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Jason Shuman: One Quarter Life Crisis Away from Venture Capitalism

Takeaways

  1. Be wary about identifying too strongly with your business, it could lead to an identity crisis.
  2. If you’re not sitting down, reflecting, and processing, you’re just letting life go by.

Jason Shuman is founder-turned-investor who’s on a mission to empower others with the confidence and tools to live a more fulfilling, successful life. Jason has been an entrepreneur for as long as he can remember. In college, he launched a direct-to-consumer footwear company that sold hand-sewn boat shoes and driving moccasins. He later went on to work at New York-based seed fund Corigin Ventures, where he invested in several companies, including the recently public enterprise smart lock company, Latch.

Currently, Jason is a Partner at Primary Venture Partners and has been working in New York as a VC for the past six years. He’s passionate about working with founders that impact consumer behavior and daily living. In 2019, he was named Forbes 30 Under 30 in Venture Capital and was listed by the Venture Capital Journal as one of the top 40 rising stars.

Transcript

BRYAN WISH: What is the One Away Moment you want to share with us today?

JASON SHUMAN: It will be about landing my job in venture which was after a very long and windy road. 

BRYAN WISH: Why was it such a significant milestone for you?

JASON SHUMAN: I grew up outside of Boston and my family were a lot of entrepreneurs, and my mom was a therapist. I became super interested in startups and technology when I was a kid. In middle school, I was writing business plans for mobile payments on flip phones. Literally mass text messaging back in 2004 and getting shuttled in the city to meet with founders. I always knew that I wanted to be a founder and wanted to start companies and I did. I started my first company while I was in undergrad.

It was a direct to consumer footwear company that I started with my best friends; three of my best friends and my brother. We bootstrapped the thing during my senior year of college back in 2012. It was a ride. I learned a ton of lessons. It was like really good timing. I think we chose a mediocre market being the direct to consumer footwear market for a variety of reasons. It was pretty poor execution; much of which I will certainly shoulder the blame for.

Throughout my college years and my teenage years, everybody looked at me as this kid will start companies. He’s going to be an entrepreneur. When you start a company and start making noise, whether in your local community or your college or a city, you start to really identify with who you are as a person with that company or that thing. About 1 ½ years out of school, after I graduated, I was living up in Boston. I was feeling super burnt out. I remember not thinking about the company in the shower anymore. I was like, “I think we’re done.” What do I want to do next? I certainly tried to look out for the other people working with me first, and then I was worrying about my steps. 

Sitting there as a 23 year old who people looked up to as an entrepreneur and really having an identity crisis was a very challenging point for me. That’s where I’d say the big fork in the road started. I had to start reflecting big time. 

BRYAN WISH: I love the vulnerability and quarter-life crisis. I can relate in a lot of ways. Did you feel pressure in how you grew up, going out, and doing something with your life? Was there pressure to be an entrepreneur? Where did that internal drive come from?

JASON SHUMAN: My parents never really pushed me to do something. If you ask them, they’d tell you I’m always free-flowing and I need to kind of go do whatever it is that I want to go do in order to really be happy. Going back to my earliest years, I was born with something called primary immune deficiency which basically means my white blood cell production is smaller than the average person and my white blood cells aren’t that smart. Growing up, I got sick a bunch. When I was growing up, I became the face for this nonprofit called the Jeffrey Modell Foundation and I really did two main things. One was I tried to help them go get med students to become immunologists. Number two is helping them try to raise money.

I’ll never forget meeting these entrepreneurs who I felt were fascinating and who were donating not only their money but their time. I never felt smart enough to be a doctor, and I was like, “Those people can keep me alive,” but the idea of building a company and being able to give back was always really interesting to me. I’ve always been the type of person that veraciously wants to learn about everything and anything I can get my hands on. Starting a company and exploring different industries has been a part of me since I was a little kid. 

BRYAN WISH: When you were a kid, what were you curious about? 

JASON SHUMAN: I’ve been interested in the most random things for the longest period. I’d go down these rabbit holes. I was interested in the psychology of my friend groups. I was interested in sales. I got interested in pocket bikes and go-karts at one point. When I hit late middle school was when I got really interested in startups and technology in general. When I went home to move out of our old house, I was finding business plans that I was writing. I tried getting USPS to put advertising on the postal trucks back then. I remember when Facebook popped up, I was like, “Huh, I can start Facebook pages for celebrities and gain followings and sell them to them.” I was constantly finding ways to make money.

If I could just learn about something and when I found business – specifically, when I found real business, my first job over at Identity Force and working under a former VC there when I was in high school, that’s when I knew. I was like, “Wow, these problems people are trying to solve every single day and the intellectual analysis that happens is something that really gets our juices flowing. 

BRYAN WISH: You said your mom was a therapist. Do you think your emotional development, as a kid, was a bit further along than maybe the people around you? If so, do you think that enabled you to give more thought or intellectual curiosity to ideas because there was maybe an open and safe environment at the home front?

JASON SHUMAN: Definitely. I think my mom has been somebody who has had a huge impact on my life in a variety of ways. I’ve always been a sensitive person. I felt I had a lot of adversity growing up as a child that I had to overcome. When things are rough and you’re crying yourself to sleep at night because you’re missing school trips or people are making fun of you for having a disease, you kind of need to figure out what your outlet is going to be. For some people, it can be a hobby. Not even necessarily just an outlet but how I try to approach things was trying to communicate my feelings.

I think that’s served me pretty well throughout my life. I think in some ways I’ve been hardened and don’t necessarily express my feelings as much as I did maybe when I was a kid. Still, in many other ways, I think that having transparent conversations and being able to communicate effectively, which started out when I was a kid, is one of the reasons why I’ve been able to climb the ranks and get into the career and profession I’ve been able to. 

BRYAN WISH: I love it because I’ve always believed that learning to express and communicate effectively at a young age enables free form of ideas and exploration. You can kind of build things out. I think words are the vehicle to enable you to see things further out; whether that’s in writing or even in your mind. You’re able to unlock things because of the development inside of you. It’s probably enabled you to meet the right people and have the right conversations to get you to where you are. 

JASON SHUMAN: In today’s day in age where everybody is overly stimulated with their cell phones and YouTube and dating apps, it is mind blowing to me. People need to be sitting down more and journaling. If you’re not sitting down and reflecting and processing, you’re just letting life go by. It’s very difficult today unless you’re intentional to go about that reflecting and putting things into words like you’re saying. 

BRYAN WISH: I think self-reflection and self-discovery is a constant and evolving process. Whether that’s just a quick check in with yourself at the end of the day of where things are or end of the week. Something I do with our business and my personal life is I set goals around different areas. Every week, I write and reflect against those goals. I do think there’s daily check-ins with journals for more feeling to come out. I agree that the reflection keeps you aligned on where you want to go if you’re intentional and have a path. 

You started to develop these emotional maturity skills, the reflection skills. You came into college and were gung-ho on business. People looked up to you. You were riding the entrepreneurial wave. Shit hit the fan and you had this identity crisis. Take us to that moment in time when this identity crisis as happening. What were the questions going through your head? What were you thinking about then?

JASON SHUMAN: I definitely remember a moment in time. We had an office in Framingham, Massachusetts, that was on top of some strip mall in the middle of nowhere. I was sitting in an Adirondack chair that we had inside the office because that’s what you do when you have a boat shoe company. We were starting to clean out the office at that point, and I was there alone and late at night.

I was like, “Do I want to do this for the next 10 years?” I knew the answer was no. I said to myself, “If I don’t want to do this for the next 10 years, what is it I want to do?” It came down to three things I felt I’d potentially want to do. One was, “Do I want to start another company?” When you’re burnt out and you just got beat up for the last two years and your bank account has less than $400 in it, the idea of starting a company again feels like climbing Mt. Everest. I was like, “I don’t think I can do that.” 

The second was, “Do I want to go work for a company? Do I want to go work for a startup?” I was lucky enough back in 2014 to have a lot of friends out there that were founders of companies and were looking out for me. I probably would have had opportunities to go work for. Some of which had been great and super successful. I appreciate the mentorship of people back in Boston during that period of time in my life. As I started to think about it, I was like, “I don’t know if I want to go operate right now.”

Then this last thing popped up. I remember a few weeks before I was with this guy, Dave Spandorfer, from Janji. I was talking to him on the phone. I was in Miami. I was like, “I was thinking about what I want to do next.” He’s like, “Have you ever considered venture capital?” I was like, “Well, not really. Can you introduce me to somebody to talk about it?” He connected me to Julian Moncada, who was at Lerer Hippeau Ventures at the time. That one call definitely changed my thought process’s trajectory on what it was I wanted to do in the next chapter of my life. 

BRYAN WISH: You asked yourself the questions. Do I want to start another business? No. Do I want to go work for another? You kept asking yourself the questions. When someone said venture capital, it kind of intuitively, “Maybe that’s interesting. I want to explore that more. Can you make an introduction?” Really being careful about your next steps and maybe why. So neat you actually took the time because I think so many people just rush into the next thing. Once you had that conversation and you asked for an introduction, what happened next?

JASON SHUMAN: The conversation with Julian, I remember I talked to him and a few other folks in venture. With Julian, it was like, “If you want to get a job in venture, there’s typically a few ways to get in. If you can sell a company, you can get in. Two, you can go to a really good school and go into an analyst program afterwards, which a lot of people do these days. Three, maybe you work at a portfolio company or a company in general that takes off and then you get into venture.” Then I was like, “Well, none of those really match my playbook. The fourth one, “Well, go make yourself invaluable before you get a job.” 

For everybody listening, one of the biggest exercises going back to thinking about your next step, you have to identify what it is you want to optimize for. You can’t optimize for everything. You can really only optimize for two or three different things. Whether it’s where the job is, how much it pays, how much autonomy you get, what your title is, what you’re working on day today, you’ve got to really process these things, and that’s the stuff you have to reflect. I was like where I did that reflection on venture capital, and once I realized that that’s what I wanted, I went after it full force. 

BRYAN WISH: Beyond optimizing for working in VC, at that time of your life, was the amount of money you were making or going to make in the next couple of years at the forefront of your mind? It sounds like you always had a more long-term focus. How much was money a factor in going after this?

JASON SHUMAN: A common misconception of early stage venture is that people make a ton of money. Money was a factor in the sense that I knew I needed to be able to pay my bills, and I knew I didn’t have money. The first job offer I got in New York was at Corigin Ventures. I was on a 90 day trial making $17.50 an hour. I love David Goldberg and Ryan Freedman, and they may laugh at me for bringing this up, but it was like I originally got the offer for the trial period and I thought I was going to get paid for 20 hours a week.

I remember telling David, “You can pay me for however many hours you want. I’m working 80 hours.” All I cared about was being able to pay my bills and to get that job at Corigin. The experience was what I wanted. The idea of building a firm with those guys was super exciting to me and the autonomy was incredible. Even when I decided to come over to Primary, I had some other options that compensation was better, but I think you need to dig down inside and figure out… By the way, some people may want to optimize for money, and that might be what makes them happy. I don’t think that’s wrong. It’s just not the thing that’s for me personally. 

BRYAN WISH: You’re intrinsically motivated by opportunity and experience. I’ve always believed that money will take care of itself. Like you said, people have different value sets and things they want to optimize for. I think for the true, intentional creators, are people who have bigger aspirations. Short term sacrifices are very necessary around finances. Let’s dive into that 90 day window. I’m going to go work 80 hours a week. What was it like? What were you learning? What were you absorbing?

JASON SHUMAN: Hustle is about working smart, not just hard. Before I got my job at Corigin and the way I went about getting my job at Corigin and then the first 90 days was all about working smart and hard. Whether it was before I got the job, which required me driving for Uber at night and during the day, I was sourcing deals. That was me finding deals in Boston, sending them to VCs in New York that didn’t have good coverage in Boston. That’s how I tried to make myself invaluable. Once I moved to New York and was with Corigin, it was all about figuring out what could I be really good at? What do I feel I was my superpower or what I found easy that other people found difficult and double down on that. Also, see where maybe the holes were inside the firm because venture firms are like basketball teams at the end of the day.

Everybody plays a different position. You might already have a 3-point shooter, and now you need a point guard. I decided I really wanted to play this role which was 1) I wanted to help build out the firm’s infrastructure. That included building out our investment memo process. I really leveraged a lot of relationships I made over those previous months hustling to get into VC to figure out the best process to craft within a new firm. 2) We were a new firm. I wanted to build the brand for the firm. I wanted to build the brand for myself. I wanted to make noise and meet everybody. I was literally taking a breakfast meeting every day, a lunch meeting every day, a dinner, and maybe a drink.

I was go, go, go, go, and everybody was going to know who I was, and I was going to make connections and try to add value to every person that I met. I think one thing I’ve been blessed with is a good memory and the ability to connect dots pretty well. If you leave an interaction with somebody and treat them well and help them out and genuinely want to help them out, then I think good things will come. I was lucky enough to end at Corigin for that period of time afterwards. 

BRYAN WISH: I think you’re right. The more you can make yourself invaluable to others, the more memorable and valuable you can become to people’s lives. It clearly needs to be done with intentionality and a smart way of building a relationship for the long-term. I think a lot of people think about the take or what they can get very quickly. I think that can ruin the natural relationship building process. 

Something else you said was when you got to Corigin Ventures, you said everyone has a spot on the team. You had to find your way to insert yourself, which takes a lot of observation to understand where you can kind of go in and create your own niche to make yourself invaluable. When you were surveying the land and figuring out where you could separate yourself and create your foothold within the business, what did it take for you to develop your own niche?

JASON SHUMAN: This one is like a catch 22. If you walk into a place and do the observation after you get there, you might end up in a place where you realize what needs to be done is not something you’re going to enjoy doing. It might not be something that you also are good at. Going back to an earlier part of the conversation around what you want to optimize for when you’re looking at jobs or places, I think that’s when you need to figure out what you want. When people come to me and say, “Hey, I’m looking for a job in venture.” The first thing I tend to ask them about is, “What type of a job in venture?” There are thesis-driven investors, investors that just source, investors that just do diligence, full-stack investors, and work super closely with companies, investors that spray and pray and invest in 50 or 60 companies a year.

Before I went to Corigin, I remember my interview with David Goldberg. I handed him a folder. The folder, amongst other things, it had a list of people that I would introduce his portfolio companies to that I felt would be a value-add. The message I wanted to send and the positioning I wanted to have was to be a power networker that will meet the biggest and best people that will add value to our firm. In terms of being potential investments or adding value to our portfolio companies, I genuinely enjoy. I’m in venture because I genuinely enjoy working with the companies and the founders themselves and the employees there in trying to help them live their most successful, fulfilling life. That pitch in that interview brought me into a place that wanted that. That’s how I ended up going down that path. 

BRYAN WISH: It’s one of the best skills you can develop before you have the credibility of the work behind you. It’s a big asset, and you can give value when you don’t have a service or a product or insight to provide, but you know how to put people together, and you can keep climbing that mountain of relationships because people trust you. If you do it in the right way, it can pay off. 

As you started to build a stronghold within Corigin, zoom out a bit and talk to us about how your career in venture has evolved and pivoted to get to where you are today.

JASON SHUMAN: I spent two years at Corigin. It was a really incredible ride. I’m forever grateful for the shot that Ryan and David gave me. I didn’t come from a family with a ton of money and connections in New York City that were LPs and funds. For them to give me that shot and to make investments while I was there was great. I came upon the end of the two years, and I had the opportunity to meet an entrepreneur named Mark Gerson who bootstrapped a company, Gerson Lehrman Group (GLG). Mark had asked me if I wanted to come over and launch his family office and really be his right hand. As part of that, I’d be doing venture investments and incubation. I’d be doing LP investments and nonprofit work.

We’d also be launching a mentor network between high networks and pro athletes. Going back to what I want to optimize piece, I was like, “This is an interesting opportunity, but I have some other opportunities I was talking to at the time.” What would I be optimizing for if I take this? At the end of the day, Mark, who is a real mensch and is insanely well networked, would teach me a couple of things. One was he was going to open up his network to me, which would help me really take things to the next level. Two, there’s not too many entrepreneurs in New York City that have grown a company to over $1 billion in value bootstrapped. To be able to see that day-to-day and then to be able to communicate with a person like that and get their buy-in, I think is a skillet from a communications standpoint that I wanted. 

I went over there and I launched that. I worked on that strictly for about six months until a portfolio company needed some support in restructuring after it spun out of another one. That was a decision of mine when Mark asked me if I’d help join his portfolio company with him as the chief of staff. I had some scar tissue going into that role because I was like, “Man, I’d operated. I had failed. Am I going to be good enough to do any of this?” Once again, it was like I’m 25-26. When else am I going to have the opportunity to go help raise venture capital and have a 30 person team and get to operate in a really interesting industry that’s BB SaaS which I’ve never done. I said yes, and I did that.

Then when we got to the tail end of that company, I knew I wanted to get back into venture and wanted to be at a place that was on the rise but a place that was super malleable still; where you could put your stamp on it. A place that I could really lead deals and invest in only a few companies a year and be able to roll up my sleeves. What’s unbelievable about the team at Primary, is that not only did it check all of those boxes, but they have this incredible portfolio impact team. There are executives like Cassie Young and Rebecca Price and Bob Peruzzi, who we used to work with, who’d go in and are literally 100 times smarter than me when it comes to all of the things that they do and are helping the founders 100 times more than I’d ever be able to in those ways. I think that aligning the stars and being able to be aligned with my mission made it the obvious choice for me. 

BRYAN WISH: It takes me back to how you just thought about getting into venture. You applied yourself at Corigin. The same process of intentionality of you said the stars aligning, but you had a vision of what you wanted. When the opportunity to take on this next step in your life and career presented itself, you knew it was a fit naturally because the networking opportunity that opened up, the success behind the founder, just a network of people involved. So it’d naturally be the next step in your career and trajectory. Is that fair to say? 

JASON SHUMAN: I definitely think so. At the time, you really got to sit down and start to think about these things. When you’re looking for a job, the best advice I can give is to run a process. Don’t let the companies only control the process. You can run a process. You should run a process with clear eyes. That way, no matter what job offer you get, there are ones you’re going to want. 

BRYAN WISH: When you look at your life and think the end of it and what it’s all worth, what do you want to be known for?

JASON SHUMAN: My mission in life is about empowering other people to live a more successful, fulfilling life. The way I’m hoping to really do that is by helping people get the tools and relationships they need. It’s part of the reason I said, “Yeah, let’s do this chat.” If 45 minutes of my time lands one piece of advice that helps somebody in this world, that’s what energizes me and gets me out of bed in the morning. I think I’m just going to continue to make decisions every single day whether that’s through the portfolio companies that we’re investing in that hopefully the founders are doing something similar to that with their employees or the other things I do outside of work or maybe eventually, one day, in my next chapter of life, what I end up getting into. I’m sure everything will have that north star in mind. 

BRYAN WISH: How can someone find you?

JASON SHUMAN: Give me a follow on Twitter. It’s @jasonrshuman and feel free to send me a DM. My LinkedIn mail tends to get a little bit too crowded.

One Away Podcast
Bryan Wish

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