Former NFL QB Alex Smith, NBA player Shane Battier, and venture capitalist Ravi Gupta have a fascinating conversation about the NFL Draft, risk-taking in sports and business, and talent evaluation. They discuss why teams overreach for quarterbacks despite their low hit rate, the importance of being bold when you have a premier leadership position, and how executives often overestimate the risk of failure while underestimating the randomness of success. 

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Ramp, the financial operation platform that simplifies everything about how businesses spend money and spend their time. You can manage spend approvals, control your expenses, automate your accounting, track your vendor relationships, book your travel and delight your entire workforce with intuitive business software. Ramp enables you to focus all of your attention on what's most important. Get started now and build a more efficient team and a more profitable business, whether you have five employees or 25,000. Go to ramp.com/gg to sign up for free and receive a $250 welcome bonus. 

—-

Glue Guys is a property of Colossus, LLC. For more episodes of Glue Guys, visit https://joincolossus.com/series/glue-guys/. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @GlueGuys_Pod | @JoinColossus

Show Notes:

(00:00:00) Welcome to Glue Guys

(00:03:00) Quarterbacks: The High-Risk, High-Reward Picks

(00:04:08) Comparing Draft Strategies: NFL vs. NBA

(00:07:57) The Role of Luck and Talent in Draft Success

(00:11:46) Venture Capital and Drafting: A Parallel

(00:20:47) Rookie Training Camp Memories

(00:21:30) The Importance of Taking Risks in Sports

(00:22:17) The Frustration of Playing It Safe

(00:23:19) The Value of Bold Leadership

(00:26:04) The Challenge of Predicting Success

(00:27:46) The Risk and Reward of Draft Picks

(00:34:36) Balancing Boldness and Caution

(00:37:01) The Role of Luck and Skill in Success

In this episode of Glue Guys, Alex, Shane, and Ravi talk with renowned sportswriter Wright Thompson about the complexities of ambition and success. Wright shares insights from his profiles of elite athletes like Jason Tatum and Michael Jordan, exploring the personal costs of excellence, the struggle to balance professional obsession with family life, and how our personal narratives shape us. The conversation reveals powerful parallels between athletic greatness and other forms of achievement, touching on Pat Riley's "Malibu retirement" myth and the universal search for meaning beyond success.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Ramp, the financial operation platform that simplifies everything about how businesses spend money and spend their time. You can manage spend approvals, control your expenses, automate your accounting, track your vendor relationships, book your travel and delight your entire workforce with intuitive business software. Ramp enables you to focus all of your attention on what's most important. Get started now and build a more efficient team and a more profitable business, whether you have five employees or 25,000. Go to ramp.com/gg to sign up for free and receive a $250 welcome bonus. 

—-

Glue Guys is a property of Colossus, LLC. For more episodes of Glue Guys, visit https://joincolossus.com/series/glue-guys/. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @GlueGuys_Pod | @JoinColossus

Show Notes:

(00:00:00) Welcome to Glue Guys

(00:01:52) Navigating Awkward Beginnings

(00:02:28) Connecting Through Shared Experiences

(00:03:12) The Invasiveness of Writing

(00:04:53) The Unique Lives of Athletes

(00:05:44) The Short Window of Athletic Careers

(00:07:51) The Struggle of Post-Retirement

(00:13:46) The Celtics' Legacy and Modern Era

(00:21:51) Balancing Ambition and Family

(00:28:14) Managing Pressure and Expectations

(00:29:39) The Fleeting Nature of Success

(00:30:10) Different Perspectives on Time and Career

(00:33:43) Faith and Freedom in Sports

(00:35:22) The Edge of Greatness

(00:30:44) The Complexity of Personal Stories

(00:47:49) The Role of Glue People

Jim “Bones” Mackay has seen it all. Three-time Masters champion caddie. The man inside the ropes with Phil Mickelson for 25+ years. And now one of golf’s most respected voices.

In this episode of Glue Guys, Bones joins us for an incredible deep dive into what really happens at Augusta during Masters Week — from the insane pressure players feel to Phil’s wildest shots to Tiger’s mental toughness.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Ramp, the financial operation platform that simplifies everything about how businesses spend money and spend their time. You can manage spend approvals, control your expenses, automate your accounting, track your vendor relationships, book your travel and delight your entire workforce with intuitive business software. Ramp enables you to focus all of your attention on what's most important. Get started now and build a more efficient team and a more profitable business, whether you have five employees or 25,000. Go to ramp.com/gg to sign up for free and receive a $250 welcome bonus. 

—-

Glue Guys is a property of Colossus, LLC. For more episodes of Glue Guys, visit https://joincolossus.com/series/glue-guys/. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @GlueGuys_Pod | @JoinColossus

Show Notes:

(00:00:00) Welcome to Glue Guys

(00:03:34) The Champions Dinner

(00:05:41) Rory McIlroy's Preparation

(00:08:33) The Role of a Caddy

(00:10:32) Phil Mickelson's Iconic Shot

(00:15:06) The Sounds of Augusta

(00:19:02) Tiger Woods and Phil Mickelson Rivalry

(00:26:13) Managing Competitiveness

(00:31:40) The Famous Veto Vote

(00:33:26) A Golf Fan's Frustration

(00:34:02) Pioneering Caddy Techniques

(00:37:24) Handling Near Misses and Heartbreaks

(00:41:18) Caddy Camaraderie and Challenges

(00:46:03) The Intensity of Team Events

(00:47:45) Ryder Cup Fever and Rivalries

(00:55:28) Gamesmanship and Mental Warfare

(01:01:04) Legacy and Craft of a Hall of Fame Caddy

(01:03:53) Personal Life and Family Support

NFL coach Dan Quinn joins the Glue Guys to share wisdom from his coaching journey. He discusses learning authenticity from mentors Nick Saban and Pete Carroll, using his Atlanta firing as an opportunity for growth, and his approach to building Washington's culture through player ownership. Quinn reveals how he creates high standards by competing in everything, celebrates "glue guys" who hold teams together, and shares his philosophy on developing both players and coaches. A masterclass in leadership from one of football's most respected minds.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Ramp, the financial operation platform that simplifies everything about how businesses spend money and spend their time. You can manage spend approvals, control your expenses, automate your accounting, track your vendor relationships, book your travel and delight your entire workforce with intuitive business software. Ramp enables you to focus all of your attention on what's most important. Get started now and build a more efficient team and a more profitable business, whether you have five employees or 25,000. Go to ramp.com/gg to sign up for free and receive a $250 welcome bonus. 

—-

Glue Guys is a property of Colossus, LLC. For more episodes of Glue Guys, visit https://joincolossus.com/series/glue-guys/. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @GlueGuys_Pod | @JoinColossus

Show Notes:

(00:00:00) Welcome to Glue Guys

(00:02:14) Introducing Dan Quinn: A Coaching Legend

(00:03:30) Learning from the Best: Saban and Carroll

(00:04:29) Authenticity in Coaching

(00:06:50) Transitioning Roles and Leadership Growth

(00:08:59) Facing Challenges and Embracing Change

(00:10:30) Feedback and Continuous Improvement

(00:13:33) Building a Winning Culture

(00:17:00) The Power of Authenticity and Team Dynamics

(00:20:08) Establishing a New Era with the Commanders

(00:24:17) The Rookie's Request and Military Influence

(00:26:25) Shared Vision and Leadership

(00:27:48) Assistant Coaches and Player Feedback

(00:30:49) Handling Departures and Succession Planning

(00:33:23) Year Two Expectations and Improvement

(00:35:08) Competing in Practice

(00:39:20) Recognizing Glue Guys and Special Teams

In this episode of Glue Guys, Alex, Shane, and Ravi recap their annual "Commissioners Cup" golf tournament. They discuss why creating time for male friendship becomes increasingly important yet difficult as men age. The trio shares memorable moments from the tournament, including rookie hazing and competition stories. Alex reveals a hilarious NFL rookie prank that left him purple for weeks, while Shane recalls his early days as a caddy. The conversation highlights how shared activities create space for authentic connection and vulnerability among friends.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Ramp, the financial operation platform that simplifies everything about how businesses spend money and spend their time. You can manage spend approvals, control your expenses, automate your accounting, track your vendor relationships, book your travel and delight your entire workforce with intuitive business software. Ramp enables you to focus all of your attention on what's most important. Get started now and build a more efficient team and a more profitable business, whether you have five employees or 25,000. Go to ramp.com/gg to sign up for free and receive a $250 welcome bonus. 

—-

Glue Guys is a property of Colossus, LLC. For more episodes of Glue Guys, visit https://joincolossus.com/series/glue-guys/. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @GlueGuys_Pod | @JoinColossus

Show Notes:

(00:00:00) Welcome to Glue Guys

(00:01:22) The Glue Guys and the Commissioner's Cup

(00:01:43) Recap of the Fourth Annual Commissioner's Cup

(00:02:40) The Spirit of Competition and Fellowship

(00:06:49) The Value of Fellowship and Activity

(00:09:26) Curating Time for Connection

(00:12:48) The Importance of Shared Experiences

(00:15:24) Building Trust and Camaraderie

(00:20:15) The Role of Golf in Men's Friendships

(00:23:10) Lessons from the Commissioner's Cup

(00:30:13) Shoutouts and Feedback

(00:31:14) Rookie Hazing Stories

(00:32:18) The Commission's Challenge

(00:34:57) Purple Prank: A Rookie's Nightmare

(00:44:12) Caddies: The Ultimate Glue Guys

(00:49:21) First Jobs and Life Lessons

The hosts share their most memorable encounters with legends and titans in their respective fields. Shane recounts playing golf with Tiger Woods, Alex discusses his first NFL start against Peyton Manning, and Ravi reflects on his early days working with private equity legends Henry Kravis and George Roberts. The conversation explores themes of imposter syndrome, earning respect, and the importance of paying forward opportunities to others. A candid discussion about what makes true greatness - not just talent, but the ability to make others feel included and elevate those around you.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Ramp, the financial operation platform that simplifies everything about how businesses spend money and spend their time. You can manage spend approvals, control your expenses, automate your accounting, track your vendor relationships, book your travel and delight your entire workforce with intuitive business software. Ramp enables you to focus all of your attention on what's most important. Get started now and build a more efficient team and a more profitable business, whether you have five employees or 25,000. Go to ramp.com/gg to sign up for free and receive a $250 welcome bonus. 

—-

Glue Guys is a property of Colossus, LLC. For more episodes of Glue Guys, visit https://joincolossus.com/series/glue-guys/. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @GlueGuys_Pod | @JoinColossus

Show Notes:

(00:00:00) Welcome to Glue Guys

(00:02:00) Playing with the Greatest Golfer Ever

(00:03:54) Nervous Moments on the Golf Course

(00:05:30) Reflecting on Brushes with Greatness

(00:11:26) Meeting Childhood Heroes

(00:14:21) First NFL Start Against Peyton Manning

(00:22:05) Learning from Business Titans

(00:34:34) Reflecting on Simple Yet Impactful Advice

(00:37:46) Facing the Combine and Al Davis

(00:38:45) Imposter Syndrome and Meeting Legends

(00:42:55) Working with Pat Riley and the Miami Heat

(00:51:56) Joining the Miami Heat and Playing with LeBron

(00:54:17) The Legendary 26-Game Winning Streak

(01:05:12) Gratitude and Mentorship

Detroit Lions quarterback Jared Goff joins the Glue Guys to share his remarkable journey from first overall pick to Detroit's beloved franchise QB. He shares the shocking moment he learned about his trade from the Rams with no warning, and how a single phone call from Dan Campbell and Brad Holmes changed his entire outlook. Jared offers candid insights into Dan Campbell's unique leadership style, including team meetings where the coach simply plays music for 15 minutes straight. The conversation touches on mentorship in the quarterback room, the evolution of his preparation routines, and how approaching fatherhood is changing his perspective as a player.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Ramp, the financial operation platform that simplifies everything about how businesses spend money and spend their time. You can manage spend approvals, control your expenses, automate your accounting, track your vendor relationships, book your travel and delight your entire workforce with intuitive business software. Ramp enables you to focus all of your attention on what's most important. Get started now and build a more efficient team and a more profitable business, whether you have five employees or 25,000. Go to ramp.com/gg to sign up for free and receive a $250 welcome bonus. 

—-

Glue Guys is a property of Colossus, LLC. For more episodes of Glue Guys, visit https://joincolossus.com/series/glue-guys/. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @GlueGuys_Pod | @JoinColossus

Show Notes:

(00:00:00) Learn About Ramp

(00:03:48) Realizing Professional Potential

(00:05:01) Freshman Year Challenges and Decisions

(00:09:35) Rookie Year Struggles and Learning

(00:13:53) The Importance of Mentorship

(00:28:19) Playoff Football and High Stakes

(00:30:49) Super Bowl Journey and Reflections

(00:33:30) The Shocking Trade Call

(00:34:30) Adjusting to Detroit

(00:36:01) Finding Out Through Twitter

(00:37:32) The Emotional Impact of Trades

(00:40:58) Embracing Detroit's Blue Collar Spirit

(00:45:33) Dan Campbell's Unique Leadership

(00:49:13) The Journey to Becoming a Better Leader

(00:53:29) Reflecting on the Season and Future Goals

(00:56:54) The Power of Team and Community

(01:02:05) Future Aspirations

Alex, Shane, and Ravi sit down with former Facebook COO Sheryl Sandberg for an insightful conversation about leadership, women in business, and corporate culture.  The NASDAQ in aggregate is worth $30 trillion and companies that Sheryl helped build make up over 10% of it. She shares personal stories from her career journey, including her early days at Google and the economic importance of women in the workforce. The discussion touches on everything from raising confident daughters to navigating big companies, with Sheryl offering unique perspectives on how to create positive change in the business world.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Ramp, the financial operation platform that simplifies everything about how businesses spend money and spend their time. You can manage spend approvals, control your expenses, automate your accounting, track your vendor relationships, book your travel and delight your entire workforce with intuitive business software. Ramp enables you to focus all of your attention on what's most important. Get started now and build a more efficient team and a more profitable business, whether you have five employees or 25,000. Go to ramp.com/gg to sign up for free and receive a $250 welcome bonus. 

—-

Glue Guys is a property of Colossus, LLC. For more episodes of Glue Guys, visit https://joincolossus.com/series/glue-guys/. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @GlueGuys_Pod | @JoinColossus

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).

Show Notes:

(00:00:00) Learn About Ramp

(00:03:40) Introducing Sheryl: Leadership Legend and Mentor

(00:04:51) Sheryl's Early Career in Government

(00:08:11) Transition to Google: The Rocket Ship Story

(00:14:03) Challenges and Misconceptions in Leadership

(00:21:44) Parenting and Gender Dynamics

(00:30:04) The Impact of Me Too and Workplace Dynamics

(00:40:19) The Power of Offering Solutions

(00:41:23) Mentorship and Gender Dynamics

(00:42:14) Coping with Personal Tragedy

(00:50:53) The Importance of Support Systems

(00:59:43) Leadership Lessons from the Top

(01:01:39) Scaling and Operating at Large Companies

(01:15:03) Balancing Culture and Performance

(01:20:44) Recognizing Sheryl’s Glue Guys

Alex, Shane, and investor Ravi discuss leadership, success, and what makes winning teams tick. The hosts explore how great leaders adapt their styles to different personalities, the importance of team culture, and why sports provide a compressed version of life's drama. The conversation touches on candid conversations about Hall of Fame inductions, creating winning environments, and the special bonds formed through competition.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Ramp, the financial operation platform that simplifies everything about how businesses spend money and spend their time. You can manage spend approvals, control your expenses, automate your accounting, track your vendor relationships, book your travel and delight your entire workforce with intuitive business software. Ramp enables you to focus all of your attention on what's most important. Get started now and build a more efficient team and a more profitable business, whether you have five employees or 25,000. Go to ramp.com/gg to sign up for free and receive a $250 welcome bonus. 

—-

Glue Guys is a property of Colossus, LLC. For more episodes of Glue Guys, visit https://joincolossus.com/series/glue-guys/. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @GlueGuys_Pod | @JoinColossus

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).

Show Notes:

(00:00:00) Learn About Ramp

(00:03:57) The Culture of Winning Teams

(00:07:33) Career Advice: Playing for Winning Teams

(00:10:30) The Pressure of High-Stakes Performance

(00:12:00) The Debate on Championships and Legacy

(00:16:50) Business vs. Sports: The Stakes and Pressure

(00:23:41) The Myth of Overnight Success in Business

(00:29:30) Understanding the Heliotropic Effect

(00:30:57) The Power of Positive Leadership

(00:34:01) Balancing Demanding and Supportive Leadership

(00:38:05) Personal Stories of Confidence and Growth

(00:41:12) The Importance of Team Dynamics

(00:43:57) Reflections on Sports and Life

(00:46:58) Honoring Achievements and Legacy

Who are you competing against? Diving into personal stories and insights, Alex, Shane, and Ravi examine the evolution from external to internal motivation across different phases of life and careers. Their competitive drives are on full display, from Shane’s fear of an unknown competitor to Alex tracking his Elite 11 peers in high school. The conversation takes an introspective turn as they discuss parenting, the challenges of transitioning from pro sports to business careers, and the importance of defining what game you're really playing. The Glue Guys give an honest look into how top performers think about finding purpose beyond competition and the value of being intentional about your goals.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Ramp, the financial operation platform that simplifies everything about how businesses spend money and spend their time. You can manage spend approvals, control your expenses, automate your accounting, track your vendor relationships, book your travel and delight your entire workforce with intuitive business software. Ramp enables you to focus all of your attention on what's most important. Get started now and build a more efficient team and a more profitable business, whether you have five employees or 25,000. Go to ramp.com/gg to sign up for free and receive a $250 welcome bonus. 

—-

Glue Guys is a property of Colossus, LLC. For more episodes of Glue Guys, visit https://joincolossus.com/series/glue-guys/. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @GlueGuys_Pod | @JoinColossus

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).

Show Notes:

(00:00:00) Learn About Ramp

(00:03:15) Defining Success: Internal vs External Competition

(00:05:44) High School Rivalries and the Drive to Prove Oneself

(00:07:42) The Evolution of Competition: From Peers to Self

(00:11:39) The Fear of the Unknown: A Powerful Motivator

(00:23:22) Adapting to Change: The Journey of an Aging Athlete

(00:37:12) Fatherhood and Internal Motivation

(00:39:17) The Unique Path and Role Models

(00:42:21) The Impact of External Motivators

(00:49:02) Parenting and Internal Motivation

(00:54:23) Defining Personal Goals and Competition

(01:00:28) The Power of Visualization and Goals