gig-economy
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Dustin Walsey Learned Insurance From the Back Seat
Before Buckle became a fronting platform for MGAs, its idea was tested one ride at a time. Dustin Walsey’s route from Atlanta newspaper kid to insurance CEO is a study in listening closely, explaining simply and learning where the old categories fail.
Shirley Romig
Shirley Romig is a consumer, technology and operations executive with more than two decades of experience across the full company lifecycle. She is Chief Operating Officer at Techstars, the global pre-seed accelerator, after joining as Chief Accelerator Investment Officer in late 2023. Before that she co-founded and ran Mixo, a video platform for global food creators, and held senior operating roles at Lyft, Equinox, SapientRazorfish and Saks/Hudson's Bay, where she led omnichannel transformation. She sits on the boards of Lovesac and Mama's Creations.
Yong Kim
Yong Kim is the co-founder and CEO of Wonolo, an on-demand staffing marketplace that connects businesses with more than one million frontline workers across the United States. Born in Seoul, he moved alone to a New Hampshire boarding school at 15, graduated as valedictorian, and went on to the University of Chicago and Harvard before a career in tech investment banking at Deutsche Bank. A stint at a Coca-Cola innovation accelerator exposed the broken state of hourly staffing and led him to launch Wonolo in 2014. The company has raised roughly $200 million, including a Sequoia-led round, and Kim has become a prominent voice for treating gig and hourly workers with dignity, flexibility, and fair pay.
Mike Shebat
Mike Shebat is the co-founder and CEO of Traba, a New York-based labor marketplace that supplies vetted on-demand workers to warehouses, distribution centers, and light industrial employers. He started the company in 2021 after seeing, from inside a McMaster-Carr shipping floor and later Uber Eats, how often temp workers simply don't show up. Traba has raised roughly $46 million from Founders Fund and Khosla Ventures, and Shebat, a Forbes 30 Under 30 honoree, runs it on a famously intense in-office schedule.
Nick Abramovich
Nick Abramovich is the CEO of Workers Benefit Fund, a New York-based benefits platform that builds the plumbing between gig workers, freelancers, independent contractors and the government, union and private benefits they are eligible for but almost never enroll in. He has been running the company since 2019, when WBF acquired BeneStream, the Medicaid-for-the-workplace outfit he ran as President. Under him, WBF added Upward Finance in December 2024, extending the platform from healthcare enrollment into tax and earnings tools for gig workers. Before benefits, he was CEO of Synaptic Digital and CMO of Ditech Holding Corporation, with earlier stops at MetLife, MoveOnIn.com, and BizSlate. Columbia MBA, Tulane BS.
Jason Chicola
Jason Chicola is the founder and CEO of Rev, the Austin-based speech-to-text company that pairs 50,000 freelance transcriptionists with best-in-class AI to turn spoken words into searchable text. An MIT-trained engineer who became the third employee at oDesk (now Upwork), he built Rev on a simple bet: people will pay for curated quality, and people everywhere want to work from home. Today Rev serves over 100,000 clients including 60% of the Fortune 500, and Chicola is steering the company toward AI tools for the legal system, where accuracy is not optional.
Craig Peus
Craig R. Peus is the CEO of illuno, a Plano, Texas technology company building the first purpose-built staffing marketplace for off-duty law enforcement officers. Backed by Mark Cuban Companies, illuno lets businesses hire certified, on-duty-grade police officers through an app in minutes, while handling compliance, insurance, and payments and giving departments visibility into officer moonlighting. Peus brings a wide-ranging executive resume - a Stanford biology degree, leadership roles in energy midstream (Gravity Midstream), agtech (Tree3), and capital advisory (Blossom Street Capital) - to a sector he argues is two decades behind on technology.
Mort Fertel
Mort Fertel is the co-founder and CEO of Poplin (formerly SudShare), a nationwide peer-to-peer marketplace often called the 'Uber for laundry,' which connects customers with independent Laundry Pros across 500+ markets and 8,000 zip codes. Before laundry, he spent two decades as a globally known relationship expert and author of the Marriage Fitness system, used by millions in marital crisis and the subject of the documentary 'Back from the Brink.' He started Poplin in 2018 alongside his teenage triplet sons after his wife, drowning in laundry for their five kids, asked why she was still washing clothes like her grandmother.
Anthony Mironov
Anthony Mironov is the co-founder and CEO of Wingspan, a New York fintech building payroll and benefits infrastructure for the 1099 economy. After a career in private equity and a stint as a freelancer who got tired of reverse-engineering his own paycheck, he started Wingspan in 2019 with Greg Franczyk. The company has processed more than $3 billion in contractor payments and raised $54 million, betting that as one in three American workers go independent, the back office for that work needs to be rebuilt from scratch.
Sahil Hasan
Sahil Hasan is the CEO and Co-Founder of Dots, a developer-friendly global payouts platform that has processed over $1 billion to more than 1 million gig workers, creators, and contractors in 190+ countries. A UC Berkeley EECS grad with a CMU master's degree, Sahil spent time as a Research Engineer at Google X before co-founding Dots through Y Combinator's S21 batch. The company raised an $8.9M Series A in February 2026 led by DCM Ventures, is profitable, and growing revenue 400% year-over-year.
Laura Speyer
Laura Speyer is the co-CEO of Catch, a benefits marketplace that helps America's self-employed and independent workers find and enroll in health, dental, and vision insurance. After Catch's original founders shut the company down in March 2023, Speyer and her former CLEAR colleague Alexa Irish bought it with their own money and relaunched it in time for the November 2023 open enrollment. A Yale-trained dealmaker who came up through KKR and led corporate development and growth at CLEAR, Speyer pitches Catch as a 'personalized HR department' for the roughly 60 million Americans who work without an employer's safety net.
Jonathan Perichon
Jonathan Perichon is the Co-founder and CTO of Checkr, Inc., a San Francisco-based AI-powered background screening platform he co-founded in 2014 with Daniel Yanisse. A French-born software engineer who discovered the gig economy's broken background check infrastructure while working at an LA startup, Perichon turned that frustration into a $4.6 billion company serving over 100,000 clients including DoorDash, Lyft, Coinbase, and Uber. A Y Combinator S14 alumnus who applied three times before getting in, he embodies the principle that persistence and execution beat credentials every time.
Mahmoud Ghulman
Mahmoud Ghulman is the Co-Founder and CEO of Nash, a San Francisco-based AI logistics platform that serves as the delivery infrastructure layer for commerce - connecting businesses like Walmart, 7-Eleven, and thousands of restaurants to hundreds of delivery providers through a single API. A physics graduate from MIT, Ghulman spent nearly a decade building gig-economy and AI businesses before co-founding Nash in 2021 with high school friend Aziz Alghunaim. The company has raised $29.1M in total funding from Andreessen Horowitz and Y Combinator, and is pioneering agentic AI for last-mile delivery orchestration at enterprise scale.
Melody McCloskey
Melody McCloskey is the founder and CEO of StyleSeat, the largest online marketplace for beauty, grooming, and wellness services, connecting over 350,000 independent beauty professionals with 10 million+ consumers across the United States. She co-founded StyleSeat in 2011 alongside Dan Levine, bootstrapped the company for 18 months before raising $40.7 million in venture funding, and has helped power over 200 million appointments while generating $12+ billion in total revenue for small businesses. A San Francisco native who studied French and International Relations at UC Davis, McCloskey built StyleSeat out of her own frustration with booking beauty appointments, turning a personal pain point into a platform that fundamentally reshaped how independent beauty professionals run their businesses. She is also an angel investor and Cleo Capital scout, focused on backing female-led startups at the pre-seed through Series A stages.
Ravi Swaminathan
Ravi Swaminathan is the co-founder and CEO of TaskHuman, a real-time 1:1 digital coaching platform that connects employees with live human coaches via video call across 1,000+ topics - from fitness and financial planning to leadership and emotional well-being. A seasoned technology executive with roots in semiconductor and enterprise storage, he built TaskHuman in 2017 after recognizing that no generic article or pre-recorded video could replace the power of an expert human conversation. The company has raised $35M+ in funding, grown ARR 700% between its Series A and B rounds, and now operates across nearly 50 countries with a network of 1,000+ coaches.
Sumir Meghani
Sumir Meghani is the CEO and Co-Founder of Instawork, a San Francisco-based on-demand staffing platform connecting over 4 million skilled hourly workers with businesses across hospitality, light industrial, and warehousing sectors. A Stanford and Harvard Business School alumnus and Paul & Daisy Soros Fellow, Meghani built Instawork from a Y Combinator S15 startup into a $171.8M-funded company operating in 30+ markets across the U.S. and Canada, earning the EY Entrepreneur of the Year 2023 Bay Area Award and back-to-back Inc. 5000 rankings.
Wei Deng
Wei Deng is the CEO and founder of Clipboard Health, a San Francisco-based healthcare labor marketplace that connects nurses and other healthcare professionals with open shifts at facilities like nursing homes and hospitals. Founded in 2016 and backed by Sequoia Capital and IVP, the company achieved unicorn status at a $1.3B valuation after raising $94M in total funding. A Yale College and Yale Law School graduate, Deng pivoted through six to eight business models before discovering that flexible, on-demand shift matching was the key to solving healthcare staffing shortages. Known for her relentless persistence — she pitched facilities seven months pregnant — Deng built Clipboard Health into a platform serving over 5,000 facilities across the United States.
Hemkesh Agrawal
Hemkesh Agrawal is an engineer-turned-venture-operator who went from arriving in the US from India in 2019 to holding a patent, founding multiple startups, and becoming Head of Engineering at Redbud VC in Columbia, Missouri. A Board of Trustees Scholar at Michigan State University with a perfect 4.0 GPA, he co-founded UniServices (an Uber-for-odd-jobs platform for college students) and Village (AI-driven HOA management), and was one of only 15 selected out of 4,000 applicants for the Survive & Thrive entrepreneurship bootcamp at age 16. He bridges deep technical skill with startup hustle, embodying the rare builder who can go from Arduino prototypes to VC infrastructure.
Tony Xu
Tony Xu is the co-founder and CEO of DoorDash, the food delivery giant commanding roughly 60% of the U.S. market. Born Xu Xun in Nanjing, China, he immigrated to the United States at age four, grew up washing dishes alongside his mother, and turned that lived understanding of the service economy into a company now valued near $100 billion. He led DoorDash through its blockbuster 2020 IPO, the $8.1B acquisition of Wolt, and the $3.9B acquisition of Deliveroo, while also serving on Meta's board of directors.
John Zimmer
John Zimmer is the co-founder and former President of Lyft, the ride-hailing company he built alongside Logan Green from a carpooling experiment at Cornell into a public company worth $24 billion at its 2019 IPO. Known for his hospitality-school ethos and relentless focus on human connection over transaction, Zimmer spent 16 years transforming how Americans think about car ownership and urban mobility. After stepping down from Lyft's board in August 2025, he launched Yes&, a consumer company-builder focused on health, connection, and joy.