Apple has offered to buy the augmented-reality startup Leap Motion multiple times, most recently in the spring of 2018.

Insiders said the figure discussed was between $30 million and $50 million, a fraction of the company's Series B valuation of $306 million. But negotiations fell through just days before the deal was to be closed, according to people familiar with the matter.

People familiar with Leap Motion said Apple's latest offer might have been the last opportunity for Leap Motion to sell a business that for years has teetered amid financial instability.

In late spring, employees of the augmented-reality startup Leap Motion were celebrating. The company was on the verge of being acquired by Apple, for what insiders said was a figure between $30 million and $50 million.

Apple had already started talks with Leap Motion's human-resources department to review company benefits and sent offer letters enclosed in white folders emblazoned with its silver signature logo — the arrival of which caused many employees to high-five around the office.

But then, just days before the deal was expected to close, Apple's offer mysteriously fell through, according to multiple employees at Leap Motion at the time, who requested anonymity to avoid retribution or other negative outcomes.

One insider described the deal's collapse as the result of "swirling negatives" surrounding the company, and many cast blame on its youthful cofounders, Michael Buckwald and David Holz.

At this point, however, Apple was familiar with the often eccentric behavior of Leap Motion's founding duo — after all, this was at least the second time in less than five years that Apple had weighed an acquisition of Leap Motion, multiple people familiar with the talks told Business Insider.

Not the first time

Leap Motion's first product. Kevin Smith/Business Insider The first time Apple expressed interest in buying the startup was about five years earlier, in 2013, when Leap Motion's cofounders met with the company to discuss a sale.

But the meeting went poorly, multiple people said, when Holz, the CTO and brilliant technical brain behind Leap Motion, said he had no interest in joining Apple's team.

Not only did Holz seem uninterested in Apple's prospective offer to acquire its team and intellectual property, the people said, but he was insulting. He told Apple representatives the company was no longer innovative, said its technology "sucked," and — to the disbelief of many there — praised the virtues of Android.

"That's why the Apple thing didn't work out. David was like, 'I'm never going to go work for those guys — they're the devil,'" a person who worked for Leap Motion at the time said.

That was only the first misstep in a yearslong courtship, with Apple expressing continued interest in acquiring Leap Motion despite what appeared to be Holz's marked distaste for both Apple's team and its technology.

Apple didn't respond to repeated requests for comment. But the episode reveals Apple's continued interest in technologies it could use for its rumored augmented-reality glasses and software, as well as what happens when a startup that was once highly valued lands on the sales block.

"Leap Motion is frequently solicited for acquisition by larger technology companies who realize the value of our team and the crucial role of our technology and research to the future of computing," a Leap Motion representative told Business Insider.

But many people familiar with Leap Motion described Apple's latest offer as a last-ditch opportunity for Leap Motion to sell a business that for years has teetered amid financial instability.

Got a tip about Apple or Leap Motion? Email the author at kleswing@businessinsider.com or direct message on Twitter @kifleswing. Secure messaging available upon request. You can also contact Business Insider securely via SecureDrop.

Flying high

Buckwald. Getty/Steve Jennings

In 2013, Leap Motion was flying high. That January, it announced a $30 million Series B funding round from top-tier firms including Founders Fund and Highland Capital Partners.

Leap Motion had captured the imagination of the tech industry on the strength of a demo video that garnered millions of views, showing people interacting with a computer — even playing "Fruit Ninja" — using only their hands and gestures.

The promise was that Leap Motion's algorithms could "replace the mouse and keyboard" with a piece of hardware that could sense the user's hands and fingers "with no visible lag time." The initial product paired with Windows and Mac computers, cost $80, and launched in July 2013.

At 25 years old, Leap Motion's cofounders were listed in Forbes' "30 Under 30" list alongside tech luminaries like Evan Spiegel, Tracy Chou, and Patrick Collison. They were revered by many as a brilliant but eccentric duo: Holz, a former NASA consultant, was the brains behind the project, while Buckwald, a serial entrepreneur and fierce debater, brought the company's business savvy as CEO.

The startup's A-list backing helped it gain wide retail distribution for what was mostly a tool for developers. Leap Motion's technology was embedded in an HP laptop, its product was sold in Best Buy locations, and its leadership could get meetings with anyone, including giants like Samsung and SoftBank.

That's when Apple kicked the tires on Leap Motion. The tech giant wasn't interested in Leap Motion's hardware, according to a person familiar with the talks, but was instead looking to acquire its team of "rock star" employees and intellectual property.

But the talks didn't go anywhere. Years later, some of those "rock stars" have joined Apple to work on augmented-reality projects, former employees said.

Read more: Leap Motion has lost its VP of design as the company moves offices to cut costs

Leap Motion had raised its Series B at a valuation of $306 million in late 2013, according to PitchBook, but its founders told their team that the fledgling startup was worth more — announcing that Leap Motion was potentially even worth $1 billion, according to people familiar with the matter, which would make it a unicorn.

Many people close to the company said the issues afflicting Leap Motion were a case of poor management. Much of the company's venture capital was spent on sleek office space in San Francisco's pricey SoMa neighborhood, complete with tech industry perks like beanbag chairs and daily lunches, as well as costly engineering salaries.

That Leap Motion should fall upon dire financial straits when the company's core technology had such great potential was described by many as a failure that could have easily been avoided.

Bad negotiations

While it's unclear why Apple eventually declined to purchase Leap Motion earlier this year, one theme is clear from Business Insider's discussions with people with intimate knowledge of Leap Motion: The founders ultimately thought it was more valuable than the offers on the table.

One issue for the startup was revenue. Despite Leap Motion's widespread availability and coverage in the technology press, sales were underwhelming and never enough to sustain a company, multiple former employees told Business Insider.

One strategy the company employed was to focus heavily on the technology's uses in virtual-reality applications, a hot sector of the technology industry in 2014. (Facebook bought Oculus that year for $2 billion.)

Leap Motion's North Star headset. Leap Motion

Eventually, Leap Motion narrowed in on augmented reality, a trendy technology that displays advanced computer graphics and information from the internet interspersed in the real word.

And in 2017, it raised what The Wall Street Journal reported was a $50 million round of funding led by clients advised by JPMorgan Asset Management.

But Leap Motion never received the entire $50 million, a person familiar with the matter said. Instead, the deal was a $25 million infusion of cash, with an additional $25 million based on performance goals, the person said. Representatives for JPMorgan Asset Management and Leap Motion declined to comment.

Then, earlier this year, Leap Motion launched an augmented-reality headset design, called North Star, which uses Leap Motion's hand-tracking technology and displays advanced computer graphics inside the headset's lenses.

It was a smart fit — Leap Motion's hand-tracking technology makes sense as one of the ways that people can control AR and VR goggles. On the surface, the North Star developer's kit competes with Magic Leap One and Microsoft HoloLens. But the headset has never been manufactured in volume, and it needs to be connected by a cable to a desktop PC.

Earlier this year, it became clear that Leap Motion would not hit the goals needed to unlock the second part of that funding, multiple people familiar with the matter said. Scores of employees have left the startup, which is now looking to cut costs.

Recently, Leap Motion moved out of its San Francisco office in a bid to cut costs, Business Insider reported last week.

"Leap Motion has moved its main technology hub from SoMa to the Financial District. Most of our team, however, is remote," a Leap Motion representative told Business Insider in an email last week.

It's unclear whether Apple is still interested in the company, but Leap Motion has taken meetings with other so-called strategic companies to explore the possibility of a deal, according to people familiar with the startup. It's unclear whether talks with potential acquirers are ongoing. Leap Motion is also exploring uses for its technology with defense contractors.

The core underlying technology could be valuable. Leap Motion has more than 100 patents and applications in its name, according to Sqoop, and its hardware is still used in many prototypes from startups seeking to build goggles or other hardware that needs gesture support.

It increasingly looks as if Leap Motion's technology might end up being bought as a hidden gem for a company looking to add its hand-tracking technology to future smart-glasses products — but only if it can get the founders on board with the deal.

Got a tip about Apple or Leap Motion? Email the author at kleswing@businessinsider.com or direct message on Twitter @kifleswing. Secure messaging available upon request. You can also contact Business Insider securely via SecureDrop.

Editing by Steven Tweedie.