Own Pain Startups

The Browser Company, founded by Josh Miller and Hirsch, builds Arc, a web browser focused on optimizing for user feelings rather than pure metrics. The company has grown at over 10% week-over-week for eight months, maintaining D5D7 (Daily Active Users using the product 5+ days per week) retention in the low-to-mid 30s to low 40s range. The company culture emphasizes heartfelt intensity, assuming you don't know, and celebrating team members publicly to rebuild trust in tech companies.

Outpace, founded by Ravi Mehta (former CPO at Tinder, Product Director at Facebook, VP Product at TripAdvisor), is a coaching platform designed to make expert-driven coaching more accessible. After spending 18 months as an entrepreneur-in-residence at Reforge helping build product leadership and strategy programs, Ravi identified a gap: while many learning resources exist (podcasts, blogs, cohort courses), one-on-one coaching remains largely inaccessible. Outpace combines product design, systems, content structure, and AI to scale expert coaching.

All the Hacks is a top-tier business podcast launched by Chris Hutchins, a former PM and founder who left Wealthfront to pursue content creation full-time. The podcast explores financial optimization, travel hacks, and life improvement through interviews with interesting people. In 18 months, it reached top 5-10 in business podcast rankings through authentic content, guest curation, and consistent weekly releases.

Bravado is a community-driven SaaS platform for B2B tech salespeople with over 300,000 members, including 50,000 VPs of Sales/CROs, 150,000 account executives, and 40-50,000 SDRs. Through its Seller Portfolio product (a real-time quota tracking tool similar to Mint.com for sales) and War Room community feature, Bravado provides benchmarking data on sales performance across the industry. In the current market downturn, Bravado is helping sales teams and founders rethink their go-to-market strategies, comp plans, and retention focus.

Gergé Oros is a former Uber engineering manager who left his $320-330k compensation package to build The Pragmatic Engineer, a paid newsletter on Substack about software engineering. In under a year, the newsletter grew to 189,000 subscribers (with 80,000 added in the last 90 days) and now generates more revenue than his former Uber salary, with subscribers paying for in-depth weekly content.

Barbara Gago is building Pando, an opinionated employee progression platform designed to replace traditional performance reviews. Drawing on her experience as CMO at Miro (where she helped create the visual collaboration category) and VP Marketing at Greenhouse, she's applying lessons in category creation, branding, and opinionated software design to address systemic bias in how companies evaluate and progress employees.

ProductPad is a SaaS tool for product managers built by Jana Basto to help teams organize roadmaps, OKRs, ideas, and feedback. Jana is also the co-founder of Mind the Product, the world's largest community of product people, and invented the popular Now, Next, Later roadmapping framework. The tool actively helps teams become better product managers by enforcing discovery, measurement, and thoughtful product practices.

Irrational Labs is a behavioral science consulting firm founded by Kristen Berman and Dan Ariely in 2013 that helps companies like Google, TikTok, Microsoft, LinkedIn, and PayPal improve product engagement and user behavior through applied behavioral economics. The company works with hundreds of clients using their proprietary "Three B's" framework—identifying specific behaviors to change, reducing barriers (logistical and cognitive), and highlighting immediate benefits—achieving measurable results like 24% reduction in misinformation sharing on TikTok and 20% increase in appointment bookings for One Medical.

Starter Story is a content platform that interviews and profiles founders running businesses generating $10K-$100K+ monthly revenue. Founded by Pat as a side project in 2016, it grew to include a blog with case studies, YouTube channel, community, and products by requiring founders to publicly share their revenue numbers. HubSpot acquired the company, with the deal expected to close around the time of this interview.

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.

Tommy Mello built A1 Garage Door from a side hustle painting garage doors into a $300M+ revenue business operating across 23 states and 37 markets with 25,000 jobs per month. Starting in 2007 with cold calls to local contractors, he scaled through ruthless focus on brand, systems, and marketing spend ($4.3M/month), transforming from a scrappy hustler into a systems-driven leader. The business is now valued north of $1.7B after a partial exit.

Foam Party Hats is a novelty merchandise company founded by Grace and Manuel Rojas that creates custom foam hats for events and sports occasions. The company gained massive viral traction when Chicago Bears wide receiver DJ Moore wore a custom cheese grater hat (a play on Green Bay Packers' cheese heads) during a post-game celebration that went viral with 2.2 million views, resulting in 10,000 orders in a week (~$500k in revenue). The founders appeared on Shark Tank and secured $100k for 25% equity.

DeepMind is an AI research company founded by Demis Hassabis to develop artificial general intelligence. Starting with game-playing AI that learned from minimal instruction, the company achieved landmark breakthroughs including AlphaGo defeating world Go champion Lee Sedol with unprecedented move 37, and AlphaFold solving the 50-year protein folding problem in one year, reaching 90% accuracy and enabling revolutionary drug discovery.

John Morgan built Morgan and Morgan into one of the largest personal injury law firms in the country by pioneering advertising in the legal industry when it was taboo. Starting from a personal mission to help injured people, he scaled the firm to ~$2B in revenue through innovative marketing, brand building ("for the people"), and creating a network of referral partners. Beyond law, he's built a portfolio of entertainment attractions including Wonderworks, Alcatraz East, and now Flavor Town, generating significant cash flow.

Jesse Cole built the Savannah Bananas from a struggling college summer baseball team in Gastonia (200 fans, $268 in the bank) to a billion-dollar entertainment phenomenon with a multi-million person waitlist and 10x more TikTok followers than the New York Yankees. By obsessively studying entertainment pioneers like Walt Disney, P.T. Barnum, and Bill Veeck, he completely reimagined baseball as a fan-first entertainment experience, introducing innovations like all-inclusive ticket pricing, banana ball (a new sport format), and elaborate on-field entertainment that turned skeptics into devoted fans.

Jamie Siminoff built Ring, a WiFi-enabled smart doorbell with a camera, starting from a personal problem he couldn't hear his doorbell. The company grew to $480 million in revenue by 2017 with triple-digit growth rates, despite being cash-flow negative due to rapid scaling. After nearly losing the deal to Amazon due to an ADT lawsuit injunction, Siminoff settled the suit, and Amazon acquired Ring for $1.15 billion in December 2017, just weeks after the legal cloud lifted.

Savannah Bananas is a baseball entertainment company founded by Jesse Cole that revolutionized the sport by creating 'Banana Ball'—a fan-first experience with modified baseball rules, capped 2-hour games, flat $25 ticket pricing (taxes included), and constant entertainment innovations. The company grew from nearly bankrupt beginnings to an estimated $70-100M in annual revenue with 2M+ fans annually, a 3M-person waiting list, and more social media followers than all MLB teams combined.

Tommy is a solo distressed investing operator who specializes in buying bankruptcy claims—particularly in cryptocurrency—at steep discounts and waiting for payouts. Starting with a small hedge fund buying Mt. Gox claims in 2014 for ~$80 per Bitcoin and eventually realizing 40x+ returns, he's built a lifestyle business operating from low-cost jurisdictions, partnering with institutional firms on larger deals while personally compounding capital at 30-50% annually through claims work and selective deep-value positions.

Mobile Emissions is a service that brings vehicle emissions testing to customers' homes for $50-60, eliminating the need to visit mechanic shops. The founders were getting most customers from organic Google search but had dismissed paid Google Ads after a poorly-tracked initial attempt with free credits. The business had opportunity to significantly scale by properly executing Google Ads and optimizing their value proposition on their website and Google Business Profile.

Touchland transformed hand sanitizer from a commodity product into a luxury item by applying premium design, fragrance, and limited collaborations (Hello Kitty, Disney). The founder raised $67,000 on Kickstarter, achieved $1M in first-year revenue, and experienced explosive growth during COVID-19. Recently acquired for $880M with projected $130M annual revenue.