Bet On Yourself with Angelo Pitirri

Angelo Pitirri
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Bet On Yourself isn’t for the ones who already made it, it’s for the ones who feel hesitant to start. Hosted by entrepreneur and author Angelo “Gege” Pitirri, this show dives into real stories of risk, resilience, loss and rebuilding. From failure to success, Angelo shares honest lessons on turning hesitation into belief and doubt into drive, inspiring you to finally make your own bet on yourself.

Episodes

  1. FEB 23

    Bob May: Accepting the Results, Betting On Yourself (Season 2 Episode 3)

    What happens when you bet on yourself…work harder than anyone else…and still feel like you didn’t reach your own expectations?In this episode of Bet On Yourself, former PGA Tour professional Bob May opens up in one of the most honest conversations of his career.From being the #1 junior golfer in California…to winning internationally…to competing in the final group at a major championship against Tiger Woods at the 2000 PGA Championship…This conversation goes far deeper than golf.It’s about identity.It’s about pressure.It’s about regret.It’s about learning to accept the result even when it doesn’t match the dream.Bob reflects on:• Growing up outside the traditional golf pipeline• Being coached with negative reinforcement• Losing confidence in college & dealing with Dyslexia• The mental battle of competing at the highest level• The emotional aftermath of taking Tiger Woods to a playoff at Valhalla• Living with unmet expectations• Redefining success beyond trophiesThis isn’t a highlight reel interview.It’s a raw conversation about what it really means to bet on yourself — and what happens when the outcome doesn’t look the way you imagined.If you’ve ever worked your entire life toward something and still felt like it wasn’t enough… this one will hit home.0:00 – “I Worked So Hard… And Never Did”1:05 – The #1 Junior Golfer in California4:40 – Beating His Coach 150 Times6:30 – Playing Arnold Palmer as a Young Pro9:00 – Respect vs Arrogance on Tour12:00 – Negative Coaching & Lost Confidence17:00 – Elite Ball Striking Philosophy29:00 – Did I Live Up to My Own Expectations?30:55 – Winning on the European Tour33:00 – Competing at the Highest Level38:40 – The Playoff at Valhalla41:00 – Regret, Identity & Acceptance48:30 – Success Beyond Trophies55:40 – Advice for the Next Generation#BetOnYourself#BobMay#TigerWoods#pgachampionship #mindsetshift #Valhalla#GolfPodcast#Mindset#Resilience#PersonalGrowth#HighPerformance

    1h 6m

  2. FEB 16

    Jasmine Jasudavicius on Sacrifice, Loss, and What It Really Takes to Fight in the UFC. Season 2 EP2

    In this conversation, Jasmine Jasudavicius opens up about the real cost of chasing greatness physically, mentally, and emotionally.We talk about:Starting MMA later than mostFear and nerves before walking outFighting through pain and injuryLosing in front of your countryThe pressure of being a woman in a brutal sportSacrifice, humility, and resilienceand what it truly means to Bet On YourselfWhat makes this episode special is how natural and honest the conversation is especially considering Jasmine and Angelo had just met before sitting down.This isn’t a hype interview.It’s a real conversation about discipline, loss, and choosing to keep going.🎙 Season 2, Episode 2Watch & Subscribe:    / @betonyourselfpodcast  Shop the collection: www.betonyourselfstore.comOfficial site: www.angelopitirri.comCoaching: www.betonyourselfcoaching.comProdigy Personnel: www.prodigypersonnel.com0:00 – It’s time0:36 – Giving up tickets & why the moment mattered1:23 – How the podcast started from loss2:48 – Bankruptcy, poker, and betting on yourself4:59 – Business vs fighting: control & competition6:40 – How Jasmine found MMA at 268:50 – First sparring, first fights, falling in love with it10:45 – Turning pro & early nerves12:20 – Fear before walking out13:50 – Being smaller, proving yourself15:26 – Tunnel vision, losses, and learning the hard way16:22 – Carrying the weight of Canada18:25 – Neutral thinking, grief, and loss20:08 – Family after a loss22:19 – Life after fighting23:37 – Growth of women in MMA25:46 – Training vs the fight27:49 – Hardest skills to learn28:47 – Advice to young athletes31:48 – Who shaped Jasmine’s mindset33:44 – Cardio, emotion, and fatigue36:13 – Respect after the fight37:06 – A full training camp breakdown39:44 – Living in pain as a fighter40:14 – Being a woman in the sport41:04 – Fighting with a broken orbital44:28 – Championship goals46:14 – Life as a contender47:34 – What betting on yourself really meansCredits:Produced & Edited by Noah Bollert (@noahbollert)Sound & Set by Noah Bollert (@noahbollert)Behind the Scenes by Mario McLennon (@mclennon_22)

    50 min
  3. Jasmine Jasudavicius

    FEB 16

    Jasmine Jasudavicius

    We talk about:Starting MMA later than mostFear and nerves before walking outFighting through pain and injuryLosing in front of your countryThe pressure of being a woman in a brutal sportSacrifice, humility, and resilienceand what it truly means to Bet On Yourself

    48 min
  4. Jack Lenz (PART B)

    11/07/2025

    Jack Lenz (PART B)

    In Part B of our two-part conversation, Canadian icon Jack Lenz opens up about faith, purpose and legacy.From composing OK Blue Jays, Goosebumps and Nanalan to writing music inspired by his Bahá’í faith, Jack shares how his spiritual convictions have guided a lifetime of art.We dive into his work supporting human rights, women’s equality and unity across cultures and how music can be a force for healing and change.This episode is about more than a career it’s about a calling.It’s what it means to build a life with intention and leave a legacy that lasts.Credits:Noah Bollert-Editing & ProductionNick Pitirrri- Set & SoundDedicated to the One’s that rounded me enough to sit with Jack!www.angelopitirri.comwww.betonyourselfcoaching.comwww.betonyourselfstore.com#BetOnYourself #JackLenz #TheLegacy #OKBlueJays #Goosebumps #Nanalan #CanadianIcon #BahaiFaith #FaithAndArt #HumanRights #WomensEquality #Inspiration #SpiritualJourney #PurposeDrivenLife #Creativity #CanadianMusic #podcast #Angelopitirri #Gege #HighStakesHeadspace #BetMade #SoloCollection #Motivation #PersonalGrowth #Mindset #BetOnYourselfPodcast #emotional #mindset

    42 min
  5. Jack Lenz (PART A)

    11/06/2025

    Jack Lenz (PART A)

    In this powerful first episode of Season 2, Bet On Yourself, host Angelo Pitirri sits down with legendary Canadian composer Jack Lenz, the creative force behind OK Blue Jays, Goosebumps, Nanalan, Due South and countless iconic works.Together they open up about:The grief of losing family and how gratitude helps us heal.The story behind OK Blue Jays, Canada’s most loved ballpark anthem.Mentorship, faith, and finding your calling through service.Turning anxiety into purpose and art into legacy.Part A The Heart focuses on emotion, courage, and creativity.Part B The Legacy will explore Jack’s faith, equality work, and fight against human trafficking.Watch & Subscribe: youtube.com/@BetOnYourselfPodcastShop the collection: www.betonyourselfstore.comOfficial site: www.angelopitirri.comCoaching: www.betonyourselfcoaching.comProdigy Personnel: www.prodigypersonnel.comCredits:Produced & Edited by Noah Bollert (@noahbollert)Sound & Set by Nick Pitirri (@buttonboards)Dedicated to the one's that round me enough to be able to sit at a table with JackBig thank-you to Jeffreyt Welsh, The Cooperators, for supporting Season 2 episode 1 of Bet On Yourself.Your partnership helps bring stories like Jack Lenz’s to life. 💛♠️#BetOnYourselfPodcast #JackLenz #BlueJays #OKBlueJays #FaithInAction #EntrepreneurMindset #CourageToStart #Goosebumps #CanadianMusic #Mentorship #GriefAndGratitude #PodcastCanada #BetMade #BetOnYourselfStore #AngeloPitirri #BetOnYourselfCoaching #nanalan #goosebumps #Olympics1996 #motivation #faith #god #baseball #coaching #mindset #youtube #creators #mindsetshift #youtubevideo #spotifypodcasts #applepodcasts

    1 hr

  6. 07/18/2025

    Winning Friendships, Real Bets & The Power of Showing Up | Bet On Yourself Podcast

    Welcome back to Bet On Yourself, where today’s roundtable takes you inside the real life of competition, camaraderie, and the honest (sometimes hilarious) moments that define high performers.💥 BOYS vs GIRLS CONTEST — WATCH & WIN! 💥Support your favorite squad and help them win bragging rights (and prizes 👀) by doing the following:✅ 1 Point – Watch the episode✅ 3 Points – Like the video✅ 5 Points – Leave a comment (mention your team: “Team Girls” or “Team Guys”)✅ 10 Points – Make a purchase from our official merch store: https://betonyourself.shop🛍️ Use these discount codes at checkout:🎀 GIRLS25 – for Team Girls merch🧢 BOYS25 – for Team Guys merch📊 We’ll track the results and post updates on Instagram @angelopitirri — every view, like, comment, and purchase counts!Let the battle begin. 🏆#TeamGirls vs #TeamGuys — who you got?What’s Inside This Episode🏆 High-stakes competition and friendly rivalry: From the golf course to the locker room and beyond, discover how declaring your goals and facing challenges head-on builds confidence—and why real victories demand you show up.🤝 Friendship, follow-through, and accountability: Hear the group’s honest takes on paying your bets, keeping your word, and why real relationships are grounded in trust and transparency.💡 Life advice for all ages: Get unfiltered advice about moving on, growing up, and finding personal balance—from surviving heartbreak and academic hurdles to owning your actions and planning your next move.🤗 Team chemistry over talent: Find out how genuine relationships turned a hockey team into champions, and what it teaches us about winning together in business and life.🧠 Mentorship, mindset, and next-gen tools: Learn about the impact of wise mentors, the importance of setting goals, and how embracing tools like ChatGPT gives you an edge.😂 A few laughs, a few confessions, and a lot of real talk: Enjoy the humour, humility, and honesty that make every Bet On Yourself roundtable a can’t-miss.If you love shows about confidence, business & investing, learning from failure, or real talk on friendship and growth—this is your home.Subscribe, drop questions in the comments, and join us as we bet on ourselves—and help you do the same.00:00 Intro & Setting the Table00:24 Bet On Yourself—What It Means00:36 Golf Games, Losing Bets & Friendly Rivalries01:14 The Jessica Challenge & Summer Competition01:31 Declaring Matches—Lessons on Confidence02:13 Competing for Real: Match Play vs Scoring03:35 Healthy Competition & Friendships04:12 Shell Games & College Stories05:13 Owing Money & Accountability06:39 Who Do You Trust Under Pressure?07:14 Breakups, Loneliness & Finding Yourself08:05 Supporting Each Other & Staying Connected08:41 Dating, Reputations & Silent Moves09:25 Relationships & What Comes Next09:48 Planned Breakups & Big Life Changes10:17 Dealing with Moving Away, Homesickness & Defeat10:37 The Power of Talking & Making a Plan11:14 Academic Struggles, Tutors & Mirrors12:12 Advice for Going Away to School12:30 Finding Balance in University Life13:43 Partying, Peer Pressure & Setting Boundaries14:03 Drugs, Fentanyl & Staying Safe15:17 Lessons on Friendship & Potential15:33 Hockey, Drafts & Feeling Left Behind16:27 Hard Truths About Talent & Opportunity17:38 Offensive Zone Penalties & Team Dynamics18:37 Coaches, Championships & Winning Chemistry20:22 Firehouse Challenge & Team Bonding20:40 Celebrating Wins: Chemistry Makes Champions21:41 Trophy Stories & Legendary High School Parties23:33 Finding the Missing Trophy24:42 Favorite Moments & High School Memories25:13 Near Misses & Championship Reflections26:30 Athletic Ability—Who’s Got What?27:05 Deserted Island Choices—Survival & Teamwork28:24 School Recommendations & Academic Grit29:01 Friendship Boundaries & Dating Lines29:22 ChatGPT, Mindset & Business Tools29:46 Rock-Paper-Scissors Showdown30:43 Champion’s Mindset & Trickery31:00 Outro & Final Laughs

    31 min

  7. 07/10/2025

    The Grad-Girls vs Boys Part A “The Broads” 6 Teen Girls on Identity, Sports, Loss, Life & Religion

    This is the episode we’ve been waiting for. Part 1 of a two part episode, The Boys will be next. We will be counting Views, Comments, Likes & Merch Purchases for the Girls & Boys to establish a winner of the Episode. For Merch purchases simply go to our store and use your winning vote code of GIRLS25 or BOYS25 to get 25% off compliments of the winning team you select.Six smart, strong, and emotionally aware teenage girls, including my own daughter Jessica, join me for one of the deepest and most honest conversations we’ve had on the Bet On Yourself podcast.We talk about everything:Identity beyond sportsMental health and therapyFirst heartbreaksNavigating confidence and popularityReligion, grief, and losing my sisterACL Injuries, Sports Scholarships, Self Confidence, Self Help, Stay away from drugs, Mental health advice.This isn’t just a conversation about high school — it’s a reflection on who we are becoming, and how to stay grounded when the world keeps moving fast.Watch until the end. There are tears, wisdom, and a message every parent, coach, and young woman needs to hear.👉 Subscribe for more episodes and behind-the-scenes content🎧 Also available on Spotify, Apple, and all major platforms👕 Merch: https://angelopitirri.com then clich Merch 📲 Follow on IG: @betonyourself.pod#BetOnYourself #BetOnIt #BetMade #BOYpodcast #NeutralThinking #LiveInTheMoment #MindsetMatters #PresentNotPerfect #GrowthMindset #TeenVoices #GradGirls #GradBoys #HighSchoolLife #SeniorYear #MentalHealthAwareness #YouAreMoreThanYourSport #GriefAndHealing #FaithStruggles #GodAndIArentOkay #GirlsSupportingGirls #RealConversations #GirlDad #PodcastClip #PodcastHighlight #PowerfulWomen #ComingOfAge #LifeAfterSports #StudentAthlete #TeenConfidence #ACLRecovery #JordanaWisdom

    46 min

  8. 06/17/2025

    Accept the Mirror When Shown: Rebrand, Rebuild & Inject Confidence | Ep. 4 w/ Nurse Rebecca

    What happens when someone holds the mirror up and you don’t look away?In Episode 4 of Bet On Yourself, Angelo Pitirri and Nurse Rebecca get into what it takes to truly change:Accepting the truthFacing the truthRebranding your identity personally and professionallyRemoving people who wronged you without losing your empathyShowing up with confidence when the world underestimates youThis episode dives deep into mindset shifts, the business of aesthetics, and the emotional toll of transformation all told through raw stories and real-life lessons.🎙 Full episode available now on YouTube, Spotify & Apple Podcasts🔗 www.angelopitirri.com🔗 www.prodigypersonnel.com👉 Subscribe for new episodes weeklyhttps://www.youtube.com/@Betonyourselfpodcast#BetOnYourselfPodcast #AcceptTheMirror #RebrandRebuildRise #NurseRebecca #MindsetShift #SelfAccountability #StoriesAndLessons #ConfidenceCoach #MedicalAesthetics #AestheticNurse #GlowUpSeason #EntrepreneurMindset #SelfWorth #YouTubePodcast #SpotifyPodcasts #EmpoweredWomen #BotoxBusiness #BeautyAndBusiness #Episode4What happens when someone holds the mirror up and you don’t look away?In Episode 4 of Bet On Yourself, Angelo Pitirri and Nurse Rebecca get into what it takes to truly change:Accepting the truthFacing the truthRebranding your identity personally and professionallyRemoving people who wronged you without losing your empathyShowing up with confidence when the world underestimates youThis episode dives deep into mindset shifts, the business of aesthetics, and the emotional toll of transformation all told through raw stories and real-life lessons.🎙 Full episode available now on YouTube, Spotify & Apple Podcasts🔗 www.angelopitirri.com🔗 www.prodigypersonnel.com👉 Subscribe for new episodes weeklyhttps://www.youtube.com/@Betonyourselfpodcast#BetOnYourselfPodcast #AcceptTheMirror #RebrandRebuildRise #NurseRebecca #MindsetShift #SelfAccountability #StoriesAndLessons #ConfidenceCoach #MedicalAesthetics #AestheticNurse #GlowUpSeason #EntrepreneurMindset #SelfWorth #YouTubePodcast #SpotifyPodcasts #EmpoweredWomen #BotoxBusiness #BeautyAndBusiness #Episode4

    51 min
  9. Episode 3 — $300K Invested. COVID Hit. Banks at Her Throat. | Chelsea Spencer on Bet On Yourself

    06/02/2025

    Episode 3 — $300K Invested. COVID Hit. Banks at Her Throat. | Chelsea Spencer on Bet On Yourself

    🎙️ Episode 3 of Bet On Yourself with Angelo PitirriWhat happens when you finally chase your dream — and the world shuts down two weeks later?In this raw and emotional episode, Coach Chelsea Spencer joins host Angelo Pitirri to talk about risking everything to build a business… only to have COVID hit weeks later. Over $300,000 invested. No support. And the banks at her throat.But this isn’t just about entrepreneurship.It’s about identity, loss, mentorship, faith, and finding your voice — even when the world goes silent.Chelsea opens up about:The injury that ended her soccer career and shattered her sense of selfCrying herself to sleep, praying for guidance, and rebuilding from the ground upStarting a high-performance coaching business in the middle of a global crisisDiscovering her worth through community, coaching, and beliefAND… proudly declaring she’s single — “for any hot guys listening!” 🔥Angelo shares:His own struggle with grief and a God he doesn’t always understand — “Why are you picking on my mom?”His deep respect for Chelsea’s courage and mindsetThey also talk spirituality when Chelsea suggests visiting an angel reader, and Angelo unexpectedly finds himself open to the message.The episode wraps with a heartfelt book conversation on:📚 The Midnight Library — What if you could try the lives you never lived?📚 The Abundance Book — A mindset shift that reframes what you’re really chasingWhether you’re building something, breaking down, or simply trying to believe in yourself again — this episode will move you.💥 Real talk. Real stories. Real growth.00:00 - Cold Open: COVID, $300K, and No Support 01:15 - Episode Intro 02:00 - How Chelsea and Angelo First Met 04:00 - Signing the Lease Before COVID Hit 05:30 - Financial Pressure & No Government Support 07:00 - Breaking Down and Praying for Help 08:45 - Angelo's Mentorship & Community Support 11:00 - Emotional Toll and GoFundMe Story 13:00 - Chelsea's College Soccer Journey 16:00 - Sixth Concussion: Losing Her Identity 18:30 - Finding Purpose in Coaching 20:15 - Mentors, Moms, and Mindset 23:00 - Betting on Yourself with Nothing Left 25:30 - The Real Meaning of Support 28:00 - Empowering Girls in Sport 30:00 - Injury Stories and Mental Resilience 34:00 - Mental Health, High Rocks & Identity 38:00 - Chelsea’s Take on What BOY Means 41:00 - Angel Readers, Faith & Fighting for Purpose 44:00 - The Midnight Library & The Abundance Book 48:00 - Chelsea’s Academy, Big Plans & Being Single 50:00 - Final Thoughts: What Betting on Yourself Really Means 🔔 Hosted by Angelo Pitirri — Entrepreneur, Author, and creator of Bet On Yourself➤ Subscribe on YouTube: www.youtube.com/@UCC19BZIz896ClcJj0qX-wJw ➤ Listen on Spotify: https://open.spotify.com/show/29Yusy9hKxMfXIeUDuSkYL➤ Apple Podcasts: https://podcasts.apple.com/ca/podcast/bet-on-yourself-with-angelo-pitirri/id1809036090💥 Follow Chelsea Spencer: chelseaspencer.ca@empowerfutbolwww.empowerfutbol.ca#ChelseaSpencer #AngeloPitirri #BetOnYourselfPodcast #EntrepreneurStory #CovidBusiness #InjuryRecovery #Resilience #FaithStruggles #AngelReader #TheMidnightLibrary #TheAbundanceBook #Podcast #StartupStruggles #AthleteToEntrepreneur #MindsetMatters #god #womenempowerment

    58 min

  10. 05/23/2025

    Episode 02: Bold Design, Risk-Taking, and Building a Business in Muskoka

    Christina Carr, founder of CC Interiors, who shares what it’s really like to build a bold creative business in Muskoka.From walking away from a secure job at 24 to shaping luxury spaces across Ontario’s cottage country, Christina’s journey is a masterclass in betting on yourself, especially when the stakes feel personal.🎯 This episode is about:Making brave choices in beautiful placesRedefining success as a woman in designTrusting your instincts in uncertain momentsCreating space—physically and emotionally—for growth🎙 Recorded in Muskoka📍 Hosted by Angelo Pitirri🌲 Brought to life in Ontario’s cottage country, where the grind meets the getaway🔗 Learn more at angelopitirri.com🎧 Subscribe for weekly drops that blend ambition and lifestyle#BetOnYourself #ChristinaCarr #MuskokaBusiness #WomenInDesign #LuxuryCottageLife #CreativeEntrepreneur #JaynesCottages #PodcastCanada #InteriorDesign

    43 min
  11. Episode 01: Getting To Neutral

    05/15/2025

    Episode 01: Getting To Neutral

    From pro poker to Prodigy Personnel. From bottomed out to building a $50M firm. In this premiere episode, Angelo Pitirri opens up like never before. You’ll hear the real, gritty version of his journey: the wins, the walls, and the wake-up calls that forced him to level up—personally and professionally. From managing CRA audits and back-end chaos to honouring his sister’s legacy with a life insurance payout no one saw coming, this episode is a behind-the-scenes look at the moment when betting on yourself isn’t inspirational—it’s survival. Jeff Welsh, long-time friend and fellow entrepreneur, joins Angelo for an unfiltered conversation that hits on what it means to get to neutral—to remove ego, emotion, and expectation, and just take the next right step forward. Topics Covered: Angelo’s early business mistakes—and how he bounced back. The pressure of going all-in with no fallback plan. Why neutral thinking saved his mindset. Compliance, CRA letters, and the sh*t no one prepares you forHow one conversation in Vegas changed everything. Quoting Trevor Moawad’s It Takes What It Takes, Angelo lays out the mental frameworks that helped him grow through chaos—and gives tactical advice for new founders trying to do the same. Want the book “It Takes What It Takes” but can’t afford it? Angelo’s buying. Just message him: angelo@angelopitirri.com. This episode is more than a backstory—it’s a blueprint for what betting on yourself actually looks like when you’re under pressure, underfunded, and still find a way. #BetOnYourself #Entrepreneurship #StartupStories #NeutralThinking #BusinessGrowth #AngeloPitirri #PodcastLaunch #RealBusinessTalk #FounderLife

    37 min

  12. 04/18/2025 · BONUS

    Episode Zero

    In this launch episode, host Angelo Pitirri shares the raw, inspiring story behind the Bet On Yourself podcast. From an unexpected childhood uprooted by divorce to overcoming personal bankruptcy, and ultimately building a $50 million staffing firm, Angelo opens up about the defining moments that shaped his journey. This episode sets the tone for what's to come: real conversations about entrepreneurship, resilience, relationship-building, and yes — a few tips and tricks for navigating Vegas like a pro. You'll hear about Angelo's early lessons in business, his pivot from professional poker to running a successful company, and his deep belief that betting on yourself is the ultimate investment. Future episodes will bring on guests ranging from NHL players like James Wisniewski to sports betting experts, entrepreneurs, and everyday risk-takers who have defied the odds. If you're ready to turn setbacks into setups and build a life on your own terms, this podcast is for you. Subscribe, follow, and get ready to Bet On Yourself.

    12 min
  • 12 Episodes

About

Bet On Yourself isn’t for the ones who already made it, it’s for the ones who feel hesitant to start. Hosted by entrepreneur and author Angelo “Gege” Pitirri, this show dives into real stories of risk, resilience, loss and rebuilding. From failure to success, Angelo shares honest lessons on turning hesitation into belief and doubt into drive, inspiring you to finally make your own bet on yourself.

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