Jason Calacanis' Best Career Advice

Individual audacity is the key to future success. Audacity = boldness of thought and action, which often contradicts established wisdom.

Jason Calacanis' Best Career Advice
Source: AngelList

The Blueprint Key Takeaways:

  1. Go to events with people and host your own events.
  2. Ask people who the smartest or hardest-working person they know is.
  3. Individual audacity is the key to future success. Audacity = boldness of thought and action, which often contradicts established wisdom.
  4. Break the rules. The rules are made by the people who the rules favor. The rules are made to keep you powerless.
  5. Be a generalist. Be able to quickly learn any skill that the business needs and become 50-70% proficient. Generalists thrive at startups.
  6. Get an inexpensive online education (Udemy or Coursera) rather than a college degree (unless it’s STEM and free). Skills > credentials.
  7. Make a blog, Twitter, YouTube, or TikTok. Start making professional niche content online. This multiplies your networking opportunities.
  8. Invest in and work at high-potential businesses. Get into high-potential trends early. If they succeed, you'll get huge rewards.
  9. When working a job, follow the blueprint episode 1 tips (summary below).
  10. Quit your job (1) when you’re not learning anymore, (2) if you have better opportunities, or (3) if your income isn’t going up enough.
  11. Never burn bridges.
  12. Speed matters in business. Move fast. Get things done.

The Blueprint Episode 1

How to have a successful career 

  1. Figure out what skill other people in the office don’t like doing that you can learn quickly. Then become known as the guy who does that thing. Ex) In basketball, everyone wants to be the one making 3 pointers or dunking. Instead, be the one who always gets rebounds. Rebounds are essential but nobody wants to do them. But good coaches (managers, executives) are always looking for great rebounders.
  2. Be known as the person who can teach new hires and give out your information freely. Write a manual for new hires on how to do the job.
  3. The fixer: the person who is always counted on to solve problems or start new tasks. The fixer researches a project quickly, get to 60-80% proficiency, then they find the people who work in the organization that can do the job or they recruit new people to do the job. Ex) Kawai Leonard was known for being a top defender in the league. But then he became a top shooter. Fearlessly add more skills as your company needs them. The fixer should be able to take, for instance, a one-way ticket to Australia and network and get connections with executives for the business.
  4. Break the rules. The rules are made by the people who the rules favor. The rules are made to keep you powerless.
  5. Networking: call a Mexican restaurant and order enough food for 8 people (because Mexican will cost far less than a fancy restaurant). Then call up a friend and ask them if they want to come. Then ask them if they know anyone in town who would want to come. Then talk to their friend and ask them if they know anyone in town who would want to come. Once the main food (burritos, quesadillas, etc) is eaten, keep ordering chips and guac to keep the costs down.
  6. Go to events with people and host your own events.
  7. A big key to networking is to spend sufficient time doing it.
  8. Another key to networking is have something to offer. Everyone wants to be connected to someone who gets stuff done and/or is powerful.
  9. Go outside of your close friends and family. They know all the same people you do—they’re not going to get you top-tier connections. Go outside of your comfort zone.

The Blueprint Episode 2

When to quit your job

  1. Quit your job when you’re not learning anymore or if you have better opportunities or your income isn’t going up enough.
  2. Make sure that you give your current employer enough notice when you quit. If you’re junior, you can say that you’d prefer 2 weeks but you can go up to 4 weeks if they need it. If you’re middle/manager, give 4-6 weeks notice. If you’re senior/exec, write out a list of all the tasks you do, help them interview/find a replacement, and give them a few months notice.
  3. Never burn bridges.
  4. As a business owner: when an employee leaves, ask them if they’d like to freelance for you sometimes. Gives you flexible workers. If another employee is sick or quits, you can have the freelancer do the work in the mean time.
  5. Do 18-24 month cycles. Work at a job for 2 years, learning and developing skills. Then quit and start a business for 2 years. If it works, keep doing it. If it fails, go back to work and do another 2 year cycle learning more.

The Blueprint Episode 3

How to supercharge your networking

  1. Be the host. Host parties and dinners for people. Get a friend and then say you and your friend are getting dinner and ask if they want to come. Key: at the beginning of the dinner, give a 30 second introduction for each guest and talk about how you know them—frames you as a super connected individual.
  2. Start making niche online content. Make a blog, Twitter, YouTube, etc. This multiplies your networking opportunities.
  3. Jason met Elon Musk, the Uber founder, and Sam Harris before they were famous just by networking with founders in his area.
  4. Play the long game (decades). The “nobodies” that you meet today could be the “Elon Musks” of the future.

The Blueprint Episode 4

A bias for action

  1. Speed matters in business. Move fast. Get things done.
  2. People inherently have a bias not to take action.
  3. Take risks and change radically to make your product better and utilize the newest tech.
  4. Most people think: “I’m a journalist, I can’t be an investor or an entrepreneur.” Winners say: “I learned so much as a journalist, of course I can succeed if I put in the work to be an investor or entrepreneur.”
  5. Goalies have a bias for action. They may not know which direction the ball is going, but they have to rely on instincts and start moving before they know where the ball is going. Otherwise they’d stand there and look dumb. So they have to take action even with incomplete information.
  6. Individual audacity is the key to future success. Audacity = boldness of thought and action, which often contradicts established wisdom.

The Blueprint Episode 5

Generalists vs Specialists

  1. Be a generalist. Be able to quickly learn any skill that business needs and become 50-70% proficient.
  2. You can work on 5 things concurrently and develop 50-70% proficiency.
  3. Sales is transference of enthusiasm.
  4. Generalists are extremely useful in founding companies and working at startups.
  5. Startups have to move quickly so they don’t run out of money and can beat their competitors.
  6. Learn how to manage specialists.
  7. You can later become a specialist if you find a skill that you love doing.

The Blueprint Episode 6

Get into trends early. If they succeed, you'll get huge rewards.

The Blueprint Episode 7

College vs free online education

Get an inexpensive online education (Udemy or Coursera) rather than a college degree (unless it’s STEM and it’s free). Skills > credentials.

The full episode is worth watching:

The Blueprint Episode 8

Finding and developing all-stars

  1. Junior employees cost less and they are easier to get. All-star employees are difficult to convince and they may have other obligations (they may not be able to leave their current position for 6 months, for instance.
  2. Think of hiring junior employees as an NBA draft. If you draft 5 players and 2 become all-stars, that’s really good. Typically, out of 5, 1 will leave and 2 you will have to fire and 1-2 will be good enough to keep. The 2 you keep have all-star potential.
  3. You want to find the people who are willing to work tirelessly. The people who just want an easy 9-5 are the people you’ll have to fire.

The Blueprint Episode 9

Manifesting your future

  1. Be early in a growing industry.
  2. “Skate to where the puck is going, not where it is.”
  3. Shoot for being #1.
  4. Set audacious goals.