What are the biggest individual investments Kevin O’Leary has made since joining Shark Tank?

1. Plated — the biggest financial exit attributed to O’Leary

The single largest exit tied to Kevin O’Leary’s Shark Tank investments is Plated, which was acquired by the grocery chain Albertsons in a deal reported at a $300 million sale price; O’Leary himself has singled out Plated as “one of my deals” that became the biggest exit in Shark Tank history ^[1]. Public accounts emphasize the sale amount and O’Leary’s characterization of it as his top Shark Tank payoff, but the exact dollar return to O’Leary—how much he invested on‑air or privately and his eventual multiple—is not disclosed in the sources available here ^{[1] [4]}.

2. Groovebook and Wicked Good Cupcakes — small stakes, outsized returns

Groovebook is consistently cited by O’Leary as one of his best Shark Tank winners: less than a year after investing $75,000 he and co‑investors saw the company sold to Shutterfly for $14.5 million, a result O’Leary has described as a major win ^{[2] [1]}. Wicked Good Cupcakes is another frequently mentioned success in O’Leary’s roster and is cited in CNBC’s reporting as one of his better performing Shark Tank investments, reinforcing a pattern where relatively modest on‑air checks produced meaningful exits ^[2].

3. Zipz — the largest on‑air cheque recorded in public deal logs

Independent Shark Tank trackers report that the largest single on‑air investment O’Leary made was a $2.5 million commitment to Zipz for 10% of the business, marking it as his largest televised cash outlay ^[3]. Reporting like this relies on compiled episode deal sheets rather than O’Leary’s own accounting, and such entries capture stated on‑air terms rather than eventual follow‑through, dilution, or later financing that affect ultimate ownership and return ^[3].

4. Losses, disclosures and the limits of public data

O’Leary himself has been open about big misses—he told CNBC he once lost $500,000 on a telecom startup that “went to zero,” underscoring that headline exits are only part of the story and that venture investing on Shark Tank mixes big hits with dramatic failures ^[5]. Aggregators and later profiles estimate O’Leary has invested roughly $8.5 million across about 40 shows, but those totals and many deal returns are obscured by legal confidentiality, private follow‑on rounds and the fact that some figures reported online are compiled by third parties not O’Leary ^{[4] [6] [5]}.

5. How to interpret “biggest” — value, size, or return

Assessing “biggest individual investments” requires choosing a metric: largest exit (Plated at $300M), largest public on‑air cheque (Zipz at $2.5M), or largest return on a small stake (Groovebook’s $75k→$14.5M sale). O’Leary and coverage from CNBC, The Street and independent trackers present all three as meaningful but distinct measures, and available sources repeatedly caution that NDAs and private deals prevent a complete, auditable leaderboard of his Shark Tank investments ^{[1] [3] [4]}.

Conclusion

Public records and O’Leary’s own statements identify Plated as his most significant financial exit, Groovebook and Wicked Good Cupcakes as high‑return, smaller investments, and Zipz as the largest single on‑air investment captured by third‑party databases, but gaps in disclosure, NDAs and private financings mean any definitive list of “biggest individual investments” remains provisional based on available reporting ^{[1] [2] [3] [4] [5]}.