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 that effort matters (alongside ethics) and, ahead of the ‘growth mindset’ being academically coined, believed that with enough focus on a goal, I could probably get closer to achieving it. And now as a parent myself, we work to instill similar values in our daughter. Given this, why do I also now ascribe ‘luck’ (and not just my own attributes) as such a significant factor in my own success? Not because I’m less secure in my abilities, but because I’m more expansive in defining what luck actually means.
In my understanding now, luck isn’t about removing the notion of self-determination, or suggesting that everything which happens to us is just a random number generator. Instead my luck is a set of circumstances that I was gifted and which created the platform upon which I built my life. This includes: Where and when I was born; my health; the cultural, ethnic, socioeconomic benefits; and so on. Sometimes it’s not about what you have (I wasn’t a silverspoon kid) but what you didn’t have to deal with (I also wasn’t born into poverty).
Looking at luck through this lens also shapes a notion of ‘paying ones luck forward.’ Can you find ways to help replicate your luck for others? Looking at someone who is beginning their career without some of the benefits we had and helping to give them a break. Believing that effort is required but sometimes not sufficient for an individual who needs some mentorship or help in where to direct their energy. Or that helping someone early on in their career with a ‘lucky break’ (an introduction, a part-time job, etc) will compound for them, versus just leaving them to their own devices and assuming Darwin will sort it out.
“According to the Pew Research Center, people in higher income brackets are much more likely than those with lower incomes to say that individuals get rich primarily because they work hard. Other surveys bear this out: Wealthy people overwhelmingly attribute their own success to hard work rather than to factors like luck or being in the right place at the right time.”
Ok, but why does this matter? Because it impacts the decisions we make about how we help (or don’t help) others:
“That’s troubling, because a growing body of evidence suggests that seeing ourselves as self-made — rather than as talented, hardworking, and lucky — leads us to be less generous and public-spirited. It may even make the lucky less likely to support the conditions (such as high-quality public infrastructure and education) that made their own success possible.
Happily, though, when people are prompted to reflect on their good fortune, they become much more willing to contribute to the common good.”
So my hope is that those of us who are successful, can also realize we’ve benefitted from *some* degree of luck, and work on extending that luck to the greatest number of people possible, since that perpetuates the dynamism in society we’ve come to appreciate. Best of luck…..
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 about his thought leadership which seemed to be 80% “that’s smart” and 20% “what did you just smoke because I have no idea what this means?” Sometimes I’d just DM him the latter with “20” written alongside. But outside of this social media sparring, is a foundational friendship where I hold him in high admiration, not just professionally but as a human. He’s an expressive, passionate, principled person who cares deeply about his family and his community. So I used this Five Questions to get a bit more on his own background and push on web3 developments now that he’s slinging million dollar investment checks as part of The Chernin Group. Thanks JD for always being a good sport!
Hunter Walk: So you recently moved over to the investing side leading Crypto at The Chernin Group, but before we dive into your annoying web3 tweeting habits, let’s go backwards a bit. You did a lot of work in online advertising but also seem to really care about people and user experience. Reconcile that for me!
Jarrod Dicker: I started my career as a music journalist and the plan was to do that forever. I love music but am pretty shitty at playing instruments (though I collect guitars!). So the closest thing to becoming a rock star for me was writing about them. I had a blog and did a bunch of freelance work while bartending at night in Jersey, and in 2010ish accidentally fell into the media world by applying for a job on Craigslist at a blog called the Huffington Post. I wanted a writer role but the only thing they had was a business role aimed at trying to think of creative ways for the Huffington Post to make money outside of traditional means. That’s where I realized that if you like to be creative, the business side is actually way more liberating than the editorial side because you effectively could experiment and do whatever you want as long as you made money. It was permissionless as long as you delivered.
At the time it wasn’t as obvious as it is now that the bar for monetizing media and publishing was insanely low. So I carved out an ethos that whichever way the wind was blowing on the business side of media (programmatic ads, etc.), I would argue, develop and build an opposite approach. That worked out for me over the past decade. We created the Native Advertising model at HuffPost, developed new ways to build media businesses in the social era at RebelMouse and created two SaaS businesses at The Washington Post. The story is often as important (if not more) than the product itself, and in the media business taking the approach to build better experiences for consumers and new profit streams that support the core value of the projects wasn’t necessarily revolutionary, but it was an opposite approach that the industry could get behind. I like to try and enforce a beginner’s mindset in everything I do.
HW: I also associate you with a love of music, especially songwriters, jam bands and live performance. Is this an escape for you from tech stuff, or do you see parallels between Software Jarrod and Phish Jarrod?
JD:Maybe so, maybe not. But seriously… Music is definitely the best representation of me. My identity is directly connected to it. I was fortunate growing up in a family that believed in the importance of having music around 24/7. My mom was a dance choreographer and owned three studios in central Jersey. In those days, you would get your music at record stores and I remember her making it a weekly thing for us to go to Jacks in Red Bank or Coconuts in Sayreville and just buy everything off the wall. Because she owned studios, CDs were a business expense so I had a full go on everything.
It’s wild to think about the 90s because you would hear a song on the radio and try to find it or would go to the record store and buy a CD for a single song and discover the rest of the band through the album. Anyway I’m ranting but it was a very fucking cool way to discover something new. Everything felt new and hard to find, and when you found something special it was always an incredible feeling.
The parallels of music head and tech head are that when you’re constantly in a chase for something new, you have a different chase on things that often others can’t feel or see. Unless you know the feeling of the chase, you don’t know what you’re hunting for. I think it’s important in tech to try to constantly think and find something new. To understand that many people feel or see different things, and the importance of being open to a bunch of different flavors and sounds. Maybe the word I’m looking for is openness. Or maybe it’s like being in a dark room and feeling for the light switch and that moment when the lights turn on and you see everything in front of you. Anyway, go see Phish live. You’ll understand.
HW: Were you a well-behaved kid or pain in the ass kid?
JD: What do you think? 😉 I would say I was a loud kid. And when you’re loud, you are often unfairly characterized by your teachers as a pain in the ass. School was interesting for me. I loved it, but more so because I love people. I wasn’t a great student, but I wasn’t a bad student. I liked the things I liked and spent most of my time there. I am not a loner and definitely, if you met me, not an introvert. I’m all about being on the move and want to constantly be surrounded by people. I’d say the things that used to get me in trouble back then (social, loud, on the move) are the things that make me successful today. So I’m happy I didn’t listen to those teachers.
HW: Ok, now we can do two questions on the web3 stuff. Knowing what you know now, was Po.et (where you were CEO several years ago) just too early or would you have approached the project differently?
JD: I think it’s definitely a little bit of both. We were definitely too early. It’s crazy because if you think of the pitch back then (“we want to put all digital content on chain”) it sounds like a billion dollar idea today. But back then it just wasn’t as clear to creators and consumers. The emphasis was really anchored in the notion of provenance; in an era of fake news, deep fakes and attributing quantifiable value to quality content, having a supply chain of information could provide a base layer to build products that solve for that. But the market and our approach wasn’t yet ready. We also aimed to do it on bitcoin which in hindsight would have eventually shifted to ethereum or another L1 quickly.
We also aimed to get big publishers on board. New York Media was incredible and took a bet on us, integrating the protocol into their CMS. But again, others weren’t yet ready. Looking back, I would have leaned heavier on attributing value and ownership to assets over having a supply chain of creative process. I also would have focused more on the long tail than the short tail. We had a highly active community of developers that were building the function of Po.et in their creative flow. There are projects today that have executed a part of that vision and have taken it a lot further that I’m insanely excited about. But in the end, Po.et got me technically very deep in the crypto space and much of the relationships, learnings and lessons are the reason I’m doing what I’m doing today.
HW: One criticism hurled at web3 devotees is that it’s a bunch of pronouncements about decentralized, liberated futures that are just disguising a greed to make money. How do you feel about those opinions, given that you’re specifically in the business now of making money off of web3?
JD: There are some parts of web3 that I believe are hard to argue. One of the biggest, and most important, is that the emergence of NFTs has brought provable digital ownership to the internet. This evolution can’t be overstated. We’ve spent decades building products on the internet with the presumption that most digital content and IP can’t be proven scarce, or valuable, or 1:1. Now we can. So not only are we seeing an emergence of new platforms and products driving this, but also seeing many existing companies starting to think about what that now means for their business and experiences on the internet.
It’s actually funny because in the 2010s social world, the challenge was the there were all of these users but no way to monetize them. Now we have all of this monetization, and are looking for users. Matt Huang has a great tweet here .
It’s so new, and we’re taking a different approach to getting to a new space. What the term web3 has shown us is we’re now seeing crypto or blockchain in every pocket of the web. Every industry. Every interest group. So it is going to take time and experimentation to see how that fits in to both existing paradigms and newfound ones.
A part of it being focused on the creator space makes sense. There are many creative businesses that don’t have a strong online economic foundation (digital art, photography, dance) and face little headwinds. If the opportunity is in web3, then we’re starting to see how this comes to life organically. I also think it’s not binary. Arguments are also “why do you need web3 for this?” and maybe the question to ask is “why are we using web3 for this?”. Having a new option to own and distribute IP is amazing for both creators and consumers on the web. If they choose to use it, and prove it’s opportunity, then we all win.
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 the work you’re intending to accomplish, or are drained of energy by what (and who) you’re spending time with, perhaps looking at your schedule is one way to solve. I’m pretty fortunate that I’ve got more control of my day than many people on a more traditional company org chart, but I also believe that creating boundaries, saying ‘no’ more often, and so on, is a good way to reclaim your space. Here are a bunch of replies I used in December to say ‘no’ to requests for coffees, ‘picking my brain,’ sales calls, and so on. Copy and paste if you’d like. And share your favorite ‘kind declines’ with me on Twitter 🙂
Know that if you’ve received one of these from me, I’m not minimizing the credibility of your ask, or otherwise trying to suggest my time is more valuable than yours. But rather, time and energy is so scarce, that I’m very deliberate about where I’ve committed it, and Homebrew, Screendoor, and my family, are where it goes.
“I’m sorry I just can’t prioritize that right now but best of luck.”
“I know you’re not asking for a lot of my time, but I need to concentrate on getting some projects done and can’t let myself be distracted right now. Best of luck.”
“If you can provide some specific examples or questions you think I can be helpful on, perhaps I’ll be able to answer them here and we don’t need to worry about chatting live.”
“Can you provide a little more detail over email so I can make sure I’m a good use of your time.”
“I’m holding all my scheduled time back right now for our portfolio founders (and my family) but if you reply with some specific questions, I’ll do my best to answer via email or a Loom video if I think I can be helpful.”
“Thanks and appreciated meeting you as well. Don’t feel like we need to chat live right now but feel free to stay in touch.”
“I know this sounds weird but I’m only doing these sorts of conversations in 15 minute phone calls between X-Ypm on [days of the week]. I’d be happy to chat then if you still think it’s worth your time. Here’s my next availability…”
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 fortunate the number of founders I’m impressed by far exceeds our investment capacity. Here’s an example of a founder that I’ve known for a while who recently raised a seed round with different firms than ours. In industry terms, I’d call this a “miss/loss,” which VCs tend to not write about for obvious reasons (I’ve got a whole other rant on the fake performative anti-portfolio lists — Bessemer’s aside). But Satya and I post-mortem our miss/losses so I figured, why not do a version of it in public? My friend Alex at TechCrunch covered Shepherd’s seed round last September and here’s some more detail on how it all came about via my Five Questions with their cofounder/CEO Justin Levine.
Hunter Walk: Justin, thanks for agreeing to do this. I really enjoy our conversations and am especially glad you’re up for some candor, because it’ll help provide some insight into the state of the startup and funding market. Ok, first, let’s provide some backstory. You want to tell people how we originally met?
Justin Levine: Sure! Homebrew was on the board of a construction tech startup called BuildingConnected, having led their seed financing. BuildingConnected’s first and only acquisition was a company I founded called TradeTapp. Our team joined BC in 2018, and less than 6 months after that BC was acquired by Autodesk, where I continued on for about a year. As I started to explore new ideas, Dustin (DeVan, CEO of BuildingConnected) made sure Hunter was one of the first investors we spoke with.
HW: So then you ‘did your time’ at Autodesk post-BuildingConnected acquisition. What did you learn from the two acquisition experiences, and the whiplash of going from small startup -> bigger startup -> big public company that quickly?
JL: In short, a lot. I was pretty naive going into my first startup, having worked in more “traditional” roles within the construction industry prior to founding TradeTapp. I certainly didn’t know a ton about venture capital or the tech industry at large. I think BuildingConnected was eye opening because of how truly BIG the idea was — much bigger than what we had been chasing at TradeTapp. At BC, our products were SaaS tools, but they were just a wedge into something bigger. What we were really building was the first professional network for all of the $10T construction industry. If done right, the opportunity was enormous. Pretty cool! BC taught me to dream bigger, and to experience startup at scale.
Post-BuildingConnected things definitely changed. This will sound like a shot at Autodesk (it’s not meant to be), but what I learned from my time there is that acquisitions are incredibly hard and come with many unavoidable challenges. It takes a tremendous amount of effort to remain customer focused — something we often struggled with. This article from Noam Bardin (fmr CEO of Waze, acquired by Google) articulates some of the impossible choices large corporations have to make when integrating acquired startups, and a lot of his perspective certainly resonates with my experience.
HW: You and I had lightly stayed in touch, but reconnected when you started work on a NewCo. The original idea was novel but not one that we had great conviction around, so we held off investing but wished you luck, Then you returned to a problem space you knew well and started Shepherd (commercial insurance for construction). In March 2021 I reach back out based on a LinkedIn bio change you made (my CRM is mostly in my head) to learn more. We chat in April, find out that you’ve already raised a pre-seed round and are building towards a seed. Where did I f*** up? aka how come you didn’t come back to us for the pre-seed knowing that (a) we all got along and (b) we have some relevant fintech/insurtech experience ourselves?
JL: Ha! I wish I had a better answer for this one. The truth is that we were preempted by Susa about a month after starting YC W21. YC specifically tells you not to engage with VCs mid-batch, but given the long(er) road of setting up a neo-insurance carrier, we felt like we had extenuating circumstances and ultimately they were supportive. Susa has a strong track record in fintech / insurance (Newfront, Robinhood, etc.) and we also had a great relationship with the partner. Courtney pitched us as much as we pitched her. In retrospect, I think we were a bit fatigued from the unsuccessful fundraise attempt with the previous idea (it wasn’t just Homebrew that said no) and perhaps we lacked the appetite to shop the deal around even though we may have had the opportunity to do so. Susa was pretty aggressive in getting a deal done quickly, and the whole thing was over in a few days. I can’t say we have major regrets here though — Susa has been a great partner.
HW: Ok, we’re really going inside baseball now. The seed round gets done with a surplus of demand — I mean you’re a second time founder working in an area of expertise that is a huge market. We’re talking with you about the round but it’s growing beyond Homebrew’s comfort zone given our own fund size and strategy. Share how you thought about this round — doesn’t have to be specific to me/Homebrew — which ultimately shaped the decision you made about composition? Is it driven by size of round you want to raise? The needs of the lead investor for ownership? A round that is most accommodating for the existing investors while allowing you to get new people involved? You’re trying to balance a bunch of trade-offs and needs of different parties.
JL: There are definitely a number of considerations for us when taking on any outside capital, and some of them are round specific while others are just our philosophical approach to fundraising. Of course, the current state of the financing market dictates a lot of behavior as well. As you said, we’ve been operating in a pretty founder-friendly environment if you meet a few criteria such as operating in an area of expertise, and having a successful exit under your belt.
At seed, we cared deeply about the partner leading the deal: what’s their background, what’s their standing within the fund, how are their references coming back, and finally: are they on the ascent in their career (i.e. how much will Shepherd’s success mean to them beyond financial outcome). Next would be the fund itself: reputation, expertise (early stage vs. multi), and market experience (fintech/insurtech). This framework helped narrow the field for us a lot, and from there deal terms were probably the next most important thing.
We were pretty open minded regarding round structure, but the dynamics of raising at a higher valuation, which we pushed for, meant that the lead was going to need a pretty large percentage of the round in order to maintain their ownership target. With that in mind, we wanted to make sure we had room for at least one strategic partner that we felt would create an advantage for the business (in our case it ended up being two: Procore & Greenlight Re) with the remainder allocated to angels. Everyone got squeezed down, and there were definitely more than a few tough phone calls. All of this added up to a bit of a larger seed than we expected ($5M), but we were still really happy with the outcome. Natalie at Spark Capital, who led the round, has been everything we were looking for and more.
Despite all this, it’s really tough to turn away the potential to work with amazing people like you and Satya. I think these things tend to work out in time, though. My takeaway on financing is that you have to make the best decision based on what’s best for the company and team long term — and sticking to a concise plan around timing and evaluation framework was extremely helpful in ensuring it came together successfully.
HW: A nice peek behind the curtain for folks on what these rounds can be like when it becomes a “consensus” deal. Returning back to what really matters — actually building a company — what are one or two things you’ve done differently the second time around when it comes to the first 12–18 months of Shepherd?
JL: Applying my first learning from BuildingConnected, Shepherd is a much more ambitious idea than anything I’ve ever done. Our mission is to make construction, one of the most hazardous industries in the world, safer and more financially sustainable — that’s why we come to work everyday. The “how” is by creating innovative insurance products which incentivize contractors to adopt new technologies. We’re positioning Shepherd to have potential for enormous long-term impact across commercial insurance, and I think the BIG dream this time around is attracting some of the best talent across underwriting, product, and engineering to join us. It helps to have two extremely accomplished two co-founders that people immediately gravitate towards as well, and I absolutely love the team we’re building around the 3 of us.
On a more personal level, I’ve matured a lot as a leader since the first days of TradeTapp. I try not to ride the emotional wave of startup life like I sometimes did before and rather be a consistent source of calm for our team, co-founders, and investors. I view a huge component of my job as making sure every employee is in the best position to succeed in their roles. I pay a lot more attention to what everyone is optimizing for individually, and aligning their personal goals with the company goals. From TradeTapp, I learned it’s easy to take these things for granted only to realize later that not everyone is pulling in the same direction.
Finally, there’s been a pretty significant change at home…I’m also a recent Dad! My son was born just about 2 months after we founded the company. The days of the company being the one singular focus in my life are over. But there’s a silver lining to that: I think having a baby at home forces a different level of focus and decisiveness around the way I operate. Being a second time founder, you’re able to peak around a few more corners and avoid some of the dumb mistakes you made the first time. It’s not always perfect but I can say confidently that the lessons from building something a first time are invaluable to the next.
Well there you go, the story behind the story on how rounds get done for companies which have heat on them. I’ve found that seed these days really is two different worlds: founders who have no trouble getting multiple termsheets within days of fundraising at valuations we used to assign to A rounds, and of course more commonly, those who find that it’s a constant struggle to get investors to believe in their vision and take a risk on them. What’s interesting here to me is our involvement in Building Connected was the latter (cold email from two founders), and one of their alumnus turned into the former! Thanks Justin for sharing a bit with me here and best of luck.
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 meant for them as kids. Projecting from my own personal history? Sure. But it does lead me to ask peers about how they first encountered, and committed to, software. As a longtime Facebook engineering leader and now Meta’s new CTO, Andrew Bosworth has been at the center of many decisions Facebook/Meta made in the last decade, so I decided to ask him Five Questions.
Hunter Walk: For me, two formative moments with technology occurred pre-adulthood: Print Shop on the Mac and Alt.Net newsgroups. The combo convinced me that software was for creativity and community — 100% impacted the rest of my life. Do you have any “AHA!” memories of your own with regards to tech?
Andrew Bosworth: In two words: video games.
My parents got an Apple IIe when I was around 5 and a game called Rocky’s Boots which entailed chaining together logic gates to solve puzzles. The discovery of logic gates really changed the way I thought beyond just the game which is pretty profound for a five year old. I also liked Sticky Bears and Lode Runner.
In middle school we got a DOS PC and a friend from 4-H came over and introduced me to QBasic programming and we built a basic program where you could use the arrow keys to change the color of the cursor. It felt like magic. From there I could see how all the games I liked (Sim City in particular) were really engineering problems at different levels of scale.
Then in high school I started playing multiplayer games with my friends (Descent 2, mostly) which initially meant dragging them around and physically wiring them together and then eventually dialing in to each other’s modems directly. Combined with occasional prodigy usenet experience (I recall a few Star Trek MUDs) it really gave me the feeling of being socially connected when I was otherwise on my own at home. I was a very social kid (constantly on email/AIM or corded phone) who lived on ranch without many friends in walking distance so this was meaningful.
I do feel lucky to have been raised in Silicon Valley where it was clear to everyone that this was a very valid and potentially lucrative career choice. Within computer science, the thing I set out to study was artificial intelligence and the main reason for that was playing Metal Gear Solid at my friends house (I never had a console, just the PC and a gameboy), the first game I played where the “AI” (quite simple in retrospect) was a major factor of the gameplay. We spent more time making the guards follow us around by leaving clues than we did on the game sometimes.
HW: Did you collect anything as a child? I went through overlapping phases of baseball cards, comic books, old wrestling magazines, role playing games, paraphernalia and old books. You as big a nerd as me, or nah?
AB: Not seriously. While I enjoyed video games at home and did some RPGs with my cousins at holidays, I was an active kid and spent most of my time outdoors playing sports or just hiking around (I grew up in a rural area of the Bay). I had a half-assed Magic card collection and an even more limited baseball card collection. I lived in a rich area (my family was comfortable but nowhere near the same level) so the kids who were into those things had incredible collections I knew I could never match so it never seemed worth investing much. In fact I didn’t really collect anything seriously until my mid-30s when I started collecting camera lenses and I suppose now a little bit of art.
HW: You grew up out here but went east for college. Had you traveled much prior to that change? Did Boston work for you right away or was there an adjustment period? Is there an alternate future where Boz didn’t return to California?
AB: With only one exception (visiting my aunt and uncle in Hawaii) every vacation we took as a family was to pile into the car and get to the great outdoors. Every Easter break and summer we were camping or backpacking somewhere here in the American West, from Baja to Oregon and as far east as New Mexico. We did go up to Tahoe in the winter sometimes so I was plenty comfortable in the snow. I expected to go to a UC like everyone else in my family had but a few schools encouraged me to apply, hinting they might tag me as a football recruit. In the end, none of them did but I had already applied and then managed to actually get into Harvard (but not Yale or Stanford). I still almost went to UC San Diego but figured (correctly) I would probably spend the rest of my life in California so it would be good to branch out for a few years.
Boston was great and is an easy city to like with great public transit and good institutions. I really enjoyed my time there and it helped that my sister was already living there coaching rowing at Harvard. Still, there was never any chance I would stay on the east coast. I admit I also enjoyed the year and a half I lived in Seattle after I graduated but at some point I knew I would be back in the bay. My family has been here for five generations on each side, my loyalty runs deep.
HW: You proposed to your wife on the peak of Shasta after summiting the mountain together. My man, can you not make it hard on all of us who got engaged at sea level! How did you two originally meet?
AB: I was playing a pickup rugby game as an undergrad and injured my shoulder. University healthcare is awful so once they confirmed I wasn’t pregnant they proceeded to misdiagnose the injury for several years. It would dislocate quite often in my sleep which is an alarming experience to say the least. When I finally got a job with decent healthcare at Microsoft the first thing I did was go to a specialist who confirmed I needed surgery to repair a tear to my Superior Labrum.
After surgery I did my physical therapy at The Pro Club where I was randomly assigned as the patient of my future wife. I rolled in wearing all Harvard themed athletic gear (I didn’t own anything else!) and she rightly made fun of me for it. We ran into each other socially a few times at bars in Seattle but I feel compelled to note we didn’t date at all until after I had completed my treatments. Neither of us agrees on who initiated the relationship but it was her.
HW: One of my favorite episodes of This American Life is about superpowers, and one of the segments is John Hodgman asking folks whether they’d prefer the power of flight or the power of invisibility. So, Boz, I ask you: flight or invisibility?
AB: Flight. Invisibility can basically only be used for subterfuge as far as I can tell? That’s not my style. I’m comfortable not hearing conversations not intended for me. But I’m very impatient and travel consumes a huge amount of time so flight is a big win.
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 coffee this past summer. I really enjoyed that chat so wanted to learn a bit more about my new friend, as well as share her story with you all. Thanks Ellen for answering Five Questions.
Hunter Walk: During my childhood I went through phases where I thought I’d be a writer, or a lawyer. Were there professions you recall thinking about when you were a kid? How connected are they to what you’ve ended up doing in this first phase of your career?
Ellen DaSilva: When I was 5, we had career day in my first grade class. Each student had to say what they wanted to be when they grew up — a pretty cliche exercise given I didn’t really know much about the professional world. I thought about it, and announced to my class that I wanted to be the CEO of Coca Cola. Not a soda drinker myself, but when my teacher asked why, I said I knew I’d be the leader of an iconic American company.
In reality, I had limited visibility into the world of tech and entrepreneurship until after college. It seemed to me that the way to achieve success was to work in the financial services or in a blue-chip business. It was sheer luck that I got placed on the tech desk at Barclays and met my (now husband) at the same time. Both showed me that there was life beyond large financial services institutions, and it clicked instantly.
All of this is to say that young aspiration, while it had nothing to do with my current job, gave me the footing to be open-minded, ambitious, and strive until I reached what I wanted. It’s that kind of attitude that helps no matter what the industry.
HW: Over the last decade you worked in banking, then Twitter and Hims (which you recently left). Is there a framework you’ve used to decide when it’s time to leave a company, and how to decide what to do next? I think many new grads would be happy to mirror your early path!
EDS: My mom always told me “don’t leave a job, run toward a new opportunity.” There is a lot of truth to this. Every 3–6 months, I run a mental exercise in which I ask myself the following questions:
Am I happy with how I’m spending my time?
Am I still learning and growing?
Am I being given increasing responsibility?
If the answer is no to any of these questions, it’s a valuable moment to assess whether any of these vectors can change. If they can’t, or if something is misaligned, then it’s time to more seriously consider other jobs.
For me, it has always boiled down to honesty with my manager specifically each time I was ready for a transition. For example, I got lucky when I was an analyst at Barclays — truly a junior-level employee. My manager and I were very different, but I felt comfortable having frank conversations with him that it wasn’t the right career for me. He was supportive when I needed to take interviews at tech companies, and offered his rolodex, recommendation, and anything else I would require. That level of mutual respect when you are looking to leave a job is critical.
The world is small and we cross professional paths with people we’d least expect. So the most important thing is to leave with dignity and integrity. I try to do that every time, even if the job is no longer the right fit. I emulated that experience when I left Twitter for HBS, and when I left Hims to start my new venture. I feel grateful to have the support and blessings of my former colleagues.
HW: Both Twitter (IPO) and Hims (SPAC) went public during your tenures. Were there similarities in how it felt to live through those moments? Was there anything either company did to try and maintain focus on building & executing vs “where is the stock price today?”
EDS: It’s funny — I started my career in investment banking working on the Equity Syndicate desk taking companies public. I used to work on multiple IPOs every week, so it didn’t seem like such a big deal. It was only when I worked at Twitter that I realized how momentous a public offering was when you’re at an operating company. I had been at the company for about 2 years when we went public in November 2013, and the feeling of euphoria was palpable at 5am when we got to the office to watch the management team ring the bell on the exchange.
The differences between the two IPO experiences were fairly stark. To state the obvious, Hims went public in January 2021, before most of us had vaccines. Watching the stock exchange open with your colleagues on Zoom is a very different kind of celebration. Joyous, but more muted. We never had a proper celebration until we could all be together again.
There were plenty of similarities in these milestones: the feeling of extremely hard grind, followed by a brief moment of pause to celebrate, followed immediately by the feeling of “back to work.” These are two businesses that have an ingrained culture of working hard, so we had the sense that the IPO was the beginning of the next chapter rather than the end.
Maintaining focus became a quick post-IPO shift for both businesses: at both Twitter and Hims, we immediately prioritized ROI, cost-cutting and laser focus on the pre-approved roadmap. Inevitably, there is less room for experimentation when public scrutiny from investors increases. So we saw a bit of that happening as well.
HW: What’s one effort to support ‘women in tech’ that you think is ineffective and what’s one effort we should collectively 10x?
EDS: This is an area that’s extremely near and dear to my heart, and I’ve been passionate about spending time throughout my career working to combat gender inequality. I’ll caveat everything I say here by expressing that when I’m talking about women, I’m referring to broader women/womxn/non-binary/those who identify as female.
There are so many aspects of the system to help women that are broken. If I had to pick one, I’d say that mentorship programs are the biggest fallacy in making any real change.
For starters, mentorship has to be organic. To artificially pair individuals with someone their senior leads to a pretty mediocre experience. Both sides are looking for a spark but may lack some fundamental connection (Shared job function! Shared experience! Shared outlook and desires!). Mentorship is also a two-way street. There are plenty of people who would consider me to be their mentor, and vice versa. I also have peers who are also my mentors.
Second, women’s mentorship programs almost exclusively feature women-to-women pairings. Why is that? If anything, I’d like for a senior male to show me insight into how they got where they are. I’d like to mentor more men in their careers so that they can have a female aspirational role model to show them how to get things done. It’s not the responsibility of the minority to demonstrate their value to the majority. We shouldn’t gate it.
Finally, the whole concept of mentorship is rather blunt unless it happens naturally. What I really encourage young women to find is a sponsor. Pick someone who will say “I’m going up, and you’re coming along with me.” That’s how real mobility happens.
HW: You and I are both relatively outspoken about our personal political beliefs (even if we’re happy to work with people who disagree with us). Have you always been engaged in this area or was there a particular moment that pulled you into the conversation?
EDS: This is an area of my life in which I have been deeply consistent. Emphatically yes, I have always brought some of my politics to bear. I’ve been an active and avid Democrat my whole life. My parents instilled in me from a young age that integrity and fighting for what you believe is the best way to spend time on this earth, so I always interpreted that as supporting worthy political causes.
When I entered college in the fall of 2006, I worked for Hillary Clinton’s 2008 presidential campaign, at a time when it wasn’t exactly so popular to do so. I was very outspoken on campus campaigning for her, and it felt good to be honest about what I stood for and the belief system I possessed.
I have a distinct memory of interviewing a candidate for my team when I was at Twitter. At the time, I had my Hillary Clinton work on my LinkedIn. When he asked me about it, he started with “you’re never supposed to talk about politics or religion in an interview, but here goes…” and it was one of the best candidate conversations we’ve had. It turns out we aligned politically, but I’m all about finding discourse even among disagreement. It’s fine to disagree, as long as we keep things civil.
During the presidential election of 2020, I couldn’t hold my tongue. With thanks in large part to friends like you, Hunter, we hosted a series of fireside chat campaign events via Zoom. I was surprised to see a number of my work colleagues attending those events, and received support from all walks of life along the way. I’ll keep doing this as long as I have a perch to do so.
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]
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.
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.
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 fiercelydebated. 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.
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:
‘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.