Brent
@brent.chirrup.chat
Call center survivor (and owner) turned SaaS founder.
500k calls later and building @Chirrup.chat.
So tour and activity operators can ditch the boring work and get back to the best part of business.
SMB advocate, problem-solver, and travel addict.
500k calls later and building @Chirrup.chat.
So tour and activity operators can ditch the boring work and get back to the best part of business.
SMB advocate, problem-solver, and travel addict.
Pinned
Brent
@brent.chirrup.chat
· Jan 11
True story: I used to shower with my phone so I wouldn't miss a customer call. Fast forward 6 years and 20,000+ calls later, @chirrup.chat was born. Because no one should feel that kind of anxiety running a business. Tour operators need a new BFF, and we’re building it.
SF is the best place to build tech — but where’s all the travel tech?
I’m co-hosting a travel meetup in SF with @TravelMassive and @Neighbourgood
Tour operators, builders, creators — come hang.
🗓 Sep 23
📍 SF
🍷 Free, casual, and very much about the future of travel
RSVP 👉 luma.com/xw8mc47q?tk=...
I’m co-hosting a travel meetup in SF with @TravelMassive and @Neighbourgood
Tour operators, builders, creators — come hang.
🗓 Sep 23
📍 SF
🍷 Free, casual, and very much about the future of travel
RSVP 👉 luma.com/xw8mc47q?tk=...
Resurgence of Travel · Luma
✈️ In collaboration with Travel Massive and Neighbourgood
Join us for an inspiring evening as we dive into the Resurgence of Travel — a conversation…
luma.com
September 6, 2025 at 1:08 AM
SF is the best place to build tech — but where’s all the travel tech?
I’m co-hosting a travel meetup in SF with @TravelMassive and @Neighbourgood
Tour operators, builders, creators — come hang.
🗓 Sep 23
📍 SF
🍷 Free, casual, and very much about the future of travel
RSVP 👉 luma.com/xw8mc47q?tk=...
I’m co-hosting a travel meetup in SF with @TravelMassive and @Neighbourgood
Tour operators, builders, creators — come hang.
🗓 Sep 23
📍 SF
🍷 Free, casual, and very much about the future of travel
RSVP 👉 luma.com/xw8mc47q?tk=...
Wasn't expecting to feel so loved after canceling a flight!
Bravo, Southwest, for this well placed bit of copy🥰. Def brightened up my day.
Kind words, even when automated, can go a long way.
Bravo, Southwest, for this well placed bit of copy🥰. Def brightened up my day.
Kind words, even when automated, can go a long way.
March 21, 2025 at 8:50 PM
Wasn't expecting to feel so loved after canceling a flight!
Bravo, Southwest, for this well placed bit of copy🥰. Def brightened up my day.
Kind words, even when automated, can go a long way.
Bravo, Southwest, for this well placed bit of copy🥰. Def brightened up my day.
Kind words, even when automated, can go a long way.
They don’t teach this in business school.
Too many leaders are stuck trying to “win” instead of actually building something great.
There’s a big difference.
One is about ego, the other is about impact.
Imagine how different the world would be if more people in power got that.
Too many leaders are stuck trying to “win” instead of actually building something great.
There’s a big difference.
One is about ego, the other is about impact.
Imagine how different the world would be if more people in power got that.
March 15, 2025 at 6:39 AM
They don’t teach this in business school.
Too many leaders are stuck trying to “win” instead of actually building something great.
There’s a big difference.
One is about ego, the other is about impact.
Imagine how different the world would be if more people in power got that.
Too many leaders are stuck trying to “win” instead of actually building something great.
There’s a big difference.
One is about ego, the other is about impact.
Imagine how different the world would be if more people in power got that.
LinkedIn messages = 🤮
"Hey Brent, your problem solving skills truly elevate every challenge you take on."
There are so many problems with this. And it's why I barely use LinkedIn anymore.
"Hey Brent, your problem solving skills truly elevate every challenge you take on."
There are so many problems with this. And it's why I barely use LinkedIn anymore.
February 22, 2025 at 5:23 PM
LinkedIn messages = 🤮
"Hey Brent, your problem solving skills truly elevate every challenge you take on."
There are so many problems with this. And it's why I barely use LinkedIn anymore.
"Hey Brent, your problem solving skills truly elevate every challenge you take on."
There are so many problems with this. And it's why I barely use LinkedIn anymore.
What better way to break through the doom and gloom than with a feature release?
February 6, 2025 at 3:49 PM
What better way to break through the doom and gloom than with a feature release?
It's a good day to unplug 🌴
January 20, 2025 at 6:45 PM
It's a good day to unplug 🌴
Sometimes I wish WordPress would go away.
Sometimes as in all the time.
I feel dumber every time I use it 😵💫
Sometimes as in all the time.
I feel dumber every time I use it 😵💫
January 18, 2025 at 9:24 PM
Sometimes I wish WordPress would go away.
Sometimes as in all the time.
I feel dumber every time I use it 😵💫
Sometimes as in all the time.
I feel dumber every time I use it 😵💫
Is VC broken? I don't think so.
But where the money flows? That’s a different story.
When the same people keep getting funded, we miss out on so much untapped potential.
Backing underrepresented founders isn’t just fair—it’s smart. Curious to hear your thoughts.
But where the money flows? That’s a different story.
When the same people keep getting funded, we miss out on so much untapped potential.
Backing underrepresented founders isn’t just fair—it’s smart. Curious to hear your thoughts.
January 16, 2025 at 10:25 PM
Is VC broken? I don't think so.
But where the money flows? That’s a different story.
When the same people keep getting funded, we miss out on so much untapped potential.
Backing underrepresented founders isn’t just fair—it’s smart. Curious to hear your thoughts.
But where the money flows? That’s a different story.
When the same people keep getting funded, we miss out on so much untapped potential.
Backing underrepresented founders isn’t just fair—it’s smart. Curious to hear your thoughts.
Reviewing telecommunication compliance info for Canada (fun I know).
Didn't realize how scandalous snowshoeing is 😲!
What am I missing here?
Didn't realize how scandalous snowshoeing is 😲!
What am I missing here?
January 13, 2025 at 2:16 AM
Reviewing telecommunication compliance info for Canada (fun I know).
Didn't realize how scandalous snowshoeing is 😲!
What am I missing here?
Didn't realize how scandalous snowshoeing is 😲!
What am I missing here?
True story: I used to shower with my phone so I wouldn't miss a customer call. Fast forward 6 years and 20,000+ calls later, @chirrup.chat was born. Because no one should feel that kind of anxiety running a business. Tour operators need a new BFF, and we’re building it.
January 11, 2025 at 2:06 AM
True story: I used to shower with my phone so I wouldn't miss a customer call. Fast forward 6 years and 20,000+ calls later, @chirrup.chat was born. Because no one should feel that kind of anxiety running a business. Tour operators need a new BFF, and we’re building it.
Gotta say it. The Bay is a magical place.
Big thanks to @inazarova.bsky.social from @evilmartians.com for hosting the Ruby&AI event! Loved hearing what @activeagents.ai and @kamil.fyi are building.
Love the SF #rubyonrails community 😁. Be sure to check out @rubyvideo.dev for other #ruby events
Big thanks to @inazarova.bsky.social from @evilmartians.com for hosting the Ruby&AI event! Loved hearing what @activeagents.ai and @kamil.fyi are building.
Love the SF #rubyonrails community 😁. Be sure to check out @rubyvideo.dev for other #ruby events
December 4, 2024 at 4:38 AM
Gotta say it. The Bay is a magical place.
Big thanks to @inazarova.bsky.social from @evilmartians.com for hosting the Ruby&AI event! Loved hearing what @activeagents.ai and @kamil.fyi are building.
Love the SF #rubyonrails community 😁. Be sure to check out @rubyvideo.dev for other #ruby events
Big thanks to @inazarova.bsky.social from @evilmartians.com for hosting the Ruby&AI event! Loved hearing what @activeagents.ai and @kamil.fyi are building.
Love the SF #rubyonrails community 😁. Be sure to check out @rubyvideo.dev for other #ruby events
Bluesky is a safe place, right? Ok then. Here goes...
I'm a #49ers fan😭
There, I said it. I know I'm not alone. But that doesn't take the pain away.
I'm a #49ers fan😭
There, I said it. I know I'm not alone. But that doesn't take the pain away.
December 2, 2024 at 6:26 PM
Bluesky is a safe place, right? Ok then. Here goes...
I'm a #49ers fan😭
There, I said it. I know I'm not alone. But that doesn't take the pain away.
I'm a #49ers fan😭
There, I said it. I know I'm not alone. But that doesn't take the pain away.
Hello founder friends! Anyone have any success stories about leveraging strategic partnerships to drive early sales? Or failure stories 🤪. Or any story at all.
#startup #saas #fundraising
#startup #saas #fundraising
November 27, 2024 at 2:05 AM
Hello founder friends! Anyone have any success stories about leveraging strategic partnerships to drive early sales? Or failure stories 🤪. Or any story at all.
#startup #saas #fundraising
#startup #saas #fundraising
Ok, day 2 in the books.
So what happened? Started sprint planning for a huge integration opportunity. Strategic partnerships can be a game changer 🤩🤩🤩.
So what happened? Started sprint planning for a huge integration opportunity. Strategic partnerships can be a game changer 🤩🤩🤩.
November 27, 2024 at 2:00 AM
Ok, day 2 in the books.
So what happened? Started sprint planning for a huge integration opportunity. Strategic partnerships can be a game changer 🤩🤩🤩.
So what happened? Started sprint planning for a huge integration opportunity. Strategic partnerships can be a game changer 🤩🤩🤩.
I 5x-ed my followers on Bluesky in one day. Follow for more hyper growth tips🚀🚀🚀
November 26, 2024 at 5:57 AM
I 5x-ed my followers on Bluesky in one day. Follow for more hyper growth tips🚀🚀🚀
Searched "travel tech" only to realize that "time travel tech" is way more popular. Doc Brown would be proud.
November 25, 2024 at 6:29 PM
Searched "travel tech" only to realize that "time travel tech" is way more popular. Doc Brown would be proud.
It's crazy to me when a business won't let you text them.
November 25, 2024 at 6:07 PM
It's crazy to me when a business won't let you text them.
Day 1 of fundraising on Bluesky.
Never formally raised money. And I hear this time of year is the worst time to try and raise. But business doesn't sleep so here we go 🚀🚀🚀
Never formally raised money. And I hear this time of year is the worst time to try and raise. But business doesn't sleep so here we go 🚀🚀🚀
November 25, 2024 at 5:42 PM
Day 1 of fundraising on Bluesky.
Never formally raised money. And I hear this time of year is the worst time to try and raise. But business doesn't sleep so here we go 🚀🚀🚀
Never formally raised money. And I hear this time of year is the worst time to try and raise. But business doesn't sleep so here we go 🚀🚀🚀