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The DTC beauty category is crowded. To break through, Jennifer Anniston’s brand LolaVie, worked with Roku Ads Manager to easily set up, test, and optimize CTV ad creatives. The campaign helped drive a big lift in sales and customer growth, helping LolaVie break through in the crowded beauty category.

Learn more.

This weekend, I had the joy and privilege of saying goodbye to my 99-year-old grandfather.

He was a World War II veteran, married for 63 years, a loving father, and the most encouraging grandpa I could have asked for. There are endless things I learned from him over the years, but two feel especially present to me right now.

The first is that he never stopped learning.

In 2022, when I was working at a startup, I remember scrolling through new user signups and seeing his email address pop up. He had created an account just to understand the world I was in. In his Southern accent, he’d admit he didn’t fully understand all of it, but he’d tell me he thought it was very impressive and he didn’t know how he felt about seeing a Power Ranger out of costume (this was specific to the product we were building lol.)

While also in his 90s, he made an Instagram account – downloaded the app on his iPad and all. During his funeral, when I shared my amazement about his ability to keep up with the times. The pastor followed up said something simple that hasn’t left me: he wasn’t on Instagram because he loved social media – he was on it because he loved me.

My aunt even found a small sticky note on his desk with questions he wanted to ask ChatGPT while cleaning out his office. Ninety-nine years old, and still curious about the newest tool in the world.

That tugged at my heart strings bigtime. Not because of the technology itself, but because of what it represented. He didn’t adopt new platforms because they were trendy or because he wanted to appear modern. He adopted them because they were a way to stay connected, to understand what his family was building, to keep his mind active. The technology was never the point. Staying engaged with the world was.

We talk a lot right now about AI as if it belongs to the young, to those who live in California, or the technical. But watching my grandfather approach new tools with humility and curiosity reminded me that learning isn’t generational – it’s intentional. The interface changes but the posture doesn’t. The people who remain curious, who are willing to ask questions even when they don’t fully understand the system in front of them, are the ones who stay alive to what’s changing.

The second thing he taught me was initiative.

A few weeks before he passed, he told me a story from when he was young. He wrote in response to a newspaper advertisement for North Wilkesboro Hardware Store, submitted an essay, and ended up winning $500. He used that money as the down payment on his first home in North Carolina. He didn’t wait for the perfect moment or overanalyze the odds. He saw an opportunity, took a chance, and built something from it.

What strikes me is how little that instinct has wavered over time. In the 1940s, initiative meant mailing in an essay and hoping it reached the right person. In 2025, it might mean shipping a small project, testing an idea, or opening ChatGPT with a list of questions written on a sticky note. The tools look different. The willingness to act does not.

In a world that feels increasingly automated and optimized, I keep coming back to those two qualities: curiosity and initiative. He stayed curious enough to download Instagram at 95 and curious enough to scribble down questions for ChatGPT at 99. He stayed bold enough, even as a young man, to write an essay that changed the trajectory of his life.

The platforms will keep evolving. The models will get better. The interfaces will become more seamless. But none of it replaces the decision to stay engaged, to keep learning, to try something before you feel entirely ready.

He was still learning at 99.

I hope I am too.