‘Nightmare’ Kickoff Meetings: One Founder’s Long Road to Funding Her AI Startup

Growing up in Alaska, Heather Shoemaker always felt that the ability to speak a foreign language was a superpower. That led her to study French and Spanish and earn a bachelor’s degree in linguistics. While working as a performer and bartender after college, she He was driving through Seattle when he heard a report on NPR that described Java programming as the future of technology. She decided on the spot to go back to school and learn a different kind of language: coding.

Shoemaker earned an engineering degree and spent the next decade as a software developer reformatting source code for companies that were expanding their operations internationally and needed their software to support multiple languages. He realized that the biggest obstacle was not the software. Companies with a global presence and a largely English-speaking workforce needed more help providing customer service. With artificial intelligence and her skills as a developer, Shoemaker saw an opportunity to bestow her superpower on everyone.

In 2017, he released language I/Oan AI-powered SaaS platform that provides real-time, multilingual customer support in over 100 languages.

Shoemaker was used to being the only woman in the room, from her grad classes and working at AI, where women do their own makeup. a quarter of the industry. As a founding woman and CEO, felt he was in uncharted territory when in 2019 he went looking for investors for his self-sufficient company, based in Cheyenne, Wyoming.

Less than 2 percent of enterprise software companies are founded by womenand despite generating highest returnsHowever, startups run by all-female teams struggle when it comes to securing venture capital backing. During the first half of this year, women received just 2 percent of funding and made up just 6.9 percent of deals, according to Sales book data. Shoemaker assumes the number should be even lower for female founders who are software developers. Still, knowing the stats didn’t prepare her for the reception she received at dozens of failed pitch meetings.

“I talked to so many people it was just a nightmare,” she says. “I don’t know why they think what I’m doing is easy.”

Shoemaker realized that venture capital firms weren’t used to seeing a woman, especially one with technical skills rather than an MBA. During a meeting in Silicon Valley, a partner learned that Shoemaker was releasing hard tech and had written the original code herself. They asked, “How difficult can it be to replicate what you coded?” Shoemaker says, implying that if a woman wrote the software, it must be easy for any other developer to copy, making it less valuable.

Another male investor, who passed by, told him: “If you were an older man with a long beard, an AI launch would be much easier for me. That would be easier.” normal. we are not accustomed East.“

One morning on his daily run, Shoemaker hatched a plan that reached farcical proportions. Life would be so much easier if Language I/O had a male founder, so why not pretend to be one? He considered shortening his name to Heath, growing a beard in Zoom meetings, and went so far as to investigate voice modulation software. Just before his fundraising efforts turned into a Shakespearean comedy, Shoemaker decided against it.

“I thought about it some more,” he says with a laugh. “You don’t want to start a relationship with a VC who lies about who you are.”

That dismissive attitude toward women working in AI is a problem not just for female founders, but for society as a whole. By 2025, AI will have created 97 million new jobs, according to the world economic forum. As algorithms become more integrated into everyday life, the people who write the code will need to be a reflection of the population.

The alternative, a programming monolith, produces biased results, even unintentionally. Gartner estimates that up to 85 percent of AI projects return erroneous results due to bias in the data, the algorithms, or the teams responsible for managing it. That means companies looking to take advantage of AI will end up with faulty products.

For example, Shoemaker explains, if AI translates the word doctor from a gender-neutral language to a gender-neutral language, the word the program will almost always choose to give the user will be the masculine form, while nurse will translate to the feminine form. .

“It drives me crazy,” she says. “And now, because it’s not always about gender binary, we need to start thinking in gender-neutral terms — no one has addressed that issue yet.”

After dozens of rejections, Shoemaker had considered giving up venture capital, but in October 2020 he found a bit of success closer to home, raising $500,000 in Wyoming. But she needed more capital. A Jackson, Wyoming-based adviser connected Language I/O with East Coast angel network Golden Seeds, which focuses on female-led startups, and Boston-based investor Eric Schnadig, who told him to Shoemaker that he was going to introduce him to a so-called “super angel”. Shoemaker didn’t know what that meant, but he was willing to meet with potential sponsors at this point. In Boston, she finally met someone who really listened to her speech.

Bob Davoli, the founder and managing director of Gutbrain Ventures, reacted very differently to the other investors Shoemaker had pitched. “He immediately got the market opportunity and wasn’t arguing with me about the size of the market,” she says. “I wasn’t under the false impression that Google was going to do exactly what we do.”

Davoli, whom Shoemaker described as a feminist, was not your typical VC. Known for his hands-on approach and his hobby as a singer-songwriter, he had a 30-year track record as an investor and had landed in business week cover in 2000. His briefcase Made up primarily of enterprise software platforms, including AI-focused startups Shoemaker says finding an investor with such deep industry knowledge was crucial and made the launch easy.