Rebecca Matchett is a serial entrepreneur, fashion innovator, and now tech founder who’s built her career around solving real-world problems. From co-founding Alice + Olivia to developing a patented women’s sizing system called TrioFit, Rebecca has consistently combined creativity and practicality to build impactful businesses. Now, she’s channeling that same drive into Synchrony—a new social app designed to help neurodivergent adults connect and combat loneliness in meaningful ways.

On this episode we talk about:

How Rebecca transitioned from fashion and retail into tech entrepreneurship

The story behind founding Alice + Olivia and what she learned about branding and innovation

Why ideas alone aren’t enough—and how to validate your market before launching

The challenges and benefits of self-funding vs. outside investment

How Synchrony is using technology to address the loneliness epidemic among neurodivergent adults

Top 3 Takeaways

Great businesses start by solving problems you truly understand—personal experience is a powerful indicator of market need.

Validation matters more than inspiration. Don’t build before you know who actually wants your product.

Bootstrapping gives you control, focus, and creative freedom that investors often limit.

Notable Quotes

“Ideas are easy. Execution and validation are what separate entrepreneurs from dreamers.”

“When you solve a problem for yourself, you’re often solving it for thousands of others.”

“Connection is the most human need we have—and we’re building a tool to make that accessible again.”

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Jen Powell is the innovative CEO of JP Inc, a talent management agency revolutionizing influencer licensing with offices in LA, Nashville, and New York. With over 20 years of experience in modeling and influencer marketing, Jen has transformed the traditional fashion industry by embracing influencer-driven commerce early on, making her a unique leader in this space.

On this episode we talk about:

Jen’s transition from a top modeling agent to a pioneer in influencer marketing

Early success stories of monetizing fashion blogs through sponsorships

The challenges and opportunities within traditional modeling agencies

Founding JP Inc and growing it into a national influencer talent agency

The future of modeling, including digital/AI models and the enduring need for human connection

Creator brand development and licensing as a low-risk business strategy

Details about Jen’s course, "The Creator’s Path to Product"

Top 3 Takeaways

Social media followership is now a critical factor in hiring talent within the modeling and influencer industries.

Licensing allows creators to retain ownership of their intellectual property while scaling their brands with less risk.

Despite advances in digital and AI models, authentic human connection remains vital in storytelling and marketing.

Notable Quotes

"If there’s two models up for a job and one has 3 million followers and one has 5,000, the model with 3 million followers is going to get the job."

"It’s better to make everybody think you’re dumb than to speak up and remove all doubt."

"Human connection matters more than people think it does in modeling and storytelling."

"Licensing your creator business offers a less risky path while you build your brand and audience."

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Tim Elmore is the founder of Growing Leaders, a nonprofit dedicated to developing emerging leaders, with over 20 years of experience working alongside leadership expert John C. Maxwell. He is a prolific author of 40 books on leadership, including his latest, The Future Begins with Z, which explores innovative strategies for leading Generation Z as they disrupt the modern workplace. Tim’s insights into generational differences, leadership challenges, and entrepreneurship make him a valuable voice for anyone navigating today’s rapidly changing workforce.

On this episode we talk about:

The unique characteristics of Generation Z compared to Millennials

How Gen Z’s relationship with technology and social media influences work habits

The rise of micro-entrepreneurship among young people and economic shifts

Leadership strategies for coaching and connecting with Gen Z rather than commanding

The changing nature of work ethic and purpose across generations

Top 3 Takeaways

Connection and coaching are more effective than authority when leading Gen Z.

Gen Z values purpose and flexibility in work, often seeing jobs more like hobbies.

Micro-entrepreneurship is growing rapidly as many young people seek autonomy and reject traditional corporate models.

Notable Quotes

"Generation Z is the sandpaper on my leadership. I did not know I needed. We become better leaders because of them."

"Your connection gives you the right to influence, not your position."

"We’ve got to lead from bridges we build, not badges we wear."

Connect with Tim Elmore:

LinkedIn: Tim Elmore LinkedIn

Twitter/X: @TimElmore

Instagram: @timelmore

Website: timelmore.com

Growing Leaders nonprofit: growingleaders.com

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This episode features a candid conversation between Travis and his producer Eric, diving into the ways that religious backgrounds shape money mindsets and personal finance decisions. Travis reflects on his own experiences growing up in a large, well-resourced church and how both healthy principles and harmful attitudes have impacted his financial outlook over time. Through personal stories and playful banter, Eric and Travis explore the tension between gratitude, ambition, and the reality of pursuing financial stability.

On this episode we talk about:

Money lessons learned in church environments

How religious upbringing impacts beliefs about wealth

Church paradoxes regarding money and religious leaders

Harmful vs. helpful financial mindsets from faith backgrounds

Advice Travis would give his younger self about money

Top 3 Takeaways

Your spending reveals what truly matters to you—track where your money goes to understand your priorities and values.

Religious environments often transmit complex and conflicting attitudes about money, sometimes discouraging the active pursuit of wealth while still praising and seeking it when helpful to institutional needs.

The pursuit of money itself is not inherently wrong; examine your beliefs and recognize that financial empowerment offers options and flexibility that can benefit both you and your family.

Notable Quotes

"Where your money is, that's where your heart is. You can examine your expenses to quickly see your true priorities."

"Churches talk about money as if it's evil, but they also highly value it when it serves their purposes—that dissonance can mess with your mindset."

"Money is an amplifier of who you are. It by itself is not intrinsically good nor bad. Choose to see it as a tool for good and an option creator."

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Emma Rainville is a fractional CEO and operations strategist with over a decade of experience transforming seven, eight, and nine-figure businesses behind the scenes. Known as the "integrator by DNA," she specializes in moving founders from burnout and cash bleed to scalable, profitable growth. Emma’s reputation rests on her blunt, practical approach and her obsession with execution—not just theory—and on her proven ability to architect systems that protect profits and foster company culture. With her trademark SCOPE model and Wave Vision process, Emma helps businesses create sustainable systems that unlock new levels of efficiency and profit.

On this episode we talk about:

Emma’s first entrepreneurial hustle at age eight and early lessons in leverage

The hidden pitfalls founders face with unchecked expenses and chaotic systems

Why most business owners fail to understand their true numbers—and how to fix it

The critical role of SOPs: why written processes and automation trump hiring

How AI and automation are disrupting labor-intensive businesses, from landscaping to admin work

Emma’s journey through the IDF, ER trauma nursing, and operations leadership—plus the real secret behind her career pivot

Highest-leverage automation opportunities business owners miss

The key mindsets and habits of growth-focused founders

Top 3 Takeaways

Unchecked expenses silently destroy profit—regular, ruthless review of every expense can unlock 3-4% profit instantly.

Most business owners don’t know actual unit-level profitability; tracking this granular data enables better decisions, higher margins, and less work.

Strong businesses scale with written SOPs and automation, not by hiring; processes should come before people.

Notable Quotes

“Sales is king.”

“Every dollar needs to have a name, and every person should know the numbers that matter.”

“You can’t automate chaos—get your processes right, then use AI and automation to scale.”

Connect with Emma Rainville:

https://www.instagram.com/emma_rainville512/?hl=en

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Rob Dyrdek, entrepreneur, producer, and former pro skateboarder, is best known for creating and hosting "Ridiculousness," the viral video clip show that dominated MTV from 2011 to 2025. His relentless work ethic, innovative approach to the clip show format, and deep understanding of changing TV and streaming habits helped drive the show to unprecedented success, spanning 46 seasons and over 1,700 episodes. Dyrdek’s business savvy made him not only a staple on TV but also one of the most well-compensated talents on the network, earning over $32 million a year in recent seasons. In this episode, Travis and Eric break down the recent news that "Ridiculousness" has been canceled after 14 years, explore the show’s legacy, and share Dyrdek’s insights from his past interview about content creation, business strategy, and media evolution.​

On this episode we talk about:

The unprecedented cancellation of Ridiculousness after 46 seasons on MTV

Why the show’s viral format succeeded across all demographics and became a TV staple

Rob Dyrdek’s strategy for negotiating big business deals and content syndication

The future of MTV and potential impacts of the Paramount merger on creative programming

How Dyrdek adapted to shifts from traditional television to streaming and social media

Top 3 Takeaways

The relentless volume and fast-paced format of Ridiculousness helped the show thrive even as cable viewership habits changed and streaming dominated.​

Rob Dyrdek’s approach to building, negotiating, and owning production allowed him to capitalize on market timing, adapt to new trends, and maximize personal earnings.​

MTV’s shift towards curated, experimental content signals a major change in the network’s strategy, reflecting broader media trends and the challenges of legacy cable brands competing in the streaming era.​

Notable Quotes

"There’s a lot of miraculous things that sort of happened over time that led to [Ridiculousness dominating MTV]." – Rob Dyrdek

"You’re the right man, right vision, legs – and created something and then made it work. But then you got lucky along the way, and market factors that you could have never even seen coming." – Rob Dyrdek

"Market factors, market timing, getting lucky and things working at the right time is where a lot of this really unexplainable high level of success comes from." – Rob Dyrdek

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Welcome to a grab bag episode of the Travis Makes Money podcast, where Travis and producer Eric riff on the reality behind success—highlighting why business is the great equalizer for anyone willing to put in the work. Rather than featuring a singular guest, this episode is a candid discussion between Travis and Eric, full of humor, pop culture, and philosophical digs about work ethic, optionality, the nature of talent, and actionable (if often ignored) business wisdom. They use standup comedy and pop references as a lens on entitlement, the “special snowflake” myth, and the sometimes mind-numbing monotony behind real progress.

On this episode we talk about:

Why most people settle for being a cog and what it actually takes to “opt out”

Daniel Tosh’s take on employment, entitlement, and the myth of guaranteed fame

The difference between success in business versus creative arts: luck, timing, and talent

Why simple, repetitive business actions (doing the boring work) are the true formula for income

The reason people mock Gary Vee’s advice, but why doing the basics still actually works

Top 3 Takeaways

Most people are held back not by talent or opportunity, but by their own acceptance of mediocrity and avoidance of repetitive, boring work that creates options and freedom.

Business is fundamentally a learnable, math-like skill: boring, repeatable actions generate income better than “waiting for your shot.”

Freedom requires you to learn how to make money outside of a paycheck—otherwise, you’ll always be forced to trade your time for someone else’s goals.

Notable Quotes

"The barrier to entry isn’t talent; it’s being willing to do the boring, repetitive work that most people constantly avoid."

"For creative fields like acting or music, sometimes world-class talent never gets a shot—business isn’t a zero-sum game that way."

"You have to put yourself in a position to have options. Staying broke is another way of saying you decided to let someone else define your ceiling."

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On this episode of the Travis Makes Money podcast, Travis and producer Eric jump into a mix of thoughtful, funny, and heartwarming clips, landing on a story about comedian Chris DeStefano and the challenge of choosing between earning more money and spending time with family. Chris discusses turning down work to prioritize his kids, sparking a candid conversation about career, sacrifice, and what success truly means at different life stages.

On this episode we talk about:

Why Chris DeStefano values family moments over chasing every dollar​

How personal circumstances and seasons of life dictate work/family choices​

Navigating parenting, money, and the tradeoffs of financial hustle​

Lessons from upbringings and parental examples, and their impact on work ethic​

Building a life that aligns with personal priorities, not just chasing excess​

Top 3 Takeaways

You don’t need all the money—knowing when “enough” is enough lets you choose family and peace over constant hustle​

Life happens in seasons—sometimes you must work extra, but intentional planning lets you cherish key family moments​

Children learn most by watching you; modeling responsible hustle and thoughtful sacrifice is as impactful as time spent​

Notable Quotes

“I just feel like I don’t need all of it. I just need enough for me … I don’t want to miss my kids’ lives.”​

“Kids don’t need you there 24/7—they need you present for the moments that matter.”​

“Doing nothing is not the solution. Doing something is, and doing something in volume is even better.”​

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Travis is joined by producer Eric for a wide-ranging, deeply philosophical episode exploring how beliefs, meaning, and personal philosophy influence the way money, work, and life are experienced. Both hosts share their takes on existential questions (with spontaneous detours into Star Trek, simulation theory, and work ethic), showing how practical mindset shifts are inseparable from financial success.

On this episode we talk about:

Various mental models that shape work, motivation, and the experience of meaning

How philosophy—like Nietzsche’s ‘eternal recurrence’—reframes choices and ambitions

The importance of recognizing meaning as self-generated, not assigned by circumstance or others

Why evaluating beliefs by their practical usefulness is a key discipline in modern business

How accepting truth wherever you find it drives personal growth, resilience, and sharper decisions

Top 3 Takeaways

Philosophy matters: Questioning and reframing beliefs about meaning and agency lead directly to greater productivity and financial outcomes.

Meaning is self-generated—thinking carefully about what keeps you going can reveal your true priorities and help you make better life and money choices.

Adopt beliefs and mindsets that are useful for your growth—even if you can’t prove them, lean into what propels you forward and out of ruts.

Notable Quotes

“Meaning is entirely self-generated. You decide, and it might change over time. So choose wisely.”

“If a belief system isn’t useful—if it doesn’t propel you into meaningful action—why keep it?”

“Accept truth wherever you find it, regardless of who says it. That’s how growth happens.”

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On this episode, Travis and producer Eric break down why building a career or business in 2025 means leveraging the power of content and relationships on social media. Drawing inspiration from powerhouse voices like Gary Vee, they explore the real tactics, mindset shifts, and simple habits that separate those who get results from those who just “post and ghost.”

On this episode we talk about:

Why creating content is no longer optional for business owners and sales pros

The biggest mistakes new (and seasoned) agents make on social—and how to fix them

Why “posting” alone isn’t enough (and why engaging with others matters more)

How to start from scratch: practical tips for getting over perfectionism and fear

The right approach to building habits, including using accountability tricks and “just doing the thing”

Top 3 Takeaways

Social media attention is a massive business opportunity, but most people overthink and underact—just post, learn, and iterate in public.

Engagement—commenting, DMs, reacting, and showing up in conversations—is what unlocks genuine relationships and leads. Stop screaming at the crowd; start talking to them.

Consistency and volume win. Your first attempts might suck, but nobody wins without building the habit of simply creating and sharing.

Notable Quotes

“The number one thing that will change every person in this room’s life financially is making content for social media.”

“Doing nothing is not the solution. Doing something is the solution. And doing something in volume is even better.”

“Social isn’t a bullhorn—it’s a cocktail party. If you’re not actively engaging, you’re just the weird guy yelling at everyone."

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