How I Went From Depressed w/ $0 To $500 Million Per Year In My 20's (COMFRT CEO Hudson Leogrande)

The Passionate Few

In this episode, we sit down with 29-year-old entrepreneur Hudson Leo Grande—founder of Comfort—to unpack how he went from being homeless at 16 to building a brand on track to hit $1 billion in revenue in just 3 years. From shipping products out of his mom’s basement to generating $500K/day in sales, Hudson shares the raw truth about e-commerce, mental health, and the mindset it takes to scale fast. If you’ve ever doubted your vision, this episode will shift your perspective.

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Timestamps 00:00:00 – Intro: Meet Hudson Leo Grande ($500M+ entrepreneur at 29) 00:01:12 – Comfort projections: $500M this year, $70M from Purely White 00:02:38 – Dropping out of high school & being homeless at 16 00:06:10 – Early hustles: chimney telemarketing, network marketing, car sales 00:10:55 – Mental health, suicidal thoughts & turning pain into power 00:14:42 – Channeling anger into ambition: ideas, Meek Mill & late-night notes 00:17:33 – Heartbreak in LA & coming back to NY with fire 00:20:21 – Why car sales was the best sales training of his life 00:25:32 – Launching Purely White with $1K: failures, Snap success & setbacks 00:31:45 – The crash: $10M to $2M after Snapchat throttled views 00:34:09 – The idea for Comfort: $5K domain name & a hoodie with meaning 00:37:22 – Comfort’s mental health mission & stories from customers 00:41:15 – First sale, launch strategy & selling $100K+ in the first week 00:44:38 – Dealing with ADHD, overthinking & learning to build systems 00:48:24 – When Comfort hit $500K/day… then $1M/day in sales 00:51:18 – Micro-influencer marketing: why relatability 00:56:00 – TikTok Shop’s halo effect on Amazon, Meta & overall growth 01:00:55 – Scaling with creators & affiliate teams (10 good ones = $1M/mo) 01:04:27 – Growth mindset: the 3 pillars (marketing, product, community) 01:07:43 – Building the perfect product: 12 sample sets to one hyper hoodie 01:10:30 – Hiring A-players & learning to trust your team 01:14:18 – Culture, vision casting & keeping talent motivated 01:18:25 – Hudson’s visualization rituals & the Lamborghini URUS 01:21:22 – From grinding solo to building a billion-dollar team 01:24:40 – Mindset: success, karma, confidence & protecting your energy 01:29:17 – Gift for his dad: $75K Shelby Cobra, $350K Richard Mille 01:31:02 – What money can’t buy: peace, balance & real relationships 01:33:55 – Final advice: “Get out of your own way. Smile through the bullshit.” 01:35:44 – Legacy: “I want my great-great-grandkids to say Hudson changed our bloodline.”

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