ChatGPT Startups

Cal AI is an AI-powered calorie tracking app built by 18-year-old Zach Yedegar and three co-founders. Launched in May 2024, it generates approximately $24M in annualized revenue (with $2M in the most recent month), making it one of the fastest-growing consumer apps. The team grew through strategic paid influencer partnerships on Instagram and TikTok, achieving 90% AI accuracy on nutritional scanning while bootstrapping the entire operation with capital from Zach's previous venture.

Do Anything is an AI-powered autonomous agent platform that executes tasks without explicit prompts. The founder Garrett created it as a side project while building Pipe Dream, demonstrating the capability to analyze YouTube channels, create content plans, generate presentations, and handle complex workflows automatically through natural language requests.

How I AI is a new podcast launched under the Lenny's Podcast Network, hosted by Clairvaux, an AI-obsessed product leader and founder. The show features practical demonstrations of how people use AI tools like V0, Devin, and Cursor to ship faster and improve workflows, with live screen sharing and 30-minute episodes. The inaugural episode features Sahil Lavengia, CEO of Gumroad, showcasing how AI tools are enabling 40x speed improvements in feature development and driving cultural change in engineering organizations.

Tiny is a holding company founded by serial entrepreneur Andrew Wilkinson that has grown to ~$300M in revenue by acquiring and holding profitable businesses long-term, inspired by Warren Buffett's philosophy. Rather than starting companies, Wilkinson learned to buy established businesses with strong moats (network effects, brand loyalty) and leave them largely unchanged. The company owns 40+ businesses including Dribbble, Letterboxd, Serato, and Aeropress, demonstrating that bootstrap companies can scale massively without VC funding.

SweetCX360 is a 15-year-old customer experience design and diagnostics company founded by Valerie Peck that blended consulting services with SaaS revenue. Starting from $708,000 in pure SaaS ARR, the company was bootstrapped and grew 10-20% annually while maintaining optionality. In October 2022, QuestionPro acquired the company for a $3 million headline price (structured as an installment sale over three years), with Valerie transitioning to lead a global consulting practice under the parent company while the software side is managed by VP of Sales Mark Mandel.

CJ built Mostly Metrics, a newsletter for CFOs launched in December 2020, starting from zero subscribers by obsessively engaging on Twitter around relevant keywords and partnering with B2B companies like Ramp and Brex. The newsletter grew to 35,000 subscribers (7,000 of whom are actual CFOs) in 1.5 years with a 46% open rate and 5-7% click-through rate, attracting sponsorships of $5-10k per post and up to $100k for bundled deals. He also launched a podcast called Run the Numbers with Turpentine Network while maintaining his full-time role as CFO at Parts Tech, planning to transition fully to media within three years.

Das-services.com is an AI training and automation company founded by Aaron Vitas that helps mid-market tourism, retail, service, and real estate businesses implement AI solutions. The company operates a hybrid model combining high-ticket services (AI Maximizer, Das Training) with SaaS products (Das Hub and Das Content Manager). With combined revenue projected at $500K+ for the year and the content manager generating $179/user/month with 218 people on the waitlist, Das is scaling rapidly just 8 weeks after SaaS launch.

PlumbElec Marketing is a marketing agency founded by Tom Richards that specializes in serving plumbing and electrical contractors. Operating from Bali, Tom has grown the agency to $57K MRR ($684K ARR) through a niche focus on trade businesses and a lean, profitable model emphasizing Google Maps local SEO and cold outreach strategies.

Khanmigo is a new learning platform built by Sal Khan at Khan Academy that uses generative AI technology from OpenAI's ChatGPT to help students with their schoolwork. The platform aims to act as a personal tutor for every student and a teaching assistant for every educator, potentially reshaping education in the post-COVID era.

eva.ai is an enterprise customer support solution launched 5 months ago by Valvis Brogas and co-founder Zeno, with a team of 6 people. The bootstrapped startup uses AI to reduce customer support costs by up to 97% and deliver responses in 10 seconds or less. They're about to launch their first two paid pilots: one with a $5,000 flat fee upfront and another at $149/month, targeting e-commerce, travel, and hospitality industries.