I was chatting with a friend over the weekend who made me look stupid.
We were catching up after a while and we were talking about career paths and opportunities, and I had shared that I was offered to join a few large institutions late last year and earlier this year. Both of which I eventually turned down. And that one of the canonizing questions I had in the back of my head among 2-3 others was: When I leave, could I say I was successful because of the institution or in spite of the institution?
And for the first time, after sharing that set of questions with a few friends when I was in the process of making a decision, someone called me out. “That’s a bad question. That’s a horrible question.”
He goes on, “The question presumes that you are either joining a has-been or never-was institution OR that you couldn’t do anything meaningful while you were there. Given the names you’ve told me, the former is most likely not true. Instead, the framing of the question should be:
“What can you do at this institution that no one else with that job title has done?
“Something you actually wrote about before. On top of that, what can you do at this institution that no other institution would allow you to do? And how can you leverage the hell out of that? Why would you even join an institution where you can’t even leverage their success to date? That would make you look dumb for joining a bad institution when you have the opportunity to join a great one.”
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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.
A conversation with an LP reminded me of this recently. Can we trust a GP’s word that they’re a good picker if they can’t assess how likely an LP is to commit?
I’ve had multiple conversations with GPs where they tell me XXX and YYY are excited to come in the fund, and they just need more time to close their fundraise or for their process. Then the same XXX and YYY LPs ghost these GPs for months on end. For me, that’s enough for me to question their level of commitment, but not having been in those conversations firsthand, I can’t speak to the actual incentives. Sometimes, I actually know XXX and YYY LPs well enough to pick up the phone and dial them right away and ask them what’s up. Which I do. Only to hear from them and they say they had passed already.
Now I don’t know what actually goes on between those two parties. What’s said and what’s not said. There are many LPs out there who give very soft “no’s.” In hopes to not offend, they imply it’s a “no.” There are also LPs who explicitly say it’s a “yes” ONLY IF ZZZ happens. Given the current market, most of the time, ZZZ doesn’t happen, which becomes an easy out for the LP. The LP’s felt like they’ve delivered the “no.” The GP is still hanging onto the hope the LP likes them enough to break the rule. And then, there are many GPs who have selective hearing loss.
Nevertheless, there are multiple instances of this. And it’s not my job to point fingers to any party other than elucidate that this exists in our world.
That said, even if an LP doesn’t explicitly say “no”, there should be enough breadcrumbs to point to whether someone is a pass. Probably harder to know if they’re a “yes.” But there’s definitely writing on the walls if it’s a pass. And it’s almost always better to assume an LP is an out than an in if there’s hesitation.
The outstanding question for someone like me or any of my friends who I’ve had this conversation with is… is this indicative of a GP’s EQ when talking to founders? Is this GP more prone to rewriting history and facts? Is there a massive perception bias here and is the GP living through rose-tinted lens?
Richard Feynman has this great line. “The first principle is that you must not fool yourself — and you are the easiest person to fool.”
And I’ve also had this conversation with another GPs a few weeks back, and I said, “You’re either lying to me or you’re lying to yourself. One is worse than the other. But neither gives me a reason to back you.”
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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.
“When small men begin to cast big shadows, it means the sun is about to set.” — Lin Yutang
It’s been 10 years since I first stepped into venture. Yet still, while I know more, have met more people, and have experienced more, and when I look back, I pity the knowledge and experience I had a decade prior… yet despite all that, I know I have still so much work to do.
This essay was born from many conversations over the years, but especially so, in the past few months, where I’ve witnessed conversation after conversation that follows the theme of:
“Have you met X?”
“I have.”
“What do you think of X?”
“X feels far smarter online than X is in reality. After meeting X, where I anticipated so much, I was only let down.”
Never meet your heroes, they say.
In venture, we live in a world where the average VC brags more about “being a part of the journey” or “excited to support” a founder they backed than actually doing the work. It’s no wonder that 70% of VCs add no value (though 15% more add “negative value”). But it is far easier to say the part, look the part, than do the part. With SpaceX and OpenAI’s IPO today, Anthropic’s tomorrow, and Databricks, Anduril, who knows what, the day after, we will find many more VCs congratulating themselves, raising larger vehicles, and casting larger shadows.
In an unreleased interview with a GP I really admire, she told me an anecdote of a founder she knows well. “All of my early stage investors made out like bandits with my huge exit, and I never got a thank you. All I saw was them talk about how they discovered me and how they had such a big role to play in my success. But no one said, thank you for returning my fund 10 times over. And here’s a token of appreciation, whatever the appreciation is.” Which echoes the growing sentiment in the ecosystem.
And here’s my own self-reflection.
I hope that I cast no greater of a shadow than my beliefs, thoughts, and remarks would allow. And I hope still that I have the humility to cast a smaller shadow than I would ever be allowed to.
People measure shadows by the potential and impact someone may have. I have a friend who turned 30 recently. And when we sat down to chat, he told me that people were no longer telling him that he has potential. And one of his greatest fears is that people only see the person he is today for who he is today, and no longer the person he will be tomorrow. That pressure, more than anything, meant he was no longer “young.” I don’t think anyone ever loses their potential as a function of age. I have friends double my age, still learning every day, faster and more studious than people half of theirs. To me, that is still potential.
And here I hope that the shadow I’m capable of casting is underestimated than overestimated. But at least to myself, I hope I never underestimate myself.
“After I’m dead, I would much rather have men ask why I have no monument than why I have one.” — Cato
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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.
I wrote this piece last year on how I’ve evolved my thinking on intros. And while not my most popular post by a long margin, it is something I do forward to others who ask for intros.
Now, despite that, people still ask for intros. And so at the risk of sounding like an a-hole, I’m going to say something that may offend a lot of people who know me.
Just because you make an intro between someone and me doesn’t mean I will automatically make an intro for you.
Few things to clarify:
1/ First off, I’m genuinely grateful for all intros. Whether it’s to someone you’ve known for a long time, or someone you just met yesterday, or someone you deeply respect, I’m honored that someone else is thinking of me when the intros are made. I will never take that for granted.
2/ I get the “you scratch my back, I scratch yours” mentality. But:
Not all intros are created equal. Not all relationships are created equal. Introing me to someone you met yesterday does not give you the equivalent political capital for me to intro you to someone who, whether I know them well or not, is someone most people seek to meet. Just because a friend made an intro between a stranger they met at the bar last night doesn’t mean they’re allowed to ask an intro to your sister to date her. Obviously, I’m exaggerating a bit, but I wanted to drive the point home.
People are not commodities. I don’t trade people like I trade my stocks. I will naturally make an intro if I know both parties are looking for each other, or at least topics, skillsets, or experiences that the other party has.
If you make a great intro, I will of course: (a) Report back to you and thank you for the intro. (b) Find other ways to thank you beyond words.
The whole reason I’m writing this post in the first place is that a few bad eggs recently spoiled the entire carton. I had a few exchanges recently where certain individuals felt justified to ask for, and hell, take it a step further and demand, intros to certain reputable individuals I know because they made “that intro for you last year.” Which I admittedly felt it wasn’t worth continuing the conversation with the person they made an intro to within 15 minutes of our chat.
Most of you are not the above character. I get it. But I also felt the need to get the above off my chest and use it as a future artifact when the situation arises again.
Thanks for reading my ramble. Truly.
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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.
When I first started journaling again after years of not doing so (If you’re reading this, thank you, Professor Kellogg), I did so with pen and paper. Mostly due to an exercise Professor Kellogg had us do by finding comfort in the mistakes you make along the way. That that too is art. Is expression. Is personality. Most of my classmates eventually regressed back to pencil for notetaking or digital devices, but it is a practice that has stuck with me even till today.
When I first started dating my now girlfriend, she noticed me writing in ink. Every so often, I’d mess up and just strike through the words that were misplaced in my notes. She’d ask me why I didn’t write with a pencil. To which, I told her what Professor Kellogg told me and that over time, it became a habit. It made me write more intentionally. Also, I will note that ink looks better on paper than graphite does. At least when it comes to writing. High contrast, you know.
I grew up at the tail end of the Kodak and camera roll. I remember a time when every picture had to be taken with intention. With purpose. The framing had to be right. The lighting had to be perfect. The eyes had to stay open on flash. We now live in a world where digitial hoarding has become really, really easy. Google’s got me good, making m pay more and more as I somehow never delete emails anymore, only archiving them. One of my good friends has over 35,000 photos on her iCloud, and hasn’t deleted a single one since the first one was taken. Still a crazy number to me.
At the same time, the ephemera of the internet makes things easy to forget. Easy to erase. Public and private mistakes are erased as if there’s no digital footprint in the first place. Nearly every messaging platform allows you to delete a DM you send. I say “nearly” since I haven’t tried every single one out there. But it’s most likely, all. Snap was born on the idea of erasure, something many other platforms have inherited. Any post, tweet, or website can be erased. Many assume that you write in pencil, but forget even after rubber absorbs the graphite into its folds, the indelible imprint still exists. Watch any spy moie where they smear more graphite over an erased string of words to reveal the negative spacing of the letters that were, if you don’t believe me.
So, for those who share their voice in whatever capacity on the digital world, never forget the echo. The web archives exist. “This message has been deleted” exists. Local downloads exist. Witnesses exist. Screenshots exist. Granola exists.
As our civilization gets closer to a world that never forgets, what more can we do?
What less should we do?
Just a gentle reminder that we all write with pen on paper.
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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.
Recently, I spent some time with friends where we ended up talking about career growth. One of whom was at a standstill of which opportunities to pursue if at all. But another of whom offered advice through a pair of interesting lens. One I felt interesting enough to reshare.
When you pursue a new opportunity, especially one where you have strong agency and potential autonomy to influence business outcomes, there are three possible outcomes during the duration of your role.
Success
Failure
And not succeeding
Do note that failure and not succeeding are not the same thing. Failure is when you aim for something and it ends in a negative outcome. Not succeeding is after doing all you that you do, the outcome is still, give or take, the status quo. You haven’t moved the needle for the better or the worse.
At a smaller company, failure is oftentimes business closure. Not succeeding is either a small outcome or the evolution of a fast-growing startup to a lifestyle business with no noticeable impact on the industry. For an ambitious individual, being forgettable is arguably worse than failing. And naturally worse than succeeding. To be forgettable means it takes an extra 2-3 years to rebuild the reputational capital up before you have the trust to pursue your next ambitious outcome.
At a larger organization, failure is actually pretty hard. It could be the closure of a department, a re-organization, and very rarely, a negative inflection point for the business. More often than not, it’s not succeeding, which is just maintaining the status quo. Naturally, success is good regardless of organization size.
Failures are seen more charitably at smaller organizations. Larger organizations magnify the echo chamber and press. But in both worlds, they’re seen as your mark on the world. Evidence that you’ve tried. Not succeeding, on the other hand, is often worse at large organizations. Why? Because your career stalls. The more ambitious you are, the worse your career stalling will impact your career. The longer you stall, the harder it is to earn back the momentum. So unfortunately, the worst outcome an ambitious individual can get is not succeeding at a large organization. Death by a thousand cuts.
And the unfortunate truth is that large organizations have a lot of inertia. “Strategy tax” in the words of Bret Taylor. Or as a very senior allocator who recently left their large organization told me: “Some of these layers (at institutions) are there to sap the courage out of your investment decisions.” And you can easily delete the word “investment” out of that sentence.
If you fail or not succeed (not bad, not good), the liability of it not working is put on you the larger the organization. So you take on the tax, burden, career stall if the bad outcomes happen. If you fail at a smaller institution, no one blames you because you took a risk and tried your best and things didn’t work out, they blame the institution.
6/18/2026 Edit: Not succeeding is to be forgettable.
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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.
October last year, I was having dinner with an aspiring GP who, for whatever reason, thought I should do more advisory work. A comment made after I shared that I do very little advisory work. So she asked why.
And I said something to the effect of: My goal in life is to spend time with the most curious, the most ambitious, and the highest performing individuals. In the early days, when advisory is opportunistic and assuming you don’t need the capital, you can choose to work with some incredible people. Over time, as you build a sustainable business, and as this becomes your primary source of income, to pay the bills, you may end up working with folks that you may not have chosen to work if you had the choice. You end of building a fantasy portfolio of, in my case, GPs, that you’ve allocated your time to. The one resource you can never get back. And because I’m someone who likes optimizing different parts of my life, I may very well fall victim to my own optimization of being an advisor. I would rather not see myself inevitably choosing those circumstances. What scares me is not the work but the person I will end up becoming.
Just earlier this week, I had another conversation around the same topic with a GP I deeply respect and have chosen to work with. So I thought it seems to be time I share this publicly.
Many of my contemporaries have built robust businesses for themselves being advisors to GPs and LPs. And I think it’s a beautiful thing. The world needs more great advisors. We always seemed to be starved of them. The world needs more people who are willing to pay it forward. To share their lived experiences with those who have yet to live. But I don’t think I could ever do what they do.
To me, this blog and my podcast are what I need as outlets to help the world. Two things that will always stay free. Although for my podcast, many a time I have resisted the temptation to create a paid product to keep the podcast’s lights on. I hope good and useful knowledge continues to stay that way. Free. Through that, the frameworks and lessons I’ve come across and/or use.
But the reason I don’t think I could ever do what some of my advisor friends do is because I think a lot about optimization. And in the theme of optimization, I will take more opportunities than I would like. But I’m also really bad at breaking up. And so to not put myself in that situation, it is better to not begin.
Have I advised folks? Yes. Will I continue to? Probably. Opportunistically. Will I still say no to most advisory opportunities even if there is money to be made? Yes.
Does that mean I build an advisory practice? No.
If you’ve been a long-time reader of this blog, you’ll know I’m a deeply flawed individual. I don’t claim to be perfect. And I’m definitely not a profit maximalist. Although I do wonder what kind of person my alter ego would be. But there are a specific set of choices that I believe I can make so that I live my most fulfilling life. And one of those choices is choosing the people I get to spend time with. So if I were to do any advisory, it’d only be with people I deeply respect AND can learn something from them as much as they from me.
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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.
“‘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 many—colleagues, LPs, founders, even her friends—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.)
2025’s Most Popular
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 to—still do—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:
Hustle as a Differentiator — 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.
If 198 Pieces of Unsolicited, (Possibly) Ungooglable Advice for Founders Were Not Enough — 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.
Dear LP — 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.
Good Misses and Bad Hits — 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.
Dear Emerging Manager — 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.
Goldilocks and the 3 Secondaries — 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.
All-Time Most Popular
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.
The Science of Selling – Early DPI Benchmarks — Honestly, it still surprises me that this is my most popular one to date. Not because I think it’s a bad topic—in fact, I truly believe it’s a much needed discussion as venture funds face liquidity crunches and the asset class institutionalizes—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.
The Non-Obvious Emerging LP Playbook — 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.
10 Letters of Thanks to 10 People who Changed my Life — 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.
Hustle as a Differentiator — Only a matter of time that this one beat out the one I wrote about how to host fireside chats. 🙂
2025’s Most Memorable
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 — 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 — 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 Emerging Manager — Same as the above. Free therapy for myself. Hopefully helpful to the world.
The Question Off — 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 — 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 — 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 — 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 Backing Emerging VCs — One of the beauties of collaborating with someone brilliant—I’m looking at you, Ben—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 — 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 — 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.
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.
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 Fortune’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 BBC’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 Musk’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.
[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
I’m intentionally keeping this section void of the things that I said since I hate the idea of quoting myself.
“Part of the point of this [investing job] is that you want to be anonymously, asymmetrically correct. And you can’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 they’ve backed.” — Allie Garfinkle
“If it eventually doesn’t become consensus, you were wrong.” — Allie Garfinkle
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.
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 flow—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 — I get to ask dumb questions to smart people, refine my diligence skillset, get better at asking questions, and so on — 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.
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.
