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June 23, 2026
Founder Lessons From Taking a Company Public | Rick Jordan
In this episode of Right About Now, Ryan Alford sits down with Rick Jordan for one of the rawest founder conversations the show has had in a while. Rick opens up about taking his company public, scaling from roughly $4 million to $15 million through acquisitions, and then watching parts of that climb collapse under the weight of bad deals, hidden liabilities, and painful lessons about growth.
What makes this episode work is that it is not just a failure story. Ryan and Rick turn it into a…
June 23, 2026
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 emotiona…
June 19, 2026
How a Viral Congressional Trading Tracker Became a $1B+ Fintech Business | Autopilot
In this episode of Right About Now, Ryan Alford sits down with Chris Josephs, co-founder of Autopilot, to talk about the viral rise of the Pelosi Tracker, what it revealed about political stock trading, and how that insight became the foundation for a real investing platform. Chris explains how Autopilot gives everyday investors a new option beyond passive ETFs, expensive advisors, or random stock picking by allowing them to automatically follow vetted portfolios inside their own brokerage a…
June 19, 2026
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 di…
June 16, 2026
How AI Is Changing Retail, Style, and the Future of Shopping | Anya Cheng
In this episode of Right About Now, Ryan Alford talks with Anya Cheng, founder and CEO of Taelor, about building an AI-powered personal styling business for busy professionals who want to look better without spending more time shopping. Anya explains how her experience at Meta, eBay, McDonald’s, and Target shaped the way she thinks about product-market fit, branding, and one of the most important lessons in building anything: solve the right problem first.
The conversation then moves into…
June 16, 2026
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 …
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