“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.