Why do people love Startup School?

I was lucky enough to be able to attend Startup School last week, with my Startup Digest co-curator David. For those who aren’t familiar with Startup School, it’s a free, all-day event organized every year (since 2005) by Y Combinator that brings together hundreds to thousands of hackers and founders for a day of candid talks by successful startup founders who have “made it”. The talks are not particularly tactical in nature, but rather seem intended to inspire while providing a human face to the sometimes sensationalized portraits of founders that we so often see in the media.

This was the first time attending for both of us, and I had heard rave reviews from friends who had attended in the past. As a curator of a weekly Silicon Valley events newsletter, I couldn’t help but wonder what the big deal was. In a place like Silicon Valley where high-profile tech events featuring notable speakers literally happen on a weekly basis, what makes Startup School so special?

Thinking differently

It’s ironic that Startup School took place during the same week as Dreamforce, because the two couldn’t be more different despite both falling under the category of “tech events”. For anyone who doesn’t know, Dreamforce is Salesforce’s (huge) annual conference. This year a whopping 135,000 people registered to attend, or 16% of San Francisco’s population, a number so big that the CEO of Salesforce bragged that it would “completely shut down” the city. In addition to its size, Dreamforce has become famous for the tons of free gifts (or “swag” as they call it) that are given away, its hackathon with $1 million in cash prizes, and appearances by celebrities like Hillary Clinton, Al Gore, Will.i.am, and Tony Robbins.

On the other hand, one thing that stood out about Startup School, even before I registered, was how unassuming and low-key it is for such a beloved event — There were no ads for the event plastered all over the city and on my FB and Twitter feeds like you see with other major tech conferences, and the Startup School website is so bare-bones that it would make a 90's web developer blush. And at the event itself, there were no big screen TVs, no crazy vendor booths, no high-priced coffee and snacks, and no fancy stage props or furniture. Just 1700 people, one college auditorium, a lineup of great speakers, and zero pomp and circumstance.

I don’t personally know anyone at Y Combinator so I can’t say for sure, but I got the sense that this no-frills approach is a deliberate homage to events like the Homebrew Computer Club, the OG (original gathering) of computer hobbyists getting together to talk about the cool stuff they’ve been building in their spare time, whose most famous member was Steve Wozniak, the technical cofounder of Apple.

The actual event itself

I met up with my co-curator David at 8:45am the morning of October 11th (a Saturday), and we began the 1-hour drive down to the venue. This year’s event took place in De Anza College, a community college in Cupertino located just two miles from Apple HQ and which has famously hosted the launch of the iPhone 6 and Apple Watch earlier this year, the launch of the iMac in 1999, and the launch of the original Macintosh in 1984.

We arrived around 10am and walked over to the registration tent, where about a dozen Microsoft Surface Pro 3's were laid out for people to self-register. (A surprisingly contrarian touch, given Silicon Valley’s unabashed penchant for Apple products.)

After an hour of coffee, snacks, and networking in the courtyard out front, everyone started filing into the auditorium and the program started promptly at 11am, kicked off by renowned angel investor Ron Conway. Ron Conway is famous for investing in founders, first and foremost, and his on-stage discussion with interviewer Paul Graham about the common traits of great founders set the tone for the rest of the day.

(Videos of all the talks are available via Youtube)

If I were to sum up the content of the entire event into a few overarching themes, it would be these three:

1. AUTHENTICITY : Great founders don’t “find” a good startup idea by looking for one. Rather, by being intellectual curious, aware of problems around them, and willing to experiment, over time they become the type of person who has good startup ideas “come” to them naturally without really trying.
2. FOCUS ON PRODUCT : Great founders are laser-focused on improving their product, and don’t let themselves get too carried away by non-core distractions like PR and other vanity sources.
3. RELENTLESS : Great founders are able to stick it through to the end even when all logic says they shouldn’t. Some people summarized this as “Don’t give up”, but I understood not giving up as being a function of how authentically passionate you are about the problem you’re trying to solve i.e. a natural effect as opposed to a conscious cause.

Every talk touched on one or more of these 3 themes in some way.

Authenticity

For Danae Ringelmann, the idea for Indiegogo was a culmination of her life experiences up until that time. Both of her parents had been brick-and-mortar small business owners who struggled for 30 years to raise any kind of outside funding, and as a junior Wall Street analyst, she had become heartbroken and disillusioned at an event called “Where Hollywood Meets Wall Street” where a sea of emerging artists swarmed around her almost begging her to help fund their projects, not knowing that she didn’t control any money at the investment banking firm where she worked. Danae made it her life mission to remove the need for “gatekeepers” and democratize access to capital for the makers of the world, and this vision is what drives Indiegogo’s company culture to this day.

Kevin Systrom of Instagram admitted that when he started Burbn (the precursor to Instagram), he wasn’t being very authentic. Practicing what he called “combinatorial entrepreneurship”, he basically took all the hot buzzwords at the time like HTML5, mobile, checkins, and social networking and combined them into a product that ultimately no one really wanted. But he did notice that the photos feature was the most popular among the few users he had, despite a less-than-perfect user experience and pictures that “never looked good”. Armed with this knowledge and drawing on his suddenly-now-relevant knowledge of filters from a photography class he had taken while studying abroad in Florence 5 years prior, he created the prototype for Instagram and the rest, as they say, is history.

Sometimes, authenticity can manifest in what you choose not to do. Reid Hoffman, when asked by Sam Altman why Facebook “had such a blind spot around games”, pointed out that Mark Zuckerberg has never been much of a gamer. Rather, he (Zuckerberg) is singularly focused on trying to make the world more open & transparent and having efficiency of information, connection, and communication flows. He didn’t consider gaming bad; it just wasn’t important to him, and he had the self-awareness to not pursue what was clearly a huge market opportunity.

Focus

It wouldn’t be a stretch to say that Jan Koum is the paragon of product focus. When WhatsApp was taking off, he started getting lots of emails from the press and from investors, and he would ignore all of them. Even when Sequoia Capital came calling, he didn’t answer. Sequoia eventually ended up getting a meeting with Jan, but to do so they literally had to walk up and down Castro Street in Mountain View to find Jan, because WhatsApp’s address was not publicly listed and their office didn’t even have a sign. When asked why, he replied that he simply didn’t have time for anything else. He and his cofounder Brian Acton would spend hours every day answering customer support emails (when they weren’t tweaking the product), and it was only when they were answering 100~150 customer emails per day that they decided they needed a dedicated customer service person.

Michelle Zatlyn of Cloudflare was also hounded by the press, but for a slightly different reason. As a non-technical female founder successfully leading an infrastructure technology startup in a male-dominated industry, reporters would call her every day begging for an interview, but she was steadfast in putting the company first and making sure the company was always focused on the unglamorous but critical things like hiring the right people, listening to customers, etc.

Andrew Mason was gracious enough to open up about some of his deepest regrets and mistakes at Groupon. In a nice counterpoint to Jan and WhatsApp, he spoke about how the overwhelming pressure to move fast and expand internationally (knowing full well how easy it was to copy Groupon) caused them to lose focus on the product and the culture around it. He noted how difficult it can be to stay truly customer-focused, and how easy it can be to make great-sounding excuses for why the company should make an exception to the rule “just this once”.

Relentless

Eric Migikovsky of Pebble and Hosain Rahman of Jawbone are both founders of hardware company founders who have had to deal with the kind of adversity that their worst enemies wouldn’t wish on them. Jawbone today is a multi-billion dollar consumer hardware company, but they had to live through several near-death experiences to get there since being founded way back in 1997, including actual death threats. Rahman described how he had to work without pay for 2 years, how a make-or-break holiday shipment of product was held up in customs because they had no money in the bank, and how at one point Jawbone’s investors shut the struggling company down, laid everyone off, and literally chained the doors of the office shut.

Eric first got the idea for a smartwatch while studying in Holland, where he wanted to be able to check incoming texts and notifications while biking around the city. Over the next 6+ years, he hand-built prototype after prototype after prototype, one of which eventually became Pebble. He now finds himself face to face with Apple and Google in the smartwatch arena, but he’s convinced that by focusing on making things that Pebble’s loyal community of users love, he’ll be able to build a product sufficiently differentiated to continue carving out its own niche in this growing market.

Last but not least, Emmett Shear of Twitch spoke about how unprepared and even incompetent he was early on making product decisions, raising money, hiring people, managing people, and even something as seemingly simple as talking to users. The only thing he had going for him was the determination not to give up, and after more than 6 years of struggling and learning on the job with a struggling product, it’s only recently that he felt really ready to successfully lead a company.

All in all, it was a well-balanced, eclectic lineup of talks.

Why do people go to events?

On the way back to the car, David and I shared with each other our thoughts on the event. I remember both of us expressed that we enjoyed it, but it was surprisingly hard for me to put into words why.

As event curators at Startup Digest, David and I often ask ourselves philosophical questions about events like:

• Why are people so drawn to certain events?
• What real, non-superficial value do they provide for their attendees
• What separates a truly great event from one that’s “just okay”?

The easy answer is that people go to events to 1) learn, 2) network, and 3) get free stuff.

But this answer wasn’t satisfying to me, because 1) Youtube and podcasting have made event content universally accessible and thus events are not the goldmine of knowledge that they used to be, 2) it’s not easy to form meaningful connections in a conference-type environment, and 3) any event can spend a lot of money to provide the best food and the coolest gifts, but that’s not what makes an event great.

While struggling to find an answer, I suddenly had a flashback of a memory from several years ago.

I was working for a 5-person mobile app startup in Seoul, Korea (long story), and we got an opportunity to visit Silicon Valley for about a week’s time. None of us had any connections here, and we scrambled to find anything and everything to do (outside of our scheduled business appointments) that was even tangentially related to startups and tech, in order to “experience Silicon Valley”, whatever that meant. And then out of the blue, one of the few people I knew in the area, who wasn’t even a friend but rather a friend of a friend whom I had only communicated with a few times via email, invited us to “Thursday Family Dinner” with his company (a Y Combinator startup) at their office, which was actually a house that they all lived in. I was astonished at their generosity — None of us had ever met each other, and yet they were inviting us into their office, which also happened to be their home. We had dinner together, spent an hour or two standing in the kitchen and asking about each other’s companies and stories, and then eventually called it a night. My Korean teammates and I had done a lot of stuff up until that point, but we all agreed that this serendipitous encounter was the undisputed highlight or our trip. We had finally experienced firsthand the “magic” of Silicon Valley that we’d only read about in storybooks and fairy tales.

Why people love Startup School

I tell this story because it reminded me of a fourth reason people go to startup events that I had almost forgotten, and that is 4) Energy.

The Internet has made it so easy for anyone to create and promote an event, but the best events will always be the ones that are able to bring together a focused group of serious, passionate, like-minded people who are there for no other reason than to share with each other and be part of something bigger.

Energy is why people still go to concerts even though you can listen to any song in the world for free online, and why people still go to live sporting events even though watching it at home in HD is a cheaper and technically superior viewing experience. There’s something validating and life-affirming about standing side-by-side with hundreds and thousands of other people like you, who believe what you believe, and knowing that you’re not alone.

For whatever reason, tech events can be notoriously low-energy. But for me, Startup School was a great reminder of how much of a differentiator Energy is for an event, all things being equal. There was a sense of excitement and possibility in the air that day that I just haven’t felt at many other events. I’m not saying that Startup School is the only tech/startup event where you’ll find that kind of energy, but it is one of the safer bets you’ll find in the Bay Area.

On the other hand, at highly publicized events with a lot of people, it can be hard to find “your crowd” in such a general and heterogeneous group, the same way it’s counterintuitively possible to live in a big city with millions of other people and yet still feel lonely. Startup School was the rare type of “big city” conference that’s still able to feel like a “small town” meetup.

As mentioned above, Y Combinator believes that the best startup founders are authentic, focused, and relentless. But Y Combinator is a startup as well, and Startup School is proof that they are following their own advice. I loved how simple and straightforward the event was, and I hope we can find and feature many more such events for Startup Digest going forward.

If you come across any such events, please let us know!