An entrepreneur’s job

Lessons learned at Y Combinator’s Startup School

Polsky Center @ UChicago
4 min readOct 27, 2016

Since its founding in 2005, Y Combinator has hosted an annual one-day conference filled with top speakers and practical advice from founders and investors — dubbed, “Startup School.”

As one would expect from a top accelerator, the speakers are consistently of the highest caliber. The past three years alone have included Marc Andreessen, Mark Zuckerberg, Jack Dorsey, Andrew Mason, Ben Silbermann, Kevin Systrom, and Reid Hoffman.

This year, the Polsky Center sent one of our own, Steph Avalos-Bock, assistant director of educational programming, to experience Startup School first hand. Below is an exclusive look at some of the most important entrepreneurial lessons she gathered from the day:

10. An entrepreneur’s job is to get it done.
Ooshma Garg, the founder of Gobble, told the story of the many fits and starts of Gobble’s early years. Through several major pivots, the company struggled to stay afloat. One breakthrough came when they met a particularly important investor. Ooshma’s advice for meeting that special person: “If you ever want to meet someone that’s really hard to meet, always tell them you’re nearby or next door.”

9. An entrepreneur’s job is to encourage risk-taking.
Pinterest founder Ben Silbermann emphasized the importance of making mistakes. He sees part of his job as a leader of the company as “making sure that everyone feels like they can take risks and break things.” What is learned along the way is a lot more important than having a smooth journey.

(This echoes remarks from Jeff Bezos at Business Insider’s IGNITION conference, when grilled about the debacle of the Amazon Fire Phone. That interview is worth watching too.)

8. An entrepreneur’s job is to set standards.
Silbermann also emphasized the founder’s job of casting a clear vision for the company, and how this is innately intertwined with hiring. He explained that a founder’s job is “[to drive] clarity for what you are building and why” and to ensure that everyone understands how their role fits in. An especially eloquent piece of advice from Silbermann was to always hire people who want to be known for what they build, not what they say.

7. An entrepreneur’s job is to reduce entropy.
Chad Rigetti, founder of Rigetti Quantum Computing, discussed the tension between product development and company development. The way to find balance is to realize that both are processes for “pumping entropy out of the vision”. Hire people who can reduce entropy.

6. An entrepreneur’s job is to be honest about numbers.
One of the funniest moments of office hours was when YC partner Kevin Hale whispered his question for the founders into the mic: “What. Is. Your. Growth. Rate?” He’d had to ask several times and was making a point that a founder’s job is to measure and study the company’s vital signs, not hide from them. At the very least, mentors, advisors, and investors need data to be able to help you.

5. An entrepreneur’s job is to be honest about people.
Both Marc Andreessen and Reid Hoffman gave advice on selecting investors and employees. Especially early on, when the company is smaller, having excellent people on your team is crucial. Hoffman recommends removing employees you wouldn’t fight to keep, rigorously checking references, and doing a big project together before committing.

(See recent Polsky medium post for more on this.)

4. An entrepreneur’s job is to think like the user.
This came up several times throughout the day. Silbermann discussed reducing hard decisions down to what is best for the user. More colorfully, Hale said “A lot of designers are like ‘I’m gonna make my mark on the world and design an interface that no one’s ever seen before!’, and users are like ‘How [in the world] am I supposed to use this? I’ve never seen anything like it!’”

3. An entrepreneur’s job is to get outside your preconceived notions of who your customer is.
We’ve all heard YC’s advice to do things that don’t scale. It’s important for growth, it’s important to land investors, and it’s important for understanding your market. YC partner Qasar Younis talked about the importance of being skeptical about your own assumptions of what your customer wants. The more customers you talk to, the more you learn about their needs.

2. An entrepreneur’s job is to explain why your company is exceptional.
If the vast majority of startups fail, the vast majority are a bad investment. Andreessen said that his firm looks at 2,000 startups a year and does about 20 deals. One important, early test for founders is procuring investment from a source designed to give out money. Customers and recruits can be harder to get the support of. Hoffman’s advice on the subject: get an introduction from someone the investor trusts and respects, show them something unique, and prove that you can win the game you’re playing.

1. An entrepreneur’s job is LIFE.
Startups demand too much risk, blood, sweat, and tears to do halfway. “Don’t do a warmup startup. Go do your life’s work!”

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Polsky Center @ UChicago

Fostering the innovative and entrepreneurial spirit at the University of Chicago | @polskycenter