As a Seed Investor, Do I Want Softbank to Invest In My Best Companies Or Not?

Oh boy, conference season in the venture world and one enduring question this year has been “What to do about the Vision Fund?” It’s been a topic of lobby conversations, off-the-record chats and sometimes even an honest public panel!

What’s my answer to The Softbank Effect? First you need to separate the investments into two categories:

Mature Growth Investments a la Uber: Multi-billion dollar commitments to companies that are already at scale. So far at least these investments seem to contain some secondary sales. Which means as a seed investor, I’m thrilled to see Softbank invest. Yippee, go Masayoshi Son!!! It’s essentially a private IPO where early investors, founders and employees get some liquidity and Softbank gets minority ownership, maybe a Board seat. Cool, cool.

Early Stage Hybrid Buyout a la Wag, Brandless, DoorDash: Softbank becomes the largest investor on the cap table, sometimes clears out the Board, Continue reading "As a Seed Investor, Do I Want Softbank to Invest In My Best Companies Or Not?"

Finding Yourself In Places That Weren’t Built For You

“I’m tall, male, white, straight and wealthy. If it wasn’t for that ‘Jewish’ thing, I’d be fine,” I’d joked to another political progressive friend on Friday morning ruminating about the state of America. Tragic irony that 24 hours later I woke to a reminder about how that ‘Jewish thing’ leads some to believe we don’t deserve to be Americans, or to live at all.

On Saturday’s flight home I finished Rebecca Traister’s Good and Mad: The Revolutionary Power of Women’s Anger. Traister has been on the self-described “women’s anger” beat since the 2016 elections and the book is a kaleidoscope of sorts: political history of female protest; sociological analysis of patriarchy’s impact upon the emotional framework that women are allowed; #MeToo memoir; and race’s impact on gender solidarity.

It’s a good read. Took me back to my undergrad at Vassar. I spent four years at a place that wasn’t built for Continue reading "Finding Yourself In Places That Weren’t Built For You"

Dear Future Team Member, I Originally Didn’t Want You But I’m Glad You’re Here (aka Homebrew is Hiring)

Dear [NAME] – Welcome to Homebrew! I’m so glad you decided to join our team. I’ve done a ton of hiring and truly believe People Choose Companies, not the other way around. You left an awesome gig and passed up lots of other options to bet on us, and I’ll work really hard to repay that 10x to you. But because you now have access to Homebrew’s Slack and are reading messages about this role, I wanted to admit something before you come across it on your own: I was originally pretty dead-set against bringing you on board. Not “you” in particular of course, but more so the idea of growing at all. I was worried it would impact our culture, increase complexity.

What changed my mind? A few things. As we begin investing out of our third fund, Satya and I believe there are now enough portfolio companies Continue reading "Dear Future Team Member, I Originally Didn’t Want You But I’m Glad You’re Here (aka Homebrew is Hiring)"

A Strong Cold Email Always Beats A Weak Warm One

The “always find a warm intro to a VC” axiom is misunderstood. Its intent was to suggest that a mutual connection who can vouch for an entrepreneur’s abilities, experience and perseverance would be of value to the process. This is still true. It did not mean “find someone who happens to have the VC’s contact info and get them to forward an email without much context or relevance.” At least one third, and maybe as much as 50%, of the “warm introductions” I receive fall into this category.

What happens in this case? Something like the following…

Me: Hey thanks for the forward. Are you vouching for this person or just passing along? Are you investing as an angel, or would you if you could?

“Warm” Intro: Met him at an event somewhere but don’t really know him… Worked with her but she’s actually not that good… [or variation

Continue reading "A Strong Cold Email Always Beats A Weak Warm One"

Gee, Male: Using My Inbox As a Window To Gender Bias

If you can’t see it, you can’t be it. That’s why role models and representation is so important in changing the ratios of tech as we seek to build a more inclusive community that resembles society, and not our industry stereotypes. Last night I attended an AllRaise event where table discussion included male and female venture capitalists noting the differences in gender breakdown of their inbound dealflow. You can guess how it skews, no surprises here. We track our own gender stats at Homebrew and while we invest in female founders 3-5x more than the industry average, we know that as a two man fund, we don’t fully represent the transformation that we hope to help assist.

If you don’t know her, you can’t fund her. A few years back Google Ventures’ partner Rick Klau ran an experiment on his Twitter follow list and noticed he underfollowed women because his phone

Continue reading "Gee, Male: Using My Inbox As a Window To Gender Bias"

Second Seeds: The New Normal But Know This…

I delete my tweets periodically, so wanted to capture some good discussions regarding seed bridges and founder/investor expectations.

These two previous blog posts provide context

The Three Types of “Second Seed” Rounds: Too Cold, Too Hot and Just Right

For Fundraising, Seed is No Longer a Round, It’s a Phase

So what can mess up a seed extension process? Expectations gap!

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Then folks like Science’s Peter Pham and Breather’s CEO noted this maddening point about data

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As a seed investor, I find myself both as “existing investor” and “potential investor” depending on the situation!

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And as Agrilyst’s CEO points out, early stage pricing is almost always a “who knows?!?”

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Whatever your situation, just hope to play on and stay in the game! 

Investing Outside Of Silicon Valley: Now More Than Ever (Where “Ever” = 2013)

Homebrew is making more investments outside of Silicon Valley than we have in our history! That statement might be more dramatic if our firm was founded in 1983 instead of 2013, but speaks to a handful of changes in seed investing. Some of these are generalizable and our friend Semil Shah does a nice job covering several in his post “Investing Outside the Bay Area.”


What I want to emphasize though, is we don’t think about this as “value shopping” (trying to get cheaper valuations elsewhere) or “competitive pressure” (we believe our product is preferred by a subset of great entrepreneurs and there’s more than enough opportunities to deploy our funds solely in the Bay Area if we chose to do so). No, instead we are simply looking for minimally the right team to solve a big problem and even more opportunistically, companies that might actually be advantaged

Continue reading "Investing Outside Of Silicon Valley: Now More Than Ever (Where “Ever” = 2013)"

“The folks who have the most outsized successes are the least likely people to have been doing it for the money” – Jason Shellen Reflecting On His Time At Google, Startups

Jason Shellen and I overlapped at Google but for some reason, our best conversations always happened outside of the Plex – like on a bus heading to Google’s pre-TED dinner in Monterey, or some random startup event in San Francisco. Jason joined Google when Pyra Labs (the company behind Blogger) was acquired. We’re now both out of Google for enough to time to sit back and reflect on our careers, and the most important question of course, WHO KILLED GOOGLE READER (Jason was its founding PM).


Hunter Walk: So Jason, now that we’re old and can reflect a bit, what have you found – for better or worse – as a common thread in the career decisions you make?

Jason Shellen: I’ve always tried to work on problems I can’t stop talking about. Early in my career, I was compelled by clichéd notions of “changing the world thru technology,” but Continue reading "“The folks who have the most outsized successes are the least likely people to have been doing it for the money” – Jason Shellen Reflecting On His Time At Google, Startups"

A Handmade & Instagrammable Happy Birthday To You! (aka Punkpost App Makes Beautiful Greeting Cards *First One Free*)

My instagram feed is a combination of coffee roasters, 80s pro wrestling, @IronMaiden and #BulletJournals/Doodlers/StudyNotes. That last one might need explaining if you’re unfamiliar with the culture. Buzzfeed’s helpful WTF is a Bullet Journal provides a bit of an overview, but really you can simply look at this image and get a pretty good sense.

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I just love the personality dripping from structured handwriting, sketches, doodles and the like (note, there are also a bunch of fun Instagram doodle accounts – you can see who I follow if interested). So, not surprisingly, when a friend introduced me to Punkpost, it kinda blew my mind.

Punkpost lets you send handwritten cards – birthday, get well, congrats, anything! – drawn by artists and mailed directly to whomever you want. These unique creations are a flat $6 (plus any add-ons like glitter confetti or prints of photos you’ve uploaded) which isn’t much

Continue reading "A Handmade & Instagrammable Happy Birthday To You! (aka Punkpost App Makes Beautiful Greeting Cards *First One Free*)"

The 20% Rules: Some Success Porn From Theo Epstein That’s Actually Pretty Good

I didn’t click on that fake Warren Buffett tweet and I don’t stan for success porn like “Five Things Successful People Do In Their 20s.”

Buuuuuuuuuut, this advice from Chicago Cubs President Theo Epstein is pretty good.

“Whoever your boss is, or your bosses are, they have 20 percent of their job that they just don’t like. So if you can ask them or figure out what that 20 percent is, and figure out a way to do it for them, you’ll make them really happy, improve their quality of life and their work experience.”

He’s not saying “work 120% to get ahead” or kiss your bosses’ ass by doing their grunt work. It’s a bit more subtle than that. And a tactic that matches getting exposure to new opportunities with understanding the nuts & bolts of what your boss’ job *is,* so that you can ascend to
Continue reading "The 20% Rules: Some Success Porn From Theo Epstein That’s Actually Pretty Good"

“You need to be extremely good at picking up on subtleties and subtext in communication and this is not something men are famous for” – Taylor Lorenz on covering Internet Culture

I love anthropology even more than I love algorithms. Watching people use my products like Second Life and YouTube was always fascinating because unexpected things happened every day – emergent behavior. Taylor Lorenz is one of the best reporters right now in finding and sharing these stories. It’s gotten to the point where I can sometimes read an article title and just know it’s her byline. She was kind enough to let me fire five questions at her. Here you go!


Hunter Walk: Can you share a bit of your background, what led your to journalism and how you ended up covering tech for The Atlantic?

Taylor Lorenz: My career path is hard to describe. I actually made a list this year of all the jobs I had before my current one and it was 38. Basically, I worked in a bunch of other fields and around 2010, while I Continue reading "“You need to be extremely good at picking up on subtleties and subtext in communication and this is not something men are famous for” – Taylor Lorenz on covering Internet Culture"

Why This Latest Facebook Feature Is Likely About Civility, Not Virality

It’s hostage-movie gospel that you must get kidnappers to use your name, look at pictures of your family, learn about your life, anything that humanizes you and makes it more difficult for them to cause you harm. Maybe it’s just because I’ve seen too many of these flicks, (Taken 4 anyone?), but similar motivation came to mind when reading about Facebook’s new “Things in Common.”

CNET’s Richard Nieva reported on a Facebook feature which displays what you have in common with another commenter in the discussion threads on a brand or publisher page. For example, see the “From Phoenix, Arizona” on the screenshot below.

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If this was Facebook 2012 you might think they were trying to show you other people to connect with and befriend. That is, this feature was another exploration of how to expand the social graph. But I see it differently – I think this Continue reading "Why This Latest Facebook Feature Is Likely About Civility, Not Virality"

Me! On the Digiday Podcast (Transcript & Link)

Brian Morrissey is EIC of Digiday and we met online. That’s less of a confession and more an admission that I was surprised to be invited on to his podcast, given that they usually focus on the people actually doing the work in media, advertising and commerce. Maybe he was just being nice because I interviewed him on my blog earlier this year.

Anyhoo, the podcast was fun. You can listen here. Or if you’re more the reading type, I got a transcript made:

The Best VC on Instagram

The world doesn’t need your content, but if you enjoy creating, you should do it, without hesitation. That would be my advice to you as a human. But whenever a fellow investor tells me they need to tweet more, write more, start a podcast, etc, for purposes of content marketing, I tell them “sure, if you enjoy it. And pick a medium that you actually enjoy using, otherwise it’ll never work longterm.”

Insta VC

So it made me smile when I found a VC using Instagram in a way that I find brilliant. thingtesting is a classic product review account but with a lot of Instagram-native style (and new CPG brand, D2C emphasis). It’s author is a woman named Jenny Gyllander, an investor based out of the UK. I don’t know Jenny but she’s found a lane that’s fun, visual, whimsical and unowned among the yet-another-Medium-post landscape.


Go Jenny!


Old Man Yells At Clouds (and Aspiring VCs As To What This Industry Really Is About)

I get a lot of inbound from friends, acquaintances and Twitter followers about making the transition from Operator to VC. Here are the top three reasons – lightly paraphrased – for why venture interests them:

  1. “I love working on products and it seems awesome to be able to work on 10 at one time instead of just one”
  2. “It seems intellectually stimulating, spending your days talking with the smartest people and investigating new technologies”
  3. “I enjoy helping entrepreneurs and could see myself doing that as a career”

I have never heard someone say “I want to be an investment manager and a salesperson” despite this being THE fundamental job responsibility of a venture capitalist. And I think that’s one reason why we’re seeing more boomerangs from Operating to Venture and then back to Operating (or changing VC firms). People didn’t actually realize what the job was going to be and

Continue reading "Old Man Yells At Clouds (and Aspiring VCs As To What This Industry Really Is About)"

Boobs, Muscles & Fairy Wings: Everything I Know About How Humans Design Their Avatar Selves

It was a combination of early career anxiety and actual startup struggles which combined to make my years working on Second Life personally stressful. I remember my parents visiting our office and casting a sideways glance at the bottles of Mylanta and hard alcohol sitting side by side on my desk, like the cartoon angel and devil characters sitting on the shoulders of an 80s movie character wrestling with his conscience. With some hindsight perspective though, the tremendous benefits of the experience became clear – I had the opportunity to work on a thoughtful, innovative product with an amazing technical team and together we produced what is ultimately an ongoing, profitable company (even if it failed to achieve its full potential).

Besides the meta-learnings about how startups function, there were a [NeesonVoice] very particular set of skills [/NeesonVoice] that I took away from my years at Linden Lab. The other

Continue reading "Boobs, Muscles & Fairy Wings: Everything I Know About How Humans Design Their Avatar Selves"

Communities Can Grow Too Quickly

I was recently granted access to a Slack community associated with a newsletter I’ve been reading for a while. The kinetic energy of new members started on the #Welcome channel and then flowed to other discussions on themed channels. Whether intentional or not, the batched admissions – we were added as a cohort – created its own dynamics. It felt like an fun event. Reminded me of bit of when a startup we’ve recently invested in announces itself to the rest of Homebrew’s founder group.

Communities can grow too quickly and lose some of the camaraderie which comes with being part of a group. There are a number of dynamics which factor into the carrying capacity of an existing community to absorb newbies. Product designers and communities themselves will build in techniques to manage this scaling – for example, a hardcoded onboarding tutorial when you start an app or even

Continue reading "Communities Can Grow Too Quickly"

The One Problem Most Publishing Platforms Forget To Solve


joanna-kosinska-669797-unsplashDo you get excited reading about email newsletter platforms? I do. And there were two notes in this week’s article about Substack which made me clap my hands. First, they’ve hired Nathan Bashaw, previously of Gimlet and Hardbound, who is someone I believe thinks about storytelling, content and software in compelling ways. Way to go Nathan!

Second, that they’re not ignoring the Discovery elements of Substack’s platform:

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Imagine a spectrum where on one side it said “Utility Platform” and on the other end it said “Community Network.” So many publishing platforms get “stuck” on the Utility side. They keep building the longtail of software features to assist creators in serving their audience but leave it to the creator themselves to find and grow that audience.

The real value to creators – and I’d argue this is what YouTube got so right early on with Related Videos and Continue reading "The One Problem Most Publishing Platforms Forget To Solve"

What Do You Want From Me Besides Capital?

I live for that moment of flicker in an entrepreneur’s eye during a pitch discussion. The one which suggests I’ve asked a question which is simultaneously both new to their fundraising experiences AND interesting to them personally. “What do you want from me besides capital?” is flicker-producing more often than it should be. Maybe it’s because raising money itself can be such a trudge or many investors over-promise and underdeliver, that you’d be happy to *just* get capital and be done with it. But Homebrew is founded upon the belief that we’ll put sweat and reputation behind your startup, not just a wire transfer, so to me it seems like a normal question to help understand if you need things that we can, or can’t, provide.


The answers I receive typically fall across four categories:

1. “Vertical Expertise” – More hands and minds around the industry maze they’re traversing. Continue reading "What Do You Want From Me Besides Capital?"

FAANG Anxious

Subconscious anxieties hover over my FAANG relationships

FB: eventually every product becomes 50% ads

AAPL: they’ll release a $10k iPhone I can’t resist

AMZN: beats everyone & raises prices

NFLX: they’ll realize my HunterPatel login isn’t Satya Patel’s kid

GOOG: they’ll randomly kill my fav product