The Business of Secondhand Fashion: AI, Dynamic Pricing & the Future of Resale | Woody Lello (ep. 261)

<p><strong>What if secondhand fashion could work more like the stock market, with real-time data, dynamic pricing and AI helping businesses understand what products are actually worth?</strong></p>

<p>In this episode of the <strong>WS Podcast</strong>, Woj sits down with <strong>Woody Lello</strong>, philosophy graduate and <strong>Co-Founder of Truss Fashion</strong>, to explore the rapidly changing world of <strong>secondhand fashion, resale technology, AI, entrepreneurship and startup survival</strong>.</p>

<p>Woody's journey is anything but conventional. From studying <strong>philosophy</strong> to building a technology company in the resale industry, he explains why philosophical thinking may actually be one of the most useful tools for navigating the uncertainty of entrepreneurship.</p>

<p>We explore:</p>

<ul>

<li>why <strong>philosophy can prepare you for entrepreneurship</strong></li>

<li>how <strong>thought experiments</strong> can help founders make decisions with incomplete information</li>

<li>why the <strong>secondhand fashion market</strong> is becoming increasingly professionalised</li>

<li>how <strong>AI and market intelligence</strong> can transform resale businesses</li>

<li>why secondhand goods could increasingly be priced according to <strong>real-time supply and demand</strong></li>

<li>how <strong>dynamic pricing</strong> can create more value for buyers, sellers and brands</li>

<li>Woody's concept of <strong>"kill criteria"</strong> and knowing when it's time to walk away from a startup</li>