In the first six episodes of Shark Tank Season 16, Kevin O'Leary has secured only one investment deal - joining forces with Rashaun Williams to invest $400,000 for 4% equity in Chalkless, a sports equipment company focused on grip enhancement. The deal included additional terms with a $2.50 per-unit royalty structure until reaching $4 million in payments, after which it would reduce to 25 cents per unit.
While maintaining his reputation for thorough financial analysis, O'Leary has evaluated numerous other businesses without reaching deals. Notable among these was KOBEE in episode 3, where he offered $300,000 for 20% equity, and FOAM Coolers in episode 6, where he proposed $150,000 for 33.3% equity. Despite showing interest in several companies and making multiple offers, these potential deals either fell through or were lost to other sharks.
Kevin O'Leary invests $400,000 in one deal on Shark Tank Season 16
Chalkless - Episode 5
The Chalkless presentation by Greg Pope and James Pidhurney caught O'Leary's attention with their solution for sports grip enhancement. The entrepreneurs sought $400,000 for a 4% equity valuation.
Their Shark Tank Season 16 Episode 5 pitch highlighted year-to-date sales of $740,000, demonstrating market validation. The company maintained strict control over production information but disclosed a 67% blended margin.
Shark Tank Season 16 Episode 6 investors O'Leary and Williams crafted a joint investment proposal. They offered $400,000 for 4% equity with additional terms. The deal included a $2.50 per-unit royalty structure until reaching $4 million in payments.
Following this milestone, the royalty would reduce to 25 cents per unit. The entrepreneurs evaluated multiple Shark offers before accepting this arrangement, recognizing the combined value of O'Leary's business acumen and Williams' market expertise.
Failed deals
Kevin O'Leary encountered several near-misses in his investment pursuits during Shark Tank Season 16.
Kevin O'Leary showed significant interest in KOBEE, a sustainable lip balm company that had made $860,000 in sales the year before appearing on Shark Tank. The company had impressive metrics, spending $14-15 on customer acquisition with an average order value of $36, and their 6-pack lip balms accounted for 75% of their sales.
When Kobe Harris asked for $300,000 for 6% equity, O'Leary felt the company's $5 million valuation was too high. However, he was impressed with Kobe's understanding of key business metrics noting this was better than most entrepreneurs he sees.
O'Leary made an offer of $300,000 for 20% equity, although Kobe offered a 15% equity. Kobe eventually declined to accept O'Leary's offer, choosing to walk away.
In episode 4, O'Leary expressed interest in NineteenTwenty, a convertible apparel brand that had achieved $505,000 in lifetime sales with a $97,000 profit. Kevin made a concrete offer of $250,000 for 30% equity, contingent on a full-time commitment from the founders. However, the 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 swimwear.
Despite the company's limited success, showing only $1,000 in lifetime sales, O'Leary saw potential and made a bold offer of $150,000 for 100% ownership. However, the deal fell apart when founders McKay and Karisa Winkel countered with a request for royalty payments and a proposed $500,000 patent sale. O'Leary rejected these counter-offers, and the founders left the tank.
In episode 6, O'Leary came close to making deals with multiple companies. He expressed strong interest in FOAM Coolers, presented by Chad Lee and David Kittle, who showcased their pressure-resistant, floating cooler design.
With $251,000 in yearly sales and 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.
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Kevin will be in the tank again for Shark Tank Season 16 Episode 7 which is set to air December 13, 2024.
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