E107 - It’s Never Been Easier to Make Money Online (Here’s How) | Hudson Leogrande

Sep 11, 2025

Hudson Leogrande, founder of Comfrt, shares his journey of scaling a seven-figure apparel brand while staying out of the spotlight. He emphasizes the crucial shift from being an influencer to viewing oneself as an entrepreneur. Hudson reveals the impact of AI on content creation and business efficiency, alongside strategies for effective media buying. He reflects on competition, discussing how imitation can be a compliment in business. Insights on collaboration with creators and entering international markets highlight key entrepreneurial lessons for aspiring business owners.

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ADVICE

Negotiate Manufacturing Payment Terms

Negotiate payment terms with manufacturers to avoid paying 100% upfront.
Seek suppliers with deeper bank accounts and net terms like net-90 to buy time to sell inventory.

ADVICE

Use AI To Scale Creative Workflows

Use AI (ChatGPT/Claude) to draft outreach and optimize copy quickly.
Train AI on winning UGC to rate and pre-approve incoming creator videos at scale.

INSIGHT

AI Is A Competitive Survival Lever

AI adoption gives companies massive speed and operational leverage.
Firms that ignore AI risk being out-executed and replaced in business processes.

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Hudson Leogrande is the founder of Comfrt, a rapidly growing apparel brand that’s rethinking the way creators build businesses. In this episode, we unpack how he’s scaled a brand to seven figures while staying almost entirely behind the scenes, and why he believes most creators are missing the mark when it comes to monetisation.

Hudson shares hard-won lessons on building a product people actually want, crafting content that drives sales without being salesy, and the mindset shift from influencer to entrepreneur. A must-listen for anyone serious about turning creativity into real commerce.

00:00 Introduction
01:20 Kicking things off in NYC with viral hoodie success
04:40 Finding the right manufacturers and negotiating better terms
07:36 Using mentors and AI to scale smarter and faster
10:52 How AI automates content and creator approval
13:36 Purely White’s rise through Snapchat before pivoting to TikTok
16:45 How changes in algorithms nearly sank the business
19:17 What makes a good media buyer and how to track performance
22:26 Scripting influencer content and learning from audience behaviour
25:15 Street interviews and podcast clips as powerful ad formats
28:52 Getting copied by Gap and taking it as a compliment
32:11 Learning from global brands to prep for international expansion
36:10 Why Europe, UK, Canada and cold climates are next
39:34 What they look for in creators beyond follower count
42:05 Why talking on camera builds stronger consumer trust
47:09 TikTok Shops vs Meta for content and sales strategy
50:00 Testing blankets, tees, snack hoodies and what to avoid
53:25 Why top creators rarely leave to start their own brands
56:56 In-house hires over agencies and building a loyal team
60:00 What his day-to-day actually looks like as a founder
62:11 Scaling Nude while keeping focus on what’s working

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