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“Why you should stay humble.” With Jason Hartman & Catharine Dockery

For me, one of the most empowering aspects of the quarantine is that I’ve dedicated a massive amount of effort to make my home be a space I can work and live effectively in for 99.9% of the time; both in terms of cleanliness/organization and building comfortable spaces, the experience of working from home has […]

For me, one of the most empowering aspects of the quarantine is that I’ve dedicated a massive amount of effort to make my home be a space I can work and live effectively in for 99.9% of the time; both in terms of cleanliness/organization and building comfortable spaces, the experience of working from home has been very positive. I’ve also tried to use a quarantine to better-focus my workday — if I don’t spend 20–30 minutes traveling meeting to meeting I now have a massive amount of free time to be redeployed.


As a part of my series about “Investing During The Pandemic”, I had the pleasure of interviewing Catharine Dockery.

Catharine is the Founding Partner of Vice Ventures, a venture fund investing in early-stage vice companies. 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.


Thank you for doing this with us! Before we dig in, our readers would like to learn a bit more about you. Can you tell us the “backstory” about what brought you to the finance industry?

Igrew up in a working-class household — my father was a bartender and my mother was a flight attendant. As someone who lived in NYC from an early age, I always saw the finance industry as the peak of self-made success. Those were my examples of people who often came from similar families to mine, and built names and livelihoods for themselves on the quality of their ideas and the work they put into their trades and opinions.

Working at a bank, however, was definitely not for me. I couldn’t handle the rigid hierarchy, the clumsy attempts to support women’s careers, or the lack of opportunities for creativity. Working at a bank still gave me a fantastic early training that I’m grateful for to this day and connected me with some incredibly talented individuals (i.e. my husband).

Can you share with our readers the most interesting or amusing story that occured to you in your career so far? Can you share the lesson or take away you took out of that story?

After over a year working at a bank, I remember going to coffee with one of my mentors. Usually we’d talk about the markets, internal events and politics/promotions at work, or her family. Instead, she just asked me one question: “Do you still want to be here?” It sounds harsh, but was an entirely valid question. I had become disillusioned with the work, and had never found the passion that I recently enjoyed. I quit a few weeks later and am forever grateful for that conversation and specifically that deeply probing question.

Are you working on any exciting new projects now? How do you think that will help people?

We’re working very closely with all of our portfolio companies to help them and their employees make it through this crisis intact. We’re trying our best to make sure these companies keep a healthy runway and protect their employees’ jobs.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

One person who I’m deeply appreciative of is one of my first investors, Marc Andreesen. I still remember the feelings from when he responded to my email, and when I stepped into the meeting. To have the support and belief of one of the leaders of my industry was a real validation of the fund thesis, and an important step in developing the fund’s recognition and deal pipeline.

Let’s shift a bit to what is happening today in the broader world. Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the coronavirus pandemic have understandably heightened a sense of uncertainty and loneliness. From your experience, what are a few ideas that we can use to effectively offer support to our families and loved ones who are feeling anxious? Can you explain?

There’s absolutely a real sense of isolation. For me, one of the most empowering aspects of the quarantine is that I’ve dedicated a massive amount of effort to make my home be a space I can work and live effectively in for 99.9% of the time; both in terms of cleanliness/organization and building comfortable spaces, the experience of working from home has been very positive. I’ve also tried to use a quarantine to better-focus my workday — if I don’t spend 20–30 minutes traveling meeting to meeting I now have a massive amount of free time to be redeployed.

Ok. Thanks for all that. Let’s now jump to the main core of our interview. As you know the stock market and the economy in general have become extremely volatile and uncertain. Many people “dollar cost average” and put aside a monthly sum into a long term savings plan for retirement, college, or a home purchase. If a loved one or a client came to you and said, “I have been saving and investing $500 every month in an S&P 500 index fund. Over the next few months until the dust settles, should I be doing something else with my money?”, what would you say to them?

I’d say you’d be shooting yourself in the foot. Changing a strategy like dollar cost averaging in a market downturn means you never necessarily had a strategy at all. Coming from a background in trading, I found it really inspiring that at all times, the desk had a sense for how it would manage positions and how it might trade the markets. A fund has to operate the same way — I’ve scaled back on some investing in the short term, focused on assisting portfolio companies wherever possible, and am on the lookout for distressed opportunities in the event of any continued downturn.

Eventually the economy will recover and rebound. Certain sectors, like travel and hospitality might be hurting for a while. But other sectors, like technology and healthcare, might do very well. If someone wanted to prepare today to take advantage of the future recovery, what would you suggest they do?

I think preparing for a future recovery almost as a type of market timing. Everyone else in the market is aware that the thread of COVID-19 will eventually subside. My main advice would be to avoid companies which are only viable in a time of crisis. Some signs I’d look for there would be a dependence on home delivery and/or use or products which are specifically designed for quarantine environments.

Are there sectors that provide exciting and lucrative investment opportunities today, specifically because of the volatility and uncertainty?

I’ve found cannabis to be an early field that shows promise in this environment, as it is an area that many people are bullish on, but which I think fell victim to a great deal of retail excitement (especially in public companies, but also private) and political disappointment around the pace of legalization. As valuations of the space fall back down to earth a bit and companies deal with the reality of the easy-money environment ending, we could absolutely see some compelling investment opportunities at much more reasonable valuations.

Are there alternative investments that you think more people should look more deeply at?

I think people should remember that at a time like this, their cash has the highest opportunity cost. You could invest in the listed equity market, private companies, or various other opportunities. I don’t know of many really compelling alternative investments that are applicable to non-accredited investors, and I feel like many of these are best explored in a more peaceful market.

The most oft-forgotten investment that I think most people should consider are cash equivalents (money market, bank deposits, t-bills, anything) — being on a trading desk will infinitely reinforce the point that doing nothing is a decision of its own, and a valid response to a challenging opportunity set. There is a real value to liquidity and having capital available for the NEXT opportunity, the one you didn’t know about when you made your previous investment decision.

If a person in their thirties and forties came to you today and said that they have $10,000 that they want to put away today for a long term investment what would you advise them to do with it?

Much of my response would revolve around other details — most of which really are trying to get at the answer to “What is the investment goal?” Defining your investment objectives is an exercise often forgotten by individual investors. Funds often set out to define their goals, so that investors can make an informed decision about how the investment might perform in a holistic portfolio. Do you want to spend your $10k buying the finance equivalent of lottery tickets, hoping to fly private jets to Monaco when you’re 60? Is this $10k supposed to be the basis of steady retirement income to supplement social security payments? Starting from an investment objective is the first step towards developing a cohesive strategy and putting it in action.

Ok, thank you! Here is a more general finance question. You are a “finance insider”. If you had to advise your adult child about 5 non intuitive essentials for smart investing what would you say? Can you please give a story or an example for each?

Have a plan (and don’t be emotional) — Everyone perfectly follows their investing plan when it’s working. Continuing a long-term investment plan like dollar-cost averaging is essential. Changing from an investment policy that is statistically successful can’t be a decision driven by emotions like fear. I get far more questions about investment strategy when the markets are falling — but there’s absolutely no evidence to suggest that individuals have any ability at market timing.

Don’t send good money after bad — Working at a bank I saw my share of trader “blow-ups” where traders saw their risk allocation drastically cut after chasing a trade that wasn’t working. Accepting a loss is hard to do, but there was always a pattern: stubborn traders got fired, flexible ones lived to fight another day.

Stay humble — The best investment professionals don’t make money 100% of the time. Taking venture capital as an example, the best funds invest in plenty of companies which never exit. Finance as a whole is driven by probability and I think it’s imperative to remember that even the best investors are still very frequently wrong. Judging an investment return profile from a deterministic outcome is guesswork at best.

Diversify — We have far more investment opportunities than ever before. Even non-accredited investors have a plethora of potential investments in an online brokerage account. Spend some time learning about new asset classes or market niches, and think about how they might fit into a diversified portfolio. Diversification is a great way to help better target your portfolio for your investment outcome — making it less likely you undershoot your intended outcome.

Keep learning — I spent my early career inequities and high yield debt, and barely knew the first thing about venture capital. I was able to find a part of finance that I feel is a unique fit for my personality, investment process, and creativity.

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

“People aim for the stars, and they end up like goldfish in a bowl. I wonder if it wouldn’t be simpler just to teach children right from the start that life is absurd.” Elegance of the Hedgehog by Muriel Barbery

I took a long and twisted path towards launching my own fund. I didn’t set out to do this from the beginning. Not every person has some shining “mission accomplished” goal that they’ve been chasing continuously from the beginning. We all think of ourselves as the main character, the center of the story. Life comes with a healthy dose of randomness, and embracing it can lead to some incredible outcomes

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

I’d like to support society being more open to discussions about mental health. Mental health issues touch millions of individuals yet are often covered up and pushed to the margins. We need to take better care of ourselves and take better care of each other, especially in trying times like the COVID quarantine.

Thank you for the interview. We wish you only continued success!

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