Stories of cold emails to Mark Cuban are oft-repeated startup legend--Alex Oshmyansky's being the latest, and arguably most ambitious, example of one that paid off handsomely. Big Data company FiscalNote got its seed funding back in 2013 when co-founder Tim Hwang cold-emailed Cuban. The Zebra founder Adam Lyons got his start in 2012 when he sent a similar email. Dhruv Ghulati of A.I. firm Factmata also started with a cold email, and so did Greg Maselli of food-freshness-pack-maker SAVRpak. The list goes on.

Cuban doesn't shower money and ­advice on startups just because he loves founders, though. He's a shrewd investor and proven entrepreneur who respects the hustle and values good, hard information--and an informed debate. Like any investor, he gets excited about big opportunities--financial ones, naturally, as well as those that could leave the world a better place.

Of course, chances are slim that any single entrepreneur not only gets Cuban's attention but also scores an investment--but the following strategies should help grab the attention of other big backers, too.

1. Get to the point

Don't waste words on flattery and warmup. With an NBA team to lead, a reality TV show to make, a portfolio of hundreds of companies, and an active role in a revolutionary pharma, Cuban is a little on the busy side. Say why you're getting in touch and what you'd like from him. And make it clear why it's worth his time. "Be direct and to the point," says Oshmyansky. And don't try to sugarcoat things. "He has an amazing BS detector, and there's no point trying to hide obvious truths."

2. Figure out his passions

Cuban talks publicly a lot, so if you do your homework, you can identify what subjects are trending for him. Early in the pandemic, for example, he was reading book after book about A.I. and teaching himself to design deep-learning models--because, as he told Inc., "I've been through the PC revolution, the networking revolution, mobile-computing, cloud-computing--and A.I. blows them all away. Whoever dominates A.I. will dominate the world over the next 25 years."

3. Show him you're serious

Although he appreciates brevity, Cuban is also a voracious reader and responds to detailed information. If you've engaged him, then keep him informed--but don't bore him. When Jenny Goldfarb, founder of Unreal Deli, a maker of plant-based lunchmeats, scored her investment from Cuban, his team asked that she send him weekly emails about her company's progress during the due-diligence part of the deal. That's standard practice for Cuban. Most founders stop or slow down those messages after the deal closes, but Goldfarb kept sending them every Friday--­four or five paragraphs, including updates on big sales wins, new product initiatives, big hires, and looming challenges. "I think it created a little buzz in his ear, so he really knew how we were ­doing," she says.

In response, Goldfarb gets weekly feedback from one of her entrepreneurial heroes. "Typically, it's a handful of words, maybe a full sentence, but it's very exacting. He's not messing around." Her company's new menu of vegan subs for ghost kitchens is a direct result of one of Cuban's responses.

4. Appeal to his sense of fairness

Institutionalized inequities, nonsensical legacy systems, middleman bloat. These are the things that get Cuban fired up to make change. "In general, the ideas that Mark tends to get most enthusiastic about are those that directly improve lives," says Oshmyansky. What's more, "he is willing to invest capital for the long term without looking to maximize absolute ROI in the raw financial sense. That is hard to find."

It's not that Cuban values slow returns more, but that he simply has the means now to pursue them. It's the potential for change that matters to him, not the speed of a ­return. Fatemi of Fireside adds that Cuban tends to attack inefficiencies by removing entrenched systems that drive up cost or limit access--PBMs, for instance.

5. And for heaven's sake, drop the jargon

Cuban doesn't surround himself with corporate machinery. There's no giant PR firm deflecting requests for his time--just him, responding in plain language, with unambiguous intent. When Fatemi, Google's youngest employee before she became an entrepreneur, relapses into tech-business jargon, Cuban is the first to call her out. "Stop being so Silicon Valley," he'll say.

She recalls an early presentation in which she called Fireside a "platform as a service." Cuban stopped her and told her nobody would know what that meant. He then zeroed in on what the platform ­offered--participatory entertainment--and suggested she reframe the presentation around that, emphasizing the use rather than the business context. It's that same instinct, Fatemi says, that makes Cuban "probably the best salesperson I know. He uses straightforward language that's transparent and everyone can understand." That's also what he responds to.