questions - Cup of Zhou

April 20, 2026April 20, 2026

“I Write-Off Every Sourcing Slide” | Alex Felman | Superclusters | S7E2

“The game you play as you’re building a reputation becomes a different game than when you have a reputation. And I tend to find, from an LP’s perspective, when you’re building reputation, that’s actually when you deliver the most value.” — Alex Felman

Alex Felman is an entrepreneurial and family office professional. For over 10 years, as a second-generation member, he has run his own family office, Felman Family Office, and works with family offices around the world through his family’s multifamily group, MSF Capital Advisors. Using his expertise in Molecular Toxicology and Bio-entrepreneurship (B.A from University of California -Berkeley, MBA from Copenhagen Business School), he advises them in biotechnology, healthcare, and other futuristic tech industries with the goal of maintaining long-term wealth through innovation. He regularly speaks at family office and private wealth events on topics such as tech investment, manager selection, generation and succession issues, rising generation trends, and more.

He has used his experience within the family office industry and 20 year background as an educator to create Exponential U, a family office education program designed to help families become multigenerationally sustainable. His proprietary L³ framework (Learn, Leverage, Legacy) allows the holistic development of family members to ensure a smooth leadership transition.

You can find Alex on his socials here:
LinkedIn: https://www.linkedin.com/in/alexwfelman/

Listen to the episode on Apple Podcasts and Spotify. You can also watch the episode on YouTube here.

OUTLINE:

[00:00] Intro
[04:36] The ‘tastemaker’ for family offices
[05:54] Exploration vs discipline
[08:15] The hero’s journey in investing
[09:49] The life line
[13:39] Building and having reputation
[16:06] Risk appetites for asset owners & allocators
[18:44] Why won’t an institution invest in me?
[19:50] The quiet thing LPs don’t talk about
[25:15] When did Alex get involved with his family office?
[29:09] Writing off sourcing slides
[35:33] Different flavors of “sourcing from YC”
[38:41] Emerging GPs are “investments-as-a-service”
[40:08] Fund power law is greater than startups’
[43:44] Emotional value of investing in funds
[44:45] Most VC funds are scams!
[50:01] Optimistic cynic
[51:43] Reminders today about the good ol’ days
[54:17] Late stage capitalism
[59:10] Post-credit scene: Dave Chappelle and podcasts

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Every great conversation dances on the line of your understanding. You dance between both sides of the line and try to find out where what you know and what they know intersect and end. Good conversation is like play.” — Alex Felman

“With my background from the family offices, I almost believe that most family offices moving forward will need their own personal tastemaker or sommelier. Someone who’s curating the world specifically for the needs of that family.” — Alex Felman

“People get into trouble when they’re using the wrong tool or trying to do something for a different purpose. For example, I’m going to try to do discovery when I’m in my routine. Ok, you’re probably running into problems. Or routinizing my discovery. Those two things are in conflict with each other.” — Alex Felman

“One of the things people always forget—… What they remember from the hero’s journey is adventure, and we fight the dragon, and we get the treasure. But at the end of the hero’s journey, you’re supposed to bring that back to your community. And you’re supposed to forward it to your community. And you’re supposed to make your community better from the dragons and the treasure that you fight or find. Most people often leave off that last part. And I actually think that last part is extremely important.” — Alex Felman

“If you have a family office where you’ve actually outsourced it, your employee is more of an allocator than an owner. And in that case, that allocator is often making decisions to save their own job. Or to ensure that they continue to have a job.” — Alex Felman

“What I find is slightly sad is that ultimately because of security and comfort reasons, things like people’s pensions which should be more secure, are actually, in my opinion, taking riskier bets. And bets that will lead to worse outcomes.” — Alex Felman

“I believe that the amount of due diligence you do doesn’t matter depending on the deal size. So let’s say they’re writing five $100 million checks compared to 100 $5 million checks, that is literally 20 times the amount of work. So even if they’ll get a better return on that 100 $5 [million checks], on a realistic level, it forces them to play certain types of games.” — Alex Felman

“With at least funds on a standard two and twenty, somewhere around $75-100 million fund size is where the incentives shift from being carry-oriented to management-fee oriented. Once you get larger than that, then it actually becomes more incentivized for the fund managers to build up their funds than the actual returns itself.” — Alex Felman

“I would argue that power laws apply even more to funds than to startups.” — Alex Felman

“The intersection of venture as a product or service meets venture as a job career. And there are a lot of fund managers who see venture as a job career and essentially want to use it as a way to get a paycheck. And because of that, they’re going to put out a fairly boilerplate fund.” — Alex Felman

“Many venture funds are basically scams. I believe it’s a scam if you knowingly sell something you know you can’t deliver on. And the dirty secret in venture is if you purely look at venture from a financial point of view, most fund managers know they cannot hit their targets and yet they still sell that promise anyway. And I think that starts to become kind of scammy.” — Alex Felman

If you somehow made it to the bottom of these show notes, I’m also trying a new experiment where I write my reactions to the episode on my second blog, Superclusters After Hours. For Alex’s episode, you can find my reactions here.

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.

April 17, 2026April 17, 2026

(Not) Relationship Advice

Earlier this year, when catching up with a friend and talking about love, he shared his greatest relationship advice. “You want to marry someone who believes the world happens because of them, not to them.” And it really stuck with me. Both he and I are people who have big dreams. That in order to make our dreams happen we need every oar rowing in the same direction. That includes the people we surround ourselves with. More than anyone else, our romantic partner is likely the one we spend the MOST time with. But that in itself is a slight digression.

In a somewhat parallel sequence of events, at the end of last year, I had the opportunity to join a much, much larger shop. And while I ended up choosing not to join, the primary question I was asking myself was: If I were successful here, would I be successful in spite or because of the institution? The truth was from an outsider’s perspective, maybe even personally, it’d be really hard to tell.

Now why do I share the above? And where the hell am I going with all of this? What does love have to do with career opportunities?

So… this won’t be my most graceful transition between thoughts, but in my head, they all orbit the same genre.

One of the questions I used to ask LPs during my time in investor relations was: “What was the last investment you made that didn’t work out? Without naming names, what happened?”

And there are two reasons I ask that:

Oftentimes, knowing what an LP doesn’t or won’t ever invest in again is more telling than asking them what they do invest in. LPs are, by definition, generalist. And under that premise, they technically invest in “everything,” so you’ll end up getting very broad answers, especially if they cover more than one asset class.
Do they describe an investment that didn’t work out with active or passive verbs? Did it happen to them? Or do they own up/exhibit agency over their own decisions? Are they arbiters of their own destiny? “I made this investment decision, learned, and this is what I won’t do in the future. Or will still continue to do.” is different from… “This mishap happened to me. How could I have known? It is what it is. It’s not my fault. It was out of my control. It was someone else’s decision.”

For the latter point, people who don’t seem to be able to own up to the decision will likely not be your greatest champions if you’re an emerging manager. If at all. To them, life happens to them. They can’t control it. They have a narrative they keep telling themselves that they have no power. Some might be true. But these folks rarely stick their neck out for you.

By default, most emerging managers look less than pretty. A million reasons (most of which likely true) of what could go wrong. And it’s actually in the best interest of a capital allocator’s career and income that they stick their neck out for risky bets. Many institutions don’t compensate their team based on outlier performance. So incentives won’t be aligned. But to borrow an adage of Jobs, “the people who are crazy enough to think they can change the world, are the ones who do.” And at the very minimum, they have to believe they can change their own world.

When things are non-obvious—from a returns perspective or strategy or anything else—you need people who can and will invest courageously and own that decision.

Photo by Everton Vila 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!

April 13, 2026April 13, 2026

“Venture is a Who Business, Not a What Business” | JD Montgomery | Superclusters | S7E1

“One thing that is unique to private equity and venture capital is persistence is a little easier because of the brand. ‘They did good deals, so therefore, the good deals come to find you.’ If you were in a long-only private equity shop or hedge fund, Amazon is not going to come find you because you invested in Shopify.” — JD Montgomery

JD Montgomery leads the Family Office division at Canterbury Consulting and is a seasoned advisor with nearly four decades of experience serving prominent families with a focus on strategy, organization and measurement. Based in Newport Beach, he serves a select group of multi-generational families and helps them navigate the complexities of wealth, purpose, and legacy. Mr. Montgomery partners with his clients to help them optimize the allocation of their resources across generations. Over the years, Mr. Montgomery has developed a deep network of relationships in the venture capital industry. He has helped his clients gain meaningful exposure to venture funds and direct investments and develop relationships with leading innovators and investors globally. He is a Managing Director, shareholder, and board member at Canterbury Consulting. He graduated from Stanford University and holds the Chartered Alternative Investment Analyst (CAIA) designation.

You can find JD on his socials here:

LinkedIn: ⁠https://www.linkedin.com/in/jd-montgomery-6161341b/⁠

Listen to the episode on Apple Podcasts and Spotify. You can also watch the episode on YouTube here.

OUTLINE:

[00:00] Intro
[02:18] The “some day” exercise
[11:12] Why does JD do “some day” every 6 months?
[12:33] JD’s life line
[16:44] When JD is 85 years old…
[18:05] JD’s relationship with fatherhood despite the trauma
[22:40] Annual dad report cards
[25:33] Intentionality with GPs
[28:41] How to avoid one-hit wonders
[33:43] How to transfer self-esteem
[36:05] How do you get GPs off of their talk track?
[37:36] Non-obvious things JD looks for in GPs
[41:43] Is selling 0.2X DPI in the first 4 years meaningful?
[44:27] Should you recycle capital or deploy out of the next fund?
[46:34] Why did JD choose to work with families?
[48:07] “Never eat alone”
[51:34] How does JD think about time allocation?
[55:06] How many new GPs does JD meet with?
[59:07] How did JD pass on then back Founders Fund?
[1:03:22] The difference between unexplored gold veins and rotting trash
[1:08:13] Mayan Mocha at Austin’s Picnik
[1:08:58] JD’s secret street taco recipe
[1:11:09] JD’s reminder that we’re still in the good ol’ days
[1:13:20] Post-credit scene: No garlic and onions

SELECT LINKS FROM THIS EPISODE:

Canterbury Consulting
Talal Attieh
Steel Atlas
Jalen Hurts
Stanford University
Chris Rock
Chris Rock’s Never Scared (which includes his “Keep Her Off the Pole” Routine)
“Come On Eileen”
Dexys Midnight Runners
Riverside
Miles Grimshaw
Garry Tan
Initialized Capital
American Express
Never Eat Alone by Keith Ferrazzi
Jenifer Moore
Fashion Island
Founders Fund
SpaceX
Scott Saslow
“How to Start a Single Family Office” with Scott Saslow (Superclusters)
Picnik
The Office
Mother Teresa
Salt Fat Acid Heat
Samin Nosrat
Hoja Santa / Mexican pepperleaf

SELECT QUOTES FROM THIS EPISODE:

“I don’t have a mentor per se. My mentor is hundreds, probably thousands of people—I’m sure thousands—people that I’ve met where I try to learn just the amazing talent that person has and I smush it with the next person that I meet that might be most kind person that I meet or the most organized. So it’s this blend of a lot of people that really becomes the mentor.” — JD Montgomery

“DOD – dear old dad.” — JD Montgomery

“Kids grow up like trees and saplings. And a sapling needs a guiding post to hold them up when it’s windy.” — JD Montgomery

“One of the other questions I will ask is: ‘Tell me about the hardest thing you’ve ever done in your life.” — JD Montgomery

“To whom much is given, much is expected.” — JD Montgomery

“In estate planning, you can transfer money, but you can’t transfer self-esteem. Self-esteem is gained by going through the school of hard knocks and doing things and relying on yourself.” — JD Montgomery

“If they’re passionate about something—if they want to leave the world just a little different—their ding in the universe—and they want to give back, money doesn’t ruin them.” — JD Montgomery quoting a North Carolina professor

“I am not in a ‘what’ business; I’m in a ‘who’ business.” — JD Montgomery

“Gross IRR; gross performance. I don’t care. I care about net. It’s okay to show gross and then net. I prefer net. But if you show gross only, it’s just gross.” — JD Montgomery

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!

April 10, 2026April 5, 2026

The Texture of a Thesis

Meriam-Webster defines texture as “the visual or tactile surface characteristics and appearance of something” or “the disposition or manner of union of the particles of a body or substance.”

A more interesting definition, at least on the tactile front, might be the resistance you feel when your skin brushes against a substance. The friction you feel. The subsequent expressions of rough or smooth follow the amount of friction you experience.

I was reading Scott Belsky’s latest blogpost. In which, he wrote the following:

“The more you remember, the more you will feel you have lived. I can’t vividly remember the details of more than a couple beach vacations, because they all blend together. But I vividly remember a night out in Tokyo at a tiny bar with my friend Joe, the first time I skinned up a mountain in Colorado, the longest run I ever took in the rolling hills of Tuscany, and getting lost in the streets of Kyoto with my daughter. The experiences I remember most are those that had texture — some sort of surprise or hardship that implanted them in my brain. These experiences create “core memories” that remain distinct and persistent, no technology required. My thesis on the future of humanity is that we will optimize for more of the experiences we’ll never forget. We will seek activities with texture to create memories that grip. And when we look back, the more of these textured memories we have, the longer we will feel we have lived.”

In a similar way, the ‘texture’ of life includes the moments we most struggled. And in the physical and metaphoric definition of ‘texture,’ leaves us scar tissue that protect our body from future similar experiences. It’s hard to recall the vivid details of life when it was all smooth sailing, but near impossible to forget our greatest character-building moments.

I’m a big believer that theses are the same. A product of our past experiences. And the restrictions we place on ourselves are a function of that. So regardless if an investment thesis is specialist or generalist, what I find more interesting are areas a GP chooses not to invest in, which include what they have never invested in, or have and will never again. Even more interestingly, assuming one only had the chance to interpret the “visual” nature of the thesis, what are the types of investments most people would think falls under a GP’s thesis, but a GP still will not invest in? The latter of which is the “tactile” nature of a thesis. The contact sport. That unless you interact directly with the GP, it is hard to tell.

Oftentimes, the GP may have more boundaries for themselves than we as LPs place on them. And that is always worth digging into.

The texture of the thesis.

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!

April 3, 2026April 3, 2026

Spiky, Lumpy, Smooth

A number of investors I’ve had conversations with recently used the word “spiky” to describe their investments and investment prospects. Both VCs who described founders that way and LPs who described GPs that way. With the latter, I want to caveat that these LPs were fund-of-funds and smaller family offices. The investment profile of a larger LP may look quite different given the incentives of the organization. But I digress.

What is “spiky?” Spiky, or ‘spikey’ (I’ll let you decide what your preferred spelling is), is an adjective used to describe someone who has a few traits that excel quite extremely. Not many, just a few. The implicit understanding is that sometimes they can be poorly proficient in many other areas. For example, you can be the world’s greatest AI researcher, but not know how to make scrambled eggs or cook at all for yourself. But in the areas where an individual is “spiky” in, they are in the world’s top 0.01% with very little other competition.

I’m also personally a big believer, that you really do have to be in at least the top 0.1% on something if you want to have a chance at top decile (10%) returns because by order of you needing to take on other responsibilities in a company and/or firm where you might not spike in those as much, your overall “spikiness” slips two decimal points. So, as an LP who aims for top decile minimum, I look for people who would be 1 in 1000. An a startup investor/VC, to bet on the 100Xers, the top 1% per say, you need to find people who have 1 in 10,000. Metaphorically speaking, the bar is higher since you’re less diversified compared to LPs.

So if that’s spiky, what is “lumpy?” You’re better than others in many areas. Potentially most areas. If 3.0 was the grade point average of your competition, you’re a 3.5 or 4.0. Numerically better, but you don’t particularly excel in any particular area. Or at least not in ways that make you an N of 1.

In emerging GP land, there are a lot of ‘lumpy’ people. Investors who are probably already in the top quartile, even top decile of the human population. To have the ambition, the track record, the network, and the wherewithal to start a fund requires a certain state of privilege, luck and effort that most can’t afford or have. They have just enough to be better, but not enough to be the best. These are, at least for me, the hardest people to say no to (assuming they’re good people). They’re people that I’ve described to other allocators (when they do diligence) as “good human beings” and “people I really enjoy hanging out with.” All true statements, by the way.

But even for spiky people, is their differentiator enough to create portfolio divergence? Sometimes, it doesn’t. Arguably, oftentimes, it doesn’t. Then the question becomes is their portfolio converging with others to a point where there’s still alpha? And for the (established) firms they’re converging with, (a) will they continue to converge (i.e. will the other firm(s) always want this investor around for their spikiness?), and (b) are the other (established) firm(s) best days ahead of them or behind them?

Expectedly so, you are now underwriting the other firm(s) as well.

I wish it were an easy judgment call, but it isn’t. And I’m likely to be wrong more often than I’m right. As most of us will be.

Then, there are people who are “smooth.” Some may call them generalists. Others may say well-rounded. And while both can be true, in a world of attention scarcity, whether in the mind of founders or co-investors or other LPs, you need to stand for something. And “smooth” people are easily forgotten. We don’t talk about them much because we forget about them.

Photo by Sierra NiCole Narvaeth 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!

March 19, 2026March 18, 2026

DGQ 26: Which Slide in my Deck Stood Out the Most?

One of my most used lines in my diction is: “Your mileage may vary.”

Maybe because of what I’ve written historically about. Maybe ’cause of my previous life in investor relations. Or maybe, it’s because of the interesting node I sit at in the venture ecosystem. I often get asked by GPs and founders alike for fundraising advice. Now before you come to any conclusions, I don’t have a silver bullet. I’m not even sure if my advice when it comes to fundraising is any good. While I’m lucky to have heard back from a number of people I’ve shared my thoughts with on the result of their fundraise after employing my “advice,” I’m still not completely sure how much of it was the fundraiser themselves and how much of it was the advice. And how much the color of the jersey matters.

And so when I share what I’ve seen or done, I always caveat with that first line. That said, what I think is more useful than any advice I could give pre-mortem is listening to the feedback of the market. The people you’re pitching to. When someone says no, why do they say no? When someone says yes, why do they say yes?

Inspired by a conversation I had the previous week at a summit, getting feedback from someone who passed is tough. Through the archives of fundraising, you’re more likely to get no’s than yes’s. And when you do, do you know why? Very rarely do you get much feedback. Investors (LPs and VCs) are either too busy or have too much to go through to give feedback as intimately as you probably like. And so I’ve always found it useful to make it easy for people to give feedback. Naturally, it’s never guaranteed you’ll get a response, but usually, the below question I like to ask reaches less deaf ears than “Can you give me feedback?”

I know you’re busy, and you simply don’t have the time to give every pass a share of feedback. But if I could ask for 30 seconds of your time (no more than that), which number slide on my deck did you most notice (good or bad)?

Or… was there a particular slide in my deck that piqued your interest the most that led you to schedule our initial meeting?

The goal of this question is to triangulate attention and mindshare. When you get the answer, then you can come to your own (hopefully intellectually honest) conclusion about whether the message shared on that slide is strong or weak. Controversial or not.

Moreover, you’re not overstaying your welcome. The advice and feedback you’re asking for in pointed and doesn’t consume a lot of time for the other party to answer (yet will feel to them as if they’re doing you a favor and/or being helpful).

Only once you know why people say no can you actually iterate on the pitch. Of course, there are many different ways to ask for feedback, and… your mileage may vary. Usual fundraising advice gets you through the first 10 pitch meetings. After that, you need to course-correct based on the feedback you get back.

One thing I will note is that in the age of agentic venture firms and tools that can be built within hours that cover every stretch of the imagination. One thing an LP told me that a GP told them was that some founders are getting smart. Preparing two decks for investors: one for the human eye, the other for the agentic audience. The latter with more appendices than the former. I imagine that it’s only a matter of time before VCs do the same to LPs as LPs are building agentic deck readers. In that sense, asking for deck feedback may not hold as much weight as it used to. Who knows?

Nevertheless, if there’s one takeaway from this blogpost, it’s that if you want help, if you want feedback, make it specific, low friction, and direct.

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

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!

March 11, 2026March 10, 2026

Revenue per Employee

I was reading Scott Belsky’s latest piece on the premium of originality and the metric of revenue per employee. Something I’d highly recommend you take five minutes to do so. While I do have my thoughts on originality in a time of AI, I’ll probably save that for another piece. For the purpose of this one, I’d love to spend it on the topic of talent in the current AI age.

I was co-hosting a retreat recently. The same one that produced this. Selfishly said, I think it was one of the highest insight per time spent retreats I’ve been apart of. And my friend who invests out of a multi-stage fund was sharing how talent became the new medium to evaluate an AI founding team. During diligence, for each engineer, “would OpenAI/Anthropic/Cursor pay $500K or $5M for this engineer?” Then you have an idea what’s the asset value from a talent perspective.

Similarly so, in a recent 20VC interview, Carles Reina, VP of Sales at ElevenLabs, shared that every sales hire must bring in sales equivalent to 20X their salary. So the more you pay a sales rep or account executive, the more revenue they have to bring in. Which leads me to Scott’s piece.

“A funny thing happens when the ROI (return on investment) of a person goes up: we start deploying MORE people — BUT only in ways that sustain or increase the ROI. Rather than larger organizations within a company, you’ll have MORE smaller organizations. My bet is that companies will deploy more people NOT to scale their existing products and services, but rather to launch new products and services.”

“If every hire makes “revenue per employee” either go up or down, how does that factor into headcount planning? Will we seek to hire more-entrepreneurial people who will come up with new products and services within the company? Will modern forms of compensation provide incentives for brazen agency, rewarding those who realize that they can just DO THINGS and own the outcome — from idea through execution?”

This again reminds me of the bundling-unbundling cycles with each wave of technology and/or business models. At the start, there are all these fragmented businesses solving niche use cases, but over time, as winners emerge, people want a one-stop shop for everything. Although this time, the one-stop shop could just be you yourself.

That’s probably also what makes my buddy Henry’s Lean AI Leaderboard so interesting. Bragging rights not to who has the most employees, but who has the greatest revenue per employee metric. The very definition of small but mighty.

Photo by Prabir Kashyap 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!

February 6, 2026February 6, 2026

Will AI Take Over LP Investing?

I recently watched Brandon Sanderson’s keynote on whether AI is art or not.

It’s a great talk. And I highly recommend you check it out even if you don’t work in the creative industries.

We’ve seen writer strikes in Hollywood as well as a proliferation of AI use cases in creative industries. James Cameron joined the board of Stability AI. The Russo brothers behind Marvel’s superhero sequel prowess have created their own AI studio. Pouya Shahbazian as well, using AI over the next four years to create 30 AI-generated films. The list goes on. As such, the question of “Is AI art?” is an interesting one to answer. And admittedly, harkens to a series of conversations I’ve had with allocators on leveraging AI in investing practices.

From the VC/GP side, there are folks like Yohei, Sarah, and Ben and Matt, just to name a few who’ve all been building and incorporating AI recently into their workflows and deal flow pipelines. Yes, I know I’m missing a lot more names. But you get the point. From the LP side, progress is still slower, but many younger LPs are quickly adopting AI as well. The conversations I’ve had come from senior allocators on whether it makes sense to use AI. And if so, how much?

Which begs the question: If AI can do your job, do you still have a job?

I was at a dinner last year where the CIO of a large endowment shared that the reason she knows what to look for in managers today, how to underwrite funds, and how to build a venture portfolio was due to the fact she made a plethora of mistakes on her way up the allocator ladder. Small mistakes, like mixing up a decimal on the spreadsheet which led to a venture fund needing a $10B outcome instead of a $1B outcome. Or like Jamie Rhode once said on Superclusters, that she failed to check before she made a commitment to a fund if the fund actually had the commitments that the GP advertised, leading to her check being a larger proportion of the final fund size than she anticipated.

A lot of senior leaders in the LP space seem to be quite skeptical of what AI can do for investment decisions in its current state, yet junior team members seem to widely adopt it to write memos, to inform investment decisions, to create portfolio construction models, and so on. And so far, there’s been a general consensus that AI, at least with respect to investment decision-making, has yet to reach its desired state. In one comment at the same dinner, a senior allocator remarked that one of her direct reports submitted a fund construction model that was built via AI and suggested that in order to return the fund, they needed almost a quarter of the companies to become unicorns. And when questioned, the junior allocator saw nothing wrong with the model. Only to further defend their choice. Or as Brandon Sanderson says in the talk, the problem with AI “is because they steal the opportunity for growth from us.”

“The process of creating art makes art of you. My friends, let me repeat that. The book, the painting, the film script is not the only art. It’s important, but in a way, it’s a receipt. It’s a diploma. The book you write, the painting you create, the music you compose is important and artistic, but it’s also a mark of proof you’ve done the work to learn because in the end of it all, you are the art. The most important change made by an artistic endeavor is the change it makes in you. The most important emotions are the ones you feel when writing that story and holding the completed work.

“I don’t care if the AI can create something that is better than what we can create because it cannot be changed by that creation. Writing a prompt for an LLM, even refining what it spits out, will not make an artist of you because if you haven’t done the hard part—if you haven’t watched a book spiral completely out of control, if you haven’t written something you thought was wonderful and then had readers get completely lost because your narrative chops aren’t strong enough, if you haven’t beat your head against the wall of dead ends on a story day after day until you break it down and find the unexpected path—you’re not going to have the skill to refine that prompt. The machine will have done the hard part for you and it doesn’t care.”

Growth comes from making mistakes. It comes from the struggle. The “distance travelled,” to borrow a term Aram Verdiyan used before. This is why investors often prefer partnerships and co-founderships. It’s why many firms have “red teams.”

There is probably a day when AI can do our job. But for now, the art of investing is in the friction it takes to make a decision. The character-building moments. The moments where you question your own priors. So if AI enables you to have more nuanced dialogues with yourself, if it challenges the way you think in ways you hadn’t considered before so that you look for evidence that either proves or disproves the null hypothesis, then there will still be room for the use of AI in investing. Otherwise, if you’re regurgitating scripts based on singular uninspired prompts, then you likely won’t have a job for long.

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!

January 30, 2026January 29, 2026

The Currency of Trust

Recently, I had three conversations about trust. So forgive me, but that’s the soup du jour today, as their comments are still swimming in my mind.

I spent some time with the Head of Investor Relations at a high nine-figure AUM firm. And he said something that echoed much of the reality of fundraising these days. “Fundraising is all about trust. It’s not about the performance metrics. It’s about who believes in you.”

Then, immediately after, I caught up with an LP friend, who said, “Investor relations is a wasted job title in VC. They’re glorified note takers and relationship managers. I won’t invest in any fund where I haven’t met the GP.” Only to later share how much we both admired a certain Head of IR at a large multi-stage fund.

At first glance, the irony is blinding. The funny thing is that both are equally as true. GPs have a bank account where they can deposit trust. They withdraw trust every time they make an ask. Whether it’s for capital or special terms on the term sheet or for a certain ownerships target or for a guest speaker for an event they’re hosting. Before a GP starts a firm, they need to bank a lot of trust. They should give more than they take. And to run a firm, there are three types of primary customers you need to bank trust with:

Founders,
Co-investors,
And LPs.

You also can’t take a loan on trust (in other words, outsource trust) before you’ve deposited enough trust in your own bank account. Or else, you’ll be in debt. If you’re in too much debt (i.e. have a negative balance), your reputation takes a hit. But when you’ve banked enough trust, you can have a separately managed trust account managed by others. An IR professional who manages the trust account with LPs. A community/platform person with co-investors and talent. And so on.

Having others manage these accounts too early in the firm lifecycle means taking debt and impacting reputation. So when my buddy who’s the LPs says he doesn’t like most IR folks, it’s because before the IR person was hired, the GP didn’t bank enough trust.

And the truth is trust is built not in grand gestures and one-off deals. It’s in the small interactions. How fast do you respond? Even when you’re busy, do you make time for people important to you? Do you remember what you talked about last time? Do you close the loop on advice you get from LPs—whether you use it or not? Do you remember their answer to ‘What did you do last weekend’ 15 weekends ago? Do you follow through with what you promise—even if it’s a restaurant recommendation you mentioned in the call?

In a conversation with a Fund I GP yesterday who successfully raised his 8-figure fund in 8 weeks (and yes, part of that duration was over the holidays), he said something I really liked: “Every LP is looking for returns. That’s a given. But every LP is also looking for returns plus X. Your job during the fundraising process is to find out what X is, and it may be less obvious than you think it is.” For some, X is undoing boredom. For others, it’s the front row seat to learn. Others still, it’s the prospect of social capital that will come with making an investment. And you can’t find any of these out, if you don’t spend the time to build trust with the other party.

Photo by Marek Piwnicki 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!

January 22, 2026January 21, 2026

Diligence on a GP’s Social Media Presence

A lot of what I will say applies similarly to assessing founders and with senior talent, but for the sake of this blogpost, I’m going to focus primarily on doing diligence on GPs.

Sequoia’s Pat Grady co-wrote a piece on AGI that’s been making its rounds the last few days. FYI, this post has nothing to do with AGI, so don’t get your hopes up. But in it, he shares:

Note the highlights above are all around how to better understand an individual’s internet presence. While not all-encompassing, understanding someone’s brand via their social media is more than just how many followers, likes, comments, and shares. As my good YouTuber friend once told me, “Not all subscribers are created equal. English-speaking personal finance content get paid the most per impression.” Analogously, the same is true for LinkedIn or Twitter/X content.

Just because you have 25K followers, how often are you just resharing your employer’s content? Or your portfolio company’s content? How often do you share your thought leadership? Do people follow you because of your perceived status or do people follow you because of the weight of your ideas? There’s a great Simon Sinek talk about the former Under Secretary of Defense on this, which I won’t bore you with the details, but if you want the full story, it’s here. In summary, if you no longer held the job title you do today, would people engage with you differently?

That’s what I’m trying to figure out.

The first filter is: What is your insight per post ratio? This includes reshares and comments they make on other people’s posts. At a high level, do you recognize what good content looks like?

The second filter is: What is your original insight per post ratio? How much of your activity is original ideas? Is that what people engage with? Or do they engage more with your reshared content? When they do engage, how?

Level 1 is a like. The least number of clicks to engage with you.
Level 2 is a reaction other than a like. It takes a second longer to do so, but is more intentional. To be fair, a spam-like content (i.e. “LFG”, “Proud of you”, “Excited”, etc.), I also put in this tier.
Level 3 is a thoughtful comment that you can’t use on any other post. They’ve read and thoughtfully engaged back. Also on this tier is a quick reshare.
Level 4 is a thoughtful reshare. Or on Twitter (still not easy to call it X), a “quote retweet.” You’re staking not only your personal brand and reputation with your own followers, but you’re also letting others know how you’ve thought about the content being shared.

It’s not a perfect scorecard, but I do keep a rough mental tally (which goes into my own memo) of what a GP’s social brand is. And at what point was there an inflection in their thinking and/or following. Usually quite correlated with each other.

Other things I find interesting to observe, but cannot be understood in isolation:

Most frequent commenters and reshare your content
Reactions-to-follower count ratio
Connections-to-follower ratio
How similar/different their content on LinkedIn vs Twitter/X vs Instagram/TikTok vs podcast platform is
AI-search optimization (AEO): What keywords and/or questions do certain GPs own in search traffic? How does it compare across ChatGPT vs Claude vs Gemini? And in incognito AI search.
Frequency of getting tagged by others on social media outside of viral periods
Endurance of content even when little to no engagement, usually for podcasts, blogs and newsletters. And why do they continue doing so even when it’s not producing the results they desire (more of a qualitative understanding on the personality traits of a GP)
Frequency of guest appearances on others’ content channels and how do those appearances’ views compare to said influencer’s average view-to-subscriber ratio

Photo by dole777 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!

Share this:

Share this:

Share this:

Share this:

Share this:

Share this:

Share this:

Share this:

Share this:

Share this: