The Age-Old Battle Facing the Young Entrepreneur

by / ⠀Personal Branding Startup Advice / November 25, 2012

Fighting misconceptions about age is a challenge for all young entrepreneurs. It’s not easy to operate in a business world often populated by people much older than you, let alone to get them to take you seriously.

A 60-year-old doesn’t speak the same language as a 20-year-old. They don’t share the same hobbies. They have different energy levels.

I own and operate companies in two distinct industries: events and manufacturing. The events world is a young man’s game, with an average ownership age of 30. Manufacturing is an old boy’s club, with most owners in the 55-plus age bracket.

At my cleaning-products business, retaining the founder, Joe, as a partner-in-crime made my decision to buy the company a lot easier. Joe is in his early 40s, he’s been in the industry his whole life, and so has his father. My two silent investors operate in similar sectors, and let’s just say they have more grey hair than I do (at least for now).

I’m 28, and I think I’ve managed to successfully navigate the choppy age waters. I’d like to share some tips on how to pull it off.

Call first, meet later

When dealing with older contacts, have your first meeting by conference call and the second one in person. You’d be shocked by the number of people who tell me I sound 45 on the phone. The element of surprise shouldn’t be discounted. It’s not a bad thing to catch someone off-guard during the initial handshake moment. In fact, it gives you a bit of an edge.

Bring in senior partners or advisers

It helps to have someone with credibility talk you up. I often bring accounting-firm partners to meetings with new customers or targets. I’ve also asked more seasoned entrepreneurs to accompany me in supporting roles. They don’t need to do much talking. Their mere presence is enough to dampen any concerns about my maturity level.

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Don’t be afraid to share your achievements

Once it became known that I purchased shares in the cleaning-products company with earnings from my events business, the more people started to look at me differently. Canadians are known for their modesty and politeness. These are lovely traits, but they don’t do anything for your status. Money talks.

Dress and present yourself in a mature fashion

Actions speak louder than words. When you’re a young guy who talks a big game, people will watch you closely. Some of them expect you to fail. The best way to establish credibility is to look the part, and to be successful. When that combination comes together, everyone quickly forgets how old you are. Business casual is fine for the office environment on an average Friday, but that’s it. Going to work? Wear a suit. Leave the club talk at home, not the tie.

Illustrate your value added

Stand out in areas where older business people aren’t experts, such as social media. It’s a great equalizer. If someone has more traditional experience than you do, balance it out by steering the conversation toward your comfort zones of expertise.

And remember, if you really need it (and you can afford it), you can always hire age.

Billy Hennessey is the co-founder of Toronto-based events business Oxford Beach, and the owner of cleaning-products manufacturerRoyalPak, also based in the Toronto area. You can follow him on Tumblr at, and on Twitter @billyhennessey.


About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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