Travis Makes Money

In this episode, Travis and producer Eric react to a viral video from Vivian Tu (“Your Rich BFF”) breaking down three popular “get rich quick” strategies that actually cost most people money: whole life insurance as an investment, day trading, and “passive” side hustles like wholesale real estate, Amazon dropshipping, and affiliate marketing. They use the clip as a springboard to talk about discipline, risk, and why most people should stick to simple, boring money moves instead of gambling their future on complex schemes they barely understand.​

Top 3 Takeaways

For most people, the simplest play—buy term life insurance for protection and invest consistently in diversified, long-term stock market holdings—beats complicated insurance and trading schemes.

Day trading is statistically stacked against you; unless you treat it like gambling with true “play money,” your odds of long-term success are far worse than just buying and holding quality assets.

“Passive income” buzzwords around real estate, dropshipping, and affiliate marketing hide the reality that these are real businesses requiring time, effort, and often capital—especially when you’re just getting started.

Notable Quotes

"If you’re just starting out, whole life and infinite banking shouldn’t even be on your radar—it’s a distraction sold hard because the commissions are huge."

"Don’t pretend you’re an expert trader when even the best hedge fund managers in the world tell you not to time the market."

"People keep looking at these advanced strategies as the thing that’ll make them rich, instead of realizing they only really make sense once you’re already rich."​

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Rachel Zaslansky Sheer and Lori Zuker Briller are the co-founders of The Grapevine, a premier corporate and domestic staffing firm known for placing top-tier talent with high-profile executives, households, and leading companies. With 20+ years of recruiting experience across entertainment, tech, finance, real estate, fashion, and more, they’ve built a referral-driven “job matchmaking” agency and recently coauthored “Straight From the Grapevine: How to Crush Your Job Search,” a practical guide to modern career strategy and job hunting. Their backgrounds as former entertainment assistants and development executives give them a rare, inside-out view of both sides of the hiring table—what makes candidates stand out and what employers actually need.​

Top 3 Takeaways

Early, “small” jobs matter: they build work ethic, professionalism, and people skills that compound into better opportunities, references, and confidence later in your career.

Great candidates treat every role like it matters—showing up with excellence, initiative, and a good attitude—because that’s how you get noticed, recruited, and referred into the dream jobs you actually want.

In today’s noisy job market, understanding how recruiting really works, presenting a sharp résumé, and mastering basic etiquette (clear emails, context, professionalism) are major unfair advantages.

Connect with Rachel & Lori (The Grapevine):

​https://www.thegrapevineagency.com/

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In this episode, Travis and producer Eric dive into breaking sports media news: ESPN and Penn Entertainment unwinding their $2 billion, 10-year ESPN Bet partnership just two years after launch and pivoting into a new multi-year deal with DraftKings. They unpack what this says about ESPN’s fading dominance, DraftKings’ position as the default sportsbook brand, and how Barstool founder Dave Portnoy continues to land on his feet after Penn sold Barstool back to him and rebranded to ESPN Bet. Along the way, they draw parallels to Disney’s evolving “family-friendly” branding strategy, the broader shift from legacy TV to social-first sports media, and why product quality and user behavior matter more than just a big name.​​

On this episode we talk about:

The stunning early termination of the ESPN–Penn Entertainment $2B, 10-year ESPN Bet deal, effective December 1, 2025, after ESPN Bet failed to crack meaningful market share.​

Why ESPN Bet reportedly struggled to get above ~5% market share and never hit “top three” sportsbook status despite ESPN’s massive brand and distribution.​

Penn’s prior Barstool Sports era, regulatory pushback tied to Portnoy’s persona, and how Penn sold Barstool back to Dave Portnoy as it pivoted to the ESPN Bet rebrand.​​

Portnoy’s reaction on his own show, why he thinks time will tell if this is a good move for DraftKings, and his hint that Disney CEO Bob Iger made unflattering comments about Barstool behind the scenes.​

How Disney’s move from “no R-rated content” on Disney+ to hosting edgier, R-rated films via the Hulu integration shows a slow but real shift away from a strictly squeaky-clean image.​

Why even a giant like ESPN can’t just slap its logo on a product and win—especially when users already love DraftKings and other established betting apps.​

The rise of social-native sports brands like House of Highlights and Barstool Sports, and how short-form content has replaced traditional SportsCenter viewing for many fans.​​

Jake Paul’s “Betr” (Better) and other creator-led betting and media plays, and how having the ear of younger fans changes the balance of power in sports media.​

Why product quality, UX, and habit lock-in often beat legacy branding, even when legacy outlets still dominate live rights and TV distribution.​

A quick detour into the best sports movies of all time—Hoosiers, Remember the Titans, Warrior, Rocky, Moneyball, and more—and what they reveal about the nostalgia we still attach to sports storytelling.

Top 3 Takeaways

Big legacy brands like ESPN and Disney can no longer rely on their name alone; in crowded categories like sports betting, sticky products and fan-favorite platforms like DraftKings are extremely hard to displace.​

Controversial personalities like Dave Portnoy can create regulatory and brand headaches, but they also build cult followings and resilient IP—Barstool’s rebound and Portnoy’s “$1 buyback” remain a masterclass in leverage.​​

The future of sports attention is social-first and creator-driven: fans increasingly get their highlights, hot takes, and sometimes even betting cues from digital-native brands rather than traditional TV networks.​​

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Rod Khleif is a Dutch immigrant, multifamily investor, and high-performance mentor who has owned over 2,000 single-family homes and thousands of apartment units across the U.S. He hosts “Lifetime Cash Flow Through Real Estate Investing,” one of the largest commercial real estate podcasts, where he teaches investors how to use multifamily, senior housing, and other commercial assets to create long-term wealth. After watching his net worth jump $17 million in 2006 and then losing roughly $50 million in the 2008–09 crash, Rod rebuilt by focusing on mindset, goal setting, and identity work—turning that “seminar” into a blueprint he now shares with students worldwide.​

On this episode we talk about:

Rod’s journey from broke Dutch immigrant kid in Denver to watching his mom buy a $30,000 rental that appreciated $20,000 and realizing real estate could change his life.

Getting his broker’s license at 18, struggling for two years, then jumping to over $100k in income after discovering the power of mindset, psychology, and the right mentor.

Building a massive portfolio of single-family and multifamily properties, seeing his net worth rise by $17 million in one year, and then losing around $50 million in the 2008 crash.

How Rod reframed that loss as a “$50 million seminar,” refused to let real estate become his identity, and used aggressive goal setting and identity statements to rebuild.

The current state of commercial real estate, including distressed multifamily deals due to interest rate shocks, emerging opportunity in senior housing/assisted living, and why he’s cautious on office but bullish on other asset classes.

Top 3 Takeaways

Your business is just a vehicle—if it fails, you are not a failure; separating identity from outcomes is essential if you want to recover from big losses and take bigger swings.

Clear, emotionally charged goals combined with “I am” identity statements and massive action create the momentum needed to push through fear, limiting beliefs, and comfort zones.

Right now is a rare window for prepared buyers in commercial real estate and small business acquisitions, with distressed multifamily assets and retiring Baby Boomer owners creating outsized opportunities.

Notable Quotes

"They’re only failures if you don’t get back up—otherwise they’re just very expensive seminars."

"Anything you put the words ‘I am’ in front of becomes an identity statement, and your life will rise or fall to match it."

"Don’t fear failure; fear regret—because not living the life you’re capable of is the real nightmare."

Connect with Rod Khleif:

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In this episode, Travis Chappell dives into the mindset shifts that separate effective salespeople from those who plead for clients’ attention. With a focus on the photography industry as a case study, he breaks down common mistakes creatives make when marketing their services and shares actionable strategies to connect authentically with clients.

On this episode we talk about:

The difference between pitching yourself and pleading for validation in business

How creative entrepreneurs often overemphasize their personal passion in marketing

Techniques to discover what clients truly want through effective questioning

Why building trust can sometimes mean turning away business

Applying sales lessons from photography to any industry

Top 3 Takeaways

Stop making your marketing about how much you love what you do—focus on the value you provide to clients.

Ask questions first to uncover client pain points, then tailor your pitch to solve their specific problems.

Building trust may require walking away from business that isn’t a fit, which can lead to stronger opportunities later.

Notable Quotes

"At a certain point, it shifts from 'I love what I do' to 'hire me so I’ll feel fulfilled,' and it can easily turn into ‘pick me.’"

"Your craft speaks for itself—focus your conversations on the client’s experience, not your personal fulfillment."

"If you can better explain somebody’s problem to them than they can, they’ll automatically assume you have the solution."

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With over two decades of real estate, sales, and professional coaching experience, Jeremy Herider's mission is to assist agents in building careers worth having, businesses worth owning and lives worth living.

https://harvist.com/

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In this candid and relatable episode, Travis and his producer Eric share personal experiences about starting in podcasting and content creation while grappling with imposter syndrome. They discuss how it's okay not to be an expert at first and how interviewing others can be a powerful way to create valuable content. Travis reflects on his own journey starting solo and the benefits of learning from others. They explore how comparison can either motivate or hold you back and emphasize the importance of embracing the learning curve, persisting through early struggles, and getting addicted to progress rather than perfection.

On this episode we talk about:

The challenges of feeling qualified to share your perspective early in content creation.​

How podcasting allows you to start by interviewing experts and grow your voice over time.​

The difference between writing a book and creating content in terms of commitment and flexibility.​

The dangers of comparison and how to use it as inspiration rather than a source of discouragement.​

The value of embracing imperfection and expecting to "suck" initially as part of mastery.​

Mentality shifts to get addicted to progress, even the small wins, in any skill-building journey.​

Top 3 Takeaways

1.  You don’t need to be an expert to start creating meaningful content—just start somewhere.​
2.  Interviewing and sharing others’ expertise can provide immediate value to your audience.​
3.  Expect initial failures and imperfections as a natural and necessary part of growth.​

Notable Quotes

  "Just start putting stuff out there—you’ll learn quickly what holds water and what doesn’t."​

  "Comparison should kick you forward, not kick you down."​

  "If you don’t suck at the start, you should have started years ago."​

Connect with Travis Makes Money:

  Website: travischappell.com​

  Instagram: @travischappell​

  YouTube: Travis Makes Money​

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JT Mestdagh shares his extraordinary journey of resilience overcoming multiple complex medical challenges from birth and severe dyslexia to becoming an adventurer and inspirational author. His book No Bad Days: Turning Your Biggest Challenges into Your Greatest Opportunities encourages young adults and everyone to view obstacles as opportunities for growth and to live a positive, purpose-driven life. JT also founded a charity supporting children with medical needs and literacy programs, intertwining his passion for adventure with giving back.

On this episode we talk about:

JT’s lifetime medical battles with VACTERL syndrome and how he manages daily bowel care through innovative surgeries.​​

The emotional and educational struggles with severe dyslexia and how finding the right learning program was life-changing.​​

How JT’s positive mindset, faith, and support from his tribe fueled his drive to climb Kilimanjaro, race the Grand Canyon, and start charitable work.​

The creation of his motivational book No Bad Days as an encouragement for youth and others facing adversity.​

JT’s foundation’s mission to supply medical and educational resources to children with similar needs.​

The importance of community, sharing one’s story, and finding joy and purpose despite hardships.​

Top 3 Takeaways

1.  Positivity and faith are powerful tools in transforming hardship into opportunity.​​
2.  Finding and nurturing a supportive tribe is crucial for motivation and growth.​
3.  Sharing personal stories inspires connection and helps others overcome their challenges.​

Notable Quotes

  "There are no bad days, only hard days that we get through together."​

  "Your story shapes you daily and can be used to support and uplift others."​

  "Every day is a blessing to keep going, to keep sharing smiles and joy."​

Connect with JT Mestdagh:

  Website: nobaddaysbook.com​

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In this episode, Travis and his producer Eric delve into how Gen Z approaches financial advice, heavily relying on social media platforms for guidance. They discuss the impact of the lack of traditional financial education, how social media has democratized access to financial info, and the risks and benefits of following influencers online. The episode highlights generational differences in financial behavior, trust in advice sources, and the crucial role of critical thinking in navigating abundant but sometimes misleading digital financial content.

On this episode we talk about:

Gen Z’s preference for social media as a source of financial advice over traditional education.​

The top platforms Gen Z uses for finance info: YouTube, Instagram, TikTok, X (Twitter), and Facebook.​

Most searched personal finance topics by Gen Z: budgeting, taxes, credit card debt, wealth building, and student loans.​

The prevalence of financial scams on social media and how it affects young people’s trust.​

The importance of discerning credible advice from marketing and misinformation.​

Generational differences in financial interests and skepticism, especially regarding crypto and MLMs.​

Why building trust through consistent, unbiased financial content is crucial for long-term influence.​

Top trusted sources for financial advice: parents/family, financial institutions, and friends.​

Top 3 Takeaways

1.  Social media is a dominant channel for Gen Z’s financial education but requires strong critical thinking skills due to misinformation risk.​
2.  Budgeting and credit card debt are central concerns for young people starting their financial journeys.​
3.  Trusted advice still comes mainly from family and well-established financial institutions, highlighting the ongoing role of personal relationships.​

Notable Quotes

  "77% of Gen Z actively seek financial advice on social media, but a quarter have been scammed there."​

  "Social media advice can be positive if you know how to sift through noise and marketing gimmicks."​

  "Trust comes from giving consistent value without direct financial incentives."​

Connect with Travis Makes Money:

  Website: travischappell.com​

  Instagram: @travischappell​

  YouTube: Travis Makes Money​

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🚀 Travis Makes Money is made possible by High Level – the All-In-One Sales & Marketing Platform built for agencies, by an agency.

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Brandon Steiner, known as the king of sports memorabilia, shares his journey from a sports-crazed Brooklyn kid with $4,000 to a transformative figure in sports marketing. As founder and president of Collectible Exchange and Steiner Sports, Brandon discusses how he revolutionized the memorabilia industry and built a $50 million empire with exclusive partnerships with legendary athletes like Derek Jeter, Mariano Rivera, and Muhammad Ali. He reflects on the fundamentals of business, the importance of delivering value, and the power of genuine relationships in building a successful sports marketing business.

On this episode we talk about:

Brandon’s early entrepreneurial experience and lessons from working at top companies before starting his own business.​

The creation and growth of Steiner Sports, focusing on fundamentals, customer value, and brand loyalty.​

The process of building relationships with influential clients based on giving value first and expecting nothing in return.​

The founding of Collectible Exchange to help collectors manage and sell their memorabilia efficiently.​

Advice for young entrepreneurs on fundamentals, resilience, and maintaining authenticity in business.​

The critical role of enthusiasm and faith in persevering through challenges and competition.​

Top 3 Takeaways

1.  Strong foundational business principles and fundamentals are key to long-term success.​
2.  Building authentic, value-driven relationships fosters sustainable business growth.​
3.  Passion combined with strategic giving and resilience creates lasting influence and opportunity.​

Notable Quotes

  "Making money is easy; staying authentic and keeping your brand on track is the hard part."​

  "Put yourself in the customer’s shoes to understand what they really need."​

  "Do as much as you can for as many people as you can, as often as you can, and expect nothing back."​

Connect with Brandon Steiner:

  Website and Books: brandonsteiner.com​

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🚀 Travis Makes Money is made possible by High Level – the All-In-One Sales & Marketing Platform built for agencies, by an agency.

🚀 Capture leads, nurture them, and close more deals—all from one powerful platform.

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