main-street
(5)
Marcos Digliodo and the value of a second pair of eyes
A tennis scholarship brought Marcos Digliodo from Argentina to the United States. Wine distribution, Main Street mentoring and digital coaching gave the Paramount Pursuits co-founder a different kind of doubles game.
Hello Alice: A good business should not need the right friends
A Houston founder could not move across the country for an accelerator. Hello Alice grew from that inconvenience into a platform for finding capital, getting advice and making fewer expensive guesses.
Baton
Baton is a New York-based online marketplace that helps owners sell their small businesses and helps buyers acquire them. It replaces the slow, opaque world of traditional business brokers with fast data-driven valuations, confidential listings, digital data rooms, and guided M&A support - achieving a roughly 70% close rate at about half the cost of conventional brokers.
John Waldmann
John Waldmann is the founder and CEO of Homebase, the team-management app built for the people who run local businesses - restaurants, salons, retail shops and the hourly teams behind them. Started in 2014 after watching a childhood friend drown in paper schedules and his sister juggle unpredictable bartending shifts, Homebase now serves more than 150,000 businesses and 3.8 million workers, processing hundreds of millions of shifts a year with scheduling, time clocks, payroll, messaging and earned-wage access. A Stanford GSB grad who once sold tuxedos and started his first online business at 13, Waldmann is an unapologetic believer in accountability over consensus, 'operating velocity,' and the idea that AI will create more small business owners, not fewer.
Harper Insurance
Harper (YC W25) is an AI-native commercial insurance brokerage that turns the $100B+ industry of email and spreadsheets into a fully autonomous engine for Main Street America. Co-founded by Dakotah Rice and Tushar Nair — two Goldman Sachs alumni who swore they'd never work in insurance — Harper uses its internal AI platform, Harper Hub, to automate form completion, carrier matching across 160+ carriers, underwriter follow-ups, and client communications. The result: 1–2 day quotes instead of 5–7, 85% success rate on traditionally 'uninsurable' cases, 5,000+ businesses covered across 35 states, and 1,000+ customers handled per month versus 20–30 for a typical human brokerage. Backed by $54M in total funding led by Emergence Capital, Peak XV, and Y Combinator. Named after Dakotah's mother's maiden name.