Attempting to make sales content fun. Building a tool that helps sales leaders unlock their reps time to maximize impact all while supporting my community.

I’ve always believed the most powerful kind of growth happens when you make people feel something.

That’s why I’ve spent my career building brands through story driven content, strategic experimentation, and community first execution. Because attention isn’t enough. You have to earn trust. And to earn trust, people need to see themselves in what you’re building.

I'm now Head of Growth at Anam.ai—a platform that’s making human-like AI personas feel not just believable, but impactful.

We’re building something new from the ground up.

Think: lifelike AI avatars that can coach your sales team, power your customer support, or scale personalized learning at the speed of automation.

It’s where expression meets intelligence. And I get to help take it from 0 to 1.

This team is dialed in. Passionate. Smart. Focused. The kind of people you dream about building with.

If you're experimenting with AI in your GTM motion or looking to personalize experiences at scale—we should connect.

And if you just want to talk content, growth, or startup life—I’m always down to jam.

Let’s build something unforgettable.

Fun fact: I used to run one of the top nightclubs in Guatemala before diving into tech.

A picture of me after leaning over my computer for 12 hours at age 33.

undefined undefined

Marketing Lead @ Anam | Building AI Humans

I’m no longer at Anam. 


I’ve had this update sitting in my drafts for a minute.

And it wasn’t because I was lost for words or anything like that, I just didn’t feel like this was relevant with everything else that’s happening in the world right now…

And it’s not, but LinkedIn is a place where I express myself and I use it almost like a journal, so the perfect time to share this update was when I felt like typing and I guess that’s now. 

If you’ve ever stopped working somewhere that mattered to you, you know the feeling.

You’re doing your day to day, researching, creating content, brainstorming a creative campaign push right before you go to sleep, and your brain randomly goes:

“Oh yeah. That chapter’s done.” 

At Anam, I learned what it feels like to build while everything in the AI space is still moving a billion miles an hr. 

Where almost every “final version” is still considered a v1 as we adapted and learned. 

There were versions I shipped, versions I’ve strongly defended, and versions I’ve re-created after someone smarter than me asked a question that made me rethink everything that I put together aha. 

Some days the job was strategy.

Other days it was, trying to explain a new category to someone who didn’t ask for a new category. 

Filming a video that I was 80% sure was cringey, posting it anyway, and hopping it hit. 

Turning a half-formed thought into something sharp enough for a customer to engage with and reshare. 

All of this I needed to live through to finally understand where I thrive. 

I, Joshua Bailey, am at my best when I’m close to the story.

Wheather that’s next to the customer, product, or to the messy middle where I couldn’t sit behind “best practices.”

And to the people I built alongside with at Anam, thank you!

For the honesty, the speed, and most importantly for all the teaching me so much along the way about building a product that’s changing the way people interact with AI. 

So… now what?! 

Well I got something for you coming out soon (like next week type soon) that I’m excited to share. 

But right now your guy has to update that LinkedIn profile and take a moment to appreciate what that season gave him before going back in at one hundooo.

I got an update on what’s next real soon!

Honestly nothing beats in-person. 

I started posting on LinkedIn at the start of 2024 and I quickly found out that these are my people. 

I was on a search. 

The search to find a community built on ambition, determination, positivity, and growth. 

And as much crap as I give this platform, if it wasn’t for this space, I wouldn’t have met so many of those who I can call friends today. 

If you’re not taking those genuine connections and finding time to meet up in real life, you’re doing LinkedIn wrong. 

:)

What sitting in an onsen in a ryokan built in 1666 in northern Japan taught me about marketing. 


Chill tf out. 

Getting angry or frustrated over a failed effort will only cause unneeded stress that won't just affect you, it will bleed onto those around you, making you difficult to be around and work with. 

And when you try to take on everything at once, you burn yourself out and perform way worse than you would by taking your time to ensure things are executed properly. 

So if you flop on a campaign, a post, or whatever else it is... don't worry, your world won't end. 

Own what happened, learn from it, and get back to work.

I’ve been embarrassed as hell to ask this question but I will… 


Anyone else’s fingers forget how to type after coming back from holiday break?!

I’d give the time of day to anyone who knocks on my door today. 

1. For the hustle
2. Because wtf not, I’ll be inside all day

Hiring questions every company NEEDS to ask! 


1. When you’re on a plane, do you cover your mouth when you sneeze? 

2. Do you walk your shopping cart back when you’re finished using it or leave it behind a random car? 

3. On a single person sidewalk, you’re with your partner holding hands, someone is approaching you, do you let go of your partners hand and move behind them for a split second so the other person can walk by or do you make them step off into the dirt? 

(Number three is the make or break question) 

Did I miss any other important ones?

Ava Chen is still missing... and we need help finding her... 

After many conversations at the #Theaisummit and #Agentforcetour last month in NYC, we came across a ton of websites and products who are still missing something fundamental:

a human way to interact.

Actual quotes from people we chatted with, I SWEAR. 

“I didn’t know this was possible.”
“I’ve never seen an AI you can actually talk to.”
“Why doesn’t every product have this?”
"Dude you have great hair." 

Okay the last one wasn't real, but you get the point. 

We’ve trained users to scroll, search, click, and read. But humans don’t communicate that way and we never have. We speak. Ask questions. Interrupt. And, we want answers NOW from someone or something we can connect with. 

Ava isn’t just a missing real-time avatar.

She represents every AI persona that should exist on your website, in your product, or inside your workflow, but doesn’t.

Sales. Support. Training. Onboarding. Education. Healthcare. And whatever tf else you can think of.

This mini-campaign was about sparking curiosity, standing out in the noise of the same ol' crap marketing, and of course sharing what’s possible when you're using real-time AI avatars. 

If your product still relies on text, forms, or static video you might be missing a persona too.

Help us, help you, find Ava Chen. Link in comments!

I love seeing brands use an LLM to create content. 

Because it makes it easier for brands who actually give a sh*t about implementing that human element, stand out and win attention. 

And those brands who can build a human connection with their customers by tapping into their emotions and mindsets to help create community, they’re the ones who deserve the “dub” since they’re putting in the work. 

And let’s be honest. 

Using an LLM to create content is just lazy. 

And no one likes to see lazy win. 

____________________________________

If you’d like, I can:

• Rewrite this so no one knows it’s written by an LLM 

• Add even more emotional nuance to increase engagement

• Optimize for LinkedIn’s crap algorithm

• Suggest emojis that feel natural (but not too natural)

• Generate 3 versions to repost since everyone will forget this post 

Just let me know how you’d like to proceed.

⎘   ›   +   −   ↗   ⋯

Hate to be the bearer of bad news on LinkedIn… 

There’s a ton of advice from incredible humans, but they’ve all made mistakes and that’s what lead them to those learnings. 

That perfect post of how they scaled “x” to “x”?! 

There was a ton of time and money that went into it that they’re not sharing. 

And what we don’t see from most of the people posting on here are those things they had to go through to get to where they are now. 

That’s why the people who are winning on this platform, and who are building a strong brand that people continue to follow, are tapping into their followers emotions. 

They’re sharing the journey. 

They’re willing to be different and are not worried about being judge for their failures. 

They keep it fu*king real and they bring their personalities into their content. 

They have this special ability that most of us lack in the real world which is being ourselves. 

These things are important because people want to connect with the real you. They want to buy from brands they trust, and founders who aren’t fluffing everything up to be “perfect”. 

So stop overthinking content and start writing like you would be talking to a random person four beers deep in a bar. 

P.S. An elevator pic of the homie and me just being, us.

LinkedIn Sales Nav needs a “real one” filter.

Hoh-heh-mee-noh Koo-yoo-foo Tsur-oo-yah. 

I had to Google pronunciation because, damn… that was difficult to say. 


When I’m asked “what do you like to do outside of work?” 

Me: “I love to create.”

Both my wife Karen Bailey and I share the same passion, this inner need to share our experiences with others. 

I tie it back to both of us growing up without much community. 

So we decided to build our own. 

So we started Usandtheworld a few years ago. 

And although we haven’t put a ton of time or effort into growing our pages… our goal isn’t to monetize and get free rooms and drinks and 1M dollars!! 

(Although that would be nice) 

Our goal is to help others learn what it’s like visiting new places and provide helpful tips along the way. 

And for us, I feel like making videos of our travels and posting them online is like journaling. 

It’s something we can look back on years from now and say “Although I was working my butt off at “x” job, we made the best of our time off together.” 

So to answer the question about how much does it cost for an onsen villa in northern Japan?! Watch the video we made over Xmas break and find out. 

P.S. Follow our journey, links in the comments below!

taplio

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