Kevin O'Leary's investments so far in season 16

In the first six episodes of Shark tank In Season 16, Kevin O’Leary only secured one investment deal: partnering with Rashaun Williams to invest $400,000 for a 4% stake in Chalkless, a sports equipment company focused on improving adhesion. The deal included additional terms with a royalty structure of $2.50 per unit until reaching $4 million in payments, after which it would be reduced to 25 cents per unit.

While maintaining his reputation for in-depth financial analysis, O’Leary evaluated many other companies without reaching any deals. These included KOBEE in episode 3, where it offered $300,000 for 20% equity, and FOAM Coolers in episode 6, where it offered $150,000 for 33.3% equity . Despite several companies showing interest and submitting multiple offers, these potential deals fell through or were lost to other sharks.

Kevin O’Leary invests $400,000 in a single deal Shark tank Season 16

Chalkless – Episode 5

THE Presentation without chalk by Greg Pope and James Pidhurney caught O’Leary’s attention with their solution to improving sports grip. The entrepreneurs were looking for $400,000 for a 4% equity valuation.

Their Shark tank The Season 16 Episode 5 pitch highlighted cumulative sales of $740,000, demonstrating market validation. The company maintained tight control over production information, but disclosed a blended margin of 67%.

Shark tank Investors from Season 16, Episode 6, O’Leary and Williams, came up with a joint investment proposal. They offered $400,000 for 4% equity with additional conditions. The agreement called for a royalty structure of $2.50 per unit until reaching $4 million in payments.

After this step, the fee would be reduced to 25 cents per unit. The contractors evaluated several offers from Shark before agreeing to this arrangement, recognizing the combined value of O’Leary’s business acumen and Williams’ market expertise.

Failed transactions

Kevin O’Leary encountered several near misses in its investment activities during Shark tank Season 16.

Kevin O’Leary showed considerable interest in KOBEE, a sustainable lip balm company that had $860,000 in sales the year before he appeared on Shark tank. The company had impressive stats, spending $14-15 on customer acquisition with an average order value of $36, and its 6 lip balms accounted for 75% of its sales.

When Kobe Harris asked for $300,000 for 6% equity, O’Leary felt the company’s valuation of $5 million was too high. However, he was impressed with Kobe’s understanding of key business metrics, noting that it was better than most entrepreneurs he’s around.

O’Leary made an offer of $300,000 for 20% equity, although Kobe offered 15% equity. Kobe ultimately refused to accept O’Leary’s offer, choosing to walk away.

In episode 4, O’Leary expressed interest in NineteenTwenty, a convertible clothing brand that had made $505,000 in lifetime sales with a profit of $97,000. Kevin made a concrete offer of $250,000 for 30% equity, subject to a full-time commitment from the founders. However, founders Ashley and Zach Sankar ultimately accepted Robert Herjavec’s competing offer of $250,000 for 25%.

In episode 5, he expressed interest in Moonies Swimwear, a company with a unique design featuring a distinctive large hole in the back of their men’s swim trunks.

Despite the company’s limited success, showing only $1,000 in lifetime sales, O’Leary saw the potential and made a bold offer of $150,000 for 100% ownership. However, the deal fell through when founders McKay and Karisa Winkel countered by demanding royalty payments and proposing a $500,000 patent sale. O’Leary rejected these counteroffers and the founders left the tank.

In thepisode 6O’Leary came close to making deals with several companies. He expressed keen interest in FOAM coolers, presented by Chad Lee and David Kittle, who demonstrated their pressure-resistant floating cooler design.

With annual sales of $251,000 and a recent expansion into Target stores, the company caught O’Leary’s attention. He offered $150,000 for 33.3% equity, but the founders ultimately chose Daymond John’s slightly better offer of $150,000 for 30% equity.

Kevin will be in the tank again for Shark tank Season 16, Episode 7, which is scheduled to air on December 13, 2024.