Insights from Cory Levy’s Fireside Chat

Luke Clancy
Illini Blockchain
Published in
6 min readSep 14, 2022
Shoutout to the Siebel Center for Design for the space & Domino’s for the food.

On Monday, I sat down with Cory Levy for a 1.5 hour long fireside chat. Cory is a serial entrepreneur & investor. He has founded companies with ~20M users, angel invested in 20+ startups, & been featured in Forbes 30 under 30.

Over 60 UIUC students & faculty got to hear Cory’s entrepreneurial journey, learn actionable tips for success in tech/startups, ask him live questions, & text his personal phone number!! Pretty cool right?

Here at Illini Blockchain, we believe in capturing our insights and sharing them with everyone. If you weren’t able to make it (or you want a quick recap), we’ve got you covered 🤝

Here’s a 5 minute recap of what we learned from Cory!

Real quick: learn more about Illini Blockchain here. And shoutout to Joe Morgan & Danny Koch for helping me write this.

Cory’s Story

School & Early Tech

  • Knew he wanted to work in tech at around 14–15 yrs old. Obviously, they wouldn’t hire him. So, he cold-emailed Venture Capital firms to work for them. He landed a gig at Founders Fund by convincing them that they would want his teenage perspective.
  • Heard about UIUC from someone at the firm, so he went to study there.
  • Intentionally studied CS because it was hard. He believes you should study things that are hard to learn because they become much harder to learn after you leave school.
  • Took a gap year during his Sophomore Year because he got a once-in-a-lifetime opportunity from some big investors. His gap year turned into dropping out. He still encourages students to stay in school (unless the opportunity is big enough).

Founder & Investor

  • Early success led to investing in startups/people and starting tons of other experiments.
  • He was the first investor/believer in many unicorns & 9 figure companies like Ramp, ZenBusiness, & Vise.
  • He’s formed a huge network of mega-successful people in tech.
  • He’s running 2 big experiments right now:
  1. ZFellows: he gives young people $10k to stop what they are doing & work on building a business for a week. He pairs the fellows with mentors who have founded $1B+ companies.
  2. First Text: use this app to ask Cory for advice & tell him what you are working on. Every month, he picks the 10 best people to meet his network of massively successful founders. Shoot him a text at 605–505–9984.

Cory’s Advice On How To Succeed in Tech & Startups

1. Start Generating Ideas

There’s 3 great ways to become an idea generation machine:

  1. Ask smart people who are older than you: What is the next big thing? What areas are they looking into the most?
  2. Observe your own actions and see what problems you have.
  3. Take a company/idea that already works, then change it a little bit. Modernize it. Change the target market. Change the marketing tactics. Don’t reinvent the wheel.

2. Leverage Your Unfair Advantages

Unfair advantages are the things you are uniquely suited for. Find them through reflection & consistently double down on them. The internet rewards expertise.

  • For college kids — leverage your naivety, youth perspective, & access as a student.
  • Naivety — every disruptive company was founded by people who didn’t have industry experience.
  • Perspective — what is obvious to you that your parents don’t understand? Share these insights with people who want it (ex: investors)
  • Access — people want to help students (especially alumni of that school). Cory responds to every UIUC student that texts him.
  • Sell your unfair advantages when recruiting people onto your team. Ability to recruit is a huge trait investors look for in founders.

3. Master Cold Outreach

He has gotten the vast majority of his opportunities from cold emails & Twitter DMs.

  • We attached an investor outreach template at the bottom (said by Cory himself).
  • Older people are very receptive to students. Use this access while you still can (only 4 yrs).
  • When reaching out to people, smart small. If you are starting a YouTube channel, you don’t reach out to Mr. Beast right away. You go for someone with like 10k subs.
  • When meeting with important people, ask for a 10 minute meeting.
  • These people are busy. Cory himself schedules his meetings for 10 mins. They can always go longer if the person is interested.

4. Constantly Build Forward Momentum

His two favorite words are forward momentum.

  • With anything you pursue, you should always build forward momentum.
  • There is no better founder trait than a bias for action. Nothing can replace it.
  • Get results & show progress. Everything else (like industry expertise) is secondary.

5. Focus On Growth

Growth is an incredibly overlooked & underthought aspect of startup success.

  • Far too many people don’t think about growth.
  • “If you took 3 months to build your project, then you should take 3 months to research and figure out how to market the product.” — Reid Hoffman
  • For non-technical folks, this could be your path to tech success.

6. Other Insights

  • Now is the best time ever to start a startup.
  • Act like a Freshman! Talk and meet as many people as you can, ask questions, & build a network.
  • Understand value: your value to others, other’s value to you, & things that other people value.
  • The financial upside of big tech is practically capped out.
  • As a young person, you should optimize for 10,000% returns on knowledge & capital (NOT 7%).
  • Aim for the biggest win possible. If you’re going to spend a lot of hours doing something, you might as well get a big payoff.

Final Conclusion

Huge shoutout to Cory for coming down!! We learned A LOT from this chat.

And we actually decided to change some things within the club. Our internal systems & projects will create a forcing function for our members to get better cold outreach, understanding leverage, & building a bias for action.

We are hosting a lot more fireside chats & discussions around UIUC. Subscribe to our public calendar & newsletter for event updates.

- Luke, Joe, & Danny

Cold Message Template

Subject Line: leverage your access as a student

  • UIUC Sophomore w/ Communication Startup

Body: No small talk BS. Tell them who you are & why you are messaging them. Be short (value their time).

  • 2 sentences about yourself: my name is ___. I’m studying ___ at UIUC and am working on ___.

The Pitch: know what your recipient values

  • Your Ask: “I need _____ money for _____ cool project, I am going to be building it w/ _____.
  • Your Value To Them: “You will get exposure to _____ people, at _____ University, it may or may not work, but you’ll get more than _____ amount of value because ___”

If you want to reach out, DM me on Twitter. For more info on me, check out my personal website.

Curated gold nuggets of timeless wisdom I find:

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Luke Clancy
Illini Blockchain

I am obsessed with how great civilizations, organizations, and humans were built. More: lukeclancy.me