Five Short Links To Long Reads

A Ticket From Michael Jordan’s First NBA Game Auctions Big $$$, Adam Sandler Gets Respect (Finally!), and Why Germany’s Envy of Silicon Valley Helped Wirecard Commit Massive Fraud

Ok, just a roundup of some great recent reads.

stack of magazine and newspapers [DALL-E]

Adam Sandler doesn’t need your respect. But he’s getting it anyway. (Geoff Edgers, WaPo) — Rare sitdown with Adam Sandler featuring this great line from SNL creator Lorne Michaels

“The nature of comedy is you get the audience, you get the money,” says Michaels, SNL’s creator and executive producer. “Respect is the last thing you get.”

How a ticket from Michael Jordan’s Chicago Bulls debut became priceless. (Justin Heckert, ESPN) — Unripped ticket from Jordan’s first NBA game in 1984 finds its way to auction. But the story behind the owner is the most enjoyable part.

The ticket made him famous with his neighbors. They already liked Mike Cole anyway for his odd place in the equilibrium of the cul-de-sac, the tall, bald guy who waited too long to shovel his driveway when it snowed and then slipped on the ice while coming back from retrieving the mail.

The Dystopian Underworld of South Africa’s Illegal Gold Mines. (Kimon de Greef, New Yorker) — If this story doesn’t make you incredibly thankful for winning the birth lottery…..

When the country’s mining industry collapsed, a criminal economy grew in its place, with thousands of men climbing into some of the deepest shafts in the world, searching for leftover gold.

How One Guy’s Car Blog Became a $1 Billion Marketplace. (Ben Cohen, WSJ) — Bring a Trailer’s origin story.

A hybrid of Craigslist, eBay, Reddit and Sotheby’s that facilitated $1.37 billion in sales last year was not quite what Randy Nonnenberg had in mind when he started a car blog with a college buddy as a hobby.

How the Biggest Fraud in German History Unravelled. (Ben Taub, New Yorker) —Wirecard was a massive multibillion dollar fintech fraud. And at times it seems like German authorities were willing to look the other way, just out of hopeful pride that their country had finally launched a unicorn startup.

On February 18, 2019, Germany’s financial regulator, known as BaFin, issued a ban on creating new short bets against Wirecard, citing the company’s “importance for the economy.” “It was at that moment that they sided with criminals,” a German parliamentarian later said. The same day, prosecutors in Munich confirmed to a German newspaper that they had opened a criminal investigation. But they weren’t going after Wirecard — they were going after the F.T. [for an investigative takedown piece about Wirecard]


I Graduated Into The 2000 DotCom Crash, And It Was The Best Thing To Ever Happen To My Career

Why Lack of Easy Options Made Me Focus On Who I Wanted To Be, Which Paid Off Over Time

a very sad businessman holding a popped balloon, digital art [DALL-E]

In retrospect the fact we were all day trading tech stocks from Stanford’s computer labs probably suggested it was a bit of a bubble, although eToys options did pay for two consecutive Spring Break vacations. I was getting my MBA at the time which in some ways wasn’t just part of the DotCom storyline but an epicenter. Our professors were literally rewriting the case studies in real time and my participation in the very first Internet Marketing class the GSB ever offered is a form of carbon dating that conclusively proves my old age. But by my graduation in June of 2000, the party had ended. As became clear quickly: the Stanford Business School Class of 1998 had founded the good Internet 1.0 companies; the Class of 1999 had founded the bad Internet 1.0 companies; and the Class of 2000 was just plain unemployed. And so I left the campus with student debt and limited prospects. But it turned out to be exactly what I needed.

My decision to attend business school wasn’t really about getting the credential. I was there to get a MBA, not be an MBA. In fact, as a classic liberal arts major, I found myself more attracted to the PhD students studying theory than the curriculums built around understanding practice. And while 25 years ago a business school campus was a compelling way to build a professional network (there are many other methods now), I had other reasons for being there: to figure out who I was. Or maybe, more specifically, to give myself confidence to be who I wanted to be.

Right brain mother and left brain father left me confused… which one was I??? Pre-Stanford that meant trying out jobs to seeing what fit. Feed the left by working on Late Night with Conan O’Brien and be the only one geeking out about an Access database to track guests. Pivot to the right with a few years of management consulting and use Powerpoint on cross country flights to make stop motion animations. Neither felt perfect but my work ethic wouldn’t allow me to just stop and figure it out. But business school? Maybe that was a chance to pause and examine myself while still ‘moving forward’ in my career. So I applied to the one school that felt like a good fit and crossed my fingers.

tldr IT WORKED! Came out of Stanford with a mission: to work on products which mattered to me, with people I could learn from, and to feel like I was making a real difference to the outcome. All I needed was a job. Then this happened:


It wasn’t even the lowest moment of the crash as the stock market dead cat bounced a few times before heading lower for the early 2000s. Graduating into the bubble burst was no fun but had one very important benefit for me: there was no temptation to take a ‘get rich quick’ job. Over the previous years you could spend 12–24 month at a startup and become an IPO millionaire. Give a shit about what you were actually building? Is it sustainable? Who cares! You could justify getting in and then out and doing the important work later, with a swollen bank account. Now to be clear, this wasn’t everyone. There were absolutely founders and teams who selected areas that meant a lot to them personally, but the rose colored glasses were structural.

Would I have been tempted by this path? Absolutely! I was broke and needed money (had been working part-time at an enterprise tech startup along the way but otherwise savings were depleted). Man plans, God laughs as my wife says. No more jobs. Like overnight lots and lots of contraction, hiring freezes, and pulled offers. Sort of like, well, 2023.

The void of temptations meant I could stay the course and stick to first principles. It wasn’t always easy but I had a roommate, a girlfriend, a little bit of the income mentioned above, and some resolve. When six months later my networking connected me with Philip Rosedale and Linden Lab (the startup building virtual world Second Life), I knew I’d found the product I wanted to build, the people I wanted to build it with, and somewhere I though I could make a difference. And that’s where I spent almost three years. Linden Lab wasn’t an overnight success, not did it fulfill its potential, but it started me in the right direction. Which led to Google, then YouTube, and finally Homebrew.

The point here isn’t to sugarcoat the difficult time of a downturn. Or to be blind to the multiple advantages I had going into the DotCom failure. But I do believe that manic bull markets tend to cause people to make decisions which are clouded by lure of easy wealth, or herd momentum. If there’s a silver lining to downturns it’s they provide all sort of clarity, even at the individual level.


As a Human, I’m Excited About AI. As an Investor, I’m Still Wrestling With a Few Questions

Riffing Off VC Charles Hudson’s Blog Post, Here’s What I’m Trying to Answer

a group of different robots running a race, digital art [DALL-E]

If startup founders sometimes ‘Build in Public,’ is the analogou sventure capitalist motto to ‘Think in Public?’ Anyway, there’s no doubt that the story of the trailing months has been Artificial Intelligence. Over Homebrew’s first decade we’ve always been interested in what we’ve called ‘Applied AI’ (along with Applied CV, Applied ML)— opportunities where the technology itself was being extended and commercialized for a specific purpose (contrasted with core R&D or base model development). Companies such as Shield.aiKettle, and MasterfulAI, among many others, were Homebrew investments which fit this definition. But it’s also clear we’re at a new inflection point where our previous hypotheses needed to be updated. So like a stone in a polishing tumbler, ‘what are our principles here’ had been tossing around my head for a handful of quarters. And then I read Charles Hudson’s post, which prompted me [AI PUN] to just write this down.

In “Honest and Naive Questions from a Generalist Seed VC Grappling with the Generative AI Revolution,” Charles (whom I love) touches on similarish topics to what Satya and I have been chatting about.

I. Base Models

  • Given team, data, and compute costs, will the ‘price of entry’ and ‘price of innovation’ on base models increase or decrease over time
  • Will different data types produce/require their own base models, and under what conditions are these base models likely to be produced by different companies/sources vs under a single corporate umbrella
  • How does one measure ‘quality’ and what characteristics will base model owners compete on besides ‘quality’ [price, latency, privacy, etc]

II. AI ‘Middleware’

  • In a multi-base model world, won’t there be some value created by dynamically switching between models depending on the use case? Won’t most application owners who seek to integrate ‘AI’ be interested in “best results” more so than having to choose a model upfront
  • Will this middleware layer have access to enough model attributes to even know when/how to manage between models
  • Can these companies protect their margins or will they be subject to either (a) intense competition pushing margins down to ‘base model query price + a few basis points or (b) the base model companies behaving like the record labels and basically being very deliberate about taking the majority of revenue created by a service built on top of their IP
  • Will middleware be able to augment the base models with new proprietary data in order to create a differentiated product
  • Will middleware companies seek to aggregate proprietary data sources in order to improve base models in unique ways

III. AI ‘Native’ Applications

  • What are the conditions by which the addition of AI catalyzes new product offerings built around this technology versus ‘AI’ being a feature that the market leading applications can build into their platforms. Will Zendesk be replaced by an AI Customer Support startup or does Zendesk integrate AI. Repeat this question for everything B2B.
  • OpenAI is a for-profit, running a venture fund, etc — what types of ‘partnership risk’ is there in backing alternatives who are competing with OpenAI funded startups. Are all the base models doing to use their cash to try and develop their own ecosystems and implicitly/explicitly try to pick winning apps?
  • What will the engineering teams at ‘non-native’ adopters need to look like in order to successfully integrate, manage and compete with the native apps
  • Will businesses who believe they have proprietary data to may help improve base models be able to sell that data and/or ‘pay it in’ to the model in return for discounted usage? Will they seek to create improved layers atop the base models

If you have POVs here I’m always happy to hear from you [hunter at homebrew dot co]! Remember, we invest our personal capital (typically a $100k-$500k initial investment, although ability to go larger when appropriate) in your companies and then get to work supporting you.


Killing The ‘Must Have a Warm Intro To a VC’ Myth Will Be Good For Founders and Great for the World

Why I’m Participating in SeedChecks’ “Submit Your Deck” Community

We’ve never believed in hiding. Our email addresses are on our website, and there’s no junior staffer or AI Bot replying on our behalf. A strong Cold Email always beats a weak Warm Email. And we’ve backed successful startups where the relationship began exactly this way. So, yeah, we’re believers in being accessible and open to founders regardless of whether or not we share an existing network.

That’s why I’m participating in SeedChecks, an experience by which you can submit your pitch deck to a group of early stage investors without having to know any of us already. Everyone looks at your information separately and follows-up if there’s potential for mutual fit. It’s not a groupthink exercise and there’s no collusion, although hopefully maybe some collaboration as I’ve personally co-invested with many of the folks in the group.

Will opportunities like SeedChecks be the death of the warm intro? Of course not, but we’re all committed to the idea that now more than ever, great founders can be anywhere and anyone. So please consider submitting your materials if you’re looking to raise your first round of capital.


“Imposter Syndrome” is Definitely Misnamed, Might Be a Condition of Privilege, & Has a Fascinating History

Things I Learned From a New Yorker Article and How I Got Over My Own Insecurity

Good writers aren’t just skilled in their prose, they have a nose for interesting topics. “Why Everyone Feels Like They’re Faking It,” an article about imposter syndrome in a recent issue of the New Yorker, is an example of a GREAT subject. The type of read where you pause between sections to chew on what you just finished.

The Imposter Phenomenon, as the original researchers called it (the fact it’s mutated to a ‘syndrome’ is part of its questionable evolution and ubiquity), has been coming up in my communities, mostly as a result of the tech economy struggles. The belief that perhaps you weren’t good at your job, it was just the markets going up, or, even more insidious, that you were never good at your job so now that a bull market isn’t masking that fact you’re about to be found out, are two oft-repeated confessions.

a person, standing on the top of flagpole, very high up on the sky, digital art [DALL-E]

Regardless of how it’s being felt, I have my own empathy for people dealing with these internal snickers of doubt. For a long time my version of imposterdom was fueled by “I think I belong in this room but just barely, so I need to hold on tightly and/or constantly prove it, less I get kicked out.” As a result it was more difficult to be pleased by individual or team success, which only served as a reminder that the next race was beginning. And in hindsight, the perilous nature of my own perch probably made it more difficult for me to see conflict as a ‘fight or flight’ challenge, rather than an opportunity to build connection and shared understanding.

Thankfully, besides just getting old, I created hacks to retrain my defaults. They’re more fully detailed in this previous blog post (“How I Calmed My Imposter Syndrome with These Two Tricks”) but in summary:

What Would 18 Year Old Hunter Think About Where You Are?

Are You So Good That You’re Fooling All These People?

So back to that New Yorker article. First off, the research dates back to two women [Pauline Clance, Suzanne Imes — Oberlin College colleagues] in the 1970s who brought their own personal expereinces together, and then expanded to a broader conversation

The pair spent five years talking to more than a hundred and fifty “successful” women: students and faculty members at several universities; professionals in fields including law, nursing, and social work. Then they recorded their findings in a paper, “The Impostor Phenomenon in High Achieving Women: Dynamics and Therapeutic Intervention.” They wrote that women in their sample were particularly prone to “an internal experience of intellectual phoniness,” living in perpetual fear that “some significant person will discover that they are indeed intellectual impostors.”

Once their study was published in 1978 it set off a rolling thunder-like spread. Particularly charming was this reminder of how things went ‘viral’ before the Internet.

The paper spread like an underground zine. People kept writing to Clance to ask for copies, and she sent out so many that the person working the copy machine in her department asked, “What are you doing with all these?”

Then, nearly 50 years later, two other women coalesced around the idea that Imposter Phemoneom was capitalist gaslighting and a form a priviledge that focused on convincing yourself you belonged to the structure versus interrogating the very real barriers.

In “Stop Telling Women They Have Imposter Syndrome,” published in the Harvard Business Review, in February, 2021, Ruchika Tulshyan and Jodi-Ann Burey argue that the label implies that women are suffering from a crisis of self-confidence and fails to recognize the real obstacles facing professional women, especially women of color — essentially, that it reframes systemic inequality as an individual pathology. As they put it, “Imposter syndrome directs our view toward fixing women at work instead of fixing the places where women work.”

You should read the article, especially because it weaves the lived experiences of these four women together.

And remember how at the beginning I mentioned that a good writer chooses good subjects? Well this author, Leslie Jamison, also did one of my favorite 2022 New Yorker articles about the Choose Your Own Adventure series of books. Leslie has a nose for bangers!


AI Enthusiasm is Not a Bubble and Even if it was We Wouldn’t Necessarily Know it Yet

It’s Very Likely That Artificial Intelligence Will Be Worth More In Aggregate Than is Currently Being Invested (Just Unevenly Distributed)

In kindergarten my daughter learned to not ‘yuck’ someone’s ‘yum.’ That is, just because you don’t like something there’s no reason to share that in the moment with another person enjoying it. There’s a lot of yumming AI right now and it’s of course perfectly fine (often helpful!) to challenge this excitement on technical grounds. Or ask questions about responsibility and legality. Or question business models. But to respond to the current state of affairs but just shouting “BUBBLE” isn’t just valueless Yucking, it’s likely incorrect.

During the Installation Phase of a new technology (HT Carlota Perez) there’s a bubble phase that coincides with the frenzy ahead of deployment. It’s when it feels like the New Thing has limitless upside, that “anything is possible and everything before will be disrupted” mindset. This is largely a feature, not a bug, of our industry (and of venture investing). The challenge of course is to not blindly anoint any fad as the New Thing, and to defensively protect the New Thing from any criticism. Both of those lead to fake or inbred New Things.

Source: AVC

But from an economic point of view, let’s better understand what a ‘bubble’ actually means, because it’s often expanded and abused beyond the classic definition.

Bubble, in an economic context, generally refers to a situation where the price for something — an individual stock, a financial asset, or even an entire sector, market, or asset class — exceeds its fundamental value by a large margin. — Investopedia

So to suggest we’re in an AI Bubble is to say that the total enterprise value of AI that can/will be captured by private companies is less than the capital being invested into them right now. If you truly believe this, then yeah, shout Bubble from the rooftops, but I’d take the other side of this bet all day long.

Of course this doesn’t mean that all the value created will accrue evenly or the way investors expect it to. Quite clearly there will be ‘winners’ and ‘losers’ — maybe even some spectacular failures — but this doesn’t mean Bubble.

When a New Things cycle runs its course we end up with one of three realities:

I. Total Value Created < Total Investment Capital Deployed (Bubble 101. Perhaps scooters and other micro mobility startups of the last decade are an example of this?)

II. Total Value Created > Total Investment Capital Deployed *But* Highly Concentrated Winners (the last 15 years of ride share fit this bill? Can still feel like a Bubble even if not the classic definition)

III. Total Value Created >>>> Total Investment Capital Deployed & Multiple (But Not Necessarily Equal) Winners (this is the outcome of truly revolutionary and disruptive technologies. SaaS and Cloud perhaps?)

At a macro perspective, I currently believe this cycle of AI is much more likely to be II or III than I, with a bias towards the more distributed view of III (because I’m an optimist). But my thinking on where value will accrue is still formative and probably requires a separate blog post.

But it’s definitely not a Bubble 🙂


Changing The Face(s) of Venture Capital, Screendoor Hires Lisa Cawley, Our First Managing Director, to Scale Further

An Economic Vehicle With a Societal Mandate, Screendoor Backs Emerging Managers from Underrepresented Groups

My hope for Screendoor is clear, if not simple: we’re going to be the largest, and most impactful, investor in emerging managers. Our strategy for accomplishing this is to focus on new firms led primarily by underrepresented VCs, back them meaningfully, and support them via a community of peers, advisors, and institutional LPs.

When 10 of us founded Screendoor in 2021 this was the plan. Almost two years later we’ve backed 11 managers with over $40 million of commitments, reviewed applications from 500+ funds, and, most recently hired our first Managing Director to help lead Screendoor into its future. Lisa Cawley joins us from the LP side of the table, already having experience evaluating and investing in emerging managers as well as a broad set of venture models. In her own words:

Screendoor’s role as an LP of GPs is the needed connection between underrepresented emerging managers and the institutional investment community, with our GP advisors who have ‘been there, done that’ recognizing what it takes to build a firm in the absence of a long track record. I’ve never had more conviction that investing in first-time funds led by underrepresented emerging managers isn’t just a societal impact initiative. In today’s vast venture capital landscape, it’s ALPHA!

It’s not enough to change team compositions with a few new hires or add supplemental pools of capital (all of which are still important and necessary efforts to continue). We need targeted action that accelerates the impact of these collective endeavors. I’m elated to now fully focus my time and effort to lead Screendoor to capture this incredible economic opportunity for our phenomenal LPs and the communities they serve, act as a source of catalytic capital and counsel to the next generation of leading fund managers across all backgrounds, and change the face(s) of venture capital!

We’re proud and thrilled that Lisa saw Screendoor as a platform at the intersection of incredible financial opportunity and industry evolution. The idea that these two goals are potentially incompatible is a relic of the past. We intend, with a coalition of the likeminded, to be the future. Onward!


Virtual Worlds Are Trade Schools In Disguise

Second Life, Minecraft, Roblox Collectively Taught More People To Code Than America’s Top Universities Have

Almost all my Gen X peers had some lightbulb experience as a child with their first personal computer. Whether command line, or graphic design, or playing a game and wanting to know what made it work that way, the beige box transformed our lives. How fortunate to be born at a specific time and place and privilege!

Across generations there’s also a cohort who got pulled into technology by participatory virtual environments — from the earliest text-based environments to the successive user-editable immersion of Second Life, to Minecraft, and now Roblox. You don’t even have to squint too hard to see MySpace and Tumblr as 2D worlds, and the kids who designed background, templates and the like for those.

a kid sitting with a computer and a night sky full of lightbulbs, digital art [DALL-E]

When I think about all this it’s not just nostalgia, it’s optimism. Software is the most powerful tool we have and while access is certainly not equal, it’s more available than the high walled professions that used to be drivers of social mobility. And so I still get wet eyed a bit when I hear stories of ‘coding changed my life,’ even more so when it happens to involved a product that I worked on personally.

Danilo Campos has a lovely post about his own ‘learn to code’ moment via Second Life (where I worked out of grad school). As builders we have choices in our products and Danilo talks about how the developer experience of Second Life was ultimately responsible for his career. The things he calls out, such as ‘co-created living documentation’ and ‘frictionless sharing’ should be aspirational in all of our designs. I’m going to quote some passages below, but you really should read the whole thing.

I have the career I do because eighteen years ago, by accident, I learned to code in Second Life.

What began for me as a series of experiments with scripted 3D assets evolved into my first business and my first software products. I made enough money selling content in Second Life to pay my real life rent, for months. With this experience in hand, I was prepared for the iPhone’s App Store indie developer revolution, which rocketed me to a career in Silicon Valley startups.

There’s immense gratitude I feel for this experience. I’m a first-generation knowledge worker. The leverage of a technology career isn’t something I grew up anticipating. I didn’t even think writing code was for “someone like me.” What a joy, to surprise oneself this way.

And after building some items to sell in Second Life

What a revelation this was, discovering firsthand that you could make money through the internet. My working class roots had nothing even remotely analogous.

I still remember the night my third robot launched. The money kept pouring in. Every few minutes, another notification would slide down, another jingling coins sound effect. While it was great to clear a month of rent in a weekend, what was even more exciting was more than 18 months of passive income. The robot sold steadily, until everyone who wanted a science fiction robot appearance had found and paid for it and the cash petered out.

Forever after, I would see the world differently.

And his hopes for the future (written Fall 2022)

As this technology cycle sputters to a close, a new one lurks around the next corner. I’ve always carried the hope that a new platform like Second Life could emerge.

Whether or not we find a worthy, broadly-adopted metaverse in our future, I think these lessons can help any developer tools project find some leverage for growth, positive impact, and creative power.

Thanks Danilo!


You Probably Can’t Hire Stripe’s First COO But Soon You’ll Be Able To Read Her Book

Claire Hughes Johnson Joined Stripe in 2014 After a Decade at Google. Her Management Tips Are Legendary. Now They’re Published.

Imposter syndrome manifests itself in different ways. In my early career, it was primarily feeling that I *did* belong in the room (but just barely), and then trying to prove this to others around me. Eventually I relaxed a bit and got to just enjoy learning from my smart colleagues versus seeking approval. And what I found out was that some of them were really, really good at what they do. Claire Hughes Johnson belongs solidly in that cohort.

We overlapped at Google where she was a VP on the business side of the house but more notably she left the Plex in 2014 to join Stripe as COO when it was just a few years old. Claire got to experience, and played a large part in, Stripe’s proverbial rocketship, blossoming into thousands of employees, generating billions of dollars in revenue and valuation. While at the company — and especially once she departed — Claire became one of the people I always hoped to add to a cap table or startup board. There were just very few people who had the practical experience and framework-driven thinking she could bring.

But the truth is that human Claire can’t possibly scale to all the wonderful companies and teams that called on her. So instead she wrote a book, coming out March 7th, and available for pre-order nowScaling People: Tactics for Management and Company Building promises to be one of the best reads in 2023.

Probably the best preview can be found in an interview she did with Elad Gil for his own book the High Growth Handbook (also a must have). For example:

On her viral ‘Working With Claire’ guide

I think that founders should write a guide to working with them. It would be one of the pieces I’m describing, to clarify the founder’s role: “What do I want to be involved in? When do I want to hear from you? What are my preferred communication modes? What makes me impatient? Don’t surprise me with X.” That’s super powerful. Because the problem is, people learn it in the moment, and by then it’s too late.

On decision-making, and consensus

When I’m leading through a tough decision, I try to say, at the outset, “I want all of your opinions, but I’m going to be the one who ultimately makes the decision.” Or in some cases, I will say, “I don’t know if I’m the right decision- maker. I need help exploring what the decision vectors are, and I need all of your help. And then I will let you know how we’re going to make the decision once we’ve talked about it.” If you don’t give people that guidance, which is I think a common mistake, you’re likely to run into trouble.

On the value of ‘founding documents’

Then the other thing you have is your operating principles or your values or whatever vocabulary you choose. You need to codify a set of principles and behaviors and then cohere to them, culturally. And those founding documents shouldn’t change very often. We refresh those operating principles every year, but they don’t change that meaningfully. I don’t think founding documents should change frequently.

I cannot wait for Claire’s book and predict it’ll become the next Radical Candor, Principles, Build, etc for the tech community. Congrats CHJ!


Some of the Best Founders Are “Difficult” People

What To Look For When Reference Checking Polarizing Entrepreneurs

There are certain words I don’t want to hear when doing backchannel references on a startup CEO. Sketchy would be one. Unmotivated another. Or those special little bombs of a phrase like “enjoys playing founder more than being one” and “tells a good story but no follow-through.” These come up — once is a warning, twice is a goodbye — and I’m not making the investment. But there’s another characteristic that on the surface could seem disqualifying but actually deserves analysis, and that’s “Difficult.” Are we talking abrasive, egotistical, read the Steve Jobs bio and thinks yelling was the key? Or the opinionated, driven, strong-willed, fast twitch muscle type? Because while the former might have big time Life Is Too Short energy, the latter perks my considerably sized ears. But you need to go deeper and unpack the ‘Difficult’ a bit.

Don’t Be This Type of Difficult [screaming baby in a business suit, digital art — DALL-E]

Difficult can mean polarizing, not necessarily an absolute negative. If you combine this with self-awareness, you get a powerful combination for an early stage CEO. The things they are particular about — the stuff that makes them Difficult — they actually need to be good at, not just forceful. Is it a gruff exterior but with just a desire for excellence and impact, versus the difficulty being ultimately self-defeating to themselves and their companies?

Do they have a cofounder who can balance them out? Pair a Difficult CEO with a COO/CTO/CPO who knows how to manage alongside and whole just might be greater than the sum of its parts. Make sure to talk with this person as well. They can give their own unique insights into why they fit together, or share their own mounting exasperation.

Do they inspire zealots in addition to detractors? And do even the detractors say things like ‘hey, I wouldn’t want to work with him again at this stage of my career but I’d invest in something he founded without reservation.’ 🤩

For an investor, partnering with Difficult Founders also comes down to how you both think about relationship building. Are they Difficult but know what they’d be signing up for with you? Do you feel like it would take effort, but you could build a relationship? Do you trust them?

And what happens when you ask them about their reputation for being Difficult? The folks who recoil from these conversations or get defensive or blame others for every failure, that’s 🚨. But taking more of a learning mentality — believing that great companies *are* polarizing, but also talking about how building a great company will take more than just them, how their cofounder is a 1+1=3 situation, etc = ⭐⭐⭐⭐⭐

So net net, Difficult is definitely not disqualifying for us, but they do cause a second set of questions to understand whether the person can be a great leader/CEO and whether we’re going to be the best investor for them.