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
Tech Companies Who Strike Deals With Specific Creators Cease Being Neutral Platforms And Are Accountable To Repercussions Beyond Their Own Terms of Service “Neil Young should stay in his lane and j… | Continue reading
Why Being Thankful For Good Fortune Doesn’t Have to Ignore Impact of Effort & Skill “There’s no free lunches,” was the mantra my father repeated to me most often as a kid. I was taught tha… | Continue reading
And Why He Abandoned a Career in Web Ads for Leading Crypto Investing at The Chernin Group Even before my Jarrod Dicker starting tweeting in his “web2 vs web3” style, I gave him shit abou… | Continue reading
Get More Time and More Energy By Being Thoughtful About Your Calendar I’m a believer that one’s calendar is a very true representation of your priorities. If you feel like you’re not getting done t… | Continue reading
Shepherd’s CEO Justin Levine answers Five Questions on how his $6.2m fundraise came about & why it didn’t include me (yet) I love working with great people and as a venture capitalist, am fortu… | Continue reading
Multiplayer games “really gave me the feeling of being socially connected when I was otherwise on my own at home” My sense is that many people in our industry are fundamentally shaped by what tech … | Continue reading
Ellen DaSilva’s Journey, from Banking to Twitter to Hims and Now, Her Own NewCo! Like many relationships these days, mine and Ellen’s began online. But we successfully converted it to an NYC IRL co… | Continue reading
A Career In Startups From Dwolla to DAOs (and how to get whitelisted for the Illuminati NFT mint) When I befriended Alex Taub in 2013 he lived in New York City, didn’t have children, and certainly … | Continue reading
Why Being on a College Campus From 1991–1995 Changed My Life I visited the future and it made me wealthy. Not Biff and Grays Sports Almanac Back to the Future II style, but maybe again, not that fa… | Continue reading
What I learned from my own years building a virtual world “THIS IS GOING TO BE THE 3D INTERNET” a tech reporter boldly wrote. When was this claim made? Not in a 2021 tweet covering Mark Zuckerberg’… | Continue reading
‘Show them how smart you are’ wasn’t a very successful way to make friends Most people think of Imposter Syndrome as expressing itself most simply as “I don’t belong here,” as in “I’m not worthy of… | Continue reading
In 2010, It Almost Disappeared But Then I Put My, Err, Thumb On The Scale “This isn’t Disneyland,” I insisted while challenging our team’s recommendation that we remove the Thumbs Down (Dislike) bu… | Continue reading
Buying Talent Is More Attractive Than Renting In Today’s Competitive Venture Market Imagine getting paid a solid salary to sit around and think up new startup ideas, distracted only by the free foo… | Continue reading
Five Questions With Local Newsletter Author Nick Bastone I love me a good newsletter, especially one that lets us all keep up with local news in a succinct and actionable way. So when The SF Minute… | Continue reading
Sure It Doesn’t Ask Any “Hard Questions” But Maybe It’s Okay To Just Appreciate His Journey I don’t stan. I don’t have heroes or mentors. There are people whom I admire as humans but even then it’s… | Continue reading
How I Give Away My Money. And Perhaps How You Can Too! I still insist that we don’t talk enough about money in our community. I mean really talk — publicly, openly, emotionally. Philanthropy (which… | Continue reading
No Need To “Grab a Coffee and Pick My Brain” Because Here’s What I’d Say… A lot of new venture funds out there these days. People sometimes ask me, “wow, is there still room for new investors?” and… | Continue reading
What Leadership Roles at Facebook & YouTube Taught Rushabh Doshi About Building Product Teams What do I hope happens when I write a blog post? Lots of people to read it? Sure, I guess. But the … | Continue reading
Three Tips For Leaders Who Want To Up Their Recruiting Game Show me the first 20 employees of a startup and I’ll tell you whether it’s going to be successful or not. In my mind there’s no greater i… | Continue reading
Looking For Your Updated Feedback One of the areas I get the most cold emails about are career paths into product management, especially for folks without engineering backgrounds. I wrote my though… | Continue reading
This Has Been My Favorite Question Of Peers In 2021 “So, do you think your job is to win ‘consensus’ deals or find the ‘non-consensus’ opportunities?” This has been my favorite question to ask fell… | Continue reading
How My Attitude Towards Mental Health Changed From My 20s to 30s to 40s 2011 and I was at a low point. Most alarmingly, it wasn’t clear that I could get out of my situation by myself. The mental st… | Continue reading
VCs With Multiple Stage-Specific Funds Are Likely To Rewrite The Existing Etiquette. And What This Means For Founders. Let’s start out by admitting that the question of ‘competitive conflict’ has a… | Continue reading
Don’t Freak Out When Part Of Your Original Hypothesis Was Wrong If you showed me a bunch of random early stage startups and asked me to select the ones disproportionately likely to be successful, I… | Continue reading
Startup CEOs Should Test Strength of Cap Table Every ~6 Months To Know Where They Stand I really liked Jason Lemkin’s “Do You Have a Weak Investor Syndicate” blog post from earlier in the summer. G… | Continue reading
Why The Move to Remote Has Accelerated The Need for New Tools The first generation of SaaS was about single player workflows and data. The second generation added collaboration (aka multiplayer). A… | Continue reading
Why Their Multibillion Dollar Outcome Flipped The Script Pre-2014: Insider Rounds Are The Funding of Last Resort Post-2014: Why Are Insiders Letting This One Get Out? When WhatsApp took $19 bi… | Continue reading
Why I Cringe Every Time I Read This Word I recognize this is an overreaction. But humans have their quirks and one of mine is I cannot stand when the tech biz press uses “oversubscribed” to charact… | Continue reading
Why VCs Are Always ‘Very Excited’ About Your Progress But That Doesn’t Mean Anything Until They Make an Offer My job as an early stage investor includes translation services, specifically helping s… | Continue reading
Things to Remember As You and Your Friends Get Wealthy “Giraffe money.” That’s the phrase which stuck with me from Erin Griffith’s NYTimes article this spring about the latest set of weal… | Continue reading