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Job Search Strategies: How can a failed 40 year old tech entrepreneur find a job at a startup?
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Tom Williams, Clarity's top expert on all things startup answered:

Carolyn's points are spot-on. Tactically speaking, I would suggest that you make contact with the recruiting partners at the top VCs. Greylock, a16z and others have partners specifically focused on helping their portfolio companies with recruiting. Cold calls and emails with a "I'm an entrepreneur that has built two companies, one of which grew to X in Y time, and the other grew to X in Y time. I'm interested in exploring opportunities within your portfolio who are looking to scale-up their growth and sales" should get some discussions initiated with these recruiting partners.

Stage of company matters too. You're more likely to find a fit with a company who is post a $1m seed raise and already scaling-up.

I'd also think a lot about what role you're interviewing for. The problem with a generalized entrepreneurial background is that it can be perceived as "jack of all trades, master of none." So in order to improve your resume, you might be best to be 2nd to a great growth lead or be the first hire under a VP Sales.

Also, I'd suggest that you research the ages of the founders. If they are under 30, they are more likely to be biased to hire younger talent, but over 30, that bias often swings the other way.

I'd recommend you call Carolyn if you want help on how best to present yourself to prospective employers. I'm happy to talk to you about your background and experience and recommend more specifically the kinds of companies and roles that might be the best fit for you. Best of luck!

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