Month: October 2019

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The Myth of the 30-Second Elevator Pitch

I’m not the biggest fan of the 30-second elevator pitch. Although I do believe it has its merits in the art of being concise – to be able to take a complex subject, be it a person or a project, and succinctly describe it for your respective audience, I trust the art of storytelling more.

The elevator pitch is designed to be the appetizer before the entrée, but what I find more valuable is the entrée itself, which, unless you’re at a 20-course Michelin-starred meal, aren’t short. I have rarely seen a deal close on an elevator pitch, much like I haven’t seen or heard of two people become best friends on a “Tell me about yourself.” Elevator pitches, like teaser trailers, are designed to have certain words or phrases click with the one(s) you’re pitching to, and, at some point, becomes too “templated” to connect on an emotional, more-human level. Earlier this month, I recall Robert McKee, one of the most respected screenwriting lecturers out there and a FullBright Scholar, writing about the dichotomy between film and TV in his newsletter, which is analogous to the differential between pitches and an in-depth coffee chat:

“Long-form writers have the power to reveal character complexity and depths of humanity no medium has ever delivered in history.”

Similarly, in my experience, through having a conversation about one’s inflection points in life, I can better understand someone’s depth of character and scars. For example, I love to ask founders: “How did this idea come to be?” Like I alluded to in my piece about my thesis, founders who are obsessed about the idea have a personal vendetta against the problem. They use “I’s” and “we’s”, whereas others who haven’t seen the blood, sweat and tears firsthand would often reference the numbers and speak in large, more abstract scopes. Outside of founders, especially those in fundraising mode, who have practiced knowingly or unwittingly the same responses over and over from meeting with investors, people, who have been in the trenches, often have a less well-rehearsed response to such questions – more scrappy, but much more detailed.

Just the other day, I read a brilliant response to a Quora question on “As a VC, how do you know an entrepreneur has ‘grit’?” that summarizes a quick calculus that differentiates the entrepreneurs from the “wantrapreneurs.” The answer in two words: specificity and compassion – two things which, unfortunately, most elevator pitches don’t cover.

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My Favorite Quirky Vacation Response

As with most people, when I first learned the how-to’s of communication – be it a resume, cover letter, cold email, college application, or coffee chat, I was taught the tried-and-true rubrics that my predecessors used with reasonable success. I’ve never liked these cut-and-dry templates, but by societal norms, I deemed them necessary. But they not only lack personality, but often times, relevance to whom they’re addressing, on a human level. Of course since then, I changed my whole suite of online, as well as in-person, communication, but I know there are still many means I may have overlooked or taken for granted. In the past two years, I’ve made it my mission to notice and change what isn’t me, and along that path, I stumbled across my old email vacation response.

This post was actually inspired, over dinner, by my friend as she’s gearing up for the holiday season. On the flip side, Brad Feld, a brilliant VC, through his blog post on Feld Thoughts and Nick Kokonas, one of the creative geniuses behind the Alinea Group, in an episode of the Tim Ferriss Show, inspired my current email vacation response that I started using about a year back:

I’m currently out building my first wand, but I can’t seem to find the elusive phoenix for its feathers.

I know I’m supposed to say I won’t be able to respond until I get back on
[date], but the truth is I’ll be lying out of my ass, pardon my French. In always having my phone with me, I will more likely than not see a notification blip pop up on my phone lock screen. And I know that from time to time, I will need to interrupt my vacation to answer something urgent.

That said, I promised myself I’d unplug and enjoy my vacation as best as I can. So, I’m going to run an experiment. I’m going to let you decide:

– If your matter is really urgent, resend the email with your subject line preceded by [URGENT] and I’ll try to respond nimbly.
– Otherwise, I’ll respond when I return to the beautiful SF.

Cheerios and orange juice,

David

As a final commentary, I highly recommend following both Brad and Nick’s work, regardless if you’re in the VC or culinary fields, or not. I’ve been a big fan of both for years, and their insights, outside of email structures, have definitely helped me become the person I am today. As a cherry on top, I find Nick’s Twitter and Medium profile descriptions hilarious.

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Why I jumped into VC

I’ve always had a life goal of meeting, learning, and helping the craziest, most creative, and most inspiring people in the world (and maybe one day, outside of it). So, half a decade ago, I made that dream-like goal my mission. Every week I reached out to one new person I was insanely excited about, which sounded great in theory, but scared the hell out of my introverted self. I would find the person of the week (POTW, as I would abbreviate it in my journal) from anything that would spark my interest: articles, podcasts, books, friends (and our online and offline conversations), memes, or YouTube videos. I then forced myself to find every way possible, and over time, figure out the best way possible, to meet these brilliant folks. It was a trial-and-error game of email, call, warm intro, Instagram or LinkedIn DMs, hand-written letters, and even attempting to show up at their office and ask for a meeting unannounced. Most were in vain, but those that I did succeed in, always had me jumping with joy, which was quickly followed by nervous adrenaline, as if I had overloaded on caffeine.

But that’s what made every single week fun. Every week I had something to look forward to – a mission that I would jump out of the bed every morning to accomplish.

That’s exactly why I didn’t give myself time to blink when I got the chance to jump into venture capital. Venture capitalists have a great track record of finding and investing in brilliant and passionate dreamers. And when I had yet to find my own systematic calculus for finding fascinating humans of the world, the mysterious land of venture capital would help me gain insight and a means to create my own. At the same time, I just couldn’t ignore my former professor’s description of the VC industry:

“A career where you get to see the future from one person’s perspective. And if you piece enough of them together, you’ll be able to help build the future you want you and your children to live in.”

Though I’m still only a meager three years in, and many miles short of having children, I’ve learned VC is a much more complex beast than I initially thought, but it doesn’t change my mission: to meet, learn, and help the craziest, most creative, and most inspiring people in this world. As someone who’s on the more junior side of life, there has been no better industry for me to learn, in breadth and in depth:

  1. How to start and grow a business,
  2. The frontiers of technology,
  3. And the fundamentals of human relationships.
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