Peter Teneriello has been a career-long investor in the private markets. He has experience as an allocator across a range of institutional types, from wealth management firms to pensions and endowments, and helped launch the venture capital program for the Texas Municipal Retirement System. Other past experiences of his have included leading finance/operations for a venture-backed startup, in addition to vetting investments for a family office and working with their portfolio companies. Over the years he has also written about his investing experience on Medium and Substack.
He is a graduate of the University of Notre Dame as well as the Kauffman Fellows Program, an executive education program focused on venture capital and innovation leadership. He wears many hats.
[00:00] Intro [03:57] The origin of Peter’s nickname [05:16] How was boxing formative to who Peter is today? [07:25] The art of the first conversation with a GP [11:46] How did TMRS deploy $1B into VC and PE annually? [19:45] Looking at the underlying portfolio of companies [24:06] How overlap in venture portfolios affect re-up decisions [26:55] Marks from an LP perspective [30:52] Qualitative vs quantitative information [34:45] Signal vs noise in the private markets [40:46] When Peter shaved his head in front of an entire lecture hall [45:09] The most recent update to the Peter OS [51:17] Thank you to Alchemist Accelerator for sponsoring! [53:53] If you enjoyed the episode, consider dropping a like, comment or share as it really helps me create content that is interesting to you
“Don’t overweight the quantitative over the qualitative.” – Peter Teneriello
“It’s not to be in the consensus out of a misguided sense of self-preservation; it’s approaching your life’s work with creativity and conviction and treating it like the art that it is.” – Peter Teneriello
Last week, Youngrok and I finally launched our episode together on Superclusters. In the midst of it all, we wrestle with the balance between the complexity and simplicity of questions to get our desired answer. Of course, we made many an allusion to the DGQ series. One of which, you’ll find below.
In many ways, I started the DGQ series as a promise to myself to uncover the questions that yield the most fascinating answers. Questions that unearth answers “hidden in plain sight”. Those that help us read between the lines.
Superclusters, in many ways, is my conduit to not only interview some of my favorite people in the LP landscape, but also the opportunity to ask the perfect question to each guest. Which you’ll see in some of the below examples.
Asking Abe Finkelstein about being a Pitfall Explorer and how it relates to patience (1:04:56 in S2E1)
What Ben Choi’s childhood was like (2:44 in S1E6) and how proposing to his wife affects how he thinks about pitching (1:05:47 in S1E6)
How selling baseball cards as a kid helped Samir Kaji get better at sales (45:05 in S1E8)
In doing so, I sometimes lose myself in the nuance. And in those times, which happen more often than I’d like to admit, the questions that yield the best answers are the simplest ones. No added flare. No research-flexing moments. Where I don’t lead the witness. And I just ask the question. In its simplest form.
For the purpose of this essay, to make this more concrete, let’s focus on a question LPs often ask GPs.
“Tell me about this investment you made.“
In my mind, ridiculously simple question. Younger me would call that a lazy question. In all fairness, it would be if one was not intentionally aware about the kind of answer they were looking to hear OR not hear.
The laziness comes from regressing to the template, the model, the ‘what.’ But not the ‘why’ the question is being asked, and ‘how’ it should be interpreted. For those who struggle to understand the first principles of actions and questions, I’d highly recommend reading Simon Sinek’s Start with Why, but I digress.
Circling back, every GP talks about their portfolio founders differently. If two independent thinkers have both invested Company A, they might have different answers. Won’t always be true, but if you look at two portfolios that are relatively correlated in their underlying assets AND they arrive at those answers in the same way, one does wonder if it’s worth diversifying to other managers with different theses and/or approaches.
But that’s exactly what makes this simple question (but if you want to debate semantics, statement) special. When all else is equal, VCs are left to their own devices unbounded from artificial parameters.
Then take that answer and compare and contrast it to how other GPs you know well or have invested in already. How do they answer the same question for the exact same investment? How much are those answers correlated?
It matters less that the facts are the same. Albeit, useful to know how each investor does their own homework pre- and post-investment. But more so, it’s a question on thoughtfulness. How well does each investor really know their investments? How does it compare to the answer of a GP I admire for their thoughtfulness and intentionality?
(Part of the big reason I don’t like investing in syndicates because most outsource their decision-making to larger logos in VCs. On top of that, most syndicate memos are rather paltry when it comes to information.)
The question itself is also a test of observation and self-awareness. How well do you really know the founder? Were you intentional with how you built that relationship with the founder? How does it compare to the founder’s own self-reflection? It’s also the same reason I love Doug Leone’s question, which highlights how aware one is of the people around them. What three adjectives would you use to describe your sibling?
Warren Buffett once described Charlie Munger as “the best thirty-second mind in the world. He goes from A to Z in one go. He sees the essence of everything even before you finish the sentence.” Moreover in his 2023 Berkshire annual letter, he wrote one of the most thoughtful homages ever written.
As early-stage investors, as belief checks, as people who bet on the nonobvious before it becomes obvious, we invest in extraordinary companies. I really like the way Chris Paikdescribes what we do. “Invest in companies that can’t be described in a single sentence.”
Invest in companies that can’t be described in a single sentence
And just like there are certain companies that can’t be described in a single sentence — not the Uber for X, or the Google for Y — their founders who are even more complex than a business idea cannot be described by a single sentence either. Many GPs I come across often reduce a founder’s brilliance to the logos on their resume or the diplomas hanging on their walls. But if we bet right, the founders are a lot more than just that.
Of course, the same applies to LPs who describe the GPs they invest in.
In hopes this would be helpful to you, personally some areas I find fascinating in founders and emerging GPs and, hell just in, people in general include:
Their selfish motivations (the less glamorous ones) — Why do this when they can be literally doing anything else? Many of which can help them get rich faster.
What part of their past are they running towards and what are they running away from?
All the product pivots (thesis pivots) to date and why. I love inflection points.
If they were to do a TED talk on a subject that’s not what they’re currently building, what would it be?
Who do they admire? Who are their mentor figures?
What kind of content do they consume? How do they think about their information diet?
What promises have they made to themselves? No matter how small or big. Which have they kept? Which have they not?
How do they think about mentoring/training/upskilling the next generation of talent at their company/firm?
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.
Winter Mead is the Founder and Managing Member of the investment firm Coolwater Capital, which exclusively focuses on emerging managers and technology investments. Coolwater is an academy for training, building and scaling emerging managers, a curated community of VC investors and early-stage investment specialists, and an investment firm. Coolwater has helped launch over 175 emerging managers, establishing strong ties and trust with these managers, who form the foundation of the Coolwater community. Winter is also the author of “How To Raise A Venture Capital Fund”.
Prior to Coolwater, he played a key role in an evergreen investment fund at SAP, co-founded the LP transparency movement called #OpenLP, and served on the committee for the Institutional Limited Partners Association (ILPA), which sets the standards for the private equity industry. Winter’s extensive experience includes private equity and venture capital roles in San Francisco, institutional fund investments, direct technology investments, and angel investing.
He also served as junior faculty at Stanford Graduate School of Business, holding degrees from the University of Oxford and Harvard University, and now resides in Utah with his family, passionately solving business challenges.
[00:00] Intro [03:14] Why Winter biked across Spain with a flask of maple syrup in his back pocket [05:55] How did Amy Lichorat change Winter’s career? [07:15] How did Winter get into Hall Capital Partners? [10:34] What makes Hall Capital Partners special? [13:49] How office design affects the team’s ability to learn [23:49] The value of living in the Bay Area [27:17] Where to meet founders and VCs in the Bay Area [33:35] Institutional checks vs angel checks [38:58] Two of Winter’s decision-making frameworks for angel investments [41:58] How to build an LP investment thesis [52:53] The interplay of fear and diligence [59:44] Two rookie mistakes that emerging LPs make [1:05:34] The chip on Winter’s shoulder [1:09:03] Thank you to Alchemist Accelerator for sponsoring! [1:11:39] If you enjoyed this episode, consider subscribing and/or sharing!
Youngrok Kim is a Partner at GREE LP Fund, a Fund of Funds operating in the US and Japan. Previously, he held the position of SVP at Recruit Strategic Partner, the strategic investment arm of Recruit Holdings, a major internet company in Japan. Youngrok began his career as an engineer at Goldman Sachs before transitioning to a VC career at ARCH Venture Partners in Chicago. He earned an MBA from the University of Chicago and received his degrees in Information Technology from Aoyama Gakuin University in Tokyo.
[00:00] Intro [04:10] How did Youngrok find himself in Japan? [09:29] Picking up the Japanese language [20:29] How did Youngrok go from Japanese guitarist to being an LP? [26:50] From pitching LPs on a fund-of-funds to getting a job offer from a prospective LP [33:21] GREE LP Fund’s hiring process [37:40] The three sources of data that helped Youngrok’s fund-of-funds thesis come together [44:17] Superpowers and where to reference check them [48:57] Simple versus nuanced questions for fund managers or reference checks [56:12] One thing that many GPs think is special but actually isn’t for an LP [58:52] What makes a good LPAC member? [1:00:26] What are typical questions GPs have for their LPACs? [1:05:28] Why GP friendships with other emerging managers might be becoming less important? [1:11:55] A fun fact about Youngrok’s name [1:12:55] Playing a number game with Youngrok [1:16:05] Thank you to Alchemist Accelerator for sponsoring! [1:18:41] Like, comment, or subscribe if you enjoyed this episode!
“Reference calls have a lot of nuance. No one wants to say bad things about their investors. And no one wants to say something bad about their co-investors. So my job is to find out the subtle nuances.”
I am under no illusion that there is a hell of a lot of interest in the LP landscape today. Not only from GPs who are realizing the difficulties of the fundraising climate, but also from aspiring and emerging LPs who are allocating to venture for the first time. The latter of which also have a growing set of interests in backing emerging GPs. And in the center console in this Venn diagram of interests lies the education of how to think like an LP.
There is no shortage of content. LPs are also starting to make their rounds. You’ll often see the same LP on multiple podcasts. And that’s not a bad thing. In fact, that’s very much of a good thing that we’re starting to see a lot more visibility here and that LPs are willing to share.
But we’re at the beginning of a crossroads.
A few years back, the world was starved of LP content. And content creators and aggregators like Beezer, Ted, Nick, and Chris, were oases in the desert for those searching. Today, we have a buffet of options. Many of which share listenership and viewership. In fact, a burgeoning cohort of LPs are also doing their rounds. And that’s a good thing. It’s more surface area for people to learn.
But at some point, the wealth of information leads to the poverty of attention. The question goes from “Where do I tune into LP content?” to “If I were to listen to the same LP, which platform would I choose to tune into?“
After all, we only have 24 hours in a day. A third for sleep. A third for work. And the last competes against every possible option that gives us joy — friends, hangouts, Netflix, YouTube, hobbies, exercise, passion projects and more.
In the same way, Robert Downey Jr. or Emma Stone or Timothée Chamalet (yes, I just watched Dune 2 and I loved it) is going to do multiple interviews. With 20, 30, even 50 different hosts. But as a fan (excluding die-hard ones), you’re likely not going to watch all of them. But you’ll select a small handful — two or three — to watch. And that choice will largely be influenced by which interviewer and their respective style you like.
While my goal is to always surface new content instead of remixes of old, there will always be the inevitability of cross-pollination of lessons between content creators. And so, if nothing else, my goal is to keep my identity — and as such, my style — as I continue recording LP content. To me, that’s the human behind the money behind the VC money. And each person — their life story, the way they think, why they think the way they think — is absolutely fascinating.
In closing
There’s this great Amos Tversky line I recently stumbled upon. “You waste years by not being able to waste hours.” And in many ways, this blog, Superclusters, writing at large, and my smaller experiments are the proving grounds I need to find my interest-expertise fit. Some prove to be fleeting passions. Others, like building for emerging LPs, prove to be much more.
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.
Abe Finkelstein, Managing Partner at Vintage, has been leading fund, secondary, and growth stage investments focused on fintech, gaming, and SMB software, among others, leading growth stage and secondary investments for Vintage in companies like Monday.com, Minute Media, Payoneer, MoonActive and Honeybook.
Prior to joining Vintage in 2003, Abe was an equity analyst with Goldman Sachs, covering Israel-based technology companies in a wide variety of sectors, including software, telecom equipment, networking, semiconductors, and satellite communications. While at Goldman Sachs, Abe, and the Israel team were highly ranked by both Thomson Extel and Institutional Investor.
Prior to Goldman Sachs, Abe was Vice-President at U.S. Bancorp Piper Jaffray, where he helped launch and led the firm’s Israel technology shares institutional sales effort. Before joining Piper, he was an Associate at Brown Brothers Harriman, covering the enterprise software and internet sectors. Abe began his career at Josephthal, Lyon, and Ross, joining one of the first research teams focused exclusively on Israel-based companies.
Abe graduated Magna Cum Laude from the Wharton School at the University of Pennsylvania with a BS in Economics and a concentration in Finance.
Vintage Investment Partners is a global venture platform managing ~$4 billion across venture Fund of Funds, Secondary Funds, and Growth-Stage Funds focused on venture in the U.S., Europe, Israel, and Canada. Vintage is invested in many of the world’;s leading venture funds and growth-stage tech startups striving to make a lasting impact on the world and has exposure directly and indirectly to over 6,000 technology companies.
[00:00] Intro [03:22] How did Abe get his first job? [15:30] The currency of trust [17:12] How does Vintage view mistakes and weaknesses? [20:03] How Vintage organizes team offsites [28:42] The lessons Abe gained on people and long-term potential [33:47] Type 1 and Type 2 errors when evaluating GPs [36:00] How does Vintage work with their GPs and the GPs’ portfolio companies? [45:06] What Abe likes to see in a cold email [49:33] Funds that Abe says no to [51:18] When does fund size as a function of stage not make sense for Vintage? [54:51] Carry splits within a fund [1:02:08] What kinds of funds does Vintage not re-up in? [1:05:23] How did Abe become a Pitfall Explorer? [1:07:38] What Abe has learned over the years about patience? [1:11:05] One of Abe’s biggest blows in his career [1:16:23] Thank you to Alchemist Accelerator for sponsoring! [1:18:58] Like, comment and share if you enjoyed this episode!
Ok, before y’all rise up in arms, hear me out. And if by the end of this blogpost, you still want to bring the pitchforks and torches, so be it.
Generally, I get it. Who else is investing isn’t usually a great question. Because for most investors who ask this question, it means they’re outsourcing their conviction.
POV: you're at a tech week event full of contrarian investors who back founders at the earliest stage in frontier industries pic.twitter.com/k7p1cVNHjs
In fact, I wrote a quick LinkedIn (and tweet) post about it the day before yesterday. Which admittedly got a lot more attention than I expected. And if you have the time, it’s worth seeing the discussion on that post that ensued.
So, potentially hot take, I believe investors should ask the question. Who else is investing? It’s part of the diligence process. That said, when they ask that question is key. There’s a vast ocean between the shores of asking that question before you reach conviction and after.
If you pop the question before you reach conviction, well, we’ve seen the follies of that. Most evidenced by the manic rush of 2020 and 2021 into “hot deals” largely led by names that grew to popularity around the dinner table.
If you pop it after, it’s diligence. Where the availability of names shouldn’t convince you to bat or lack thereof to otherwise. But that you now have additional opportunities to reference check and cross-diligence the same opportunity. And it extends to the LP side as well. Jamie Rhode who’s now at Screendoor, said on a Superclusters episode that one of her greatest lessons as an LP was committing to a fund where there was a bunch of soft commits but far less in hard commits, and ended up overexposing Verdis (where she was at) to a single asset and taking a much higher ownership as an LP into a single fund.
Truth is, LPs pay GPs for their opinion. Not anyone else’s. And while given long feedback loops, no one really knows what’s right and what’s wrong except over a decade later and only in hindsight, you have to really believe it, and be able to back it up.
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’m in my fourth year of writing this blog and never once have I called myself or identified as a content creator. As many of you know, I write to think. I do so out of joy and intellectual stimulation. In many ways, I write for myself. Or better put, as a form of self-expression. Other than posting in the morning, as is thematically helpful for my blog, I don’t really have much cadence to posting. Nor have I looked too deeply on analytics. Nor have I really optimized for SEO. In other words, finding the top searched topics in my industry and writing a blogpost for each of those highly trafficked keywords. I haven’t done that, nor do I want to. I haven’t chased people down to subscribe. In fact, there are times I try to convince people to not subscribe (due to the scattered nature of my content).
To that end, I had not been a content creator.
But with the launch of Superclusters, for the first time, and still a work-in-progress, I am designing the content for someone other than my immediate self. Although, do I take opportunities to scratch my own itches? Yes… yes I do.
But in doing so, I am starting to think about creating content for others. And to do that, I need to look at what people like and tune in to.
Now at the end of Season 1, some quick learnings…
Note: The below gets a bit nerdy on numbers. Mostly as an accountability metric to myself to be paying attention to the below. This may not be for everyone, but in case you’re curious, and/or working on creating your own content, hopefully the below might be helpful.
Between all the platforms, YouTube seems to be the most popular channel. Followed by Apple Podcasts then Spotify. Where Apple Podcasts only has half or so the number of plays than YouTube does. And Spotify has three-quarters the listens compared to Apple.
May be helpful to note that YouTube and Apple Podcast count plays as just someone viewing the video for a split second (“greater than 0 seconds”), whereas Spotify counts a play as someone who’s played the episode for at least 60 seconds.
YouTube seems to be better for discovery than the other podcasting platforms, with over 4.5X the impressions compared to the next best, Spotify. 28K versus 6K. Tracked by last 30 days, not all time.
For short-form vertical content, TikTok continues to perform better than both YouTube and Instagram, especially for new audiences. Still perplexes me since I imagine the demographic on YouTube has more of my intended audience. Nevertheless, even on YouTube shorts, the shorts are consumed by a younger audience than the long-form videos on average.
Instagram, in general, performs poorly in terms of discovery among new audiences. But that might simply be, I haven’t learned the IG algorithms well enough yet. Moreover the new algorithm seems to prioritize completion percentage. And given that it’s hard to shorten even my short-form content to less five seconds or less, unless I just make people read while playing some kind of looped video in the background, Superclusters will likely continue to perform poorly on IG.
On YouTube, 90%+ of Shorts viewership comes from non-subscribers than subscribers. where 75-80% come from non-subscribers, the average for the full podcast episodes.
On YouTube, 41% of my audience comes from the US. TO break it down further, 50% comes from the US for long-form. 27% for short-form. Spotify, 67% comes from the US. Apple Podcasts, 87%.
Interestingly, by city, according to Apple Podcasts, New York City takes the cake on where my audience reside.
Across all platforms, most of my listeners/viewers are in the 35-44 age range. Accounting for almost 50% across all platforms. Followed by the 28-34 age group, then 45-59 age group. In general, Superclusters has a larger younger audience fan base on YouTube, compared to Spotify and Apple Podcasts. The latter two with similar distributions.
Superclusters audience is also about 75% male, 25% female.
While less than 0.05%, fun fact, the only other subtitles used on YouTube to tune into my podcast was French (outside of English).
Popularity versus watch time
The most popular episode on YouTube is Chris Douvos’, followed by Ben Choi’s. Episode 1 and Episode 6 respectively. My suspicion was that while both were super fun to record, Chris’ episode came first but may by the end of Season 2 be surpassed in viewership by Ben’s.
But what’s most fascinating to me is that among the nine episodes released for Season 1, on YouTube, the top four most popular episodes have shorter average watch times than the most bottom five. On average a two- to three-minute difference, where the least watched episodes happen to have 7-8 minutes of average watch time.
In closing
All in all, there’s a lot of work to do ahead. And as I’m recording Season 2 and my team is hard at work in editing those episodes, all of the above insights are helpful to keep my finger on the pulse. Do let me know if I’m missing any areas I should be paying attention to or measuring.
Otherwise, for Superclusters, I’ll see y’all again in early March for the launch of Season 2.
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.
A few years ago, in one of my favorite coffee shops on 7th Street in San Francisco, over a vanilla cold brew, a then 25-year old founder told me that he had recently taken his then-first vacation in five years. Took a full week off. Didn’t touch work at all. And just enjoyed it with his fiancée. But contrary to what one would expect, his body language that seemed to indicate the exact opposite of having a good time. Two hands cupped over his face, as he slowly dragged them both downwards in exasperation. Followed by many sighs.
He shared that in the time he was gone, the website crashed and the team had trouble bringing it back online. And when they finally did bring it back online, they were waiting for his approval to move forward. As such, didn’t bring it back online until he came back. With another large sigh, he went on to say that he’d never take another vacation ever again.
Running your own business is tough. Really tough. I get it. If you’re the founder, it’s your baby. And sometimes, it’s really hard letting go on what may seem like key decisions. Eventually, that becomes a slippery slope where I see too many founders needing to control every decision that goes on in the company. And even if you hired extremely well, you’ve capped your team’s potential by not letting them execute to their fullest capacity.
In the above dilemma, as you might know, it’s not a to-vacation-or-not-to-vacation problem. It’s a you-need-to-give-your-teammates agency problem. And it might seem obvious to you and me, to any third party observer. But it wasn’t to him. He was so frustrated that he was focused on the one new thing he did and believed that one new thing had a causal effect to a problem that was looming over his team’s head for a long time.
It is true that we are products of our scar tissue, but quite often, in an attempt to not be in the same situation again, people overcorrect. They take then run with the seemingly most extreme “solution.”
And in the times scar tissue start to form, start from first principles. Is taking a vacation really the biggest offender? Do great CEOs just not take time off? Is there something else that I’m not willing to admit about how the results played out?
What am I assuming to be true that may not have to be true? What are the raw facts, stripped of opinions and speculation?
Why was my team incapable of making that decision? Was it something that I told them before or did before that has since prevented them from making calls? What do I spend most of my day doing? Can I outsource some of my tasks? Some of my decisions? How would I do that? And only then, can I ask myself and others: what can I do from now on so that history doesn’t repeat?
Seeking and redefining excellence
And once you’re at the root of the problem, find others you admire who run organizations you admire.
Excellence is an interesting concept. One of the few words out there where its definition changes over the course of your life.
It’s one of the few words where it is not only different for every person, but that even within each person, every time you see something excellent, it sets a new bar and stretches that definition. Defined by only the most excellent thing you’ve seen.
The truth is that most great lessons happen to err on the side of examples. So to have people who define that word for you again and again are the “Sensei-s” you want in your life.
So spend time with others. Notice how they approach problems. And stretch your definition of excellence.
For the 25-year old founder who hadn’t worked any other job in his life, and only his own, there’s immense value in learning from others and building expertise at high-growth institutions. Or with people who you deeply respect.
Asking for the lesson
Tim Ferriss, on a recent episode with Noah Kagan, said, “Life punishes the vague wish and rewards the specific ask.” And I frickin’ love that line.
Be specific. No picking brains. You’re not a zombie or a vulture or a crow.
Not 30-minute coffee chats. Those quickly become recipes of asking for too much time with an amorphous ask. To a busy person, that 30-minute ask sounds like a recipe for losing 50 minutes to an hour of your life you can never get back. Including travel to and from. Time, as the only unreplenishable commodity, is precious. As Howard Lindzon said on the Superclusters podcast, when we’re young, we’re time-millionaires, but over time, we get poorer and poorer. We then become time-thousand-aires as we age. And eventually, we run out of temporal capital.
It is in times of need and struggle, that we often have the most prescient and specific ask to make of potential mentors.
“When in X situation, and after having Y results, my gut seems to tell me to do Z, but given that you’ve experienced these situations before or have likely seen these situations unfold, am I directionally accurate?”
In closing
There’s a lot of this hustle porn in the Bay Area. Loud claims of not taking any vacations or sleeping only three hours per night. Moreover media perpetuates and lionizes this way of living.
It’s not true. Science shows we do much better with eight hours of sleep. It shows that every so often, we need to take time to unwind, so that we can come back to be more efficient and inspired than before. You can clock in the hours, but that doesn’t mean you are producing quality in a one-to-one capacity.
And I worry that like the founder that took his vacation for the first time, then overcorrected, we live in a society where we’ve forgotten that we’re human. That we need breaks. That we need sleep. And that we can’t do most things alone, including building ambitious ideas and maturing as professionals.
#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.
Howard Lindzon has over 20 years of experience in both public and private market investing. He previously founded and managed the hedge fund Lindzon Capital, and is currently the founder and General Partner of the early-stage venture capital firm Social Leverage. Through Social Leverage, he and his partners have been seed investors in startups like Robinhood, Beehiiv, and Manscaped to name a few. Howard was the founder of Wallstrip (acquired by CBS), and is the the co-founder and Chairman of Stocktwits, the leading social platform for traders and investors. Throughout his career, Howard has strongly advocated for and helped drive the decentralization and democratization of investing. He resides in Phoenix, AZ and Coronado, California.
[00:00] Intro [01:51] Howard’s biggest misses as a startup investor [06:21] What happens when you trust a single reference too much in the diligence process? [10:24] What kind of company does Howard think Carta should be? [14:52] Howard’s two beliefs on selling positions [24:29] What types of fund managers did Howard invest in as an individual LP? [30:46] How did Howard write a $150K LP check in Multicoin [36:06] Why Howard likes GPs who struggle to fundraise [41:16] How Howard raised his fund of funds [44:19] Howard’s LP investment thesis [47:16] How much of investing is luck vs skill? [51:57] Reframing curiosity and risk [57:37] Market risk vs execution risk in your career [59:18] Howard’s advice to young professionals [1:03:40] A founder or GP’s first interactions with Social Leverage [1:08:25] Does succession planning matter to Social Leverage? [1:10:16] The big lesson about follow-on financing from Social Leverage’s Fund I [1:14:49] Thank you to Alchemist Accelerator for sponsoring! [1:17:25] Legal disclaimer
“You can’t be a good investor if you haven’t been in there and go ‘Ahhh, that was a dumb idea.’”
“Sell when you can, not when you have to.”
“They gave me money because I’m weird. They gave me money because they trusted me, but they also know that I’m weird. Therefore, if I start to think like them, we’re all screwed. So I have to think like me.”
“If you’re curious, it’s pretty hard not to stand out over time.”
