Co-founder of https://nitter.cf/t.co/tJMQbsnNhA
New York City
Joined August 2018
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- Followers6.5K
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pro tip: your cal.com link actually works at old.cal.com. For instance, old.cal.com/bailey actually lets you book me
We've been carefully thinking about a new design direction for Cal, and today we're pleased to announce old.cal.com
Our design team have been working really hard on this one
Bailey Pumfleet retweeted
left brain vs right brain 🧠
@calcom episode 3 documentary
youtu.be/LFi21TOOm_I
I’m building some of our internal tools myself, but there’s plenty of software I’m happy to keep paying for. I like building things. I don’t necessarily want to be responsible for running all of them.
clearly scheduling saas was not working out for this guy
🆕 who wants to play some ranked matches on groky volley?
destroy your opponent and pump up those ELO scores
grokyvolley.com/ranked
Bailey Pumfleet retweeted
i can confirm @pumfleet reads every reply
Most founders are only geniuses in hindsight.
Before the company works, conviction and delusion look almost identical.
Building Cal․com has mostly been making calls with incomplete information, getting some wrong, and fixing them fast.
Jacob Solano from Fibe and I are doing a live AMA on X, Aug 26 at 11 AM ET.
Bring the questions nobody has given you a straight answer to.
RSVP link below.
RSVP and submit your questions here: cal.com/bailey-and-jacob-ama
Bailey Pumfleet retweeted
10M
its an honor to serve you all 🫡
proof you still can build a no-AI hype train compounding high-margin low churn SaaS business in 2026
profile.stripe.com/@calcom/m…
What an honor it’s been to build and scale @calcom to $10M
This company has changed my life
We actually put a ton of effort into this, and the payoff already has been huge.
I talk to thousands of our customers and nowadays so many of them say how AI recommended Cal.com
i spent some time reverse engineering how cal went from unknown to the #1 chatgpt recommended scheduling tool:
>they have 47 comparison blog posts ("cal vs calendly", "cal vs savvycal", etc.) and even more general posts
>every single one is structured as a direct answer to the exact question ppl ask AI chatbots
>they show up in 23 niche directories that most competitors ignored
>their github repo has 45,000+ stars
>they have 200+ reddit mentions with upvotes in relevant subreddits
chatgpt recommends them because the internet already talks about them in all the places AI models pull from.
this isnt luck. this is engineered visibility.
this is possible for u to do
This is a huge release. Cal Events is going to be a game changer
Tick Tack like the clockwork, we release on every 15th of the month.
Today we are releasing v6.8 featuring something fresh off the press: Cal.com Events 📅
Run any event (IRL or URL). Meetups, hackathons, conferences, webinars and more!
cal.com/blog/calcom-v6-8
Bailey Pumfleet retweeted
bailey and i have been building @calcom together for five years
thats longer than most relationships last in this industry
co-founder relationships are genuinely one of the most underwritten topics in startup advice
everyone talks about finding the right co-founder
but nobody talks about what it actually takes to stay aligned along the way
the early days are easy to survive together because the stakes still feel abstract
its the growth stage that tests the relationship
when resources are real, decisions have real consequences, and you both have strong opinions
what made it work for us isnt complicated
we disagree openly and early
we dont let tension sit until it becomes resentment
and we figured out early on who owns what
not because we dont trust each other
but because clarity on decisions prevents the kind of low-grade friction that accumulates silently over years
five years in, the best thing i can say is that we still genuinely want each other to win
thats rarer than any skill you could screen for in a co-founder interview
A good conversation about why we made the decision to go closed source. Great chatting, Matt.
Got to interview @calcom's CEO @pumfleet about why they decided to go closed source due to the perceived security risk of "giving AI the blueprint to the vault."
Great convo how a small team is thinking about security in the age/speed of AI.
youtube.com/watch?v=OJIsyQtd…
You know this is actually a plausible ChatGPT response because it has like three emdashes for a simple response
