Ask HN: Tips for making the entrepreneur-to-job jump

Maybe you can be a consultant who builds startup prototypes for people who hire you and pay you just as well, if not better. That way you could combine what you love to do (build startups) with being paid reliably and well.

Don't try to sell yourself as unconventional to conventional places. Make your resume seem normal by inventing titles and job descriptions that explain what you did in a more narrow way. Did you write all the code for your own startup from 2010-2013? Put down "Software Developer" as your title and describe the programming work you did. It doesn't matter that you also did a bunch of other stuff, because you were actually a programmer during that time.

"Have any of you made a similar jump?"

People get hired as PMs at large tech companies from all sorts of backgrounds. My pre-PM background is only slightly less varied than yours. Email me if you want to chat or want specific advice.

I'd recommend you pick up a couple of PM interview books: (i) Decode and Conquer, (ii) Cracking the PM interview. They aren't just useful for interview preparation, but helpful in thinking whether you want to do this sort of job, how to prepare your CV etc.

I made this exact same move about 5 years ago and it was a total fucking disaster. All the things you count as accomplishments as an entrepreneur just look like arrogant showboating during an interview. People hiring for fulltime jobs don't like to hear about how much creative freedom you had in the past, it means you'll be a rogue / pain in the ass.

Product management sounds like the perfect setting for a creative yet technical cross-discipline entrepreneur, right? Nope. Most PMs have zero authority in an organization. They're far below engineers in some cases. Remember how you had a staff of 15 people? The people working for you are collaborators, not reports. The job is entirely about internal politics, compromising between business teams. It has been described to me as "holding an umbrella to keep management BS from distracting the engineers so they can work". You're literally holding a shit umbrella. It's completely thankless and unrewarding, if not somewhat degrading.

In my case I used my sales skills to manipulate a freelance client into hiring me onto their product team without doing any due diligence. It was a disappointing, frustrating ordeal that lasted exactly 6 months before they pushed me back to consulting. Not worth it.

Be an engineer. You get paid much more, have surprisingly much more respect in an org, and less frustration at work.

But word of advice, do yourself a favor and shrug off that ego and accept your fate. If you were successful as a self-employed person you wouldn't be looking for a job, right? Allow yourself to say goodbye to who you were. If you keep that chip on your shoulder and sell yourself the way you're used to, you set unreasonable expectations for yourself and everyone around you. When you fail, the failure stings that much more.

Taking a job makes you a part of that world. You'll be waking up every morning slogging your way to the office with everyone else, trying to impress your boss, climb the corporate ladder. If you were expecting a "retirement" you're in for unpleasant surprises. It's not that simple or easy. Your brain is hardwired for a different lifestyle, a different workflow. You've never been leashed before. You're not of that world. The only way to win is to let the self-employed ego die and rise again, a new citizen of planet cubicle

PM job should be a great fit for you in good tech companies like Facebook, Microsoft, Google, Airbnb, Uber etc. Many of these companies also have growth team where they will love to have people like you who can drive growth of their business/ product.

Interviewing can be hard at times because you don't really know what interviewers are exactly looking for. You might know the answer but sometimes interviewers expect to see some specific pattern in your ranswer. You may also think about using the services of http://mockinterview.proudfolio.com for getting mock interview and personalized feedback for real interviewers of the companies for these roles.