AI for Startups to Explore + Exploitive Coaching from Not Sean Kingston
Disclaimer: Everything below is a mix of what I observed and heard during the event. The goal isn’t to pinpoint "who exactly said what," but to share (usually) an outsider's view and overall perspective on these industries. I’m not here to act as a definitive firsthand source—readers should do their own research. I hope this inspires you to attend events, explore new industries, and hear what leaders are presenting. These notes combine my observations with thoughts on how things could run smoother and how ideas connect (IMO). I’m not an expert, you know? Just hanging out in the room with them. Enjoy.
Two things are going on tonight! First, I’m attending this event, all about the top AI tools startup founders can be using to make things more efficient. In addition, one of my friends is meeting me here who has gone from… homeless… to about to sell his company for 100M minimum. He’s helping me get the right mindset and succeed in becoming the all-star I know I can be.
Why Attend: Duh!! This sounds super helpful, interesting, and I’ll be curious if they suggest things I’m not already using. Things I can use or pass on to my interns. Let’s go KELLY TUTORS!!!!!!
Photo Collage + Commentary
i love being delusional about gamestop hahahah cause i dont think its all delusion!! but thats the whole point hahahah. its a cycle.
Notes from The Event
THE TALK ON AI:
actually. I hardly want to write it down. It was so basic and I didn’t learn much of anything at all. It was literally all already stuff I Know. I’ll do something unusual this time and just pick like - wahtever stood out… lemme og thorugh my notes and see… may be nothing…
bhhahahahha omg. Wait. there was one thing. THe fact this speaker guy said in casucal chat before the event started that he used to work at CHEWY. So you KNOW i’m gonna Ryan Cohen jabber with him. Lemme put those notes here. The rest was not useul for me:
This guy used to work at amazon and chewy. I asked him if he’d heard about Ryan Cohen looking to acquire eBay
He said from the headlines he heard, this sounds a bit liek “another gmaestop thing” - wasn’t interested in this. And I started explaining how they spent 2B on marketing to only get 1M new users. And how he can do the same. And cut down 98% on expenses. One guy said that means you cut people, and I said yea- and stores and wasteful stuff. I mean, it’d be pretty easy to cut 98% of marketing off 2B. LOL really.
He was like, uh, yeah idk how a 9b company will buy a 50b company. Omg haters gonna hateeeeeeeeee.
Okay this guy has 10 years of experience at Fortune 500 companies. He does two things with his company. Helps founders move faster with ai whether that means building something for you, or teaching your team to do it themselves.
LOL just feel like it’s so frustrating when people don’t want to talk about GameStop hahahahah ahhhhhhh.
So he wants to know who we are today?
How many use AI tools at least weekly
Who has paid for an AI subscription?
Who uses AI to write code or build something?
Who uses AI or customer research ro validation?
Who has an idea that they’re excited about but doesn’t know where to start?
Now this guy is going to share cause he’s serving nonprofits as an accountant. (This is the guy who was hating on the 98 expense cut) - broooo GAMESTOP WAS ABOUT TO GO O OUT OF BUSINESS. IF ITS A COMPANY THT IS ABOUT TO GO BANKRUP AND YOU CUT 98% OF EXPENSES AND SAVE IT - THATS IMPRESSIVE. WOULD YOU PREFER IT GOES BANKRUPT??????
Then he was earlier saying he approves of craigslist over eBay. Cause it has legacy. BRO EBAY HAS LEGACY omggggg.
And I was trying to tell them that GameStop will be verification stores, but then they just cut me off and changed the subject. UUGH.
Okay, I know this is not appropriate or modest, but whatever. I’m feisty about my favorite CEO and people not even LISTENINGGGGGGG
Okay the rest of the notes from the talk are here. But it was just another simple AI talk. here we go:
What is AI actually good at, and what it isn’t
So tehy have the first guy who worked 15 years as a sous chef and has an idea for a cheaper version of open table - they charge a large overhead, software and hardware. His idea is to make it more simple. Not just large companies owning the market. Woudl anyone pay before making any significant investment level?
Woudl you use AI to draft a cold outreach email to restaurant emails: NO - it sounds way too generic and like a sweep of the company. I’ve expereinced this NONSTOP hiring/interviewing my interns.
He says, no, he’s use AI to draft it.
Summarize what the negative reviews say - yes I’d use it although it’d miss nuance
Though bad language can trip up AI
Reviews are being gamed by actors (good and bad)
Decide whether TableKeep is a viable business idea or not - yes or no (no, it will always agree with you unless you work with it to really be critical)
Preset trained data, trained on weeks or months ago. Augmenting from a base set of data. It’s not scouting the whole internet. IT may have biases we are not sure about.
In this sense, AI is a relatively black box. We can trust I, but for augmenting we may not have the highest faith
Hallucinations also are a rabbit hole we don’t need to go down now, but you want to make sure there are sources for what it found
Final reframing: how do you think AI matters more than which tool you pick?
AI knows things, just ask: no ai predicts and synthesizes. It sounds confident even when wrong. Treat is like a smart assistant who needs fact-checking, not an encyclopedia
Its only useful if it gives me the final answer; AI is most valuable before the answer, brainstorming, pressure-testing, finding blind spots, turning messy thoughts into structure
It does the thinking for me - you bring the judgement and domain knowledge.e IT brings speed and breadth. T he best results come from directing it, not deferring to it.
“You are a startup advisor for a non-technical founder, I want you to provide critical help reviewing the market sizing opportunity, the pain points most seer with customers - give it a robust test. Give it a specific format like a 5-step plans. Name the tools. Give it a structured response. For better synthesizing in its own format what it’s trying to say.”
Is there stuff we can do to improve prompts? Don’t be general. Instead, have more details on waht you’re trying to accomplish, who they are, and what you’re looking for.
The synthetic customer: create paersonas, get structured feedback. Sory by what matters.
1. Define your personas
Give them tehe pitch
Let AI synthesize: across all 4 personas, what were the 3 most common objections? What woudl address all of them
View the data in different ways: rank all feedback points from most to lead imporant
How many customers of mine are impacted by this. What is the severity of the pain they feel?
There are aall sorts of manipulations taht you can do on that data, what is amazing is you can come out of it with insites that are synthetic and different personas than waht is outside of my head?
Passionate and you have to be to make it succeed.
Are there any unique customer types that you may create for your startups?
Who woudl you create?Entrepreneurial parents, random parents who want free time, kids themselves
Only 17 people here but he planned for 50 people. Yeah. Only 34% showed up. I feel idk usually it’s 40%.
Another tool to check out is bolt.new - describe your produce in two sentences. Get a hosted, sharable page in minutes.
His suggestions:
Bolt
Custom GPTS
Claude
Lol everyone knows most of these hahah. I feel like the AI world underestimates audiences.
But this bolt one can build front-end online. It doesn’t do anything, it’s just front end online. It’s a starting point to front-door test it. Not too much behind it, but a powerful tool to build onto of.
I brought up the “letsbuyspiritair.com” and maybe it was built with bolt?
WARNING - for some reason my blog GLITCHED OUT over letsbuyspirit and now that link is all over the place hahahaha. But i like the website, is has very like MOASS/Retail Investor vibes. So, enjoy trolling my blog, community spirit website. IDK what happened hahah.
He said maybe it was but with Claude code.
And Custom GPTs - yeah, it’s just like projects.
They allow you to input a set of information dn artifacts and it retains it int hememory then you can ask it anything about it.
I’m like wtf I use this all the time. I”m confused. I feel like idk what I need to be attending, but I’’m bot super caught up on AI but also behind - only cause like I talked to some programmers today who were talking me about how GSD is amazing, on GitHub.
He’s tell you to train it to sound more human, even to use typos. Repetive processes are a copy/paste away. You can define output, errors, everything.
He has one set up for daily news briefing to see what news he’d liek to see.
Using Claude projects at work and throw all the domain knowledge into each service.
Especially as you get into software development, super helpful as you want to see it broken out. Hugely helpful.
We are at time to end. He’ll finish up quickly and then be around for questions.
Okay so they made the website. They made a quick website in a matter of minutes. To publish it, it’s super cheap, maybe $1. They ou can use lots of tokens before hitting the cap. Powerful for proof of concept.
An audience asks why you like this over lovable. They’re all similar. He doesn’t know much about lovable, he used bolt a while ago.
I like lovable and have been to their local events.
This event was a bit of a commercial/sales pitch/inauthentic a bit. I just feel like that’s what happens when you work in corporate America. You get stuck in this mode of being palatable and agreeable and non controversial and media ready. But, not bad. Just not as cutthroat as I’d be looking for. Like I’m looking for super useful stuff. So, idk I use Claude code, I use the competitors to bolt, I use chatgpt/claude already - so I already use everything he suggests.
oh yeah! a girl who works at blackrock came up and interrogated me after the event hahhaha. i’m thinking: are you a spy? but we connected on linkeidn hahah she wants to know how i went from an ideas person to an entrepreneur and how I understand finance so well? and pick stocks, etc. I told her that basicalyl no one ever is interested enough to listen but if she’s interseted, i’d tel lher (you know? idk hahah if shes not a spy and wants to excape form her cray job, i’d be happy to help.
THE COACHING:
I took notes while we talked and will put a lot of it below. However, the night ended with me being asked out on a date. There are a few non-negotiables which are not met (like, I want to be with someone who is also sober and/or… equivalent to my heroes/role models in my instincts), so I’ll be honest with him and, yeah. If he wants to keep helping me and it’s mutually beneficial, I’d like to be friends. It’s good to spend time with people who challenge and inspire you. But, if that’s not enough… I guess this was our last official hangout!
also, i’ll add he welcomed and said bye to me with a kiss on my hand. lol.
Why do I want to help you? Cause you can’t teach heart. And you’ve got it.
Why am I helping someone with: with no tech plan, industry knowledge? - Inexperienced, naive?
BTW… I do think people really underestimate me and how much I know about business. I’ve self-taught so much over the years and even do a good job making money for myself. So. Idk. But its fine at this stage to be underestimated, maybe? I guess it has its benefits.
Pick up on drive.
Listening, following directions, holding, trying to get them to push through and follow vision.
First two things I need to launch this company:
(1) Plan to get funding
But honestly, idk if I want to get funding so full-fledged as my start. I keep waiting for moass with such certainty it’s going to pay off profoundly. So, part of me wants to keep bootstrapping indefinitely as my favorite CEO does his thing and my investments finally pay off
I just don’t want to be someone else’s investment. Or at least not till I know them very well. Lately I’ve just been surprised by many people, and glad I’m not in some sort of deal with them before knowing them well
Though I always think of Larry Cheng’s post about meeting someone (or interviewing them) at least 11 times before bringing them on the team. I see the value the more experience I get in this world. Friendship is one thing (that also should be cautious to dive too deep into) but definitely with business, even more patience is crucial. Time is an indicator.
(2) Good funder with a network
If you get into AiHouse, all edtechs are your friends, shoot the shit.
He said you get paid more if you have a co-founder and AI house is connected with the Wa state government. Then you’re in with the governor who is making the AI laws and then suddenly you need to make sure the edutech is completely legal. Go ask her, she wants kids to learn. Give her a free trial and let her try it and see it’s just good.
Know the process for how to get in. How to figure out the right door to fit into. They read your appearance from the start.
How to get the first round of funding to get hte ball rolling.
Hard limit to what one person can do. Can’t do ten bitches of work - this will need hundreds of thousands of bitches of work. (Being feminist by saying bitches instead of men)
Manually automate it
They’re looking at YOU - dont’ care about your idea. Need someone stable and professional.
once you get the money, you’re going to be boring, do exactly what you said, and then make a small profit then they will own
WRITE A ONE-PARAGRAPH BIO / FOUNDERS PROFILE:
WHO: Experience Shanghai quasi-celebrity life working for billion-dollar businesses. Perfect score on the Praxis Math exam. Back in the USA, mentored by a lawyer (Tenenbaum Law, LITAXATTORNEY.com) who had won hundreds of awards. Top 2% of lawyers nationwide, founding a kids’ financial literacy brand (friends with Hasbro, connected with Warren Buffett, etc). Won a few awards, nominated for others. Working to connect with multiple billionaire companies + change education globally. Starting with the USA. Cultural Revolution. 200+ industry events attended, taught 10,000 students. Pattern literacy thesis. Made money investing during covid, but scrapped that - even though I was good at it - cause i got so frustrated with financial corruption. Switched my thesis entirely and used my investments to fight back at the system.
Important to know you’re a cool person. Worth it as an investment. 100 people off the street who teach kids, I have a unique background that others couldn’t fit, smart, doing it.
WHAT: two paragraphs - you have till the time i get back to write two paragraphs. “I’m Warren Buffett… i’ll read this and then walk out the door if I don’t like it and never see you again. Try now - go!”
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Building an educational AI-integrated app that is the most fun 30 minutes your kids will have all day. Check in and take the class once or twice a week, following a map that slowly increases in difficulty as they master topics and learn. Students meet through a mobile app and a teacher is on the other side of hte screen. The teacher runs an interactive powerpoint that has games, music, AR, drawing, and so much more - all based around the content tehy’re learning. Topics may include entrepreneurship, public speaking, media literacy, content creation, and more.The AI tools will help enhance the students learning and bring their ideas to life. For example, a kid may want to say they’re building a lemonade stand with certain ingredients, teh AI will image-create waht that will look ike and play out different scenarios. Teachers will ovesee everything and monitor/enhance/inspire the students.
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I’m building an educational AI-integrated app that is the most fun 30 minutes your kid will have all day. They’ll check in and take the class once or twice a week — self-paced, following a curriculum that is gamified —gamified citric, increasing in difficulty as they master topics and learn. Students meet with the teacher on the other side of the screen. The teacher leads the interactive powerpoint that has games, music, AR, drawing, and so much more.— engages the platform to give curated lessons on music and shit — It’s all based around the content they’re learning. — set to their cirriculum. Topics will include AI, entrepreneurship, public speaking, media literacy, content creation, and more.The AI integration will enhance the students’ learning by bringing their ideas to life. ****For example, if a kid wants to host a lemonade stand with certain ingredients, the AI will image-create what that will look like and play out different scenarios based on their supplies, customers, popularity, aesthetic, etc. It’ll turn their ideas to life. Teachers will oversee everything and monitor/enhance/inspire students. Studnets will receive certifications at the end of each level completed and these can be posted by families on social media. Referrals, brag, you can get one too
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Building an educational AI-integrated app that is the most fun 30 minutes your kid will have all day. They’ll check in and take the class once or twice a week — self-paced, following a gamified curriculum. Students meet with the teacher on the other side of the screen. The teacher leads the interactive, curated class integrated with games, music, AR, drawing, and so much more. Topics will include AI, entrepreneurship, public speaking, media literacy, content creation, and beyond.
This is a dual economy platform, selling to teachers (hosting their classes) and students attending. It’s a virtual, educational ‘third place’ for families to create their own communities and connect over interests. The AI integration will enhance the lessons, bringing ideas to life. For example, if a kid wants to host a lemonade stand, the AI will play out difference scenarios based on their supplies, customers, popularity, aesthetic, etc. Teachers will oversee everything and monitor/enhance/inspire students. Students and teachers will receive certifications throughout, to use as bragging rights + to be posted on social media with referrals to join and get incentives.
After Attempt 1, he hugged me cause he was impressed (for a draft) and then we went, took me suddenly into antoher room, no explanation and showed it to someone in the coworkign space who gave feedback - based on that feedback i rewrote it
Attempt 2 (I wrote + he added feedback inside of it)then we talked and I rewrote it again:
THIRD ROUND: again, wrote but I was getting a bit worn out from the full day + intense focus so I didn’t want to do it again.
He also kept taking pics of me while writing these and told me to take off my jacket (so my skin was more exposed) idk just felt off. Like a mix of flattery with business/mentorship mixed into one. Sent them to me after, but it was a little violating/off. Its hard to put into words, but it just wasn’t consensual as a WHOLE like when you add it up with all the things, it was a number of things that were off. You’ll see throughout. It was like “access through superiority”.
He even complimented my chest at one point… it just sorta felt like a few awkward things I laughed off in the moment, but the more I write it out and reflect, it was being objectified while also mentored? idk.
I put my jacket back on after this cause I was cold, even though he said I shoudl keep it off because it looks nice, but idk. I felt exposed.
I won’t include everything else we brainstormed below - but most of it:
Creating an educational third place. Allowing them to create their own communities. They can open whatever convention they want if they’re paying the cut.
Make their own classes and sell them to each other
Yes this is what I’d been wanting to build before. So many teachers have amazing classes and I’m blown away by them and they need to be the gold standard / new normal. Not a standardized curriculum cartel lobbist normalized textbooks.
Platform hosting fee (long-term consideration) - fundamental documentation.
Marketplace idea - like Fortnite or Minecraft
Steam has 150 employees. Competition with Microsoft and Apple.
Power of scaling and selling to the community. Enable the community.
Kelly Blog - kelly moderator, admin.
Kelly Twitter space, who cares what’s posted as long as it’s not illegal.
Curated third places to integrate with a modern supplementary lifestyle. Becoming part of the kelly community.
Yeah all the time I say we need more third places. to build community, so we were on the same page.
Want to send stickers to students so tehy can brand their own stuff
An important part is to get them signed up for the monthly program.
Of course. Like the package-deal where you buy a few classes all at once or a year subscription - I’d written that down and knew this strategy from my past work at those billion dollar companies. lol. it works.
Monthly or yearly, 3month free trial to try it out. Want to become ingrained in their learning program. AI-friendly with kids make kids want to use it. Friendly AI interface. Non-universal. Make it so each class is designed so you’re talking with AI to do one thing. Each AI is single-purpose for hte class.
AI tells kids: I’m here to help you with the class, I’m not a real person, I’m not your friend. I’m pretending to be your friend.
Don’t treat AI like it’s people.
Empower 3rd space creation.
btw this is something like what i’ve been trying to biuld now for years. I wanted to build this with my own business and we were even working towards it but that business is on pause. So this was good to be reminded of.
Mass-producing Bill Nye videos. Using AI to Crete interactive Bill Nye experiment videos.
eh… idk. this I don’t agree with cause I think Bill Nye is part of the propaganda science psychop. But, I think more like what I was building and workign with in China.
Focus on the increased connection of student + lesson
and human.
Have ability for people to create their own educational series if they sign up as a teacher as well. You can charge them little for the cost - take a cut of their profits from them selling their classes. You are the AI provider + platform.
User-customizable AI interactive lessons
exaclty my point.
Can I be the marketplace and not the content maker - business standpoint: size of initial app? Size of app after brainstorming.
Recording every class and track all the data forever. And watch trends
20-second speech - then 2 minute goes back on all the main points
Next time you meet someone, be ready to pitch to them, assuming they have money and want to give it to you
lol. maybe. idk i dont wanna rush this too much, though its fun to talk about. but i wanna build it out.
You have to lead the dance, if they lead they have control.
You need to lead - but you need to be in control .
Everyone will want to get a percent of this.
AI startup entrepreneur.
Watch highlights of Silicon Valley.
Technical specifications, basic stuff.
AI to hold me accountable.
Ai powered con-bon board - gyro tickets - agile
Landing site, technical specifications, need to know everyhting about AI and look at everyone else doing EDU AI. 90% is copy/pasting what they’re doing right and what you could be doing better.
PLAN:
Figuring out what I need to build
How to finance it
How to know what to build
Know how to know what I need to be financed
Who/what types of people do I want help from? Want to recruit
What are the competitors, what are they doing?
Make a landing page
Summarize/master my 20-second + 2-minute pitch
Make a white paper
10 . Have fun every step of the way.
+ Pro Forma (how does it make money)
INTERNS TO DO:
Landing page
Social media accounts created
I feel this is way too soon.
Name of it — url?
he wanted to name it right then and there, but I don’t wanna force some stupid name out.
Social media manager
Good tech guy for the back end
Tech guy to come up with a front end plan
Another educator to start writing up a basic curriculum that you just give for free to show everyone the power of lessons.
CODE NAME: fake name for hte project then later have it? Maybe
He will email me an example of how to use a shared Google Docs with all interns.
Later, he was smoking weed in the room, and someone caught him but he played it off like that other person was delusional, then distracted them to give business advice. Even anohter random person just said, “it was probably smoke from someone’s food” which we both kinda laughed about later. After, we walked to go get food and he found a knitted rose on the ground and put it into the breast of my coat and then at the chest of my dress without my consent.
And then later he came and sat on the same side of the table as me so we coudl be closer. Bringing up longboarding and how I should try. I told him i recently fell off a scooter (which is why I don’t want ot long board even though he pushed it on me many, many times) a few months ago and it still didn’t heal, so tehn he grabbed onto my bare knee and felt it for a while. Just a few boundary violations I wasn’t super cool with. Just felt a bit off. You know? Like he felt the right to keep touching me and do what he wanted with my body when the feelings weren’t mutual. I like him on a business level, but he kept overstepping.
OVERALL TAKEAWAYS: A lot of this was useful, but taking a few hours away and looking at it again, there are some things that I like the way I’m going and, yeah. Idk. I do and don’t want to rush this.
I want to make something great, I’ve got people helping… so, just gotta keep going. Idk. Just feels like a lot at once
And the idea/push to make this new initiative my ‘full-time job’ and focus (he even said I’d need to give off the vibe to investors that i’d sell my daughter in exchange for more money… that really turned me off to a lot. no way.)
I’m working hard to build my normal Kelly Tutors, too, with my interns. Even though he made fun of me for having interns and said they’re a distraction, I think its the COMPLETE opposite.. tehy’re inspiring, empowering, and TOO helpful - its mutually amazing.
I love this that I’m building with Kelly Tutors, with my interns. It’s amazing and I feel its all coming together, so I want to keep that rollign while also start to build up momentum with this platform as well.
I’m grateful for the guidance and/but wanna also keep doign things my way cause they’re working. And I love my daughter and being a mom and I value my time with her so much.
Plus, I’m diversified. Especially will be good if/when moass :) I just know I am good at making my own money - big money, and I’d rather not be dependent on anyone I don’t know well.
And even I tried to tell him (and that other guy) about my MOASS thesis’ and values and it was sorta brushed over. I just think thats my heart and soul, you know? Its my values in real time. So, I want to work with people who are good listeners and just authentically interested in what I have to say.
I’m my own Sean Kingston. I’ll take myself there. I’m an AMC/GME/BBBYQ ape. Cue “take you there” (music video below).
Until next time, I wish you the motivation and success to search for opportunities around your area. Search and explore: Who is out there giving talks? There are new things happening all of the time.
Find relatable or interesting topics you like and check them out! Maybe even something hosted at a cool venue, if there’s no other reason to go. Let’s see what you can learn and discover not too far from home. 😊
