The Holloway Syllabus on Joining a Startup

90+ resources you need to learn the ins and outs of joining a startup.
Haley S. Anderson
▪︎ 15 minutes read time


Regardless of what stage startup you join, the choice should be just that—something which you chose, a deliberate selection based on criteria that you’re optimizing around and the potential of upside, not a perception about safety. You should be joining a startup because of your excitement about the role/situation, the company itself, and the opportunities ahead with the chance to change the world. David Beisel, “Start with When”*

Startups vary in almost every way you can think of. Joining a startup can mean a fulfilling period of growth, respect, teamwork, and financial gain, or a period of crushing stress, interpersonal conflict, and failure—or a surprising combination. So how do you choose a startup to work for—and how do you know if the startup path is right for you?

The good news is that startup employees, founders, and scholars have shared lots of advice on whether to join a startup and how to get hired, and how to choose if a startup is right for you. They’ve shared stories of their own successes and failures. We’ve organized a lot of this advice here.

While you can’t eliminate risk in your decision entirely, it’s worth putting in a few hours of reading to make a better decision that’ll effect the next few years of your life and influence your career. Some of this knowledge will translate to decisions you have to make down the road. As Anand Chopra-McGowan points out, everyone can learn from startup employees—how they find their positions, how they adapt, how they manage their time, how they communicate with managers. This is a new way to think about your work, expand your skills, and decide what’s right for you.

To create this resource list, we put in more than 40 hours of research to pull together and vet great resources. We believe this is the most comprehensive and authoritative list (over 90 resources!) of resources about joining a startup.

Do You Want to Join a Startup?

Startup Background

Decision Making

Startup Downsides

Founding vs. Joining

Which Startup Should You Join?

Getting Hired at a Startup


  • Reverse Engineering a CareerCharlie O’Donnell — On learning about roles at startups in order to get a job in one
  • videoHow to get a job at a startupMattan Griffel — Describing the ambiguity and black box nature of startups and how to crack them
    • Summary: You don’t know what jobs startups are hiring for, or even what they need. That’s because many startups don’t even know what roles they’re hiring for. Startup skills are not like university skills. Your degree doesn’t align up perfectly with a job in a startup. How do you prepare yourself for a startup job:
      1. Train for skills, not roles — Jobs aren’t role-based, they are skill-based. Become top 25% in 2 or more skills to stand out
      2. Solve their problem — Big companies hire to meet additional workloads. They know the processes and that they don’t have enough people to fulfill that process, and so they hire more people. At a startup, they have a problem and are trying to hire someone to solve that problem. It’s your job to become more intimately connected to the problem, and the ways to solve that problem, than the person interviewing you.
      3. Flip the tables — Get startups and cos to fight over you. Position yourself as a leader in what you want to be best in. Start to teach. You don’t have to be an expert to teach people a few steps behind you.
  • How to Get Your First Startup JobJeff Bussgang
  • How I Hire: What MBAs Should Know About Startup JobsThomas Eisenmann — Written for MBAs, but applicable for anyone considering entering the world of startups


Negotiating Compensation

Succeeding Once You’re There

Management Skills

Further Resources


Podcast Episodes

Blogs and Newsletters

Job Boards

There are tons of job boards while you’ll find listings for work at startups! If you’re just getting started, you might consider checking some of these out.

Mental Health Resources

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