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Startup Ideas #395: Reverse Mentorship, Micro-retirement...

Plus Turning a Magazine into a $1.6B Exit

Welcome to Half Baked, the newsletter serving up startup ideas as surprising as bookshop.org attacking Jeff Bezos (wasn’t on our 2025 bingo card) 🤔 

If you want to read any previous editions of Half Baked you can on our website.

Let’s goooo 🚀 

In today’s edition:

  • 💡 Turning the mentorship model on its head

  • 📈 The newest Gen Z term you need to know

  • 🛠️ The Lovable cheat sheet for 10x better development

  • 🤑 Turning a magazine into a $1.6B exit

  • 🍻 The ultimate wedding attire to keep you cool

🧑‍🏫 Reverse Mentorship Platform

TeachTok

Available domain: Zensei.ai

The Problem: Harry had Dumbledore. Daniel had Mr. Miyagi. Jesse had…eh Walter White (questionable, but still). The mentor-mentee dynamic is a time-tested trope in film and in business too, where the wise elder shapes the raw potential of the student. But today, the script has flipped. In today’s fast-moving world it's Gen Z who hold the keys in areas like ChatGPT hacks, TikTok virality, or decoding digital culture. At the same time 56% of Gen X and over 75% of Boomers feel left behind in the digital age. We think there’s a business in flipping the mentorship model on its head. Here’s what we’re thinking.

The Solution:

  • In a line: A reverse mentorship platform where Gen Z teaches older generations AI, tech, and viral culture.

  • Product:

    • 👋 Users sign up based on what they want to learn (older user) or teach (Gen Z mentor)

    • 🧠 The platform matches older users with Gen Z mentors based on learning goals (e.g. “Learn how to use ChatGPT,” “Understand TikTok virality”)

    • 📹 One-on-one or group sessions take place via integrated video calls and screen sharing

    • ⭐ After sessions, users can rate their mentor, leave reviews, and book follow-up calls.

    • 🔗 Check out the demo

  • Business Model: Mentees pay mentors per session, the platform takes a cut of their earnings

  • End Goal: Sell to an edtech platform (like MasterClass, Coursera, or Outschool) for a 5–8x revenue multiple.

Rate this idea:

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😵 Bad Passwords Kill Startups

As a founder, you're used to taking risks. But some risks just aren’t worth it - like leaving your company exposed to weak or reused passwords.

That's because just one leaked password can nuke your business. It’s not worth the risk.

That's why smart teams (and even dumb teams like ours) use 1Password, the industry leader in password management. It keeps your credentials safe, your team in sync, and your business protected.

Take big swings with your product, not with your security.

🏝️ Micro-retirement

The Trend: Overemployment. Quiet quitting. It feels like there's a new piece of Gen Z jargon minted every week. Today’s phrase? “Micro-retirement.” According to LinkedIn wisdom, this means taking a 1-2 week break from work every 12 to 18 months. So… a vacation. But while it’s easy to clown on the term, it actually points to a broader Gen Z shift: a growing prioritization of travel, rest, and time off, not just burning out for that next promotion. So while the buzzwords are cringe, the underlying trend is still important.

Opportunities:

  • Sabbatical Funding Marketplace: A platform where people crowdfund their micro-retirement or exchange future work output for funding.

  • Micro-Retirement Planner AI: An AI that crafts custom sabbatical plans based on your burnout level, finances, and bucket list.

📄 The Lovable Cheat Sheet for 10x Better Development

The Tool: You’ve all heard of Lovable by now, but most people don’t really know how to build apps properly on Lovable. Well earlier this week a Lovable employee shared his top tips for getting the most out of the platform. Here they are.

Step-by-step:

  1. Go to Lovable and get ready to start prompting

  2. Go here and check out the cheat sheet (easier to read version)

  3. Pick an idea (could be your own or a Half Baked idea) and start building

⏳️ It’s Never Too Early to Start

Dorm rooms. Middle school classrooms. Garage workbenches.

That’s where these businesses began:

  • Healthy Roots Dolls - now in Target, backed by Procter & Gamble

  • Royalty Soaps - a soap empire with nearly 1M YouTube subs

  • Bearbottom - an ethical menswear brand that’s donated 700K+ meals

  • Mo’s Bows - a handmade bowtie brand started at age 9, now seen on Shark Tank

Some of these founders stayed in school. Others dropped out. Some raised capital. Others bootstrapped. But they all used Shopify to build something real.

Start your store with a 3-day free trial, then it’s just $1/month for your first 3 months.

👗 Turning a Magazine into a $1.6B Exit

Back in 2011, Italian entrepreneur Simon Beckerman was running PIG magazine when he noticed something…young people didn’t just want to read about fashion, they wanted to sell it and express themselves through it. Traditional marketplaces like eBay felt cold and outdated. So he decided to build a dedicated, mobile-first, social shopping app where style, identity, and community came first. This was the beginning of Depop.

The Execution:

  • 2011: Launched Depop inside PIG magazine in Italy as a way for readers to buy featured products.

  • 2012: Depop was spun out into its own company and moved HQ to London to tap into youth fashion culture.

  • 2013: MVP officially launched, looked and felt like Instagram but for selling clothes.

  • 2014–2016: Organic growth came through community events, campus reps, and seller fandoms.

  • 2016: Raised an $8M Series A from Balderton Capital, Maria Raga joined as CEO.

  • 2019: Raised a $62M Series C led by General Atlantic. Depop hit 13M users and expanded aggressively in the US.

  • 2020: Pandemic and TikTok “Depop hauls” drove huge growth.

  • 2021: Acquired by Etsy for $1.625B to double down on Gen Z resale.

The takeaway? No two founder stories are alike. We’ve covered hundreds of founder stories, none of them spun out from a magazine. So go and start writing your own story.

🔍️ Founder Finds

  • 🛠️ AI Tool: This site has a super cool, free logo generator for founders.

  • 🎁 Free Resource: HubSpot is still giving away 3 months of Perplexity Pro to our readers for free, get it while you can

  • 📰 Headline: Jack Dorsey just launched a new messaging app (with a pretty questionable name…)

  • 📚 Must-Read: “On the Life and Death of Y Combinator Startups”. Cool stats in there.

  • 💬 Founder Quote:I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not trying.” Jeff Bezos, Amazon

🔦 Reader Spotlight

  • 📚 ReadHero - Dennis is building an AI-powered app to track reading, take notes, and stay motivated with streaks.

  • 🔗 Linkero - Marcel Cruz is creating a drag-and-drop platform to build high-converting pages in minutes.

  • 🎥 CastBunny - Gary Pon is building tools for creators, including peer-to-peer streaming that cuts bandwidth costs.

  • 🌐 GoBrunch - Richard Lowenthal is running a virtual platform to host meetings, events, and grow communities.

  • 🎉 Flowtrip - Daniel Ko is making group trip planning fun and simple, from parties to festivals.

P.S: If you want your startup or project featured, click here!

🍺 Drunk Business Idea: Cold Tux

  • Have a few weddings in the calendar this summer? Struggling to keep your cool in the summer heat in your classic tux?

  • Introducing the Cold Tux™ - a limited-edition suit engineered by Coors Light to keep you as cold as the beer you're holding. It's sleek. It's stylish. It’s everything you need.

  • Cold Tux™ - because chilling at 34° shouldn’t just be for beverages.

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👋 That’s All Folks!

Before you go just a few public service announcements:

  • Have an idea you want feedback on? DM me to discuss it or book in for Office Hours here.

  • Looking to sponsor Half Baked? Just fill out this form and we’ll get back to you asap.

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See you soon,

John and Darragh | The Half Baked Team

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