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How to snag the attention of a VIP to sell your big idea — without being a stalker

Key Points
  • At just 26 years old, Tipster co-founder Andrew Duplessie sold the style advice app to Tim Armstrong, former chief executive of AOL and founder of dtx.
  • Now the 27-year-old Duplessie is in charge of product growth at dtx and is continuing to win the attention of industry leaders with his latest initiatives.
  • The tech entrepreneur believes wholeheartedly that when it comes to attracting attention, old-fashioned tactics work best.
Tom Merton | OJO Images | Getty Images

It's not every day you meet a twentysomething tech entrepreneur who believes in the power of old-fashioned tactics to turn heads. But when it comes to networking, Tipster co-founder Andrew Duplessie says he will do nothing short of walking a VIP's dog or sleuthing to find out their favorite brand of coffee and bringing them a steaming cup for a chance to engage with them.

"Nothing beats meeting face-to-face and getting to know someone on a personal level," he said. "I really believe that's the best way to get to know someone. ... It's vital to be bold, but without crossing the thin line into creepy," said Duplessie, who also works with VC companies to fund start-ups.

"Overstepping would be not producing value in their life," he said. "If they don't like your idea, fine, but give them something else — a coffee, a gift, doing one of their chores or something else. I would never harass them to meet. If they don't want to connect after my weird offer for coffee, then I would give them time and follow up a few months later."

This strategy has led to connections with some major players, propelling Duplessie's success as an actor — he's appeared in "Broken," "Royal Pains" and "American Horror Story" — venture capitalist, writer and entrepreneur.

But his AskTipster app is what really put Duplessie on the map.

At just 26, Tipster co-founder Andrew Duplessie sold his style advice app to Tim Armstrong, former CEO of AOL and founder of dtx. Now Duplessie is in charge of product growth at dtx and is continuing to win the attention of industry leaders with his latest initiatives.

Created with his best friend, Daniel Taylor, AskTipster launched in 2015 as an app in which users could get advice from industry experts in fashion, hair and beauty through direct chat, anytime and anywhere.

After its involvement with Stanford University's accelerator StartX, AskTipster transformed into a social growth and customer acquisition engine.

In June 2019 Duplessie and Taylor sold the style advice app and social growth engine to Tim Armstrong, the former chief executive of AOL and founder of dtx, a company that brings products and experiences directly to consumers, thereby bypassing the retailer. But that was not before the duo had built up a network of 10,000 stylists, much of it through personal outreach.

"I grew Tipster's stylists database from 0 to 5,000 stylists in 45 days and by three months had 10,000 by cold emailing, but making it personalized by adding a compliment on a social photo, etc. It seems so little, but it will separate you from the 100 other people that reach out," he said.

It's vital to be bold, but without crossing the thin line into creepy.
Andrew Duplessie
Tipster co-founder, actor, writer and venture capitalist

Now the 27-year-old Duplessie is in charge of product growth at dtx, yet he hasn't slowed down when it comes to coming up with new initiatives and winning over the attention of industry leaders with whom he can sell his big ideas. His latest: shaking up the publishing industry by using tech to forever change how books are read and marketed. "Books need to be connected to the digital world," he said.

Driving this idea is Duplessie's passion for writing horror stories. Besides adding Flowcodes to his books that link to additional content, augmented reality characters, secret maps and social media, Duplessie tracks and gathers data on reader response through live reads of his work on YouTube, then develops a full story based on those results. To date he has written more than 30 horror shorts, collectively garnering over 100 million impressions and 70 million YouTube views.

"I test [my] short stories and get data on how many people read it, saved it and shared it with friends. It helps me gauge what I should focus on for long form," he said.

In early 2020 Duplessie will release a 450-page young adult sci-fantasy novel set on Pangaea called "Stardom," and some of his short stories are now in talks to become films. Currently he has more than 250 million followers across Instagram and Facebook, and over the past year alone his social media marketing efforts have generated over 1 billion impressions and 5 million installs.

VIDEO6:2806:28
Tim Armstrong discusses his new direct-to-consumer product service

Yet while it is the young entrepreneur's brash, tech-savvy ideas that has made him a trailblazer, it is Duplessie's old-time, sometimes out-of-the-box techniques that appear to have made the biggest impression. Here are 10 of his best strategies that convinced VIPs to listen to his big ideas.

10 surefire ways to capture the attention of a busy VIP

1. Always ask to meet in person. "Sometimes it would be a slow response or they would say no, so I would ask where they got their morning coffee and if I could use the time they'd spend getting that by getting it for them so we could have time to talk. I would ask if I could walk dogs. I went to every length, and most people appreciated my persistence" said Duplessie.

2. Analyze a weakness of their business and offer free advice to solve it. This could be in the form of low Instagram followers, weak marketing content and so on. Duplessie recalled a company he was trying to partner with that was in desperate need of Instagram followers. "Right before the call, I had a major influencer friend give the company a shout-out. During the call, they gained several thousand followers and were really excited about it," he said.

3. Guess their email. It's easy to figure out an email by looking up a standard email within the company and using the same convention, says Duplessie. For example, info@google.com. "I grew Tipsters' stylists database from 0 to 5,000 stylists in a matter of months," he said, simply by guessing their email addresses and sending out pitches. "Eventually, I got it down to a science and automated much of the cold outreach process."

4. Test a cold email — in four different versions. It's hard to attract attention without having any connection at all, but it's still worth trying, said Duplessie. He advises sending out four versions of the same email to 100-plus people, and tracking which version generates the highest response rate. "You'd be surprised what little things within an email affect the response rate," he said.

5. Take the time to personalize emails. I grew Tipster's stylists database by cold emailing, but making it personalized by adding compliment on a social photo, etc. It seems so little, but it will separate you from the 100 other people that reach out.

6. Track who opens your emails. Use an email-tracking software to see when people open your email, at what time, where they opened it and how many times," he said, adding that he uses Polymail.

7. Be charitable. If you're able, make a donation to their charity (it can be small) or a cause they are involved with.

8. Tap into their interests. Ultimately, find out something you can relate to them on. "If they like to hike, go for a hike. If they like to play competitive water polo — Guess what? Jump in that pool. You love water polo, too."

9. Send a meaningful gift. "I once sent a Stanford hat to a Stanford alum venture capitalist that I was trying to get a meeting with. I knew he loved the school, based on public information," said Duplessie.

10. Win over their network of friends or relatives. The entrepreneur stressed the importance of connecting with a friend or relative of the VIP if possible. "At networking events, sometimes it's difficult to get the attention of a power person. In the past, I have chatted up their partner or plus one. Not only will you very likely end up connecting with the power person but their plus one always has an interesting story as well. So if you spend time chatting with their partner (aka husband or wife) or someone in their inner circle, like a colleague, try and relate to them on a human level; don't make the conversation about the pitch. Build rapport by being yourself. If you can win over someone in their circle, it will be easier to win them over when the time comes."

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