The most controversial change in pickleball history happened overnight. The community exploded with criticism and conspiracy theories.

Tito Machado, CEO of DUPR, breaks his silence with complete transparency about why they overhauled their entire rating system and what really happened behind the scenes.

🎧 TIMESTAMPS:(00:00) Intro(02:15) Company secret: The Anna Leigh Waters example (05:30) Why simple win/loss systems don't work for pickleball(08:45) The inflation crisis destroying rating accuracy(12:20) Pennsylvania vs Florida: When 5.0s aren't equal(16:10) The deflation trap for competitive players(19:45) Why protecting your rating hurts the entire community(23:30) Reliability: The most overlooked rating factor(27:15) Truth behind viral "extreme drop" posts(31:40) The gender and age rating debate(35:20) Battle of the sexes challenge issued live(38:50) How to actually improve your DUPR rating(42:10) 80% accuracy: The data that changed everything

In this raw conversation, Tito reveals:- The company secret about Anna Lee Waters that explains everything- Why they kept a broken algorithm for 2 years- How rating inflation was destroying competitive integrity - The real story behind viral posts of extreme rating drops- Why reliability matters more than your rating number- How 8 million games of data led to 8% better accuracyThis isn't just about pickleball ratings - it's about the courage to choose accuracy over popularity, and what happens when you build in public.

What happens when you spend your entire twenties chasing the wrong dream?

Kaitlin Miller gave up everything to become a TV news anchor. She moved to Nashville, sacrificing weekends, holidays, and relationships to climb the media ladder. Then, just as she was making it in a major market, she had an epiphany that changed everything.

🎧 TIMESTAMPS:(00:00) Opening: Why athlete stories matter beyond highlight reels(01:20) Her "biggest failure": abandoning the TV news dream(04:15) What the failure taught her about adaptability(07:30) From people pleaser to value-driven decision making(10:45) The real sacrifices made chasing dreams(13:20) Growing pickleball community and accessibility(16:40) Petey Bruce's incredible survival story(19:15) Why pickleball beats tennis/golf for accessibility(22:00) The career pivot decision process (pros vs cons)(25:30) Facing criticism: "Your company will fail"(28:45) PickleCon and building authentic communityIn this raw conversation, Kaitlin opens up about:- The "failure" that felt like an identity crisis- Why your goals are allowed to change as you grow- The decision framework she used to pivot careers- How pickleball is breaking down barriers other sports can't- The homeless man with no hands whose life was saved by community- Facing criticism when your boss says "your company will fail"

This isn't just another success story - it's an honest look at what it means to abandon your dreams in service of who you're becoming.

If you've ever felt trapped by goals that no longer serve you, this conversation will give you permission to pivot.

How do you go from cutting patterns with rulers and French curves to becoming the compression wear choice of NBA stars, NFL pros, and top Pickleball players?

In this episode, Alec sits down with Jonathan Oe, founder of Leorêver, to unpack the decades-long story behind one of sports' most trusted performance brands—handcrafted from scratch with paper, scissors, and relentless intention.

Jonathan opens up about the failures that nearly ended his business, the meditation practice that transformed his mindset, and why he believes elegance and excellence should never be separated. From creating custom-fit tights for Brandon Ingram to redefining recovery for athletes like Andre Daescu and Caitlin Christian, this episode is a masterclass in craftsmanship, resilience, and leading with heart.

Whether you're building a brand, pushing your limits as an athlete, or turning adversity into purpose—this one's going to stick with you.

TIMESTAMPS:00:00 – Intro: The man behind Leorêver
01:43 – From CPA to compression wear: Jonathan's unlikely origin story
04:05 – Designing gear that helps athletes feel stronger
06:24 – Brandon Ingram, thigh width, and custom builds for NBA players
09:12 – "Balanced compression" vs. tightness: why most gear is wrong
12:32 – Building confidence through design: a life-changing story
16:09 – The 2008 collapse: nearly losing everything
18:25 – From failure to factory: the long road to trust
21:40 – Zen meditation in Kyoto and becoming "180 degrees different"
24:28 – Anger as sacred fuel: channeling pain into performance
26:46 – Leorêver enters pickleball: Megan Fudge, refs, and recovery
29:44 – Loud shirts, deep strategy: the design philosophy
32:40 – Why Leorêver will never go retail
34:59 – Elegance, expansion, and doing it the hard way
36:48 – Final reflections: legacy, energy, and building slow

#Entrepreneurship #Athletics #PerformanceWear #BusinessStory #Mindset #Craftsmanship #NBA #Pickleball #StartupJourney

What happens when a seasoned executive from the NHL steps into one of the fastest-growing sports in America?

In this episode, Alec sits down with Mike Nealy, former Arizona Coyotes President and now the CEO of USA Pickleball, to unpack the strategy, struggles, and surprising psychology behind building a sport from scratch.

Mike opens up about the unexpected similarities between hockey and pickleball, failures he faced behind the scenes that no one saw, and what it really takes to earn credibility in a passionate but skeptical community.

Whether you're an entrepreneur, athlete, or just obsessed with watching new industries explode — this is a masterclass in leadership, adaptability, and staying humble through scale.

0:00 - Intro: From the NHL to Pickleball
2:10 - Why Mike left professional hockey for a niche sport
4:25 - Early mistakes with USA Pickleball and the learnings
6:43 - “Credibility is earned, not given” – building trust in a new space
9:55 - What Mike learned about failure from elite athletes
12:12 - The underestimated power of community in growth
14:40 - The business psychology of USA Pickleball and beyond
17:50 - Turning backlash into buy-in: how to manage public criticism
21:04 - Structuring a new sports organization from scratch
25:33 - The role of data, storytelling, and ESPN in pickleball’s future
28:44 - Mike’s advice to anyone entering a disruptive industry
33:17 - When to lead and when to follow: learning in real time
36:45 - Final thoughts: legacy, ego, and letting go of control

Welcome to another episode of the Fail First Podcast! Today’s guest is the dynamic Connor Derrickson, widely known as “That Pickleball Trainer.”

Connor brings a fascinating story—from his time as a strength and conditioning coach for the Minnesota Twins, to now training amateur and pro pickleball players. In this episode, we dive into:

• How he overcame five knee injuries and rebuilt himself

• Merging exercise science with pickleball

• Why mental training is just as critical as physical training

• What optimal off-court training looks like for longevity and performance

Whether you’re a casual player or chasing a pro dream, this one’s packed with insight, vulnerability, and actionable tools.

🎯 Find Connor Here:

• YouTube: @ThatPickleballTrainer

• Instagram: @thatpickleballtrainer

🕒 Timestamps:

01:50 – From Pro Baseball Trainer to Pickleball Trainer

05:27 – Imposter Syndrome in Pickleball Training

08:37 – Overcoming Five Knee Injuries

10:56 – “Overcoming Athlete Setbacks”

14:25 – “Consistency: Key to Athletic Success”

17:48 – Strength Foundation in Athletes

20:39 – “Foundational Movements Build Strength”

23:12 – “Earning Trust Through Performance Testing”

29:00 – Improving Stamina in Sports

30:20 – Enjoyable, Sustainable Fitness Routines

32:47 – Phased Training for Performance Improvement

36:11 – Off-Season Sports Training Approach

40:31 – “Underrated Wall Drills in Training”

44:25 – Training for Longevity in Sports

47:29 – Force Absorption & Movement Training

51:55 – Fitness Goals: Weight Loss & Optimization

53:59 – Embracing Failure for Growth

On this episode of the Fail First Podcast, host Alec Martone sits down with Dr. Brandon Bentzley for a fascinating conversation bridging the worlds of plasma physics, neuroscience, and mental health innovation.

Dr. Bentzley shares his unique journey—from conducting NASA plasma physics research to pioneering cutting-edge psychiatric treatments at Stanford and through his company, Magnus Medical. Together, they explore:

• How solving world-changing problems led him from space to the human brain

• Groundbreaking work with neurostimulation therapies like SAINT (Stanford Accelerated Intelligent Neuromodulation Therapy)

• How advanced brain imaging is personalizing mental health treatments

• Why restoring a sense of agency and free will could be one of the greatest gifts of medicine

They also dive into the future of mental health care, the science of resilience, and the hurdles in accessing truly effective treatments.

This is a hopeful, science-driven episode for anyone passionate about innovation, recovery, and redefining human potential.

🎯 Find Dr. Bentzley’s work at:

• Magnus Medical: https://magnusmed.com

🕒 Timestamps:

0:00 – Intro

08:47 – Create a Career You’d Do Free

10:51 – Thoughts on Identity and Behavior Conflict

20:39 – “Scalable Brain Mapping Technology”

25:39 – Interrupting the Depression Loop

31:38 – AI Uses Classical Deep Learning

33:30 – Massive Models Needed for Brain-Like AI

38:49 – 3D Brain Scan Insights

46:50 – Translating Trials to Patient Impact

53:45 – Personalized Brain Treatment Strategies

58:18 – Halo Neuroscience: Boosting Skill Acquisition

01:04:42 – Exercise Lowers Depression Risk

01:10:36 – “Magnus Licenses SAINT, Achieves FDA Clearance”

01:13:52 – Automated Workflow for Device Use

01:19:48 – Medical Device Investment Challenges

01:24:05 – Marketing Success Needs Big Budgets

01:31:21 – Mental Health: Options Often Overlooked

01:33:47 – Consider These Depression Treatments

01:43:04 – Health Insurance: Mental Health Parity

01:44:56 – Medicare Mental Health Payment Barrier

01:49:45 – Greatest Fear Moving Forward

In this episode of the Fail First Podcast, we sit down with Tom Webb, the chief marketing officer of the world's first pickleball tour. Tom shares his incredible journey from working with global giants like Formula One and Red Bull to diving into the exciting world of pickleball. You'll hear about the potential of pickleball as a rapidly growing sport and the innovative ways the Association of Pickleball Players (APP) is working to elevate the game, both for pros and amateurs alike. With insights on building a tribe, creating top-tier content, and the future of pickleball on a global scale, Tom offers valuable lessons on marketing, competition, and how to transform obstacles into opportunities. Whether you're a pickleball enthusiast or just curious about the business side of sports, this conversation will leave you inspired and informed.Find APP HERE:  @TheAPPTour  [00:00:00] Introduction [00:01:14] Tom Webb discusses his career transition to the pickleball industry and his attraction to startup-like organizations.[00:02:35] The explosion of pickleball during lockdown and its popularity according to data.[00:03:45] The opportunity to shape an emerging sport as it gains mass participation.[00:05:45] Ken Herman's founding of APP and its historical context.[00:06:30] The mission to represent all pickleball players, focusing on inclusivity.[00:08:40] Building community identity and the psychological aspects behind sport growth.[00:13:18] Using strategy and content to create a cohesive player and fan community.[00:19:12] Audience data and viewership comparisons with other sports.[00:22:45] Importance of maintaining quality in production to boost viewership.[00:37:06] Expansion into international markets and efforts to grow pickleball globally.[00:46:28] Long-term goals for APP and the desire to create identifiable branding.[01:07:54] Potential for sports betting in pickleball and the requirements needed before implementation.[01:26:07] Efforts to enhance player visibility and personal branding through storytelling.[01:34:36] Discussing the steps needed for pickleball to become an Olympic sport.[01:50:37] Tom Webb's reflections on past actions perceived as failures and how these informed future decisions.[01:59:40] Personal insight and concluding thoughts from Tom Webb on maintaining a balanced life.

In this episode of the Fail First Podcast, we sit down with Curtis Smith to delve into the meteoric rise and innovative journey of Paddletek in the pickleball industry. Curtis shares the inspiring origin story of how he was initially skeptical about the sport but ultimately convinced by his brother to embrace the potential of pickleball, leading to the rise of Paddletek. Listen as Curtis reveals the challenges of manufacturing in the US, the importance of physics over gimmicks in paddle design, and the company’s dedication to maintaining high performance and integrity in their products. This episode not only covers the technicalities and innovations behind Paddletek paddles but also provides valuable insights into leadership, entrepreneurship, and the grit required to overcome significant industry challenges. Whether you're a pickleball enthusiast or intrigued by business innovation, this conversation is packed with valuable lessons and a testament to the power of believing in groundbreaking ideas.00:00:00 - Intro.00:00:29 - The initial reluctance followed by realization of the potential of pickleball.00:01:23 - Curtis shares the origin story of Paddletek, from a garage startup to a major brand.00:01:44 - The first major event in Arizona, and the overwhelming response.00:06:57 - Discussion on Curtis's career background prior to Paddletek.00:07:22 - The inspiration from his grandfather and the transition from corporate to entrepreneurship.00:11:31 - Importance of not just gimmicky innovations.00:16:31 - Evolution of paddle technology from initial designs to current models.00:16:31 - R&D focus on player needs and performance.00:16:31 - Story of specific paddle innovations, such as the Anna Leigh Waters paddle.00:18:41 - Adjustment and improvement process based on player feedback.00:31:36 - Discussion on PB core testing and its importance.00:31:36 - Exploration of paddle design and future innovation perspectives.00:47:11 - Paddletek's adjustments during the period of change (pandemic, market pressures).00:47:11 - Strategic decisions regarding manufacturing location and material sourcing.00:42:57 - The decision to pay players during the pandemic.00:42:57 - The relationship with Anna Leigh Waters and Christian Alshon.01:18:35 - Reasons behind merging with Pro XR and boundless pickleball under UPP.01:18:35 - Anticipated benefits in innovation and market strategies.01:47:02 - Concerns about the evolution of the sport and maintaining its original appeal.01:47:02 - Paddletek’s commitment to maintaining manufacturing in the USA and focusing on innovation.01:57:15 - Curtis reflects on leadership and company culture.01:57:15 - Grateful Failure, Greatest Fear

In this episode of the Fail First Podcast, join us as we dive into the world of Diadem Sports with co-founder Evan Specht , who shares the story behind their mission, "live to play." Evan provides an inside look at how Diadem is pushing boundaries in innovation both in the tennis and pickleball industries. Discover how they are redefining pickleball with their groundbreaking BluCore technology and why they've chosen to focus on the everyday player rather than the professional scene. We'll explore Evan's personal journey from coaching tennis, to knowing  @JamesIgnatowich  kryptonite on the pickleball court and dominating him in Japan, to learning about all the challenges and triumphs Diadem has had along the way. Tune in for a conversation that inspires both athletes and entrepreneurs to pursue passion with purpose.
BluCore Paddles , launching Spring 2025! [00:00:04] Introduction to Diadem Sports and Philosophy* [00:00:04] Quote: Tennis and pickleball as platforms for connection* [00:00:32] Mantra: "Live to Play"* [00:00:32] Emphasis on sports as a source of fun and passion[00:02:20] History and Development of Diadem Sports* [00:02:20] Origins and growth of the company* [00:02:20] Introduction of the Dynasty team, a junior program* [00:02:20] Evolution from tennis-focused to incorporating pickleball[00:02:56] Diacon Event* [00:03:14] Purpose and significance of Diacon* [00:03:31] Features of the event: human connection, product reveals, and networking* [00:06:02] Financial considerations and decision-making behind organizing Diacon[00:09:25] Business Strategy* [00:09:25] Marketing and investment strategies* [00:09:25] Importance of networking and human connection in brand growth* [00:09:25] Transition from focusing on the pro game to including average players[00:14:44] Pickleball and Facilities Expansion* [00:14:44] Entering the pickleball market* [00:14:44] Investments in pickleball complexes and facilities* [00:14:44] Opportunities presented by the sport's growth in the US and internationally[00:31:05] Product Development and Innovation* [00:31:29] Introduction of Blue Core technology for paddles* [00:32:08] Characteristics of Blue Core: durability, consistency, and dwell time* [00:35:29] Multiple shapes and thicknesses of paddles using Blue Core technology[00:51:39] Shoe Line: Court Flow and Court Burst* [00:51:39] Development of a new line of shoes for pickleball and tennis* [00:52:44] Technical features and target customers for Court Flow and Court Burst* [00:56:39] Considerations for comfort, support, and pricing in shoe development[01:03:46] Marketing and Product Diversification* [01:03:46] Strategy involving the release of unconventional products like the Vice paddle and Hush paddle* [01:11:55] The introduction of the Diadem pickleball* [01:14:41] Marketing strategy focusing on community and customer connection[01:20:33] Business Challenges and Responses* [01:20:33] Navigating the COVID-19 pandemic* [01:23:57] Strategic pivots and innovations in response to industry challenges* [01:23:57] Consistent focus on organic growth and customer engagement[01:28:54] Conclusion and Vision for the Future* [01:28:54] Desire to become a leading brand in pickleball* [01:31:23] Importance of human connection and embodying the "Live to Play" mantra* [01:31:23] Long-term vision of global expansion and recognition in pickleball

In this episode, we dive into the inspiring journeys of our guests, Jack Munro and Jaikin Gomez, as they navigate the world of pro pickleball and beyond. From Jack's strategic approach to building a brand beyond playing, to Jaikin's reflections on transforming his basketball past into pickleball potential, this episode offers insightful lessons on perseverance and adapting to life's unexpected turns. Whether you're an aspiring athlete or simply looking for motivation, tune in to uncover how embracing failure can propel you toward success.1. [00:00:00] Introduction2. [00:00:16] Jack Munro's Career and Content Creation * [00:00:16] Transition from just playing pickleball to establishing a career. * [00:00:34] Importance of creating a niche for younger audiences with trick shots and highlights. * [00:01:38] Commitment to daily Instagram posts for brand building and content creation challenges. * [00:01:41] Reasons for content creation: * As insurance in case of an injury affecting his pro career. * Financial benefits from building a social media following. * Desire to be known beyond just being associated with pickleball.3. [00:02:54] Introduction to Jaikin Gomez * [00:03:03] Alec Martone asks Jaikin to introduce himself. * [00:03:13] Jaikin mentions participation in Next Gen and his connections to Miami.4. [00:03:33] Pickleball Match Discussion * [00:03:33] Jack Munro discusses his experiences in matches against Jaikin Gomez. * [00:04:01] Challenges of playing against left-handed players. * [00:04:29] Jack's preference for playing against right-handed players due to strategic and geometric reasons.5. [00:05:29] Jaikin Gomez's Pickleball Experience * [00:05:31] Transition from recreational play to Next Gen. * [00:06:08] Importance of tournament experience and mindset. * [00:06:42] Comparing talents and consistency in performances.6. [00:07:01] Success and Mindset in Pickleball * [00:07:01] Discussion on navigating pressures and tournament routines. * [00:08:10] Importance of maintaining consistency and managing emotions in matches.7. [00:09:20] Failures and Lessons Learned * [00:09:20] Jaikin Gomez reflects on his basketball experience and its life lessons. * [00:11:20] The role of work ethic and adapting to new roles in basketball and pickleball. * [00:12:43] Jack Munro's experiences with content creation criticism and qualifying for tournaments. * [00:12:43] Financial and mental challenges in pursuing a professional pickleball career. * [00:12:43] The significance of a growth mindset in overcoming setbacks.