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.
Rob Bailey retweeted
We’ve had 47 calls with private equity teams since May.
Operating partners, value-creation leads, portco CEOs and CTOs.
Here’s what they’re saying about AI and how responsibilities are changing inside a portco:
ONE - People are the bottleneck, and they bring it up first.
Adoption and change management came up as the bottleneck in 16 of the 47 calls.
One fund’s AI lead put it this way: “Change management is the name of the game a lot of times with these things... That’s a big reason why our team has grown.”
They grew the team to put people on site at portcos and help staff change how they work.
TWO - Teams are too big, but nobody wants to cut without proof.
A value-creation lead looking at a portco with about 500 engineers told us: “the teams are too big and I’m advocating for smaller teams... I can’t do that without showing that there is improvement in productivity first.”
So the first project is to measure what changes on one team. The reorg comes later, if the numbers support it.
THREE - What happens to the freed-up capacity is still an open question.
On the same call: “Whether that’s headcount reduction or that’s improved throughput and therefore better products. We can discuss where that productivity goes.”
A CTO on another call had already made his choice: “I would probably rather triple our output than scale down.”
Before a portco starts with AI, someone needs to answer:
→ Fewer people, or more output from the same people?
→ Which team goes first?
→ What number proves it worked?
→ Who owns the AI after the pilot?
→ What does it cost to run at full usage?
FOUR - Buy-in decides who gets help first.
“I am less keen to engage any portfolio company where the leadership isn’t as bought in.”
The CEO of one portco in that fund has drafted a note to staff but hasn’t sent it yet. The message is roughly: “either you’re adopting and using AI and going faster or you’re not going to be part of our growth.”
FIVE - My biggest takeaway: everyone’s role is changing at the same time.
The operating partner has to prove the productivity gains before anyone starts restructuring.
The CEO has to make it clear that using AI is part of the job.
The CTO has to work out how to run smaller teams with less ceremony. “At my last company we let go of a lot of the scrum structures and it was fine,” one SVP of Engineering told us. A PE-owned distributor now has a “digital AI asset manager” doing the day-to-day work of a product owner.
Everyone has work to do.
If you’re an operating partner, pick one team in one portco. Before changing anything, measure rework, cost per finished task, and time from ticket to production. Answer the five questions above. Then run a small AI-assisted team alongside it for a month and compare the results.
That’s what we do inside portcos.
We start with one workflow and measure the results against a number the business already tracks.
We work month to month, and if we don’t deliver, you don’t pay.
AI HEROES: NASDAQ.
Nasdaq is targeting $100M a year in cost savings by the end of 2027 by putting AI to work on its own coding, client service, finance, legal, and HR.
ir.nasdaq.com/news-releases/…
fool.com/earnings/call-trans…
seekingalpha.com/news
Last week a Fortune 500 customer we plan to onboard said they loved our product. But our UX felt too "AI generated".
They were right.
But how exactly does one fix this? Um.....we asked AI. We actually got a great answer. Here's the TLDR.
"1. Outcomes over dashboards.
2. Less is more. Fewer charts, clearer insights.
3. Unique insights, not just dashboards
4. AI-native ≠ chatbot. Intelligence should be embedded throughout the product.
Enterprise doesn't mean complicated. Powerful technology should feel effortless."
Dear Friends: We are hiring! We will be ramping up fast serving our customers in the coming months. Hiring Developers (Python+AI Dev Tools), FDEs and AEs. We are moving extremely fast. DM me. NO RECRUITERS. Also, no anonymous x accounts. Must be US time zone or BST.
Rob Bailey retweeted
I don't think most B2B teams understand what's happening in GTM engineering at the moment
Here's what one GTM engineer on our team gets done in a day
The setup: Claude Code, Hermes in Slack, the Clay CLI, n8n, and a folder of skill .md files.
Before lunch:
> A new client's domain goes into our GTM skill. ICP, TAM estimate, 4 offers to test, messaging angles. Back in about 30 seconds (we QA it, most clients don't ask for edits)
> Account list sourced from a Slack message on a walk. Google Maps scrape, qualification, waterfall across 5 email finders, double verification. Nobody opened a single tool
> Every account scored against the client's rubric and tiered A/B/C
> 3 script variants per persona, email 1 and email 2, spam words already stripped
> Campaign live in EmailBison by 11:30
After lunch:
> Replies from the morning send tagged by intent, drafted, and scored against ICP by 5 agents
> Booked meetings pushed to the CRM with a research brief for the rep
> Lead magnet landing page built in Lovable in a couple hours
> Last week's sales call transcript turned into a new messaging angle for next week's 10,000 emails
Laptop closed by 5.
In 2023 that was a week for 4 people and a VA writing "personalized" first lines.
Run the numbers.
Rob Bailey retweeted
just landed in SF and looking to hire someone for this role, dm/email if you have a candidate I should meet with asap
brex.com/careers/8864648002
AI HEROES: DEUTSCHE TELEKOM.
Deutsche Telekom expects AI and automation to cut about €2.5B a year from its indirect costs by 2030, as bots take customer calls, flag network trouble early, and help write software.
telekom.com/newsroom/latest-…
reuters.com/business/media-t…
telecomlead.com
Rob Bailey retweeted
yesterday, I met a YC founder who’d just pivoted.
the kind of founder you could see raising a $15M series A in the next 6 months.
asked him how he was finding customers for the new product.
his answer:
“i look for people who just inherited the problem.”
thought he meant newly promoted executives.
sort of...
he finds people who recently started a role.
then looks for evidence that they’re trying to fix something his product solves.
a new VP of sales posting about rebuilding outbound.
a new head of ops asking how other teams handle onboarding.
a new marketing lead discussing attribution tools.
the job change gets them on his radar.
what they say next gives him a reason to reach out.
because someone starting a new role is usually doing a few things:
> asking questions.
> reviewing what’s already there.
> deciding what needs to change.
and sometimes, they’re doing all of that publicly on linkedIn.
imagine this comment on linkedIn:
“3 weeks into the new role. great team, but our reps spend way too much time updating spreadsheets. fixing that is our top priority.”
most people see a career update.
he sees a specific problem, someone who owns it, and a reason to start a conversation.
his message would be:
“hey [name], saw your post about the spreadsheet overhead. where’s most of the manual work happening? prospecting, CRM updates, or reporting?”
that’s it.
no calendar link.
no unsolicited demo.
one question they can answer in 10 seconds.
if they say “reporting,” and his product only fixes prospecting, he moves on.
if they say “prospecting, we’re doing everything manually,” there’s a conversation worth having.
here’s the playbook:
step 1: find people who recently joined roles that own the problem you solve.
step 2: check the company fits. right team size, relevant use case, realistic need.
step 3: read their recent posts and comments. look for a priority, a question, or a frustration.
step 4: reference the specific thing they said.
step 5: ask one useful question before asking for a meeting.
you can use @GojiBerryAI to help surface prospects through job changes and topic engagement, then personalize outreach around those signals.
now it’s your turn.
find someone who just inherited a problem you can solve.
start the conversation.
go close some deals.
Rob Bailey retweeted
99% of salespeople ask "random acts of questions."
They come off as a checklist.
They don't GUIDE the buyer through a sequence of 5 realizations.
That's the key.
And that's what star salespeople do in the modern era of selling.
Here's how it works.
Rob Bailey retweeted
I’m the CEO of Product Hunt and see 100s of launches a week. My current thoughts on new infra begging for startups:
1) Voice AI - infra for voice agents is getting really good w @pipecat_ai @Vapi_AI @DeepgramAI @ElevenLabs et al. and yet I rarely see good voice tech in the real world.
2) Decision Models - Jev / @typesafeai leading the charge. It reminds me of the mech-building in Zelda TOTK - an explosion of possibilities!
3) Personal Agents - they work now. And they need tools, apps, MCPs.
4) Extensions (OpenAI). We all live in agentic interfaces now. It’s like a new platform. Someone needs to build a Slack replacement that lives in Codex, for example.

















