Travis Makes Money

Travis's holiday-themed ad segues and his trick for tying sponsor reads into episode content

The Andy Cohen babysitting backlash and whether $30 an hour for two kids is cheap

Typical babysitting rates in Los Angeles ($23–$35 an hour, per child) and the "celebrity tax"

Why Travis thinks a deal both sides agreed to isn't anyone else's business

The Reddit post about a 15-year-old volunteered to babysit seven kids for free, and how the family should have handled it

Know the market rate before you hire or set a price. Babysitting in LA often runs $23–$35 an hour per child, so pricing for multiple kids should reflect the extra work.

Never commit someone else's time or labor without asking them and agreeing on pay up front, even when it's family.

If both sides agree to a fair deal, it's their deal. But if you have the means, paying a little extra (or covering the cost yourself to avoid conflict) builds goodwill.

"If the deal was made and both parties are happy with it, then why is everybody else freaking out about it?" – Travis

"That's crazy to expect a 15 year old to just watch seven kids for free while you all go drink." – Eric

"Worst case scenario, if I'm the husband and I just don't want to deal with the family drama, I'm paying my daughter." – Travis

Instagram: @travischappell

Other: travischappell.com

How Peter acquired Elfster's first 1,000 users through personal networks, online communities, and early Google advertising.

Why solving a clear problem with a fun, shareable product can drive sustainable, organic growth.

How Elfster manages seasonal revenue, controls expenses, and continues growing beyond the holiday season.

Turning a gift exchange platform into a social commerce business with hundreds of retail partners and millions of users influencing gift trends.

Why Peter wants to keep Elfster independent and build a company that can thrive long after he's gone.

Solve a real problem and make it easy to share. Elfster started by addressing a simple frustration: organizing Secret Santa exchanges across families and friend groups. A useful, fun product gave people a reason to invite others, helping the platform grow organically.

Build for sustainable growth, not just rapid expansion. Peter grew Elfster over two decades without outside funding. Retaining users, leveraging word of mouth, investing in relevant marketing, and carefully managing expenses helped the company navigate seasonal revenue and economic uncertainty.

Think beyond yourself when building a business. Peter's goal isn't to sell Elfster to the highest bidder. He wants to preserve its independence and create a company that continues serving customers for generations. Building a lasting business means thinking about its future beyond your own involvement.

“Every year it's like a snowball effect.”

“You can't entertain people until they're there.”

“I'd love it to be a company that lives to a hundred years.”

Website: Visit travischappell.com/elfster, use code "TRAVIS" to get started with your own gift exchange

Instagram: @elfster

Apps: Search for Elfster in the iOS App Store or Google Play Store.

Why Airbnb’s new cleaning policy has sparked backlash from hosts and how customers are responding

Why running a small business means solving problems for customers instead of making excuses

How excessive fees and checkout chores can push travelers back toward traditional hotels

Why customer feedback and market demand should influence how businesses operate

How unique, thoughtfully designed Airbnb properties can offer experiences hotels struggle to replicate

Your customers decide whether your business deserves to survive. If customers consistently complain about the experience, listen to their feedback and make improvements instead of defending the status quo.

Running a business means taking responsibility for the customer experience. Airbnb hosts choose to operate in hospitality, which means providing a clean, reasonably priced place to stay—not expecting paying guests to compensate for operational shortcomings.

Differentiation is more powerful than cutting corners. Airbnb hosts can compete with hotels by offering distinctive properties, creative themes, and memorable experiences. Making the experience better gives customers a reason to book again.

“One of the core aspects of running a business is surveying customers, is asking customers questions, is learning, is getting feedback from their experience.”

“You can't expect the market to bend around the needs of your business.”

“Focus on making a better experience if you want to maintain high demand in bookings.”

Instagram: https://www.instagram.com/travischappell/

Website: travischappell.com

How Waldo transitioned from being a combat-decorated fighter pilot to a career in sales, speaking, and entrepreneurship.

Why preparation, work ethic, and resilience are essential to succeeding in sales and business.

How building relationships, asking for help, and paying it forward contributed to Waldo's professional growth.

Why building a personal brand and platform before publishing a book can make it easier to generate sales and open doors.

How commitment, purpose, and teamwork can help you overcome fear, navigate uncertainty, and achieve meaningful goals.

Preparation creates a competitive advantage. Whether you're flying a fighter jet, making a sales call, or delivering a keynote, success rarely comes from winging it. Research your audience, understand their needs, and put in the work before you show up.

Commitment creates freedom. Keeping every option open can make it easy to avoid difficult decisions. Choosing a meaningful goal and committing to it forces you to focus, take action, and find a way forward—even when you don't feel completely ready.

Build your platform before you need it. Don't wait until your book is published or your product is ready to start building an audience. Share your expertise through articles, speaking, podcasts, and other channels so you have relationships, credibility, and potential customers when the time comes to launch.

"Wingman never wings it."

"When you have a lot of choices in front of you, it's you can make excuses for all of them."

"When you're having a tough time, you sell—you're having a tough sale, focus on the customer."

LinkedIn: linkedin.com/in/waldowaldman

Instagram: https://www.instagram.com/waldowaldman/

Other: YourWingman.com | Commit Commit *pre-order now, available Nov. 17th, 2026

Why there's almost never a viral moment, and how Hari's first 10,000 subscribers took nearly three years, while the next 90,000 took just one more

How Hari used his YouTube income and influencer partnerships to grow Silo Markets from $3 million to $123 million in deposits

Chris Sain's "start before you're ready" philosophy, beginning with $250 and small automatic investments in index funds

Earning trust through consistency and proof: showing up on bad market days and putting your own money behind what you teach

Jo Piazza on the changing attention economy, writing her first three books during her day job, keeping her IP, and why self-publishing no longer carries a stigma

An audience is an asset that compounds, so start early. Growth is slow at the beginning. Hari's first 1,000 subscribers took nine months, but every subscriber made the next one easier. The best time to build an audience is before you have anything to sell it.

You will never feel ready, so don't wait until you do. Whether it's $50 into an index fund every payday or your first Substack post, small and consistent actions build the habits, skills, and credibility that bigger opportunities need.

In an internet full of AI content, a trusted human voice is worth more. Chris built loyalty by practicing what he preaches and showing up every day. Jo uses her podcast to stay in direct, regular contact with her audience. People follow people they trust.

"There was never a viral moment. It was always just, step by step, subscriber by subscriber." (Hariharan Jayakumar)

"I'm a guy that's standing on high character, high integrity, and I can show you better than I can tell you." (Chris Sain)

"Build an audience early, often, and use everything you can to try to do that from the very start." (Jo Piazza)

LinkedIn: linkedin.com/in/hariharan-jayakumar-silo

Instagram: @hariharan.jayakumar

Other: Logically Answered on YouTube | Silo Markets

Full interview: Make Money by Turning a YouTube Audience Into a Fintech Business

Instagram: @chris_sain

Other: chrissain.com | Quiet Wealth Club | TikTok

Full interview: Make Money By Starting Before You Are Ready

Website: jopiazza.com

Other: The Parisian Heist 

Full interview: Make Money Building an Audience and Surviving the Attention Economy

Why Airbnb hosts are facing backlash for charging cleaning fees while asking guests to complete checkout chores

How traditional hotels are winning travelers back with consistent service, amenities, loyalty programs, and a more welcoming experience

Why running a small business doesn't excuse a poor customer experience

How marketplaces like Airbnb and Uber eventually have to prioritize customers over providers

Why unique properties and memorable experiences are Airbnb's best opportunity to stand out from hotels

Your competition sets the standard. It doesn't matter whether you think your checkout list is reasonable. If a hotel offers a better experience with fewer hassles, customers have a compelling reason to choose it instead.

Don't make customers pay for your operational problems. Running a business comes with responsibilities. If cleaning schedules, laundry, or trash collection are difficult to manage, it's up to the owner to find a solution rather than shifting those burdens onto paying guests.

Give customers a reason to choose you. Airbnb's advantage is the opportunity to offer unique homes, extra space, and memorable experiences. Hosts who focus on those benefits can differentiate themselves from traditional hotels instead of competing on convenience and price alone.

“Your competitor is a better option, you will lose business, period.”

“This isn't about respect. You're a business owner offering a service to a customer.”

“Guests have options on where they choose to stay. They drive the market, not the other way around.”

Instagram: https://www.instagram.com/travischappell/

Website: travischappell.com

How door-to-door sales and landscaping taught Chris the value of hard work, autonomy, and entrepreneurship.

What Chris learned about leadership and innovation from working with companies like Apple, Disney, and Dell.

Why small businesses need clear strategies, focused priorities, and strong cultural principles to grow.

How serving customers and genuinely meeting their needs can lead to greater financial success.

Why co-creation, vulnerability, and a willingness to learn are essential for building high-performing teams in the age of AI.

Focus on a few priorities that actually matter. A strategy isn't a laundry list of projects. Identify your four or five core priorities and use them as a filter for deciding what deserves your time and resources. If something doesn't align, be willing to let it go.

Build your business around serving people. Making money is an outcome, not the ultimate purpose. When you focus on understanding customers, meeting their needs, and delivering real value, financial results can follow.

Your team's potential is greater than the sum of its parts. As AI makes knowledge and execution more accessible, collaboration becomes an even bigger competitive advantage. Build a culture where people can challenge ideas, share feedback, and create better solutions together.

"If you just put the effort in, things happen."

"The best entrepreneur, the best business work we can do is service."

"My greatest skill is that I was a sponge."

LinkedIn: https://www.linkedin.com/in/chris-deaver/

Instagram: https://www.instagram.com/influence.bydesign/

Other: Bravecore | Brave Together by Chris Deaver and Ian Clawson

Airbnb’s new policy restricting hosts from requiring guests to complete certain cleaning chores at checkout

Why excessive cleaning fees, checkout rules, and hidden restrictions are driving travelers back to hotels

The misconception that Airbnb is a passive income business and the work required to succeed in hospitality

How businesses risk becoming the outdated, frustrating alternatives they originally disrupted

Why creating unique experiences and prioritizing customer satisfaction are key to standing out in a competitive market

The best customer experience wins. Customers will gravitate toward the option that offers the most value and convenience. Businesses that make the experience frustrating risk losing customers to competitors who do it better.

Passive income still requires real work. Airbnb hosts are operating hospitality businesses, not simply collecting checks. Building effective systems and teams can make a business more hands-off, but delivering a great customer experience remains the owner's responsibility.

Don't become the industry you disrupted. Companies often win by solving the frustrations of existing alternatives. But when they introduce excessive fees, unnecessary rules, or declining service, they create an opening for the next competitor to take their place.

"The product that helps the customer the best will win in the end."

"If you become the legacy industry, then you are leaving room to be disrupted by something else that is a better experience for the customer."

"At the end of the day, you are literally a boutique hotel owner."

Instagram: Travis Chappell on Instagram

Other: travischappell.com

How Kristen turned a college side hustle into a cleaning business that doubled as a leadership development company.

Why discovering what you don't want to do can help you find the right career path.

The lessons Kristen learned from accumulating more than $300,000 in business debt and paying it off five years ahead of schedule.

Why transparency and vulnerability can help leaders build stronger, more supportive teams.

How to recognize when you've outgrown your business and find the courage to pursue a new direction.

Your path doesn't have to be linear. Sometimes, discovering what you don't enjoy is just as valuable as finding what you're passionate about. Kristen didn't set out to become a leadership expert, but running her cleaning company helped her discover where she felt most alive.

Transparency gives your team the opportunity to help. Kristen initially tried to protect her employees from the full reality of the company's financial struggles. When she finally shared the true debt number, her team rallied around a plan to pay it off. Leaders don't have to carry every burden alone.

Your business should evolve as you do. It's easy to tie your identity to the company you've built, even when your interests and priorities change. Kristen's experience shows that letting go of one version of success can create room for a more fulfilling one.

“I think you have to learn a lot of what isn't your thing to get to the thing that is yours.”

“If I as the leader am not super passionate about what I'm doing, I'm not being a great leader for my team.”

“There are probably so many people around you that wanna help if you can just give them the chance to.”

Website: KristenHadeed.com

Instagram: https://www.instagram.com/kristenhadeed/

Book: Human Leadership — available wherever books are sold.

Previous Book: Permission to Screw Up