A Reminder of “Why I Love You” – Managing Downtime and Dynamics Between Fundraising Meetings

love, founder vc love, vc fundraising meetings

I recently read Mark Suster‘s 2018 blog post about startups on “Remind me why I love you again?”. As an extremely active VC, he specifically detailed why, unfortunately, by meeting 2, 3, and so on with a founder, he may forget the context of reconnecting and why the founder/startup is so amazing. And, simply, he calls it “love decay”.

Mark Suster’s graph on ‘Love Decay’

The longer it has been since a VC/founder’s last meeting, the harder it is to recall the context of the current meeting. Though I may not be as over-saturated with deal flow as Mark is, it is an unfortunate circumstance I come across in meeting 5-10 founders and replying to 100+ emails a week.

Continue reading “A Reminder of “Why I Love You” – Managing Downtime and Dynamics Between Fundraising Meetings”

#unfiltered #21 The Recipe for Personal Growth – Thomas Keller’s Equation for Execution, The VC/Startup Parallel, Helping Others, La Recette Pour La Citron Pressé

lantern, personal growth, light

Over the weekend, I was brewing up some mad lemonade. ‘Cause well, that’s the summer thing to do. Since I’m limited in my expeditions outdoors, it’s just watching the sun skim over the horizon, blossoming its rose petals across the evening sky, in my backyard, sipping on homemade lemonade. If you’re curious about my recipe, I’ll include it at the bottom of this post.

When I’m cooking or performing acts of flavor mad science, I enjoy listening to food-related podcasts, like Kappy’s Beyond the Plate, Kappy’s CookTracks or Bon Appétit’s Foodcast. Unfortunately, all are on a temporary hiatus. So, I opted for the next best – YouTube videos. And recently, a curious video popped up in my Recommended feed. A 2010 TED Talk with Thomas Keller.

Thomas Keller. An individual probably best known, among many others, for his achievements with The French Laundry. Needless to say, I was enamored by his talk. But the fireworks in my head didn’t start going off until the 12:46 mark.

Continue reading “#unfiltered #21 The Recipe for Personal Growth – Thomas Keller’s Equation for Execution, The VC/Startup Parallel, Helping Others, La Recette Pour La Citron Pressé”

Why Aren’t Investment Theses Hyper-Specific?

pedestrian, vc investment thesis

As a result of my commitment to provide feedback for every founder who wants a second (or third) pair of eyes on their pitch deck, I’ve been jumping on 30-minute to 1-hour calls with folks. Although I’ve had this internal commitment ever since I started in venture, I didn’t vocalize it until earlier this year. And you know, realistically, this is not gonna scale well… at all. But hey, I’ll worry about that bridge when I cross it.

Something I noticed fairly recently, which admittedly may partly be confirmation bias ever since I became cognizant of it, is that there have been a significant number of founders currently fundraising who complain to me about:

  1. Many VCs don’t have their investment thesis online/public.
  2. Of those that are, VCs have “too broad” of a thesis.

So, it got me thinking and asking some colleagues. And I will be the first to admit this is all anecdotal, limited by the scope of my network. But it makes sense. That said, if you think I missed, overlooked, over- or underestimated anything, let me know.

The Exclusionary Biases

By virtue of specificity, you are, by definition, excluding some population out there. For example, in focusing only on potential investments in the Bay, you are excluding everyone else outside or can’t reach the Bay in one way or another. Here’s another. Let’s say you look for founders that are graduates from X, Y, or Z university. You are, in effect, excluding graduates from other schools, but also, those who haven’t graduated or did not have the opportunity to graduate at all.

The seed market example

Here’s one last one. This is more of an implicit specificity around the market. The (pre-) seed market is designed for largely two populations of founders:

  1. Serial entrepreneurs, who’ve had at least one exit;
  2. And, single-digit (or low double) employees of wildly successful ventures.

Why? You, as a founder, are at a stage where you have yet to prove product-market fit. Sometimes, not even traction to back it up. And when you’re unable to play the numbers game (like during the stages at the A and up), VCs are betting on the you and your team. So, to start off, we (and I say that because I’ve been guilty of overemphasizing this before) look into your background.

  • What did your professional career look like before this?
  • Do you have the entrepreneurial bone in your body?
  • How long have you spent in the idea maze?

The delta between a good investor and a great investor

Let’s say an investor were to be approached by two founders with the exact same product, almost identical team, same amount of traction, same years of experience, and let’s, for argument’s sake, have spent the same number of years contemplating the problem, but the only difference is where they came from. One is a first-time founder from [insert corporate America]. The other is the 5th employee of X amazing startup. Many VCs I’ve talked with would and have defaulted on the latter. And the answer is reinforced if the latter is a founder with an exit.

The question wasn’t made to be fair. And, it’s not fair. To the VCs’ credit, their job is to de-risk each of their investments. Or else, it’d be gambling. One way to do so is to check the founder’s professional track record. But the delta here that differentiates the good from the great investor is that great investors pause after given this information and right before they make a conclusion. That pause that gives them time to ask and weigh in on:

What is this founder(s)’ narrative beyond the LinkedIn resume?

Shifting the scope

It’s not about the quantitative, but about the qualitative. It’s not about the batting average, but about the number and distance of the home runs. So instead of the earlier question:

  • How long have you spent in the idea maze?

And instead…

  • What have you learned in your time in the idea maze?

Similarly, from what I’ve gathered from my friends in deep/frontier tech, instead of:

  • How many publications have you published?

And instead…

  • Where are you listed in the authorship of that research? The first? The second? The 20th?
    • For context of those outside of the industry, where one is listed defines how much that person has contributed towards the research.
    • As a slight nuance, there are some publications, where the “most important” individual is listed last. Usually a professor who mentored the researchers, but not always.
  • And, how many times has your research been cited?

Some more context onto specificity

Some other touch points on why (public) investment theses are broad:

  • FOMO. Investors are scared of the ‘whats if’s’. The market opportunity in aggregate is always smaller than the opportunity in the non-aggregate.
  • Hyper-specific theses self-selects founders out who think they’re not a ‘perfect fit’. Very similar to job posts and their respective ‘requirements’.
  • Some keep their thesis broad in the beginning before refining it over time. This is more of a trend with generalist funds.
  • Theses are broad by firm, but more specific by partner. The latter of which isn’t always public, but can generally be tracked by tracking their previous investments, Twitter (or other social media) posts, and what makes them say no. Or simply, by asking them.

The pros of specificity

Up to this point, it may seem like specificity isn’t necessarily a good thing for an investor. At least to put out publicly.

But in many cases, it is. It helps with funneling out noise, which makes it easier to find the signals. It may mean less deal flow, which means less ‘busy’ work. But you get to focus more time on the ones you really care about. And hopefully lead to better capital and resource allocation. The important part is to check your biases when honing the thesis. Also, happens to be the reason why LPs (limited partners – investors who invest in VCs) love multi-GP funds (ideally of different backgrounds). Since there are others who will check your blind side.

Specificity also works in targeting specific populations that may historically be underrepresented or underestimated. Like a fund dedicated to female founders or BIPOC founders or drop-outs or immigrant founders. Broad theses, in this case, often inversely impact the diversity of investments for a fund. When you’re not focusing on anyone, you’re focusing on no one. Then, the default goes back to your track record of investments. And your track record is often self-perpetuating. If you’ve previously backed Stanford grads, you’re most likely going to continue to attract Stanford grads. If you’ve previously backed white male founders, that’ll most likely continue to be the case. In effect, you’re alienating those who don’t fit the founder archetype you’ve previously invested in.

In closing

We are, naturally, seekers of homogeneity. We naturally form cliques in our social and professional circles. And the more we seek it – consciously and subconsciously, the more it perpetuates in our lives. Focus on heterogeneity. I’m always working to consider biases – implicit and explicit – in my life and seeing how I’m self-selecting myself out of many social circles.

Whether you, my friend, are an investor or not. Our inputs define our outputs. Much like the food we put in our body. So, if there’s anything I hope you can take away from this post, I want you to:

  1. Take a step back,
  2. And examine what personal time, effort, social, and capital biases are we using to set the parameters of our investment theses.

Photo by Andrew Teoh on Unsplash


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!

#unfiltered #20 You Will Be What You Eat, You Are What You Excrete – Leading vs Lagging Indicators, One of My Relationship-Building/Networking Practices

stars, starry night, networking tips

Yesterday evening, I sat in our backyard, sipping homemade lemonade and sketching out my weekly creative endeavor (why). Between sips and furtive glances upwards, I hoped to catch a glimpse of NEOWISE. But alas, I forgot to pray to the weather gods in the morning.

Disappointed, I packed up to head inside. As if by a stroke of fate, my phone buzzed. You know, this story would be more dramatic if my disappointment was telepathically transmitted to my friends. Tongue in cheek, I apologize if I got your hopes up. But, it was merely the influx of messages after my timed “Do Not Disturb” mode switched off. Yet one of these blips came from a good ol’ swim team pal into our group chat. Lo and behold – an HD cross section in time of the exact comet.

I propped my cell above my head, positioned just north of the horizon. And unable to hold my smile back, I stuck around for a while longer.

So what?

You’re probably wondering: How the hell does yesterday’s smile have to do with “You will be what you eat, you are what you excrete”. As the title of the post so kindly suggests. Trust me it does. Admittedly, probably not the greatest of blog post titles, but, hey, it rhymes. Which might be the lamest excuse you’ve heard this month. But I digress.

You will be what put in your body. You are already what comes out of your body. Literally. Well, I’m sure my cousins who are molecular cell biologists will point out some (or many) of the nuances I missed. But we don’t have to count the cards.

The same is true for your personality. You build your personality based on the inputs in your life from when you’re younger. Your personality is subsequently evidenced by what you say and do.

And, I can say the same for education, biases, and so on. For the purpose of this post, I’d like to underscore one other – relationship-building. Or as most others understand it, networking. But I have a mild allergic reaction to that nomination.

Continue reading “#unfiltered #20 You Will Be What You Eat, You Are What You Excrete – Leading vs Lagging Indicators, One of My Relationship-Building/Networking Practices”

#unfiltered #19 The Goal of Job-seeking

job seeking

Last night, I caught up with an old friend who has a few more miles on his career odometer than I have. And he shared something quite profound.

“The goal of job-seeking is to never have to submit another resume again.”

In frankness, I’ve never thought about job-seeking in that context. But it makes complete sense. You perform so well in each position that your (former) co-workers start spreading the word about you. “If you need help with [insert subject matter], you have to work with [you].” Effectively, you’re building virality around you through each ‘customer’ interaction being amazing.

And the more I thought about it last night, the more parallels I found. For founders…

The goal of an entrepreneur is to never have to pitch to investors again.

For investors…

The goal of an investor is to never have to pitch how awesome or founder-friendly their firm is to LPs or a potential investment.

And taking a step back, looking at this through macro-lens…

The goal of any professional is to never have to sell again.

You may neither be a startup founder nor a salesperson, but I believe any of us could appreciate the contextualization of our own efforts. What is your endgame? And how can you pave the the most scalable road to your success?

There’s a saying that luck only gets better with success. I’d like to believe that after you reach critical mass and word-of-mouth, you manufacture your own luck.

Photo by Avel Chuklanov 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!

#unfiltered #18 Naivety vs Curiosity – Asking Questions, How to Preface ‘Dumb’ Questions, Tactics from People Smarter than Me, The Questions during Founder-Investor Pitch

asking questions, naivete vs curiosity, how to ask questions

Friday last week, I jumped on a phone call with a founder who reached out to me after checking out my blog. In my deep fascination on how she found and learns from her mentors, she shed some light as to why she feels safe to ask stupid questions. The TL;DR of her answer – implicit trust, blended with mutual respect and admiration. That her mentors know that when she does ask a question, it’s out of curiosity and not willing ignorance – or naivety.

But on a wider scope, our conversation got me thinking and reflecting. How can we build psychological safety around questions that may seem dumb at first glace? And sometimes, even unwittingly, may seem foolish to the person answering. The characteristics of which, include:

  • A question whose answer is easily Google-able;
  • A question that the person answering may have heard too many times (and subsequently, may feel fatigue from answering again);
  • And, a question whose answer may seem like common sense. But common sense, arguably, is subjective. Take, for example, selling losses and holding gains in the stock market may be common sense to practiced public market investors, but may feel counter-intuitive to the average amateur trader.

We’re Human

But, if you’re like me, every so often, I ask a ‘dumb’ question. Or I feel the urge to ask it ’cause either I think the person I’m asking would provide a perspective I can’t find elsewhere or, simply, purely by accident. The latter of which happens, though I try not to, when I’m droning through a conversation. When my mind regresses to “How are you doing?” or the like.

To fix the latter, the simple solution is to be more cognizant and aware during conversations. For the former, I play with contextualization and exaggeration. Now, I should note that this isn’t a foolproof strategy and neither is it guaranteed to not make you look like a fool. You may still seem like one. But hopefully, if you’re still dying to know (and for some reason, you haven’t done your homework), you’re more likely to get an answer.

Continue reading “#unfiltered #18 Naivety vs Curiosity – Asking Questions, How to Preface ‘Dumb’ Questions, Tactics from People Smarter than Me, The Questions during Founder-Investor Pitch”

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””

Looking at Business Models – Consumer Behaviors and Gross Margins

startup business models, waves, consumer behaviors

While sipping on my morning green tea, I’m inspired by Venture Stories’ recent podcast episode where Erik was interviewing Charles Hudson of Precursor, where they codify Charles’ investment thesis, markets, business models, among many other topics. A brilliant episode, if I say so myself! And it got me thinking.

Some market context

In the past few months, I’ve been chatting with a number of founders who largely seem to gravitate towards the subscription business model. Even pre-COVID, that seemed to be the case. And this notion was and is further perpetuated where a plethora of VCs turned their attention to XaaS (X-as-a-service).

Why? Pre-COVID, the general understanding was that consumers were:

  1. More expensive to acquire,
  2. And, harder to retain,

…which I shared in one of my February posts. I’d even heard some investors say: “Consumer social is dead.” Although I personally didn’t go as far as to illustrate the death of a vertical, I had become relatively more bearish on consumer than I did when I started in venture. Clearly, we were wrong. The question is: how much of this current situation will still hold true post-COVID? And honestly, your guess is as good as mine. But I digress.

Given the presumption that the consumer industry was faltering, many VCs re-positioned their theses to index more on enterprise and SaaS models. Models that had relatively fixed distribution channels and recurring revenue. It became some form of ‘guarantee’ that their investments could make their returns. And as the demand for startups shifted, supply followed.

The Business Models

Though there seemingly has been an overindexing of subscription models in the consumer space, I’m still an optimist for its future. The important part is to follow consumer behavior.

  • What do their consumption patterns look like?
  • What do their purchasing patterns look like?
  • How do customers think about value?

Here is a set of lens in which I think about business model application:

Subscription“One-off”
Continuous consumption patterns
>3-4 times in a month
(Ideally, >3-4 times per week)
Discrete consumption patterns
~1-2 times a year
Extremely episodic in nature
Proactive, expectant behaviorReactive behavior
Examples:
Food
Groceries
Music
Education
Examples:
Moving homes
One-off Conferences
Travel
Car
Note: The examples are generalized. The business models will depend on your target market. For example, travel for the average family may not happen on a recurring basis, but travel for a consultant happen weekly (pre-COVID).

The Extremes of Gross Margins

Of course, I can’t talk about business models without talking about profits. The ultimate goal of any business model is to realize returns – gross margins. Unfortunately, there’s no silver bullet on how you price your product. While you find the optimum price (range) for your product A/B testing with your customers, here’s a little perspective onto the two extremes of the spectrum.

  1. If you have insanely high margins, expect lots of competitors – either now or in the near future. Expect price-based competition, as you may most likely, fight in a race to the bottom. Much like the 1848 California Gold Rush. Competitors are going to rush in to saturate the market and squeeze the margins out of “such a great opportunity”.
  2. If your margins are incredibly low, as Charles said on the podcast, “there better be a pot of gold at the end of the rainbow.” You need extremely high volumes (i.e. GMV, “liquidity” in a marketplace) to compensate for the minimal cut you’re taking each transaction. A fight to monopolize the market. I’m looking for market traits like:
    1. Growing market size.
      • Ideally heavily fragmented market where you can capture convoluted, antiquated, and/or unconcentrated processes in the status quo.
      • Why unconcentrated? Don’t underestimate the power of your incumbents’ brands and product offerings. Like don’t jump in ad tech if you’re just going to fight against the Google and Facebook juggernauts, who own 80% of the ad market.
    2. Insane network effects.
    • For example, payments or food delivery. Food delivery is one where you have to reach critical mass before focusing on cash flow/profitability. I get it. It’s a money-eating business… until network effects kick in. Sarah Tavel wrote a Medium article about this where she explains it more elegantly than I have.

In closing

I’ve seen many founders end up taking their models for granted or sticking to a single generic revenue structure. But the best founders I meet make this a very intentional part of their business. Sometimes, even having different revenue streams for different parts of the business. If that’s the case for you too, Connie’s piece about multimodal models may be worth a read.

Photo by Denys Nevozhai on Unsplash


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#unfiltered #17 My Favorite Questions from Social Experiments – On Love, Emotions, Candor, and Goals

mirror, reflection, introspection, thinking questions, my favorite questions from social experiments

I’ve given myself the last two weeks to focus on introspection. Rediscovering cross sections of my life – crystallizing them in amber – to find where I can improve the most in. And in the process of doing so, I found inspiration in. I’ve known for a long time that I was, by no means, the smartest person out there. Arguably, my best ideas find the roots of their ‘originality’ in insights from others. From…

  • Friends
  • Founders
  • Investors
  • Subject-matter experts (SMEs)
  • Podcasts
  • YouTube videos
  • Academic journals
  • Blogs
  • And, really creative and really, really passionate people, where their passion is contagious.

… just to name a few.

But, that’s the best part!

Though it wasn’t my initial intention to do so, some of my favorite, most curiously introspective, most thought-provoking questions came from my guests during social experiments, particularly those who partook in Brunches with Strangers and Hidden Questions. Frankly, I can’t take credit for any of them. And just as I learned so much about them and myself from each, I hope you’ll be able to do the same. I don’t expect every question to resonate with you, but I suspect at least a small handful will. If so, my only ask is that you pay it forward in your own meaningful way.

Between 120+ guests between the two of the experiments, here are some of my favorite.

On Love and Emotions

  • When was the last time you said “I love you”?
  • When was the last time you wished you had said “I love you”, but didn’t or couldn’t?
  • Who was the last person you lost in your life that hurt you deeply (i.e. breakup, death, loss of friendship, etc.)?
  • When was the last time you uncontrollably cried?
  • When was the last time you genuinely smiled?
  • What emotion have you given an overemphasis on in the past year?
  • When was the last time you were disappointed in yourself? Why?
  • When was the last time you looked yourself in the mirror and thought “I’m killing it”?What might have sponsored that emotion?

On Lack Thereof

  • Is there someone you pretend to like but don’t? If so:
    1. What is stopping you from sharing your thoughts candidly with them?
    2. What is stopping you from liking them?
  • How many friendships do you regret having broken and never healed? Why?

On Candor to Others and Yourself

  • What are 2-3 things you look for in a person/friend before you are comfortable sharing a secret? How would you prioritize those 2-3 traits?
  • What are you dishonest to others about?
  • Why do you lie to yourself?
  • Over the past year, what have you gotten better at saying ‘no’ to?
  • What are some contrarian beliefs you hold deeply to be true?
    • (Also seen asked as) What is an unpopular opinion you have?
    • Who have you told? Or have you told anyone else?
  • If you could pass 1 value/trait down to your child(ren), what would it be?
  • If there was 1 trait that you could prevent your child(ren) from taking on, what would it be?
  • What is an unusual habit, or an absurd thing you love?
  • What is the best lie you ever told?
    • Do you believe it?
  • What is the most hurtful comment you once said, wrote, or expressed to another?
  • How often do you log on or log off of social media due to envy?

On Goals

  • Do(es) your long-term goal(s) scare you?
  • What’s the craziest thing you did for X?
    • Let X be any goal you’ve once had (i.e. job, relationship, family, grades, to learn, etc.)
  • What is something someone once said to you (good or bad) that keeps you motivated to this day?
  • What failure has set you up for success?
  • If you could title your own biographical movie, what would it be called? And what will it be called post-mortem?
  • What is your 10-year goal?
    • What’s stopping you from accomplishing it in 1 year?
    • If I held you at gunpoint, and told you that you had to reach this goal in 1 month, what do you have to do, starting from now?
  • If you could undo one decision you made in the future, what would that be?
  • What would you like to have written/said in your eulogy?

Photo by Nijwam Swargiary 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!