Own Pain Startups

Easy Ear Training is a business founded by Christopher Sutton who documented the emotional challenges of starting a company in a blog post. Sutton found support and community through the Tropical MBA podcast and its Dynamite Circle community of listeners, which became instrumental in helping him navigate the entrepreneurial journey.

Voyagu is a two-sided SaaS platform connecting travelers and travel agents, operating as "the Uber of travel." Founded by Ivan Saprov during the pandemic, the company spent $600k and 18 months building its backend, search engine, and platform, achieving a 54% repeat booking rate by Q3 2023 through strong product-market fit and word-of-mouth growth. Voyagu uses ML technology and targets 1 billion in gross annual bookings by solving the speed and competitiveness gap travel agents face against DTC platforms.

PubLoft was a marketplace connecting writers with companies seeking managed blog services at $2,000/month subscription. Mat Sherman grew it from $0 to $24K MRR in 7 months using cold email outreach and personal sales, securing a $100K investment from Jason Calacanis. The company ultimately failed due to loss of key clients, reckless spending post-funding, and misalignment with co-founder Jeremy on strategic priorities.

Observa was a security SaaS tool built by Rob Picard after leaving Robinhood to join Y Combinator in 2020. Over 10 months, Rob pivoted through three different product ideas (intrusion detection, botnet IP sharing, and public database exposure detection) but ultimately failed to achieve product-market fit, generating no revenue before shutting down in September 2021 after raising $462,000.

WePlate was a B2B SaaS nutrition platform that used an algorithm to recommend specific meals and portion sizes to college students and help universities optimize cafeteria menus. After 8 months of development and contacting nearly 100 universities, founder Alex Hu shut down the company when it became clear that colleges weren't interested in a product that didn't directly improve their bottom line, and students prioritized studying over diet optimization.

BaseTemplates is a SaaS platform selling pitch deck templates, financial model templates, and custom pitch deck design services for startup founders. Founded in 2019 after acquisition, Maximilian Fleitmann grew the business from hundreds of dollars per month to over 5 figures monthly through content marketing, free tools, and strategic partnerships. The company has become a key resource in the founder and VC ecosystem without spending any money on traditional marketing.

Claude Code is Anthropic's AI-powered coding assistant that grew from a terminal prototype to generating 4% of public GitHub commits with daily active users doubling last month. Built by Boris Cherny, the tool represents a fundamental shift in how developers work, with companies like Spotify reporting their best developers haven't written code since December. Claude Code exemplifies product-led growth driven by demonstrable productivity gains and latent demand for AI-assisted development.

BusyMind was a silent meditation app built by Kevin Lamping to enable mindfulness practice in busy environments without audio distractions. The app achieved about 5 purchases per month but ultimately failed due to Kevin's inability to dedicate sufficient time to marketing and growth while maintaining his full-time job. Kevin's core learning was that lack of time and financial runway, rather than market rejection, was the primary cause of failure.

Campertunity is a peer-to-peer camping marketplace that launched in Canada in 2018, introducing camping to the shared economy. Founded by Nora Lozano, an engineer with a passion for nature, the platform allows landowners to list private land for camping and campers to book sites. After generating significant pre-launch media attention, the company grew through organic PR and Facebook community engagement, reaching 400+ users and 50 listings within its first year.

Nick O'Hara quit his $130,000/year engineering job at Wayfair to build Canary, a mobile app connecting venues with musicians for booking live gigs. After initial failures with cold calling, he pivoted to in-person sales and won a local startup competition. As of February 2019, he was raising $150,000 and generating $10k-$25k/month in revenue through direct venue outreach.

Career Sidekick is a job search advice website founded by Biron Clark in 2013 that grew from a failed, unfocused blog into a multiple six-figure annual revenue business by niching down to focus exclusively on job search content and prioritizing organic search optimization. The business generates revenue through a mix of products (courses and e-books), affiliate marketing, and display advertising (via Mediavine), with 85%+ profit margins and over 1 million monthly visitors, 80% of which come from organic search. Biron bootstrapped the operation, remains the only full-time employee, and operates it as a fully remote, location-independent business while traveling.

Chowdy was a Toronto-based subscription meal delivery startup that grew to $1.3M in annual revenue in 2 years by solving the last-mile delivery problem through a unique hub system using partner cafes. The business reached approximately $100,000-$125,000 per month in revenue but ultimately shut down due to regulatory pressure from the Toronto health department, which deemed their distribution model too risky, combined with unsustainable unit economics and high customer churn.

Circle is a white-labeled community platform built by three ex-Teachable employees (Andrew Guttormsen, Sid, and Rudy) who identified an unmet need: creators had tools to host content but not to build engaged communities. Starting as a side project in early 2020, they built an MVP in one month, grew a waiting list of thousands through a landing page and survey, and achieved #1 on Product Hunt at launch in August 2020—generating as much revenue in one month as in the prior six months combined. The company raised $5.5M and was adding hundreds of customers per month by December 2020.

Community Coders was a marketplace that connected high school students seeking work experience with local businesses needing web development and digital marketing services. Founded by Kaito Cunningham in 2018, the company generated approximately $20,000 in revenue against $35,000 in expenses before shutting down after 2 years (1 year full-time, 1 year part-time). The business failed due to lack of product-market fit, inability to sustainably acquire customers, team misalignment, and Kaito's inexperience in leading the venture.

Huberman Lab is a free educational podcast and content platform launched in January 2021 by neuroscientist and Stanford professor Andrew Huberman. Within 10 months of launch, the channel became one of the top 10 most popular podcasts globally, with the first video reaching 652,000 views and subsequent videos hitting 1+ million views. The growth was driven by consistent weekly content, word-of-mouth from major podcast appearances, and a commitment to free, science-backed health and wellness education.

Atomic is a startup studio founded by Jack Abraham (who previously sold Milo to eBay for $75M at age 24) that creates multiple companies per year by identifying real problems across his portfolio and personal experiences rather than brainstorming. The studio has generated numerous successful exits and companies like Hymns (now public), Bungalow, Homebound, and Replicant, operating across healthcare, PropTech, FinTech, education, AI, and marketplaces. The studio is strategically selective, launching only 10-12 companies annually despite maintaining a list of 600+ potential ideas.

Inward is a breathwork app built by Robbie Bent, a former crypto investor and Ethereum community organizer who pivoted to wellness after making significant wealth in crypto. The app modernizes ancient breathwork techniques with guided sessions and music, designed to scale the in-person facilitated experiences that were booking out his Canadian garage 24/7. Early traction shows strong adoption with daily active users, positioning breathwork as the next major mental fitness category alongside SoulCycle and hot yoga.

Ben & Jerry's was founded in 1978 by two former friends who met in PE class as poor runners and reunited when one was rejected from medical school. Starting with a $5 ice cream making course and $12,000 in seed funding, they initially struggled in their Vermont shop during winter but pivoted to selling pints directly to restaurants and convenience stores. When Pillsbury strong-armed distributors to drop Ben & Jerry's in favor of their Haagen-Dazs brand, the founders turned adversity into their greatest marketing opportunity, launching the viral 'What's the Dough Boy Afraid Of?' campaign that generated massive PR, consumer awareness, and growth.

Behance was a portfolio platform for creative professionals that Scott Belsky bootstrapped for five years before raising venture capital. The company was eventually acquired by Adobe after seven years total. Scott's philosophy focused on obsessing over the first-mile user experience and understanding the psychology of creative professionals, which shaped the product's design and positioning.

1-800-GOT-JUNK is a junk removal and hauling service founded by Brian Scootamore in 1989 with a single $753 truck. Over 30 years, Brian built it into a nearly half-billion dollar franchise business across multiple home service brands through strategic PR, vision boards, and a relentless focus on hiring optimistic, customer-focused people. The company overcame major setbacks including a $40M revenue drop during the 2008 financial crisis, but recovered through leadership changes and long-term commitment to the core business.