How can a failed 40 year old tech entrepreneur find a job at a startup?

I started 2 companies in the past 10 years both grew to 10+ employees and $1M-$2M in revenue before crashing. Since my last company closed, I've been looking for work at current tech startups but can't seem to get my foot in the door. Seems like I'm competing with younger candidates with less experience but stops at name brand startups. Any suggestions?


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!

Answered 11 years ago

You're carrying around a lot of head trash with this self-applied "Failure" label. Even if you do get interviews, you're carrying that in with you, and it'll make you screw the conversation up and give them reasons not to hire you.

Position yourself as the linchpin of the puzzle that the startup NEEDS--the guy who knows what it takes to succeed because he's seen both the good AND the bad. You need to do this in the top third of page one of your resume. People scan. They don't read. They're not going to take their time and saunter through every character of your resume. You have to grab them. Give them a reason to scan (not read) the rest of your resume. Make them curious enough to want to talk to you.

That's the purpose of a resume: to get that conversation. NOT the job. People make this mistake all the time. You do not need to include your life story in your resume. Just enough to create curiosity, "I gotta meet this guy."

You're competing against younger guys because that's who is applying. Sort and separate. Spend your energy carefully. "I'm running into two kinds of startups: those who want young, inexperienced people because they can't afford an experienced professional, and those who understand that to get off the ground they need someone who has been around the block and knows where the potholes are. Which situation are you in?"

Now you know whether to put your energy into this opportunity or not.

Getting a job is a game of sales, marketing and negotiation. You have to approach it as an equal, or you're a lamb to the slaughter. I think you have a long way to go, honestly, before you're ready to be hired.

Answered 11 years ago

+1 to what Jordan said.

Oddly enough, people love to hear about other people's failures. And from what I understand, failed startups are a rite of passage for an entrepreneur. You're a salty dog, and that's a really, really good thing.

If you haven't already, consider blogging about the specific mistakes that you, your co-founders, and other members of your team made, and what lessons you learned from those mistakes.

Get really specific with dates, numbers, and other details, but change the names out of respect to your former co-workers.

Also blog about what you're looking for in your next startup.

And your heroes and great books, conferences, seminars, mentors, and films that saved you from making more mistakes.

Remember this: If K. Anders Ericsson is right and mastery takes 10,000 hours, then you might already be a master entrepreneur. Walk in that truth.

Shoot, I'd hire you for your humility alone. It takes guts to not sugarcoat your failures in a public form. Kudos.

Answered 11 years ago

I've been an entrepreneur for over 30 years. I've had a half dozen nice successes. Have enjoyed a nice lifestyle. Raised a beautiful family. Still married to the wife of my youth (27 years and going). Yet, I have failed in business more than I can count. Failing does not make you a failure.

In fact, my friend said it best, "I don't really trust someone that hasn't failed".

It is in the failures that we grow and learn. Character is formed and success is realized in life's pressure cooker of trials and tragedies.

You are not a failure. You are a a hero for attempting to do the thing most people fear. You joined the ranks of the entrepreneurs. You are my hero!

The real failures are the ones that will never put themselves in a position to fail. In the very least, they are cowards.

Stand up. Be proud. Learn from the failures. Be a winner.

Now to answer your question. :)

Interview with confidence! You bring 40 years of experience, both good and bad, to the table. If the start up chiefs miss that point, move on and find a group of entrepreneurs that think more clearly. Are you in Oregon? I may know of a place for you. Don't spend the money to call me based on that, however. But, if I can be of further assistance, give me a call.

All the best hero!

Kevin McCarthy

Answered 11 years ago

Pick something you enjoy doing + just start doing it + also talk about how your doing, what you're doing.

In many cases you'll have greater income teaching what you do, than doing what you do.

Look at + any local conferences + CoWork offices + business networking mixers.

Anywhere they require a speaker, talk about what you're doing + how to do what you're doing.

Likely just talking about your experiences may create a lucrative consulting business for you.

Answered 7 years ago

while competition might seem intense, your unique journey brings a wealth of experience that can set you apart. Focusing on self-confidence and revisiting your foundations will allow you to project a compelling narrative. If you're looking to delve deeper into refining your approach, gaining insights, and receiving personalized guidance, seeking coaching or mentorship could be a transformative step. You've already demonstrated your resilience; with the right strategies and mindset, your next success story could unfold within the startup ecosystem. Reflect on past achievements, Embrace the Learning Curve, Reconnect with Your Passion, Consider a coaching or mentor relationship and Leverage your Network are the areas that I would start to focus on first. I'd be more than happy to develop a more comprehensive plan for you that is individualized once we speak further. Feel free to reach out!

Answered a year ago

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