⚡ Top of Mind

Adam Ryan Mar 19th, 2026

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Hey all,

Callie is back from her sabbatical, Austin is now a girl dad, and I built my first ever web app. What a week!

With that, let’s dive into it.

In partnership with

WHAT'S TOP OF MIND

1) Travis Kalanick’s back

If you don’t know the story, Travis Kalanick was pushed out of Uber in 2017. The company he founded.

His biggest supporter on the board, Bill Gurley, voted to remove him and bring in a professional CEO. Gurley is one of the most respected venture capitalists of all time, and he believed it was the only path forward for the company.

Many employees disagreed. Some investors did too. But it was also clear that the culture inside Uber had become toxic and, frankly, pretty gross.

The decision ended an era. In many ways it hurt both of them. Travis lost the company he built. Gurley spent years defending one of the hardest decisions of his career.

Fast forward to the past two weeks.

Gurley released a book that people seem to love. Travis announced a new company, atoms.co. Seeing both of those things happen at the same time made me reflect on something that always baffled me about Travis.

His ability to fundraise.

Fundraising is incredibly hard. At least in my experience. It takes time, coordination, rejection, and an absurd amount of energy. But with Travis it always looked effortless.

This week he shared how he actually raised money for Uber, and the process was anything but easy.

He would rent four hotel rooms and schedule investors throughout the day. Each room had a different type of investor, ranging from larger funds to smaller ones. He would move between the rooms pitching them privately, essentially running a full production for the entire day.

At the end he would gather the commitments and close the round shortly after.

When I heard that, I was honestly shocked. I had never heard that story before.

What stuck with me even more was something he said about the process itself. If fundraising feels easy, you are probably doing it wrong. Anything that produces an extraordinary outcome usually required an extraordinarily difficult process.

That idea stayed with me.

The process itself is often the barrier. The harder the process, the fewer people who will actually finish it.

Travis gave the analogy of a world class marathoner. “Do you see them smiling at mile 21? Of course, not they’re pushing themselves as hard as they can. That’s how Founders should feel about fundraising.”

I guess it’s never easy for anyone, it’s just the perseverance one possesses.

2) A takeaway from dinner

This week I went to a dinner hosted by LightShed Ventures, one of our earliest investors. It was a TMT (technology, media, telecom) themed dinner and the room was full of interesting people, ranging from the founder of Dear Media to the head of YouTube to Bill Gurley (the guy who kicked Travis out of Uber) to the guy who holds the patent that allows music subscriptions to exist.

I sat next to Jason Calacanis, who immediately said, “you poached two of my guys.” Lol. Awkward. Iykyk.

It was a super interesting conversation around AI slop, licensing name and likeness, the future of production, and more.

My biggest takeaway: no one really knows how to handle all the change.

It reminds a lot of people of what happened in the 90s with the internet, which basically took years for people to figure out the best tools and business models.

The other funny takeaway is that the room was generally pretty anti-OpenAI. Some people referred to them as the soon to be Yahoo of LLMs. Ouch.

But it was all speculative. No one really has a clue what’s around the corner.

The best thing to do is keep an open mind, keep learning, and keep asking questions.

3) My first application and it’s for us

This week I received a Slack from Denton letting me know about a request we get pretty frequently from the sales team.

I was determined to build a data first product for the sales team this month. I didn’t know exactly what it would be, but I knew we had a ton of data, I knew the sales team gets asked for it a lot, and it’s always kind of a pain to fulfill those requests because of bandwidth constraints.

Well, this was the project.

At 10am Denton sent that Slack, and by 9am the next day my MVP was made.

And though it’s definitely not perfect, and I’m sure there are bugs, you can now visit TAM.Workweek.com and start playing around.

You may find some data that looks off or run into a bug. If you do, please use the little feedback button in the bottom right and it’ll get answered ASAP. I know we can make it better.

What a wild world we’re living in.

QUESTION OF THE WEEK

What’s the next project I should try to build?

Give me some ideas of things that can help make your life easier!

Thanks for giving it a read. Make it a great one.

Adam