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An Individual LP’s Guide to Investing Like an Institution | Samir Kaji | Superclusters | S1E8

Samir Kaji is the CEO and Co-Founder of Allocate, a private markets technology company that pairs origination with portfolio management tools to allow investors to efficiently construct and manage their alternatives portfolios. 

Prior to Allocate, Samir spent 22 years in venture banking between SVB and First Republic Bank and closely worked with and advised over 700 venture capital and private equity firms. During this time, he completed over $12B in structured debt transactions and has invested personally in over 75 funds and companies, including early-stage investments into Carta (seed), Side (seed), PolicyGenius (Series A), and FanDuel (Series B) as well as Growth investments into Reddit, Alto Pharmacy, and Carbon Health. He has also invested in over 40 funds across various investment types.

Samir completed a finance undergraduate degree at San Jose State University, a finance MBA from Santa Clara University, and completed the prestigious Kauffman Fellows venture program in 2017. Samir is also the host of Venture Unlocked, a top venture capital podcast available on Itunes, Spotify, and Substack.

You can find Samir on his socials here:
Twitter: https://twitter.com/Samirkaji
LinkedIn: https://www.linkedin.com/in/samirkaji/

And huge thanks to this episode’s sponsor, Alchemist Accelerator: https://alchemistaccelerator.com/superclusters

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[04:15] What will be the biggest change in the next decade for the LP universe?
[08:45] Portfolio allocation for emerging LPs
[12:32] How has Samir’s LP investment strategy evolved over the years?
[16:04] Why Samir invested in Bullpen Capital’s Fund I
[17:43] GP-business model fit
[19:40] GP red flags
[21:00] The one question Samir asks to see if GPs understand how to do portfolio math
[23:31] The art of asking good questions
[29:44] What is the Minimum Viable Fund?
[36:14] How to pick 10 funds out of 4000 VC funds
[42:19] How did Samir pitch Allocate to his investors?
[48:11] The first hires at Allocate
[50:53] How Samir defines work-life integration
[56:38] The first two emerging fund managers Samir backed at First Republic Bank
[59:41] The lesson Samir’s father shared with him when he thought about leaving SVB
[1:02:41] What happens when you overanalyze
[1:07:27] Thank you to Alchemist Accelerator for sponsoring!
[1:10:02] If you liked it, give us a like or share!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“When you think about investing in any fund, you’re really looking at three main components.

  1. It’s sourcing ability. Are you seeing the deals that fit within whatever business model you’re executing on?
  2. Do you have some acumen for picking?
  3. And then, the third is: what is your ability to win? Have you proven your ability to win, get into really interesting deals that might’ve been either oversubscribed or hard to get into? Were you able to do your pro rata into the next round because you added value?

“And we also look through the lens of: Does this person have some asymmetric edge on at least two of those three things?”

“When you’re investing in a fund, especially when you’re making an ex ante decision, meaning you’re not buying a secondary, you’re actually just looking at what’s the probability of success in the future. You want to focus on process, more than just outcomes in the past. The process is how they think.”

Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP
Follow Superclusters on TikTok: https://www.tiktok.com/@super.clusters
Follow Superclusters on Instagram: https://instagram.com/super.clusters

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The Job Description of a Great Founder

night, sky, search

As people were coming back from the holidays, I had the chance to catch up with two friends earlier this week on two different occasions. One who built a company hundreds strong. The other is someone who’s seen the rise and fall of civilization again and again.

The former told me, “The greatest litmus test of a leader is their ability to train another leader.”

The latter told me something they had learned from a successful founder. “I lift as I climb.”

Both equally as profound. But to take it one at a time…

To train another

I’ve mentioned on this blog before that A-players hire A-players. And that B-players hire C-players. C’s hire D-players. And so on. A-players can tolerate working with B’s, but not C’s and D’s. So at the end of the day, the A’s leave, and all you’re left with are B’s and below.

While that statement makes sense in broad strokes, the truth is from an investor’s perspective — hell, just an outsider’s perspective — no one knows if you’re an A-player or not at first glance. Or at least it’s really hard to tell. Maybe there are people who are smarter than me out there who can tell at a glance. At the end of the day, seeing others execute is a great way to tell, but that takes more than one meeting usually.

And sometimes the easiest way to see is in doing reference checks. Seeing who else is on the team that they hired and trained. Seeing who they hired in previous roles. And if those other folks they’ve trained have gone to do amazing things, that’s usually a good sign that the person in question knows what an A-player looks like. And if it’s consistent enough, knows how to mint stellar leaders.

I lift as I climb

One of the greatest red flags I often see are founders hiring experienced (often expensive and brand-name) executives, sales reps, and product managers super-early in the startup lifecycle. Especially before product market fit. And often the biggest expectation for these early hires is to do:

  1. What they themselves couldn’t do
  2. And/or what they themselves don’t want to do

Both happen to be cardinal sins at the early stage. Why does the above matter?

Because if you’ve never done the job yourself, specifically building/managing the product and getting to your first customers:

  1. You don’t know how to set realistic targets and benchmarks for that role
  2. Given how crucial early customer feedback is to the product and the company, you’ll miss out on key customer insights if you’re not in the trenches yourself.

The goal of the afore-mentioned early hires is to refine your playbook, not build the playbook from scratch. And if that doesn’t appeal to you as the founder, then you might not be ready to be one.

And this is the exact reason I love the line “I lift as I climb.” For every time you figure something out, an inflection point for the company, a key customer discovery/insight, a sales script that closes twice as well as the last one, your rising tide raises all boats. But you cannot lift if you don’t climb first.

In closing

For those of you tuning in from the video and audio universes, you know I’ve been thinking a lot about succession planning as of late. Largely motivated by my conversations with Ben from Next Legacy.

And Courtney from Recast.

So naturally, when I was catching up with both of my friends, their words found refuge in the questions I was seeking answers to.

And when all’s said and done, what I look for in a founder who’ll create a multi-generational company is the same in what I look for in an emerging manager who’s planning to build a multi-fund firm. And in a way, what a young professional might look at when betting their career on a startup.

Photo by Vincent Chin 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!

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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How Being Weird is a Deal Flow Superpower | Howard Lindzon | Superclusters | S1E7

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.

You can find Howard on his socials here:
Twitter: https://twitter.com/howardlindzon
LinkedIn: https://www.linkedin.com/in/howardlindzon/

And huge thanks to this episode’s sponsor, Alchemist Accelerator: https://alchemistaccelerator.com/superclusters

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[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

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“We’re in the business of swinging.”

“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.”

Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP
Follow Superclusters on TikTok: https://www.tiktok.com/@super.clusters
Follow Superclusters on Instagram: https://instagram.com/super.clusters

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2023 Year in Review

Our tiny blue marble has spun yet another lap around its closest star. From a job change to starting a podcast, between visiting Japan for the first time (and holy frick is Japan amazing!) and blacksmithing my own santoku chef knife while I was there, and from building the most unlikely friendships that will last for decades to come to realizing life rarely goes according to plan — a good reminder of Mike Tyson’s line: “Everybody has a plan until they get punches in the face.” — and from attempting to convey my year in one sentence to realizing this is the longest run-on sentence I’ve written on my blog to date, it’s been a great year.

While I wasn’t aware of this till recently — courtesy of doom-scrolling on Instagram, this year’s been a year where I’ve “used the difficulty.” To echo the amazing Sir Michael Caine. For those unfamiliar with the phrase, I highly recommend listening to the full 2002 interview, but at least this.

In short, you can’t always control the situation you’ve been given, but you can control how you react to it. If you want your life to play out like a comedy. If you want it play out as a drama. Or if you want it to play out like a feel-good movie. Use the difficulty to your advantage and act accordingly.

By the numbers

Interestingly enough, despite writing whatever I find fascinating on a weekly basis — in other words, not optimized for search engines — just under half of my blog’s views come from search engines. Primarily, and I mean 95% of which from Google. Followed by LinkedIn (which accounts about a third of my views) then Twitter (~7%).

As many other aspects of life, the viewership of my blogposts also have a Pareto distribution, where they seemingly follow the power law. With my top blogpost winning more than twice the views of the second highest. And the second highest with double the audience of the third highest, before the views plateau out across all the rest of my essays. Even for this year alone, my most popular blogpost is eight times more popular than my second most popular.

And every week I feel honored that I have readers like you who tune in to my weekly musings and our family has only grown since.

Something I’ve noticed when looking at the numbers is that I seem to have the most readers arrive at this humble piece of virtual real estate every October, barring 2021. And I wonder if it’s a function of the market’s interest crests then or that I just happen to write better pieces around then.

In addition I’ve started measuring my habits since October, only to realize, holy hell, I am inconsistent with them. While I’d love to blame travel and work, the simple truth is it’s hard to manage what I didn’t measure before. Hopefully in 2024, we’ll see a lot more consistency.

P.S. the last day, aka today, is down, since the day’s just started and I haven’t logged in anything yet. And for those curious, I’m tracking this all on a Notion dashboard.

But my favorite thing that I started measuring, is that little trophy icon in the first column of the “Evening” section. And that little trophy stands for: “Was today truly worth it?” Defined by me learning a new skill. Gaining a brand new insight about the world. Or created a core memory. And I’m happy to say that that box gets checked about two times per week. 🙂

Post publish edit: The last icon is often how I take a cold dunk/shower, as opposed to a hot one. Having friends, former housemates, and my partner exclaim and tell me “I know you shower more often than that” made me realize that icons don’t do some things justice.

2023’s Most Popular

  1. The Science of Selling – Early DPI Benchmarks — One of my favorite lines from Jerry Colonna’s book Reboot is: “It’s buy low, sell high. Not buy lowest, sell highest.” In the world of VC, we spend a lot of time talking about when to buy, how to buy, and who to invest in. But rarely about the other side of the playbook, selling. Or exiting positions. And while different investors have shared the what behind selling — in other words, the exact percentage they sold at, how much they sold when they could — this blogpost was one of the first, and maybe first (who knows), to explore the why and how behind selling positions in portfolio companies as a private investor.
  2. The Non-Obvious Emerging LP Playbook — The blogpost that set me down the path I am now on. To explore how I can help the next generation of capital allocators is investing into the innovation economy. Simply put, the emerging LPs.
  3. Five Tactical Lessons After Hosting 100+ Fireside Chats — In fairness, had no idea this blogpost was going to do as well as it did. And luckily, I am now able to stress-test and get better at asking questions and hosting interviews through not only what I continue to do in the world of venture, but also through my new podcast, Superclusters. Where you’ll see some of my learnings above in action.
  4. 10 Letters of Thanks to 10 People who Changed my Life — In all honesty, it still befuddles me to this day how this blogpost consistently ranks this high. I don’t namedrop here, and I don’t use any clever SEO techniques, yet every day this blogpost seems to find organic interest. Nevertheless, I’m glad it has. And if it empowers people to be more grateful to the people around them, I’ll have done my job. There’s also a deficit of content and knowledge here for sure, but I’m still trying to figure out what that something is.
  5. How to Think about LP Construction — Not all LPs are created equal. It’s something I’ve known for a while. Both in conversation with other LPs and GPs, but also in learning of the different types of motivations to be an LP. For some, VC is an access class, not an asset class. For others, it’s the exact opposite. The latter is more likely to be a large institution. Nevertheless, that’s one example of many. And it was incredibly rewarding to hear GPs I really respect share what they’ve learned across multiple funds.

All-Time Most Popular

  1. The Science of Selling – Early DPI Benchmarks — Turns out you all love tactical frameworks, so my goal is to share a lot more with you in 2024. I have a couple in the works as we speak (or as I write this).
  2. The Non-Obvious Emerging LP Playbook — Stay tuned for more content on this front!
  3. 10 Letters of Thanks to 10 People who Changed my Life — If anything, I hope this inspires people to write one note or letter or record a voice note of thanks to someone who’s helped you become the person you are today.
  4. 99 Pieces of Unsolicited, (Possibly) Ungooglable Startup Advice — Don’t worry already in works of many more iterations of this. And while I can’t promise when the next one will come out since it’s I’m really only including what I think are the best pieces and most tactical pieces of advice, I will say it’s a matter of when not if. I’m 20 in for the founder one. And 12 in for the investor one.
  5. Five Tactical Lessons After Hosting 100+ Fireside Chats — I’ve a feeling this one won’t age well, but hell, maybe it ends up being like the #3 spot on giving thanks. Time will tell.
  6. How to Pitch VCs Without Ever Having to Send the Pitch Deck — Back in 2021, I knew that this blogpost was going to hold an evergreen spot up here. And I’m pretty sure it’ll flirt around here even longer. While it’s only been two years since, and while there’s also a mountain of public resources on how to pitch, strangely, most people still struggle to connect to the people they want to. And it’s true for both founders and VCs. Ya, the latter seems ironic, until you see that founders are pitch judges, juries and executioners as well. For them, from talent. Until you also see that our parents are often the harshest critics of our decisions. Yet some have no experience working in the world in which we do. All that to say, oftentimes it’s easier being the judge than the judged. I can’t claim much of the insight here as original, but rather have to thank the fact I have really smart friends. Smarter than me at least. The flip side to the wild performance of this essay may just be one of the closest titles I have to being clickbait-y.

2023’s Most Memorable

In all honesty, the most memorable each year to me were ones where I was scratching my own itch. Some, by the numbers, perform better than others. But for me, each of the below represent the greatest delta in either knowledge acquisition or insight development. Of course, not mutually exclusive to each other.

  • The Science of Re-upping — I enjoyed writing this one in particular not only because I got to work with Arkady and Dave on this — two minds I greatly admire, but it also became the perfect opportunity to learn more about the world of professional sports beyond the players and scores themselves. Two birds with one stone. I’ve always admired folks who are able to pull from various, seemingly disparate topics and analogize them to venture. And while I still have many more miles on my odometer to go, this was one of the amazing opportunities to take a stab at marrying two different worlds through stories.
  • How to Think about LP Construction — I will admittedly take any opportunity I can to talk to my favorite people. And this was another one of them. That said, to get them all in the same metaphoric room to talk about the same topic, where the energy of one inspired another, now that’s something special. Funnily enough I did the vast majority of these interviews for this blogpost asynchronously, but upon sharing the final product with the group the week before publication, there was an incredible amount of energy (gratitude, stand up comedy routines, and so on) in the group. And all this was over email.
  • The Science of Selling – Early DPI Benchmarks — This, in many ways, was an accidental piece. Not only did it come up in conversation over Friday brunch quite randomly (serendipity at its finest), it also took, at least compared to the above two, the least amount of time to write. The first draft was ready in about an hour. And including all the edits, it came out to about two hours of work. It’s a gentle reminder that sometimes your best pieces are the easiest to write.
  • My Ever-Evolving Personal CRM — I wrote this blogpost after some coercion from a small group of friends who’ve been fascinated by how I stay in touch with people. And when they saw how I did it on Airtable, they asked if I would sell them my template (not that I had one at the time). Nor am I selling now. But nevertheless, the web of what we do, who we talk to, who we grow with, and why we do things is increasingly complicated and so far, there hasn’t been a great product out there that tracks this (and yes, I’ve used all the CRM tools out there). And so I created my own.
  • #unfiltered #83 There Doesn’t Have to be a First Place — I really enjoyed writing this one. Inspired by a podcast appearance by Simon Coronel, I learned that in the world of magic competitions, first place isn’t always granted. If the judges feel like a magic act isn’t on par with previous years, even if it is the best one that competition, they choose not to award a first place. Similarly, I think the world in a lot of ways has lost itself in the noise. That our definition for quality has fallen in the past decade. And I’m sure the older generations will harken back further. But I do believe a heuristic like this keeps us honest and that as a society, we move forward together, not just optimizing for short-term maximizations.
  • #unfiltered #78 The Gravitational Force of Accumulated Knowledge — Another fun piece to write about the power of how knowledge compounds. Not only in isolation, but also collectively. While that is a rather obvious fact, I loved the reframing of how to look at it from Seth Godin and Bill Gurley’s public interviews.
  • How to Retain Talent When You Don’t Have the Cash — One of the biggest lessons I learned at On Deck was that the team was amazing — in fact, world-class — at acquiring the best talent, but was shy on retaining the world’s best talent. To this day, I believe I have never worked in a higher concentration of brilliant talent than I did when I was at On Deck. And this blogpost is an homage to my former team, how brilliant they were, but also the lessons we took away from that experience.
  • 7 Lessons from My Time at On Deck — And in the theme of On Deck, and how much I treasure the people I work with and the experience I had while I was there, last but not least, the culmination of lessons I took away from an 18-month period that I would never trade for any other experience.

And I started a podcast. Superclusters. (Or here’s on Spotify or Apple Podcasts if you prefer). It’s still too early to tell how Season 1 will do, with only six episodes in (the most recent of which here). But by next year, I should have more than enough to share about my learnings here. But early data seems to suggest that people love true stories more than they do tactics.

Until the next, stay awesome! And see y’all in the new year!

Photo by Polina Kuzovkova 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!

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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How to Build a Multi-Fund VC Firm | Ben Choi | Superclusters | S1E6

Ben Choi manages over $3B investments with many of the world’s premier venture capital firms as well as directly in early stage startups. He brings to Next Legacy a distinguished track record spanning over two decades founding and investing in early-stage technology businesses. Ben’s love for technology products formed the basis for his successful venture track record, including early stage investments in Marketo (acquired for $4.75B) and CourseHero (last valued at $3.6B). He previously ran product for Adobe’s Creative Cloud offerings and founded CoffeeTable, where he raised venture capital financing, built a team, and ultimately sold the company.

Ben is an engaged member of the Society of Kauffman Fellows and has been named to the Board of Directors for the San Francisco Chinese Culture Center and Children’s Health Council. Ben studied Computer Science at Harvard University before Mark Zuckerberg made it cool and received his MBA from Columbia Business School. Born in Peoria, raised in San Francisco, and educated in Cambridge, Ben now lives in Palo Alto with his wife, Lydia, and three very active sons.

You can find Ben on his socials here:
Twitter: https://twitter.com/benjichoi
LinkedIn: https://www.linkedin.com/in/bchoi/

And huge thanks to this episode’s sponsor, Alchemist Accelerator: https://alchemistaccelerator.com/superclusters

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[02:44] Ben’s childhood
[07:54] What is Ben’s superpower?
[16:58] What aspect of being a VC do most founders fail to appreciate?
[18:46] What do GPs fail to appreciate about LPs?
[21:24] The similarities between VC and the intelligence industry
[24:00] What’s changed about being a VC since 2006?
[27:14] How does Ben tell signal from noise?
[32:46] Past track record portability
[37:24] A case study on how a syndicate investor became a lead investor
[41:00] Ben and David nerd out about free T-shirts
[44:26] An example of how a GP convinced Ben to invest in their fund
[47:53] Succession planning in a VC firm
[56:51] How Legacy Venture started
[1:01:28] Next Play + Legacy Venture = Next Legacy
[1:04:05] Which non-profits do the carry go to?
[1:05:48] What kind of GP impresses Ben?
[1:07:58] Ben’s biggest professional lesson in 1998
[1:12:56] Thank you to Alchemist Accelerator for sponsoring!
[1:15:32] Legal disclaimer

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“The integrity of information. Does this actually stand on its own not because someone said so, but because the mechanics behind it make sense. Does this have internal integrity to it?”

“If you see a thread and you pull it, does it come out as a single piece of thread? There’s no integrity right there. If you pull it and the whole fabric starts to warp–… if you pull it and other pieces start to move, there are connections. That thread is actually holding this together.”

Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP
Follow Superclusters on TikTok: https://www.tiktok.com/@super.clusters
Follow Superclusters on Instagram: https://instagram.com/super.clusters

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Big If True

baby

I wrote a blogpost last year, where I went a level deeper into my NTY thesis. In short, in what situations and in front of what kind of ideas do I ask founders: Why now? Why this? And why you?

Plausible IdeaWhy this?
Possible IdeaWhy now?
Preposterous IdeaWhy you?
For the deeper dive, check out this blogpost.

But let’s go a step deeper. As I’m writing another blogpost slated to come out next year, I’ve had the chance to sit down with some amazing multi-cycle investors. And a common thread across all those conversations has been that they chose to be the first check in companies that would be big, if true.

Which got me thinking…

If ‘big if true’ is for the preposterous ideas out there, then possible ideas would be ‘big when true.’ And plausible ideas would be ‘big AND true.’

Let’s break it down.

Big AND true

Not too long ago, the amazing Chris Douvos shared with me that the prerequisite to being “right and alone”, where fortune and glory lie, is to be “wrong and alone.”

Imagine a two-by-two matrix. On one axis, right and wrong. On the other axis, alone and in the crowd. You obviously don’t want to be wrong and in the crowd. But you do want to be in the right and alone quadrant. Because that’s where fortune and glory are at. Most people think that to get there, you must first start in the right and in the crowd quadrant. But it’s important to note, that once you’re in the crowd, and you get the dopamine hits of validation, it’s really hard to stray away from the crowd. So really, the only way to get to fortune and glory is to be wrong and alone. To be willing to go against the grain.

Unfortunately, for big AND true, you’re in the crowd. And while you can usually make money on the margins, it’s hard to be world-defining. ‘Cause you’re too late.

The thing to be wary of here if it is any investor’s strategy to deploy capital here is to not be the last money in. Hype and compounding are dangerous. And for many companies that exist here, they have a short half life. If you’re the last one holding the bag, that’s it.

Big WHEN true

You know that saying, “It’s a matter of when, not if…” it’s just as true in the innovation space. There are some things in life that are bound to happen. Recessions. Hype cycles. Rain. First snowfall. Summer heat. Progress. Maturity. When one’s baby teeth fall out. Wrinkles. Gray hair. Some with more predictability than others.

These ideas are defined as those with early commercial traction, likely with a niche audience or only your 1000 true fans. And that’s okay. Usually happens to be some of the toughest pre-seed and seed rounds to raise. There’s clearly traction, but no clear sense of rocket ship growth.

Timing matters. Is the larger market ready to adopt the beliefs and culture and habits of the few?

For some investors, it’s why they target quality of life improvements to the wealthy made ready for the masses. Living a wealthy lifestyle is, after all, aspirational for many. On the flip side, if you have a niche audience and are looking to expand, are there underlying beliefs and traits that the broader market has but has instead applied those beliefs and habits in other parts of their life?

Big IF true

Sam Altman put out a blogpost just yesterday, titled “What I Wish Someone Had Told Me.” And out of the 17 lessons he shares, one in particular resonated the most with me:

“It is easier for a team to do a hard thing that really matters than to do an easy thing that doesn’t really matter; audacious ideas motivate people.”

While the stories of Airbnb or Coinbase or Canva seem to suggest that these are nigh impossible ideas to raise on, anecdotally, I seem to find that the most transcendent companies with CEOs who are able to acquire world-class talent to their companies have less trouble fundraising than the ‘big when true’ ideas. But more difficulty raising than the ‘big and true’ ideas.

That said, instead of many smaller checks, you just need to find one big believer. In other words, the Garry Tan for your Coinbase or the Fred Wilson for your Twitter. One way to look at it, though not the only way, is what Paul Graham puts as the “reasonable domain expert proposing something that sounds wrong.” Crazy, but reasonable. Simply, why you?

Photo by Jill Sauve 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!

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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S1E5: Courtney McCrea

Courtney Russell McCrea enjoys over 30 years of venture capital and private equity investment experience including 13 years of fund investing and 18 years of direct principal investing.

Courtney is Co-Founder and Managing Partner of Recast Capital, a 100% women-owned platform investing in and supporting emerging managers in venture, with a focus on diverse partnerships.

Prior to co-founding Recast, Courtney was a Managing Director of Weathergage Capital, a boutique fund of funds that provided its clients with access to premier venture capital, growth equity and micro-VC partnerships. Venture fund commitments included both brand name funds and emerging managers. In addition to fund investment responsibilities, Courtney led the direct co investing program at Weathergage. During her 10 year tenure at Weathergage, Courtney made commitments to 100 funds and seven direct co-investments.

Prior to Weathergage, Courtney was a General Partner with Weston Presidio, a leading diversified private equity firm based in San Francisco. After 7 years at Weston Presidio, she left in 2004 and founded Silver Partners, a private equity advisory firm where she evaluated secondary and co-investment opportunities and advised consumer growth businesses. Courtney was also a Director at Sterling Stamos, where she managed investments in buyout funds, venture capital funds and hedge funds.

Earlier in her career, Courtney made equity co-investments as an Assistant Vice President at PPM America. She also spent 5 years at GE Capital where she worked on private equity, senior and subordinated debt investing.

Courtney has an M.B.A., with honors, from the Kellogg Graduate School of Management and a B.A. in Economics from the University of Illinois, Champaign-Urbana. She is a member of the Kauffman Fellows Class 3.

Courtney is a member of the NVCA Forward Board of Directors and the Alzheimer’s Association Northern California and Nevada Board of Directors.

You can find Courtney on her socials here:
Twitter: https://twitter.com/courtneyrmccrea
LinkedIn: https://www.linkedin.com/in/courtneymccrea

And huge thanks to this episode’s sponsor, Alchemist Accelerator: https://alchemistaccelerator.com/superclusters

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[02:37] What of Courtney’s past helped her co-found Recast Capital
[04:02] Three reasons to invest in emerging managers
[05:17] What does “institutional quality of emerging managers” mean?
[06:52] How to diligence emerging managers
[10:30] How to do reference checks on GPs
[14:40] How has being a Kauffman fellow helped Courtney build Recast’s Enablement and Accelerate programs
[19:51] How do alumni GP stay active in Recast Capital’s community
[20:59] Zoom vs. in-person education for GPs
[23:00] What kind of managers do Recast Capital invest in versus who ends up joining the Enablement Program versus who joins the Accelerate program
[28:33] Why are the Enablement Program and Accelerate program free
[30:25] Spinouts from larger funds
[32:12] What are emerging manager red flags?
[34:03] Should emerging managers have answers to questions on succession planning?
[36:00] Challenging the 1% GP commit: How much should different archetypes of GPs commit to their own fund?
[40:52] Lessons from arguments between GPs
[46:30] Getting Courtney to say yes
[47:46] Courtney may make some enemies with this statement!
[48:54] Thank you to Alchemist Accelerator for sponsoring!
[51:30] Legal disclaimer

SELECT LINKS FROM THIS EPISODE:

Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP
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How to Make People Feel Special at Events

gift, present, christmas, happy, holiday

Guilty as charged, but I was doom-scrolling on Instagram recently and I came across a reel where two Formula 1 drivers were asked to guess the race track given only a racecar’s engine’s audio (vroom vroom). And to my absolute amazement, the two were able to guess track after track. Some answers seemed to have only taken them a few seconds to figure out.

The Instagram reel came from this YouTube video for those who are curious.

So I couldn’t help but notice, how well they knew each track. That they had taken special notice to all the small bumps in the road. The turns. How long each turn was. All of it, without any visuals. It’s for the same reason I am always impressed every time Bon Appetit’s Chris Morocco can recreate dishes by taste, smell and feel alone (no sight, he’s blindfolded). A lot of which is in line with the post I wrote last week. It’s not just about paying attention, but how to pay proper attention.

So this time around, I thought why don’t I bring this into the world of events. Something I’m deeply passionate about.

Experiences > Events

“Jonathan Yaffe, co-founder of the experience management platform, AnyRoad, defines an experience as something that stimulates at least three senses.”

I first read that line on page 146 in my buddy Lloyed’s book on community-building. And it made total frickin’ sense. Lloyed went on to write that Zoom sessions don’t count as experiences because it only engages one’s sight and sound. But events like Dining in the Dark, which my friend hosts, do count. Despite taking away sight, you’re tapping into taste, smell, and sound. The last of which occurs when there’s a band playing in the background, but with each course, a new instrument is added into the mix. And it’s because of experiences like these, they leave such strong impressions. Emotional impressions. Nostalgia.

Emotions, after all, are multi-sensory. And eliciting those emotions require you to fully commit. The question is how.

How to make people feel special at events

One of my favorite lessons I picked up during my time at On Deck was from Sam Huleatt. A strike is better than a spare. We were hosting sessions and events three to six times a month, depending on the time of the year. And Sam proposed that we go through an exercise. A thought experiment.

  1. What if we only did one event per month? If so, what would that look like?
  2. What if we only did one every quarter?
  3. And what if we only did one every year?

How does that change the way we think about events? What changes at each stage?

Honestly, one of my favorite exercises to go through when I feel compelled to hit a certain quantity and realize I have to find the optimal point between quantity and quality.

But since then, that inspired another set of thought exercises I do.

  1. If I had to host an event for just one person — just one — what would I do to make it an unforgettable experience?
  2. What would need to change if I did so for a four-person dinner?
  3. A six-person dinner?
  4. What about a 10-person event?
  5. What about for 50 people?
  6. For 100?
  7. For 1000?

And so on.

At some point, usually around 50 is when things start hitting scale. But let me break down why each of the above before 50 are inflection points:

  • 1 person. This person is your universe. You can’t make it any more tailored and personalized than this. It’s a date.
  • 4 people. For the most part, still only one conversation happens at a time, but now as the host, you have to make sure no one is left out.
  • 6 people. In my mind, this is the minimum number of people for more than one conversation to be happening at once. For the first time, you have to worry about flow of the event while you’re not capable of being present everywhere all at once.
  • 10 people. You not have more than two conversations going on. Juggling with two is easy; for some, that may not really be juggling. But once you’ve added a third and a fourth ball, then this is real juggling. Here, the host has to think not only about the number of conversations, but to pay attention to folks who become satellites to conversations. Watching for people who are distracted. Uncomfortable. On their phone. And so on. But also, when conversations go too long. As the host, finding ways for people to enter and exit conversations easily is vital. It’s better to have less time than to have too much time.
  • And 50 people. For the first time, you need to think about having more than one host. You can only scale your time and attention so much. So now you’re training a team to be as attentive, if not more, than you are.

The larger the event, one can say the more polyamorous you have to be. You have to deeply care for each person. And while everyone at your event likely knows you’re “dating” everyone else, if you can still make them feel special — like the most important person in the world, that their time is valued, their attention is valued, and their presence, mind and insights even more so — then you’ll have done something 99.9% of event hosts have not been able to do. Frankly, probably would rather not do. ‘Cause, at least if you start small, it’s not crazy work. It’s quite easy, just requires more effort than most are willing to give.

Other times, event hosts just scale their events too quickly. And hit scale before they find their magic. So, if you can, do unscalable things before you hit scale.

Notice when in a conversation someone’s eyes divert. Notice when they ask to leave to use the restroom. And notice when people lean in to a conversation, as opposed to lean back. Just like a racecar driver notices how many seconds a turn is, when there’s an indent in the road, when the brakes are glazed and the tires need to warm up without having to look at them.

Photo by Kira auf der Heide 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!

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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S1E4: Jamie Rhode

Jamie Rhode is Principal at Verdis Investment Management, focused on venture capital, private equity and hedge fund investment sourcing and due diligence.

She joined Verdis from Bloomberg, where she held roles in both equity research and credit analysis. There, she created, managed and leveraged an extensive library of statutory and financial and market data for buy and sell-side clients that use Bloomberg to make investment decisions.

A licensed Chartered Financial Analyst, she earned her bachelor’s degree in Finance and Marketing from Drexel University’s College of Business Administration.

You can find Jamie on her socials here:
Twitter: https://twitter.com/DurationFX
LinkedIn: https://www.linkedin.com/in/jerrcfa/

And huge thanks to this episode’s sponsor, Alchemist Accelerator: https://alchemistaccelerator.com/superclusters

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

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[04:27] What skills did Jamie acquire while working at Bloomberg
[08:45] What inspired Jamie to go into equity research
[11:55] Verdis’ original allocation model
[13:27] How Verdis first built their deal flow in 2016
[15:26] What Jamie likes in a cold email
[16:41] What kind of cold email to VCs won Verdis an 80% response rate?
[20:27] Verdis’ inbound vs outbound deal flow over the years
[22:34] Why Verdis’ mandate is to invest in diversified portfolios as opposed to concentrated portfolios
[27:50] The downsides of early distributions
[32:12] The benefits of early distributions
[36:01] Luck versus skill
[40:15] Why does Verdis measure “outliers” as opposed to unicorns
[44:37] The relationship between proprietary deal flow and portfolio allocation models
[45:55] How does Verdis decide which portfolio funds get re-ups
[48:52] Why GPs shouldn’t conform their strategies to LPs’ mandates
[51:08] Why LPs should also have consistent strategies
[53:28] Why Verdis invests a third of their fund in funds based in Los Angeles
[58:50] A case study on what happens when you skip a step in the due diligence process
[1:02:57] The two things a GP can do to win Jamie over
[1:05:32] When does Verdis like to receive their tax documents from GPs?
[1:08:46] Thank you to Alchemist Accelerator for sponsoring
[1:11:23] Legal disclaimer

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Diversified managers have struggled a lot more to raise capital than more concentrated managers. I think it’s a little bit of a contrarian approach.”

“That venture capital bucket is the compounding machine for the family. We don’t look to that bucket for liquidity.”

“If you’re compounding at 25% for 12 years, that turns into a 14.9X.If you’re compounding at 14%, that’s a 5. And public market which is 11% gets you a 3.5X.”

“90% of your overall return comes from asset allocation, not individual investments.”

“If that asset is compounding at 20%, still the last 20% of time produces 40% of your return.”

“Outliers don’t truly emerge until 8-10 years after the investment.”

“If you provide me exposure to the exact same pool of startups [as] another GP of mine, then unfortunately, you don’t have proprietary deal flow for me. You don’t enhance my network diversification.”

Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP
Follow Superclusters on TikTok: https://www.tiktok.com/@super.clusters
Follow Superclusters on Instagram: https://instagram.com/super.clusters

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Paying Attention Vs Paying Proper Attention

magnifying glass, pay attention

Earlier this week, I was listening to a fascinatingly thoughtful conversation between Tim Ferriss and Kindred’s Steve Jang, where Tim said one line that stood out in particular: “I’ve been paying a lot of attention, but I’ll be honest, I don’t know how to pay proper attention.”

And well, it got me thinking. About the difference between knowing what to look at and knowing how to look at it.

One of my favorite TED talks is by Will Guidara (quite honestly I think it deserves more views on YouTube than it has). Will is probably best known for co-founding one of New York’s hottest fine dining restaurants, Eleven Madison Park, and for writing the book, Unreasonable Hospitality. And in it, he talks about how just listening to the conversations that are happening at the tables and delivering these small, unexpected pockets of joy can create experiences that transcend money and time.

In the afore-mentioned talk, he talks about how there are four diners at Eleven Madison Park. That they went to all the top restaurants in NYC. Le Bernardin. Per se. And so on. And Eleven Madison Park was the last on their to-do list. But the only regret they had was that they never got to try a New York hot dog. Of course, upon hearing that, Will storms out the door to buy a $2 dog, brings it back to the kitchen and convinces the chef to serve it over the aged duck that took years to perfect. And when he finally delivered the next course on the menu as the hot dog he just bought, the four guests went bonkers. That despite on the multiple courses and the brilliant food, that their favorite dish was the NYC hot dog.

That it was because Will paid proper attention to his guests that he was able to deliver a truly unforgettable experience.

The truth is how to pay proper attention to anything that deserves our attention is the million-dollar question.

Paying proper attention

There’s the famous selective attention test, where viewers are asked to count the number of times the ball is being passed between the players, only to fail to realize that there is gorilla that walks across the screen. We’re told to pay attention to the ball passes, but only by paying proper attention to the purpose of why the test is being administered, do we catch what is hiding in plain sight.

Similarly, Raymond Joseph Teller (or better known for being half of the dynamic magic duo Penn & Teller) did a fascinating talk a decade and a half ago about the illusion of expectation. That magic in all of its novel facets feeds off of the expectations of its onlookers. When one tries to pay attention to the coins that are “magically” jumping from one hand to the next, you might fail to catch the sleight of hand in between. But only after he reveals his secrets is the simple magic act all the more impressive. In other words, in the second half, he teaches you how to pay proper attention.

If you have eight minutes in your day, would highly recommend watching the below video.

I can’t speak for every topic, industry, relationship, and so on out there, but at least for the cottage industry of venture capital, why I choose to write an angel or an LP check is similar. I don’t really look for what will change. ‘Cause damn, it’s so hard to predict what will change and how things will change. If I knew, and if one day, I know, please invest in my public markets fund, which will be the best performing fund of all time. But I don’t. We, as pundits sitting around the table, might draw predictions. But even the smartest of us (not sure why I say us, ’cause not sure if I can put myself in that category yet) would be lying if we knew what would happen in foresight.

Instead, I look at what doesn’t change.

What doesn’t change?

The great Charlie Munger passed away last week at the age of 99. And without question, a great loss to the world we live in today. Just half a year prior, he and Warren Buffett were hosting their 2023 annual meeting. And just two weeks prior, he was still doing CNBC interviews. And one of my favorite lines from that May annual meeting was:

“Well, it’s so simple to spend less than you earn, and invest shrewdly, and avoid toxic people and toxic activities, and try and keep learning all your life, et cetera, et cetera, and do a lot of deferred gratification because you prefer life that way. And if you do all those things, you are almost certain to succeed. If you don’t, you’re going to need a lot of luck. And you don’t want to need a lot of luck. You want to go into a game where you’re very likely to win without having any unusual luck.”

In reducing the requirement to need luck, one of the most effective ways to find what is constant in life. That despite changing times and technologies, these stay true. Or as Morgan Housel and Naval Ravikant put it, If you lived your life 1000 times, what would be true in 999 of them? In investing jargon, pattern recognition. Across my investments and more, where have I seen outperformance? What characteristics do they all share? What about human nature won’t change?

In fairness, pattern recognition gets a bad rap. And for a lot of investors, that’s because they choose to only invest in their comfort zone, and what they know best. Their former colleagues. Their Stanford GSB classmates. People who look like them, think like them, act like them. But recognizing thematic threads stretch across all facets of our life. We learn that not brushing our teeth well can lead to cavities. We learn that after stubbing our toe on the kitchen counter numerous times, we take a wider turn before turning into the kitchen. And we learn that eating piping hot foods kills your tastebuds for the next few days.

The venture corollary

In venture, we’re always taught to look at the team, product, and market. And that all are important. But if you tell a new grad or an ex-founder or an emerging angel to do just that. To them, that means nothing. They wouldn’t know how to judge. They have no benchmarks, nor do they know what’s right versus wrong. Now I don’t want to sound like a broken record, but I do believe previous blogposts like this and this are quite comprehensive for how I pay proper attention as an investor.

Emerging LPs are not immune to the lack of perspective as well. My hope and my goal is for how to be just as important if not more than the what. And for the why to be just as or more important than the how. It’s because of that, I write essays like this and this. And of course, it’s why I started Superclusters because I, too, am looking for how to pay proper attention to the next generation of venture investors. (Stay tuned for the coming Monday for episode four where we unpack the bull and bear case of early distributions in a fund!)

Photo by Shane Aldendorff 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!

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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