Sam DeBrule

Now

I help founders before they have a company, while they are still deciding what to build.

We test ideas with potential customers, recruit world-class talent, and strategize for fundraising.

For the past few months I’ve worked six days a week with a defense tech founder who sold his previous company to SpaceX, working out what he builds next. I’ve helped him build the AI systems the company will operate on, recruit world-class talent, and prepare to execute his fundraise.

I also help founders who want to get acquired, are going through an acquisition, or are on the other side of a sale. I lived the process. It is lopsided, and I write to help founders navigate the process successfully.

Before

In 2021, I co-founded Heyday, an AI research assistant, and led customer discovery and growth.

I was one of the roughly 1% of venture-backed founders who are Black.

We raised a $6.5 million seed led by Spark Capital in 2022 and sold the company to BetterUp in September 2024.

After the sale I worked at BetterUp until October 2025.

From 2017 to 2025, I wrote Machine Learnings, a weekly newsletter about AI that reached 50,000 subscribers. Its guests included investors from Andreessen Horowitz, FirstMark Capital, Amplify Partners, and Bloomberg Beta, the CEOs of Airtable and Dataiku, and executives from Salesforce and Capital One.

I graduated from Brown University and have lived in San Francisco since 2015.

Personal

The values I work and live by are helpfulness, loyalty, and curiosity.

I am happiest when I’m spending time with my wife and daughter.

I’m usually training toward a fitness goal, so I can eat unlimited pastries. My current goal is a VO2 max above 57, and my favorite pastries are at Arsicault, b. patisserie, and Tartine.