The founder story we usually hear skips over who was also doing bedtime, packing lunches, and figuring out childcare in between the funding rounds. Sana sits down with Ashley Wilson, founder and CEO of Persephone.ai, a secure digital vault built to help survivors of abuse document evidence and build safety plans, to talk about what building and scaling companies as a single mother actually looks like.

Ashley shares how 20 years as an operator and technologist led her to found her own company for the first time, why trust had to be the product's real MVP, and the quieter, less talked-about costs of founder life when travel and networking aren't always an option.

About the Guest:

Ashley Wilson is the founder and CEO of Persephone.ai, a secure digital vault built to help survivors of abuse document evidence and build safety plans. She previously founded JAW Analytics and is a graduate of the Harvard Business Analytics Program. She is a single mother of three boys.

Key Takeaways:

• The skills built helping other people's companies succeed can become the foundation for your own, years spent as an operator or partner aren't wasted time before founding
• When trust is the core product requirement, self-funding the first version and testing with real early adopters can be the clearest way to learn if people are ready to rely on it
• As a founder balancing caregiving, the traditional "fly out and build relationships in person" growth path may not be available, plan around real constraints rather than treating them as a personal shortfall
• Meet people where they already are, offering multiple simple ways to submit information (text, email, voice) can make a tool far more accessible to people who aren't naturally tech-savvy
• Momentum and precedent matter for adoption in systems like courts, wider use today can build the case for acceptance tomorrow
• Fear pointing you toward something usually means that direction is worth moving in, not a signal to stay in place

Connect With the Guest:

Website: https://ashleywilson.ai

LinkedIn: https://www.linkedin.com/in/lashleywilson/

Company: Persephone.ai

Episode Chapters:

[00:00] The Founder Story We Don't Usually Hear

[01:27] Meet Ashley Wilson, Founder and CEO of Persephone.ai

[02:55] From Insurance Underwriter to Harvard Business Analytics

[07:36] What Persephone.ai Actually Does

[12:15] Trust as the MVP: Bootstrapping the First Launch

[19:46] The Quiet Cost: Travel, Networking, and Life as a Mom Founder

[37:25] A Message to Hesitant Entrepreneurs: Fail Faster

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