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
Tough Love, Running Effective Meetings, Making Products That Produce Emotion, and More Cross-country flights are great times to catch up on newsletters and unread feeds. This week there’s a bunch I want to share with you. How Levels Does Meetings Levels is a consumer health compa … | Continue reading
The Things to Know When You Lose Your Job In A Downturn RIF aka reduction in force. Sounds like a Magic: The Gathering card but it’s actually a polite way of saying you’re being laid off. And with … | Continue reading
Andy Johns Was In-Demand As a Startup Growth Guru But Couldn’t Continue The Work Until He Helped Himself First Andy Johns was one of the original notable ‘growth’ experts, working at a variety of s… | Continue reading
Think Of Your First Non-Investor Board Member As a Senior Hire, And Not Your IPO Board Being a CEO and running a startup is hard! So you’d think that founders would take advantage of every resource… | Continue reading
Selective Leaks of Previous Discussions & Policy Debates In The Name of ‘Transparency’ Would Put Twitter Employees At Risk Typing “I know this makes me sound like a crazy person but..” as a blo… | Continue reading
Madonna, Like a Virgin Tour, June 1985 We recently took our daughter to her first concert, delayed somewhat by, you know, that COVID thing. It was Billie Eilish at the Chase Center a few weeks back. Good show. I’m glad my kid had enough taste to pick an artist that she likely wil … | Continue reading
Why ‘Living Below Your Means’ Is One Key To Success & Happiness $0 per year. That’s what my business partner and I decided that we wanted in salary from our newest venture fund. Or at least it was the resulting impact of declining to take additional capital from our investors and … | Continue reading
For Early Stage Startups, You Need Employees To Choose The Company. Not The Other Way Around. I love helping startups hire, especially early on. Look, companies don’t exist without founders — often when we write our initial investment checks there aren’t any employees — but nothi … | Continue reading
Let Others Call You a “Platform,” “Mentor,” “Low Maintenance,” & “Good in Bed,” Never Claim Them Tall. I can call myself tall. It’s objectively true because I’m 6′ 3″. Sometimes I j… | Continue reading
Learnings From a Decade Investing In These Types of Leaders We’ve sent hundreds of millions of dollars to startup bank accounts but none of those have gone to teams which don’t have at least one founder we consider to be ‘mission-driven.’ How do I define that term? Loosely, someo … | Continue reading
Their Pottery Caught Our Eyes, Their Philosophy Grabbed Our Hearts & Their Growth Intrigued Our Brains Coffee is very important to me. I mean, my Twitter screen name is “☕” so we’re talking identity-level important and by extension, any coffee-accessory must be up to snuff. I’m … | Continue reading
Why Investors Touting Their Mistakes Is Still Just Content Marketing “Ha you proved me wrong. I was too bone-headed to see it. Should have invested. Congrats!” That’s the tweet sent by the venture … | Continue reading
Two Great Reads on Leadership, and Rational Risk Taking Two great reads I wanted to share with you — one is about leadership, the other is about risk. Peloton’s New C.E.O. on the Tough Road Ahead I… | Continue reading
There’s a Specific Strategy For Getting Capital When Sentiment Turns Sour “There’s only one thing that entrepreneurs have complete control over, and that’s picking the market they want to operate i… | Continue reading
As Our Colleague Kate Stern Departs Homebrew To Go Back to Company Building, Here’s Her Advice At Homebrew we’ve stayed a very small group by design, believing at the earliest stages of a company, … | Continue reading