David Goldberg
Jan 23, 2017 · 7 min read
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As I’m writing this from seat 23a of flight UA331, thirty-five thousand feet in the air, there are so many thoughts racing through my head as I reflect on the last four days — an unforgettable experience known as VC Reboot.

I first heard of this bootcamp-like experience about 6 months ago after reading a blog post by Steve Schlafman and listening to the Reboot podcasts (a ‘must subscribe’). The stated mission:

Uncover your authentic leadership style and become the best board member/investor/supporter you can be.

Man, are they selling themselves short with that. It’s so much more.

To give some context, this is not my thing. It’s basically as far away as you can get from my comfort zone — right up there with sitting in a pit of snakes or swimming in shark-infested waters. Even further, I actually have a tendency to negatively judge these types of experiences, and the ‘weak’ ones that need to seek something more to make them better, more confident, or happy. After all, I was already confident and happy. Job of my dreams, great colleagues, amazing wife, newborn daughter, good health…basically problem-free.

So why did I go? For starters, I figured it would be good to push myself outside my comfort zone. This is rare, so just by going, I’d feel like I had accomplished something. Second, I planned to learn, something I enjoy — from the instructors/hosts (legendary VCs in their own right) and the dozens of other VCs in attendance, many more experienced than me. And lastly, getting intimate with my fellow VCs would be one of the highest forms of networking.

I was scared shitless. In fact, my wife had to talk me out of bailing just weeks before. I said it was because I didn’t want to leave Elliana, but I just feared the discomfort, and perhaps what I’d uncover.

Now I could go on for pages about everything that took place, literally and within, but out of respect for your time, and for the privacy of all the other attendees, I’ll keep it personal and (somewhat) brief.

The Summary:

The Formula:

Practical Skills

+ Radical Self Inquiry

+ Shared Experiences

= Enhanced Leadership + Greater Resilience

The Takeaways:

  1. The value of coaching is real, and it’s spectacular. I hugged Jerry when the weekend came to an end and told him he had superpowers. I hadn’t allowed myself to be open like that, let alone in front of strangers, in a really long time. Like ever. And the man can just sit on the floor, look sincerely in your eyes, simply ask “How are you” and boom, the ‘heart cracks and the light shines in.’
  2. I came solely for professional development. But my mind kept taking me back to my personal life. At first I felt guilt for this — after all, this wasn’t therapy, but coaching. But I soon realized it was all related, and all that underlying ‘stuff’ affected every fabric of my being.
  3. I had some mind-blowing revelations as the layers of the onion were peeled back, as I got a glimpse of my loyal solider and my shadow. In this moment right now, outside of the safety of the trust circle known as Chez Feld, it’s really hard for me to write and share. The guy next to me in 23b keeps giving me weird looks so I think he sees the struggle in my body. But here goes:

(1) Controlling my emotions is not the same as suppressing my emotions. I’m really good at the suppression — I’ve always thought this was a skill to be wielded, the power of which was reinforced by many of those around me, most notably by my mother. And it has served me well — kept me safe, made me a great poker player and trial attorney, and at times, a better VC, not allowing emotion to cloud my judgment. But by suppressing emotion, I lose the power of emotion — to connect at a deeper level with the ones I love. Specifically to VC, it blocks me from seeing the intangibles in founders — how they’ll get along with others, what drives them, what holds them back, how to get the most out of them. The key for me is to control, not suppress. To pull levers depending on circumstances.

(2) I have often failed to properly challenge myself, complicit in creating circumstances that hold me back. Whether it was the friends/girlfriends I surrounded myself with, the classes I took in high school, the college I went to, the major I chose, the careers and jobs I was attracted to, I was creating a safety net. Subconsciously, it allowed me to be the smarter one, to avoid feeling inferior. At bootcamp, I even found myself using the word ‘sabotage’. This too, has served me well. It also kept me safe, and built my confidence (Think Malcolm Gladwell’s Outliers). But it has now shifted to a handicap, keeping me from realizing my full potential. It’s ironic, as I always tell my founders to surround themselves with people smarter and better than they are. Time for me to drink the kool-aid.

(3) Manipulation is a double-edged sword. Like controlling my emotions, I was always aware, and proud of, my ability to influence others. Not in a negative way or to deceive, but to ‘shed light’ and push forth the agenda I saw as just. It certainly helped me excel as a prosecutor — to connect and influence victims, defendants, jurors, and judges. And as a salesman, and now as a VC — to win the deal or to make that hire. But what hit me this weekend with the force of a tidal wave was that I manipulate myself — and this drives me to make many decisions for the wrong reasons.

(4) I am not always present, and try to be a ‘fixer’ rather that a listener. While this partly comes from an innate desire to help, it also comes from my discomfort and awkwardness to other’s people pain. So by quickly offering ‘a solution’, I am subconsciously trying to end my discomfort as quickly as possible, rather than the other persons. Oftentimes, a solution is not what is sought after, but rather a sounding board for that person to work through their own struggles. I need to listen more, empathize more, care more. This is directly applicable to my relationships with founders and role as a board member.

I originally outlined in this post a section on ‘The Application,’ in how I was going to take everything I learned and make immediate changes for the better. But I don’t think I’m ready — it’s still too raw, too convoluted. As Jerry put it so eloquently, ‘we stirred the bottom of the pot,’ and it hasn’t yet settled, and I need some more time. At least to get off the plane, get a good night’s sleep, hug my wife and daughter, and just be. For now, awareness and acknowledgement will have to do, and hopefully there will be a natural effect before I really get down to setting a plan. But I feel good, ironically stronger through recognizing and embracing weakness. And beyond good, I feel hopeful, and excited for what the future holds.

The acknowledgments:

· To Ryan, for encouraging me to take advantage of this experience.

· To Steve Schlafman — who probably has no idea but his writing and words inspired me to take the leap

· To my wife, Ania, for always encouraging me to push myself and step outside my comfort zone. And specifically here, for convincing me not to back out when I was manufacturing excuses. And for holding down the fort while I was away.

· To Jerry and the entire Reboot team. You’re fucking sorcerers. Beyond being truly amazing at what you do, your genuineness and authenticity make all the difference. I am forever grateful.

· To Brad (and Amy), for opening up your home and your hearts. (And your bathrooms.)

· And to the rest of my cohort — you are all really special people, and I owe much of my experience to you. We will forever have a special bond. There are two specific individuals that I won’t name out of respect for their privacy, but you know who you are…our walks were monumental, and I love you both for it. I hope I was half as helpful to you as you were to me.

“I thank you for your service. I continue to grow.”

If anyone would like to chat further about my experience, or any of their own struggles, I’m happy to make myself available, and can be reached at

Alpaca VC

Alpaca VC leads seed companies reshaping the real world.

David Goldberg

Written by

Start-up junkie. General Partner @AlpacaVC, Founder @freshneck. The U. #KauffmanFellow Class 22

Alpaca VC

Alpaca VC

Alpaca is a New York based venture capital firm leading seed-stage investments in the founders defining the future of daily living.

David Goldberg

Written by

Start-up junkie. General Partner @AlpacaVC, Founder @freshneck. The U. #KauffmanFellow Class 22

Alpaca VC

Alpaca VC

Alpaca is a New York based venture capital firm leading seed-stage investments in the founders defining the future of daily living.

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