What Y Combinator can teach a freelancer

A radically different approach

Disclaimer: The views in this article in no way represent the views of Y Combinator (YC) or any YC partner. This reflects my personal journey and lessons learned. Thanks to YC for letting me write about my experiences.

My company, Rose Rocket, was recently accepted into Y Combinator’s Summer ‘16 batch. It was a life-changing experience, to say the least. It was also one that I downplayed to friends and family during the application and interview process, but one I dearly desired.

You see, Y Combinator has a sterling reputation of having funded and helped build some of the biggest startups today — Airbnb, Reddit, Justin.tv, Cruise and Dropbox — to name a few.

Y Combinator has a radically different approach on how to build a sustainable business and set yourself up for success.

Armed with my new YC wisdom, here’s what I’d tell former “freelancer Justin.”

1. Above all else, growth fixes many problems.

The No. 1 lesson I learned from my time at Y Combinator: growth can fix everything. The context of that statement is around hyper-growth startups with scalable business models. However, I think the essence of the advice may be applied to freelancers:

  • Set clear targets for your business and treat them as gospel.
  • Push yourself to grow your clients or revenue every two weeks to a month.

Many times, the death of freelancers is when they get lazy and dependent on one or two clients. When one leaves them — boom — they are looking for their next job.

Treat your growing freelance business like a startup.


Here’s how:

  1. Push growth every month. Set hard targets and go out and achieve them.
  2. Move revenue up and to the right every month. You can always choose to turn down work.
  3. Most importantly, prioritize certain activities over others to achieve your growth numbers. This can mean doing some things you wouldn’t necessarily do on your own, like networking (gross).

2. Apply the ‘three bullet point’ rule.

This is the second biggest lesson I learned while at Y Combinator. The first question we were asked in our interview was, “So, what do you do?” I’ve been told by founders that if you can’t answer this simple question concisely or so that any person can understand, you’re doomed.

YC forces founders of startups to really think about the shortest and clearest message that conveys the core of their business.

If you can’t explain your value or your services to customers clearly and in one sentence, you will be doomed.

How can your customers become advocates if they cannot remember what you do or how you’re different?

To get hyper-focused on your message, create a slide of your services. Describe what, how and why you do what you do in three bullet points. Use a maximum of 10 words per line.

Here’s an example of what that would look like for “freelancer Justin”:

  • What: I build iOS and Android apps for medium enterprises (9 words)
  • Why: I have 8 years experience (5 words)
  • How: I build functional beta software before final delivery (8 words)

These statement accurately:

  • Convey what I actually do (make apps).
  • Convey why I do it (8 years experience).
  • And touch on what makes me different (building functional betas).

A freelancer can do this exercise for everything from project briefs to statements of work and quotes.

Y Combinator Prototype Day
Paul Graham laying down the ground rules for Prototype Day in 2009. Photo: Kevin Hale via CC BY-SA 2.0

3. Do not optimize for the wrong things.

Be honest, are you spending 15 hours researching the new MacBook Pro? Making sure you get the perfect mix of power, price and features? I’m a gadget nut and love checking out new toys. But is 15 hours really helping you grow your business? Or should that time be spent acquiring the next customer?

Y Combinator constantly preaches about making sure you optimize for the right things.


Focus on tasks and items that increase growth. Just ask yourself this question: “Does this help me grow?”

If not, then stop wasting your time.

4. Don’t be a jerk.

Not much needs to be written on this topic, but I love that Y Combinator really stresses the “no asshole” policy.

Being a jerk (meaning, being selfish or conniving or disrespectful) has so many downstream effects. We all know this. But we have all come across jerks before.

So if you’re reading this and you know you’re a jerk, please stop.

5. Learn to highly leverage your time (remove distractions).

Y Combinator forces founders to move to Silicon Valley for their program. It’s a huge ask, but one that has many deep impacts. One of the biggest takeaways is understanding what highly leveraged time looks and feels like.

In YC, you only have 12 weeks to grow your enterprise about 10 percent to 20 percent week over week. A huge order, but when you move away from your family and friends (read: remove distractions) and focus all your energy on one task, big things can happen.

Here’s how this rule applies to freelancers.

Try this: Cut out out EVERYTHING that doesn’t help grow your business for one month. We so often do this with fad diets. “I’m not drinking beer in February” or “I’m not eating carbs in November” (can you tell I’m not a fan of these statements?).

But I do like this advice for your business.

For one month, cut out everything that doesn’t grow your business. No weekends away, no parties, no family adventures. Just work on growing your business.

Something starts to happen late at night when you would normally be watching Big Brother. Keeping your focus laser-sharp allows your brain to find all sorts of new avenues and ideas.

This is a pretty hardcore exercise, but Y Combinator changed my life. Try it out if you’re up for the challenge.

If now’s not the time, start with any of the other lessons I’ve shared. I hope you find value in them and see the actual impact they’ll have on your freelancing business.