25th Hour Ideas: Recent Episodes

Michael Gallagher

Join me, Michael Gallagher, for conversations with thought leaders that will help us break free from the limits of conventional wisdom and truly scrutinize decisions made in sports, economics, and finance.

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This episode covers all aspects of preparing for game day. From planning out your training camp to checking if the kicking net is in the proper place on game day. These lessons combine the two major themes we've covered in this series, putting systems in place and viewing coaching as teaching.

''The plan must be inclusive and comprehensive in its attention to detail... An unwavering belief in developing, implementing and adhering to a well­ thought out plan for game ­day situations is a prerequisite for a first-class organization." - Bill Walsh

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How to answer the most critical question when it comes to player evaluation: "Can this individual make a meaningful contribution to the team?"

To do that we cover:
- Continually evaluating your team
- Scouting and evaluation
- Player acquisition
- Development plans
- Sound communication

All aspects required for building a successful team regardless of industry.

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Today we cover identifying the desired attributes of staff members, interviewing candidates for staff positions, determining the job assignment for each staff member, and interacting with the staff.

"The secret to managing well and motivating those you manage is to understand the fine line between losing sight of the big picture and letting others lose sight of you. If you're there when the action gets hot, the results can be spectacular. Stay in the rear echelon too long, peering through binoculars, and you'll find the competitors taking the high ground."
—Bill Walsh

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Last time we discussed how as a head coach, entrepreneur, manager, how you can intentionally design your organizational structure.

This involved having a single source of authority, a prime directive, and having systems and documentation in place to make clear to everyone in the organization what is expected of them.

So if we were to start documenting and establishing organizational responsibilities, where do we begin?

We'll cover the 49ers breakdown of their Director of Operations, then we’ll look at a similar breakdown for how Bill Walsh documented how his negotiation team should function.

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We’ve talked a lot about leadership qualities, why working as a team is important, and how to communicate in order to lead a team to overcoming adversity. Now we review how, as a leader, you can intentionally design your organizational structure using the following guidelines:

  • Having a single source of authority
  • Establishing a prime directive
  • Making people the heart of the organization

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In this episode we continue applying lessons learned about leadership and teamwork to the role of the head coach (or leader of an organization).

We talk about how to work with the players on your team, create a decision-making process, manage your time, and increase discipline.

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In this episode we apply lessons learned about leadership and teamwork to the role of the head coach (or leader of an organization).

We talk about teaching, setting the standard, and outlining roles for everyone in the organization.

These questions apply far beyond the football field and allow us to think about how we can best communicate and work with people on our teams.

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In this episode we apply lessons learned about leadership to teamwork.

We discuss how leaders can leverage their efforts, why every team's goal is to overcome adversity, and the work that leaders shouldn't be doing.

These questions apply far beyond the football field and allow us to think about how we can put our teams in the best place to succeed.

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In this episode we start where Bill Walsh starts in Finding the Winning Edge, leadership.

Why must every leader have a system of beliefs?

What qualities do successful leaders embody?

What happens if those qualities are lacking?

These questions apply far beyond the football field and allow us to think about leadership we encounter in our daily lives.

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In the season 4 of the 25th Hour Ideas podcast, we explore Bill Walsh's influential book Finding The Winning Edge. Episodes will focus on sections of his book including leadership, competition, and people. We'll take Walsh's principles of 1) having a singular focus on perfection and 2) viewing coaching as teaching and apply them to building a great team.

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Nicholas Conte has been up to a lot since our last episode two years ago. He’s the first return guest, and the wisdom shared here about being a better coach, teammate, and friend is invaluable. 

Timestamps:
(1:40) What’s changed for us the past two years
(6:50) Perspective on coaching
(10:16) What keeps players and teams from reaching their potential?
(20:30) Being nice
(27:30) Building up others
(31:40) What we'd go back and change 
(48:20) Being a good teammate
(54:10) Having a winning mindset
(1:05:40) 23rd Hour

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Tarun Sharma is a lawyer, early member of the Conduct Detrimental team, co-host of two podcasts, co-founder of the NIL clinic at the University of Minnesota Law School, and so much more.

I loved hearing from Tarun about joining the Conduct Detrimental team, his passion for sports and sports law, relationship building, and a phenomenal success story about finding and developing a community of people passionate about the same thing.

Timestamps
(1:00) Background
(4:00) Takeaways from working in pro sports
(5:50) Relationship building
(9:22) What creates a fanbase
(10:35) Benefits of social media and online communities
(17:00) Conduct Detrimental
(23:40) Figuring out new social media platforms
(27:16) Benefits of consistency
(36:10) Importance of storytelling
(38:26) NIL and experiential learning
(46:40) 25th Hour

Where to follow Tarun -
Conduct Detrimental Podcast
Conduct Detrimental Newsletter
LinkedIn
Twitter

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Arjun Menon is another rising star in the football analytics community. He’s a research and development intern at Pro Football Focus, co-host of the Take the Points podcast, a prominent contributor to football analytics Twitter, an honorable mention at the 2023 Big Data Bowl... and he’s still in college.

I learned a lot from Arjun during this conversation about the difference between football and other pro sports when it comes to analytics, what the future will look like for publicly available data, the salary cap, and how to build an analytics staff from scratch.

Timestamps

(1:57) Getting into football analytics

(6:05) Exponentially growing reach

(9:07) Football analytics vs other pro sports

(11:35) Blending data with scouting

(13:55) Future of publicly available data

(18:09) Building a personal brand

(24:15) Future goals

(26:05) Building an analytics staff

(36:27) Salary cap

(42:40) 25th Hour

Where to follow Arjun -
Take The Points podcast
LinkedIn
Twitter

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Tej Seth is a rising star in the football analytics community. He’s the newest data scientist at SumerSports, a prominent contributor to football analytics Twitter, and his group was recognized as an honorable mention at the 2023 Big Data Bowl.

I learned a lot from Tej during this conversation about how to think about data, what he looks for when watching a game, and the importance of associating your work with a personal brand.

Timestamps

(1:47) Combining analysis & public speaking

(3:30) Importance of personal brand

(5:15) Demonstrating your thought process

(10:20) Grit

(12:00) Entry to coding

(20:30) Consistency and podcasting

(24:50) What to watch for in a game

(27:00) Stability and misconceptions

(33:20) Self-scouting

(37:30) Educational content

(38:50) Measuring culture

(40:00) 25th Hour

Where to follow Tej -
Take The Points podcast
LinkedIn
Twitter

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Andrew Petcash is a rising star in the sports business world. A former D1 college basketball player, he’s the founder of Profluence and a thought leader in breaking down the business of athletes and sports.

I learned a lot from Andrew during this conversation about content creation, discipline, consistency, and building a brand from scratch.

Timestamps:

(1:23) How would you describe yourself?

(4:33) Autographs vs quote tweets

(5:52) Supporting each other and sharing wins

(9:30) Habit tracking

(12:05) Getting past the first valley

(15:23) Taking notes

(18:50) Research

(23:20) Loving what you’re doing

(26:20) Impact

(27:35) Preparing for big meetings or conversations

(32:20) Accountability and discipline

(35:55) Team mantras

(38:55) Profluence

Where to follow Andrew -

The Petcash Pod: https://profluence.com/podcasts/

Profluence Sports Newsletter: https://www.petcashpost.com/

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A surprise bonus episode! Matt Tenuta is currently having a great season in the Mexican League for the Mariachis de Guadalajara, and we recorded this episode shortly before the season started.

This is a fantastic conversation where I learned a lot from Matt about best and worst practices from various organizations, the importance of having a short memory as a pitcher, and what it was like to grow up in a family of star athletes.

Timestamps:
(1:15) Growing up among athletes
(15:30) Baseball career and being drafted out of high school
(25:30) How to not be star-struck
(34:40) Using social media
(40:20) We predicted crypto’s downfall
(44:30) Innovative income sharing strategies in baseball
(50:00) Lessons learned from organizations
(1:21:00) Chipotle
(1:23:50) Having a short memory as a pitcher
(1:33:00) 25th Hour

If you enjoy the podcast, please consider leaving a quick rating on Apple podcasts or Spotify. It would go a long way in attracting a larger audience and more fantastic guests. 

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This is a terrific episode to close out season 2. Robert Williams has nearly a decade of experience in the Navy and is currently serving as a Naval Officer, with previous roles including operations and flight instruction.

I learned a lot from Robert about leadership, time management, connecting with people, team building, and plenty more. These lessons will definitely be useful in 2022 and beyond. 

Timestamps:
(0:53) How this episode came to be
(5:06) Learning how to network
(6:40) Resumes, cover letters, and following up with people
(16:15) Four principles of time management
(32:07) Lessons learned on leadership
(45:35) My favorite excerpt from Extreme Ownership
(52:40) 25th Hour
(54:07) 23rd Hour(?!)

If you enjoy the podcast, please consider leaving a quick rating on Apple podcasts or Spotify. It would go a long way in attracting a larger audience and more fantastic guests. 

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This was a collaborative project with my friend Vincent. Vincent started The Investment Club YouTube channel in August of 2020 and has since been regularly posting videos on stock analysis, personal finance, and investment basics. 

This was a highly entertaining, and illuminating, conversation that helped demystify several financial concepts.

Disclaimer: This is intended for entertainment purposes only, not to mention this conversation was recorded months ago, so do not make any financial decisions based on what we have to say. 

Articles:
Jobs, Cook, Ive—Blevins? The Rise of Apple's Cost Cutter - WSJ

Timestamps:
(1:30) Why the importance of ratios changes over time
(14:10) Shark Tank and why cash is king
(22:37) Thinking of a stock as a pizza pie
(28:15) Why the Dow Jones means NOTHING
(34:52) Netflix and wholesale transfer pricing power
(46:22) 25th Hour

If you enjoy the podcast, writing a short review on Apple podcasts would go a long way in attracting a larger audience and more fantastic guests. 

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Jonathan Stern is the Co-founder of Pairagraph,  a platform for written dialogue between pairs of individuals. They have already hosted over 100 dialogues, with contributors like Howard Marks, Balaji Srinivasan, Joe Lonsdale, Robert Shiller, and Russ Roberts. 

This is a fantastic conversation where I learned a lot from Jonathan about the state of discourse, the pursuit of truth, and thinking about what the future will look like.

Timestamps (approximate):
(1:00) Pairagraph’s mission, and the problems with current discourse
(5:20) Dialogue on Twitter
(12:00) Benefits of market prices
(16:00) Constructive disagreements and the pursuit of truth
(18:00) Starting from 0, and another Mark Cuban story
(25:20) Partnering with Newsweek
(29:30) Expanding from the traditional format, and the benefits of the written word
(37:00) Our cultural tastes
(41:00) 25th hour

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Joe Chin and Sam Pigott, Co-Founders of Sparrow, are serial entrepreneurs who developed an app that is "golf improvement in your pocket." With Sparrow, all you need is a phone in order to improve your golf swing with instant feedback. 

During this conversation I learned a lot from Joe and Sam about starting a business, creating something scalable, thinking about the future of technology, and having skin in the game. 

Timestamps:

(1:00) Introductions and background

(4:45) History of tech in sports instruction

(10:00) pros/cons of instantaneous feedback

(14:30) Telling a story & creating great products

(27:30) Golf Genome

(31:00) The business side of startups 

(36:00) What will technology enable? 

(43:40) 25th Hour

If you enjoy the podcast, writing a short review on Apple podcasts would go a long way in attracting a larger audience and more fantastic guests. 

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Stephanie Weissenburger is a recent law school graduate now working at the law firm Geragos & Geragos, and she also plays a key role in the growth and success of Conduct Detrimental, the premier sports law podcast and blog.

Stephanie’s work is always ahead of the curve, whether it’s reporting on the Cleveland Guardians name change or the lawsuit between the city of St. Louis and the NFL. This is a fantastic conversation where I learned a lot from Stephanie about breaking into the business of sports, following your passion, goal setting, and working with people. 

Timestamps:

(2:00) Why sports law, and the pros/cons of being a sports agent

(9:30) The importance of leveraging digital media

(15:30) The rewards of curiosity

(18:50) Setting yourself apart in the sports industry

(25:50) Always ask “why”

(35:20) Survivor

(39:10) The power of being able to focus

(45:50) Long term goals and how to navigate conversations with people

(56:00) 25th Hour

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David Karasek is a coach, founder and CEO, who also happens to be a former Olympic swimmer, multiple record holder, and graduate of the University of Virginia. 

This is a wide ranging conversation about when spirituality meets peak performance, the power of the subconscious mind, the pros and cons of motivation, and how often we should think about what we want in life. 

Timestamps:

(1:00) The creative orientation

(11:30) Escaping competition through authenticity

(15:40) Differences between the conscious and subconscious mind

(28:30) Knowing what you want 

(31:10) Flywheels 

(37:30) Motivation

(44:30) The value of group work

(47:50) 25th Hour

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Steve Novak is currently a Senior Philanthropic Advisor for Boston College. He's spent the past 21 years working in fundraising for BC after starting as an intern. 

This conversation covers not only fundraising but economics, finance, college athletics, and why people and relationships are of the utmost importance. Grab your notebook because this episode will teach you something, whether it's about creating unique experiences or how to ask for millions of dollars.

Timestamps

(1:47) Steve's atypical career path in the sports industry

(3:28) Purpose of fundraising in college sports

(6:00) Athletic department revenues compared to expenses

(8:35) Importance of flexibility in fundraising

(10:58) Unique financial aspects of fundraising

(18:34) How athletics is all about experiences 

(24:15) How to make the ASK

(29:23) Making an effort to understand people, and the qualities of successful fundraisers

(35:04) Reading

(38:05) 25th hour

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Micah Kiser is going into his 4th season as a middle linebacker for the Los Angeles Rams. He won the Campbell Trophy in 2017, he was an Academic All-American at UVA, and was twice named to the First Team All-ACC.

He’s taught me a lot about football over the years, and he’s already overcome several setbacks in the NFL with persistence and determination.

This is a fascinating conversation about Micah’s approach to learning and teaching football, his style of leadership, accountability, and lessons he’s learned along the way.

Timestamps

(4:43) Micah’s approach to learning and teaching football

(8:16) Setting priorities

(12:36) Leadership during transition, and what changed for Virginia in December 2015

(19:11) Takeaways from the 2016 season

(23:20) Being 400% committed and accountable

(30:41) Transferring habits to the NFL

(34:26) NFL honors

(41:03) Lessons learned that will help Micah run his future organization 

(49:48) 25th hour

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This conversation really made me think. Dan Hatman has a wealth of experience as a scout, coach, and student of football. His paper on all things related to NFL general managers is a fantastic resource. In this conversation he talks about economics as it relates to football, improving the talent pool for general managers, and best practices regarding organizational culture.

The Scouting Academy

Timestamps 

(3:48) How the Bears drafted Trubisky

(6:55) Thinking probabilistically, and behavioral economics

(11:03) Twitter

(18:28) Economics and football decision-making

(28:25) Opportunity cost of NFL draft picks

(34:42) Obstacles for crowdsourcing scouting

(44:24) Research on GMs

(53:57) Improving the GM talent pool

(1:01:34) Fascinating Dave Gettleman story

(1:09:37) Active listening

(1:17:15) Organizational culture

(1:23:54) 25th hour

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Adam Harstad is a phenomenal thinker. Over the past couple of years I've seen him distill complex ideas from several disciplines and apply them to fantasy football. This episode covers interesting frameworks that transcend football, including risk homeostasis, second-order thinking, resource allocation, and many more. You can find a collection of his writing here.

Timestamps

(2:12) How to figure out what to write about

(5:12) Risk homeostasis

(19:21) Future of quantifiable stats, and measuring second-order effects

(40:47) Probability

(53:24) Danger of a plausible narrative

(1:01:37) Consistency in fantasy football

(1:10:45) Strong opinions, weakly held

(1:19:37) Twitter

(1:25:57) How to choose a GM, and how to manage draft strategy

(1:45:03) Principal-agent problem in football

(1:54:58) Measuring rates of change

(1:59:06) Resource allocation

(2:03:54) Zero-sum games

(2:13:15) 25th hour

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Canaan Severin is not only one of the greatest WRs in UVA history, but he's also a film writer and director. He just released his first film "Lean In" earlier this month. 

Since graduating from Virginia, Canaan spent time in the NFL with the Steelers and Giants. In this episode he shares stories from his football career about systems, habits, the importance of people, and the power of believing in yourself.  This is a master class on persistence and designing systems built for success.

If you haven't already, writing a short review on Apple podcasts would go a long way in attracting a larger audience and more fantastic guests. 

Timestamps:

(2:09) Canaan’s one handed catch against Miami coming full circle

(9:46) How you do one thing is how you do everything, and applications to recovery

(15:40) The importance of nutrition

(22:25) Current goals and systems

(27:00) Mentors at UVA

(34:15) Compartmentalization in football

(41:20) Culture and people

(53:55) Canaan’s ideal 25th hour

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Henry “The Hammer” Coley was a leader of the 2014 Virginia Cavaliers. I’ve always wanted to ask him about leadership, his approach to learning the game, and how his skills have translated to life after football. 

Since graduating with his Master’s, Henry spent time in the NFL before becoming a consultant and entrepreneur. Henry is a leader everywhere he goes, and this conversation is filled with important lessons.

If you haven't already, writing a short review on Apple podcasts would go a long way in attracting a larger audience and more fantastic guests. 

Timestamps:

(1:50) Lessons on leadership

(9:09) Dynamics of a football team

(11:13) Leadership role at UVA, and the concept of a living resume

(19:34) Memorable moment following a 2014 win

(25:45) The difference between NFL and college football

(31:33) How to study game film

(38:45) Life after football and an important lesson I learned from Henry

(45:18) How Henry would use a 25th hour

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Nicholas Conte, specialists coach at VMI and decorated former UVA punter, teaches a masterful lesson on mindset and achieving high performance. This transcends football.

Our conversation spans the mental side of playing and training, the role of specialists in games and practice, proper nutrition, and Conte’s journey from UVA to VMI and one day soon the NFL.

If you haven't already, writing a short review on Apple podcasts would go a long way in attracting a larger audience and more fantastic guests. 

Timestamps:

(2:47) Why special teams is unique, typical practice for specialists

(7:38) Pre-game warmup and common pitfalls

(16:52) Punter’s role during the game

(24:50) Process oriented thinking

(34:50) Mindset

(39:08) Training methods

(46:26) Role of student managers

(52:43) Nutrition

(56:04) Our mutual admiration for Trent Corney

(1:02:17) Conte’s ideal use of a 25th hour

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Alex is currently working towards his Master's in Data Science at the University of Virginia. Not only has he been working for the UVA football team in an analytical capacity, but he also presented his own research at the NFL's Big Data Bowl in 2020.

I came across his paper and was eager to reach out to him. Our discussion covers the deficiencies of traditional box scores, judging information in context, predicting individual vs team performance, and how all this work will go from behind the scenes to on the field.

Links mentioned:
ESPN analytics survey
Virgil Carter - Operations Research on Football
Pulling the Goalie: Hockey and Investment Implications
Data, Decisions, and Basketball with Sam Hinkie
Inside Football Podcast with Bill Polian

Transcript
Newsletter

Timestamps:

1:51 Alex’s time at Big Data bowl and his direction for research

4:56 First exposure to data analytics

6:52 Traditional box scores

9:44 Analytics and fantasy sports

12:19 Judging information in context

15:52 Player vs team modeling

19:38 EPA vs WPA

24:38 Increasing variance as the underdog

30:02 How does this work go from behind the scenes to on the field?

35:44 Unpopular roster management decisions

38:42 Individual performance, success rates, and tracking data

40:48 Adopting analytics, communication

44:05 Spin on 25th hour question

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Chris Saave is an entrepreneur I’ve been fortunate to see in action the past few years. We cover his thoughts on starting a business, the importance of learning, finding hidden knowledge, and how to take risks.

Many of these lessons have helped me along my entrepreneurial journey. Chris has certainly stepped his game up with his latest venture, Meet Me Card.

If you enjoy the episode, you'd love my weekly newsletter with updates on new episodes and blog posts, as well as a summary of the coolest things I learn each week.

Referenced works:
"Why books don't work" by Andy Matuschak 

Timestamps:

(1:03) How we crossed paths

(3:12) How do you get the right idea to start a business?

(9:05) Dealing with the sunk cost fallacy

(12:16) Importance of reading

(18:12) Focus

(22:49) Sight beyond sight

(24:32) Finding hidden knowledge

(28:27) Process of learning new skills

(32:09) Judging by quantity vs quality and the quest for perfection

(35:18) Just do it, avoid regrets of omission, take calculated risks

(41:31) The history behind Meet Me Card and how Chris applied all these lessons

(50:43) Chris’ ideal 25th hour

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Who better to ask about leadership than the person who started the most games at quarterback while I was at UVA? Matt Johns, currently the quarterbacks coach at William & Mary, loves football. His actions and words have always been in alignment, and that's just one of the many lessons I've learned from him over the years.

If you enjoy the episode, you'd love my weekly newsletter with updates on new episodes and blog posts, as well as the coolest things I learn each week.

Timestamps:

(3:10) The transition between coaching staffs and Matt’s role with UVA

(7:25) Buy-in to team culture and seeing the big picture

(9:11) Chop wood and carry water

(10:10) What football teaches you about life

(17:15) Matt’s experience as a coach

(19:17) Matt’s year as a GA at Virginia

(27:20) Why do you like football?

(33:39) Who taught Matt the most about leadership?

(36:40) Lessons learned from Coach London

(43:40) Prepping for the football season

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This conversation with Jackson Matteo is special.  We cover his time at Virginia chronologically, from walk-on to graduate assistant coach, and examine how our relationship evolved along the way.  I have learned so much from Jackson about commitment, discipline, and total effort.

Jackson is currently working on his dissertation, and he explains why his topic of choice is important and prevalent.

If you enjoy the episode, you'd love my weekly newsletter with updates on new episodes and blog posts, as well as the coolest things I learn each week.

Timestamps:

0:50 - How we know each other

6:45 - Jackson's high school sports career

10:28 - The difference between football and basketball

16:57 - Betting on yourself

24:04 - Eating healthy and having it pay dividends

26:59 - The 2016 transition in culture at Virginia

32:42 -  Lessons learned from a historic level of losses

35:59 -  Emotional Intelligence

40:30 - Jackson's perspective as a coach as opposed to player, and the 10/80/10 principle

47:50 - The two factors Jackson measures himself against, as learned from Coach Howell

52:28 - Jackson's dissertation 

59:42 - How would Jackson spend a 25th hour?

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When you're part of a team, consistency is an invaluable trait. Sean Cascarano has that trait in spades. Sean is currently an Assistant Coach at Cornell where he coaches the offensive line. He's consistently been dedicated to his team and to teaching the fundamentals.

In this episode we discuss lessons Sean learned from coaching at multiple colleges, the importance of consistency within college programs, and how to build an organization from the ground up.

If you enjoy the podcast, I would greatly appreciate it if you took the time to leave a short review on Apple Podcasts. It really makes a difference in helping to grow our audience and attract guests.

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Harkening back to Dwight D. Eisenhower, "plans are useless, but planning is indispensable." Few people I know are as detail oriented as Jacob Hodges. He not only provided me with an invaluable opportunity at UVA (in response to a 2014 email that gets read on the podcast), but he's taught me a lot over the years. Since our shared time at Virginia, Hodges has become a math teacher and the offensive coordinator of Atlee High School. In this episode we discuss paying attention to detail, where to find learning material, and the benefits of having perspective.

If you enjoy the podcast, I would greatly appreciate it if you took the time to leave a short review on Apple Podcasts. It really makes a difference in helping to grow our audience and attract guests. 

Thank you.

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This week I'm thrilled to be learning more from Zach Tenuta. Since our shared time at Virginia, Zach has become the Co-Defensive Coordinator and Linebackers Coach at Norfolk State University. Zach and I discuss the process of learning and developing as a coach, the importance of having mentors, and recount the time we had to drop $100 at a Kinko's.

If you enjoy the podcast, I would greatly appreciate it if you took the time to leave a short review on Apple Podcasts. It really makes a difference in helping to grow our audience and attract guests. 

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For the first official episode my guest is none other than Kaveh Akbari (@kaveh_akbari), a certified NFL player agent and expert marketer. Kaveh and I discuss the role of agents, what goes into creating your own agency, using leverage in a negotiation, my plans for a signed picture of me and Adam Cole, and many more issues involving economic concepts and the NFL.

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If you enjoy the podcast, I would greatly appreciate it if you took the time to leave a short review on Apple Podcasts. It really makes a difference in helping to grow our audience and attract guests. 

View Details

The best time to start this podcast was several years ago. The second best time is now. Learn what's to come, what exactly the 25th hour even is, and where you can find more of my work.

Spoiler alert: it's all at 25hourideas.com