Top seed investor Gale Wilkinson says her past failures as a founder help her coach her startups to succeed
Apr 2, 2021
This story is available exclusively to Insider subscribers. Become an Insider and start reading now. Seed 100 and Seed 25 honoree Gale Wilkinson is the managing partner of Vitalize Venture Group. Vitalize has invested over $50 million across 70 startups. Wilkinson became a VC after two failed attempts at her own companies. Read the Seed 100 list of the best seed VCs and the Seed 25 list of the best female seed VCs. For Gale Wilkinson, the managing partner of Vitalize Venture Group, past business failures are a key part of helping her portfolio founders succeed. "I can share my mistakes with founders," Wilkinson said. And there have been plenty of willing students: Vitalize has funded over 70 founders, investing about $50 million in seed-stage startups since Wilkinson founded the firm in 2012. Wilkinson's journey into venture capital wasn't linear. With a degree in marketing, she began her career consulting for consumer-packaged-goods companies before landing a strategy role at travel website Orbitz. She bootstrapped a side hustle in those years, an education-technology startup called WhatCollegeForgot. She worked on it during nights and weekends, but it never took off. While getting her MBA from the University of Chicago Booth School of Business, she started her second business, a human-resources tech startup called HireBrite. That one fizzled, too. But Wilkinson never despaired and never slowed down. She founded Vitalize Venture Group in 2012, originally called IrishAngels, an angel-investing network affiliated with Notre Dame, where she was an adjunct instructor teaching early-stage investing. And she found her stride. "It really happened at the right place and at the right time," Wilkinson said of Vitalize, which she considers her third business. From angel investing came the move to seed-stage investing. In 2017, Wilkinson launched IrishAngels Ventures, which was rebranded as VitalizeVC in 2019, as the group's seed-stage venture fund. Vitalize Fund I is now its own $16 million vehicle investing in scalable software companies such as Placer.AI and The Project. Meanwhile, IrishAngels has become a 270-strong angel-investor network that invests in business-to-business and business-to-consumer startups and has backed companies such as TradingView and Chime. Both are part of Vitalize Venture Group, and Wilkinson said she's led $50 million worth of investments through IrishAngels and her Vitalize fund combined. Wilkinson looks for founders who are well rounded, especially in the tasks needed not only to build a product but also to run a business. "With founders, I look at if they're strong operators," Wilkinson said. "I want to know if they understand all the facets of their business at the seed level." Wilkinson's advice to seed-stage founders is to learn how to "wear many hats" and to know their own strengths from sales to product to technology. "I hear other VCs say that there is only one right way into this industry, which isn't true," Wilkinson said. "What I care about is if what founders have can resonate well." Was this article valuable for you?