“It’s okay to take profits and not hodl forever.” Does this make Alex Taub a web3 contrarian or just reasonable?

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 did not yet have thousands of dollars invested in virtual race horses. Now that all three of those situations have changed, I figured it would be worthwhile to check in with him about living in Miami, going deep into web3 and his latest startup Upstream.

Hunter Walk: Ok, we met back in 2013 after we invested in theSkimm and they said you were one of their friends/navigators of the startup world. What were you doing at the time and how did that insert you into the NYC startup scene?

Alex Taub: Yep, I think I did a reference call for them with you guys. I was working at Dwolla at the time but about to leave and start SocialRank. I had been in the NY tech scene since 2008/2009 and was just, generally, trying to be helpful to founders, investors, etc. I really liked what Carly and Danielle were working on and helped them get it off the ground. My claim to fame is I am the godfather of theskimm — something I wear proudly.

Before becoming a founder, I worked at Aviary for two years and then Dwolla for two years (the latter with my future cofounder Michael Schonfeld). I deliberately tried to work with people that I could learn a lot from and really engrain myself into the community. By the time I was ready to start a company I had already accelerated my career to the point where I was about one degree away from most people in the NY tech scene. This just helped speed certain things up.

HW: You then started your own company in the social media marketing/analytics space (SocialRank). I thought you were never supposed to start a company dependent upon platform APIs (jk, not jk)?

AT: We learned that expensive lesson. We heard it once or twice from people (and now I tell anyone that will listen) while we were building but obviously we thought we’d be different. SocialRank is a great product — we had awesome customers like the NBA, NFL, Netflix, Samsung, L’Oreal, even The Rock. We built it to over $100k in MRR. We just hit a point in 2018 where the Cambridge Analytica scandal went supernova and the platforms began rolling back what data you could and couldn’t get from them.

We saw the writing on the wall and put SocialRank on auto-pilot while thinking of new ideas. At the time it was some of the most stressful of my life. We were sub-5 people, we had raised some money, we were profitable, but any day the data could be impossible to grab and it would be over. We had a few moments when we thought it was over.

Now looking back, it was some of the most fun of my life. We went to the office every day and shot the shit about ideas. Each trying to convince each other of different businesses. We ended up developing Upstream from that. But yea don’t build on top of third party APIs, especially when you are deathly dependent on them.

HW: Then you moved to Miami, where I hear you’re breeding horses, just virtual ones. Clearly you’ve redpilled web3. Why are you such a believer, and what’s one aspect of web3 that you’re more contrarian about?

AT: Love Miami. We are staying. We were in a 2 bed in NYC with 2 kids during COVID. We would go on vacation to Miami and always ask ourselves why we don’t live here. Right before lockdowns in March we were in Miami so once we decided we needed to leave, Miami was top of the list. We officially moved here on July 1st. Will always love NY but I think Miami is our home for the foreseeable future.

Yes — I own a lot of digital horses. Own some good names too like Adidas, Puma, Warren Buffet, Beatles, and more. I’m a big fan of zed.run and think they are trailblazing in the web3 / gaming space.

My buddy Drew Austin got me into NFT’s back in December of 2020. Bought a few NBA Top Shot packs and loved the experience. Then Drew and I started hosting a weekly event on Upstream (every Friday at 1pm ET — even this week). We would have founders and teams come on each week to talk about their projects. It’s been a lot of fun. If you came to the weekly event and bought things that guests were talking about — you had a very very good 2021 (at least financially).

Money aspect of web3 is great but it’s just a piece of it. The community and camaraderie is like nothing I’ve ever seen. I’ve made more friends in and around web3 this past year than I did in the last five. I wrote this thread about why / when I buy NFTs.

I think contrarian wise, although I don’t think it is generally contrarian, but that most of this stuff is worthless. Most projects will go to zero. People will lose a lot of money. I think most people expect that so it’s probably not contrarian. Maybe my more contrarian take is that it’s okay to take profits and not hodl forever.

HW: Upsteam, your current startup, originally felt like Alex-as-an-App — it was a professional gathering spot with Needs/Wants (aka networking) productized. Now it seems to have evolved quite a bit. What has this particular idea maze been like?

AT: Great question. So the original idea around Upstream was what would a professional community platform look like if it started today. Not LinkedIn exactly, but more like LinkedIn Groups (which most people don’t realize exists). We found that for most professional groups, they were using slack, whatsapp, discord and while all of those products are awesome and things I use daily (if not hourly), they didn’t make sense for professional groups. So that was the start. We felt like the most interesting thing happening in these slack communities were people asking for help (I’m looking for an intro to X, or I’m looking to hire a part-time CFO). So we started off with a simple place to give and get help. Then COVID hit and we added the ability to spin up short virtual events (around 30 minutes) around meeting people. We felt like giving and getting help and meeting new people went hand in hand. To help people, a majority of the time, you need to know people. It’s usually people routing help (and not doing the help themselves).

That product took off and it became very popular pretty instantly. The events were great ways to launch communities. We have a Miami tech community, an NFT Community, a Future of Work Community, and a few hundred more.

Now around the summertime, I was chatting with a friend and they asked why Michael and I weren’t doing anything in blockchain / web3. We had been very early with Dwolla (I think Bitcoin was around $4–5 when we joined), we had an ethereum rig running in our office (when we didn’t have to pay for electricity). She was wondering why we hadn’t looked at ways to get back in the blockchain game. I didn’t have a good answer and started thinking through what we could even do. The NFT community was one of our more popular communities. So we thought maybe something there.

We then started to think about the future of Community in general. Community 1.0 was very geo focused — IRL. It was the country or city you were born in (what team you rooted for), what synagogue/church/mosque you belonged to, what local club you were a member of. Then Community 2.0 was URL — it was interest based and online. Discord, Facebook Groups, etc. Now Community 3.0 includes both but it is the concept of DAO — having transparency and ownership into the community. Instead of funding an admin to run it, you are funding the community itself (and have corresponding ownership).

We started to dig in to see what DAOs existed, the experience in starting them, and we realized a few things. The first was that unless you had technical abilities, spinning up a DAO was very difficult. So either you had the skills or you had to have money to hire someone to do it. The second was that to properly run a DAO you needed to use a bunch of different tools — Aragon for governance, Snapshot for voting, Juicebox for treasury, Collab Land for token gating, Discord for community, and on and on. There also wasn’t a leader in this space just yet, even though most people in the space believe 2022 is going to be the year of the DAO (like 2021 was NFT and 2020 was DeFi). So we decided to build a no-code full-stack DAO in a box, called an Upstream Collective, that anyone can spin up and run a DAO without needing technical experience and could do it all from one place. We launched it three weeks ago and the demand + usage has far exceeded even our most idealistic expectations.

And while it might look like a pivot from the outside, I look at web3 as a tech upgrade. We were always trying to build the future of communities (albeit professional ones, to start). DAOs, to us, are just the future of what a community should be / looks like. So it feels like an obvious evolution.

HW: From collecting NFTs to your own project Illuminati NFT. I’ll link to the full backstory but for folks here, what are the questions someone should ask themselves before starting their own NFT project? [Disclosure: i’ve minted one for myself]

AT: Yep — I give a little summary about what we are doing here,

I’ve bought a ton of NFTs and I’m excited to be on the other side of it. It’s a wild ride. The idea came from the Collective/DAO product we built (but at the time were building) at Upstream. I’m excited to use the Collective for this in a unique way. We have so many ideas on what we can do with this and the community has been super strong from the jump. If I could go back in time I would have maybe tightened up the roll out. One month in NFT land is like a decade. We should have done all the phases in 2 weeks max.

And before I answer the question — if anyone reading this wants to get whitelisted — just hit me up in my DM’s on Twitter (@ajt). Public mint is Jan 2nd/3rd.

That being said it’s a fun experience and I recommend people find a designer friend (or if you are that designer friend) and take a shot at making something. The whole dynamic of community/discord + mint + utility is a lot of fun and you’ll make a lot of friends. Ask yourself what it is you are hoping to get out of launching the project. If it is money — that’s okay. No shame in making money. But be open about that. That’s the only question really to ask — what are you hoping this becomes? The answer could range from life changing financial windfall to meeting some cool people and hanging out. While I think there are a lot of projects out there I still think some of the best ones haven’t been built yet.

Thanks Alex! Happy holidays everyone and you can follow Alex (@ajt) on Twitter.

I’m Successful In Tech Because I Managed To Visit The Future Without A Time Machine

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 far off. You see, being on a college campus in the early 90s was a preview of what the next few decades would bring. A high-speed network and connection to the Internet. A vibrant online campus community using chat, email, LAN/WAN gaming. Status messages and virtual identities. Connections to public research databases and libraries. A text and then graphical browser. Expectations of your own personal computers and connecting to class intranet sites for collaboration and documentation. I experienced multiple ‘holy shit’ moments where it felt like the Internet was going to change everything and I was an early adopter.

One Matrix moment were signing up for newsgroups like alt.music.beastie-boys right before winter break, selecting “receive all posts individually” [not savvy enough yet to always default to digest-mode] and returning in January to a crashed email account with over 20,000 new messages. I saw that the Internet was about people, and creativity, and tribes. And that informed all of my personal and professional choices afterwards.

In Outliers, author Malcolm Gladwell famously popularizes the ‘10,000 hour’ rule — namely, it takes approximately that amount of time to develop true expertise in an area. The book goes deeper than this soundbite though, talking about the biases which help to influence *who* gets access to the right training and development opportunities. One of the most important points is that it’s not just about the dedication, it’s about the 10,000 hours coming during the right period. The Beatles during the dawn of mainstream pop. Bill Gates during the advent of the personal computer. And so on. It’s a worthwhile debate as to whether people of this talent level and compounding privilege would have succeeded anyway during a different period of time, maybe just in an adjacent specialty that was more of the zeitgeist — eg put Bill Gates in the Renaissance and perhaps he’s Copernicus- but regardless it’s important to remember that it’s not just the individual but the circumstances they find themselves in. And I found myself in a pretty amazing set of circumstances for the first half of the 90s. Also, let me be explicit, I’m not comparing myself to the Beatles or Bill Gates. Well, maybe Ringo.

This all leads me to wonder, what can an 18 year old do today to ‘live in the future?’ Is it a specific geography? For a while it felt like residing in one of the major Asian cities gave you a sense of what urbanization, mobile tech and popular culture could look like down the road. Is that still true? Perhaps it’s not a place but a platform. Is redpilling web3 and spending your life in Discords the best approximation today of what will be more mainstream in 2031? Or maybe it’s actually ethnocultural and being of mixed race today is the best experience to understand the societal true north ahead. I really don’t know. But what I do know is that if you are early in your life and career there’s probably nothing better you can do than try to get to the future ahead of everyone else. It’ll change how you look at everything around you from that point forward.

Avatars Don’t Poop But You Can Be Sure The Metaverse Will Have Toilets

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’s vision of the metaverse, but in an early 2000’s magazine article forecasting a rosy future for the virtual world Second Life (SL). I was working there at the time, a young team member in his first startup post-grad school. As the ‘non-engineer,’ I did a little of a lot, and a lot of a little: consistently some product management work, but also tasks as diverse as writing our first community standards, negotiating the software license for a physics engine and trying to forecast when a $400 out-of-the-box Dell tower PC would be able to meet our minimum hardware spec. You emerge from experiences like these with [Liam Neeson voice] a very particular set of skills, and I’d say my nearly three years at Linden Lab, the parent company of Second Life, certainly impacted all the work I’ve done since.

Some of you might be familiar with SL but here’s the short story: there’s a historical category of ‘metaverse’ products that tend to gravitate towards the user-designed, open-ended, physical simulation attribute set. They can be centralized (‘land’ is hosted by a single company) or decentralized (anyone can host a server so to speak). Second Life was one of the most notable early entrants in this category, with ambitions and innovations which transcended its perpetually plateaued consumer adoption. Minecraft and Roblox are infinitely more successful versions of Second Life with the ‘realism’ attribute dialed down.

All of this is to say, you can imagine that as our industry “pivots to metaverse” has led different people to ask me, what did you learn from Second Life? I’ll tell you what I learned. There are going to be toilets there.

The question about whether your virtual world should have toilets is fiercely debated. Ok, maybe not. But I’ll tell you, watching our users build bathrooms and toilets in a world where avatars don’t need to pee or poop (let alone have genitalia. Yes, it’s true that SL avatars had attach points on/near the waist where maybe it was possible users designed performative or ceremonial genitalia but the natural form did not), was surprising. But it goes towards an understanding of what artifacts we carry forward from our banal humanity into these virtual spaces and which do we seek to shed. It’s why metaverse platform builders need anthropologists not just engineers.

I’m using this short toilet anecdote mostly as a way to share the work of Nick Yee, who impressed me with his research and surveys of massively multiplayer online games (MMOGs). I hope it doesn’t get lost just because it’s ‘old’ (2002–2009). Nick’s work confirmed for me why and when people bring IRL habits and etiquette into simulated environments (for example, avatars tend to stand around in clusters that mimic the spacing and positioning that we’d take in our own conversations even if it’s unnecessary in a digital world).

Technologists have a tendency to always be looking ahead, sometimes with a bit of optimism or naïveté (or ego) that what they’re doing is uniquely new. I’d never want to remove this completely because as a whole it serves us well. But Beginner’s Eyes tempered with a bit of compounding learnings serves us even better. So I hope in the rush of new talent heading towards metaverse projects we don’t forget to distill what we can from the past.

Update 12/2

The best thing about writing posts like this is they invite other memories from my Second Life colleagues. Frank Filipanits, who was there even before me, shared this:

How I Calmed My Imposter Syndrome with These Two Tricks

‘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 this success, am all a fraud, and will eventually fail.” For me it was a bit different. My belief was that I did belong, but barely, and in order to maintain my place, needed to constantly remind people/show that I was smart. Needless to say, this inner voice isn’t a healthy one when trying to work on teams and inspire trust.

I’ve written before around my own challenges outrunning the ‘failure tiger’ nipping at my heels for so many years and how that finally resolved. Now I wanted to get a bit deeper on the Imposter Syndrome side and the two hacks which calmed my anxiety. Assume zen pose…

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

Through a lot of my 20s/30s the meta-question of “am I doing enough? accomplishing enough? fast enough before I’m X years old” was a cerebral echo.

Sometimes people would tell me to calm down, seek balance and so on but this only caused me to think they were trying to make me complacent. “Yeah, whatever,” I’d think while listening to their wisdom, “that sounds fine if you don’t want to succeed but I’ve got plans! [or some variation of that]”

Or I’d hear “when you’re older you won’t worry about having worked one hour less. You’ll prize the [family, religion, hobby, whatever] that you made time for.” But all I imagined was old Hunter forever sitting alone in a room by himself, eating canned peaches and listening to baseball games on a cheap transistor radio. #FailureTiger

What ended up working wasn’t picturing myself in the future, but going backwards to my childhood. “If 18-year-old Hunter saw 35-year-old Hunter’s resume, what would he think?” The answer was he’d be pretty friggin’ excited! He’d think life was awesome and what a privilege it had been to work on interesting projects with interesting people. And how this would likely create several decades more of opportunities for his 40s, 50s, and beyond.

18-year-old Hunter wasn’t stupid. Overconfident, a bit smug, poor grooming habits maybe. But not stupid. And so I decided to trust 18-year-old Hunter more. If he was proud and excited by what present-day Hunter was up to, then maybe I should listen to him.

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

I’d been lucky to meet lots of people along the way that I considered to be smart and accomplished. Way more so than me. Not mentors, I always disliked that word, but maybe role models? Or people I admired? A reasonable number seemed to tolerate me, perhaps even, gulp, like me? Respect me? Trust me? So I asked myself how did this jive with my own self-doubt.

“Hunter,” I told myself, “let’s review: you believe these people are really smart and perceptive. And you also know that they seem to accept you as someone worthy of their time, attention. So, do you think you’re fooling them all?”

I liked this question because, perversely, the Yes or No answer gave me comfort. Albeit it to different degrees and one much healthier than the other.

If the answer was “No, they couldn’t all be fooled by you” then I wasn’t an imposter. I belonged!

And if the answer was, “Yes, you are such a talented psychopath that while you’re not classically intelligent and don’t deserve to be a part of these circles, you’re able to fool them for long periods of time,” well, then I still got included. Note: I actually think these sorts of people do exist/thrive for periods of time — Talented Mr. Ripley anyone?

For the record, I assume the former, not the latter, as a personal truth.

None of this is meant to imply that I’m totally free of my Imposter Syndrome tendencies but they’ve lessened substantially and I have these two mechanisms for ongoing support. And that means a lot.

Blame Me For YouTube’s ‘Dislike’ Option. But Now I’m Glad They’re Removing It.

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) button off the YouTube Watch Page during its 2010 redesign. “We’re. Not. Hulu.”

The Thumbs Up/Thumbs Down feedback options had already replaced YouTube’s Original Five Star rating system. After not surprisingly finding that the majority of Star votes were for One or Five Stars, the team decided to move to a UX which better reflected the binary choice. I honestly don’t recall what prompted the “should we remove Thumbs Down” discussion a year later, although it was likely because (a) it was already causing creator distress to see their videos ‘disliked’ and (b) the rest of the team was smarter than I was 🙂

Actually let me amend that: not just smarter, but more diverse in representation. Although perhaps our overall employee stats still didn’t reflect the breadth of backgrounds our industry strives for in current day, we did know that we wanted our team to look more like our user community than a typical tech company. So I’d like to imagine that the presence of more POVs resulted in one or more people’s lived experiences contributing to the idea, even back then, that platforms had a responsibility to think about trust and safety in a broader manner than just preventing illegal activity.

But I didn’t see it. I wanted the visible feedback loop on content that was objectionable, or untruthful. I thought Thumbs Down would help move the larger media companies to see that they had to play by the YouTube community’s rules — you upload a commercial instead of the actual clip people want to see? Thumbs Down! And I thought that part of being online was being open to “criticism.”

Now in 2021 YouTube just announced they were removing visible displays of Thumbs Down, rolling out progressively across the site. You can still vote Thumbs Down on a video, but those stats will only be visible to the creator and not displayed on the playback page. Simply, in their words, “the dislike count will be private across YouTube, but the dislike button will remain.” Smart.

As one would expect if you’re changing the UX for a product used by 1+ billion people, this was informed by data and intention. YouTube is seeking to “help better protect our creators from harassment, and reduce dislike attacks — where people work to drive up the number of dislikes on a creator’s videos.” In fact, they ran an earlier experiment of this change and saw a “reduction in dislike attacking behavior.” This is good and part of a general industry trend to prevent creator burnout.

So major kudos to the 2021 team doing what I prevented the 2010 team from shipping. They were right then and you’re definitely correct now.

‘Entrepreneur In Residence’ Used To Be One Of Silicon Valley’s Most Prestigious Titles. Now It’s Dead.

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 food and opportunities to sit in on discussions of the latest, hottest technologies. Well, if you were an Entrepreneur-In-Residence at one of the large Silicon Valley venture firms during the last few decades, that was your gig. The quid pro quo was that if you settled on an idea that the firm found to be fundable, you’d give them first shot at backing you, although not necessarily exclusively and certainly not contractually. It was more of an unwritten rule. Repeat entrepreneurs and departing big tech company execs would often do pitstops as EIRs, sometimes even simultaneously at two firms (otherwise known as the circa 2008 Jeff Weiner Flex). But now in 2021 you rarely hear about EIRs and they’re certainly not the golden prize of previous years. Why is this?

VCs think WHY RENT WHEN YOU CAN BUY? In today’s market, where there’s limitless capital chasing “consensus startups” the risk of waiting to write a termsheet is too great. If you believe enough in a founder to invite them to be an EIR you might as well just give them some money on a note and let them iterate with you already pot-committed. Otherwise someone else will swoop in and offer them an alternative. So a GPs incentive is to take a flyer and let the founders explore their interest areas with that capital, rather than as an EIR. If nothing comes of it the company will just unwind/return capital, or worst case, it’s a writeoff for the fund. But that risk is worth taking these days for the large VCs.

Founders RATHER USE THEIR OWN MONEY OR ANGEL MONEY if they’re not ready to take venture dollars. Before you tell me that the majority of founders don’t have their own capital already and/or a network of friends and family that can write them six figure checks, let me remind you that I’m talking about EIRs specifically, which were already predominantly repeat entrepreneurs and/or Big Tech Co execs. A 10+ year bull market means that the significant majority of these people have the capital to self-fund for a bit and/or more wealthy friends than the did in 2011. The end result is that why entangle yourself in an EIR role if you don’t need the salary, don’t need the introductions (VCs are no longer gatekeepers to funding, talent, etc), don’t need the office (seriously, sometimes people just liked a place to go work) and so on.

Sure some entrepreneurs still align with venture firms for co-development or “EIR-like” relationships but they’re not formal, don’t typically involve salary and importantly, aren’t bragged about publicly by the firms (less everyone else try to elbow into the deal). Farewell EIR….

“I’ll see in 2022 if I can turn The SF Minute into an actual business that’s somewhat sustainable”

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 started, I was really excited and it’s been a fun collection of serious and not-so-serious SF stories, links and weekend events calendars. I recently had the chance to ask Five Questions of Nick Bastone, its founder and main author. Here they are!

Hunter Walk: Ok, I read SF Minute every weekday. While the title itself is pretty descriptive on its own, how do you explain the newsletter to people and how’d it get started?

Nick Bastone: Of course. And first off, thanks so much for having me here!

The SF Minute is a San Francisco-based newsletter that highlights the top local stories of the day. Basically, every Monday through Friday, I read through all the local publications and summarize the news that I think is the most interesting and important. The result is an email that takes (get this!) only a minute or two to read.

I started The SF Minute earlier this year sort of for selfish reasons. I wanted to learn more about what was happening in San Francisco and (although we have some good publications here) I wasn’t satisfied with any particular product that brought the news together in a simple way. So, I thought I’d give it a try.

HW: You started your career at Square and Faire, before becoming a tech reporter. Why’d you leave tech reporting (for now)?!? Tech reporters with actual startup company experience are exactly what we need!!!

NB: Good question!

Having worked in tech, I do think it helped me as a reporter in some ways, like having good instincts on which stories to chase and being comfortable talking with sources from the start. But business experience wasn’t everything. At The Information, for instance, I covered Google and a huge part of that beat was reporting on all the antitrust cases the company faced. Working my tech jobs — which were mostly in sales and operations — didn’t necessarily prepare me to report antitrust law or know which DC lobbying groups I should be talking to.

As with most jobs, I think a big key to being a good reporter is tied to passion and grit and being willing to go the “extra mile” (as cheesy as that sounds). And personally, as the pandemic wore on, I found myself becoming less interested in what was happening inside Google and more interested in what was happening outside my window (aka San Francisco).

Also, fun fact, between working at Square and Faire I actually helped start a local publication on the Peninsula called The Six Fifty. It was my first “real” reporting gig, and ever since, I’ve been fascinated by the local news industry and have had the itch to get back in.

HW: My wife and I both moved out here in the mid 90s so we have a few decades of SF under our respective belts, and I gotta say, it *is* pretty depressing at the moment due to the city’s ongoing struggle with what it wants to be and political impotence. How do you think about where SF Minute fits into the zeitgeist — it seems like you are interested in moving people to action in small community-oriented ways, like the trash cleanup efforts.

NB: Early on with the newsletter, I took a pretty firm stance on the trash situation in San Francisco and was comfortable saying, “This place is a mess. We need to clean it up!” I figured if anyone was upset with me advocating for cleaner sidewalks, I’m okay with that.

But trash cleanup is sort of the one thing I’m outspoken about. Other topics I really try to play it neutral, present both sides, and stick to the facts, like any good reporter should. It’s so easy in local news to inject your opinion because you actually live here and you’re encountering the same issues that you’re writing about. But again, I really think it’s best that I stay out of it.

That said, a big part of why I started The SF Minute was to inspire positive change across the city. I don’t necessarily know what that change will be or who it will come from, but my thesis is that if I can present the news in an easy, interesting way and get more people to actually learn about what’s happening here, good things will follow.

HW: In building your readership and business, what’s one thing that’s been more difficult than you expected?

NB: It’s strange. Early on I was worried that people wouldn’t actually like the newsletter or they wouldn’t find it useful. But almost from the beginning, it resonated with people, and (since your readers will understand this, I’ll just say it) I think the “product-market fit” has been there from the start. I’ve had so many people go out of their way to tell me they “love” The SF Minute, and that’s the coolest feeling.

But even while creating something people love, user growth has been slower than I expected. In my head, I thought, “No problem, in a year I’ll have 20,000 subscribers.” And that’s just not the case. My email list right now is just shy of 3,000.

Part of that is starting from scratch. I had zero subscribers at the beginning of 2021, and I don’t necessarily have a huge Twitter following or online presence to drive a ton of growth. And I think part of it is also tied to not taking huge swings on the editorial side. I haven’t really broken that major story that then becomes the talk of the town. I’ve mostly been sticking to my news-roundup approach and growing steadily every week. It just takes time, like a lot of other creative ideas or businesses out there. And I have to constantly remind myself to be patient.

HW: Are there examples of “SF Minute” in other cities that you were inspired by or sought to emulate? Any 2022 plans to share?

NB: Newsletters are hot across the media landscape and local news is no different. Earlier this year, Axios threw its hat into the local news market and took the newsletter approach. There’s another company called 6 AM City that started publishing newsletters for second and third-tier cities in the southeast (think Raleigh, Asheville, and Nashville), and after raising $5 million recently, they’ve been expanding fast across the country. There’s also Andrew Wilkinson’s team up in Canada called OMG that has its own family of local newsletters.

Each company has its own style and voice, but the idea is the same. Again, I think it comes down to simplicity. It’s hard to get people to dedicate a lot of their time to reading local news, so it’s helpful to start with something that feels manageable (and enjoyable!), like a newsletter.

As for me, I’ll see in 2022 if I can turn The SF Minute into an actual business that’s somewhat sustainable. My wife has been supporting me on this journey, but I’ll need to pitch in financially at some point. That might take the form of advertisements on the newsletter or introducing a paid membership model, or both.

But I’m hopeful. Another thesis I had when I started the newsletter was that while a lot of people were leaving San Francisco during the pandemic, the people who stayed had a sense of loyalty about it. They wanted to learn more about what was happening in the city and why that was the case. I still believe that’s true, and I think The SF Minute is in a really good spot to help serve those people who want to make San Francisco their home.

Thanks Nick! Hope everyone signs up for The SF Minute, a free weekday newsletter about SF.

Vanity Fair’s Profile of The Rock is Just Fantastic

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 about choices they make and consistency with which they live their lives. That said, I GUESS I LOVE THE ROCK.

Writer Chris Heath and Photographer Mark Seliger do a wonderful job of summarizing what we seem to love about Dwayne Johnson, namely his drive and heart. And Vanity Fair gives them all the pages they need in November’s issue. One of my favorite passages:

The simple, empirical truth is this: Dwayne Johnson is the most successful movie star in the world, and has been for some time. For each of the last five years, he was, according to Forbes’s annual list, either the highest or second-highest paid actor. (In that period, he is estimated to have earned a total of $430.4 million.)

“It sits me down,” says Johnson, mulling this circumstance. “It sits me down. That was never the goal. The goal was just: I didn’t want to be broke. And I didn’t want my family to be broke anymore.”

and

Johnson’s friend Oprah Winfrey detects something distinctive at work here. “Most people have the ‘Do you see me?’ gene,” she says, “but he truly has the ‘I see you’ gene. And I think the reason why he’s adored is because he is adoring of other people…. He really is what he appears to be. And people know that.”

There’s a ton more about his relationship with his family, especially his father, and it’s clear that he’s human, with emotional pain that he carries.

Also, he still has zero respect for #candyass Vin Diesel.

A Tech Millionaire’s Guide To Philanthropy

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 I’ll define as actively supporting my values with dollars) has become an increasingly important part of my own goals. If you’re in a position to give meaningfully and consistently, maybe my journey will resonate for you. And I should note that what follows represents my POV/approach, some of which is shared by my wife but she also has her own style and I greatly respect that energy.

Four Things To Consider When Donating $10k, $50k, $100k+ Each Year

  1. Use a Donor Advised Fund (DAF)

DAF is a financial instrument where you can park cash, stock, and a host of other investments. You take the tax deduction when you put the asset into the DAF, and then give it away over time, letting it appreciate (hopefully) prior to distribution. It’s a really great tool to help manage appreciated private stock and offset large gains while not having to commit the donated wealth to any one particular 501c3 right away. We try to do all nonprofit giving >$1,000 from ours as well as many of our reoccurring donations.

2. Develop a Framework (or Budget)

Be intentional and consistent. Some folks set a budget — max or min they want to give away each year. I’ve never taken to that strategy, instead focusing on a three-bucket framework:

>> Support: The broadest bucket. If I see a great organization or effort, I donate $50–$250. If a friend who has skin in the game is asking me to donate to an effort they’re spearheading, $50–$250. If I read a news article that gets me mad and I can identify an organization working to solve the problem or opposed the assholes, $50-$250.

>> Support and Amplify: Basically the above but I’ll also put a limited amount of social proof against it. Whether that means via social media amplification, contacting a few friends who might also be interested or allowing the organizers to use my support in their own outreach to others (rare, but in some circles it helps to see people you know also donated). I do this for probably 1 in every 20 donations I make.

>> Committed To Your Success: The 3–5 organizations that I try to give to at meaningful levels each year — four to five figures. Besides writing a check, I’m happy to help their development and program efforts as they would like. In some cases I’ve got a relationship with the staff, in others I’m just another donor in the database, but either way, I remain consistent and step up when asked.

3. Max Out Any Employer Matching

Freeeeee money baby! Seriously, if you’re in a position to do so financially, please take advantage of any employer match. Two months left for 2021!

4. Work With Non-Profits/Beneficiaries To Leverage Your Donation

If you’re giving $1k+ and it’s not in response to a specific campaign or outreach, consider reaching out to the organization pre-donation to see if there are any opportunities coming up where your donation would be more strategic. For example, sometimes they’ll tell you about a program that has a corporate sponsor matching your gift. Most of the time they’ll be too busy to respond or just want to lock in your donation ASAP, so don’t make your contribution contingent on a conversation, but it doesn’t hurt to check.

Three Things I Had To “Get Over” To Become A Good Donor

  1. “Aren’t some problems so complex or large or intractable that giving to a nonprofit is a waste? What difference can they make?”

I’ve found that making small donations to issues such as climate, poverty and so on don’t make me think I’m “solving” the problem in one swoop but I approach them as votes for the people and organizations moving towards a better future. Don’t let the complexity of a problem stop you from taking first steps.

2. “But [charity rating organization] says this nonprofit spends too much on operations and not programs?”

There was a period where charities were initially judged by what percentage of operating budget went to direct programs versus infrastructure (headcount, rent, etc). As a blunt instrument this information was better than nothing but it’s short-sighted because it persists the dynamics which cause nonprofits to underpay staff, unable to invest in technology and other capacity building projects, and so on. So yes I want the places I donate to be ethical, hard-working, thoughtful allocators of my capital, but I don’t want them to be under-resourced and risk-averse.

3. “Seems like there are a few new organizations all doing similar things. Maybe I should wait to see who the best one is and just back them?”

Back them all. Or back one of them. Sometimes they’ll all succeed. Sometimes a subset of them will combine. I supported multiple new Get Out the Vote organizations during the last five year, sometimes with overlapping missions. Never regretted a single donation.

And finally, Two Downsides of Being Philanthropic

  1. They Sell Their Lists — Especially The Politicians

I wish they wouldn’t list trade, especially the politicians. I’ve given enough to Democratic politicians that my text, emails and voicemails usually contain messages from local, state and national candidates across the US. It’s noise and makes me momentarily annoyed.

2. It Feels Bad To Not Renew A Pledge

Per my buckets above, often I’ll give to an organization on behalf of a person or as part of a specific initiative. Often I won’t give annually to this cause unless my friends continue their involvement. Or every once in a while, I’ll shift one of my “BIG BUCKET” organizations either out of a change in my own priorities or disappointment with a group’s effectiveness. Of course I feel bad telling them I won’t be a donor again, but I’ve found it’s important that your dollars and attention are forward-looking.


If you’re fortunate enough to have gained wealth from the last decade of technology’s bull market and haven’t yet become an active donor/philanthropist please consider doing so. Thanks!

What I Tell All New VCs About Their First Funds

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 my answer is that generally while a particular zip code or two might feel ‘overfunded’ at a moment in time, that early stage entrepreneurism is still UNDERFUNDED globally by at least an order of magnitude. So yes, there is definitely room for new investors, especially if you are going to execute at least one of the two following competitive advantages: 

  1. Fund people/ideas ahead of consensus — that is, find founders and markets that aren’t currently being chased by the mainstream and get to conviction ahead of the pack.
  2. Be more helpful than the folks on cap tables today who overpromise and underdeliver — every cap table I’m on has some percentage of allocation that provided zero value after the investment. If you can be more valuable than that, I’d love to bring you on to the cap table of the next seed round we lead.

So besides those points, here are three things I generally advise folks raising their first funds…

A. It’s Not Always Worth Doing Second and Third Closes: I generally believe new investors underestimate the challenge of fundraising and investing at the same time. We had the incredible privilege to raise our first fund quickly and get focused on putting it to work, but the history of new managers not hitting their hard cap and just deciding to show proof instead is longer than you’d think. There are a handful of notable and quite successful folks who back in the day just closed what they could and got to work. Once they had momentum they raised a next fund 12–18 months later (vs the ‘normal 24–36 month cycle). If you’re targeting, let’s say, a $20m fund and can close on $10–12m but are really struggling to fill the rest, just don’t worry about it. Close the fund and get to work. You can invest relatively less per deal or go back to market sooner with evidence of your momentum in hand.

B. Take Some Risks, Even If They Deviate From Your Deck: Sometimes I see new VCs get over-concerned about deviating from the strategy they told their LPs they’d be executing. I’m a believer in 80/20 models here (unless for some reason your strategy was really wrong and you need to pivot more dramatically). If you do 100% of exactly what your deck said you’d do, I’m suspicious that you’re not being aggressive enough on responding to changes/opportunities in the market. If you do 0% of what was in your deck, well, then you don’t really have a strategy. But early on our LPs reminded us that they were outsourcing their judgment to us and fundamentally trusted the decisions we’d be making. This gave us the license to stretch every now and then towards an opportunity which didn’t exactly fit our model but was a calculated risk.

C. Focus On Quality Of Pick, Not Absolute Ownership, But Try To Stay Within Your ‘Weight Class’ As Often As Possible: Ok this is really inside baseball but it’s important to set up your second and third funds, which are often raised on perceived quality of Fund 1, since it’s before actual results are delivered.

Generally assuming most first funds are preseed/seed, I think of them as writing checks within a particular ‘weight class’

Supporting Checks of $50k-$250k for <5% ownership

Supporting Checks of $250k-$750k for 3–10% ownership

Lead/Co-Lead Checks of $750k+ for 8+% ownership

These are obviously all estimates and ranges but you can think of a basic cap table as a pyramid where there might be a lead or co-leads, then a bunch of supporting checks of various sizes. As a new fund you’re pitching LPs that you’ll be investing in a certain number of companies over the lifetime of the fund, usually with a check size range and/or initial ownership target. You also might be holding some reserves for follow-on in future rounds for your most promising investments.

I’m going to make that case that in your first fund what you’re trying to prove is that you have good picking and access within your weight class. You are not trying to prove that you can always hit the high end of your ownership target, at least not to the detriment of quality of pick. You are also not necessarily trying to show that you can manage a great reserve strategy, although doing so successfully can help your returns, and as your funds grow larger, you’ll need to develop this skill.

Why am I saying it’s better to get in at the low end of your weight class target than pass great opportunities by? Because (a) great companies dramatically outperform good ones and (b) LPs will believe that more capital (ie a larger Fund 2) will help you get more allocation within your weight class and deploy follow-on dollars. They won’t believe that more capital will make you a better picker! That is, the argument that because your fund was small and you held to hitting certain ownership targets you were limited to average companies is a losing strategy. Now it’s still quite important to stay within your weight class or at the top of the one below yours. LPs will generally believe that if you got $250k into companies on average in Fund 1 (and the companies were solid and your references are positive) that you’ll be able to get $350k, $450k, etc into companies if your fund was a bit larger. Or use those additional dollars to hold your ownership in one or two successive pro rata rounds. They will raise an eyebrow if you are trying to move from a Fund 1 of $50k checks to a Fund 2 of $2m ones. It’s just a different slot on the cap table, a different fund operations model and a different competitive set.

There’s a lot of nuance still in the interplay between check size, ownership and portfolio management. There’s also the aspect of sometimes needing to hold your ground on your ask. If you develop a reputation for always taking the least offered to you, well, even a nice guy like me will push you down in rounds so I can get mine.


I’m always open to helping new managers and my contact info is available on www.homebrew.co. Also, I’m part of an effort called Screendoor which helps back emerging managers from underrepresented populations. The future of VC shouldn’t look just like me. If you’re raising a fund feel free to check out Screendoor and see if we’re a fit for you. Good luck!