Learning From Mistakes: Roy Peleg, CEO of FirstImpression.io (Part 1)

FirstImpression is Roy’s fourth startup. The prior ones had all failed, and Roy candidly discusses how and why they failed. There is much to learn from failures and mistakes, possibly even more than from successes.

Sramana Mitra: Let’s start at the very beginning of your personal journey. Where are you from? Where were you born, raised, and in what kind of background?

Roy Peleg: I was born in a city north of Tel Aviv. When I was 12, my parents separated. When I was 16, I left high school and started my entrepreneur journey. At the age of 18, I joined the army. After getting out of the army, I started a career as an IT manager. I then transitioned to being a junior developer and later went on to lead a team of developers. I also became a SEO team leader.

Sramana Mitra: What timeframe are we talking about?

Roy Peleg: I finished my last job when I was 30.

Sramana Mitra: What year was that?

Roy Peleg: 2012.

Sramana Mitra: What happens in 2012 after you finished this job?

Roy Peleg: I started a startup, but before that there were three other startups that failed and shaped a lot of what went on in the current startup. Everything is always divided between entrepreneurship and making a living.

Sramana Mitra: When you were doing this in the Bootstrapping With a Paycheck mode, what were the ideas that you were working on and what processes did you follow to do those businesses?

Roy Peleg: The first startup was a computer website. It’s one of the first ones in Israel. I did that when I was in the army. Sometimes, we had some time for ourselves. I was using my cell phone as a modem to connect my laptop to the internet. Then I actually learned how to program and set up the site.

That was the first project. It’s live until today. At its peak, I had 16 team members. We ran very large forums. We ran an article section. I learned a bit about monetization of websites and leading people. When I was released from the army, the next step was another project called The Future of Things. That website was in English and dealt with anything in technology and science. I had, again, more than 10 people contributing content for it. I made money from that. It got some recognition. All the startups I mentioned right now I did while I was either in the army or while I was an IT manager.

Sramana Mitra: It sounds like the kinds of projects you’re describing are media sites. Basically, websites with content. You were getting people to contribute content and would then generate revenues by advertising?

Roy Peleg: Yes.

This segment is part 1 in the series : Learning From Mistakes: Roy Peleg, CEO of FirstImpression.io
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