INTERVIEW | Make Money by Investing Smarter: Keith Smith on Private Capital, AI, and Building Businesses That Last

Travis Chappell, entrepreneur and podcast host, shares his insights on the Insurance Dudes Podcast about building a successful business, growing an audience, and creating a life aligned with your own goals. After spending years in door-to-door sales, Travis took a pay cut to pursue podcasting full-time, eventually turning his show into a powerful tool for building relationships and creating opportunities. In this conversation, he explains why slow, consistent progress beats chasing overnight success, how content creation can help entrepreneurs stand out in competitive industries, and why getting clear on what you truly want is essential to building a fulfilling life. On this episode we talk about: How door-to-door sales taught Travis communication, emotional intelligence, and the importance of understanding people. Why consistency and quality are the keys to growing a podcast, even when downloads and engagement are low. How creating content helps entrepreneurs build a loyal audience, stand out in competitive markets, and make their businesses more resilient during economic downturns. Why regularly revisiting your goals helps ensure you're pursuing what you actually want rather than following society's or your family's expectations. The power of investing in yourself, building meaningful relationships, and becoming so good at your craft that people can't ignore you. Top 3 Takeaways Consistency and quality beat overnight success. Building a successful podcast, business, or career takes time. Keep showing up, improve your skills, and focus on serving the people who are already paying attention instead of obsessing over the results you haven't achieved yet. Get clear on your goals and make sure they're actually yours. Take time every week to evaluate whether you're still pursuing the right outcomes. Don't spend years working toward a version of success that society, your family, or someone else defined for you. Adjust your course when your priorities change. Build relationships and an audience before you need them. Creating valuable content helps you establish trust, connect with influential people, and develop a loyal community. For entrepreneurs in industries like insurance, real estate, and lending, that trust can become a major competitive advantage and help sustain a business through difficult economic periods. Notable Quotes "Be so good they can't ignore you." "The thing that's gonna keep you stuck is just not doing anything." "If you help enough people in the world, get what they want, you can have everything that you want." Connect with Travis Chappell: Instagram: @travischappell  Other: https://travischappell.com A Word from Our Sponsors: - The most successful business owners don't do it all themselves — they delegate. Upwork lets you build a team of highly skilled specialists for every function your business needs, so you can focus on what you do best and let experts handle the rest. Visit Upwork.com right now and post your job for free! - Scribe captures workflows as work happens and automatically generates step-by-step guides with screenshots and instructions, so no one has to sit down and write documentation from scratch. Learn more at scribe.how/tmm and mention Travis Makes Money for your first month of Scribe Capture free on select plans. - When you need a legal hand, visit LegalZoom. Go to LegalZoom.com to get started! Learn more about your ad choices. Visit megaphone.fm/adchoices

Keith Smith is the co-founder and CEO of Goodstream, an AI-native portfolio intelligence platform that helps private capital investors track investments and analyze complex financial documents without manual data entry. A founder and CEO for more than 30 years, Keith has launched seven companies and spent nine years running Payability, where he managed portfolio companies and more than $6 billion in financing. In this episode, he shares the lessons he’s learned from decades of entrepreneurship, explains how AI is changing private-market investing, and discusses why buying a business isn’t the shortcut to passive income that some people make it out to be. On this episode we talk about: How selling mechanical pencils in seventh grade sparked Keith’s entrepreneurial ambitions and led to a career building technology companies. Why profit, cash flow, and financial discipline matter more than impressive revenue numbers. How Keith’s experience in private credit exposed the challenges of tracking private investments and inspired him to build Goodstream. Why buying an existing business still requires serious operational expertise, resilience, and an understanding of financial statements. How entrepreneurs can use AI and modern technology to improve established businesses and unlock new growth opportunities. Top 3 Takeaways Entrepreneurship requires resilience, not just enthusiasm. Whether you start a company from scratch or acquire an existing business, expect obstacles and be prepared to work through them. The ability to keep solving problems is essential to success. Understand the numbers before making big decisions. Revenue alone doesn't tell you whether a business is healthy. Strong margins, predictable profitability, and disciplined financial management can create a much stronger foundation for growth. AI can create opportunities in overlooked businesses. Established companies may already have good customers and healthy margins but rely on outdated processes. Entrepreneurs who understand both the business and how to implement technology can find meaningful opportunities to improve efficiency and profitability. Notable Quotes “Just be better than yesterday and you'll eventually find yourself in a better spot.” “Don't do it.” — Keith’s deliberately blunt advice to aspiring entrepreneurs who might not be prepared for the challenges of running or acquiring a business. “The adoption and the diffusion of AI is going to be slowed more by human habits than by anything else.” Connect with Keith Smith Company: Goodstream LinkedIN: https://www.linkedin.com/in/keithlsmith/ X (Twitter): @GS Fine Print — Startup, fundraising, and investor insights shared through Goodstream’s account. A Word from Our Sponsors - The most successful business owners don't do it all themselves — they delegate. Upwork lets you build a team of highly skilled specialists for every function your business needs, so you can focus on what you do best and let experts handle the rest. Visit Upwork.com right now and post your job for free! - Scribe captures workflows as work happens and automatically generates step-by-step guides with screenshots and instructions, so no one has to sit down and write documentation from scratch. Learn more at scribe.how/tmm and mention Travis Makes Money for your first month of Scribe Capture free on select plans. - When you need a legal hand, visit LegalZoom. Go to LegalZoom.com to get started! Learn more about your ad choices. Visit megaphone.fm/adchoices

Travis Chappell, host of the Travis Makes Money podcast, joins Chris Hill on Money Unplugged to share the money lessons that shaped his approach to business, wealth, and financial freedom. From growing up with a frugal real estate agent father to building businesses as a teenager and earning six figures in door-to-door sales before turning to podcasting, Travis explains how his early experiences influenced his financial philosophy. He also discusses why increasing your income is often more powerful than obsessing over small expenses, how to avoid lifestyle creep, and why patience is essential when building lasting wealth. On this episode we talk about: How Travis's parents shaped his relationship with money, including his dad's preference for investing in real estate over buying expensive cars. Starting a landscaping business as a teenager and earning six figures in door-to-door solar sales in his early twenties. Why Travis reconsidered a career in ministry after discovering his passion and success in sales. Why increasing your income can be more impactful than obsessing over small expenses, and how to balance earning more with financial discipline. How to avoid lifestyle creep, invest in your future, and know when it's finally time to enjoy the money you've worked hard to earn. Top 3 Takeaways Focus on increasing your income, not just cutting expenses. Financial discipline matters, but there is a limit to how much you can save by spending less. Building new income streams through a business, side hustle, or investments can create far more opportunities to grow your wealth. Don't let lifestyle creep erase your progress. When your income increases, resist the urge to immediately upgrade your house, car, and spending habits. Give yourself time to save and invest the difference so compounding can work in your favor. Build wealth first, then enjoy it intentionally. You don't have to live frugally forever. Make smart financial decisions early, invest in yourself, and delay major purchases until you can afford them without compromising your financial security. The goal is to enjoy your money without sacrificing the freedom it can provide. Notable Quotes "The thing that's gonna keep you stuck is just not doing anything." "You can only cut to zero, but you can earn infinitely in the opposite direction." "I am convinced that the most difficult part of wealth building is not getting to the point where you make more money. It's remaining at the same lifestyle spend that you were at when you were making less money." Connect with Travis Chappell: Instagram: @travischappell  Other: https://travischappell.com A Word from Our Sponsors: - The most successful business owners don't do it all themselves — they delegate. Upwork lets you build a team of highly skilled specialists for every function your business needs, so you can focus on what you do best and let experts handle the rest. Visit Upwork.com right now and post your job for free! - Scribe captures workflows as work happens and automatically generates step-by-step guides with screenshots and instructions, so no one has to sit down and write documentation from scratch. Learn more at scribe.how/tmm and mention Travis Makes Money for your first month of Scribe Capture free on select plans. - When you need a legal hand, visit LegalZoom. Go to LegalZoom.com to get started! Learn more about your ad choices. Visit megaphone.fm/adchoices

Ryan White is the founder and CEO of Social Revelation, an Instagram authority and positioning firm that has served more than 3,000 entrepreneurs and brands since 2017. With an audience of more than 3 million on Instagram and experience helping experts build their online presence, Ryan has spent nearly a decade figuring out what actually works in social media. In this episode, he shares how he grew his business from a $30-a-month service into a high-ticket agency, why profit matters more than revenue, and how entrepreneurs can build authority online without turning content creation into a full-time job. On this episode we talk about: How Ryan turned his Instagram skills into a business and grew to 600 clients in his first 18 months. Why entrepreneurs should focus on profit, cash flow, and lifestyle instead of chasing impressive revenue numbers. The evolution of Social Revelation from low-ticket software to high-ticket, done-for-you services. Why selling higher-priced services can help entrepreneurs improve margins, learn valuable skills, and grow faster. How to build an Instagram audience intentionally by optimizing your profile, targeting the right people, and creating content that keeps viewers watching. Top 3 Takeaways Focus on what you keep, not just what you make. Revenue can look impressive on paper, but profit and cash flow determine how much financial freedom your business actually creates. Build a business that serves your life. Scaling isn't automatically better. Consider the stress, overhead, and responsibilities that come with growth, and decide what you actually want your business to provide. Make your content work strategically. Rather than posting constantly just to stay active, focus on reaching the right audience, communicating your expertise, and creating videos people want to watch through to the end. Notable Quotes “It's not about what you make, it's what you keep.” “How can your business serve you? Not how do you serve your business?” “How do we help people become content snipers instead of machine gun firers?” Connect with Ryan White Instagram: @CEO Ryan White Website: Official Ryan White Company: Social Revelation A Word from Our Sponsors - The most successful business owners don't do it all themselves — they delegate. Upwork lets you build a team of highly skilled specialists for every function your business needs, so you can focus on what you do best and let experts handle the rest. Visit Upwork.com right now and post your job for free! - Scribe captures workflows as work happens and automatically generates step-by-step guides with screenshots and instructions, so no one has to sit down and write documentation from scratch. Learn more at scribe.how/tmm and mention Travis Makes Money for your first month of Scribe Capture free on select plans. - When you need a legal hand, visit LegalZoom. Go to LegalZoom.com to get started! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Travis Chappell is joined by producer Eric for an unfiltered conversation about money, consumer culture, and the ways businesses and organizations pressure people to spend. From a viral Shake Shack kiosk video that appears to raise prices when a customer declines to tip to the growing use of buy now, pay later services, Travis and Eric discuss where convenience crosses the line into manipulation. They also explore the ethics of religious fundraising, questionable claims of faith healing, and why transparency and accountability matter whenever money is involved. On this episode we talk about: How buy now, pay later services like Klarna and Affirm influence purchasing decisions, and why interest-free financing changes the equation. A viral Shake Shack kiosk video that appears to increase item prices after a customer declines to tip, sparking a debate about tipping culture and hidden costs. Why tipping should be about exceptional service rather than an automatic expectation at every checkout screen. The ethics of religious fundraising, including donation kiosks, financial pressure on congregations, and the potential harm of manipulative fundraising practices. Why extraordinary faith-healing claims deserve scrutiny, especially when vulnerable people facing serious illnesses may be led to expect miracles. Top 3 Takeaways Understand the true cost of borrowing. Before using a buy now, pay later service, consider whether you're paying interest or fees and whether the purchase fits your budget. Interest-free financing can be useful, but it shouldn't encourage spending money you don't have. Question fees and tipping expectations. Customers deserve transparent pricing. A tip should feel like a voluntary reward for good service, not an unexpected charge or a requirement imposed by a checkout system. Be skeptical when money and vulnerability intersect. Whether it's a business using confusing pricing or an organization soliciting donations through emotional appeals, take a closer look at where the money goes and whether the claims being made are supported. Notable Quotes "I just think that they existed for a reason and now they're like their own independent category of taxes." "If you start just giving it away for everything, then it then it becomes an entitlement thing instead of extra money for exceptional service thing." "Why aren't you going to every hospital and cancer ward and kids chemo place?" Connect with Travis Chappell: Instagram: @travischappell  Other: https://travischappell.com A Word from Our Sponsors: - The most successful business owners don't do it all themselves — they delegate. Upwork lets you build a team of highly skilled specialists for every function your business needs, so you can focus on what you do best and let experts handle the rest. Visit Upwork.com right now and post your job for free! - Scribe captures workflows as work happens and automatically generates step-by-step guides with screenshots and instructions, so no one has to sit down and write documentation from scratch. Learn more at scribe.how/tmm and mention Travis Makes Money for your first month of Scribe Capture free on select plans. - When you need a legal hand, visit LegalZoom. Go to LegalZoom.com to get started! Learn more about your ad choices. Visit megaphone.fm/adchoices

Andrea Petrone is an executive coach who has spent more than two decades working with senior leaders at companies including Shell, Unilever, Takeda, EssilorLuxottica, and PwC. After coaching more than 250 CEOs and C-suite executives, he recognized a common challenge: leaders often lose touch with their identity when the pressure rises. In his new book, Reinvention at the Top: The Playbook for CEOs to Lead Under Pressure, Andrea introduces his “Through Line” methodology to help leaders define who they are, communicate what they stand for, and adapt their leadership style to changing circumstances. On this episode we talk about: How Andrea went from working in the oil and gas industry to becoming a CEO at just 35 years old. Why earning a higher salary and achieving career success don't necessarily translate into happiness or fulfillment. Why leaders struggle under pressure when they rely on the same leadership playbook in every situation. The dangers of command-and-control leadership and how it can lead to disengaged employees and poor organizational results. How Andrea turned years of executive coaching and daily writing into his book and a methodology designed to help leaders reinvent themselves. Top 3 Takeaways Your leadership style must evolve with your circumstances. The approach that helped you reach the top might not be the approach you need to succeed there. Recognize when your environment changes and adapt accordingly. Leading under pressure is a skill you can develop. Natural temperament and emotional control can help, but they don't guarantee success. Leaders must learn to recognize changing expectations, understand their impact, and adjust their behavior. Understand your identity before trying to change your performance. Effective leadership goes beyond learning communication techniques or running better meetings. It requires clarity about who you are, what you stand for, and what your organization needs from you. Notable Quotes "When the waters are calm, it's to some extent it's easy to lead." "They have one single playbook, that's their version of leadership and they apply every single time everywhere." "The point is having the methodology bringing to life because my perspective is there is no really conversation happening at that level. That the level of an introspection about your own identity, how to lead." Connect with Andrea Petrone: LinkedIn: https://www.linkedin.com/in/andreapetrone/ Other: Reinvention at the Top (book) A Word from Our Sponsors: - The most successful business owners don't do it all themselves — they delegate. Upwork lets you build a team of highly skilled specialists for every function your business needs, so you can focus on what you do best and let experts handle the rest. Visit Upwork.com right now and post your job for free! - Scribe captures workflows as work happens and automatically generates step-by-step guides with screenshots and instructions, so no one has to sit down and write documentation from scratch. Learn more at scribe.how/tmm and mention Travis Makes Money for your first month of Scribe Capture free on select plans. - When you need a legal hand, visit LegalZoom. Go to LegalZoom.com to get started! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of the Travis Makes Money Podcast, Travis and producer Eric sit down for a conversation about subscription fatigue, frustrating customer experiences, and a new policy in New York City designed to make canceling subscriptions easier. They discuss Mayor Zohran Mamdani's new click-to-cancel rule, share their own experiences trying to escape unwanted gym memberships and activity-tracking subscriptions, and explore why businesses that make it easy for customers to leave may actually be better positioned to earn their business again in the future. Along the way, they also talk about technology overload, the appeal of analog tools, and why sometimes simpler really is better. On this episode we talk about: New York City's click-to-cancel rule and how it aims to protect consumers from deceptive subscription practices Personal experiences with difficult cancellation processes at Planet Fitness and WHOOP Why forcing customers through surveys, retention offers, and unnecessary steps creates a poor customer experience How making subscriptions easy to cancel can build trust and increase the likelihood that customers return Subscription fatigue, technology overload, and the growing appeal of books, notebooks, journaling, and other analog alternatives Top 3 Takeaways Make it as easy to cancel as it is to sign up. If customers can subscribe with one click, they shouldn't have to navigate a maze of phone calls, surveys, and retention offers to leave. A straightforward cancellation process respects their time and autonomy. A frustrating customer experience can cost you future business. Making it difficult for customers to cancel may keep them paying temporarily, but it can leave them so frustrated that they refuse to return—even if they previously liked the product. Not every problem needs more technology. Subscriptions, apps, notifications, and connected devices can add unnecessary complexity. Sometimes simpler, more tactile alternatives like paper notebooks and journaling offer a welcome break from digital overload. Notable Quotes "No one should need 45 minutes of hold music to stop paying for something they never wanted." — Quoted by Eric from Mayor Zohran Mamdani's announcement "If a company can take your money with one click, you should be able to get your money back with one click." — Quoted by Eric from Mayor Zohran Mamdani's announcement "When I'm forced through all these hoops, I just go like, I'm never doing this again." — Travis, on frustrating subscription cancellation experiences Connect with Travis Chappell: Instagram: @travischappell   Other: https://travischappell.com A Word from Our Sponsors: - The most successful business owners don't do it all themselves — they delegate. Upwork lets you build a team of highly skilled specialists for every function your business needs, so you can focus on what you do best and let experts handle the rest. Visit Upwork.com right now and post your job for free! - Scribe captures workflows as work happens and automatically generates step-by-step guides with screenshots and instructions, so no one has to sit down and write documentation from scratch. Learn more at scribe.how/tmm and mention Travis Makes Money for your first month of Scribe Capture free on select plans. - When you need a legal hand, visit LegalZoom. Go to LegalZoom.com to get started! Learn more about your ad choices. Visit megaphone.fm/adchoices

Rakesh Kumar is a professor and John Bardeen Faculty Scholar in computer engineering at the University of Illinois and a renowned expert on semiconductors. His research has helped shape the chips powering the phones, tablets, and computers we use every day, and he has advised chip companies, startups, governments, and intelligence firms. In this episode, Rakesh breaks down the fascinating history of computer chips, explains how advances in chip technology have fueled the AI boom, and explores how quantum computing could transform everything from scientific discovery to cybersecurity. He is also the author of the upcoming book The Chip Age: How Semiconductors Became the World's Most Powerful Resource. On this episode we talk about: How computer chips work, why they're so revolutionary, and the history behind their invention Moore's Law and how the semiconductor industry has continually doubled the number of transistors on a chip The relationship between AI's growth, computing power, and the billions of dollars being invested in chip technology How quantum computing differs from traditional computing and when it could become commercially useful The potential impact of quantum computing on encryption, weather forecasting, drug discovery, and material science Top 3 Takeaways Technology advances when people turn ambitious goals into industry-wide priorities. Moore's Law began as an observation about transistor growth, but the semiconductor industry adopted it as a goal and worked collectively to keep pushing the limits of computing power. AI and semiconductors depend on each other. More powerful chips made modern AI possible, while AI's growing commercial potential is driving further investment in chip development. However, this feedback loop also raises the stakes if either industry fails to deliver. Quantum computing could unlock solutions to problems traditional computers struggle to solve. From discovering new drugs and materials to improving weather predictions, quantum computers could make complex scientific problems more tractable. But building useful, cost-effective systems remains a major engineering challenge. Notable Quotes "Think of a chip as essentially an electronic tiny brain." "Moore's Law, it was no law at all. It was just an observation that somebody made." "Science continues to be very hard." Connect with Rakesh Kumar: Other: Check out his book, The Chip Age: How Semiconductors Became the World's Most Powerful Resource. A Word from Our Sponsors: - The most successful business owners don't do it all themselves — they delegate. Upwork lets you build a team of highly skilled specialists for every function your business needs, so you can focus on what you do best and let experts handle the rest. Visit Upwork.com right now and post your job for free! - Scribe captures workflows as work happens and automatically generates step-by-step guides with screenshots and instructions, so no one has to sit down and write documentation from scratch. Learn more at scribe.how/tmm and mention Travis Makes Money for your first month of Scribe Capture free on select plans. - When you need a legal hand, visit LegalZoom. Go to LegalZoom.com to get started! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this two-part conversation, Travis Chappell dives into the nuanced decisions couples face around career, parenting, and societal expectations. Picking up from part one, Travis explores what it means to support a partner, balance personal ambition, and navigate cultural pressures around stay-at-home roles, both for women and men. This episode blends practical advice, personal anecdotes, and cultural commentary to help listeners rethink traditional expectations. On this episode we talk about: How couples can decide who stays home without feeling societal pressure The psychological dynamics and respect factors in modern household roles Lessons from Travis’s own family experience and experimentation over a decade The influence of feminism, tradition, and societal messaging on career and parenting choices Strategies for testing and adapting your life choices as circumstances evolve Connect with Travis Chappell: LinkedIn: ⁠https://www.linkedin.com/in/travischappell⁠ Instagram: ⁠https://www.instagram.com/travischappell⁠ Other: ⁠https://travischappell.com⁠ A Word from Our Sponsors:- The most successful business owners don't do it all themselves — they delegate. Upwork lets you build a team of highly skilled specialists for every function your business needs, so you can focus on what you do best and let experts handle the rest. Visit Upwork.com right now and post your job for free! - Scribe captures workflows as work happens and automatically generates step-by-step guides with screenshots and instructions, so no one has to sit down and write documentation from scratch. Learn more at scribe.how/tmm and mention Travis Makes Money for your first month of Scribe Capture free on select plans. - When you need a legal hand, visit LegalZoom. Go to ⁠LegalZoom.com⁠ to get started!⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Celeste Durve is a founder, writer, and speaker exploring the intersection of emotional intelligence, personal development, and modern success. She is the founder and CEO of Viper, a national staffing, talent, and experiential advisory firm, and the creator of Smart is Sexy, a rapidly growing media platform and Substack community with more than 300,000 readers. A Forbes 30 Under 30 honoree, Celeste built her business without a college degree or an entrepreneurial background, starting with unpaid internships and small event-staffing opportunities before growing into a multi-market company. In this episode, she shares how to create opportunities for yourself, validate business ideas, and build a life through execution rather than excuses. On this episode we talk about: How Celeste turned unpaid work into a business opportunity, starting with a $100 payment for her early event-staffing services. Why you don't necessarily need a college degree to succeed—and how to evaluate whether higher education makes sense for your goals. Why testing an idea with paying customers is more valuable than relying on surveys, assumptions, or AI-generated encouragement. How Celeste rebuilt her business after COVID and grew Viper into multiple markets while developing new experiential marketing programs. How Smart is Sexy grew to more than 300,000 readers by sharing honest, practical advice about personal responsibility, self-development, and execution. Top 3 Takeaways Create opportunities instead of waiting for permission. Celeste started by offering her services for free to gain experience and prove her concept. When an employer rejected her idea, she tested it independently with people in her network. You don't need someone else's approval to take the first step. Validate ideas through actual sales. Positive feedback doesn't necessarily mean people will pay for your product or service. Start small, find someone willing to buy, and use real customer feedback to refine your offering. Execution—not the idea itself—is what determines whether a business has potential. Build stability by taking ownership of your future. Celeste's desire for stability came from her upbringing and led her to build a business she could control. Entrepreneurship comes with uncertainty, but developing valuable skills, adapting to setbacks, and managing your finances can help you navigate the ups and downs. Notable Quotes “If nobody's offering you opportunity, it's up to you to create it.” “You're the only success is in execution and actually making a sale.” “I was always a big believer in not being just a victim to my circumstances.” Connect with Celeste Durve: Website: https://celestedurve.com/ Instagram: Celeste Durve, Smart is Sexy, Viper Other: Smart is Sexy on Substack  A Word from Our Sponsors: - The most successful business owners don't do it all themselves — they delegate. Upwork lets you build a team of highly skilled specialists for every function your business needs, so you can focus on what you do best and let experts handle the rest. Visit Upwork.com right now and post your job for free! - Scribe captures workflows as work happens and automatically generates step-by-step guides with screenshots and instructions, so no one has to sit down and write documentation from scratch. Learn more at scribe.how/tmm and mention Travis Makes Money for your first month of Scribe Capture free on select plans. - When you need a legal hand, visit LegalZoom. Go to LegalZoom.com to get started! Learn more about your ad choices. Visit megaphone.fm/adchoices