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Picking winners and losers?

Harris isn’t the only political figure suggesting the American Dream is fading. In August, during a speech at a manufacturing facility in York, Pennsylvania, former President Donald Trump echoed a similar sentiment, saying, “Right now the American Dream is dead.”

However, O’Leary sees stark differences in the policies of Trump and Harris, arguing that their visions for the country take opposing approaches.

“If you go with Harris, so far from what we've learned, you as a people, as a taxpayer, as a Congress, as a country, are trying to ask the government to pick winners and losers in one or two of the 11 sectors that they think should get supported with these tax incentives,” O’Leary explained.

In contrast, he praised Trump’s approach, saying, “In the case of Trump, by lowering or maintaining the current tax rate, every sector is treated the same, and private capital like me and millions of others make our own decisions every day — millions of decisions that determine the outcome of an economy that's already proven over the last 200 years it knows what it’s doing because it’s still No. 1.”

One element of Harris's tax plan is the proposed increase in the corporate tax rate from the current 21% — a figure established under the 2017 Tax Cuts and Jobs Act spearheaded by the Trump administration — to 28%. This move is intended to generate additional revenue to fund her policy initiatives.

In contrast, Trump is advocating for a reduction in the corporate tax rate to 15% for companies that make their products in America.

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Diverging views on Harris

O’Leary also shared a clip of his interview on LinkedIn, underscoring his belief that the American Dream is very much alive. “I’m the guy that invests in small businesses that make up 60% of jobs. We are on fire!” he wrote.

While O’Leary has been vocal in his criticism of Harris, it’s worth noting that Harris has made supporting small businesses a key part of her economic platform.

She has set a bold target of 25 million new business applications by the end of her first term. Part of this initiative involves expanding the startup expense tax deduction for new businesses from $5,000 to $50,000.

Harris has highlighted the significant cost of starting a new business in America — averaging about $40,000 — as a considerable financial hurdle for many aspiring entrepreneurs. She argues that increasing the allowable tax deduction for startup expenses is effectively a tax cut.

“Not everyone has access to that kind of wealth and capital,” she stated at a campaign event in North Hampton, New Hampshire. “So part of my plan is we will expand the tax deduction for start-ups to $50,000. It’s essentially a tax cut for starting a small business.”

Who's the 'pro-business candidate'?

Moreover, not all voices in the business community share O’Leary’s skepticism toward Harris.

For instance, Mark Cuban, O’Leary’s Shark Tank co-star, has endorsed Harris, praising her as “pro-business.” He also noted that her team is “the most open” he has seen compared to past administrations.

Similarly, LinkedIn co-founder and billionaire Reid Hoffman expressed his support for Harris, noting that her approach is more favorable to businesses than Trump’s.

“Trump wants tariffs, which is anti-business,” Hoffman said in an interview with CNN. “It makes this a very strange election indeed, because I think actually Vice President Harris is much more of the pro-business candidate than Trump.”

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Jing Pan Investment Reporter

Jing is an investment reporter for MoneyWise. He is an avid advocate of investing for passive income. Despite the ups and downs he’s been through with the markets, Jing believes that you can generate a steadily increasing income stream by investing in high quality companies.

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