“From Avocation To Vocation: How I Turned My Hobby Into A Career” With Catharine Dockery of Vice Ventures

Don’t let rejection get you depressed — starting your own business brings a massive amount of rejection. In my case, much of it came from investors who turned me down. I had some really challenging meetings, and frequently met people who didn’t want to invest. My reactions have really improved over time. Rejection is hard, but it […]

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Don’t let rejection get you depressed — starting your own business brings a massive amount of rejection. In my case, much of it came from investors who turned me down. I had some really challenging meetings, and frequently met people who didn’t want to invest. My reactions have really improved over time. Rejection is hard, but it can’t be a defining moment.

As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing…Catharine Dockery is the founder of Vice Ventures, a venture fund investing in early-stage vice companies. Catharine has long had a passion for vice investing, personally being involved in the seed round of Bev, a DTC canned rose company. While interviewing with traditional consumer venture firms, she continually brushed against vice clauses in investment pitches, with this friction culminating in the idea for Vice Ventures. Prior to launching the fund, Catharine was an early member of the digitally native vertical brands M&A team at Walmart, working as an analyst in the e-commerce division. Catharine was the president of her class at NYU’s Gallatin School of Individualized Study, where she studied a self-directed major on the intersection of neuroscience and finance.

Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

My parents divorced when I was relatively young, so I was raised mostly by my father. He is an ex-hippie who worked as a bartender at the Corner Bistro in the West Village neighborhood of Manhattan. My mother is a flight attendant for United Airlines, so she was usually traveling. I grew up playing lots of soccer and games with my dad.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

I found myself in a job that had some very exciting responsibilities, but without much opportunity for creativity, and decided to start interviewing to work as a consumer products venture investor. I was interviewing at a few venture funds, and without fail, one of the only repeated questions was to pitch an investment. At the time I’d just personally invested in Bev, a canned rose company with incredible branding, a fantastic CEO, and an aggressive distribution plan. It was a no brainer to pitch my most enthusiastic personal investment here. And in every interview, I found that none of the funds had the ability (or desire) to invest in a company producing alcohol, which in every case was the result of a vice clause. As I came home from one of these interviews, I clearly remember lying down on our blue velvet couch and asking my husband “How does nobody invest in these companies?” followed almost immediately by “Doesn’t that create a massive opportunity?” The research to investigate that thesis began the next day, and the next time I saw an incredible opportunity held back by vice clauses, Recess (naturally flavored sparkling water with hemp extract and adaptogens), I eagerly set out to help them raise capital, with the Vice Ventures SPV being one of their earliest investments.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

I’m no stranger to the allure of good ideas that never quite reach success. This one felt different. I feel like my husband and I bounce ideas off each other all the time and we’ve both become experts at critiquing the idea that doesn’t quite make it. That confidence was real, and then it solidified after the first few investor meetings where the two reactions were 1. you don’t look like the typical person raising a venture fund and 2. you’re really onto something here, I can’t believe it wasn’t being done yet.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

This is a hard question for me. In my opinion, if you’re not entirely sure you’d love to do it all the time, it’s not something you should do for a living. Doing something for a living is a fast way to turn a hobby you like doing 75% of the time into something you hate doing 100% of the time.

Along those lines, it’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

For me, running my own fund ticks off a lot of boxes for my “ideal job” — for me that is incredibly important. If venture didn’t meld well enough with my job ideals, I’d probably be doing something else.

I feel that I get an unusual amount of variety in my day to day already. Every day, I’m meeting with investors, founders, lobbyists, and industry experts. I’ve received an incredible mix of company pitches — the majority of which have at least some merit in my eyes. Every day is packed with things I enjoy deeply.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

I enjoy most the feeling of direct responsibility. When you run your own business, the stakes of an everyday decision are massive. I’ve had significant responsibility in prior jobs, but the responsibility of running my own business and managing the money that people have entrusted with me dwarfs that experience.

That being said, the deepness of the responsibility can be a real drawback. Throughout the first few months of Vice Ventures, I found it hard to turn off. When you own a business, work never ends. Small emails, of little importance, started to take attention from other things. The solution I found really came from doing most of my work outside of the home. Working from home all the time, while frugal, made it significantly harder to be productive.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

The largest difference between dream and reality for me came in the fundraising stage. The initial investor feedback had been so positive that I was overcome by the feeling of momentum. Most funds take months or years to be raised and do so quietly in the hope that their first close will be the first public view of the fund. When launching Vice Ventures, I didn’t take that approach, and it meant that despite the initial excitement, fundraising was a process requiring real work and attention.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

I’ve never really been on the point of quitting. When you decide to launch a fund, you give up the ability to turn it all off and go home. I’ve felt challenged at times, absolutely, but I’m fiercely committed to battling through it and delivering returns to our investors.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I remember when I first saw the draft for the Limited Partnership Agreement (LPA). My husband and I were traveling in Denver before I had meetings with founders, and he wanted to walk through the city. I’m not sure why, but I’d honestly hoped that the LPA would look something like a SAFE (typical security agreement for venture investment), maybe 10 pages max. I opened the file and my jaw hit the floor. We barely left the hotel room that afternoon and he still doesn’t let me forget how I ruined our first trip to Denver together. The lesson: never assume anything involving attorneys will be simple or short.

Who has inspired or continues to inspire you to be a great leader? Why?

Working for a visionary leader like Andy Dunn, you can’t help but be inspired to try and lead in a similar way. As a leader, I’m deeply focused on continually producing excellence. Andy’s also a master of balancing vision with execution — something that as an investor I’ve found to be an incredibly rare quality, and I hope I bring to my business.

How have you used your success to make the world a better place?

One of the best ways I think Vice Ventures can help the world is to support responsible operators in vice fields. While vices are often maligned as verticals where companies prey on customers’ weakness, good founders and management teams are capable of building these companies responsibly. By funding companies which do things the right way, we play an active role in supporting responsible actors.

Additionally, we are big fans of social justice initiatives around vice issues. One of the organizations we think is most effective is the Drug Policy Alliance (DPA) which is deeply involved in national drug policy. I came into contact with them first when at a conference about cannabis where they presented as policy experts, and have continued to be impressed ever since.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Don’t expect to take a vacation — everyone thinks that they’ll be the one magical founder who can do it all AND still go on vacation to stay fresh. I’m taking what feels like my first real vacation this coming week for Labor Day, and even then if things come up (spoiler: they always do) I’ll drop anything and everything to fix it.
  2. Don’t let rejection get you depressed — starting your own business brings a massive amount of rejection. In my case, much of it came from investors who turned me down. I had some really challenging meetings, and frequently met people who didn’t want to invest. My reactions have really improved over time. Rejection is hard, but it can’t be a defining moment.
  3. Rejecting investments is almost as hard as being rejected by investors — Saying no to companies is one of the hardest parts of my job. It’s a real downer to be the bearer of bad news, and especially bad when you have to do so to a company you think has potential but doesn’t quite pass your decision making process for investing.
  4. Don’t let your dedication make you ineffective — feeling like you need to spend 100% of your time on your business can be helpful, but only if you manage it well. I had burnout after the first few months and had to learn to be a better boss for myself.
  5. Take care of yourself — sort of like the previous point, I’ve found that it’s incredibly important for the fund that I am in the best frame of mind possible for investment decision making. Trying to work through illness, while it often feels worth it for me, really doesn’t create positive outcomes in my experience.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I’d hope to inspire people to not be shy about changing fields early in their careers. I was the sort of person who in college had the concrete certainty in their future career. I was going to be an investment banker, focused on international M&A. That was my life. I tried a few jobs at banks — investment banking intern, equity sales trader, and high yield credit analyst — but I didn’t find any of them satisfying. It was a really shocking transition to move away from a bank career but is a decision that I’ll always be glad I made.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“There is only one thing that makes a dream impossible to achieve: the fear of failure.” Paolo Coelho, The Alchemist. Reading is one of my favorite hobbies, and I just finished reading Paolo Coelho’s The Alchemist. The book, and this quote especially resonated with me as I worked to build Vice Ventures. The entire story is built around the journey to achieve one’s dreams, and the challenges of the path to get there. It helped me hold confidence even when dealing with the challenges of rejection and disbelief.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

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Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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