the company with my partner Josh for eight years. Time flies! When we initially purchased Fresh Prints, and I definitely use the word “purchased” lightly as it was a very small company at the time, we’re about 50x in terms of revenue growth. In terms of headcount, at the time we had three Campus Managers and nobody full-time, and now we have 300 Campus Managers and 70 people full-time. So, the team has grown quite a bit too

Michael: And, where do you see the company in maybe five or ten years?

Jacob: I think that’s a really interesting question. We don’t do any ten-year planning. We only do five-year planning. Ultimately, maybe you can make the argument that we should actually do ten-year planning, but so far, historically, we haven’t. 

There are a couple of big pillars of the business that we want to grow in the near future. While we currently have 300 Campus Managers across 200 campuses, there are about 1000 qualified markets across the country that we want to hit. Expanding out our Campus Manager programs is certainly a big part of the next five years. We’re also working on some very different stuff on the e-commerce side that I can’t say too much about right now, but a presence there is definitely a big part of our five-year plan.

The final piece is the growth on the corporate side. For us, the inside sales team is a fairly recent development. We’ve really only started doing it in the past year or so. We are now actually building out an SDR program to support and feed those inside sales reps. That’s a big part of the business that we want to grow and make up a much larger part of our revenue from moving forward.

Michael: I’ve really enjoyed learning more about Fresh Prints. I know that you are also involved with some investing, and I’d love to learn more about your experiences on the investing side of things.

Jacob: Sure. There are really two main projects that I have invested in. One is like you said, College Truckers. The CEO Max and his team are remarkably talented. That was definitely a direct extension of UTrucking and the work we did in college. College Truckers is based out of Brooklyn. There is obviously a lot of overlap with Fresh Prints and College Truckers in terms of the market we address. Watching them grow has been really great. 

The other investment I made was actually also right out of college. It is a company called LeafLink. I made this investment four or five years ago. My partner Josh and I originally invested in their pre-seed round. LeafLink is a B2B cannabis marketplace. When LeafLink originally launched four years ago, the space was just Colorado. The company really wanted to serve and be the provider of the infrastructure for the entire industry as it grew. We were really excited at the time about the founder and everything they were doing. LeadLink recently closed a $35 million round with Thrive Capital. They’ve done great and have a remarkable team. It has been really cool to watch everything that LeafLink has done thus far.

Michael: That sounds amazing, and it’s obviously wonderful to be able to be involved in a company at such an early stage, at a pre-seed round, and then have that company go on and raise a much larger round later from an incredible investor such as Thrive. I know that you touched on the point of the founder of LeafLink being a big motivator in why you invested. How important do you think the founding team is for early-stage companies in terms of being able to to determine whether or not those companies may have success? I guess, the question more so is: How important is a great founding team versus a really great idea?

Jacob: The team is obviously very important. It’s the only real thing you have as an early-stage company. For every idea that is out there, there are lots of companies pursuing that same idea. At some point, the only explanation for the variance in success is the founder and the team. That idea, in and of itself, I think is obvious to pretty much any investor. But, the difficult part is actually: How do you go about about evaluating if the founder is right? That’s definitely not easy, especially if you’re willing to invest. At the time, Ryan (Co-founder & CEO of LeadLink) was a very young founder who had a successful exit under his belt but was 23. I think that’s the difficult part. 

Trying to spend a lot of time with the founders that you do ultimately invest in is really important. I had the opportunity to get to know Ryan basically over the course of a year before he started LeafLink, so I was pretty confident in him by the time he was ready to launch.

Michael: Great! I’d love to learn a bit more about some of the people who’ve inspired you to become the person you are today. Are there any one or two individuals who you could pick out who have been the biggest influences in your life as a whole or in your success so far in the business world?

Jacob: It’s a loaded question — there is a very long list of people that I would point to. Let me try and focus on the answer though. Definitely my partners, Josh, who’s our CEO, and our Director of Growth, Jolijt, are both phenomenal. Both Josh and Jolijt are good at very different things than I am. Josh, for example, is kind of your classic leader. He’s very good at navigating the people piece of organization building, and how you really think about building an engaged team. Jolijt, on the otherhand, is really just one of the strongest intellectual minds I know. It seems like whatever problem you throw in front of her face, regardless of how large, she is going to find a way to work through it and solve it. They’ve been two huge pieces of inspiration. My partner in College Truckers, Max, is also a fantastic leader. Max and I worked together at UTrucking while in college, and I’ve learned so much from him.

I would also say my dad. My family has all been entrepreneurs for the past couple generations, and from a very young age, even though I might not have realized it, my dad was kind of instilling some of the fundamentals of how you think about an organization and just kind of values that a great company should have. I definitely owe a lot to him.

Michael: It’s amazing that you come from a family with generations of entrepreneurs. That’s really wonderful. Alluding to both Max and the team at Fresh Prints, discussing the importance of having teammates with complementary skill sets is awesome to see there. Before we finish up, I have two quick questions that I really like to ask that are actually off of the business side of things and on a more personal side. These questions touch on mental health and wellness, given this is something that is really taking a big role in the world of startups and entrepreneurship and is, in my opinion, super important. 

Outside of Fresh Prints, do you have any hobbies and passions where you spend a lot of your time?

Jacob: I’m fairly comfortable being open about this because I feel like it plagues every founder. If it doesn’t, maybe they have some sort of superpowers. The mental health part and the wellness piece has definitely been difficult. Over eight years, we’ve obviously had times that were fantastic, and we’ve had times that were really difficult. The part that I still have to get a lot better at is not riding the waves too much and decoupling how much my mental health and wellness is tied to that specific point in time for the company. I don’t necessarily think I have a great answer there. And, if anyone else has a great answer there, let me know because I’m down to hear. It’s definitely tough. I try to surround myself with people who make me happy and who I enjoy being around.

Michael: Is there anything that you do to stay on top of the mental health and wellness aspect? I often meditate using the app Calm, and I think it’s really had a huge impact on my life and in my ability to control my emotions in situations where previously I may have become very stressed. I’m wondering if there is anything that you kind of turn to in stressful situations?

Jacob: I definitely started going to sleep earlier. In college, and for the first two years out of college, we were up every night until 4–6am. Usually six. I never do that anymore. No even close. That has probably been the one largest change that I personally made that has made a big difference. Another thing is that I don’t work on Saturdays anymore. I think that’s important. I was never particularly religious, and I’m still not, but it’s funny that the Sabbath kind of now all makes sense to me. So, we try to not work on Saturdays.

Michael: Awesome. Well, that’s all the questions from my side of things. Before we finish up, if there’s anything else that you’d like to touch on, I’d love to leave the floor open to you right now.

Jacob: Anyone who wants to reach out to me can email me at jacob@freshprints.com. I will either respond the same day or the next day, so I promise I’ll get back.


** PLEASE NOTE THAT OUR INTERVIEWS MAY BE EDITED FOR LENGTH, CONTENT, AND CLARITY**


Moderator: Michael Spiro (Founder at The Takeoff. Student at WashU. Incoming Summer Analyst at JMI Equity)

Fresh Prints Campus Manager


Share The Takeoff