Get In The Start-Up Arena - Adam Chandler

Demo Days offer a way past the Catch-22 of entrepreneurialism.

Some things you just need to experience live. Entrepreneurialism is one of them.

I'm a big rock 'n roll fan – big bands, big arenas, and big occasions. When you're thereyou get it. On film, the Pearl Jam 25^th anniversary concert is just data. In the arena, it was a visceral, three-dimensional connection to the band, the music, the community, and the meaning of it all (personally, historically and communally).

It's that way with starting and growing digital companies, a big game for which there's no established playbook (the plays are just being written now). The only way to know what the game is like, what it values and rewards, and if it suits you, is to be on the field.

I know that's a kind of Catch-22. You can't acquire the experience without taking the risk, and people are less likely to take the risk on you unless you've got the experience. I know a lot of good marketing and sales people with startup dreams but mortgages and families keeping them in check.

That's why the presentation days that incubators put on are so valuable. Last week I went to my first Demo Day at the Brandery (www.brandery.org) in Cincinnati. I went because I'm now advising startups on sales and marketing – I've been a startup CRO twice, at Martini Media and Thrillist – but I experienced why anyone with a startup gleam should be there. In one day, I saw entrepreneurialism from all angles.

The day kicked off with Tim O'Shaughnessy, founder of LivingSocial, telling us how the company started, pivoted, and grew from 1 to more than 4,500 employees around the world. Tim was real and plainspoken about the problems he's had to find answers to. You could probably piece together the facts on his story from any number of articles, but you'd miss the energy of the telling.

Next came presentations from 12 startups that create digital solutions to common problems for consumers and businesses. Think of Shark Tank without the judges. For example:

· CrowdHall (www.crowdhall.com): An online venue for crowd-sourced town halls. Gives the audience a more amplified voice thanks to their social technology and allows more organization and perspective around crowd sourcing.

· Repp (www.myREPP.com): Ever wanted to buy a couch from someone on Craiglist but were spooked out by the randomness? REPP is an online identity platform that doesn't just identify you via your social networks but also through a third-party background check. Now you can actually know more about a potential date than all the flattery they post.

· Impulcity (www.impulcity.com): A location-based event discovery platform that makes it easy to find the things you want to do locally.

· Flightcar (www.flightcar.com): "A" for effort and guts. The 17-year-old founder explained how the company aims to create a marketplace – owners who have parked their cars at the airport renting them out to fellow travelers.

You can realize things from 12 presentations that you can't from one or two. Patterns emerge. I came away with a clearer sense of gap filling. These companies got to be on stage because they are filling gaps that investors can understand and (to varying degrees) customers will support. They talked authentically about their opportunities and threats at various stages, from the pure idea to the monetization model.

Until you surround yourself with the right people to drive the business from money, reference, and partnership perspectives, a business idea and plan don't mean anything. And until you've experienced the interchange, you can't sense if you want the startup environment, you see anything you can bring to it, or you're up to the high wire act if can be. The presenters engage with more than 400 people in positions to help charge their businesses forward. And everyone makes connections.

If you have an idea that fills a gap in the market but haven't gotten businesses off the ground before, or if you've got the itch to trade the corporate job for a startup adventure, check out the startup accelerators. Organizations like the Brandery shorten the time window on establishing the viability of the business.

As a first step, go to a presentation day. Demo Day can be Decision Day for the would-be entrepreneur. I mean that whether you're a prospective founder, employee or consultant. The energy will inspire you, set the appropriate level on expectations, and reveal what you need to be ready for – strategically, financially and emotionally. It's simply the quickest way to experience what's ahead.

Adam Chandler is a CRO in Residence at Lerer Ventures advising early-stage digital media companies on all things revenue. He is former President & CRO of sales at Thrillist, CRO of Martini Media, and Executive Director of sales for Yahoo.

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