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 Y … | Continue reading
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 … | Continue reading
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 … | Continue reading
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 wantin … | Continue reading
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), an … | Continue reading
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 mor … | Continue reading
Got a Cold Email Asking This Question. Here’s How I Answered a metal robot holding a scales of justice statue, digital art [DALL-E]“I was wondering if you have any frameworks or thoughts on how to … | Continue reading
Why Pairing Junior Executives With External Mentors Can Accelerate Your Hiring and Their Professional Development Often at a startup it’s better to hire for talent, ambition, and commitment, than years in role or ‘did they have the job already somewhere else.’ For example, imagin … | Continue reading
12,000 Tech Workers Woke Up Friday To Find They Were No Longer Employed. Looking Back At My Own Departure in 2013. Google was about 1,000 people when I started in 2003, which means last week’s layoffs were more than an order of magnitude larger than the entire company I’d origina … | Continue reading
Great Podcast on the Marketing of M3GAN with CMO of Universal Pictures While I haven’t yet seen the movie M3GAN, I have seen the TikToks, the YouTube videos, and the box office numbers. And played my willing K-factor role sharing one of the clips with my wife (she wasn’t as amuse … | Continue reading
Is Their Company Name a Core Value Or Marketing Spin You learn a lot when buying a first home. I learned that there are principal agent issues with your realtor exacerbated by the transactional incentive model. I learned that disclosure statements can be worded in a very specific … | Continue reading
Leading Funding Rounds Now Requires More Thematic Focus To See, Pick, Win & Service Startups I’m going to make the case that early stage venture *firms* who want to lead seed/A Rounds can be generalists (in the sense they have a set of GPs who cover a broad set of areas collectiv … | Continue reading
When Private Companies Take On Nation States The eggs wouldn’t stay in my mouth. Reading this New Yorker article over breakfast left me gasping so often that whatever I was chewing needed to find another home. So what *is* quantum computing? Classical computers speak in the langu … | Continue reading
Ukrainians Can Destroy a Russian Tank For About The Price of a Nirvana Artifact. One thing is for sure, I never should have tossed those hair metal concert relics and other memorabilia from my teens. You know, the ones that in the eras before social media you’d buy and wear to sc … | Continue reading
Too Many Existing Companies Merely Delayed ‘Cash Out’ Dates Without Yet Changing Their Fates. If 2022 was the year of the startup layoff, 2023 is going to be the year of the wind down. It will suck — for team members, for founders, for customers of these companies, and for their … | Continue reading
Some link-blogging for the last Friday of the year. Enjoy! Certain types of humor can be timeless and Carlin, despite having died in 2088, gets recirculated for his incisiveness. Itzkoff looks at why both side of the political spectrum have embraced (some might say co-opted) the … | Continue reading
Why Investing Our Savings Instead of Other People’s Money Let Us Rethink What Venture Capital PMF Looks Like in the Decade Ahead. [Part Two] According to the physical rules of aviation, there is no way that a bee should be able to fly, but it doesn’t know that, so it does. The sa … | Continue reading
When Homebrew Started Investing Its Own Money, The Reaction From Our Venture Capital Peers Surprised Me [Part One] During the last several years venture firms approached fundraising like trips to an All-You-Can Eat buffet: fast, frequent, and without regards for the digestive imp … | Continue reading
Casey Newton’s Deep Skepticism Of Twitter Replacements & Getting More Comfortable With Substack’s 10% Take Rate My daughter knows Casey Newton as the ‘watch pro wrestling and eat chicken wings’ friend. She is not wrong. But beyond the bond of those shared pleasures, we also have … | Continue reading
Timestamp: May 1, 2022 an angry mob yelling at a computer screen, digital art [DALL-E] | Continue reading
You’re Not As Attractive As Lensa’s Magic Avatars Suggests. And Why That’s a Problem. Digital Plastic Surgery. Or maybe AR Beer Goggles. That’s what everyone’s Lensa Magic Avatars look like to me. If you’re VERY ONLINE™️ then you’ve certainly noticed these in your friends’ social … | Continue reading
When a High Flying Startup Implodes. As MultiBillion Dollar Private Companies Shrivel, What Their Investors Aren’t Saying About These Losses. As more high-flyer private companies find their shine tarnished, investors (or adjacent VC-explainers) remind us that it’s unfortunate but … | Continue reading
‘Sell calls.’ That’s what a conversation between a job candidate and a VC are called. We’re supposed to help seal the deal, get the person to sign on the line which is dotted [insert Glengarry Glen Ross gif]. Now, I LOVE these conversations with possible new team members, but tak … | Continue reading
Sometimes you meet a founder during a startup pitch and you just know you’re going to be friends, regardless of whether they take your money or not. Avni Patel Thompson is one of those people. And I was right! So when writing about Second Time Founders, Avni came to the top of my … | Continue reading
Joe Fernandez (Klout, Joymode, NewCo) On What Changes After Your First Company I’m currently obsessing on repeat founders, and what lessons they want to share with the startup community. Just like my earlier request of Sean Byrnes, it made sense to pub Joe Fernandez’s response in … | Continue reading
Satya and I signed Homebrew on to an effort called VCsForRepro alongside ~100+ other investors representing over $100b in AUM. The organizers did a great job pulling together a coalition of folks willing to say that the ability for women to make choices about their reproductive l … | Continue reading
Our industry talks about ‘repeat founders’ with a lot of reverence and for good reason given the commitment required to build a startup. We also sometimes think of it as a single cohort, but there’s a probably more nuance. The ‘first startup failed but she learned on someone else … | Continue reading
I LOVE doing reference checks — on founders we are hoping to support and key hires into their teams. On-sheet (provided by the individual) and back-channel are both valuable in their own ways. Don’t incorrectly write off the ‘candidate supplied references’ thinking that it’s wort … | Continue reading
I love doing quick Five Question Interviews to learn more about people in my community. Sar Haribhakti took it a bit further — I think he does closer to 15 questions 🤣 — but enjoyed being on the other side of the table for this Q&A (“Coffee brew, political takes, and shop … | Continue reading
Helping Writers Monetize Their Free Readers More Effectively By Opening The Platform Up (and Taking a Cut) Consider me a fan of Substack. Yes, I disagree with aspects of their content policies (and occasionally wince at the arguments they make to defend said choices), but the com … | Continue reading
Five Questions With Unicorn Auctions Cofounder Cody Modeer My hobbies are largely consumptive: coffee and whiskey (the former to excess and the latter more modestly). Whiskey, specifically bourbon,… | Continue reading
The Art of Asking “If Not You, Who Should I Talk To?” I failed. You see, there was a really talented Consumer Product Manager at Google that I was trying to get over to YouTube. He’d decided to leave Mountain View and work on a new startup, but I thought there was an opening. May … | Continue reading
VC David Sacks Was Right When He Said “Default Alive” Is a Trap In New York City, altitude is attitude and the view from $100b+ fund’s office tower was certainly the equivalent of walking tall, sho… | Continue reading
Primary Thoughts About Secondary Transactions As my man Kenny Rogers sang… You’ve got to know when to hold ‘emKnow when to fold ‘emKnow when to walk awayAnd know when to runYou never count you… | Continue reading
Hint: The Answer Doesn’t Involve a Spreadsheet I’m not an investor in Figma. I don’t know Figma CEO Dylan Field. And I’m not a designer. So this means I’m either perfectly positioned to give you my objective comments on Adobe’s $20 billion purchase of the startup, or totally unqu … | Continue reading
The Four (!!!) Checks I’ve Written The Company Since Saying “No,” Never Bought Me As Much As Saying “YES!” Would Have In The First Place. An Investor and a Founder Postmortem a Mistake The common VC passes are pretty cliche. “It’s a bit too early for us but we’ll be rooting for y … | Continue reading
Why This Repeat Entrepreneur Founded Frank, a Software Platform for Workers. And Does He Think Chicago Is a Good Place for Entrepreneurs? Logan is another one of those folks that I can’t recall specifically how or why we met, but I’m so thankful for his friendship. He’s someone I … | Continue reading
From Box to Glossier, and Comms to Venture Capital, Ashley Mayer Is Carving a Pretty Unique Path. What She’s Learned, And What You Can Learn From Her. We had overlapping circles and then became friends. I’m an Ashley Mayer superfan so beyond the affinity, have been fortunate enou … | Continue reading
You Might Learn About Entrepreneurship Reading Andy Dunn’s Burn Rate But You’ll Learn Much More About Being Human The realization of how mistaken I’d been hit somewhere around page 24 when the author details slipping into a psychotic state where he believed he was the returning M … | Continue reading
Why Bringing These Two Skillsets Onto Your Cap Table Early Is Worth It In 10 years of venture investing I don’t think I’ve ever participated in a seed round which had less demand than supply. From a macro sense, you can thank the bull run our industry was in for the last decade. … | Continue reading
Fortunately They’re Really Simple To Fix! You might think my job is about saying “yes” to founders, but statistically it’s *actually* about saying “no,” given we typically see 3,000+ comp… | Continue reading
One of My Liabilities as a Leader Was Not Acknowledging the Wins Along The Way “I don’t want praise, I want to know what I could have done better.” For years this was my default response to even th… | Continue reading
Why I’m Not Telling Every Startup To ‘Pull The Brakes’ Just Yet Here’s how I’ve generally described what’s occurring in tech land over the last few months: For a variety of reasons, technology comp… | Continue reading
We Wrote These For Our Portfolio Founders But Want Everyone To Have Them When we started our venture fund Homebrew one of our goals was to help grow the startup pie, so to speak, not just get our slice. Writing up what we consider ‘best practices’ and sharing with the broader fou … | Continue reading
Why Some Smart Startups Are Putting (Paid) Projects Ahead of Employment Offers 80–90% of startups shouldn’t follow the advice I’m about to give. Instead these companies are better off just investing resources in improving their hiring via candidate flow/sourcing, interview proces … | Continue reading
Some Recommendations For Startup CEOs to Help Make Sure Your Team Member Actually Shows Up Most hiring processes start with an antiquated assumption that companies select people to work for them. In the world of technology startups we know that it’s usually the other way around: … | Continue reading
I’ve Spoken With Hundreds Of Potential Employees, Most Don’t Ask Everything They Could The other day I was sitting in a New York City park, talking to a senior engineer who had an offer from an ear… | Continue reading
What Makes A Culture “Bad” Isn’t Just That You Don’t Like It I won’t invest in a startup that doesn’t care about its culture. Because a culture is going to form regardless so you might as well be d… | Continue reading