As always, I connected with Aashay on Twitter. We met over the summer last year when I was working at
and he was working at Breather. He has worked with a bunch of startups and venture capital funds including NEA. He is currently working with NYC based Notation Capital while studying at Harvard.
He is very well informed about the product landscape across industries. He is an extremely knowledgable fellow who has well thought-out views on a lot of topics that he always backs up with additional context.
In this wide-ranging interview, he talks about how Twitter has helped him in his career, why starting in venture capital might not be a good idea, misconception about people who go to Harvard, opportunity cost of focusing too much on crypto, his thesis around AWS of hardware, his thoughts on trends in real estate, healthcare and enterprise collaboration spaces, and more.
How do you define Twitter ? It is a pretty frustrating experience when you are new to Twitter. What would you recommend doing to those who are starting out to understand why so many of us love Twitter?
I define Twitter as a medium through which I can explore my interests, keep up to date with news that’s most relevant to me, disseminate my content, and follow the thoughts and opinions of people I find appealing in industry and academia. I agree with your premise that Twitter’s onboarding is kind of terrible. Honestly, I’ve used Twitter in a meaningful way for a years, but it’s taken time to get it to where I feel like I’m really maximizing value from it. I would say that it requires some sort of patience. Every day, I feel like I find someone new that a bunch of cool people I know follow and I’ll never have known about that person before. As an aside, it would be interesting if certain Twitter power users (such as yourself) could recommend a list of X people to follow if you’re interested in Y category. For example, follow these 25 VCs for thoughtful insights on venture capital or these 25 product designers if you’re into design. Essentially Twitter lists that are shareable and actionable.
How has Twitter helped you in a meaningful way in your career?
I would say it’s been helpful in three main ways. The first way is that I’ve been able to track (over time) the ways in which tech and VC thought leaders have developed their opinions. People who were saying the sharing economy was the future a few years ago are now saying it was doomed to begin with. Why is that? What is it about this industry that makes people hold fickle opinions? Lots to learn on that front. The second way is that Twitter has democratized access and engagement. I’m able to jump into conversations with people I admire and connect with them in meaningful ways. Finally, Twitter has been a great way for me to develop my own thinking. It’s a public timestamp for most of my thoughts on technology and startups. It’s always interesting to see what I’ve tweeted over the years and think about how my thoughts have changed.
Imagine you are the head of product at Twitter. What would be your top two or three priorities this year?
If I were head of product at Twitter, my top two priorities would be probably be around ad tools for SMBs and somehow rewiring onboarding. Ads still kind of suck on Twitter, but I think Instagram has done a great job of allowing small businesses to leverage their platform. Scott Belsky has a nice post on this. Additionally, everyone complains about this, but the initial Twitter experience is sort of terrible if you don’t know what you’re doing. In terms of onboarding I like recently, check out Panda.
You go to Harvard. What part of the narrative about the kind of students who go there is overblown? What’s lesser known? What role do you think elite institutions will play in the higher education landscape next twenty years?
I would like to dispel the narrative that Harvard students are spoiled, entitled brats. You’ll meet jerks everywhere you go, but most people I know here are some of the nicest and most genuine people I’ve ever met. Much more so than my high school. Harvard is unique in terms of its financial aid policy, and it’s a little known fact that over 50% of students here are on some form of aid. The socioeconomic diversity of the classes is improving, and I think that’s a huge plus. The biggest benefit you gain from Harvard is not the academics, but rather an investment in your own human and social capital. The network and doors it opens are great, but it’s really what you make of it. In terms of learning more about elite institutions, I would recommend the second chapter of Malcolm Harris’s Kids These Days. Today’s modern university has a corporate complex, meaning that rising tuition costs have not gone to support faculty and teaching, but rather overhead and administration. With that being said, the Harvard brand has incredible staying power, and I do think it’s further away from being ‘disrupted’ than people think.
Let’s talk about VC & banking now. You have a lot of experience working in venture capital. VC seems to be a cool gig these days. Make a case for why working at funds could be a bad career choice.
There’s a few ways jumping into venture investing early on can go haywire. If you’re early stage, you aren’t picking up many skills that are transferable elsewhere. Most of early stage investing is meetings/calls along with analysis of teams and early products. There isn’t a ton of structure, and you don’t build a large immediate network from within the firm as you would if you joined Goldman or McKinsey. There’s a super long feedback loop in venture (at least 5–7 years) to know if you’re doing it right, and if you suck at venture investing, it could be a huge waste of time. If you join a late-stage fund, you may not get significant dealmaking experience. What incentive does a CEO of a fast-growing Series A/Series B company have to speak to a junior analyst (most likely fresh out of college) when the partners at the firm make the deals? Finally, venture is an apprenticeship game, and there’s a lot of mediocre investors out there due to an influx of LP capital. If you get stuck under the wing of the wrong person, it may be detrimental to your career.
It looks like VC analysts are slowly becoming the new investment banking analysts or entry level consultants? If they are, is that a “good” thing?
I’m not sure I buy this, but it could just be from a personal vantage point. I see an insane amount of interest from most of my peers in IB or consulting because it seems safe and is deemed prestigious. It’s great to see new people interested in the technology sector, but overall, we’d probably prioritize people going into the operating, rather than investing, side. With that being said, there is a growing interest in venture capital as a career, but it may initially be for the wrong reasons.
As you know, VC funds do not have a structured recruiting process. There is some self-selection bias in who breaks into VC. What lessons can we use from that process for improving how conventional hiring works?
Honestly, I think VC hiring at the junior level is kind of broken. I haven’t seen what it looks like beyond associate and principal, so I can’t really speak to that. But I looked inside several VC recruiting efforts for undergraduates last fall, and there were a couple things I observed that felt flawed in the process. Most ‘brand name’ VC firms will only recruit analysts from target schools like Harvard, Wharton, Stanford, MIT. The impression I got was that you couldn’t even be considered for a position unless you went to a ‘top tier’ institution. That’s unfair and highly limits the candidate pool. The types of questions and areas that get looked at seem more tailored towards recruiting candidates for finance or consulting. I think financial analysis and rigorous cases are important, but if I were recruiting a junior VC, I’d be more interested in learning about their genuine interest in technology and see if they had “done the job already.” If I were hiring a junior VC, my first question would be: give me the references of five founders who you’ve helped in some way. Tommy Leep talks about this a lot. This helps in two ways. First, it weeds out probably 99% of your candidate pool. Second, these references are probably pretty telling of how good an investor this young person will become.
AngelList rose to popularity by applying Innovator’s Dilemma framework to venture capital. VC, as a product offering, is bundle of money, advice and connections. Thoughts on whether and how the bundle (and how we price that bundle) changes in the future?
AngelList is an absolutely fantastic product, and an effort, I believe, that will be beneficial to the long-term viability of the venture industry. This point has been noted before, but it’s interesting that venture, as an industry that champions scale, does not scale itself. AngelList helps democratize this a little bit and add some scale to VC. Additionally, firms like First Round Capital and Andreessen Horowitz have done a great job of offering venture capital as a product, or set of products. But, something that’s hard to unbundle is that some people, like Fred Wilson or Bill Gurley, are just incredible investors. They don’t need to offer any additional flashy ‘value-add’ pieces for entrepreneurs because they, as individuals, provide tremendous value when they invest in companies. This is going to be hard to ‘unbundle,’ because great investors will continue to emerge from an assortment of different paths and backgrounds.
Crypto is an all-consuming topic partly because of the hype and price speculation and partly because it brings together different disciplines like computer science, finance and economics together. What’s the opportunity cost of having so much focus on crypto and blockchain in general?
First of all, I think crypto, as a decentralizing force, is a good thing. The applications of blockchain in various instances, such as global trade and title insurance, theoretically make sense. However, they make less sense on a pragmatic basis. The opportunity cost in having an overemphasis on crypto and blockchain is that fundamental problems in legacy industries that relational databases, good design, and domain expertise could solve go unanswered. Investors flock to what’s hot instead of taking a step back and trying to independently assess what’s going to be a valuable investment opportunity. With that being said, I do think there are some critical blockchain and crypto projects that deserve a lot of attention right now. In terms of people, I would follow Derek Hsue and Anders Larson.
Let’s talk about some general tech trends now. People outside of tech think of tech as something that’s limited to software engineers or something that’s only associated with social networks or fun mobile apps. People within tech think of tech as an force that eventually permeates everything. The perceptions around pure tech versus tech enabled companies influences both who gets into tech and what gets funded. What are your thoughts on this disconnect?
The technology industry, at some level, believes every aspect of our society can be disrupted in some way. In one sense, that’s extremely ambitious and praiseworthy, but at times, problematic. A few years ago, one of my professors Jill Lepore wrote The Disruption Machine, which argues that every era has its model of history and the world i.e. what can help us describe the past and predict the future? Our current model of history is focused on disruption as an explanatory force. In the article, Lepore notes that Clayton Christensen’s theories are based on loose methodological foundations and aren’t fully explanatory. I think it’s a cool piece that looks at disruption from outside the tech community. The free markets and technological solutions can’t solve everything, and that’s important to acknowledge. One of the areas where that’s especially true is healthcare. Would recommend the discussion between Bill Gurley and Ezra Klein for more context on this debate.
Ring’s acquisition by Amazon has restarted the debated around hardware startups. Can you share your thesis about AWS of hardware?
It’s fairly simple — I believe it should be as easy to start a hardware company (prototyping, getting product in users hands) as it is to start a software company. I wrote about it in some more detail here, but I can give a high-level overview. There are tons of challenges hardware startups face that software companies simply don’t. There’s geographic barriers (manufacturing overseas is 10x cheaper), fragmentation (limited data + insights into quality and effectiveness of manufacturers and suppliers), knowledge gaps (an old-school supply chain consulting firms still exist), and capital inefficiencies (hard to access credit lines + banking). I think if someone solves some of these problems, they could unlock a $1B+ market opportunity not only by enabling current companies but allowing more and more companies to be built.
You recently tweeted “GroupMe sold too early”. Why do you think so and what trends are you seeing in social communication apps landscape? Given the growing popularity of apps like Amino, Islands and AfterSchool, and how common it is to have topic centric public chats on Telegram & Slack, are vertical group chats becoming the new social networks?
I personally believe GroupMe is one of the biggest missed opportunities in consumer from the past few years. If you look at college campuses across the country, GroupMe has to be an app with high retention and usage. Personally, I use it a ton every day. The fact that it hasn’t really evolved as a product but has so much stickiness says a lot about it’s core functionality. Messaging has taken off, but no one is really talking about GroupMe because they’re not making any moves. With the last part of your question, I think the answer is still TBD. I’d be interested in vertical group chats tailored towards enterprise use cases, such as Crew, primarily because I’m into enterprise collaboration. There may be opportunity in the consumer space, I just don’t see it as much. There was a period in about mid-2016 when a few different companies tried the public group chat concept like Public and Talkshow, but they didn’t really pan out.
Speaking of communications, enterprise collaborative software has become a hot race ever since Slack came along and became massively popular. What are your thoughts on how Slack is positioned and the strategy Facebook, Google & Microsoft have employed? Despite the intense zero sum game to get the big corporate clients, we still see newer products like Twist & Input popping up.
I do believe Slack is positioned well. They’ve grown incredibly fast and built some significant moats around their business, led by strong product and growth leadership. Additionally, their platform initiatives like Slack Fund and a robust API make the company exciting. Slack has grown incredibly fast in a way that most enterprise cloud companies don’t. They’ve almost had a consumer like growth trajectory. Next, I’d want to see what Slack’s penetration within the Fortune 500 or 1000 looks like. What does the strength of their sales and business development organization look like? I’d be keen to keep an eye on that. We’ll see what happens with Google and Microsoft — I think they’re in a better position in this space right now than Facebook because of their previous activities in the enterprise cloud. Are they able to get entire companies using the product or just siloed organizations? Dropbox is also a player to keep an eye on here.
Two themes I am increasingly interested in are real estate and healthcare tech. Do you have any strong views on investing or product trends in those areas?
Love this question. I think there are a lot of interesting developments that will shape up in the next few years in both of these enormous sectors. For commercial real estate in particular, I would recommend keeping an eye out on Compstak and VTS. Compstak has a pretty beautiful crowdsourcing model, and they’re slowly building a data moat that will allow them to compete with CoStar, the incumbent in the space. Compstak facilities the exchange of lease comps between brokers and collects all the data. The two questions I’ve been interested in with regards to real estate are a) How can commercial asset managers and landlords get better data on prospective tenants? b) How can real estate investment underwriting become a more collaborative process? On the second point, Dropmodel looks cool, but might put too much of a box around the process. With regards to consumer-focused real estate companies, I’ve seen a few pop up in the short-term housing space like Mod, Rezi, and Zeus. It’s a tricky nut to crack, primarily because the landlord market is fragmented across regions.
In terms of healthcare, I’m interested to see how these new D2C ‘health brands’ like Hims and Modern Fertility shape up. Apart from that, I’ve looked a little into the senior care space. Think it would be cool if someone built a Managed by Q like service for assisted living facilities. Additionally, I also think an interesting business could be a digital bank focused on serving healthcare providers.
I am going to pull a Thiel now. What one thing do you disagree the most on with these two groups — your friends at Harvard and your peers in tech?
With my friends at Harvard, I would disagree with the premise that quantitative skills are more important than qualitative skills. With my peers in tech, I don’t necessarily believe that for-profit tech startups can solve every hard social problem (aspects of healthcare, education, etc.)
Thoughts on our generation is talked about?
It’s unfair to call millennials lazy and entitled. You see tons of articles today that paint the snapshot of our generation with “Why Millennials are ruining X” with little factual basis behind them. If you look at our generation through a historical or structural lens, issues that we have to deal with like a competitive college admissions process, a turbulent job market, high levels of incarceration, and burgeoning debt stand out. This isn’t a plea for pity, but rather an attempt to demonstrate that there are real issues many millennials contend with that previous generations really did not have to.
Lastly, name some young hustlers in tech we should know and I should potentially interview for this series.
Jordan Gonen, Rohan Pavuluri, Athena Kan, Matt Schrage, Ben Crane
Other inteviews can be found here :