The ongoing drama between BJJ superstar Gordon Ryan and premium flip-flop brand Toehold has taken another turn, with Ryan releasing additional leaked text exchanges and audio recordings that shed new light on their failed partnership negotiations.
In newly shared audio recordings from AG Gregoroff of Toehold, the company’s representative can be heard discussing delays in finalizing their sponsorship agreement. The audio reveals significant hurdles in getting their legal documentation completed:
“I definitely don’t want to change the initial agreement at all. I just want to make sure everything is done proper… This might take the better part of several months to get done. Our attorney is on one of those f**king annual world traveling, f**king finding himself f**king journeys. I think his dad just died and he was like, all right, I’m going to take off for three months since you guys don’t need me and go travel the f**king world.” – AG can be heard saying in one of the voice notes.
The recordings suggest that Toehold‘s legal delays contributed to the partnership’s collapse, with their attorney apparently unavailable for months due to personal travel following a family death.
Perhaps the most revealing aspect of the leaked messages is the disclosure of Ryan‘s sponsorship terms. The text exchanges show that Ryan was set to receive $5,000 per month for wearing Toehold gear exclusively. In a January 2025 message, Ryan pressed for clarity on the arrangement:
“Also need to know if you still wanna do the 5k a month for me to wear toe hold stuff exclusive, bec I have venum that keeps harassing me to work with them. I get if it doesnt make sense and money is tight, I just need to know bec I dropped future on the assumption that we are doing something, so if we aren’t, I’ll use venum.”
The mention of Venum is particularly significant, as the major combat sports brand sponsors the UFC and has been expanding into grappling.
Ryan‘s sponsorship history has been marked by controversy and failed partnerships. Industry observers point to speculation that his previous partnership contributed to the bankruptcy of BJJ brand Hypnotik. More recently, his relationship with Future Kimonos ended amid public disputes, with that company facing widespread customer complaints about delayed orders and poor service that have flooded forums like r/BJJ.
The pattern has led some to question whether Ryan‘s sponsorship demands are sustainable for smaller brands in the niche grappling market.
The leaked messages reveal Toehold‘s financial struggles, with the company announcing they were “draining cash reserves to build the new headquarters” and would be “shutting down the headquarters and putting Toehold on life support.”
In their statement, Toehold claimed that Ryan‘s promised $1 million investment “never materialized” despite months of negotiations, and that they “never received the funds, nor did we receive a signed contract to formalize the agreement.”
Despite Ryan‘s release of these supporting documents, public reaction has been largely unsympathetic. Much of the skepticism stems from Toehold‘s business model itself – selling premium flip-flops that regularly cost $500-$1,000, compared to other premium sandal brands that retail for around $60.
Critics have pointed out the absurdity of the situation, noting that these expensive flip-flops “shouldn’t even get wet” despite their premium price point, making the entire sponsorship dispute seem somewhat ridiculous to outside observers.
While Ryan‘s star power in the grappling world is undeniable, his track record of difficult partnerships raises questions about the sustainability of his approach to sponsorship deals.
