2025 Year in Review

2025

“‘I remember’ is more meaningful than ‘I love you.'”

I was catching up with an college friend over the holidays who’s now in a wonderfully happy relationship now, when once upon a time, she once doubted her ability to fall in love again. And as we were talking about what makes this guy special compared to all the other ones, she said: “Because he remembers the small things.”

“I love you”, while great for Hallmark movies, often feels empty if not paired with action. And more often than not, actions speak louder than words. Remembering that whenever they order they pick the carrots out of the salad, so you order salad without the carrots. Remembering their bucket list and making it a quarterly goal to check something off that bucket list.

Separately, I caught up with a friend who runs investors relations (IR) for a large multi-stage firm. Someone I’ve heard from manyโ€”colleagues, LPs, founders, even her friendsโ€”that she is one of the most thoughtful people in the world, which seems to be “easy” for her because she has a great memory and they “don’t”. For a blogpost that will come out next year, we were talking about IR best practices and what her CRM looks like. And I can say it’s accident that she comes off with great memory. There are details she tracks in there that no sane capital formation professional would actively track. One’s go-to coffee order. Their children’s birthdays. Their anniversary. Their first day on the job. And so on. What is that James Clear line again? “You do not rise to the level of your goals. You fall to the level of your systems.”

This past year was a year where I found myself remembering. How I got here. Did I even want to be here? Why did I want to be here? Who helped me get here? What they did? What might’ve seemed like an accident, but was a subconscious habit or intention? Even to the point I’ve asked several guests on the podcast, if they always knew they wanted to be where they are today. How did they know? When did they realize it? Given how personal some of the answers got, we had to leave quite a few on the editing floor. (Sorry.)

I left Alchemist close to the beginning of this past year. 2025 was also the first year since I started where I didn’t share my birthday resolutions on this blog. Largely because I didn’t know if I needed to add more to my list of things to do, but rather subtract things.

And now I’m writing this on the last day of the year, as it felt right to recap on the year only after the year was done. (Almost done.)

Most of my writing this year centralized around LP/GP dynamics. More so than any previous year.

Which is funny. I started this humble blog as a public FAQ. I used toโ€”still doโ€”get quite a few messages often asking for the same advice. I’ve always disliked giving general advice. A piece of advice is only as great as the situation in which you use it in. But most people ask generic questions. And generic questions often get generic advice. Nevertheless, I’ve always erred on the side of sharing the circumstance in which the advice is given when I do share generic advice, except when the advice, in my experience, applies to most people I talk to. And it’s funny that of this year’s most popular blogposts, four definitely include generic advice. Two arguably more circumstantial. But proportionally, even looking back at my most popular blogposts, the furthest reaching ones often house FAQs that most people can relate to. Or know someone that can relate to it.

Without further ado, my most popular pieces of writing this year:

  1. Hustle as a Differentiator โ€” I don’t know how ‘hustle’ went up in search volume this year, but it did. At least in terms of how people found this essay. But I also think people like stories and tactical examples of when and how hustle beat everything else. And this is the blogpost for that. Also, the only one of the top six not written this year.
  2. If 198 Pieces of Unsolicited, (Possibly) Ungooglable Advice for Founders Were Not Enough โ€” The third installation of my 99 pieces of tactical founder advice series. Admittedly, not surprised this went far. Sometimes great content is hard to find. And every time I publish a collection, like this, I hope it becomes the Dewey Decimal Classification for good, tactical content in the innovation ecosystem.
  3. Dear LP โ€” I wrote the sister blogpost of this first. But an emerging manager asked me to write that calls LPs out on their bad behavior. Not a good reason to write a piece in my opinion, until the subsequent weeks’ worth of LP conversations left me frustrated at LP behavior myself. This is also the blogpost where I had more than a handful of friends reach out to ask if I was okay. Which I was and am. This essay was the therapy I needed.
  4. Good Misses and Bad Hits โ€” Most outcomes in venture aren’t clear until a decade later. And when they are, so much of our past memory atrophies that for many of us, we can’t pattern match to why we made the decisions we did. Inspired by our Golden State celebrity, we decided to write a piece on what it means to measure inputs before the outputs and how we can course correct before it’s too late.
  5. Dear Emerging Manager โ€” Born out of frustration with emerging managers who seem to be living under a rock. But also a realization that not every GP has the vantage point that LPs do. In fact, most don’t. So this letter was hopefully helpful to debunk some of the myths GPs have.
  6. Goldilocks and the 3 Secondaries โ€” One of my favorite pieces I co-wrote this year with Dave, as it is one of the most tactical and intellectually rigorous pieces this year, but also a great mathematical exercise of how much of your private stake in a company to sell, when, and to whom.

2025 was the year I took a step back from promoting any of this blog’s content online. I also took down any vestigial pages that asked for a subscription within the first 10 seconds of browsing a page on this blog. I simply wanted this blog to be my safe harbor, my personal diary on my journey week by week. I realized that every time I actively promoted my blog on social media, I felt a part of me die.

Unlike Superclusters, this blog isn’t meant for one particular audience. While this blog has grown over time and I’m thankful to each and every one of you who has joined me in this journey, and while I had many an opportunity to do a sponsored blogpost, selling any piece of this virtual real estate felt disingenuous. It felt that I was selling a part of my soul. Because every week when I write, I write about whatever I want to write about. I don’t have an agenda. I merely write to write.

And the way I felt most true to myself was to no longer pursue any marketing of this blog. The only reason any of the afore-mentioned blogposts in the last section made its way to new audiences is that I’m lucky to have readers like you share things with the world, while I’ve hermitized.

As such, any growth of this blog this year is because of you, not me. For that and more, I am deeply thankful. Nevertheless, the all-time most popular blogposts haven’t varied much compared to last year, except for our lucky number five. Interestingly enough, I didn’t even write that one this year.

  1. The Science of Selling – Early DPI Benchmarks โ€” Honestly, it still surprises me that this is my most popular one to date. Not because I think it’s a bad topicโ€”in fact, I truly believe it’s a much needed discussion as venture funds face liquidity crunches and the asset class institutionalizesโ€”but because, I think it’s still a niche topic that is not widely searched for. But I’m glad that people are searching for answers here. This one also led me to write its sister piece here, which ranked 6th for this year’s most popular.
  2. The Non-Obvious Emerging LP Playbook โ€” My first piece that felt like it went viral. And the one that taught me how much dialogue is needed in this world around investing in venture funds.
  3. 10 Letters of Thanks to 10 People who Changed my Life โ€” Another surprise that this topic of gratitude is as enduring as it is. Hopefully, this will play a small part in helping create a more grateful world. We stand on the shoulders of giants. It’s always important to never forget that fact.
  4. 99 Pieces of Unsolicited, (Possibly) Ungooglable Startup Advice โ€” The OG collection I put together on 99 pieces of tactical advice for founders. This is the one that led to the one I wrote for investors, and all future series under the ’99’ nomination.
  5. Hustle as a Differentiator โ€” Only a matter of time that this one beat out the one I wrote about how to host fireside chats. ๐Ÿ™‚

It’s always deeply interesting to me that sometimes the blogposts I spend the most time writing and/or are the ones that resonate with me the most personally don’t always go the furthest. A constant reminder that what the world might like, what you might like, may vary from what I like. From time to time, I get small notes from you that an esoteric, but deeply personal blogpost peaks your interest. And it really makes my day. For a very brief 24 hours, if only to relish in the small joys in life, I save those notes for when I feel imposter syndrome. Trust me, it happens. Not because the readership is highest, but because it’s nice to know I’m not alone in my peculiar, sometimes really nerdy interests.

The below I will list, in no particular order, as each meant something to me at the time of writing each, as well as moving forward:

  • Goldilocks and the 3 Secondaries โ€” Same rationale as above. And if you want the actual model we used to model when and how much to sell on the secondary market, it’s in there.
  • Flaws, Restrictions, and Limitations โ€” Inspired by Brandon Sanderson’s framework for character development, I’ve found this framework quite useful when assessing how risky an investment is into an emerging manager.
  • Dear LP โ€” Pure therapy.
  • Dear Emerging Manager โ€” Same as the above. Free therapy for myself. Hopefully helpful to the world.
  • The Question Off โ€” One of my favorite drills I did this year to be a more thoughtful conversationalist, with none other than the best sparring partner out there, Kevin Kelly.
  • On Re-Ups โ€” I’m an emerging LP. I haven’t been allocating to venture funds for over a decade, and so I’m still learning. This year, for the first time, I had managers I invested in, in previous vintages, come back and ask for me to re-up. Rather than do so haphazardly, I had to build a system for when it makes sense for me to re-up. This is it.
  • Gratitude and Deal Flow โ€” One of my favorite re-framings on who I choose to invest in. And I couldn’t spell out why I liked certain managers over other great ones until a friend spelled it out for me.
  • Intro Policy โ€” Another piece for personal therapy. Since writing this, it’s been much easier for myself to decide when to make intros.
  • 300 WhatsApp Messages Later: Our Risk Framework for Backingย Emergingย VCs โ€” One of the beauties of collaborating with someone brilliantโ€”I’m looking at you, Benโ€”is that I learn something new as I am writing this alongside my co-author. Iron sharpens iron. And it was through this piece, that I built a more robust risk framework to evaluate emerging managers.
  • Scientists, Celebrities and Magicians โ€” Kudos to my friend, Michael, for teaching me his framework for how a professional can be a triple threat, which I’ve since applied to the world of venture. And how different investors and leaders spike.
  • Referencing Excellence โ€” The more I invest as an LP, the more important I realize how important reference calls are. The more important I realize they are, the more I realize I need to refine the way I get to the truth. Unfortunately, there’s no silver bullet, but this blogpost led me down my first real personal exploration for how to do references my way.

There is but one personally memorable blogpost I will intentionally leave out of the above list. It is the only one I’ve gone back to edit not once, not twice, but four times this year. Let’s call it an easter egg. If you do find it somehow, just know that I plan to continue updating that piece next year as well.

Photo by Kelly Sikkema on Unsplash


If you want to check out the past few years, you’ll find them encased in amber here:


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!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

The Most Disappointing Podcast You’ll Ever Listen To (ft. Allie Garfinkle) | Superclusters | S6PSE2

allie garfinkle, david zhou, superclusters

Warning: This is a brief-ish, but hopefully entertaining intermission from the usual Superclusters programming. When we passed the 50th episode mark more than a few episodes ago, Tyler (my editor) and I thought it’d be interesting to record an episode where I change seats. Instead of me asking the questions, someone else would ask me questions. And I couldn’t imagine any better person to do so than my good friend, Allie, who in my humble opinion, is one of the best interviewers alive today.

Allie Garfinkle is a senior finance reporter for Fortune, covering venture capital and startups. She authors Fortuneโ€™s weekday dealmaking newsletter Term Sheet, hosts the Term Sheet Podcast, and co-chairs Fortune Brainstorm, a community and event series featuring an annual retreat in Deer Valley, Utah. A regular contributor to BBCโ€™s Business Matters podcast, Allie is also a frequent moderator at major conferences such as SXSW. Before joining Fortune, she covered Amazon and Meta at Yahoo Finance and helped produce Emmy-nominated PBS Frontline business documentaries, including Elon Muskโ€™s Twitter Takeover and The Power of the Fed. A graduate of The University of Chicago and New York University, Allie currently resides in Los Angeles.

You can find Allie on her socials here:
LinkedIn: https://www.linkedin.com/in/alexandra-garfinkle1/
X / Twitter: https://x.com/agarfinks

Listen to the episode onย Apple Podcastsย andย Spotify. You can alsoย watch the episode on YouTube here.

OUTLINE:

[00:00] Intro
[02:01] Art
[09:39] Competition
[17:49] Paleontology
[18:14] Allie’s Tiki mugs
[22:49] How has VC evolved?
[29:41] Evaluating risk
[43:04] Why is it important for VCs to stay in touch?
[47:10] Are there reliably good investors?
[53:09] Young GPs in market
[54:58] How useful is education that come via public talks?
[57:50] Does your niche fund size make sense for the market?
[1:01:16] Is there too much venture capital?
[01:05:24] How much of VC is art vs science?
[1:07:18] What’s going on in Allie’s world?
[1:09:45] Post-credit scene: Receipts

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

Iโ€™m intentionally keeping this section void of the things that I said since I hate the idea of quoting myself.

โ€œPart of the point of this [investing job] is that you want to be anonymously, asymmetrically correct. And you canโ€™t necessarily be that by saying or doing the same thing as everyone else. That being said, the worst nightmare for a VC is that no one wants to back a company theyโ€™ve backed.โ€ โ€” Allie Garfinkle

โ€œIf it eventually doesnโ€™t become consensus, you were wrong.โ€ โ€” Allie Garfinkle


Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP
Follow Superclusters on TikTok: https://www.tiktok.com/@super.clusters
Follow Superclusters on Instagram: https://instagram.com/super.clusters


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!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

120 BPM

dj, bpm, beats per minute

I was on a walk with an LP friend recently around Redwood City. And he told me a remark that another LP had about a mutual investor relations friend we had. That our IR friend started the conversation with, “What are your life goals?” And it alarmed that LP who was meeting our IR friend for the first time. To which, this LP told a few others that he was not only thrown off, but also felt offput by the interaction.

It led to a discussion between my LP friend and I where neither of us, knowing this mutual IR friend, would ever think less of our IR friend because that’s just how this person operates. But to someone who has no context of our friend, it would seem bizarre.

One of my friends who, at one point in time, was a full-time professional DJ, once told me, “The golden number is 120. 120 beats per minute. It’s the rhythm that when you strip all the noise away and you can get a heart to beat that fast, it feels like you’re in flowโ€”flow state. Pure ecstacy.

“But you can’t start the set at 120. If your mix is at that pace, and the heart isn’t, it feels discombobulating. You need to work up to it. Start the set at 70. And over the course of a one- to two-hour set, you work your way up to it. And notice the audience. The crowd must be nodding their head to your beat. And if you ever lose that bob, slow the set down again. And try to catch that heart rate again.”

To this day, probably one of the best pieces of advice on how to hold a conversation I’ve gotten to date. And it was never meant to be so.

A question I get surprisingly often is: “Why did you start the podcast?”

Among many reasons โ€” I get to ask dumb questions to smart people, refine my diligence skillset, get better at asking questions, and so on โ€” one of which was that when I only have an hour and change with someone, I’d rather not spend 10-15 minutes on small talk. How are you? How was the weekend? Which seems to be the LLM that’s coded in us on how to start a conversation and hope eventually, you can get to the meat and potatoes of the conversation. And it makes sense.

To use the DJ analogy above, most people’s resting heart rate is around 60-100. To take the middle of the road, 80. And for busy people who are constantly distracted by meetings and tasks that need their attention, a conversation with a stranger is among the lowest of their priorities. So I always believed that people would be near their resting heart rate when chatting with a nobody like myself. As such, they need icebreakers like “How are you?” to warm them up to the conversation, where their first impression of how you answer that question will indicate where the conversation might go.

On the flip side, most people haven’t been on podcasts. Much less, the guests I aim to have on. LPs. Many typically aren’t given the stage. And even if they are, it’s closed door discussions and private events. Rarely, do they get a public stage. So, the hypothesis was that on average, an LP will most likely be more nervous, excited, you name your fair share of anticipatory emotions jumping on a podcast as opposed to an offline 1:1 conversation. Six seasons in, I’d say we’re pretty close to the mark there.

As such, a faster heart rate means I am often given the privilege of starting the conversation not from “How are you?” but a question closer to 100-110 beats per minute, with hopes we can get into the questions that result in 120+ bpm sooner. And it’s almost always easier to ask a question “for the audience” than for yourself.

“Tell us about the time you proposed to your wife via a billboard. And how does that influence the way you think about pitches today?”

“Half your games on chess.com open with the Ruy Lopez. How do you think about opening gambits when you play white. And how much, if at all, does it influence the way you think about opening a conversation with a GP?”

“How does getting your first day in investment banking postponed, which was supposed to be Sept 11, 2001, influence the way you think about serendipity?”

All questions that I would hesitate to say, would be easy opening gambits in a 1:1 coffee chat. But your mileage may vary.

Photo by Tobias Rademacher 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!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

The Question-Off

flowers, plains

One of my favorite questions as of late has been: “What is it you do to train that is comparable to a pianist practicing scales?” To me, it is fascinating to deconstruct a practice, or an action, or a set, and just drill on only one element of that practice. Every accomplished musician, athlete, veteran, chef, just to name a few, is uniquely familiar with the concept of repetition and refinement.

For example, part of my job, as now a podcast host, on top of doing research, prepping and making sure the guests are comfortable, getting involved in the editing room, just to name a few, is to ask questions. And because of the way I host Superclusters, my goal is to ask guests questions they’ve never been asked before. Admittedly, tall marching orders to those individuals whose job is to ask questions to get to the bottom of something in ways the recipients of their capital and their network may not expect. But alas I try. That said, I thought, how cool would it be if I could practice asking novel questions to someone who’s seen it all?

Admittedly, there are very few souls out there who would make great sparring partners for this drill. One that’s seen, heard, and thought of almost every known question out there. And even less I have had the chance to personally interact with. Of my limited Rolodex, luckily, the first person I asked was game. And that person happens to be this guy called Kevin Kelly.

The exercise would be, over a 30-day period, for me to ask him one question every day with the hopes that at least half are ones that he’s never been asked before. He then one-upped me and said he’d do the same. As such, it resulted in 60 queries that go beyond the obvious. While I’m not here to share the results of this “question-off”, I wanted to share the below as I hope this inspires you in ways that you might not have considered before. And if nothing else, fun journaling prompts for yourself. As such, I’ve bolded some of my personal favorites.

Kevin’s questions for me:

  1. What would you do with a billion dollars? (After you gave your family cars, houses, yachts, and vacations, you would still have a billion dollars.)
  2. Do you see yourself as part of an intellectual heritage? Who is on your tree?
  3. What is a prediction you made that was very wrong?
  4. What is the occupation that is the opposite of what you do?
  5. You get to relive one day of your past life. You could either return it as was at full volume, or you could change it. What day do you choose?
  6. If your life has a motto five words or less, what would it be?
  7. What significant law do you think should be changed?
  8. What do your friends get wrong about you?
  9. What influential person would you most appreciate a compliment from?
  10. What is something you can’t do that you’d give up 10% of your current wealth to do exceptionally well?
  11. What do you know more about than anyone else you have met?
  12. What is special about the neighborhood you live in?
  13. What question do you wish people would ask you?
  14. You get a 2-way ticket in a time machine. Do you go to the past or future? How far?
  15. What is a rule you gave yourself as a child that you still keep?
  16. What is the most recent thing you did for the first time?
  17. Who is a thinker more people should know about?
  18. What’s the strangest compliment you’ve ever received?
  19. What widely accepted “fact” do you think will be proven false in the next 50 years?
  20. What’s the most useless skill you’re proud of?
  21. What is one non-obvious piece of advice you would give to someone who wanted to get rich?
  22. They are making a film about you. What should the theme song be?
  23. What is a famous book you think everyone should read, but for a reason other than the one it’s famous for?
  24. What is something everyone you know of has done, but you have not?
  25. What is the most profound thing you’ve learned from a work of fiction?
  26. What is a popular piece of advice that you think is completely wrong?
  27. What part of you is a mystery to you, the part of that you least understand?
  28. What memory do you return to most often?
  29. What’s the most persistent myth people have about you that you’ve never bothered to correct?
  30. What’s a small thing you lost that still bothers you?

My questions for Kevin:

  1. What was your earliest relationship with money?
  2. Was there any specific groundswell in your early childhood and early life that led to the highest rate of change and growth? Were they largely technological, political or cultural in nature?
  3. If you had a billion dollars to create a secret society that will last 200 years into the future, how would you go about doing so and what would they be working on?
  4. As someone who’s used ChatGPT to write a novel you’ll never publish, yet has been an original thinker, thought-provoking writer for decades, what parts of your writing โ€” no matter how far into the future, no matter how good the AI gets โ€” will you never AI touch?
  5. One of the pieces of advice you once gave was to be able to learn from those you disagree with or offend you. Has there ever been a relationship that has most challenged the grounds of which your ideals stand on? How do situations that have led you to refine your ideals differ from those that reinforce what you believe in?
  6. If you were the main character of a movie about your life and you had an audience watching said movie, what would the audience be screaming at you to do?
  7. Kevin, you’re a futurist. You see the world beyond the horizon. But to take a step back, there’s a quote from the show The Office that I really like: “I wish there was a way to know you’re in the good old days before you’ve actually left them.” With all the doom and gloom around us today, what are the reminders you keep close to your heart that today, we’re still in the good old days?
  8. There’s so much gravitas and leniency given to a founder and their crazy ideas, but I’m curious, in your opinion, what were the greatest innovations at WIRED that weren’t a Kevin idea?
  9. Has there been a habit or practice you’ve observed from an interviewee of yours that you’ve worked into your own rotation?
  10. What, if anything, do your peers oversimplify about being a writer? And what, if at all, do they often overcomplicate?
  11. What was your first failure? How did you know when to quit?
  12. If you were to put together the perfect interviewer piece by piece Mr. Potato-Head-Style, how would you go about it? Who’s the researcher? Who opens the interview? Who’s the one in charge of going deep in questions? Who closes out the interview? Who’s responsible for the in-person interview setting?
  13. What is the question that has taken the most mental calories for you to answer? Why?
  14. You took a variety of roles across your career โ€” some of which you’ve co-created and started, others you joined. Were “what’s best for the company” and “what’s best for Kevin” aligned the whole time?
  15. When you have time to wonder, what’s the thought of idea you regularly find yourself coming back to because you find it so interesting, but most of the world may not?
  16. What about your past do you desperately not want your children to know about?
  17. One of the great Kevin Kelly-isms out there is “Don’t be the best. Be the only.” How much time and discipline do you think is necessary for an individual to fully appreciate that they themselves are the only one doing something? At what point does it become part of their identity?
  18. As an enthusiast who’s been enamored by photography since you were in high school and took a deep dive into it in 1970, if you had a camera that could only take three photos total starting from today, what three moments would you photograph?
  19. When was the last time you adopted the habits, wisdom, or advice from someone you disliked or held very little respect for?
  20. What is an example of a mentorship relationship that you’re particularly proud to have your fingerprints on?
  21. What’s something others would believe you’d be highly proficient in, but no matter how hard you’ve tried in the past, you’ve found it extremely difficult to raise your skill level at that?
  22. What is it you do to train that is comparable to a pianist practicing scales?
  23. If you lived your life 1000 times, would would be true in 999 of them?
  24. What is the greatest accomplishment that you regret having achieved?
  25. What was the harshest piece of criticism you gave where you knew that that individual or project was providing more meaningful value to the world than your criticism gave it credit for?
  26. What coffee table books best encapsulate Kevin’s personality today? And would your coffee table have looked different today than in your 30s?
  27. If you could only choose 2 personality traits to pass on to your grandchild โ€” 1 strength and 1 weakness, which 2 would you pass on?
  28. What was one major life decision you’ve made where it was better to not over-intellectualize the decision-making process and shoot from the hip?
  29. You’ve had a non-traditional path to your life and your career. The stuff that typically goes in movies. And in so much of what you do, you’re a dreamer. You’re a visionary. How much did they first pay you to first give up on your dreams? Why did you say yes or no?
  30. As someone who’s once recommended people to go to funerals, what is your biggest fear around what someone might say at yours?

Photo by Ahmet Yรผksek โœช 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!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

Why I Don’t Pay for LinkedIn Premium

ruler, short

โ€œI didn’t have time to write a short letter, so I wrote a long one instead.โ€ โ€” Mark Twain

I write on this blog because I can write to think. I can write as a stream of consciousness. But at the same time, it is just that. It’s long.

But when it comes to reaching out and getting a stranger’s attention, there’s beauty in brevity. 200 characters. If you can’t get the attention of someone you don’t know in 200 characters. Hell, even 100 characters. Then no pitch deck, no long blurb ever will. Just because a house has more square footage doesn’t mean you’ll stop and visit the house.

People are busy. Investors are busy. Recruiters are busy. The world’s smartest, brightest, most ambitious are busy. A great cold message can go further than almost any warm intro can. Most people are just not good at writing them. They’re too verbose. (Caveat, a lot of my outreaches are too, but I highlight the 20 words they need to pay attention to in that email. And they may not all be in the same sentence.)

To be fair, LinkedIn Premium is really the Trojan Horse for this short piece. Keep exercising the cold outreach muscle.

I still do it every week. And so far, the response rates to ones I handcraft are better than what AI can write for me. The platform of outreach may vary. Question I always think about is where are the people I’m reaching out to spending a lot of attention, but there’s just that slight deficit of inbound information. Sometimes, it’s literally a messenger pigeon.

Photo by William Warby 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!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

Intro Policy

dogs, meet, intro

I used to send intro requests for as many people as I humanly could. Admittedly, a sillier, more naive me a long, long while back.

The most number of intro requests came from people I did not know. Usually founders. Given that I had just entered the venture world at that time, I was labeled as an investor or, at least, someone, who was connected to the investor world based on my LinkedIn. I also had a habit of adding anyone who reached out to connect (unless they were obviously spam). At the time, I thought, “What was the downside?”

Spoiler alert: There is a downside.

They would try to tell me about their startup. Then asked if I would invest. I’d say no, so they’d ask if I knew anyone who might be interested. A fair question. And a natural lead-in, had I offered any names, to: Can you intro me to them?

In trying to be a good Samaritan, I’d ask for the deck and blurb in a forwardable email. Half of them would. Half of them would say something to the effect of “You know enough about my company already; you write the email.”

And my dumbass, fearing to offend, would go out of my way to write intros for strangers who didn’t even bother to write anything themselves. So, I’d send that email to a friend or colleague in the industry. “You interested?” along with the email they sent me. And if they didn’t, just their LinkedIn, website, and/or deck.

Naturally, most would say no. Some would ask for my take on them. To which, I’d share that I didn’t know much about them outside of the obvious. I wasn’t investing myself, but they wanted to meet. 10-20% of the time, some friends and colleagues would say yes. (To this day, I wonder if it was just their policy to say yes to all warm intros or they were trying to be considerate of me. Some, over the years, I’ve asked. As such, it’s all the above.)

Over time, I would just include “I’m not investing. Only met them once.” in addition to “You interested?” in those emails.

Then one day, and I don’t remember when I first thought to myself, why the hell am I putting my reputation on the line each time for someone I don’t know and personally haven’t bothered to dig deeper only to write an email to show I also didn’t care about them? Why would I put myself through that? It had also become emotionally taxing to me to go through all those actions only to disappoint the founders (and myself) 99% of the time. Not only would I feel bad (often delayed disappointment and resent at myself), but I also wasn’t doing anyone any good.

So I stopped. Full stop. Period.

Around the early innings of the pandemic when it felt like there was a greater influx of deals and noise.

My rule became, and still is, unless:

  • I’m investing/invested
  • I’m advising (investing my time)
  • I’ve worked with you before and I would instantly jump at the chance to work together again
  • I’ve hired you
  • I’ve known you for so long and to a level we’ve become good friends and I feel like you’re a good reflection of the people I choose to surround myself with (that does not mean you have to be successful, but that you need to have good values and the discipline to pursue them)
  • You are someone I care about
  • Or someone, that has wowed me in a fundamental way.

AND I know the other person who you want an intro to well enough…

I’m not writing any intros.

I still read every email I get. Cold or not. And I still respond to every warm email I get. But for my fragile heart that can’t stand disappointing more people and the volume of emails I get, I’m not responding to any emails that look like they’re templated, AI-generated, or written without care. So I can focus on the ones that matter.

Photo by Collins Lesulie 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!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

Vacation Responders

vacation, beach

I started this practice back in 2019, inspired by two legendary people, but also that vacation responders are so boring. Why? If I’m going to take time off to have fun, why not make my out of office response fun to read as well. And so I followed through. Every vacation responder I’ve had since has always been… different.

The more I did so, the quirkier they got. And I found it as a fun creative writing exercise too. I took it so far to the point that of the many different email addresses I’ve been lucky enough to have over the years, I almost got “fired” because of my vacation responder through that email address. “You don’t seem to take your job seriously.” I do. In fact more seriously than most I’m led to believe. And I love what I do. Every career choice I’ve made I’ve made with the intention of serving the people I do serve with the utmost respect. Customers. LPs. Investors. And so on. But doesn’t mean I can’t have fun. I don’t take myself seriously, but I do take my job.

Then recently, having just gotten back from a break, a friend asked why I don’t share my vacation responders publicly as potentially inspiration for others to write interesting vacation responders. And I thought, why not?

I don’t plan to start a movement here. This may just be me and my own weird sense of fun and what makes me giggle. But in case it might offer you a little giggle as well if you haven’t emailed me when I’ve been out, sharing my last three vacation responders below.

The date is [date redacted]. I’ve just been told that I won the government lottery to be shot light years into space to find answers – to go to the largest moon of the planet Polyphemus,ย Pandora. Nervous, but ready, I’m jotting this in my diary before I go into cryo.

[NEW ENTRY]

The date is [date redacted]. I’ve just awoken from the best slumber I’ve had in a long time. Only to be interrupted by this rude guy called Miles Quaritch. Apparently, I’m only allowed to address him as Colonel. He looks like the person Colonel Sanders would be if he did P90X instead of fried chicken.

I’ll be updating this diary periodically before I one day return back to planet Earth.

[UPDATED NOTE]

Training is tough. Got the lights knocked out of myself a few times. Now sitting with a black eye as I’m recording this entry.

[UPDATE 2]

Food is odd but good. Still learning when to use utensils and when not to. Seems like the general answer is to not to.

[UPDATE 3]

Ahhhhhh, they found us-…

[UPDATE 4]

Hell has broken loose!!

[UPDATE 5]

All is quiet on the western front.

[UPDATE 6]

Ahhhhh-…!

[UPDATE 7]

I’m alive.

[END TRANSMISSION]

I know Iโ€™m supposed to say I wonโ€™t be able to respond until I get back on [date redacted], but the truth is Iโ€™ll be lying out of my ass. In always having my phone with me, I will more likely than not see a notification blip pop up on my phone lock screen, assuming I still have service onย Pandora. And I know that from time to time, I will need to interrupt my vacation to answer something urgent.

That said, I promised myself Iโ€™d unplug and enjoy my life as one of the Sky People as best as I can. So, Iโ€™m going to run an experiment. Iโ€™m going to let you decide:

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

Escaping into chaos,

David

So….. I just watched Shogun. A phenomenal show. 11/10 would recommend.

Loved it so much I created a time machine. You didn’t just scoff at me, did you? Who are you to say that I can’t invent one? We have robots, quantum chemistry, DNA cloning, generative AI. Of course I can make a time machine.

Not to reveal my hand too much here, since I’m not sure the world is ready to accept a time machine yet, but an EKG’s ability to monitor micro-pulses and a quantum computer that can perform quantum calculations based on limited historical datasets can do wonders.

Anyway, by [date redacted], I will have been whisked away into the historic lands of Japan. Unfortunately, I will have very little reception as Starlink will have yet to exist in 17th century Japan. I hope to come back well-versed in tea ceremonies, bladesmithing, and with the honor of being a shokunin in a craft. On the off chance I get caught in the feudal wars between rising warlords, I’ve designed a failsafe that will pull me back into the 21st century on December 2nd, hopefully with all my four limbs attached.

I know Iโ€™m supposed to say I wonโ€™t be able to respond until I get back on [date redacted], but the truth is Iโ€™ll be lying out of my ass. In always having my phone with me, I will more likely than not see a notification blip pop up on my phone lock screen, assuming I still have service in historic Japan, which is possible since I’m using the neuromodulator in the time machine as the connection point to connect to 2024’s technology. And I know that from time to time, I will need to interrupt my vacation to answer something urgent.

That said, I promised myself and my partner Iโ€™d unplug and enjoy my time off as best as I can. So, Iโ€™m going to run an experiment. Iโ€™m going to let you decide:

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

Cheerios and orange juice,

David-san

I am told by my outie that he will be going away for period of time. And as I have gone through the severance procedure, as your humble innie, I will be unable to get back to you within that time. Not because I don’t want to, but I just won’t be awake then.

My outie has been quite stressed, but in the wellness room, they tell me he is loved and he has friends, and for these next few weeks, he’s spending time with people who love him.

I know Iโ€™m supposed to say I wonโ€™t be able to respond until I get back on [date redacted], but the truth is Iโ€™ll be lying out of my ass. In my outie always having his phone with him, our only mutual access point from the outside, he will more likely than not see a notification blip pop up on his phone lock screen, assuming we find a way to reconnect our innies on the outside, which should be possible as we have a master plan in place and an all-access card to make our innies’ voices heard. And I know that from time to time, I will need to interrupt my vacation to answer something urgent.

That said, I promised myself and my partner Iโ€™d unplug and enjoy my time off as best as I can. So, Iโ€™m going to run an experiment. Iโ€™m going to let you decide:

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

Innie out,

David

Photo by Upgraded Points 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!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

On Writing

writing, journal

I’m not a good writer.

As a kid, I wrote poetry because it was easier to express myself in short form than long form. I also used to start writing fictional books, but stop after chapter one because I didn’t know how the story would develop. I was also the kid who would find five different ways to say the same thing in grade school, just so that my essay would hit the page limit. Yet still, my lowest grades among any subject was still English, particularly writing.

David Ogilvy, the namesake for the legendary advertising firm, Ogilvy & Mather, now just Ogilvy, once said: “Woolly minded people write woolly memos, woolly letters and woolly speeches.” The truth is I was, probably still am, a “wooly minded person.” But I try to be better.

That was the genesis of this blog. I didn’t have grand hopes of becoming famous. Or that I was going to make a career out of this. Still so, as it is still the reason why I haven’t said yes to any sponsors to this blog.

I write to think. I write whatever comes to mind. Simply, I write what I want. In fact, when the fact I have this blog comes up in conversation, I still actively tell me to unsubscribe. This isn’t an LP blog. Nor a VC blog. Nor a startup blog. It’s just my train of consciousness. Something I commit to every week. So, I’m extraordinarily honored to have a few thousand of you read this on a regular basis.

Thank you.

I don’t say that enough on this blog. But to all of you reading, I am deeply grateful you’re on this journey with me.

But… over the years, people have said I’m not as bad as I say I am at writing. Which might be true. We are all, after all, our own harshest critics. While I’m nowhere near the level of David Ogilvy or Brandon Sanderson or Maria Popova or Neil Gaiman or Susan Cain, in case it might be helpful, here are the gentle reminders I give myself when it comes to writing:

  1. Write as I talk. Incomplete sentences. One word sentences. Short, easy words occasionally sprinkled in with a $10 word I like. Tenacious. Idiosyncratic. Judicious. And yes, I’m conscious that I use ‘bandwidth’ instead of ‘time.’
  2. Write only when I’m inspired to. I don’t have a strict regimen of writing. I’ve met authors who have four-hour morning writing routines. I don’t. This is not my full-time job. But I enjoy writing. And I’m not publishing daily. I’ve committed to weekly. That affords me an immense amount of latitude for ‘productive time to be bored.’ I’m more often inspired by ‘touching grass’ as the kids call it than I am staring at my monitor or journal.
  3. In case I’m on a deadline and I’ve been uninspired up till the deadline, I have a very specific doc I reference. The metaphorical ‘break glass in case of emergency.’ It’s called the Emotion Catalogue. In it, I’ve tracked every single time I’ve consumed a piece of information that led to a specific emotional reaction. Happiness/joy. Sadness. Regret. Guilt. Jealousy. Anger. Inspiration. Fear. Creativity. Not sure if the last one is an emotion, but to me, it is. And if I’m supposed to write about a certain emotion, I need to feel that emotion. So I go to that catalogue, pick one or two of the inspirations within a section. And I consume it. Read it. Watch it. Listen to it.
  4. Use productive time to edit. Use inspired time to write. For me, that’s usually (not always) writing in the evening. And editing in the morning.
  5. I ‘idea-journal’ every day. If I can’t think of a new idea to write on, the journaling prompt I have to answer, “What is the most important question I should be asking myself today?” or “What did I really not want to do today? Why?”
  6. Write for one person. You. Or for me, the person I was yesterday. I am always guaranteed one happy reader. But also, if it’s helpful for me, there’s a good chance I’m not alone. And it’s helpful for someone else out there as well.
  7. Rewrite things often. The first idea is usually not the best, nor is it the most refined. Even if it’s five years from now.
  8. Be comfortable with dropping ideas. Sometimes I’m motivated to write something, but I lose motivation halfway through. Instead of making it homework for myself, it’s easier to mentally drop it. This is different from ideas I’m still motivated to write about, but can’t find the right concepts or words to put it into play. Those I mull over for a while. Sometimes, years.

Photo by Yannick Pulver 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!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

My Advice is Better than Your Advice

clown, stormtroopers, different

One of my favorite Hunter Walk lines, and one I cite quite often is: โ€œNever follow your investorโ€™s advice and you might fail. Always follow your investorโ€™s advice and youโ€™ll definitely fail.โ€

Investors are more likely to drive a company to the ground than otherwise. Founders listen to the advice of people they deem to be more senior and more experienced than them, as if they were written into the Bible. The cold, hard truth for people who give advice is that:

  1. Not all advice is created equal and most advice is situational.
  2. Your advice is more likely to be useless than useful in the aggregate supply of advice.

Advice should always be taken with a grain of salt. And oftentimes, certain pieces of advice is overweighted given the brand of the person giving it (who is right vs. what is right) and/or given the number of times the advice is given.

I’m lucky enough to be asked to be an advisor to a small number of funds, startups, and non-profits. Nothing to ever be worth bragging about. In fact, sometimes I wonder why I have a seat at the table. Nevertheless, lucky to share a drink with people smarter than me. I also realize that I’m a work in progress, and love to learn, just for the sake of learning. I’m not the famous person in the room, nor am I the most experienced person in the room.

So…

  1. I always preface my advice with “Take this with a grain of salt, and this is purely my opinion – one among many others. I trust you to make the final judgment call of what makes the most sense.”
  2. I give the unorthodox opinion. If I don’t have one, I don’t share any advice. I will caveat that I play in the early stages of company formation, when organizations are more so the pirates than the navy. When things are non-obvious, and need to fight to have a seat at the table. And given that the company and/or fund’s job is to question the status quo, I believe it is my job is to enable the founders to consider unorthodox paths. The minimum I can do is suggest that even if my advice is wrong, there are more paths than the one or two options we have in front of us. Or as Mike Maples writes in his book Pattern Breakers, “breakthroughs require pattern breaking.”

All in all, is my advice better than yours? Or anyone else’s? Who knows? But at least it’s different.

Photo by Mulyadi 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!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

Happiness

I had a number of people ask me what I’m doing next. So I told them.

One of the key pillars of what I am doing now is content. It’s why I write this blog. It’s why I produce Superclusters. It’s why there are a few new projects I’m working on that will shed light to this opaque world in which we’re in. Particularly in venture. In the allocator world.

I don’t hold anything back. There are no other cards I’m hiding up my sleeve. When a friend, an acquaintance, a stranger ask me how I do something, I tell them. Unfiltered. Without restraint. Without reservation. Without hesitation.

And for some reason, recently I’ve had more people ask me why. “What’s in it for you?” “What’s your master plan?” “Do you make more money this way?” “Why not just do X?” “You know you can get people to pay you a lot of money for this.” “Aren’t you afraid of being obsolete?”

Some questions come from a place of fear. Others, a place of greed. None of it from a place of joy.

There’s nothing in it for me, except for one thing. If I can help one more person not fall through the pitfalls I went through, or help one more person live a more meaningful life, or help one more person smile, I’d do it in a heartbeat.

There’s a great line I remember watching in the show After Life. “Happiness is amazing. Itโ€™s so amazing it doesnโ€™t matter if itโ€™s yours or not. A society grows great when old men plant trees the shade of which they know they will never sit in.”

I just want a better world. I want to make people happy. And I donโ€™t care if itโ€™s my own. But making another person truly happy makes me happy.

Whether you believe me or not, that’s up to you. But that’s all I have to say.


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!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.