First impressions matter a lot to Robert Herjavec. This $100 million dollar man has made a fortune from his ability to size-up his competition in under 90 seconds and turn a profit on an elevator pitch. Not bad for a quick glance and a fast handshake.

So when I got the chance to meet the co-star of CBC’s Dragons’ Den and ABC’s Shark Tank — two reality TV shows where cash-strapped entrepreneurs pitch their business ideas to deal-seeking venture capitalists — I knew I had to look sharp and be prepared.

Being prepared for a 30 minute interview with a celebrity rich-guy is a bit of a daunting task, but my biggest challenge was deciding what to wear. After spending the last few years living on an organic cattle ranch and blogging from my Ikea sofa, I seriously lacked the business attire and wardrobe choices my former office-working self tended to wear.

Robert Herjavec’s answer to looking sharp is wearing a $7,500 Tom Ford suit. My idea of looking sharp would have to cost a little less.

And so I jumped into my second-hand blue Smart Car, filled the tank with $14 worth of diesel, and drove 7 hours to Vancouver in search of the perfect blazer, a shiny pair of shoes, and the courage to face a Dragon outside of his den. I must admit to being a huge fan of Dragons’ Den — there just is something engaging about watching a bunch of savvy (and not so savvy) entrepreneurs pitch their wares to a panel of mega-millionaires doling out dough. I couldn’t help but wonder if Dragon Herjavec was anything like his persona on the show; sometimes supportive, mostly brutally honest. I also wondered if his eyes were really that striking shade of blue.

In his bestselling new book, Driven: How to Succeed In Business And In Life (also available in Canada) Herjavec shares the story of his humble beginnings and his rise to rich-guy status. Born in Croatia, he and his parents immigrated to Canada in 1970 with just $20 in the family purse. As an ambitious teenager he worked for minimum wage as a waiter and sold designer suits to wealthy businessmen at Harry Rosen. Later he discovered computers, and in a matter of years built up his internet security company, BRAK Systems, and sold it in 2000 to AT&T Canada for $30.2 million (source).

His very inspiring ‘rags to riches’ story is told in this YouTube video, Dragons’ Den Road to Riches: Robert Herjavec.

Today Herjavec lives in a 50,000 square foot home located in Ontario, and winters in his Miami residence south of the border. His massive Mississauga estate occupies some serious space along the ritzy Bridal Path, where he has played host to Rolling Stones front man Mick Jagger and Canadian crooner Michael Bublé. If only the walls could talk.

Herjavec’s homes may be impressive, but so are his vehicles. He flies in a private jet and drives around town in his luxury car collection — two Lamborghinis, a Mercedes-Benz SLS AMG, a Rolls Royce Phantom (previously owned by rapper 50 Cent), a Bentley Continental GTC, and a limited edition Smart Car ForTwo — just to name a few. Having a Smart Car in common with the Dragon raised my spirits — I take a regular ribbing from friends and family over the strangeness of my ‘flea-sized’ auto. Go ahead and see a YouTube video of Robert Herjavec’s exotic car collection in action.

With my own (not limited edition) Smart Car parked safely in Vancouver and his Driven book chapters ‘Look Good,’ ‘Embrace Chaos,’ ‘Seize Opportunity,’ and ‘Believe in Yourself’ fresh in my mind, I figured that shopping on hectic Robson Street for something decent to wear would be the most fitting path to first-impression nirvana. I like nirvana, I just hate shopping.

To be honest, I’ve never been great at making a good first impression. I tend to be a little awkward at first glance, never know where to rest my eyes, and tend to say ‘Umm’ a little too much. I also excel at the fine art of fidgeting. Since he sold his company for millions and has reality TV experience to boot, I knew that Herjavec was going to be a smooth operator and a superior salesman. He was going to pitch his book and weave a good tale with ease and expertise. I just needed a decent blazer to wear.

And so there I was, standing on Robson street, desperately feeling the vibe of a chaotic street and needing to seize the opportunity to look good, when it happened. A familiar looking guy bounded past with a boyish charm and quick confidence. He was wearing baggy faded blue jeans, running shoes with floppy laces, and a light-blue untucked T-shirt. He was Dragon Robert Herjavec. And he was just a normal guy.

A few hours after spying my next day’s big interview, I managed to chill the frack out by finding a simple black BCBG blazer on sale. Since my first impression of Herjavec was just a happy dude in jeans, I felt totally OK with facing my Dragon in a $50 top and a dressy pair of dark denims. I decided to ‘look sharp’ in my used John Fluevog boots (found for a steal on eBay). I doubt Herjavec would know about Fluevogs, but I had test-driven these funky heels a week before while on a panel at a local blogging conference where they had caused a stir. The conference people were so busy looking at my feet that my fidgets went unnoticed. Perfect.

With my first-impression Dragon clothing decided on, I read over my interview questions. Unlike my clothing choices, my queries were ready a week in advance — because I am a nerd. I am calm. I will rock this interview like Mick Jagger in a 50,000 square foot Herjavec home.

24 hours later:

I am a mess. I can’t find a pair of scissors to remove the ON SALE price tag from my bargain BCBG blazer. I am starting to really hate black blazers, eBay Fluevog boots, and my digital voice recorder gadget. On my way to Vancouver’s Fairmont Pacific Rim Hotel — the meeting place for our interview — I drop my recorder-thingy gadget and fear the dang thing is now damaged goods. Herjavec would never be so clumsy. Frack, he’ll probably be wearing a Tom Ford suit.

I have somehow arrived at the Fairmont Giovane Café without my jacket price tag, wearing freshly-shined Fluevog boots, and with my questions in hand. Damnit, I will make a good first impression as outlined in Driven, even if it kills me. Besides, I think the voice recorder gadget thingy is still working. I walk in and look for a Dragon dude wearing blue jeans and hocking a pile of bestselling books. What I see is a finely dressed Robert Herjavec (with blazing blue eyes) rise up from his chair to shake my hand. He is wearing a blue tie that complements his powerful peepers. I have no clue if his suit is a Tom Ford, but I’ll try my best not to throw up on it.

I smile. I look for a place to sit. Maybe this is one of those new-fangled standing meetings I keep hearing about. But it’s not. Mr. Dragon is dancing around from table to table trying to find me a chair to fidget on. Weaving through tables, his experience as a waiter is evident. He finds me a chair and offers me a seat. I like him. He is totally casual despite wearing makeup from his morning television appearance.

I just need to sit down, start my hopefully-not-damaged recorder, and get going. No one can save me. I look around the cafe hoping to spy Mick Jagger in the audience. I could use a little infusion of (I Can’t Get No) Satisfaction a cappella style to jolt me into action. I look across the table and all I see are these brilliant blue Dragon eyes staring back at me. I am facing the Dragon.

Herjavec smiles in a media-friendly sort of way. Does he know I’m a blogger? A frugalist? Someone who lives in a way completely opposite to his flashy, expensive lifestyle? More importantly, does he like my funky Fluevogs and new tag-free BCBG blazer? I swallow an ‘Umm’ and start my recorder.

“Hi, I’m Kerry. It’s nice to meet you.”

Stay tuned for the next (and final) installment of my date with a Dragon — Dragons’ Den: 10 Money Questions for Robert Herjavec.