My First Startup

About nine years ago I gave up my day job to work on my own startup with a partner. The firm was a complete departure from my previous experience (which was the first mistake – ahem!).

The business was called Citizen Image and was focused on helping amateur photographers monetize their newsworthy images. We thought we had built a cool platform and that the concept was fairly cutting edge––especially for pre-App Store days.

One of our unique angles was seamlessly connecting our image collection engine to Nokia devices natively and to photo sharing sites like Picasa and kodakgallery. We raised some angel money and came close to selling the technology a few times.

Unfortunately, we only came close and ultimately walked away, far richer for the experience but with no cigar. I had to go back to the real world and get a real paycheck, and I wondered how to position myself with my newly acquired jack-of-all-trades experience.

How Startups Change You

Because startups have infinite potential and fortunes constantly shift, it’s hard to give up on the dream. Usually, a startup dies slowly. You eventually reach a tipping point where you can no longer avoid the inevitable and you have to return to the regular job market.

This isn’t easy. You’ve changed fundamentally after being a founder. You’ve experienced all of the aspects of a startup firsthand. At various stages, my partner and I were involved in product, business development, sales, marketing and finance. I was “CEO and Founder” and he was “President and Founder.” Because our startup was ultimately unsuccessful, I knew that we wouldn’t receive those titles in the “real world.” Still, I thought that the market would value my experience.

The Advice I Give As A Recruiter

Luckily, it didn’t take me long to realize that the market didn’t value my startup experience at all! Nine years later––seven of which I have spent in recruiting––I now advise others who have to make the same transition. Here’s how I tell them to handle the move.

Be Crystal Clear on Function

Recruiters are looking to fill a specific function. They want relevant industry or vertical alignment to their firm. There is already a CEO and a President so those titles won’t help you.

Your functional clarity is the most important element in a quick scan of your resume. If your function doesn’t align with what the recruiter is hiring for, you will be skipped over. Despite what you may think, being a jack-of-all-trades doesn’t cleverly hedge your bets by covering the bases––it actually makes you instantly forgettable because your function is not well-defined.

When defining your function:

  • Choose the part of your startup experience that aligns with what you are looking to do next. Instead of being “Founder and CEO” you can be “Head of Sales, Co-founder.” This ensures functional clarity and potential alignment to the job at hand.
  • Better still, choose the function that aligns with your experience pre-startup. This gives you functional consistency and makes you more attractive to a recruiter.
  • On your resume, ONLY emphasize the aspects and achievements that were relevant to that function at your startup.

Check Your Ego

You should drop CEO and other fancy titles from your resume. Yes, you’ve had a once-in-a-lifetime experience, but not everyone wants to hear about it. You’re about to meet an internal recruiter or a hiring manager. They might be jealous of your recent freedom from working for the man. Act humble!

Leverage Your Startup’s Industry Or Vertical to Pivot Your Career

You can pivot industries if you can make the connection between your old experiences and the ones you’d like to have. In my case, I leveraged a deep knowledge of user-generated content from my Citizen Image experience to get a job at Kickapps. I also used a solid rolodex of publisher contacts (partners of ours at Citizen Image) to get a job in a content tracking firm called Attributor.

Don’t Hedge Your Bets

If you want to appear credible in the eyes of a hiring manager, you have to move on from your startup. Being in quasi-denial won’t make you a convincing candidate. Make it clear that you have moved on.


All of this advice should prepare you to reintegrate yourself into the job market. I know it can be difficult to move on from a once in a lifetime experience like a startup, but sometimes it is what you have to do. Overall, be ready to move on, and leverage your existing skills in a way that clearly defines how you will contribute to your next company.

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