Brent Chudoba is the CEO of Biteable, a remote-first video creation platform that has helped more than seven million people make studio-quality videos. He spent a decade as a senior operator (COO, CFO, CRO and GM roles) at some of the internet's best-known productivity companies including Calendly, Thrive Global, PicMonkey and SurveyMonkey, where he was employee number fourteen. Before operating, he was an investor at Spectrum Equity and an investment banker at Piper Jaffray. Today he also teaches a cohort-based course on Maven, Startup Leadership Unleashed, distilling what he learned scaling teams.
PostHog is an all-in-one, open-source developer platform that bundles product analytics, web analytics, session replay, feature flags, A/B testing, experiments, surveys, error tracking, a customer data platform, and a data warehouse into a single stack engineers can self-host or run in the cloud. Founded in 2020 by James Hawkins and Tim Glaser through Y Combinator, it lets product engineers track usage, ship features, and keep customer data in one place rather than stitching together a dozen SaaS tools. The company reached unicorn status in 2025 with a $75M Series E at a $1.4B valuation.
Jerry Connelly is the Chief Executive Officer of KeepingCount, a remote-first outsourced accounting and advisory firm that gives growing small businesses and nonprofits the bookkeeping, reporting, and fractional-CFO horsepower they usually cannot afford to hire in-house. Built around the promise of 'better numbers for growing businesses,' KeepingCount pairs platform technologies like Sage Intacct and QuickBooks Online with hands-on accounting teams serving construction, consumer products, professional services, real estate, life sciences, and vacation-rental clients. Originally headquartered in Boise, Idaho, the company now runs as a distributed organization, and Connelly leads it with a stated emphasis on values - conscientious, disciplined, gracious, integrity, and serving all clients.
Joseph Heller is the CEO and founder of THE/STUDIO, the company behind TheStudio.com and SuppliedShop.com, a supply-chain platform that connects creators, brands and small businesses with vetted factories worldwide so anyone can make custom products - patches, pins, apparel, medals and more - without minimum orders or sourcing expertise. After more than a decade working with factories in China, he built a low-MOQ, on-demand manufacturing model and a fully remote, globally distributed team, raising an $11M Series A in 2018 after 18 months and more than 150 investor rejections. His through-line is democratizing access to manufacturing as a path to broad-based wealth creation.
Aha! is a bootstrapped, fully remote software company that makes the world's most widely used product development tools. Founded in 2013 by Brian de Haaff and Chris Waters, its suite - Roadmaps, Ideas, Whiteboards, Knowledge, Discovery, Teamwork, Develop, and the newer AI-driven Builder - helps product teams set strategy, gather customer feedback, prioritize features, and ship work people love. It reached profitability without venture capital and is used by more than one million product builders worldwide.
Will Young is the co-founder and CEO of Sana, an Austin-based tech-enabled health plan that aims to cut small-business health insurance costs by up to 30%. A Stanford and Harvard Business School graduate who passed through Google and Justworks before starting a company in an industry he had no background in, Young bet that being an outsider was the advantage. Sana launched in 2018, went fully remote from day one against investor advice, and by its $60M Series B in 2022 had raised roughly $107M total while operating across eight states.
Close is a bootstrapped, profitable sales CRM built for small and mid-sized teams that want to spend less time on admin and more time actually selling. Founded in 2013 out of a San Francisco sales agency, it combines pipeline management, built-in calling, email, and SMS into one platform - no integrations required. With $17M+ ARR and a fully remote team across 40+ countries, Close has grown almost entirely without venture capital, making it one of the more unusual success stories in SaaS.
RemoFirst is an Employer of Record platform that lets companies hire, pay, and manage full-time employees and contractors in 185+ countries without setting up local entities. Founded in 2021 in San Francisco, it competes with Deel and Rippling by undercutting them on price - starting at $199 per employee per month - and handling payroll, taxes, benefits, equipment, and visas on its customers' behalf.
HiHello builds digital business cards, email signatures, virtual backgrounds, and contact management tools for individuals and enterprises. Founded in 2018 in Palo Alto by serial founder Manu Kumar (CardMunch, Carta) and Hari Ravi, the company turns the awkward exchange of paper rectangles into a tappable, shareable, trackable contact moment.