Venture investor, operator and founder coach joins the AI-native startup to scale partnerships and operations, and brings Cofounder.AI to every Good Trouble Ventures portfolio founder
LOS ANGELES, Oct. 6, 2026 /PRNewswire/ — Cofounder.AI, the venture-backed, AI-native startup leveling the playing field for small business owners and entrepreneurs, today announced that AJ Thomas has joined as Chief Operating Officer. Thomas will lead Partnerships and oversee Finance, Legal and HR alongside CEO Clarence Wooten, her former colleague at Google X, Alphabet’s Moonshot Factory. At Google X, she served as Global Head of Talent & People Products. She is also cofounder of Troublemaker Ventures, home to the venture fund Good Trouble Ventures and the growth advisory firm The Troublemaker Lab.
The appointment brings Thomas’s work full circle. After years of investing in, coaching and championing founders, she will now help build technology that puts that same support in the hands of entrepreneurs everywhere.
“Most small business owners are building alone, without a cofounder, operating leverage or a board to lean on,” said Clarence Wooten, Founder and CEO of Cofounder.AI. “AJ has spent her career giving founders exactly that kind of support, at Google X, as an investor, and as an operator and leadership coach. She knows what it takes to build teams and companies that last, and she’s the right person to scale Cofounder.AI’s partnerships and operations.”
“I’ve sat on every side of the table: operator, investor and leadership coach. The pattern is the same everywhere. Talent is evenly distributed, but support is not,” said Thomas. “Cofounder.AI gives every entrepreneur the operating leverage that used to be reserved for founders with the right network. My job is to make sure humanity and technology get equal weight as we build it, so we can deliver on our mission for the entrepreneurs and small business owners who are the heartbeat of our economy.”
Capital, culture and community
Thomas brings more than 15 years of experience across venture capital, talent and company building. Her work at Troublemaker Ventures, which backs founders and their teams with both capital and hands-on support, runs on three levers:
Capital. As General Partner of Good Trouble Ventures, she invests in founders who challenge the status quo.
Culture. As Managing Partner of The Troublemaker Lab, she coaches founders and enterprise teams on growth strategy, go-to-market, operational rigor and building cultures that hold up under pressure, including adopting AI in ways that sharpen teams rather than replace them.
Community. She connects founders, investors, operators and technologists across AI, emerging tech and venture capital, widening access to the rooms and resources that shape innovation.
At Cofounder.AI, Thomas’s early priorities include expanding university and ecosystem partnerships that bring the platform to student and early-stage founders. She is also a sought-after voice on how AI is reshaping funding, teams and communities; an executive coach and advisor to multiple startups; and a bestselling children’s book author.
Alliance with Good Trouble Ventures
Alongside the appointment, Cofounder.AI and Good Trouble Ventures are forming an alliance partnership. Every current and future Good Trouble Ventures portfolio founder will receive a free one-year Cofounder.AI license, giving them an AI cofounder for fundraising readiness, diligence and day-to-day operations from day one.
“Capital alone doesn’t build a company. Operating leverage does,” said Kat Steinmetz, Cofounder and General Partner of Good Trouble Ventures. “Putting Cofounder.AI in every founder’s hands means our support doesn’t stop when the meeting ends.”
About Cofounder.AI
Cofounder.AI is a venture-backed, AI-native startup leveling the playing field for small business owners and entrepreneurs. Founded by Clarence Wooten, a two-time exited founder and former Executive Entrepreneur in Residence at Google X, Cofounder.AI gives every entrepreneur an AI cofounder to help them plan, fund and run their business.
About Troublemaker Ventures
Troublemaker Ventures is a holding company that backs founders with both capital and hands-on support. It operates through two businesses: Good Trouble Ventures, an early-stage fund investing in category-creating founders, and The Troublemaker Lab, an advisory firm that coaches founders and enterprise teams on growth strategy, financial and operational rigor, and culture.
Media Contact
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SOURCE CoFounder.AI
