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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.

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