Tag: james clear

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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 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:

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.

  1. 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.
  2. 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.
  3. 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.
  4. 99 Pieces of Unsolicited, (Possibly) Ungooglable Startup Advice — 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 — 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 LP — Pure therapy.
  • 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.

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.

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v27.0

The Earth has once again gone through another orbit around the only star within four light years from us.

In the past version of David, I’ve published many blogposts. Yet one of the most continual topics that owns real estate in my mind is the idea of the 99 unsolicited, but more importantly, non-googleable (figuratively speaking) pieces of advice. I’ve already published two blogposts on the respective topics of entrepreneurship and VC. And am now compiling more and an additional set of life hacks. I imagine, at some point, I will for other areas of my life I want to spend mind space on. Asking questions. Hosting interviews. Events. LP stuff. Just to name a few.

In other words, I am on a constant search for tactical pieces of insight in the corners of both the internet and safely kept (often unwittingly) in the grey matter in 7.8 billion locations. Or simpler, I want to know what others know.

I was listening to a podcast featuring James Clear earlier this year. And in it, he said something I completely agree with. “Almost every idea you have is downstream from what you consume. When you choose who you follow on Twitter, you’re choosing your future thoughts.”

In an age that offers us a wealth of information and a million topics, posts, comments, videos, and algorithms that will distract us, it becomes ever more prescient to be a great curator. It doesn’t even have to be for others. At the very minimum, for yourself.

The amount of time I’ve scrolled through metaphoric cat videos on YouTube is appalling. And I realize that whenever I do, I face a dry spell of ideas. Luckily only briefly.

As of now, the world’s top social media platforms’ algorithms work against us. It surfaces us content we are likely to enjoy. Content that is high likely to reinforce our confirmation bias, as well as availability bias of the world. And the biggest problem with that is we are fed cousins of the same information rather than new, and possibly dissenting information that would challenge our beliefs. After all, these apps’ goal is to keep us on the platform. Not to close the app and do something meaningful with our lives. I’m excited for the day we get to build our own algorithms for consumption. But for now, it has to be more manual.

James Clear also goes on to say in the same interview when Tim Ferriss asked how he chooses which books to read. “First thing is you got to be willing to quit books fast. If you have baggage around finishing books, then you’re just going to be stuck and you won’t move on quickly enough.”

I’m guilty of the counterfactual. I’ve long prided myself on seeing things through. In fact, I still do. But at least on the consumption part, I’m slowing down my rate of learning. This year, I’m going to start measuring the number of books, articles, and podcasts I fail to complete, as well as the number of long form content media (i.e. books, movies, articles, podcasts, etc.) that have inspired an idea or an output. The goal is to optimize for learning and insight rather than completion.

Since this is the first year I’m measuring it, I won’t be able to measure the delta. But I’ll leave this encased in amber for David v29.0 and future iterations.

Doing things that are unteachable

My sixth grade teacher once told me, “David, you should be proud [she] copied you. That means you have something worth copying.”

I, like many others, spent the first 22 years of my life copying and learning from someone else’s or multiple people’s playbook. And often still do. The four years after I worked on being different. From the words of someone I look up to, “Be interesting and interested.” Where I put more effort into being interesting — doing interesting things, having interesting perspectives, asking interesting questions. I worked to create things worth copying. And when I started this blog, I followed that same ethos. I did and will continue to do my best to share my findings and takeaways. So that others won’t have to fall through the same potholes as I did.

At least, that was my belief until December 8th last year.

I hosted an event. An event I’ve never been more excited to host. An event where I was intentional about as many details as I could. And a byproduct of being in the flow state at least twice a week. While I’ll likely spend another blogpost taking a deeper dive on this topic, it occurred to me that events, just like any other medium of consumption — movies, books, podcasts, shows, and so on — should be stories. And every story has a beginning, a middle, and an end. But more importantly, every great story has:

  • An inciting incident — something that compels the protagonist to leave their current timeline to embark on something spectacular
  • A main plot (with sometimes multiple side plots)
  • Character development — the protagonist, as well as other characters, grow over the arc of the story
  • An ending where the reader (viewer or listener) can imagine no other (tipping my hat to Robert McKee)
  • And to use the reader (et al’s) time in a way that is not wasted (tipping my hat to Kurt Vonnegut)

To my joy, it was as great if not greater than expected. The feedback was phenomenal. In my excitement and post-event high, I shared with many friends, colleagues, and family about how I thought about the event.

And to my dismay, while most were happy for me, a friend told me:

“You’re built different. I could never do what you do.”

In subsequent days, two other friends told me the same.

And it reminded me of something John Fiorentino once said. “The things that are going to be valuable are the things you can’t teach or copy.” While I was initially dismissive of this corollary, I now realize there might be some truth to it.

So, how does that change the stories I’ll share here or anywhere? In the past few years, every time I do something new, there ‘s usually a voice in the back of my head that asks me, “How would you catalog this adventure on your blog? What would be the title of the blogpost? What kind of title works best for SEO?”

Going forward, I’m going to ask that voice to hush. Not to say I won’t share my learnings, but I’ll preface now that my future writings may not be written for search engine optimization. It’ll be raw. And from title to body, a truer expression of what I want to share.

So where do I go from here?

I’ve hedged to be fair my entire professional career. I’ve done tons, which on paper, seems like a lot, but I’ve never fully spent time immersing myself in only one thing. And nothing but one thing. I’m context switching all the time, which probably means I live 20-30% less of a day than a focused person.

So I’m going to have to take more risks. ‘Cause I’m starting to believe that in order to do something that cannot be copied, I’m gonna need to focus more.

Photo by Mike Lewis HeadSmart Media 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!

Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.

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#unfiltered #66 Humans and Nonlinear Thinking

Humans are terrible at understanding percentages. I’m one of them. An investor I had the opportunity to work with on multiple occasions once told me. People can’t tell better; people can only tell different. It’s something I wrestle with all the time when I hear founder pitches. Everyone claims they’re better than the incumbent solution. Whatever is on the market now. Then founders tell me they improve team efficiency by 30% or that their platform helps you close 20% more leads per month. And I know, I know… that they have numbers to back it up. Or at least the better founders do. But most investors and customers can’t tell. Everything looks great on paper, but what do they mean?

When the world’s wrapped in percentages, and 73.6% of all statistics are made up, you have to be magnitudes better than the competition, not just 10%, 20%, 30% better. In fact, as Sarah Tavel puts it, you have to be 10x better (and cheaper). And to be that much better, you have to be different.

And keep it simple. As Steve Jobs famously said that if the Mac needed an instruction manual, they would have failed in design. Your value-add should be simple. Concise. “We all have busy lives, we have jobs, we have interests, and some of us have children. Everyone’s lives are just getting busier, not less busy, in this busy society. You just don’t have time to learn this stuff, and everything’s getting more complicated… We both don’t have a lot of time to learn how to use a washing machine or a phone.”

If you need someone to learn and sit down – listen, read, or watch you do something, you’ve lost yourself in complexity.

“Big-check” sales is a game of telephone. For enterprise sales or if you’re working with healthcare providers, the sales cycle is long. Six to nine months, maybe a year. The person you end up convincing has to shop the deal with the management team, the finance team, and other constituents.

For most VCs writing checks north of a million, they need to bring it to the partnership meeting. Persuade the other partners on the product and the vision you sold them.

And so if your product isn’t different and simple, it’ll get lost in translation. Think of it this way. Every new person in the food chain who needs to be convinced will retain 90% of what the person before them told them. A 10% packet loss. The tighter you keep your value prop, the more effective it’ll be. The longer you need to spend explaining it with buzzwords and percentages, the more likely the final decision maker will have no idea why you’re better.

Humans are terrible at tracking nonlinearities. While we think we can, we never fully comprehend the power law. Equally so, sometimes I find it hard to wrap my hear around the fact that 20% of my work lead to 80% of the results. While oddly enough, 80% of my inputs will only account for 20% of my results. The latter often feels inefficient. Like wasted energy. Why bother with most work if it isn’t going to lead to a high return on investment.

Yet at the same time, it’s so far to tell what will go viral and what won’t. Time, energy, capital investments that we expect to perform end up not. While every once in a while, a small project will come out of left field and make all the work leading up to it worth it.

When I came out with my blogpost on the 99 pieces of unsolicited advice for founders last month, I had an assumption this would be a topic that my readers and the wider world would be interested in. At best, performing twice as well than my last “viral” blogpost.

Cup of Zhou readership as of April 2022

Needless to say, it blew my socks off and then some. My initial 99 “secrets”, as my friends would call it, accounted for 90% of the rightmost bar in the above graph. And the week after, I published my 99 “secrets” for investors. While it achieved some modest readership in the venture community and heartwarmingly enough was well-received by investors I respected, readership was within expectations of my previous blogposts.

My second piece wasn’t necessarily better or worse in the quality of its content, but it wasn’t different. While I wanted to leverage the momentum of the first, it just didn’t catch the wave like I expected it to.

Of course, as you might imagine, I’m not alone. Nikita Bier‘s tbh grew from zero to five million downloads in nine weeks. And sold to Facebook for $100 million. tbh literally seemed like an overnight success. Little do most of the public know that, Nikita and his team at Midnight Labs failed 14 times to create apps people wanted over seven years.

When Bessemer first invested in Shopify, they thought the best possible outcome for the company would be an exit value of $400 million. While not necessarily the best performing public stock, its market cap, as of the time I’m writing this blogpost, is still $42 billion. A 100 times bigger than the biggest possible outcome Bessemer could imagine.

Humans are terrible at committing to progress. The average person today is more likely to take one marshmallow now than two marshmallows later.

Between TikTok and a book, many will choose the former. Between a donut and a 30-minute HIT workout, the former is more likely to win again. Repeated offences of immediate gratification lead you down a path of short-term utility optimization. Simply put, between the option of improving 1% a day and regressing 1% a day, while not explicit, most will find more comfort in the latter alternative.

James Clear has this beautiful visualization of what it means to improve 1% every day for a year. If you focus on small improvements every day for a year, you’re going to be 37 times better than you were the day you started.

While the results of improving 1% aren’t apparent in close-up, they’re superhuman in long-shot.

Source: James Clear

Photo by Thomas Park 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!

Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.

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Think like an LP to Get a Job in VC

I want to preface this piece by first saying, though I have LP (limited partner) friends, I’ve never been an LP. So take everything with a grain of salt. For that matter, even I have been an LP, still take this with a grain of salt. After all it’s just my one perspective on the world. Nevertheless, I hope this perspective helps to provide some context around the venture space. As it did for me.

For years, I’ve recommended my friends who were looking at startup job opportunities to think like a VC. And having chatted a number of firms over the years about scout, associate/analyst, venture partner roles, I’ve come to a new revelation. Or rather one that I’ve practiced for a while, but haven’t connected the dots until recently.

When you’re looking for VC job opportunities, think like an LP. I’ve written about the LP calculus a few times before, like:

Here are some questions I usually consider:

  • How have you thought about your own differentiation that gets you access to some of the uniquely fund-defining opportunities you have?
  • What are the startups in your anti-portfolio? And what have you learned since from them?
  • [if their funds are wildly different in fund size (i.e. Fund I – $20M, Fund II – $100M)] How do you think about fund strategy now versus Fund [t_now-1]?
    • For context, usually each subsequent fund doubles in size. i.e. Fund I $20M, Fund II $40-50M, Fund III $80-100M
  • [If they have fund advisors, EIRs, and/or scouts] How do you pick advisors? What is your mental model for picking scouts?
    • Or one of my favorite phrasings: How do you differentiate the good from the great [advisors/scouts]?

Over the weekend, my friend sent me a great podcast for me to unwind. In it, I found an unlikely hero soundbite. “Your library holds a lot of value that you may not know until the story arrives. […] No one’s selling characters ’cause they’re one story away from this character becoming a hit.” While its context is related to why Marvel won’t sell any of its superheroes, Alex Segura‘s, co-president of Archie Comic Publications, anecdote proves just as insightful to the world of venture.

Discovering first-time early-stage founders is hard. The same is true for finding the next killer GP or venture firm. AngelList’s Rolling Funds are democratizing access to capital, lowering the barrier to entry for emerging fund managers. And really the success of a fund is determined by its MOIC – multiple on invested capital. 5x and up would be ideal. And that, like I mentioned in my last blogpost, boils down to the fund’s top one or two winners. Loosely analogized to a fund’s unicorn rate (percent of portfolio that are unicorns). In other words, the “one [investment] away from this [fund] becoming a hit.”

To see if a fund can consistently find those stories boils down to its systems. Often times, you’re joining a fund that has yet to have a runaway success. Or a fund that has a fund returner. So, instead, you’re looking at their thesis and if their thesis allows them to be:

  1. The best dollar on the cap table of a startup in their scope
  2. Forward-thinking enough to see where the market is heading, rather than where it’s been
    • And by definition of being forward-thinking, taking bets/risks that few other VCs would, yet calculated enough to make logical sense given the trajectory of the market. In other words, is the thesis grounded on first principles, yet able to capture their second-order effects?
    • That, in turn, requires you as a VC applicant to have decent literacy in the market the firm is betting in.

As James Clear, author of Atomic Habits, wrote, “You do not rise to the level of your goals. You fall to the level of your systems.” What are their mental models? Fund strategy? How do they think about portfolio construction? About capital allocation? And more importantly, time allocation?

If you’re looking to learn more about GP-LP dynamics, I highly recommend Samir Kaji’s Venture Unlocked podcast and Notation Capital’s Origins podcast.

Photo by Micheile Henderson on Unsplash

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