How to Break Into the Startup Industry (it's not by joining a startup)
I've met over 200 people hosting Ohours over the past 3 years and one of the most common 'types' of people I meet are business savvy people in one industry (not the tech industry) who want to break into the tech industry and don't know where to start. Often, these folks are in business school or working at a financial job, but they really come from all over: some are sales folks at a IT firm, some are HR people at colleges, and some are teachers or lawyers.
These folks share something in common, though: their understanding of how important new technology is in this economy has lead them to an interest in working the new tech industry themselves. They don't just see the new tech industry as a new place to look for a job, they are drawn to it because of their business savvy itself. They see the light, and they can't avoid it.
Before I go on, know that I share a deep connection with these folks. In 2005, soon after I graduated from college and took my first "crap" job in New York City, I started focusing my intellectual energy on the tech inudstry. My first job had me looking at a Bloomberg machine and watching CNBC all day and I realized that there was a tremendous amount more about new technology that I understood than the analysts and reporters that were covering this phase of the web. Knowing that I saw and understood something better than others inspired me to make my move into the tech inudstry and take advantage of this diparity/opportunity.
Now, when I left for the tech inudstry I did two thing with my career: one was right, and I would recommend others doing, and was was wrong, and I would discourage others from doing.
I would discourage people from just starting their own startup without spending any time in the tech industry at all. My first venture, VentBox, led me to many great things, but was a failure both as a startup and as a learning exercise, and when you fail without knowing what to learn from it, it's a total failure.
Anything that I learned from VentBox's next phase, BricaBox, was because I had already spent time in the industy due to my second decision. My second career move was a foundation for my success, and what I recommend for other non-coding folks who want to get into the industry.
What I did right
While I was getting interested in the tech world, I noticed that a business man I knew was running a great business but one that took little advantage of the cutting edge. His business was not in the startup world... his company sold TV and radio ads for a network of public TV and radio stations across the country. This company did also sell online ads, but only a few banner sizes and would often toss these sponsorships in to sweeten a TV or radio deal.
I thought he could do a lot more -- and so I pitched myself, time and time again, over the course of a year, and finally he bit.
For over a year and a half, while I was trying to get BricaBox going, I'd spend half my week at then National Public Broadcasting as a "Technology Strategist." What that meant is I took time getting to know their business, and then went out and vetted new technologies and figured out what new tech was worth implementing and how it could create a return for them.
From that position, I got to know tons of people. I remember getting to know Greg Galant when he was doing RadioTail, the folks at Brightcove when they were quite small, I got great contacts at YouTube, and saw dozens of other startups, especially in the audio and video advertising space, most in their earliest innings -- and I got to pick the winners.
You see, from that position -- in an existing company with dollars to spend and real potential to make money with new technology -- I could meet with anyone I wanted to. For startups, the potenial of a new customer is great, so they'll always take your call. For the company you're working for, having a big, existing business, is both comforting and scary, and so your work is seen as protecting the future of their business.
Needless to say, I met a ton of amazing startups, learned how to gauge their potential success as a startup and as a solution for the company I worked for. In hindsight, it was the perfect job for breaking into tech.
So my advice
As your first move, consider not starting up your own thing to taking a job in a startup itself -- there are a billion other people vying for the vew non-sales or programming jobs and once you're there you'll have limited exposure to how startups really work.
Instead, go find a big existing company that's doing just fine ignoring all the new technology that's out there. Make a case that they may be doing fine today but won't do fine 5 years from now and show them models as to why that's the case. Position yourself inside some company such that you get to meet with a ton of startup and think critically about what works in their company and with their product and what doesn't work.
Trust me, from a position like this you'll have way more exposure to the startup world than actually working in it. Afterward, you'll have a more critical eye than most of your peers and be able to pivot your career into startups and do whatever you want.