Sohail Prasad

Founder, CEO at Equidate. Y Combinator alum. Founding Partner at S2 Capital. Investor at Zenefits, Coin, 45+ others. Formerly: Zynga, Hiptype, Chartboost, Google, Carnegie Mellon, MIT Media Lab.
Fortes fortuna adiuvat.
Carpe diem.

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Don’t lose sleep over Fidelity’s recent startup write-downs

This article was originally published in VentureBeat.

[Disclosure: Sohail Prasad is a prior investor in Zenefits, which is a recipient of a write-down. No non-public information is disclosed in this article, nor are we receiving compensation for writing this article.]

Over the last few days, nearly every financial and tech publication has reported that Fidelity and Blackrock have written down their holdings in various late-stage startups. For many who have been predicting doom in the startup valuation bubble, this seems like a tipping point.

These institutions made their investments after conducting extensive due diligence on the enterprise, business model, and forecasts of each company. If they believe the investment is worth significantly less now, shouldn’t that be a red flag that those startups are overvalued? Isn’t Fidelity — a multinational financial institution that has $2

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Inspiration is overrated. In fact, you don’t have the right to tell me that you’re inspired.

Tech entrepreneurs search Hacker News for inspiration, while others take to watching TED Talks religiously. Let’s try it. Want to be really inspired? Watch Steve Jobs’ Stanford commencement speech from 2005. Read Randy Pausch’s The Last Lecture. Go on, I’ll wait - they’re both actually pretty great, two of my personal favorites.

Done? Sufficiently inspired? Great. I’m sure your life is significantly better – I bet you can feel it already, the inspiration coursing through your veins. Maybe you can share the link on Facebook! Email your buddies! Make a quick tweet with a quote:

So inspired… Stay hungry, stay foolish.…


You’ll get a retweet and a favorite! Your friends will love the quote. It’s all bullshit. Posting the quote and telling your friends gives you a

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There’s so much to reflect on every birthday. What happened in the last year. What didn’t happen. What could’ve happened. As I turn a year older, it only makes me realize what I’ll end up with in life: the memories, and the impact I’ve had on people’s lives. That’s it.

Thinking about all my past birthdays, I realized that as a kid, I cried on my birthday almost every single year. Some would say I was a birthday brat. I used to place too much value on a single day: “This is my day. Everything I want should happen. It’s gonna be perfect.” In that thinking I forgot that it’s just another day. I forgot to treasure the people that make me smile every single day. But over the past years I’ve realized that every day can be my day. I don’t need candles and wishes to chase my dreams. And that’s what I’ve done: I wake up every morning, thankful for the opportunities I’ve been given, eager to go

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Every morning in Africa, a Gazelle wakes up. It knows it must run faster than the fastest lion or it will be killed. Every morning a Lion wakes up. It knows it must outrun the slowest Gazelle or it will starve to death. It doesn’t matter whether you are a Lion or a Gazelle… when the sun comes up, you’d better be running.

–Christopher McDougall, Born to Run: A Hidden Tribe, Superathletes, and the Greatest Race the World Has Never Seen

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Fantasy VC

People who can’t own their own sports teams play fantasy sports. People who can’t invest in the stock market do virtual trading. Why should I be left out? I decided that I’m going to publish my list of investing picks (that I’ve kept private up til now), so that in the future I can (and you can) look back and see how I do.

To make it more realistic, I’m giving myself ~$3M/year to invest – that’ll keep me honest and help make me decide how much I like each company, not just that I like them (which is important from an investor’s perspective). I’m including the date picked as that’s relevant to finding startups before everyone else.

Goals are to identify both super successful and undervalued companies, before they becomes “obviously successful.” I’ll be attending YC Alumni Demo Day and meeting with a bunch of people in the tech community, because I do that anyway. Disclosures and notes

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Being Honest

Just in case you haven’t heard, Groupon founder & CEO Andrew Mason was fired earlier today.

I had the privilege of meeting and talking to Andrew last July (though trust me, we’re not “buddies”), and the one thing I remember most was his resilience and indomitable spirit. Even then, he was honest: people didn’t (don’t?) have a high opinion of Groupon. Yet nonetheless he had such a passion for Groupon, his baby, that it was hard for it not to be infectious. I came in a skeptic wanting to make a joke about a Ponzi scheme, and left with the feeling that he had a bigger goal than just offering people like you 20% off your movie ticket. I remember talking with him about his plans to solve some of the many problems that face small businesses and merchants today, to become the “operating system” for local commerce. His eyes lit up as he talked about how Groupon would help merchants grow and

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Crossing The Street

I judge people. All the time. You probably do it too, based on what you can tell about a person. By how they talk, what they wear, and how they carry themselves. By what you know of their family, where they went to school, or where they work. Maybe subconsciously by their skin color and accent too, though you’ll never admit it out loud. I know I do.

Judging isn’t a bad thing – it’s just a way to evaluate someone based on the information you have at a given moment. Sure, it can be wrong, but it’s just a baseline. Recently, I found another way to evaluate people that tracks pretty closely with real life.

Ready for it? Watch someone cross the street. Really, that’s it. You see, I’m of the belief that you can tell so much more about someone when their guard is down, when you can observe them doing something that’s so routine they usually don’t think twice.

There are four main kinds of

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Reflections and Moving Forward

It’s hard to describe the feeling of achieving something you’ve always dreamed of. I’ll be honest, when it happened to me, I felt like I was on top of the world, like nothing could bring me down. Until I had the sobering realization that maybe I had the wrong goal all along.

I’ve never really written about getting into Y Combinator or my (amazing) experience throughout. It’s mostly because in my head I’d decided that when I would write about it, I would write fondly of the days when we realized that we were on the path to success. Getting into Y Combinator was always a huge goal for me, as it undoubtedly is for many other aspiring entrepreneurs. It was the “one thing” I needed to ensure success. After all, once I joined YC, what could go wrong? Surely investors would come flocking and customers would line up in awe.

We created Hiptype as a side project in March 2012, while I was still

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What We Learned (repost)

Earlier this month we took our analytics service offline as we transition Hiptype to a new home where we’ll be able to have a much larger overall impact and achieve our mission of bringing data-driven tools to book publishing.

We have learned throughout the last few months that there are major challenges facing innovations in eBook publishing.

 Discovering an Opportunity for eBook Analytics

Back in the spring of 2012, we were just a couple startup geeks at the initial stages of writing an eBook about analytics and data. As we researched the various options for publishing our book, it quickly became apparent that eBook publishing was years behind the web and native apps in terms of the types of insights and analytics available to publishers.

While publishers of apps and websites can now capture sophisticated data about their customers and how they use their products, eBook

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Hiptype Launch Coverage

TechCrunch - Y Combinator-Backed Hiptype Launches A Google Analytics-Style Service For E-Books

Behind the product, Levy and Prasad have an ambitious vision.They argue that e-book publishers need to follow the example of popular websites by using data to become leaner and smarter. For example, they say publishers could start testing their books by releasing them to a small number of readers, then tweak the content based on the data. Hiptype also allows publishers to use its data to create targeted Facebook ad campaigns.

“We believe that data will save the book publishing industry,” Levy says.

paidContent - Hiptype wants to be the Google Analytics for ebooks

Publishers testing Hiptype in beta, for instance, were surprised by “how low conversion rates are” — early data suggests that only three to four percent of people who download a free ebook sample go on to buy the book — and how few

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