pilot
(12)
Tyson Weihs and the art of a useful flight bag
A restaurant childhood, a dot-com lesson and a pilot’s eye for awkward software helped shape ForeFlight. Its co-founder and former CEO is still finding things to build.
Eric Zipkin and the art of taking the short way
He built Tradewind Aviation around journeys the big jets overlooked. His other flying life takes him across the Atlantic in aircraft that helped make history.
Matt Drozdzynski and the work of making work disappear
Before Plane could simplify payroll, its co-founder had to learn what a distributed team actually needed. Meetings, false starts and a formidable appetite for deleting things helped shape his answer.
Waseem Daher and the $400,000 promise
Before Pilot could earn a customer’s trust, Waseem Daher spent a third of its early funds on a name. The road to that decision runs through MIT, two acquisitions, and a stubborn belief that someone else should do the bookkeeping.
Raj Dutt
Raj Dutt is the co-founder and CEO of Grafana Labs, the company behind the open source dashboarding tool used by more than 25 million people. He previously founded and sold the hosting company Voxel to Internap, then co-founded Raintank in 2014 with Torkel Ödegaard and Anthony Woods and later rebranded it as Grafana Labs. In 2025 the company crossed $400M ARR with 7,000+ customers.
Ben Klein
Ben Klein is the CEO of Aero, the by-the-seat semi-private jet airline founded by Uber co-founder Garrett Camp and based at Van Nuys Airport in Los Angeles. A licensed pilot since high school and a former aviation litigator, Klein is unusual among airline chief executives: he not only runs the company but also flies its Embraer 135s and Legacy 600s as a certified first officer. He joined Aero as General Counsel in 2021, became President, and stepped up to CEO in September 2023, steering the carrier's consolidation around Los Angeles and its position in the gap between commercial first class and full private charter. He also teaches aviation law as an adjunct professor at San Jose State University.
Matt Pelc
Matt Pelc is the co-founder and CEO of Plane, the all-in-one people platform (formerly Pilot) that helps fast-growing startups pay and manage employees and contractors in 100+ countries. A Cambridge-trained computer scientist who got his start writing Ruby and building Slack bots, he went through Y Combinator's Winter 2017 batch and has spent the better part of a decade trying to make a worker's location irrelevant to whether a company will hire them.
Shimin Ooi
Shimin Ooi is the CEO of Sleep Reset, a virtual sleep clinic that pairs licensed clinical care with a proprietary CBT-I program to treat insomnia without sleeping pills. A Princeton graduate who built her career across McKinsey, Pilot, and Index Ventures, she now runs a company arguing that a lot of what people call burnout is really untreated bad sleep. In 2025 she took Sleep Reset's pitch to the HLTH stage and walked away with the AARP AgeTech After Dark prize.
Manu Sharma
Manu Sharma is the CEO and Co-founder of Labelbox, the leading AI data infrastructure platform that powers training data pipelines for frontier AI models. Born in Roorkee, India, he studied aerospace engineering at Embry-Riddle and Stanford before building CoPilot at DroneDeploy and leading data analytics at Planet Labs. In 2018, he co-founded Labelbox with former colleagues Brian Rieger and Daniel Rasmuson, raising $188.9M through a Series D led by SoftBank Vision Fund 2. Labelbox now serves as the command center for AI teams building and scaling production machine learning systems, from annotation and RLHF to evals and synthetic data generation.
Jeff Karras
Jeff Karras is a General Partner at America's Frontier Fund and co-founder of Alter Venture Partners, bringing over 20 years of venture capital experience to the intersection of deep tech, national security, and U.S. strategic competitiveness. With more than 40 investments and 23 exits - including 6 IPOs - he has backed companies spanning semiconductors, advanced manufacturing, synthetic biology, and AI. Before pivoting to frontier tech, he helped build SingTel Innov8's North American and Israeli operations and spent nearly a decade at Levensohn Venture Partners. A licensed pilot based in San Francisco, he is among a small cohort of investors who believe the most important technology companies of the next decade will emerge from the overlap of commercial innovation and government-scale problems.
Nathan Barry
Nathan Barry is the founder and CEO of Kit (formerly ConvertKit), a $45M+ ARR bootstrapped email marketing and creator platform serving 60,000+ creators. A former self-taught designer who dropped out of Boise State, Barry built ConvertKit from $0 to a $200M valuation without a dollar of venture capital, turned down a $200M acquisition from Spotify, wrote viral frameworks like 'The Ladders of Wealth Creation,' and is now building Kit as the operating system for the creator economy while also flying a Cirrus SR22T, farming, and investing in a historic ghost town.
Katie Mack
Dr. Katherine (Katie) Mack is a theoretical astrophysicist, science communicator, and author who holds the inaugural Hawking Chair in Cosmology and Science Communication at the Perimeter Institute for Theoretical Physics. Known online as @AstroKatie with over 400,000 Twitter/X followers, she studies the fundamental questions of how the universe will end - dark matter, vacuum decay, primordial black holes - and makes it all thrillingly accessible. Her 2020 book 'The End of Everything (Astrophysically Speaking)' was a New York Times Notable Book. She publishes 'The Last Star' newsletter, co-hosted a podcast with John Green, is an instrument-rated pilot, and was name-dropped by Hozier in a Grammy-winning album.