Olo turns 21 today. On 9.21.2006, @GMA and a young reporter named @DavidMuir, now anchor of @ABCWorldNews, broke the story by delivering text-ordered coffees to the anchor desk of @DianeSawyer and @RobinRoberts. Six million viewers for six-person @Olo. What a ride! 🚀

Today's meeting tools give you a transcript, but nobody tells you how you did. I'm so excited to announce Work Coach (a new mac meetings app). Work Coach helps you by: - Observing you in meetings (interviews, 1:1s, sales calls, team meetings) - Analyzing how you show up to those meetings - Identifying opportunities to improve - Replaying the exact moments from your meetings where it happened - Role play conversations (intros in an interview, asking for a raise, etc) - Interviewing your coworkers to get feedback that you're not getting I'll put the download link below.

This. WTF @collectivei? Just hearing from friends that you did the same thing to my contacts. This is unreal.

2025 had the lowest rate of - mass shootings since 2006 - homicides since 1950s - teenage pregnancy in recorded history - suicides since 2020 - road fatalities since 2019 - drug overdose deaths since 2019 - alcohol consumption in recorded history - inflation since 2020

We just raised $20M (Menlo, Sequoia, Felicis, Snowflake, Databricks) and launched Kai—the first superintelligent AI co-worker for customer success. It shouldn't take 100 people to serve 1,000 customers. Kai knows every customer, acts instantly, never drops the ball. Agency.inc fortune.com/2025/11/12/elias…

So proud of you my brother!

🙌🏽🙌🏽🙌🏽🙌🏽🙌🏽🙌🏽

Most people have no idea what it actually takes to be a founder. They talk about vision, grit, or passion. Those words are props. What you really sign up for is a life where every decision feels like it costs something real. You will spend years being misunderstood. By your team, your family, even the people you hire to help you. You will fail in public and still need to keep the energy up in private. Every founder lives with the weight of knowing that you can do everything right and still get crushed by luck, timing, or somebody else’s mistake. Founders aren’t braver than anyone else. They just get used to uncertainty, then stop waiting for clarity. Most of your wins won’t feel like wins at all. The first revenue will be too small. The first team will outgrow you or leave. The first product that feels right will barely matter to the market. You will doubt yourself in private, sometimes every week. The founders who last figure out how to keep moving while the ground shifts underneath them. Most outsiders want the founder badge but none of the scars. They want the upside, not the drag. The hardest part is sticking around after every plan gets blown up and you have to rebuild with less optimism and more scar tissue. What makes it work isn’t relentless hustle or some mythical trait. It’s learning to make peace with constant discomfort, and then making decisions anyway. If you need constant reassurance, you’ll give up before the real work begins. If you want everyone to like you, you’ll never make the calls that matter. If you can’t handle months where nothing feels certain, this life will eat you alive. But if you can hold your own in chaos, get better at being wrong, and still want to show up and try again, you just might have a shot at building something that matters. That’s what it actually takes. And nobody cares until you make it work.

Dear Founders, Take money off the table in the next round. Love, Brian.

I often re-read @natfriedman's personal website (former Github CEO)

If a few of you are up, would love for you to try an early alpha version of what I've been vibe coding on. A domain suggestion tool. agent.ai/agent/domain-sugges… Super-easy, you enter an idea/concept and it generates a list of domains and their prices (on the major marketplaces). Note: It takes about 30 seconds to run (it's putting the LLM through its paces).

👏🏽👏🏽👏🏽

Congratulations team!! So proud of the entire ⁦@Olo⁩ family. ⁦@Olo⁩ Enters into Definitive Agreement to be Acquired by ⁦@thomabravo⁩ businesswire.com/news/home/2…

Worth reading Sam's thoughts on SaaS.

👏🏽👏🏽👏🏽

Buffett: "Who you associate with is enormously important. And don’t expect to make every decision right on that. But your life is going to progress in the general direction of the people you work with, admire, and befriend." Charlie Rose Interview 2009:

Waiting for certainty is the fastest path to irrelevance.

The speech I wish I gave. Bravo 👏🏽

Starting today: if you’re building something important and need the best talent - join us. And if you’re among the best and looking for a new challenge… take our test! (And if you’re interested in games, puzzles, talent, etc, apply to help us build!) MeritFirst.US

Complaining is not a strategy.