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Startup Ideas #447: Startup Syndicate, Smart Glasses...
Plus From 42 Rejections to building a $3.2B Business
Welcome to Half Baked, the newsletter serving up startup ideas as talked about as Meta’s buggy smart glasses demo yesterday 👀
If you want to read any previous editions of Half Baked, you can check them out on our website.
Let’s goooo 🚀
In today’s edition:
💡 Democratizing one of YC’s greatest attributes
📈 Did we just witness an iPhone moment?
🛠️ Using AI to generate cold outreach messages
🤑 From 42 Rejections to building a $3.2B business
🍻 A product to protect the sleepwalkers out there
💳 Startup Sales Syndicate
Mart to market
Available domain: Startmart.co
The Problem: YC Demo Day was last week, but unfortunately we didn’t get to go (I guess our invitations were lost in the mail…thanks Garry). Demo Day is an incredible opportunity for the hottest startups in the Valley to show off their progress and traction to investors. But interestingly, for a lot of YC companies, their early traction comes in the form of selling to other YC startups. Which makes sense right? They understand startup pain points, move fast, and aren't bogged down by enterprise procurement processes. Meanwhile, 67% of startups say finding their first 10 customers is their biggest challenge. It's time to democratize the YC startup ecosystem magic. Here’s how.
The Solution:
In a line: A marketplace where startups can discover, evaluate, and buy from other startups, creating a fast-moving ecosystem of mutual customer acquisition.
Product:
Companies create profiles showcasing their products with startup-specific pricing, case studies from other startups, and "built for startups" messaging.
The platform matches startups based on stage, industry, and needs, connecting a Series A SaaS company with the marketing automation tool they actually need.
Streamlined purchasing with startup-friendly terms, monthly billing, and no enterprise sales BS, just founders selling to founders who get it.
Founder-to-founder reviews, referral programs, and a "startup stack" showcase where companies share their entire tech stack publicly.
Business Model: Transaction fees (5% - 10% of each sale)
End Goal: Potential acquisition by accelerators like Techstars or 500 Startups, or by B2B platforms like G2 or Capterra at 10-15x revenue multiple as the startup economy continues to grow.
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👀 Founders: Don’t Enter BFCM Blind
Black Friday / Cyber Monday can drive up to 40% of your annual revenue — but the difference between winning big and scrambling comes down to how fast you can turn data into decisions.
That’s why Triple Whale built this: 50 AI-ready prompts crafted for scaling ecommerce brands.
Inside, you’ll get:
✅ Prompts to analyze and optimize every stage of BFCM
✅ Step-by-step workflows that save you hours
✅ Automation tips with Triple Whale’s Moby to keep you ahead in real time
Skip the guesswork. Copy, paste, and let AI do the heavy lifting this peak season.
👓 Are AI Glasses Having Their iPhone Moment?
The Trend: Everyone's been waiting for the "next big thing" after smartphones, and last night Meta just showed us what that could look like. At Connect 2025, Zuck and his entourage unveiled the Meta Ray-Ban Display glasses with built-in screens, plus second-gen Ray-Bans and Oakley sports glasses. Sure, the demos glitched a few times on stage, but Steve Jobs had plenty of demo fails on stage too. It’s the way these things go. The $799 price point puts these in reach of early adopters, and the Ray-Ban partnership means they actually look pretty slick. Is this a glimpse into the future? Or a short-sighted move by Meta. Time will tell…
Opportunities:
AI Glasses App Store: Build the ecosystem of apps specifically designed for smart glasses interfaces, focusing on hands-free, voice-controlled experiences.
Creator Tools for POV Content: A platform that optimizes short-form POV videos directly from smart glasses, auto-editing them for TikTok, Reels, or Shorts.
📤 Using AI to Generate Cold Outreach Messages
The Tool: Cold outbounding is a necessary evil in business, like posting cringey LinkedIn posts or begging your friends to support your Product Hunt launch. So if you’re going to send out cold emails or LinkedIn messages you may as well do it right. Here’s how.
Step-by-step:
Give your LLM as much context as possible on your business using this mega prompt
Then add this next prompt to your model (last one, I promise)
Put the messages into your LinkedIn or email sequencing software and start your outbounding
✍️ Start Writing Online in 2025 (Free Masterclass)
Writing and sharing your ides online is one of the highest leverage activities you can possibly do. Trust us…we’re speaking from experience here.
That’s why we’ve teamed up with our friends Dickie Bush & Nicolas Cole (over 600k followers combined) to invite you to their FREE live masterclass on Thursday, Sept 18th at 9 AM PST.
In 90 minutes, you’ll discover:
The biggest benefits of writing & sharing your ideas online (from helping 10,000+ writers).
The best platforms to start writing online in 2025 (so you can accelerate your audience growth).
How to generate your first 30 content ideas (so you can finally get started building an audience of loyal readers).
By the end, you’ll have the foundation to become a prolific digital writer and start monetizing your knowledge. Spots are limited, save yours now!
🧰 From 42 Rejections to Building a $3.2B Business
The Idea: Marco Zappacosta and Jonathan Swanson weren't your typical tech founders. Both Columbia and Yale grads respectively, they'd actually started their partnership in politics, co-founding a nonprofit called "Students for Saving Social Security" that grew to 10,000+ students across 300 college campuses. But after they both realized politics wasn't for them, they pivoted to tech. Along with their Yale Law School friend Sander Daniels, they spent weeks brainstorming startup ideas in 2008. The breakthrough came when they realized how broken the process was for finding local service providers - whether you needed a plumber, photographer, or personal trainer, you were stuck with Yellow Pages, Craigslist, or word-of-mouth. This was the idea for Thumbtack.
The Execution:
2008: Founded Thumbtack in San Francisco after moving from the East Coast. Initially operated like Craigslist with a manual matching process - customers would post job requests, pros would scan through hundreds looking for matches.
2008-2015: The early years were brutal. Jonathan recalls pitching to 42 separate investors and being rejected by every single one. Finally secured angel funding through Marco's mentor network.
September 2015: Raised $125M Series E, marking their breakthrough into major growth phase as the home services market began moving online.
2016-2017: Launched "Instant Matching" feature - a complete product pivot that automatically matched pros with suitable customers based on preferences, location, and availability. This solved the core inefficiency of their original model.
July 2019: Closed $150M Series F as the platform scaled to hundreds of thousands of service professionals across 1,000+ service categories.
June 2021: Raised massive $275M Series G at a $3.2B valuation. Revenue grew over 50% year-over-year with expectations to facilitate $2B+ in transactions annually.
July 2024: Secured $75M debt financing from Silicon Valley Bank and Hercules Capital to continue expansion in the $600B home services industry.
The Lesson? Sometimes great ideas and businesses take time to find their feet. The early years were brutal, but by going through them it made the founders and the business stronger.
🔍️ Founder Finds
🛠️ AI Tool: Notion just launched Notion Agents. This is big.
🚨 Raise Alert: Numeral just raised $35M to automate sales tax with AI.
📚 Must-Read: Ben Horowitz on when Steve Jobs went full founder mode (1 minute read)
🎙️ Must-Listen: Elon Musk interviews are always worth a listen (about tech at least). This is no exception.
💬 Founder Quote: "Play by the rules, but be ferocious." Phil Knight (Nike)
🔦 Reader Spotlight: Meet Pierre and Soham
What are you building? RAG for Internal CRM Database
How did you come up with the idea? Pierre spent countless hours digging through LinkedIn just to find the right people to network with for internships. That’s when he realized how broken internal search really was, so he built a RAG engine designed to surface the most relevant and precise leads instantly.
Biggest challenge right now? Right now, it’s all about scaling. Our pilot already spans 1M LinkedIn profiles, but the real magic is that this tech can plug into any system.
How can Half Baked readers help? If you’re in VC, sales, or recruiting, we’d love to talk. Our engine makes it effortless to source talent like “recent CS grad, experience in AI startups, skilled in XYZ” in seconds.
Connect with Pierre and Soham: Pierre on LinkedIn | Soham on LinkedIn
P.S: If you want your startup or project featured, click here!
🍺 Drunk Business Idea: Dream Leash
Ever wake up in the kitchen in the middle of the night with no memory of how you got there? Tired of your midnight self racking up steps you don’t remember taking?
Meet the Dream Leash™ - the world’s first leash designed for your unconscious wanderlust. Simply strap it to your leg and anchor it to your bedpost, preventing you from wandering into danger.
Dream Leash™ - because sometimes your dreams should be tethered to reality.
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👋 That’s All Folks!
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