Lessons From Kevin O'Leary's First-Ever Small Business Retreat: Social Media, AI Help Diversify Better Than Legacy Networks

The momentum in small business creation continues to surge, fueled by shifting work patterns and a resilient post-COVID-19 pandemic economy.

According to U.S. data from 2019 to 2023, there has been a 34% increase in entrepreneurs filing “likely employer” business applications, alongside the total number of startups surpassing 15-year levels.

Kevin O'Leary said at his O’Leary Ventures Symposium in Miami that he believed the growth won't last forever, nodding to the potential implications of political and economic tumult. Addressing a room of 100 founders and operators at his first-ever, three-day small business retreat, the celebrity entrepreneur and investor said businesses may want to hedge their U.S. and China operations accordingly.

“I’m pro-small business in America, but you have to be aware of opportunities elsewhere,” he elaborated, noting, “India is like China but at a lower cost.”

The retreat, organized by O’Leary Managing Director Nancy Cheung, fostered connection, enabling O’Leary to understand how he can better support his businesses while providing insights on cost reduction, fundraising, branding and market penetration.

“This event was for my Shark Tank, North Dakota, and O’Leary Ventures family,” Cheung said. “This event was for the small businesses that survived the pandemic, companies that started in the basement, entrepreneurs who gave up their 9-to-5 and took risks. We tried going above and beyond for them.”

Graphic: Pictured is Nancy Cheung (far right) next to retreat-goers.

Replacing PR with TikTok

O’Leary is making waves with his remarks about TikTok. Should new legislation compel the app's foreign owners to divest, he aims to acquire the social media platform at a discount.

TikTok and similar platforms have played a crucial role in O’Leary’s branding strategy, allowing him to lower expenses and reduce reliance on traditional media and public relations agencies.

“It’s tough to be something without social media,” he shared as a lesson at the retreat. “Platforms like TikTok can help us de-risk and diversify so that we don’t have to rely on the legacy media networks; I am a network myself.”

Graphic: Pictured are retreat-goers.

AI Unlocking New Markets

O’Leary explained there is a noticeable correlation between market capitalization and social media, urging attendees to tap into technologies such as artificial intelligence for better, lower-cost content that is marketable to audiences worldwide.

“We’re piloting AI in our social media to market in different languages and places we historically have avoided,” added O’Leary Ventures & WonderEngine Senior Marketing Manager Kevin Teng. “We have tools now that can translate videos into multiple languages, saving significant costs.”

Graphic: Pictured is Kevin O'Leary listening to speakers presenting.

Where To Build and Why

Retreat-goers were encouraged to move to pro-business states such as North Dakota, where O’Leary actively mentors and invests in startups through programs like the Wonder Fund North Dakota.

Benzinga interviewed North Dakota Gov. Doug Burgum last year and learned the U.S. may foster stronger economic growth and decrease dependence on foreign entities through sustainable innovation in his state.

“North Dakota is a state that supports businesses,” the governor said. “Entrepreneurs now have a chance to have some wind at their backs.”

HealthTech and Crypto

O’Leary remains optimistic about opportunities in the health and crypto sectors, with a keen eye on the international markets.

He shared that M2 Exchange is a top choice among fully compliant alternatives, adding that the United Arab Emirates is becoming a capital of capital and deserves an allocation.

“The last crypto cowboys have ridden off into the sunset,” he said. “Not all of my deals work out. Most of them will likely fail, and it’s my job to find ways to stay in the game. The 2024 O’Leary Ventures Symposium allowed us to do that and share ideas very intimately.”

Graphic: Pictured is a group photo of retreat-goers

Photo: Courtesy photo