Tag: harry stebbings

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DGQ 6: What three adjectives would you use to describe your sibling?

ocean, sibling

“Use three adjectives to describe your sibling. And describe yourself in comparison.”

I heard this question weeks ago from Doug Leone, Sequoia Capital‘s Global Managing Partner, on Harry Stebbings’ 20VC podcast. Known for having some of the best questions in venture and having led incredible investments into Meraki, Nubank, ServiceNow, and more, Doug loves to ask this question to founders he’s meeting for the first time. My initial response was “this doesn’t make any sense.” But in the podcast, he reveals why he loves the afore-mentioned question.

Before writing a check, an early-stage investor’s job is to answer three questions. Why now? Why this? And why you? The ‘why you’ question is admittedly one of the hardest questions to answer. Even for myself, I struggle from time to time to understand why I should scout a one founder over another over the same idea.

In a short 30 minute conversation, there’s only so much an investor can understand about a founder. There’s fundamentally a level of information asymmetry. Founders want to convince investors to take a bet on them. Yet, investors need more information to be comfortable making an asymmetric bet on them. We see echoes of a similar dilemma when recruiters interview applicants for jobs. Or when a property manager interviews a potential tenant.

Generally, recruiters, like most others, regress to questions like: “What are three of your strengths? Three weaknesses?” Having been asked so bluntly, interviewees, on the other hand, often have their guards up. They pick three strengths that would make them look the best. Equally so, they pick three weaknesses that show just enough honesty and vulnerability where they don’t get disqualified from the candidate pool. All of which exemplify pre-scripted answers.

Conversely, Doug found a way to do so without arming the interviewee’s, in this case, the founder’s, defenses. What three adjectives would you use to describe your sibling?

As Doug shares, “In a law of diversity, two siblings are less likely to be alike than two strangers. And so, how they usually describe their siblings is usually opposite of how they describe themselves. It’s a self-awareness question.”

You might realize the same principle holds when you describe a friend or a colleague or your spouse. The way you describe them often contrasts with your own disposition. “My friend is really curious.” Implicitly, you’re saying you’re not as curious.

So, the next time you talk about someone else, it’d be an interesting thought experiment to see how those same words relate or contrast with you.

Photo by Limor Zellermayer on Unsplash

The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.

Subscribe to more of my shenaniganery. Warning: Not all of it will be worth the subscription. But hey, it’s free. But even if you don’t, you can always come back at your own pace.

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#unfiltered #23 Twenty-Four Frames per Second – Jerry Colonna, The Illusion of Motion, Mental Health, and Radical Self-Inquiry

24 fps, film, questions about mental health

What appears fluid is twenty-four frames per second. Twenty-four precious moments per second, lived second after second after second. And each of those still moments is imbued with feelings and memories. The rapid fluidity of each of those moments defines the patterns and beliefs that, in turn, define our lives.

Our lives are twenty-four frames per second, with each frame a set piece of feeling, belief, obsession about the past, and anxiety about the future. Neither good nor bad, these frames form us. They become the stories we tell ourselves again and again to make sense of who we’re becoming, who we’ve been, and who we want to be.

Ghosts of our pasts – our grandparents and their grandparents as well as the ghosts of their lives – inhabit the frames. They and their beliefs, interpretations of scenes, words, and feelings haunt the frames of lives as surely as the roses, figs, and lemon drops of our present daily lives do.

Slowing down the movie of our lives, seeing the frames and how they are constructed, reveals a different way to live, a way to break old patterns, to see experiences anew through radical self-inquiry.

– Jerry Colonna in Reboot: Leadership and the Art of Growing Up Chapter 1: Passing GO

Who is Jerry Colonna?

I recently had the fortune of having an email exchange with one of the greatest household names in the space of startups and venture capital, especially known for his empathy and candor. A name synonymous with mental health, accelerators and being radically honesty about his journey – professional and personal. In our chat on mental health, he highly recommended Jerry Colonna‘s book, where the above passage comes from. So I just had to get it.

I first heard of Jerry on Harry Stebbing’s Twenty-Minute VC (his most recent episode with the CEO Whisperer) and The Tim Ferriss Show. And over the years, possibly as a result of confirmation bias, I’ve heard his name pop up over and over again from various founders and VCs. Over the decades, many people know Jerry as:

  • A venture capitalist,
  • An executive coach,
  • Co-founder of New York’s Flatiron Partners,
  • Partner at JP Morgan,
  • Founder of Reboot,
  • And, probably best known now for being the CEO whisperer.

So far, his book has reflected all the above and more.

A short trip down memory lane

Although we’re used to 60 frames per second (fps) for daily use or 120 fps for movies these days, the illusion of motion was first found at the optimal 16 fps. Early silent films, like Charlie Chaplin films, were then sped up to 24 fps, as far back as 1927. Admittedly, part of the reason as to why they seemed so comical. As technology caught up, still, the de facto frame rate was 24 fps.

In 2012, The Hobbit series was shot in 48 fps. In 2016, Bill Lynn’s Long Halftime Walk was shot and projected in 120 fps. Gemini Man, which came to theaters 3 years later, followed suit. James Cameron also plans to shoot Avatar 2 at 60fps, with the goal of maximizing the feel of a 3D-world. But as both filmmakers and animators approach higher and higher frame rates, there have been and will continue to be the effect of the uncanny valley. Uncanny valley, or in other words, the more something artificial looks to be real, the more our minds try to reject its appearance. Subsequently, making certain objects, robots, or animations seem creepy and chilling. Part of the reason, it’s a ‘hell no’ to horror films for me.

After decades of 24 fps films, it’ll take a while before our minds catch up to what we see. But I digress.

Moving Forward

Just like how silent films shot at 12-16 fps were shown at 24 fps, giving its comical effect, many of us, myself included (until 3 years back), live by weaving narratives between cross sections of time – both in our personal lives and in our careers. And we script our biographies in a format where seemingly everything happened for a reason. Maybe some things did.

But on the other hand, maybe you’re like me. Where I don’t know what the hell is going to happen tomorrow. Yes, I tell myself I have these plans and goals in life I’m working on accomplishing. But if you ask me, what pitfalls are up ahead? I haven’t even thought about half of them. Another quarter, and I’m being generous to myself here, I think I have a good grasp on, but knowing myself, I’ve got about 20% of it down, 80% I’m missing some piece of the puzzle.

After all, as Warren Buffett once said,

“The rear view mirror is always clearer than the windshield.”

The last quarter – I’m scared – really scared for. But, what’s life without a bit of risk and adventure?

Moving in the Present

While it’s easy to build that narrative for the trail behind us, it’s hard to forecast the narrative forward. So, I take life play by play – frame by frame. Slowing down to that 16 fps, examining, like Jerry suggests, my life in real time. Savoring and reflecting on every moment – the good and the bad. Reexamine my biases – the overt and the covert, in the words of a brilliant sociology professor I chatted with last week. ‘Cause they will make who I am tomorrow.

So, I’ll end on 2 big questions, inspired by that professor. 2 questions I plan to answer and reexamine every month:

  1. What do your social circles look like?
    • Professional? Personal?
    • How did you meet them? How often do you stay in touch with them?
    • What beliefs – overt and covert- are they reinforcing? Are these beliefs worth reinforcing?
  2. Now that you know, what are you willing to give up to make it happen?
    • Are you willing to take radical measures to do so?
    • What do you say that you don’t mean? Or find it hard to follow through on?

Photo by Kushagra Kevat on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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My Cold Email “Template”

coffee, cold email template

First of all, I should preface. Though I find templates to be useful when you’re shooting for quantity over quality, I default to only using limited elements of one, if at all, when my goal is quality > quantity. The goal with 90% of my emails I have ever sent is where I’m punching above my weight class, be it –

  • Applying to college – writing a letter to the deans of respective schools to get a personal tour,
  • Asking for funding – from top-tier VCs and potential long-term partners,
  • Asking for advice – from VCs and seasoned founders, in the form of tactical and veteran mentorship,
  • Or, exploring perspectives. I’m pretty liberal in my scope here.

If you’re here reading this and are looking for a silver bullet. If you’re looking to be that John Wick walking away from a massive explosion behind you… well, I regret to let you know – I don’t have one. I wish, but I don’t. But to me, that’s what makes this black box of relationship building ever the more fascinating. Had it been easy, I would have gotten bored real fast. Unfortunately, I have a limited mental stamina for things that work because… well, they work.

Inspired and encouraged by my conversations with 4 amazing souls over the past week – a founder, product manager, startup mentor, and my mom, here are the tactics I learned after years of reaching out to folks that inspire me, specifically closing one a week since 6 years ago.

Continue reading “My Cold Email “Template””
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Competitive Awareness as a Founder

sailing, competitor analysis, competitor awareness

For a while, I’ve been publicizing one of my favorite questions for founders.

“What unique insight (that makes money) do you have that either everyone else is overlooking or underestimating?”

I first mentioned it in my thesis. And, which might provide more context, was quickly followed by my related posts on:

For the most part, founders are pretty cognizant of this X-factor. B-schools train their MBAs to seek their “unfair advantange”. And a vast majority of pitch decks I’ve seen include that stereotypical competitor checklist/features chart. Where the pitching startup has collected all the checkmarks and their competitors have some lackluster permutation of the remaining features.

There’s nothing wrong with that slide in theory. Albeit for the most part, I gloss over that one, just due to its redundancy and the biases I usually find on it. But I’ve seen many a deck where, for the sake of filling up that checklist, founders fill the column with ‘unique’ features that don’t correlate to user experience or revenue. For example, features that only 5% of their users have ever used, with an incredibly low frequency of usage. Or on the more extreme end, their company mascot.

To track what features or product offerings are truly valuable to your business, I recommend using this matrix.

And, I go into more depth (no pun intended) here.

Competitive Awareness > Competitive Analysis

I’m going to shed some nuance to my question in the words of Chetan Puttagunta of Benchmark. He once said on an episode of Harry Stebbings’ The Twenty Minute VC:

“The optimal strategy is to assume that everybody that is competing with you has found some unique insight as to why the market is addressable in their unique approach. And to assume that your competitors are all really smart – that they all know what they’re doing… Why did they pick it this way? And really picking it apart and trying to understand that product strategy is really important.”

So, I have something I need to confess. Another ‘secret’ of mine. There’s a follow-up question. After my initial ‘unique insight’ one, if I suspect the founder(s) have fallen in their own bubble. Not saying that they definitively have if I ask it, but to help me clear my own doubts.

“What are your competitors doing right?”

Or differently phrased, if you were put yourself in their shoes, what is something you now understand, that you, as a founder of [insert their own startup], did not understand?

In asking the combination of these two questions, I usually am able to get a better sense of a founder’s self-awareness, domain expertise, and open-mindedness.

Photo by Ludomił Sawicki on Unsplash

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