Own Pain Startups

dbt Labs built the de facto standard for data transformation in the modern data stack, growing to 20,000 weekly users through a powerful combination of open-source product leadership and community-driven distribution. Starting as Fishtown Analytics consulting firm for nearly two years, the founders learned customer pain points firsthand before productizing dbt as an open-source tool with a proprietary cloud offering, achieving viral adoption through word-of-mouth and ecosystem integration.

Duarte Incorporated, founded by Nancy Duarte, has become the world's leading presentation design and storytelling agency, having crafted over 250,000 presentations for iconic brands including Apple, Google, TED, the World Bank, and Al Gore's groundbreaking 'An Inconvenient Truth.' The company pioneered modern presentation design in the early Macintosh era and continues to help Fortune 500 companies and world leaders master the art of persuasive communication through story structure, empathy-driven design, and visual clarity.

Spotify is a music and podcast streaming platform founded in 2008 that pioneered the shift from curation to algorithmic recommendation to generative AI. Under Gustav Soderstrom's 14+ year tenure as a product and technology leader, the company evolved from a desktop application to a global platform with half a billion users. Spotify's major innovations include Discover Weekly, personalized recommendations, and recently AI DJ—a generative product that couldn't exist without AI.

SpeakUp is Matthew Dix's storytelling and public speaking coaching company that works with individuals and corporate teams at companies like Slack, Amazon, Lego, and Salesforce. Dix, a 59-time Moth Story Slam winner and elementary school teacher, teaches a methodology centered on identifying the five-second moment of transformation or realization that defines every good story, then using specific narrative techniques (stakes, surprise, vulnerability) to make stories memorable and impactful in both personal and business contexts.

Gojek is a Southeast Asian super app that started as a motorcycle ride-hailing service in Indonesia and evolved into a comprehensive platform offering 30+ services including ride-hailing, food delivery, grocery delivery, payments, and financial services. By the time of their IPO (Indonesia's largest ever at ~$27-28B valuation), Gojek had 2.7 million drivers, completed 3 billion orders annually, and dominated the region through early investment in brand, operational excellence, and solving uniquely local problems that global competitors overlooked.

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.