Jes Wolfe has small business advice that cost her two deals to learn. She twice bet Hoodline on a deal that would change everything, and both died days before going live. Her rule for small business owners now: build on singles and doubles, not home runs. She ran Hoodline, the local news company that later sold to Nextdoor, before taking over Rebel Girls in 2020. She tells Elizabeth Gore how a three-day ski trip turned into a board seat and then the CEO job, how she learned her father had died while she was at 18,000 feet on Aconcagua, and why she is now launching the San Francisco Signal. Featuring Jes Wolfe, CEO, Rebel Girls Elizabeth Gore, Co-founder and President, Hello Alice Presented by Block Advisors, built by H&R Block. Timestamps 0:00 Two companies, one lesson about home runs 0:15 The IRS just made one thing easier for small business owners 0:50 Meet Jes Wolfe, CEO of Rebel Girls 1:31 The book no publisher wanted, and the Kickstarter that answered 3:40 A three-day ski trip that turned into a board seat 4:29 From board member to CFO to CEO 5:19 Her co-founder left and the pandemic started 6:13 Mission, sleep, and the sun rises anyway 7:47 What 5:30 a.m. swim practice taught her about leading 9:31 Aconcagua, the highest peak in the Americas 11:00 The news that reached her at 18,000 feet 12:30 Why coming down was worse than going up 13:19 How it changed the way she runs a business 14:10 The San Francisco Signal, first serve January 2027 15:28 A women's first league, not a little sister league 16:30 The Valkyries and a billion dollar valuation 17:28 From books to podcasts to YouTube 18:45 This is amazing, but they're all dead 21:04 Hoodline, and the collapse of local news 22:21 The dirty unicorn: two home runs that died 23:33 Build on singles and doubles 24:24 Rikki's, Curie, and her small business shout-outs 26:07 Tax break: what small business owners miss between filing seasons 26:30 Estimated taxes, the $1,000 threshold, and the four deadlines 27:00 Payroll taxes and the Form 941 dates 27:23 Filing and depositing, plus Form 944 and Form 940 27:52 When your state adds another layer #RebelGirls #smallbusiness #smallbusinesstaxes #founderstory #TheBigIdea #YahooFinance == AlphaSpace by Yahoo Finance: A Professional-Grade Investment Platform Built for Everyday Investors. 👉 https://finance.yahoo.com/about/promos/gold/alphaspace?ncid=100003571