Fostering Fellowships with Founders in an AI-Crazed World

Tonight I’ve got two events to attend. The first is at the hyper-exclusive/cool building that I was at yesterday… which makes me think… how exclusive is it really? Hahhaha. But its exclusive enough that I get denied/waitlisted for their events all the time. Just hit a lucky streak here. After that, I’m going to the DocuSign offices inside of the DocuSign building! I mean, pretty cool, huh? LOL. DocuSign fan girl day!

Why Attend: The first event describes itself as “thoughtful conversation for founders, no panels.. just talking” or something like that. The next (which I’ll be late to.. how late, depends on the first event’s quality), which is just panels from various professionals in the AI industry, talking about “remembering humans” while making AI products - or something like that. Let’s see how it goes!!

Photo Collage and Commentary

Notes from the Event

I was running very early to the first event, over an hour! But, I just felt like getting out of my house and over by the waterside. This worked out amazingly well cause I got to soak up a lot of sun in a nice park in the grass before heading over. I ended up heading over 15 minutes early and just let myself in. Then, seems maybe 3 people hosting this event are here - but they didn’t act welcoming/warm to me (also, this is a coworking space, so they’re not to assume I’m there 15 minutes early for their event).

• And they’re deep in conversation (talking about AI + running/starting businesses - classics) and I don’t wanna boot in and/or force them to talk to me.

• So I just found a seat by a charger and let my laptop charge while writing this.

As I said, I may just leave this event a little early so that I’m not super late to the second one. We’ll see the vibe. But, honestly, given the way they’re not even saying “hi” to me (and may be HOSTING this event), it makes me not want to stay… though, they did say this is a very small group invited for this talk tonight. So, I’d like to give it a try. At least for the first 15 minutes. But if it keeps being like “hotty toddy” or whatever, I’ll just bail and go to #docusign time.

OMG but then the next guy who walks in they are super welcoming to. A tall handsome guy - they ask if he’s here for the event, etc. LOL.

• So I went up and said, yeah I’m here for the event too (even though I got here 10 minutes ago and you guys ignored me), just didn’t want to interrupt you guys. But then they were like oh, no no no.

Then, I got a distracting email from a parent who enrolled in my PRINTABLE babysitting class - though they wanted something more interactive, and I was like, “brah, we got that - look” and then I sent them my amazing weekly babysitting class. Let’s see if they choose to join.

After that, the discussions begun. Mostly just people talking about things, but the host of the event revealed a lot that explains why I get such an ‘exclusive vibe’/waitlist/etc from them. Its cause they legit use AI to screen all the attendees and filter out who is/isn’t allowed to come to events. They use AI to rate people and decide who should join. Also, use AI to figure out who to message on Linkedin, etc.

• So, obviously, I rate quite low on their AI’s verdict and only can join when they have someone else in charge OR not a huge crowd. Noted. (eyeroll)

Then, I left that event early and went over to the DocuSign building. It was locked from the first floor but then I got someone to let me in. However I wasn’t able to go up to the proper floor so I went to the floor I know I have a lot of friends on - in that same building - and told them the sitaution. THEN they first gave me a hard time for beign so late (one hour late) and I said pish posh, who cares if you’re late. At least you showed up. Plus, I wanted food/pizza as advertised hahaha.

THEN - lemme just write this now isntead of the end: I MET A GIRL WHO WORKS FOR EBAY IN THE TRADING CARD DIVISIONNNNN. (Like the other day when I met a guy who worked for Chewy who had NO respect for Ryan Cohen…). and so I was like, “are you excited about the acquisition?” Etc… you know what, i”Ll just put the video here cause I made a video about it - ANDNNDNDNDNDND lemme say too - she wasn’t a fan EVEN THOUGH GAMESTOP HAS A PARTNERSHIP WITH PSA. SO HOW DO YOU NOT CARE ABOUT THIS STUFF WHEN YOU WORK IN THE TRADING CARD DEPARTMENT????

• AND THE GUY SHE WAS TALKING TO WORKS IN DESIGNING FINANCIAL TRADING APPS even though (his words) THEY HAVE A LOT OF EVIL!!!

• THEN THE EBAY GIRL SAID, ALL EVIL - BUT I DIDN’T HEAR HER WELL

• AND SO I SAID, WHAT’D YOU SAY? ALL EVIL?

• THEN SHE SAID, " NO, ’ IT’S ENIVITABLE, BUT YOU JUST HAVE TO GET OKAY WITH YOURSELF”

• I’M LIKE WTFFFFFFFFF. THIS IS THE REASON WE’RE ALL IN THIS MESS, FEEDING THE SYSTEM, PROFITING OFF OF PAIN???

ANYWAY - here are my notes from the event. And I can’t wait for all of this to come to fruition, and I am hyped for the future and for brave, integrity-driven leaders to redefine what is cool, admirable, mainstream, and normalized.

Okay, my notes from the talk:

Ai came out of human impulses, fears, its shaping us.  But how?  In 2026.  A lot of tools help us be decisive, innovative, faster, productive, and efficient.

LLMs help us with recommendations.  We outsource a lot of decisions to just a handful of sparkles.

Agentic is automating a lot of complex tasks and there is fear that innovation is feeding software.  

• Fear has created a lot of companies to put AI onto this rush. A nd so many products are looking the same, the same chatbot.  The same existential threat, design looks alike 

What is worth choosing over ChatGPT or Claude?
- the conversational interface is a relief from years of doomscrolling.  

At what point does familiarity breed into contempt.  The prompting is not natural for every user, for every context, every task.  

We can create things faster than ever. It is liberating to see how quickly you can test things, way faster than ever before.  But it is causing a lot of confusion and chaos.  Managers of chaos. 

Last year, OpenAI prompted AI to do styles, but they had to ban certain styles with copyright backlash. 

• So is Ghibli a style or specific distinctive boy of work created by living human artists?

Do we still value and discern art by human artists?
- Working faster frees us up to do more.  Being more productive doesn’t always equate to an exercise experience at work. 

Boundaries are here.  The pressure to be efficient is real.  But of revery task agentic AI can automate, there is a cost somewhere else. 

• Data centers create relentless noise solutions and driving up energy bills in underdeveloped.  70% of American oppose data centers in their area.  

City officials are moving forward with a 1-year moratorium.  4 companies are proposing 5 new data centers which would take up 1/3rd of the city’s average energy use.  10 times more than the existing.  There is capability and consequences.

• Each query consumes five times more electricity than a basic web search.  

Maybe (Jevon’s paradox) - we end up consuming more.  More usecases . We’ve seen this with airtravel.  As planes became cheaper, more people began flying. 

• Not just more efficient systems but more conscious of our consumption.

For each promise, there is capability and consequences. Can we cal it intelligence if its built to ignore its own consequences?

• Our creative human edge relies in the questions we ask. Right now, we’re not asking a lot of questions to each other - we’re picking hype or doom.  Picking sides.

• Will AI save us?

• Will AI destroy us?

Both narratives collapse our agency into inevitability.  They say hte outcome is predetermined so your choices don’t matter.

• This can lead to nails.  Both perspectives miss here and now. The choices we’re makign tdoday, models we’re choosing, the models we push back on.  Whether we pay attention here in Seattle or across the US and world. 

This is not a dismissal of long-term thinking, we have to think about the future.  But it’s a call to stay present with whats unfolding.  Let’s look at 5 roles to play in the workplace.

• Not skills, not optimization, and ways of being ourselves as we are. Let’s strengthen and bring forward in a meeting, prototyping, or whatever the task may be.

The catalyst makes the unclear visible - but it can not discern when a team needs redirection.

• The next is a bridge.  Connecting what has been fragmented.  There are divergent systems.  Misaligned goals, teams.  The bridge sits in the tension between them to build trust.

We need a listener: Unspoken needs, sensing what is about to two happen.

Curators cut through slop.  Has taste. 

• The subverter challenges conformity when AI leans towards sameness.  When AI combines patterns, it can not innovate outside of that.

SO lets start iwth the catalyst.  

• Use AI to help you do that

• But speed is not the soul of this role

Ai won’t replace designers, but we may outsource so much thinking to AI that we forget what we believe about the problem we are solving

• Prompt operators.  We need conviction to maintain our human edge. 

We need to ask a set of questions.  SO for each of these are a set of questions:

• What are we trying to learn from this prototype? Not prove?

• This prototype proves we can build it.  But should we?

• Who benefits from this working?  What are the benefits of its design

Critical thinking is the soul of this role. Claude doesn’t know that when your product manager is feeling pressure or exhaust from management or a pivot.  We need to know human signals of whats happening with this organization.  Knowing the moment to redirect things.

• Know what is yours - your beliefs, values, experience, what you know to be the right or wrong approach.

• Ask “do I know what I actually believe about hte problem I am solving?”

The bridge can go in, be a systems thinker - what is the trust we’re assuming but didn’t actually build?

Is efficiency the goal or have we stopped asking waht else matters?

• AI promises to make us more efficient, but all of us have more values beyond efficiency.  SO do our users and customers.  

A cool product out there is called “be my eyes” - can connect to human sighted volunteers to navigate tasks.  So you could either go to AI for quick tasks or still contact a signed team for more nuanced ones.  AI is an extra choice for them.  Still can contact a human if they want to. 

Income moments you may want efficiency and some moments you value connection.  And want to talk to a real human to get that response. 

• Dude this makes me realize some people may WANT human connection but will get cheaper AI instead.  

• Just makes me think about my company - and the people at the event earlier today who said they find agents, AI agents, to replace the humans they hire overseas.

Humans in the loop should be more like Humans on the loop - don’t want to be stuck in the loop.

The terms we use for these things determine how we shape them.  

• Signals more of the control we have of how automation is working, reshape it, turn around, get off the lop.  

With agentic AI we are at risk of seeing fragmentation and vlosign visibility of what agents are doing

- - When we design for efficiency before trust.  Being the bridge can be a fantastic role in this time of AI.

But how do we practice trust?  Show up for each other.

• A lot of what we’re taking is to take the AI summary versus showing up.  We’re losing the sense of being with each other in ways that are unscripted.  We need to learn what trust means.  Showing up for each other can strengthen the muscle for being the bridge.  

• Is trust being assumed but not built?  

For the LISTENER: we can not vibe code in a vacuum.  Or else we are building things that are oppressive and disconnected.

What’s changing in people’s lives that we haven’t caught up to yet?

• What do we need to do to step outside for a moment.

• When designing for google maps, we tried to design for motorbiks cause in many countries, tehy outnumber cars 4:1.

• It wasn’t until they met with local communities around teh world and learned that many rides like to just look at the map, memorize it, and then just drive.

- they were able to build motorbike mode into google map.  Adding landmarks that had never been there.

• Languages that ha’dnt been there

Distinct routes by aurally riding on teh bikes themselves and used machine learning to scale it out.

When tehy launched, they got a lot of compelling feedback and “this isn’t quite accurate” - how do we make this better even after the launch? 

• They saw about 100M, even 2B users.  

Protect the embodied experience.  So much is on screen. We’re on our computers all the time.  We can not seek or understand new ideas unless we take a break from AI for a moment and listen to what’s happening outside. 

• A quick practice is to do motion sketches.  When traveling just put pen to paper and let the motion of wherever record whats happening.  IT allows her to stay connected to surroundings and jsut draw scribbles.

When is the last time a real environment changed your mind about a design decision?

- The next is the curator - cutting through slop to protect quality.

Groipedia as a competitor to wikipedia.  He boasted it’d be more accurate and depth, but it had more inaccurately and bias.  But people say, no - wikipedia is best

• So where is quantity masquerading as quality?

And who is deciding what quality means?  A human, a model, or no one?  How do we take in a moment to decide what quality means?  IT’s important to bring questions of quality to the table because we can generate so fast. 

• Choose what you let in.  

Let your mind wanter a bit and go to a new city with no agenda.  Or take your team to an offsite that is actually an offsit, away from the building.  Outside.  Something very different so unexpected ideas emerge

• When we have new experiences, we get new ideas.

What are you letting through in your current projects that isn’t good enough quite yet?  

• Lastly: subverter - challenging conformity to bring about distinction.

Even a product called YouTune subverts the YouTube algorithm and shows videos and songs you may not have otherwise seen.

• Reminds me of stumbleupon.com in the old days

• Then websitecarbon.com will say how much energy is being consumed evertytime someone visits the page.  

Someone who seeks transparency - it’s the first step towards change.
What default solutions deserve to be questions?
What if people dont’ want what we think tehy want?

There is so much push to put AI and chats in their face?  How can we uncover that futher?

• We must stay in contact with discomfort.  It is uncomfortable to ask questions.  AI is frictionless - and the more we leaninto that world, the more that uncertainty feels like failure.

We have breakthroughs when we’re bored, struggling.

• Is it??

AI can not innovate outside of its patterns.  But when we sit in discomfort we can not prompt our way out of uncertainty.

If AI can only give what exists, what are you willing to create that doesn’t exist yet?

How can we reclaim our agency a bit?  Reconnect to the purpose of our work?  Not jsut the tasks but the purpose.  Thats what is important to figure out.

• Know what is actually yours.  Show up for each other.  

Protect embodied experience.

• Choose what you let in. 

Stay in contact with discomfort. Every choice we make shapes who we are becoming. So what will your choice be?

• Tech Without Losing Your Soul = her article 

What can she do as a human - not just as a worker?  Do you agree with all thats being done?  If not, how can you be a human?

• Not only just generating, but also see what are you generating and see if it matches your goals.  Meet people where they are and don’t give up.  

She gave this same talk in Germany before - but it went a bit longer.  

• We may be heading and get some course correction, but difficult to know what that will be.  

So how is AI affecting people in ways?  Data centers - affecting energy bills, lives, and communities.  New in terms of tech cycles.  Lets see how this helps with course correction.