Four Previous Podcasts

As I look ahead to producing new content this month, I wanted to dig through the archives and glance back for a moment.

My first podcast was Yup & Coming. Looks like it's still on spotify. I recorded those episodes from Loja Ecuador in a blanket fort.

My cohost James and I had a blast making it. I see him infrequently when I visit NYC, but otherwise we don't chat as often.

One of our goals was to showcase peers whom we anticipated becoming leaders in the world. The guests we interviewed are all amazing and inspiring humans who continue to develop fascinating and thoughtful lives.

Recently I've spent the most time with Nancy and Tiger. The most famous now would have to be Leigh Marie as a partner at Kleiner Perkins, perhaps followed by Drew as a leader at Anthropic and former cofounder of Sal Khan.

I'm very glad we took the time to record our chats back then. Some of these folks are so wonderfully focused on their personal compounding that these days it's truly an honor if I even receive a reply here and there lol.

Although our theme and cohosting did not endure, I still wanted to have intentional conversations with old friends. To make things slightly more formal than a phone call, but relaxing professional constraints to open up the dialogue, I set up The Andy Pod.

Again, all the guests are wonderful 11/10 people and I'm proud of each artifact we shipped. Nikhil is a particularly special friend who helped me create Lean On Me. He happens to run a juggernaut $1.25B healthcare company now. Working closely with him—even way back in 2015—opened my eyes to what world-class looks like, and I'm grateful for many wonderful things that have come from our relationship over the years. This is in part why I didn't need to intern with Elon.

For the first time, my show included a couple people I didn't previously know. It was profoundly enjoyable getting deep with Arun and Thomas on air. At the time, Thomas was building his own podcast featuring people I seriously admired—such as David Rosenthal, cohost of Acquired.

Things dropped off as I became more professionally absorbed with Senseg, my first startup. I moved to Quito and got cozy with Ecuador's banking sector.

After shutting down that company, I launched the Shuffle Dating Podcast for our new business. Handing it off to the team and later shutting it down taught us about quality control and the need for founder-led marketing. It was one of the many hard lessons we eventually learned.

Last but certainly not least is Simply Overthinking. I started it with my cofounder's girlfriend this past summer while transitioning away from Shuffle. It ended rather catastrophically when I inadvertently took a 10-day leave from freedom.

I came back to find the youtube channel deleted and Cassie unresponsive. As I write this, I just discovered I may in fact be a pebble in her shoe.

It's sad because I'm the one who bought the domain, set up the website, created our gmail, set up the Youtube, did all the edits on Riverside, and uploaded everything to various platforms. I was pretty shocked to find it all gone, passwords changed, without any discussion at all.

Not all projects end happily and wholesomely. As PG points out, execution risk—specifically team dynamics—is the most common failure mode for companies. It's hard to anticipate getting cancelled by yourselves.

After a few attempts over many weeks to reconnect and discuss this, I've now decided to simply re-share my backups below. I'm fortunate to have these and believe it's within my rights to publish. As a courtesy, I'm even leaving the links unlisted on Youtube.

One of my most interesting classes at MIT was Hal Abelson's on Foundations of Information Policy. We read a lot of Supreme Court cases. To me, archiving things feels intuitively proper, like it's part of free speech on the internet somehow. When it comes to both content and friendships, I prefer soft-deleting in case we want to re-visit down the line. Reversibility.

This blog post will soon be forgotten, and I only have 11 subscribers at present, so why does it really matter anyways? When you're living in the looong tail as I am now, you're not creating any major ripples (yet).

We had a good run. As with all the pods on this page, it was very fun making it! And I'm grateful for how it led me to my current creative path.