The Holloway Syllabus on Joining a Startup

90+ resources you need to learn the ins and outs of joining a startup.
Haley S. Anderson
▪︎ 14 minutes read time

This post is part of The Holloway Syllabus series. We’ll publish new Holloway Syllabi twice a month, and you can read and search the contents of all of them in one place in The Holloway Modern Work Library. To create this Holloway Syllabus, 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!) to help you master the ins and outs of joining a startup.


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 come in a lot of shapes and sizes, and stability and success are not at all guaranteed. The choice of which startup to take a job at can be the difference between a fulfilling period of growth, respect, teamwork, and even financial gain versus a period of crushing stress, interpersonal conflict, and failure. 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 successful startup employees, founders, and scholars have done a lot of the foundational thinking for you when it comes to joining a startup. They’ve written and spoken about whether you should join a startup at all, and which one to join if you choose to do so. They’ve offered advice on getting hired and what to do after that. They’ve shared stories of their own successes and failures. And we’ve organized it here. While you can’t eliminate risk in your decision entirely, we believe 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 even your whole career.

If you take that time and decide joining a startup isn’t for you, that’s one more data point you can now work with. And a lot 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.

Do You Want to Join a Startup?

Startup downsides

Founding vs joining

The decision making process

Which Startup Should You Join?

If you’re interested in thinking more deeply about the right company for you, we encourage you to check out the “Candidate-Company Fit” section of The Holloway Guide to Technical Recruiting and Hiring.

Getting Hired at a Startup



Negotiating Compensation

Succeeding Once You’re There

Dealing with uncertainty


Curiosity and self-learning

Management skills

Managing yourself

Managing up

Taking care of yourself

If you are experiencing anxiety, depression, or other signs of burnout, we hope you will reach out to a mental health professional. We have collected some resources below.

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

If you found this post worthwhile, please share!