541: Skills, Struggle, and Responsibility. With Jimmy May.
Jocko Willink reunites with former SEAL teammate Jimmy May to discuss parenting philosophies, Jimmy's adventure-based executive team building company Mayday Executive, and the growth of Beyond the Brotherhood, a nonprofit helping high-risk veterans transition to civilian careers. The conversation covers lessons from raising children with responsibility and autonomy, the veteran suicide crisis, and an upcoming NYC charity swim aiming to raise $1 million.
Summary
The episode opens with Jocko introducing Jimmy May, a former Navy SEAL who served at SEAL Team 2, attended language school for Arabic, joined Task Unit Bruiser in Ramadi, survived a gunshot wound to the chest, and eventually retired as a commander after serving as XO at BUD/S and deputy commander at CJ-SOTIF. Jimmy has been featured on episode 405, and this appearance focuses on his post-retirement activities.
A significant portion of the conversation centers on Jimmy's LinkedIn series called 'Dad Drops,' where he documents parenting lessons learned with his youngest son Riker. Key philosophies discussed include: letting children build things themselves to create ownership and value (paralleling leadership lessons about letting teams build their own plans); assigning maintenance responsibilities with real pay to teach work ethic and financial literacy; letting children set their own rules to combat psychological reactance; preparing excess capability before it's needed; teaching reverence for life even for pests; the importance of press checks and knowing the condition of your weapon; and defeating learned helplessness by resisting the urge to solve problems for children. Jimmy reflects candidly that he missed much of his older two children's childhoods due to 300+ deployment days per year, and views raising Riker as a second chance.
Jimmy's company Mayday Executive is described as an adventure-based team building and executive experience company where he designs custom high-stakes experiences for corporate clients and YPO/EO groups — including spearfishing, pit maneuvers, J-turns, shooting ranges, and other extreme activities. He explains that overcoming fear and stress in these controlled environments produces lasting lessons that transfer to boardroom performance. He is booked through February of the following year entirely through word of mouth and repeat clients.
The episode also covers Jimmy's invention venture with his brother — the Cable Pilot, a device that improves safety and efficiency for telecom tower workers by simplifying cable routing around splice plates. A patent was filed in November, and the product is available at mayday.solutions.
The largest segment covers Beyond the Brotherhood (BTB), the nonprofit Jimmy founded four months after retirement when four teammates died by suicide, including one he had spent the weekend before with. BTB screens and selects high-character veterans — particularly those most at risk, the operators who were put in harm's way most frequently — and provides them with personality assessments, medical support to get off medications accumulated during service, VA claim assistance, mentorship from civilian industry professionals, and job placement across multiple industries. The screening process involves one superior, one peer, and three subordinate references to ensure consistent character across all levels. Over 60 fellows have gone through the program with zero suicides. Jimmy discusses the painful experience of losing key staff member Sean Murphy to a better-paying opportunity, and praises new executive director Drew Forsberg for his analytical complement to Jimmy's visionary style.
The episode concludes with discussion of the NYC Seal Swim — a 3.5-mile charity swim around the Statue of Liberty and back into New Jersey, with stops for push-ups and pull-ups at barges, involving 300 swimmers including Dakota Meyer. The goal is to raise $1 million for BTB. The conversation also touches on California politics, COVID policy failures, government spending (including $160 million on prisoner iPads and the high-speed rail debacle), organized crime parallels to government corruption, and the broader erosion of public trust in institutions.
Key Insights
- Jimmy May argues that the same high-character operators who were put in harm's way most frequently — the 'best guys' — are paradoxically the ones most at risk for suicide after leaving service, because they accumulated the most physical and psychological damage.
- Jimmy claims that of the 11 waivers given to candidates over 28 years old to attend BUD/S during his tenure as XO, zero made it through, attributing this to insufficient physical recovery speed in older bodies.
- Jimmy observes that letting a child set their own rules — rather than imposing them — eliminates the need for enforcement reminders, citing his son voluntarily setting a bedtime alarm after being given autonomy over the decision.
- Jimmy describes 'psychological reactance' as a natural human instinct to push back against being told what to do, arguing it applies universally to children and adults in leadership contexts.
- Jimmy contends that the transition from military to civilian life is devastating for veterans because the military simultaneously removes identity, community, structure, and purpose — not just employment.
- Jimmy argues that screening veteran candidates using one superior, one peer, and three subordinate references is critical because character should appear consistent across all levels of the chain of command, and discrepancies reveal hidden issues.
- Jimmy claims that in his experience with Mayday Executive, Canadian participants who had never touched a gun were visibly shaking upon first handling firearms, and that by the end of sessions they typically expressed that guns weren't inherently dangerous when properly trained.
- Jimmy states that the phenomenon of 'learned helplessness' — where repeated failure causes people to give up on solvable problems — is actively created in children when parents consistently swoop in to solve their problems for them.
- Jocko argues that a child who has never attempted to learn a skill often doesn't understand that skills require practice to acquire, citing his daughter believing she should simply 'know' her multiplication tables without studying.
- Jimmy argues that the veterans most likely to struggle after separation are not low-performers but rather the highest-performing operators, making targeted selection of at-risk individuals more effective than broad outreach.
- Jimmy contends that getting veterans off accumulated medications — including opiates and NSAIDs taken to stay on the line during active duty — is a necessary first step before any career transition work can be effective.
- Jimmy claims his BTB fellows are regularly 'poached' by employers offering salaries the nonprofit cannot match, and frames this as a feature rather than a bug — evidence that the program produces highly valuable civilian professionals.
- Jocko argues that the COVID-era policy of closing schools while keeping liquor stores and dispensaries open fundamentally damaged government credibility, compounded by the fact that no officials have publicly acknowledged or apologized for those decisions.
- Jimmy argues that just as technology and RICO laws dismantled organized crime's ability to hide money and insulate leadership from street-level crimes, similar technological transparency is now exposing government fraud and misappropriation of funds.
- Jimmy claims that exposing people to controlled high-stakes experiences — such as entering water with a known shark nearby or executing pit maneuvers in cars — produces stress inoculation that transfers meaningfully to high-pressure professional environments.
Topics
Full transcript available for MurmurCast members
Sign Up to Access