#105 David Guttman: Leading Your Career With Humility

In a candid conversation from his Miami office, veteran tech executive Dave shared insights from his journey from IT consultant to running companies with thousands of employees. A former wrestler and Division I athlete, Dave's path has been anything but conventional - from managing a help desk at 24 to leading multiple successful exits and navigating the volatile crypto space. Known for interviewing every single employee when he joins a company (whether it's 20 or 100 people), his philosophy centers on humility and service to others. "If someone isn't humble, doesn't matter what their talent stack looks like," he says about his top hiring criteria. After raising millions in capital, managing over a dozen acquisitions, and developing innovative business models that disrupted established players, Dave's most profound insight might surprise you: success isn't about being the smartest person in the room, but about being the most willing to learn from others. His advice to spend 100 hours a year mastering new skills (just 18 minutes daily) offers a practical roadmap for continuous improvement in an era often characterized by quick fixes and instant gratification.

Here's what you'll learn from this interview with Dave:

• How a veteran tech executive approaches hiring - why humility trumps talent and experience, and his unique strategy of interviewing every single employee when joining a company

• A practical framework for skill development: the "100-hour rule" that explains how spending just 18 minutes daily on any skill can put you in the top 5% of practitioners

• Why focusing on individual employees first (rather than company objectives) counter-intuitively leads to better business results, and how to implement this "servant leadership" approach

• Inside stories about raising capital and scaling companies - including how investors often act like "sheep" and why it's sometimes harder to raise $500K than $5M

• A contrarian view on career development - why "do what you love" is bad advice, and how to instead build a career by systematically stacking skills and choosing the right mentors

SHOW NOTES

Key Topics & Timestamps

[00:00] - Introduction and early career background

• First job at Anderson Consulting (now Accenture)

• Early lessons about equity and company value

[15:00] - Education and career development

• Why he chose Wharton for his MBA

• Experience at the Small Business Development Center

• The value of practical experience over classroom learning

[30:00] - Building and scaling businesses

• Raising initial $450,000 from angel investors

• Completing 13 acquisitions in 18 months

• Running a 500-person company by age 29

[45:00] - Leadership philosophy and hiring insights

• Why humility is the #1 hiring criteria

• The importance of interviewing every employee

• How focusing on individuals leads to company success

Quotes

"If someone isn't humble, doesn't matter what their talent stack looks like... you won't take in new information." "I focus on the person first and the company second."

Resources Mentioned

• Book: "Influence" by Robert Cialdini

• Book: "48 Laws of Power" by Robert Greene

• Book: "How to Lose at Almost Everything and Still Win Big" by Scott Adams

Key Takeaways

1. Spend 100 hours per year on any skill to reach the top 5%

2. Focus on people first, company objectives second

3. Humility is the most important quality in hiring

4. Building through service to others leads to success

5. Choose who you work for over job title or company name

Get In Touch

Connect with Dave on LinkedIn

#104 Jared & Jordan Schmidt: How Two Brothers Disrupted The Cutlery Industry

In this candid conversation, Jordan and Jared Schmidt share the remarkable story of building Schmidt Brothers Cutlery from their father's basement workshop into a national brand found in over 10,000 retail stores. Their journey reveals invaluable insights about entrepreneurship and innovation:

• The brothers discuss how their contrasting backgrounds – Jordan's philosophy degree and bartending experience paired with Jared's business education – created the perfect partnership for building their brand.

• They reveal how the 2008 financial crisis inspired them to revolutionize the knife industry by making premium German steel knives affordable, challenging traditional industry assumptions about pricing and design.

• The conversation explores their innovative approach to retail partnerships, including how their unique butcher shop-themed trade show booth caught the attention of Williams-Sonoma and led to their first major retail deal.

• They share intimate details about their father's influence on the business, from his engineering expertise to his guiding philosophies of "sleep on it" for decision-making and "it is what it is" for handling setbacks.

• The interview concludes with insights into how they've maintained a lean operation of just 30 employees while scaling nationwide, emphasizing their approach to hiring self-starters and maintaining quality across different market segments.

Key Topics & Timestamps

[00:00] - Introduction and family background

• Father's immigration from Germany as a mechanic/engineer

• Mother's restaurant family heritage

• Learning craftsmanship in their father's basement workshop

[15:00] - Early careers and education

• Jordan's unique path: Philosophy degree and bartending

• Jared's business and supply chain background

• How different backgrounds complemented their business

[30:00] - Starting Schmidt Brothers Cutlery

• Impact of 2008 financial crisis

• Developing first product line

• Breakthrough at International Housewares Show

• First partnership with West Elm

[45:00] - Building the Brand

• Innovation in knife block design

• Approach to different retail markets

• Maintaining quality while scaling

• Building a lean team

Quotes

"Sleep on it" - Their father's advice about patient decision-making "It is what it is" - Philosophy for handling business challenges "Never close doors behind you" - On maintaining professional relationships

Links

• Schmidt Brothers Cutlery: https://schmidtbrothers.com

#103 Albert Chow: Fear Can Be A Healthy Motivator

This interview explores the journey of Albert Chow, co-founder of Silk & Snow, a Canadian sleep & lifestyle company that started as a mattress-in-a-box business. Chow discusses how his immigrant parents and blue-collar background influenced his business approach, particularly his focus on supply chain transparency and quality manufacturing. Through organic growth and without outside funding, the company evolved from a Kickstarter campaign in 2017 to a successful acquisition by Sleep Country in 2023, maintaining its commitment to sustainable, high-quality products throughout its growth.

In this episode we discuss:

-Why Albert emphasizes the importance of staying true to your values, even when faced with trends or easier paths

-Why he advocates for strategic risk-taking, noting how he first "de-risked" his life (established career, marriage, home) before starting his business

-Why operating with a healthy amount of fear can be a powerful motivator

-Being passionate about what you do is essential since your career occupies 60-70% of your life

#102 Amir Loloi: The Importance of Reputation

This is the story of Amir Loloi, the founder of Loloi Rugs, one of the largest rug companies in America. It traces his remarkable journey from arriving in Dallas as a 16-year-old Iranian immigrant in 1976, barely speaking English, to building a 650-person company that has transformed the rug industry. Through early jobs at Burger King and driving an ice cream truck, to spending 25 years learning the rug business before starting his own company, Amir shares how his father's advice to "walk a straight line" shaped his business philosophy of integrity and constant improvement. The interview explores how he built his success through reputation and relationships, eventually bringing his two sons into the business to help create a lasting legacy. It's a quintessential American dream story that illuminates the power of perseverance, the importance of reputation, and the value of staying focused even after achieving success.

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[00:00] - Introduction & Early Life

• Background on Amir's family in Iran

• Father's career as accountant turned businessman

• Growing up with artistic family members

[03:45] - Coming to America

• Arriving in Dallas at age 16 in 1976

• Initial plans for education

• First flight memories and emotions

• Being first Iranian student at his school

[08:30] - Early Jobs & Language Learning

• Working at Burger King and learning English

• Pushing to work front counter despite language barrier

• Baskin-Robbins experience

• Ice cream truck business in South Dallas

[13:15] - Education Journey

• Attending Richland College

• University of Texas Dallas

• Working full-time while studying

• Asking parents to stop financial support

[17:45] - Entering the Rug Business

• First job in 1979

• Starting from sweeping floors

• Building relationships with designers

• Rising through the ranks

[22:30] - Meeting His Wife

• University romance

• Three years of dating

• Her support in business decisions

• Balancing family and work

[26:15] - Major Career Decision

• Leaving 25-year career

• Emotional departure process

• Six months of planning

• Starting Loloi in 2004

[31:00] - Building Loloi

• First showroom in Atlanta

• Industry support and relationships

• Manufacturer partnerships

• Early customer loyalty

[35:45] - Sons Joining the Business

• Steven's education and career path

• Cyrus's journey from California

• Their fresh perspectives on branding

• Family dynamics in business

[41:30] - Leadership Philosophy

• "Walking a straight line" principle

• Focus on continuous improvement

• Employee happiness priority

• Building company culture

[46:15] - Current Business Status

• 650+ employees

• Company growth

• Maintaining independence

• Industry partnerships

[50:45] - Looking to the Future

• Legacy hopes

• Advice for entrepreneurs

• Thoughts on American opportunity

• Messages for next generation

[54:30] - Closing Thoughts

• Reflections on journey

• Gratitude for opportunities

• Final words of wisdom

Key Quotes: "The moment you think you're successful is when you lose focus." "Walk a straight line." - Amir's father's advice "This is the only country that allows someone like me to come and be as successful as we are."

#101 Dan Martell: How to Buy Back Your Time

Dan Martell is the bestselling author of “Buy Back Your Time” and a growth coach for business leaders.

He is also the founder of Martell Ventures, a portfolio of companies that makes over $100M in revenue.

After spending time in jail and rehab at the age of 17, Dan turned his life around.

He taught himself to code, founded and led 3 tech companies to exit, and has invested in over 60 startups.

Dan was named Forbes Top 10 Business People to Follow on Social Media and is a highly sought-after speaker, including events by Tony Robbins, John Maxwell, and other top leaders.

His content, keynotes, and coaching programs have helped thousands of clients unlock growth, get fit, and develop the mindset to become the best version of themselves.

In this interview, we discuss:

-How to implement the methodology of Buying Back Your Time

-How to structure our time to maximize our energy

-The most common pitfalls to watch out for when trying to maximize buying back your time

#100 Coach Jon Gruden: The Keys to Building a Championship Mindset

Coach Jon Gruden led the Tampa Bay Buccaneers to a Super Bowl victory in 2003. Previously, he was the head coach of the Oakland Raiders and had a second head coaching stint with them in 2018. He was also in media for 9 years where he hosted Monday Night Football and Gruden’s QB Camp on ESPN. Coach Gruden is one of the best offensive minds in the history of the NFL. Currently, he works for Barstool Sports and he has a YouTube channel called Gruden Loves Football where he previews games and interviews athletes and coaches.

In this interview we discuss:

-the traits of a Gruden Grinder

-his biggest influences as a coach

-what we can learn from Steve Young’s frustrations backing up Joe Montana

-why it’s important to be respected as a leader, instead of trying to be liked

-how to command attention

-advice to a first time leader

-how we can handle pressure better

-how to improve your self-awareness, and more..

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Check out Coach Gruden’s YouTube channel here

Follow me on LinkedIn

#99 Dwayne Cowan: Leading Your Career With Openness

Dwayne Cowan is the President of the Residential HVAC business at Trane Technologies. He earned his degree in biological engineering from the University of Georgia and his MBA from the Arizona State University. For nearly 20 years he's led teams in the HVAC industry both at Thermo King and now Trane -- which is widely known as the leader in the HVAC industry. In this episode we discuss:

-the importance of preparation 

-why the best leaders are inclusive

-why asking for help is a sign of courage

-why the best leaders usually don't have all the answers

-why you should lead with openness in your life and career and more..

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Follow Dwayne on LinkedIn

#98 Mark Matson: Redefining The American Dream

Mark Matson is a financial expert and investment advisor. As the founder and CEO of Matson Money, his firm has $8.6B in assets under management while serving 35,000 families nationwide. Mark published his book, Experiencing the American Dream: How to Invest Your Time, Energy, and Money to Create an Extraordinary Life. During our interview, we discuss:

-Why money can't buy happiness

-The misconceptions we've been taught about The American Dream

-How we can change our relationship with money and (and basic finance tips)

-How challenging experiences can build character

-Why sometimes your greatest strength can also be your weakness and much more..

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Check out Mark’s book here

#97 Richard Krulik: Viewing Problems as Opportunities

Richard Krulik is the CEO of Briggs & Riley, a well established luggage brand that has been in existence for over 30 years. Richard and I discuss the rich history including:

-how he onboards new employees to create a better culture at work

-why good companies are built on trust -how to prepare in advance of chaos, or as he says "fly the plane"

-how his father led by example

-what he hopes his team would say about him as a leader

-why it's important to view problems as opportunities

-how they demonstrate company values like "smart & steady"

-why it's important to travel for personal growth

#96: Tessa West: Finding Work That Works For You

Tessa West is a professor of psychology at NYU. She's the author of Jerks at Work and Job Therapy: Finding Work That Works For You. Tessa's TED Talk -- The Problem With Being "Too Nice" at Work has nearly 800,000 views. In Job Therapy she provides a science-backed handbook that will help you better understand your relationship with your job and how to improve it. She also discusses the most common reasons why people are frustrated in their careers and how to address them.

In this episode we discuss:

-debunking career advice myths

-how to balance emotion & logic when making career decisions

-the difference between the person who sends hundreds of resumes out with no plan vs the person who takes action

-the 5 sources of career frustration and more

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Follow Tessa on LinkedIn

Order her book, Job Therapy

Watch her TED Talk, The Problem With Being “Too Nice” At Work

Follow me on LinkedIn

#95 Kim Scott: How to Work Together Better

Kim Scott has worked in leadership roles at companies like Apple and Google. She is also a best-selling author as her book, Radical Candor, is one of the most beloved business books of the last decade. In Radical Respect: How to Work Together Better -- she details how organizations that optimize for collaboration and honor everyone's individuality are often more successful, joyful places to work.

In this episode we discuss:

-Why it's the leaders' responsibility to call out bias on a team

-The significance of fostering a respectful culture at work

-What we can all do to aspire to be better teammates (being an upstander)

-Book recommendations and more..

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Follow Kim on LinkedIn

Check out her website and books

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Follow me on LinkedIn

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Show Notes

00:00 Introduction and Guest Overview

01:33 Discussing Radical Candor

04:43 Feedback and Radical Respect

08:54 Challenges in Leadership and Management

13:13 Creating a Positive Work Environment

18:50 The Role of Managers and Leaders

22:56 The Importance of Feedback and Teaching

25:29 A Story of Bias and Leadership

30:29 Accountability and Respect in Leadership

30:39 The Impact of Language and Feedback

31:42 Understanding and Being an Upstander

31:58 Intervening as an Upstander

#94: Dan Harris: Taming the Voice In Your Head

Dan Harris was an award-winning ABC Journalist who anchored Nightline. He's widely known for having a panic attack on national TV. Through a lot of inner work, he published 10% Happier about his traumatic experience and how he was able to rehabilitate himself which included practices like meditation. Dan's TED Talk on self-compassion has eclipsed 3 million views. We discuss his work including:

-What he learned about himself through interviewing hundreds of people

-The inflection point that led to his 360 assessment to understand what people really think of him

-What he learned from his mentor, Peter Jennings

-What he recommends to try to strike balance in life

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Watch Dan’s TED Talk

Check out his meditation app

Order 10% Happier on Amazon

#93 Brianna Wiest: Defeating Self Sabotage

Brianna Wiest is the best-selling author of The Mountain Is You, 101 Essays That Will Change The Way You Think, and The Pivot Year. Her books have been read by millions of people and she is widely recognized for her wisdom of navigating life's challenges. In this episode we discuss The Mountain Is You including:

-the definition of self-sabotage

-the ways you can recognize self-sabotage

-how we can begin to course correct

-the significance of following your intuition or gut

-what she's learned about happiness and more..

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Check out Brianna’a website

Check out The Mountain Is You on Amazon

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SHOW NOTES

Understanding Self-Sabotage: An Interview with Brianna Wiest In this episode, we sit down with Brianna Wiest, best-selling author of 'The Mountain is You,' to discuss the concept of self-sabotage. Brianna shares her insights on how self-sabotage is the presence of two coexisting but conflicting needs, one often unconscious. She delves into her writing process, which deeply draws from her personal experiences, and explains how recognizing and addressing these inner conflicts can pave the way for personal growth. We also explore the importance of emotional intelligence, self-care, and the often misunderstood nature of happiness. Brianna provides profound advice on how to discern true instincts from comfort zone boundaries, making her wisdom invaluable for anyone looking to overcome self-defeating behaviors.

00:00 Introduction and Guest Overview

01:28 Brianna Wiest on Writing and Personal Experience

10:43 Understanding Self-Sabotage

20:41 Emotional Intelligence and Coping Mechanisms

25:46 The Importance of Authenticity

28:22 The Role of Instinct and Intuition

33:26 Living in the Present and Self-Care

40:10 Concluding Thoughts on Happiness

43:12 Final Reflections and Closing

#92 Scott Tannen: Disrupting the Status Quo to Make an Impact

Scott Tannen is the founder and CEO of a luxury linen and home goods company called Boll & Branch. They're best known for their luxury organic cotton bed sheets. Scott began his career working for established consumer packaged goods brands like Nabisco and Wrigley where he led digital marketing teams. He went to become the founder of Boll & Branch with the goal of bringing products to market that were sustainable for cotton farmers that eventually disrupted an industry. You'll enjoy this episode if you're curious about:

-How mentors can challenge you to level up your game

-How our parents can influence our life and career decisions

-Why it was important for Scott to invest 2 years figuring out how to make products in a sustainable way that was good for people and the environment

-How is $2 million bet with Howard Stern paid off

-Why you should never sacrifice things that are important to you that you'll regret for work (and how to do it) and more..

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SHOW NOTES

00:00 Introduction and Early Life

00:15 Parental Influence and Career Beginnings

02:17 Entrepreneurial Journey and Family Dynamics

02:50 Missy's Role and Women's Entrepreneurship

05:30 Lessons from Parents and Family Values

08:44 Leadership and Mentorship

21:16 Career Reflections and Early Successes

26:23 Founding Bol & Branch

40:01 Facing the Challenges of Self-Funding

40:41 Navigating Early Success and Scaling

43:50 Family Involvement in Business

45:48 Key Inflection Points and Business Lessons

49:15 Expanding Product Lines and Marketing Strategies

55:29 Leadership and Company Culture

01:00:44 Reflections on Sacrifice and Success

01:08:27 Advice for Aspiring Entrepreneurs

01:15:17 Conclusion and Final Thoughts

#91 Jacob Pechenik: Embracing the Beginner's Mindset

Jacob Pechenik is the co-founder and CEO of Lettuce Grow, a company that makes hydroponic, self-watering farm stands that help you grow your own fresh fruits and vegetables at home -- the way nature intended.

Jacob has sustained success in multiple industries and brings a unique perspective in terms of what habits and mindset has helped him over the years. In this episode we discuss the mission behind Lettuce Grow including:

-How he's been able to sustain excellence in multiple careers

-How in hindsight, his past expereince became the stepping stones for his most important work

-How to embrace the beginner's mindset, and more..

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Check out Lettuce Grow here

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This episode is brought to you by AquaLiv, in my opinion the best water filter system that is the best tasting water that is also healthy and alkaline. You can learn more about AquaLiv here.

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Subscribe on: iTunes | Sticher | Overcast | Google

#90 Ryan Hawk & Brook Cupps: Excellence Over Success

Ryan Hawk is the host of The Learning Leader Show, 3x author, and a keynote speaker. Brook Cupps is the head basketball coach at Centerville High School in Ohio where they’re state champions. They’ve co-authored The Score That Matters: Growing Excellence in Yourself and Those You Lead/

In this episode we discuss:

-Developing core values and how to emulate them

-Why it’s important to identify the most dependable people in your personal and professional life (foxhole friends)

-Why it’s important to do the extra work, and more..

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Check out The Score That Matters on Amazon

#89 James Clear: Making Habits Stick & Breaking Bad Ones

James Clear is a habit formation expert. His book, Atomic Habits, has sold over 20 million copies. He ships a weekly newsletter to 3 million subscribers. His new app, Atoms, is the digital extension of his book to help people make their habits stick.

In this episode we discuss:

-The difference between someone who can lose 180 lbs doing P90X compared to the one who won't make a change

-The deepest level of behavior change, identity-based goals, and how to achieve them and stay on track

-How to break bad habits, and more..

Watch the interview with James here:

#88 Michael Lombardi: How History Shapes Our Future

Michael Lombardi is one of the leading experts analyzing the game of football. He currently hosts The GM Shuffle and recently published his second book, Football Done Right, which pays homage to the history of the NFL including great players and coaches. He’s the former General Manager of the Raiders and Patriots, and he worked as a scout under the legendary Bill Walsh with the San Francisco 49ers in the mid 1980s.

In this episode we discuss:

-The impact of Monday Night Football on pop culture

-How he got his break an UNLV

-The impact Bill Walsh had on him as a lifelong learner

-Reflecting on good and bad draft picks

-Advice to his sons on how to be the best coaches and more..

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Check out Robert’s podcast, RG3 & The Ones

Follow him on Twitter

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This episode is brought to you by Atla water system, in my opinion the best tasting water that is also healthy and alkaline. You can learn more about Atla here.

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Subscribe on: iTunes | Sticher | Overcast | Google

#87 Robert Griffin III: Betting On Yourself

Robert Griffin III is a Heisman Trophy winner, Pro Bowler, and NFL Rookie of the Year. He's currently an ESPN analyst and hosts the podcast, RG3 & The Ones. In this episode we discuss:

-Why he wanted to emulate Michael Jordan

-The criteria he used to select Baylor University after receiving 25 scholarships

-Receiving recognition vs the joy of developing others

-Traits of the best bosses and leaders

-How he responded in the face of adversity, and more..

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Check out Robert’s podcast, RG3 & The Ones

Follow him on Twitter

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This episode is brought to you by Atla water system, in my opinion the best tasting water that is also healthy and alkaline. You can learn more about Atla here.

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Subscribe on: iTunes | Sticher | Overcast | Google

#86 Ali Abdaal: How to Defeat Procrastination

Ali Abdaal is a productivity expert who teaches through his YouTube channel, podcast, and book titled Feel Good Productivity. His superpower is making learning fun.

In this episode we discuss:

-How he decided to make the career switch from medicine to a full-time YouTuber.

-The importance of the beginners mindset

-How asking for help can actually strengthen your relationships

-Getting more clarity around your goals

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Check out Ali’s YouTube channel

Order Feel Good Productivity

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This episode is brought to you by Atla water system, in my opinion the best tasting water that is also healthy and alkaline. You can learn more about Atla here.

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Subscribe on: iTunes | Sticher | Overcast | Google