The Business of NIL: Parents, Brands, and the Power Behind College Sports | Justin J. Giangrande

Founder Lessons From Scaling, Going Public, and Rebuilding | Rick Jordan

Ryan Alford talks with Rick Jordan about one of the hardest founder arcs to navigate: building real momentum, scaling quickly, and then being forced to confront what happens when part of that structure fails. Rick walks through taking his company public, the acquisitions that accelerated growth, and the liabilities that later turned those wins into a painful and expensive reset. The conversation is honest about the things founders do not always say out loud. Ryan and Rick unpack the emotional side of leadership, the tendency to internalize every failure, the danger of writing checks just to buy more time, and why entrepreneurs often carry burdens no one else inside the company truly feels. They also talk about what comes next: rebuilding with stronger structure, teaching other business owners what Rick learned the hard way, and focusing on scalable systems that can survive more than just the first burst of momentum. It is a candid, useful listen for anyone trying to grow without confusing speed for stability. Topics Covered * Rick Jordan’s path from private business growth to public markets * How acquisitions helped scale the company quickly * What happens when acquired businesses bring hidden problems * The legal and structural difference between buying stock and buying assets * Why founders often over-own the pain of failure * The cost of trying to save a business the wrong way * Rebuilding with better structure and clearer boundaries * Ryan Alford and Rick Jordan on scaling, scars, and second chances Links Right About Now https://www.ryanisright.com/ [https://www.ryanisright.com/]https://podcasts.apple.com/us/podcast/right-about-now-legendary-business-advice/id1346054199 [https://podcasts.apple.com/us/podcast/right-about-now-legendary-business-advice/id1346054199]https://www.youtube.com/@RightAboutNowwithRyanAlford [https://www.youtube.com/@RightAboutNowwithRyanAlford] Ryan Alford https://www.ryanalford.com/ [https://www.ryanalford.com/]https://www.instagram.com/ryanalford/ [https://www.instagram.com/ryanalford/] Rick Jordan https://www.mrrickjordan.com/ [https://www.mrrickjordan.com/]https://www.instagram.com/mrrickjordan/ [https://www.instagram.com/mrrickjordan/]https://www.youtube.com/@mrrickjordan [https://www.youtube.com/@mrrickjordan] ReachOut Technology https://www.reachoutit.com/ [https://www.reachoutit.com/] Frequency Holdings https://www.frequencyholdings.com/ [https://www.frequencyholdings.com/]

How a Viral Congressional Trading Tracker Became a $1B+ Fintech Business | Autopilot

Ryan Alford talks with Chris Josephs, co-founder of Autopilot, about how political stock-trade tracking became one of the most talked-about ideas in finance media and how that momentum evolved into a real investing business. Chris explains the origin of the Pelosi Tracker, why the topic hit such a nerve with both parties, and how Autopilot now gives users a way to follow portfolios from politicians, hedge funds, AI-driven strategies, and vetted independent investors. The conversation also digs into product design, marketplace thinking, and what Chris believes is broken in traditional investing. Ryan and Chris explore the black-box problem with advisors and retirement accounts, why transparency matters more than ever, and how accountability can become a real competitive edge in a world increasingly flooded by AI-generated noise. They close by talking about virality, founder strategy, and the difference between chasing attention and using attention to build durable trust. It is a useful episode for entrepreneurs, investors, and operators who want to understand how a sharp media insight can turn into a differentiated product with real staying power. Topics Covered * The origin story behind the Pelosi Tracker * Why political stock trading became such a viral topic * How Autopilot works inside existing brokerage accounts * The marketplace model for following investors * Why transparency and verification matter in modern finance * Chris Josephs’ view on AI, emotion, and stock research * Why virality is overrated without product-market fit * Ryan Alford and Chris Josephs on trust, investing, and founder execution Links Right About Now https://www.ryanisright.com/ [https://www.ryanisright.com/]https://podcasts.apple.com/us/podcast/right-about-now-legendary-business-advice/id1346054199 [https://podcasts.apple.com/us/podcast/right-about-now-legendary-business-advice/id1346054199]https://open.spotify.com/show/0gy9HkTiwpAAgu1DFyIW9h [https://open.spotify.com/show/0gy9HkTiwpAAgu1DFyIW9h]https://www.youtube.com/@RightAboutNowwithRyanAlford [https://www.youtube.com/@RightAboutNowwithRyanAlford] Ryan Alford https://www.ryanalford.com/ [https://www.ryanalford.com/]https://www.instagram.com/ryanalford/ [https://www.instagram.com/ryanalford/] Chris Josephs / Autopilot https://www.joinautopilot.com/ [https://www.joinautopilot.com/]https://www.instagram.com/chrisjjosephs/ [https://www.instagram.com/chrisjjosephs/]https://x.com/pelositracker [https://x.com/pelositracker]https://pelositracker.app/ [https://pelositracker.app/]

How AI Is Changing Retail, Style, and the Future of Shopping | Anya Cheng

Ryan Alford sits down with Anya Cheng, founder and CEO of Taelor, for a conversation about AI, commerce, branding, and why data is becoming the defining advantage in the next generation of startups. Anya shares how she identified a real customer problem inside fashion and style, why most men do not actually want to shop, and how Taelor was built to remove friction through a mix of AI, logistics, and human styling support. Ryan and Anya also dig into the balance between brand and performance marketing, the changing role of SEO in a ChatGPT world, and why founders should be thinking less about building models and more about owning differentiated data. The episode becomes a bigger discussion about business moats, customer behavior, and how the most valuable AI companies may come from industries that do not look flashy at first glance. They close with a sharp look at live shopping, social commerce, and where Anya believes U.S. consumer behavior is headed next. It is a useful listen for entrepreneurs trying to separate what is durable in AI from what is just noise. Topics Covered * How Anya Cheng went from major tech companies to founding Taelor * Why solving the right problem is more important than building the right feature * The role of AI and human stylists in modern commerce * Why unique data is more valuable than generic model access * Branding, performance marketing, and the purchase funnel * ChatGPT SEO and the rise of answer-based discovery * Live shopping and why U.S. commerce behavior still lags Asia * Ryan Alford and Anya Cheng on defensible AI business strategy Links Right About Now https://www.ryanisright.com/ [https://www.ryanisright.com/?utm_source=chatgpt.com] https://podcasts.apple.com/us/podcast/right-about-now-legendary-business-advice/id1346054199 [https://podcasts.apple.com/us/podcast/right-about-now-legendary-business-advice/id1346054199?utm_source=chatgpt.com] https://www.youtube.com/@RightAboutNowwithRyanAlford Ryan Alford https://www.ryanalford.com/ [https://www.ryanalford.com/] https://www.instagram.com/ryanalford/ [https://www.instagram.com/ryanalford/?utm_source=chatgpt.com] Anya Cheng / Taelor https://taelor.style/ [https://taelor.style/] https://www.linkedin.com/in/anyacheng/ [https://www.linkedin.com/in/anyacheng/?utm_source=chatgpt.com]

How to Build a Career That Can Survive Drastic Change | Jason Feifer

Ryan Alford talks with Jason Feifer about what it really takes to build a durable career in a world that keeps changing faster than people expect. Jason explains why he stopped waiting to be discovered, why every path carries risk, and why adaptability is often the trait that separates the people who keep growing from the people who quietly get left behind. The conversation also digs into storytelling, audience psychology, and what makes content genuinely useful instead of just self-congratulatory. Jason shares how he thinks about serving an audience, why he prefers problem-solving stories over simple success stories, and how that mindset has shaped his work at Entrepreneur and on Build for Tomorrow. By the end, the episode becomes a bigger conversation about how to think long term without becoming rigid, how to stay useful in changing markets, and how to recognize that every decision carries risk whether you move or stay put. It is a thoughtful listen for anyone building a business, a brand, or a career that has to evolve over time. Topics Covered * Why waiting to be chosen is a losing strategy * What Jason Feifer learned from starting at a tiny local paper * Why every career path carries risk * How self-limiting plans close off better opportunities * The audience-first framework for stronger storytelling * Why problem-solving stories outperform generic success stories * The four phases of change from Build for Tomorrow * Ryan Alford and Jason Feifer on reinvention, relevance, and growth Links Right About Now https://www.ryanisright.com/ [https://www.ryanisright.com/?utm_source=chatgpt.com] Ryan Alford https://www.ryanalford.com/ [https://www.ryanalford.com/] https://www.instagram.com/ryanalford/ [https://www.instagram.com/ryanalford/?utm_source=chatgpt.com] Jason Feifer https://www.jasonfeifer.com/ [https://www.jasonfeifer.com/] https://www.instagram.com/heyfeifer/ [https://www.instagram.com/heyfeifer/] Build for Tomorrow https://podcasts.apple.com/us/podcast/build-for-tomorrow/id1104682320 [https://podcasts.apple.com/us/podcast/build-for-tomorrow/id1104682320?utm_source=chatgpt.com] https://open.spotify.com/show/2JWluwXrmvrgeogZCAIWVF [https://open.spotify.com/show/2JWluwXrmvrgeogZCAIWVF?utm_source=chatgpt.com]

The Brutal Reason Most Entrepreneurs Never Scale: Busywork, Sales, and Weak Offers | Tanner Chidester

Ryan Alford talks with Tanner Chidester about the difference between looking productive and actually building a business that makes money. Tanner explains why so many founders are trapped in the wrong tasks, why leads and sales volume still matter more than most people want to admit, and how weak follow-up systems quietly kill otherwise good businesses. The conversation also covers offer design, guarantees, branding, Tanner’s book Infinite Income, and the habits that separate solopreneurs from leaders who can actually scale teams. Ryan brings the operator and agency perspective, while Tanner brings the blunt, tactical lens of someone who has built, sold, hired, fired, coached, and learned the hard way. By the end, the episode becomes a bigger conversation about what it really takes to move from information to action. That includes doing the hard thing you have been avoiding, accepting that no one is coming to save you, and building something strong enough that the market does not need to be convinced as hard in the first place. Topics Covered * Why entrepreneurs often choose busywork over sales work * How better offers reduce friction in marketing and sales * Why follow-up systems matter more than changing media buyers * What Tanner sees inside businesses that are stuck * Why door-to-door sales builds real skill fast * What Tanner would change about Infinite Income * Why Tanner is moving toward a bigger next chapter * Ryan Alford and Tanner Chidester on execution, authority, and scale Links Right About Now https://www.ryanisright.com/ [https://www.ryanisright.com/?utm_source=chatgpt.com] https://www.instagram.com/ryanalford/ [https://www.instagram.com/ryanalford/?utm_source=chatgpt.com] Tanner Chidester https://tannerchidester.com/ [https://tannerchidester.com/?utm_source=chatgpt.com] https://www.instagram.com/tanner.chidester/ [https://www.instagram.com/tanner.chidester/] https://tannerchidester.com/podcast2/ [https://tannerchidester.com/podcast2/?utm_source=chatgpt.com] Elite CEOs https://go.eliteceos.com/main-elite-ceos-careers [https://go.eliteceos.com/main-elite-ceos-careers?utm_source=chatgpt.com] https://go.eliteceos.com/tanner-in-person [https://go.eliteceos.com/tanner-in-person?utm_source=chatgpt.com]