Dear Brad, Fred & Mark: How The Hell Do You Do It?

A few weeks ago, I tweeted out the following:

Existential vc questions: Am I an investor, therapist, consultant or content marketer?

— Ezra Galston (@EzraMoGee) June 4, 2015

Let’s be clear: I am blessed. Being a venture capitalist is an extraordinary job. Within a single title & firm, I have the platform to be a thinker, be a writer, be a gambler, be a cheerleader, be a marketer, and be a friend. With some exceptions, I get to do what am I most passionate about.

And yet, VC is nevertheless, a really stressful job:

VC is easier than being a founder but still very stressful. Wish there was a forum for young VCs to share ideas and advice. There’s a void.

— Steve Schlafman (@schlaf) June 4, 2015

I’ve been vocal about my positive experience with the Kauffman Fellows, a 2-year fellowship that I recently (and sadly) graduated. And I’ve been equally vocal that the value in the program was not solely with the education materials, but really came out in our quarterly group therapy sessions, aka “Debriefs.” In an industry which can be rather opaque (even for us on the dark side) I realized how paramount it was to have an unconditional, non-judgemental group of VC friends who understood all my personal fears, struggles, and weaknesses in the industry.

And so, given my commitment to transparency, I will share one of those personal struggles. I look at heavyweights like Brad Feld, Fred Wilson, and Mark Suster & just have to ask: how the hell do you do it?

How are you everywhere at once? How do you produce so much content? How do you maintain thoughtfulness on the forefront of industries? How do you have time for all your entrepreneurs? How do you have the time to help them hire? How do you have time to handle their midnight freakouts? How do you have time for your freaking families?!?! How do you stay balanced? How do you find time yourself? Seriously, how do you do it?

And Brad – and this one’s for you – I have sent you I think two cold e-mails in my life (and we’re not friends although I’d love to be!!!) and your average response time is….wait for it….1 minute.

As a young VC, I look up at the edler statesmen of the industry and am simply in awe. It’s not about working hard. Because everyone works hard. And it’s not about being smarter, because everyone in this industry is hellasmart. So it must be something different? And I’m not sure I can pinpoint it.

Here’s where I’m coming from: For example, I love producing content – I absolutely love writing. But you know what? All the people who come up to me or send me notes complimenting those successes actually add to the anxiety: will my next piece also be published on TechCrunch or Forbes? Will the next piece also get 100k views? Will I wake up to e-mails from public company CEOs who stayed up late to offer feedback on my thoughts?  (But please keep the compliments coming!!! just for my mom to read, yknow?! ok, thx!)

I’ve read the practical tips, but frankly, I find those underwhelming. Not checking Facebook is not a solution to this problem, because while time management is certainly a part, it’s only one of the axioms. This is a question that is more conceptual, emotional, maybe even spiritual than it is practical.

Sometimes I wonder if it has to with playfulness (a concept I articulated in The Importance of Being Dumb). I think that’s part of it. And I also wonder if it’s about not being too hard on yourself (I’ve noticed that all three of you are open about your weaknesses and struggles) – and that’s a part of self-awareness anyways, which is undeniably a vital quality for VC.

I think a lot also has to do with triaging focus. It’s another concept Greg McKeown discusses in Essentialism (I promise I’m not getting paid to shill this book):

Essentialism is not about how to get more things done; it’s about how to get the right things done. It doesn’t mean just doing less for the sake of less either. It is about making the wisest possible investment of your time and energy in order to operate at our highest point of contribution by doing only what is essential.

The way of the Essentialist means living by design, not by default. Instead of making choices reactively, the Essentialist deliberately distinguishes the vital few from the trivial many, eliminates the nonessentials, and then removes obstacles so the essential things have clear, smooth passage. In other words, Essentialism is a disciplined, systematic approach for determining where our highest point of contribution lies, then making execution of those things almost effortless.

And yet, as much as I want to envelop myself in Greg’s beautiful prose and allow only the vital activities to permeate my existence, it still seems so practically impossible. How do I avoid all the meetings I have to take as “favors?” Or the meetings I take “defensively” – because if I don’t, and the company gets huge, then I get blamed. Can I stop attending certain events which waste untold hours if the effect will be to hurt the feelings of the organizer? Should I stop spending my evenings with my baby boy and instead be that VC who responds to nightime e-mails instantaneously? Should I stop cooking dinner for my pregnant wife? And on and on and on.

And, as I believe personal and professional lives are inextricably connected, feeling really freaking good about time utilization in the professional sphere (or personal) will undoubtedly make one more focused in the other realm.

Yesterday, my wife and I took our 2.5 year old son for a walk on the beach, gently testing the lapping waves of Lake Michigan with a timid toddler. It was a beautiful day and perfect weather. We both looked relaxed, dressed in our aqua blue polo and skirt, respectively. And yet, when she asked me “honey, are you really here right now?” I had to admit that I was struggling. My mind was in so many places – how to best strategize portco issues for the coming week, how to react to certain family issues, how to sell myself to a series of founders I love – I was also at the beach, but it was only one small piece of the puzzle.

That moment made me want to write this blog. So, to those who are making it: how are you everywhere at once and yet always focused in the present – for your families, your partners, and your entrepreneurs? Because I am struggling. And I want really badly to figure it out.

About the author

Ezra Galston
Ezra Galston

Consumer focused hustling @Chicago Ventures, Young Entrepreneur @Foundation Capital, Class 18 @Kauffman Fellow, and Chicago Booth MBA. Former professional poker player, with 4 years experience doing marketing/biz dev in the online gaming industry. Launched a "poker hedge fund" in 2011, a record label in College, and produced a festival screened short film in 2006.

  • A big part of it is simply practice. Years and years of it. If you read Startup Life – which I wrote with my wife Amy ( you’ll see the many things I’ve struggled with over the years.

    It’s not just about getting balance between work and life (which I think is impossible – I prefer “harmony”), it’s not just about becoming efficient, or letting go of stuff, or being successful, or learning how to spend time on what you want, or even figuring out a rhythm which works for a while, but then suddenly stops (

    It’s about practicing while exploring yourself – what works and what doesn’t. And recognizing that you are a laboratory for yourself over your lifetime, which is hopefully a long period.

    And, when you say “what about tactics”, just remember that Roger Federer still has amazing tactics, but he continues to practice them every day, even as he sits atop the mantel of the best tennis player ever (although Amy would argue that title belongs to Nadal).

    • egalston

      Thanks Brad – that seems to affirm the feedback I’ve been getting elsewhere today (for example – that the answer is in constant iteration and adaptation.

      Still, it seems hard to accept that given all the obligations AND opportunities (which is a very large, hard to quantify, mostly unknown bucket), that there’s just this continual weight of feeling like you’re not doing enough, that you have to be every thing to everyone, and always be perfect – even as you’re practicing and growing.

      I loved your post recently where you told a founder that you simply wouldn’t play the “slow-roll game” ( although I have to admit that as a young VC, the idea that I could miss a firm or career defining company because I have other priorities is terrifying. I don’t yet have the confidence to do that (I guess the good news it’ll take a few years to find out so it won’t sting as much??)

      Like you said, I guess it’s simply living with these fears, and practicing…working every day to confident with more choices and testing where time needs to be spent. Here’s to practice & review.

    • Dave Katz

      Brad, I read two of your books last week (Venture Deals & Startup Opportunities) and now I guess I have to add one more. Great question Ezra! I’d love to see a “day in the life” comparison of Brad, Fred, Mark, and you to see who sleeps more, reads more, and writes more.

  • Roy Bahat

    Ezra, I wish more people had the courage to pose the big questions, like you just did. I admire that. Well done. I think we’re at the precipice of seeing new relationships between people and their work, and you’re experiencing a frontier of that. Let us all know what you learn…

    • egalston

      Thanks @roybahat:disqus for the affirmation, it’s been really nice having you on my side these past few months. I do often wonder if simply the pursuit of mediocrity is a healthier lifestyle. Yet I don’t think I’d find that personally fulfilling. What Mark’s post today seemed to suggest is that he lives his life as if he’s in pursuit of mediocrity, but that iteration & practice has enabled him great success in spite of that. Not sure it’s so simple but will keep u in the loop!

  • Joey Arora

    Great article Ezra! I in a constant flux to create balance between my military life, startup and building entrepreneurial communities. Your self awareness to recognize this is great. Based off my military experience I try to recognize what I am most effective at in the current moment and go do that. Then as my focus shifts to then move my attention and energy to those things. As others here have said, it’s about constantly growing and shifting.

    • egalston

      I can’t even imagine the pressures of military life. My father was a marine and I know the travel/distance was extremely taxing on a young marriage.

      While I like the idea of adjusting the majority of energy & focus into the most effective space at any given moment, the reality of these jobs demands a lot of multi-tasking & accommodation of de-prioritized tasks. I simply don’t have an answer for that yet. Mark wrote today in his new post that he doesn’t lose sleep over being imperfect at e-mail. But as youngVC, if I’m crappy on e-mail my image gets wrecked. But the question to all of us is what can I reasonably de-prioritize yet still achieve nearly all the macro goals.

      It’s a work in progress.

      • Joey Arora

        Luckily, I’m not married right now 🙂 More time for startup life!

        I go back and forth with email, when I’m into it, Ill write a lot but focus on what objectives I need to accomplish. If I know its a super important email, ill compose a draft and come back to it later if I am not focused on it or am itching to accomplish something else.

        I am constantly creating spaces and times to get into “flow” (there is also a great book on it). I want to maximize times where I am energized by multitasking and knock out to-do’s left and right. I thrive in that environment so I seek to create it as much as possible. For me that requires balance as well. I need to be physically active, want to spend time being social talking to people, and then need stimuli (something interesting to work on) and deadlines (an internet connection helps…). On days that I do those things, I feel significantly more productive and knock out the random tasks while pursuing the macro goals.

        What do you do to find your flow?

  • Toby Lewis

    Arguable one of the reasons those three VC bloggers found success on the content marketing side, especially Brad Feld and Mark Suster (and I would also add Ben Horowitz), is how frank they are about psychological struggle, and how this affects the entrepreneurial struggle especially.

    Being brave enough to be so upfront about your feelings will probably help. Especially as everyone who has had a high pressure job/start-up/VC role, and a young family can empathise. I really rate coaching if things feel simply too hard. With a bit perspective what seems a struggle, can become great and enjoyable.

    • egalston

      That takeaway – that they’re all open about struggles & weakness – is a really nice insight into why they’ve been successful. Great thought. I can only hope to emulate that 🙂

  • Love the transparency and if there’s a group that’ll fill that “void” then I’m sure we’ll hear from you first!

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