Join me as I chat with Andrew Wilkinson, Co-Founder of Tiny, as we discuss investment and startup ideas in the current AI landscape. We explore how AI is simultaneously lowering barriers to entry while increasing competition, making it easier to build "million-dollar businesses" but harder to create sustainable long-term ventures. We share specific startup ideas leveraging AI, including secure data integration platforms, automated web design services, and AI-powered lending.
Timestamps:
00:00 – Intro
01:13 – Business building in AI
08:01 – Media Business Opportunities and AI
18:05 – The future of GPT wrappers
21:07 – Automation and AI tools we use
29:01 – Startup Idea 1: MCP and Financial Analysis
34:36 – Startup Idea 2: AI Web Design Agency
36:54 – Startup Idea 3: Message Maxing
43:30 – Startup Idea 4: AI-Based Lending Solutions
49:30 – Andrew’s Stealth Startup
Key Points
• AI is making it easier to build businesses but harder to maintain competitive advantages as tools become widely accessible
• Distribution, data advantages, and network effects are becoming the primary moats in the AI era
• Media businesses with high-value niches present opportunities for entrepreneurs to build audiences before layering AI tools
• Secure AI applications (particularly around financial data and personal communications) represent potential sustainable business models
1) The AI Paradox: It’s never been EASIER to build a $1M business, but never HARDER to build sustainable value.
Why? Because anyone can "vibe code" your product in a weekend.
Distribution and network effects are the new moats. Tools alone won’t cut it anymore.
2) Where are the ACTUAL opportunities?
Andrew & Greg agree: Buy or build MEDIA businesses first, then layer AI on top.
• Focus on High-value niches not mass audiences
• Build community BEFORE tools
• Example: Buy TechCrunch or event series like South by Southwest
3) AI tools they’re actually using RIGHT NOW:
• Gumloop – For sales lead intelligence
• Lindy – Email processing & calendar management
• Manus AI – For candidate screening (saved Andrew hours!)
• Vercel V0 – Rebuilt Andrew’s pressure washing website in 30 SECONDS
4) Startup Idea 1: "Secure MCP"
Model Context Protocol (MCP) lets LLMs access your data securely.
Andrew built a custom system to analyze his company finances across multiple businesses.
Opportunity: Build the "1Password of MCP" – where security is the selling point.
5) Startup Idea 2: "Message Maxing"
An app that analyzes your text messages to identify:
• Which friends exhibit toxic traits
• How YOU come across in messages
• Who you’re neglecting
Perfect for viral TikTok marketing. Could be the next CalAI!
6) Startup Idea 3: AI-powered web design agency
• Use V0 to auto-redesign ugly local business websites
• Reach out with "I already built you a better site"
• Charge $500 + $20/mo hosting
• Scale with automation
Low-hanging fruit for your first million!
7) Startup Idea 4: "Bank of Vibe Coding"
AI-powered lending platform for vibe coders:
• Quick approval for developers with traction
• Take % of profits instead of interest
• Criteria: X followers, Stripe integration, etc.
Sahil Lavingia’s $100K offer proves demand!
8) The BIG question: Are these Cal AI businesses (make $1M then die) or sustainable?
Andrew’s take: "Almost all these businesses will be zeros in 5 years."
Greg’s counter: "It’s so hard to predict even 5 months from now!"
What do YOU think? Are you building for the short or long term?
The MOST VALUABLE insight: The businesses that are easiest to start are often the worst businesses to be in long-term.
But that doesn’t mean you shouldn’t start one! Making your first million with a "Cal AI business" is still a win.
Notable Quotes:
"It’s never been easier to build a million dollar business and it’s never been easier to lose all your equity value." – Andrew
"Distribution is the new moat, anyone could create anything." – Greg
LCA helps Fortune 500s and fast-growing startups build their future – from Warner Music to Fortnite to Dropbox. We turn ‘what if’ into reality with AI, apps, and next-gen products https://latecheckout.agency/
BoringAds — ads agency that will build you profitable ad campaigns http://boringads.com/
BoringMarketing — SEO agency and tools to get your organic customers http://boringmarketing.com/
Startup Empire — a membership for builders who want to build cash-flowing businesses https://www.startupempire.co
FIND ME ON SOCIAL
X/Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
LinkedIn: https://www.linkedin.com/in/gisenberg/
FIND ANDREW ON SOCIAL
X/Twitter: https://x.com/awilkinson
Never Enough: https://www.neverenough.com
Tiny: https://www.tiny.com
