The Japanese word for the business practice of building consensus and hearing people’s opinion before the decision or change is formally proposed.
And I don’t think I know the English parallel to that.
I’ve always told the GPs and founders I work with/have invested in that they should involve their investors in major decisions before they’re proposed and discussed. That no board meeting or LPAC (LP advisory committee) topics should ever be a surprise. It also shows that you’re not talking at people and you’re trying to involve them as a true partner for your business. Both LPs and VCs (to founders) highly prefer that. Conversations should never be out of convenience, but they should feel intentional. You also don’t have to be perfect, neither should you pretend to be with the people who’ve chosen to be with you long-term. Just as you shouldn’t hide any trauma, sentiment, and harbored feelings from your romantic partner and family.
The quarterly board meeting and the LPAC meeting are merely formalities. You should be able to trust your investors outside of those structured events. You may not need to bring up certain topics because it’s not written in the term sheet or limited partner agreement, but that doesn’t mean you shouldn’t. Partner struggles. Off-thesis investment opportunities. Major hires. Or layoffs.
There are a lot of VCs and LPs who would love to be true partners with you, but sometimes they don’t know how to help unless you ask for help before you make the decision. Have the conversation early on about how they would like to be involved in your business. And for those who do, go to them before you propose a decision or change.
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.
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!
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 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.
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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 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 Gradyco-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
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.
One of the most interesting self-reflective questions I think GPs should ask is: If someone else had the exact same strategy and offered the exact same terms, why would someone not pick you over another VC? That’s adverse selection.
One of the three pillars (or five pillars, depending on who you ask) of underwriting a venture fund is winning. The others being seeing and picking (and supporting and selling). But sometimes what’s more interesting than underwriting why a GP wins is understanding all the reasons they won’t win.
It’s an interesting thought exercise I like working through with a GP. “Why won’t a founder let you invest?” or “Assuming you wanted to invest, why would you lose out on a deal?”
The most common answers are always:
“I missed the timing.”
“There was no more space left.”
“They weren’t raising at the time.”
In my opinion, while possibly true, all cop-out answers. Then I follow up: “Assuming you wanted to invest, and there’s space left, and they’re currently raising, why would a founder say no to you?” Or “Why wouldn’t you be able to invest?” More often than not, I get an answer along the lines of: “I win (almost) every deal I want.” Or “I have yet to raise my fund.”
Even if true historically, it doesn’t answer the question. It’s like asking a job candidate: “Tell me about your weakness.” And they respond with, “I’m too honest.” Or worse, “I have no weaknesses.”
What I’m trying to get at in these questions is not the “right” answer. There is none. But rather what are the reasons you’ll fail to win a deal. Which of those reasons are areas where you would like to improve upon? Which of those reasons are areas where you will continue to be unrelenting on? What will you not change? Only then can I get a better understanding of the GP you will become 2-3 funds from now. And if so, does it make sense to do business with each other today?
There’s a Fund I GP I ended up investing in. When I first asked him the question above, he reached the conclusion that his pitch and value-add resonated more with second-time founders than first-time founders at the pre-seed stage. And given that he wanted to grow into a lead investor eventually, what he had to figure out was how to build a strong enough brand with first-time founders, requiring both education and intentional positioning. For me as an LP, it became easy for me to see how he would grow into a Fund II GP. Between then and his next fundraise, I’d just track how many first-time founders he invested in, try to spend time with them at events, and ask why did you take this GP’s check and what did you really want from him.
There is no right answer as to what founders wouldn’t want to work with you. It’s just an exercise of self-awareness, so you can figure out what’s worth working on and what’s not. Adverse selection reasons I’ve heard in the past, in no particular order, include:
Political alignment
Naming a firm after their own name instead of an ideal (yes, that is a real answer I’ve gotten before)
Speed to make a decision
High ownership targets
Response time, including taking the holidays/weekends off when their peers might still be dealmaking
Lack of brand awareness
No founding experience
No experience at a large established firm
No relationships with key potential customers
Values shared publicly / controversial opinions
Personality (i.e. too nice, people pleaser, argumentative, arrogant, name-dropping/logo-shopping, too humble, etc.)
Lack of talent networks
Having invested in a competitor
A homogenous partnership
A rumor that is widespread but may not have real credence
A single remark from an influencer in the ecosystem (or a close friend), then what’s more interesting is why someone would say something like that
The way a GP dresses (especially important in certain geographies outside of the US)
The initial outreach was done by a junior team member or a broker/dealer
Subsequent conversations done by a junior team member
A reference call with their network done in poor taste
Someone with no board experience asking for a board seat
Having someone else on the team take the board seat even though you did the deal and the founder wanted you
Aggressive term sheet terms (1X+ liquidation preferences – participating and preferred)
Having no respect for prior round investors (especially, in relation to their most helpful investors so far, often related to their pro rata)
Badmouthing their existing investors and/or teammates
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.
“You’re making decisions in an incomplete vacuum. What I think many people should do more of, in terms of those mental models, is frame it in the reverse. Which of these decisions am I going to make that is the most regret-minimizing? That I have the least likelihood of regretting later on in life, assuming that in most cases, I will be wrong.” — Peter Walker
The holiday season has always been a great time to celebrate the movers and shakers in our world. This season we’re celebrating my personal favorites in the VC and startup world. This episode, it’s with my man, Peter Walker, who creates some of the industry’s most talked charts and graphics around the ebbs and flows of tech innovation.
Peter Walker runs the Insights team at Carta, where he works to make startups a little less opaque for founders, investors, and employees. Prior to Carta, he was a marketing executive for the media analytics startup PublicRelay and led a data visualization team at The Atlantic magazine. He lives in San Francisco, but you can find him on LinkedIn (see links below).
[00:00] Intro [02:52] Peter’s first brush with entrepreneurship [11:49] 996 work culture [17:11] Peter’s disclaimer on his data [21:27] Regret-minimization when investing [24:24] One example of regret-minimization [26:07] How does Peter choose which conferences to go to? [29:33] Conference panels are often bad [36:22] The incongruencies of what GPs say publicly and privately [41:43] Peter’s first data visualization [44:18] Why is soccer underrated in the US? [46:10] What great lengths has Peter gone for his friends? [48:21] One worrisome trend we’re going to see in 2026 [52:18] One optimistic trend to look forward to in 2026
“No one has to force you to work long hours if you really want to. The founders and early employees who push hardest aren’t usually doing it because someone set the office lights to stay on until midnight. They’re doing it because they care. It’s not obedience—it’s compulsion.” — Cristina Cordova
“There’s a growing recognition that that sense of compulsion, it very rarely lasts for 10 years. […] It’s very rare to find that one thing—that one set of problems—that can get you so excited for your entire life.” — Peter Walker
“Curiosity is the art of asking questions where you’re not married to the answer.” — Matt Huang
“You should probably, if you’re a founder, for instance, selectively ignore at least half of what I’m saying because it doesn’t apply to you. And your job as a founder, your job as an investor, your job as a thoughtful person is to figure out which half.” — Peter Walker
“If you torture the data long enough, it will confess to anything.” — Ronald Coase
“You’re making decisions in an incomplete vacuum. What I think many people should do more of, in terms of those mental models, is frame it in the reverse. Which of these decisions am I going to make that is the most regret-minimizing? That I have the least likelihood of regretting later on in life, assuming that in most cases, I will be wrong.” — Peter Walker
“The worrisome part is that sometimes [selling founder secondaries] is at pretty early-stage companies—seed, A. Sometimes, it’s for $10,000 and I don’t know what happened there. Sometimes, it’s for a really sizable amount of money—seven figures. To me, that is a bubble sign. That is as close as you can get to capital is chasing consensus too much, and therefore, smart founders are just taking advantage and taking stuff off the table.” — Peter Walker
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.
This is a blogpost where I’ll risk sounding like an asshole. Probably am already one to some, although I try not to be.
My job—as well as all other investors, hiring managers, talent agents, sports scouts, just to name a few—is to make decisions relatively quickly when faced with the pure volume of inflows. Not necessarily investment decisions, but in a brief interaction, it’s my job to figure out if I want to continue spending time with someone. And if I do know, I need to set expectations clearly as soon as I can. Usually within the first interaction. Because of that, I find it useful to develop heuristics.
(max age at which the knowledge one has today would still be impressive) – (age today) = (# of F’s given)
Where… negative F’s is a lost cause. You’re too late to the game. Zero F’s means it’s to be expected. Expectation meets reality. And the larger the number of positive F’s given, the more impressive you are.
Let me contextualize this.
Today, I know that 7 x 8 = 56. Not impressive at all. I’m 29, at the time of writing this post. The max age knowing what 7 x 8 is, and still be impressive, is probably 5 years old.
The Pythagorean Theorem probably caps out on the “impressive scale” at 8 or 9-years old before it’s to be expected. Maybe 10. There are some pieces of knowledge that have an expiration date on impressiveness. If you know E=mc2 at 6-years old, you might be a genius. If you brag about it at 30-years old, people will wonder what you’ve done with your life. That’s not to discount the folks who spend their life on the actual intricacies of the equation. There is also an age where it starts being worrisome if you still don’t know how to do something. At 10, if you know how to file taxes, people will shower praises at you. At 40, if you don’t know how to file your taxes, people will scoff.
The interesting thing is it extends beyond simple math. In venture, there is a certain point in your career that you need to know what pre- and post-money SAFEs are. You need to know the responsibilities of a board member, if you want to be a lead investor. You need to know how to file your K-1’s. You need to know what qualifies for QSBS. If you’re three months into your job as a VC, I don’t expect you to know how to negotiate pro-rata rights when a downstream investor wants you to sell a piece of your equity so they can keep their ownership targets. If you’re a VC, and not a GP, I don’t expect you to know the difference between a 3(c)(1) and a 3(c)(7) entity and that if you have a 3(c)(1) structure, then any LP owning more than 10% will be subject to the look-through rule and every single underlying LP in theirs counts as a beneficial owner and counts towards your 100 investor cap.
There is also so much free content online at this point that the max age where someone will still be impressed by a certain skillset or knowledge will continue to decrease as media democratizes knowledge. Made even easier with AI. Although do take niche knowledge generated by AI with a grain of salt.
The second part, which is equally as important, is: How did you acquire that piece of knowledge? For instance, one of the common “Would you rather?” assessments when I first jumped into venture was: Would you rather invest in someone who graduated from MIT with a 4.0 GPA or someone who took every free computer science course online to learn to built a software product? The common consensus on our team was the latter. The latter shows drive and intrinsic motivation. Critical for someone who’s a founder. Aram Verdiyan and Pejman Nozadcall it “distance travelled”, a terminology I’ve since borrowed.
As such, both the insight and the insight development matters. It’s what I look for when I have an intro conversation with a GP and/or founder. It’s what I seek when I go to an investor’s annual summit. So much so, that in my notes, I keep track of who has the highest “insight per half hour.” And I have an extreme bias towards those who have something insightful to share almost every time I have a conversation with them, as well as those who accumulate insights faster than others.
Of course, this isn’t the end all, be all heuristic, but I find it helpful as a rough rule of thumb when a GP claims to have insight in a given area.
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 talking to an emerging manager raising a $10M fund recently. He shared a comment, likely off-the-cuff, but something I’ve heard many other emerging managers echo. “This year, most of the dollars deployed into venture has concentrated in only a few big funds.”
Not this manager in particular, but I’ve heard so many other Fund I or Fund II GPs say that. Blaming their struggle with fundraising on the world. It’s not me, but the world is conspiring against me. Or frankly, woe is me. But there is no LP who ever wants to hear that. Building a firm is hard. Building a startup, likely harder. No one said it’ll be easy. So let’s not pretend it’ll be all sunshine and rainbows. If you thought so, you’re deeply misinformed. If you’re going to be an entrepreneur of any kind, you need to take matters into your own hands. You cannot change the world (at least not yet). But you can change how you approach it.
That said, the mega funds who are raising billions of dollars are raising from institutions whose minimum check size is in the tens, if not hundreds of millions. These same institutions would never invest in an emerging manager. Their team, their strategy, and their institution isn’t built for it. When they have to deploy hundreds of millions, if not billions, a year into “venture” with a team of four or less, you’re not their target audience. So as an emerging manager, those mega funds are not your competition at least when it comes to LP capital.
You’re competing against all the other funds (likely emerging managers) at your fund size. Who can take the same check size you can take. That’s who you’re competing with. So whether you like it or not, billions going to the mega funds has, from a fundraising perspective, nothing to do with you.
If you are looking for reasons to fail, you will find one.
As the great Henry Ford once said, “Whether you think you can, or you think you can’t, you’re right.”
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
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.
One of the most interesting lines I heard on a podcast that Mike Maples was on was: “90% of our exit profits have come from pivots.” Which I first wrote here. Then here. It’s a line that lives rent free in my mind. Ideas, startups, roadmaps, and goals change all the time. I get it. That’s life. Very, very few folks are folks who unilaterally pursue one thing their entire lives. And of those who do, they’re not all successful.
Another friend of mine whose track record speaks for itself, having invested and involved herself in multiple boards before those companies became unicorns and even after, once told me that the idea she invests in is irrelevant. As long as it has grounds and can be adjacent to a large market. The primary thing she looks for is the founding team.
Early-stage investors obsess about people. They’re not wrong. Some are misled by these “VC-isms.” Others still have their own way of underwriting them. I don’t have a crystal ball. I’m also not the smartest person to be dishing out predictions. I have a rough idea of what will change, though I may not always be right. But I don’t know how they’ll change. Or when. So I’ve lived an investing career obsessing over things that don’t change. Or as Naval Ravikant puts it: “If you lived your life 1000 times, what would be true in 999 of them?”
I’ve written about flaws, limitations and restrictions before. But to quickly surmise:
Flaws are things you can overcome. Limited track record. Never managed a team. Never scaled a product. Limited access to capital.
Limitations are imposed by others and/or the environment. Gravity dictates that objects don’t fall upward. There are only 24 hours in a day. If you’re not based in the Bay Area, it’s harder to raise capital. Certain investors prefer co-founders and partnerships. Certain investors care about warm intros. The list goes on.
Restrictions are rules imposed on yourself by yourself. Batman can’t kill. You only invest in solo founders. You only invest in healthcare. You don’t invest in anyone outside the Ivy League schools. But some restrictions go deeper. You’ll never hire from a job portal again. You never hire or invest outside of your network. You won’t invest or hire having never met someone in person. You need to meet their spouse before you make a hiring decision. You don’t invest in single parents. You don’t hire anyone who doesn’t read at least one book per month. You micromanage. You don’t hire anyone who cannot curse. And yes, I’ve heard all of the above and more. My curiosity is always: Why do you impose such restrictions on yourself? What is the story you’re not telling me? Is out of a fear or admiration?
All that to say:
Flaws will and can change if it is a priority. But won’t change if they’re not.
Limitations might change, but it’s outside of your and my control. And I don’t get paid to pray to the weather gods.
Restrictions often don’t change.
Whether you admit it or not, certain habits are hard to change and unlearn. It’s possible. But that requires you to not only be aware of it, but also actively want to change it. Other habits are second nature. How you treat others. How you start each conversation. Why you look both ways before crossing even an empty street. Why you’ve sold yourself a particular personal narrative. Why you have to invest a certain thesis.
The world seems to always be trying to stay on top of things, but there seems to be far less dialogue around how to get to the bottom of things. To me, when it’s underwriting a person and their team, it’s about underwriting what doesn’t change rather than underwriting what could.
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
“The intuition part comes from activities of creativity that change your perspective.” — Yiwen Li
Yiwen Li is a seasoned investor with a successful track record of investing in AI, blockchain, and healthcare tech while developing global business partnerships to fast-scale the business.
Yiwen is currently Head of Venture Investments at Bayview Development Group, a global family office with diverse exposure public market, private equity, venture, and real estate. Prior, she was a Principal at Alumni Ventures, responsible for end-to-end multi-stage investments focused on blockchain and fintech. She was Director for Corporate Strategy at Masimo (Nasdaq: MASI). She built an innovation pipeline in healthcare connectivity and data analytics. She was Director for Corporate Development at NantHealth (Nasdaq: NH), where she established the international business division. Yiwen started her career at Capital Group in equity research.
Yiwen is an Advisory Board member of C-Sweet. She served on the board of Give2Asia as the chairman of the finance committee and a member of the investment committee. She was an advisory board member for the Asia Society where she co-founded the “Asian Women Empowered” initiative. She was recognized as the” Top 50 Women Leaders in San Jose 2024 and 2025”, “Top 50 Women in 2019” and the “Most Inspirational Women in Web 3”. Yiwen is also the author of one of the best sellers “Make the World Your Playground”, inspiring women to find their unique path. She is a frequent speaker on innovation and emerging technology trends.
Yiwen holds a Master from the London School of Economics and a Master from the University of Vienna. She also graduated from the Venture Capital program at UC Berkeley and the Private Equity Program at Wharton. She was selected to be one of the ” Young American Leaders” at Harvard Business School. Yiwen is a recipient of the European Union’s Erasmus Mundus scholarship. She is fluent in Mandarin and German, worked and lived in Europe, Asia, and US.
[00:00] Intro [02:07] Yiwen’s childhood [05:00] Jazz singing [06:14] The value of learning languages [09:01] How to build intuition around emerging managers [14:51] Getting to the bottom of a GP’s motivation [16:33] What percent of GPs are not in VC for the right reasons? [19:47] Does success fuel or inhibit ambition? [24:17] The cost of knowledge is cheaper [24:56] Competitive edges in the current world [27:06] Why creative activities matter [31:21] Advice to emerging LPs [32:42] Post-credit scene
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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.
