A few months ago, I pitched @fendien from @Work_Bench on the new company we're building.
Work-Bench is one of the best early-stage enterprise investors out there and their community is 🔥.
He stopped me 2 minutes into my presentation.
He'd already invested in something competitive. :-(
Was I bummed? Absolutely.
But I have enormous respect for the integrity Jonathan showed by being so transparent.
Hope our paths cross again.
When I heard Apple was making a foldable screen phone, I thought it was lame. I was SUPER SUPER wrong. Looks like it might be...a banger. Line started forming outside the Meatpacking store several days early. Like old times.
As a founder, you have two choices:
Option #1: Build an open culture where anyone can ask tough questions and challenge leadership. Harder in the short term. Much stronger in the long term.
Option #2: Build a closed culture where tough questions get punished and leaders can't take feedback. Easier in the short term. Long term, you're usually f--cked.
We're building #1. :-)
Rob Bailey retweeted
One of the best entrepreneurial stories I’ve ever seen, twice over.
Incredible case study of how a SaaS company can transform into an AI native company.
We built a $150M ARR business twice.
The first time took 8 years. The second took 2.5.
Today, Podium crossed $150M in AI annual recurring revenue.
Three years ago, we already had a great software business. Well over $100M in revenue, tens of thousands of customers, and a product we'd spent nearly a decade building.
And we decided to start over.
The business was performing well. But we believed AI was going to fundamentally change the software industry and make much of traditional software obsolete.
As a founder, you pour your life into what you're building. An insane amount of time, sacrifice, and effort. The hard part is not getting too attached to it.
When we started building our first AI agents, we had to confront the possibility that much of what we'd built might not be that valuable in the future. That's a tough pill to swallow.
But we also realized those same 10 years had put us in a unique position to take advantage of what AI could do for our customers.
Instead of protecting what we'd spent a decade building, we decided to bet the future of the company on AI employees that actually do the work for our customers.
We massively underestimated what we'd signed up for.
We ended up building entirely new operating systems for the industries we serve, from the AI agents all the way down to the systems of record. Now customers run their entire businesses on Podium.
Reinventing our product wasn't even the hardest part. We had to reinvent how the entire company operated.
When you've been running a company for over a decade, the operational inertia is incredibly powerful. We had to rethink how we build products, how we sell, how we serve customers, and how we run the business.
We effectively started a second startup inside an already successful company. And we're still at the very beginning.
Today, we have 20,000 AI agents working for our customers. They've helped generate more than $13 billion in revenue for those businesses. And we're barely scratching the surface of what AI will be able to do for them.
And we've done all of this while becoming profitable and generating free cash flow. We're building Podium to be around for decades.
Huge credit to our team for having the guts to make this bet and the ability to actually pull it off. We still have a long way to go and tons of problems to solve, but it's so damn fun to be winning when the opportunity ahead is this big.
In the age of AI, you can either disrupt your own company or wait for somebody else to do it.
I'd rather do it ourselves.
Rob Bailey retweeted
I popped into a coffee shop to grab a cappuccino and the barista recognized me and told me why he’s supporting me. I have interactions like this every day and I am deeply touched by it every time.
Rob Bailey retweeted
Today Monaco is launching Agent Matrix.
Monaco unleashes countless agents working together, goal seeking, with one outcome in mind: accelerate revenue growth.
If you don’t have an army of agents working 24/7 to accelerate revenue growth, you’re living in the past.
Apply for early access now.
Rob Bailey retweeted
My favorite AI dev setup right now:
- T3 Code running parallel coding tasks.
- Dot on a call while I work.
I explain where we’re going, talk through problems, and ask it to check GitHub when I need context.
It files issues, updates them as we work things out, and helps me decide what matters next.
Feels like having a coworker I can think out loud with all day.
Our team was talking about "stretch wow" features that we can bake into our product for our launch. It was probably the coffee talking, but "stretch wow" made me think of an 80s work-out video. So....
Rob Bailey retweeted
This is a MASTERCLASS from Ramp’s sales team. They scaled to $700M+ with outbound messages like these. 6 things this cold email does SO well:
1) The subject line is "Follow-up to HumanX," a conference the CEO, João Batalha of Amplemarket, went to. It reads like a thread he's already in.
2) The first line is about his own LinkedIn post on HumanX. The SDR, Michelle, ties it to her first conference for Ramp that same week, so they have something in common before she pitches.
3) She brings up the history. Amplemarket has connected with Ramp a few times before, so the ask is a “revisit”, which is a FAR warmer start than a cold pitch.
4) She names the competitor they already use. "Brex was built for startups, but Ramp is built to scale" gives him a 1-line, HYPER relevant reason to switch over.
5) The greeting and the sign-off are in Portuguese ("Olá" and "Obrigado"). Love this. It adds a human touch to the email.
6) She spelled João with the tilde, while his LinkedIn just says "joao." A LinkedIn scrape would have missed that 10 times out of 10.
ONLY thing I’d change:
The length.
It’s a tad long. However, it works regardless due to all of the other factors at play.
Love this, and I recommend taking some of these for your own outbound campaigns.













