Through the Looking Glass
Stephen Klein's Quest to Make AI Think Before It Speaks
Written by: Phoebe Gill Photography by: Irina Logra
Editor's Note: This is a friendly reminder that the ideas expressed by the interviewees are not necessarily the thoughts of HubSpot, its offices, or its partners. HubSpot is committed to exploring and sharing ways our customers can better utilize AI tools. That said, there are a lot of provocative takes about the topic worth tackling and discussing. We hope this article will give you a framework for having a fuller and nuanced look at AI and how to implement it in a way that works best for you.
Summary
- Stephen Klein, who founded fintech startup LOYAL3, is now building Curiouser.ai, an AI coach designed to ask thought-provoking questions rather than provide answers.
- Klein vocally challenges Silicon Valley's AI narrative, calling "agentic AI" nonsense and warning that automation leads to commoditization, where everyone becomes average.
- After teaching at an underprivileged high school, Klein became passionate about democratizing critical thinking tools.
- Curiouser.ai operates counter to industry norms with a team that's 86% women and a business model focused on augmentation over automation.
- Klein's three goals reflect his unconventional approach: elevate humanity, create wealth, and build a model diverse company.
Introduction
"Agentic AI is 100% Non-Sense Designed To Scare You Into Spending Money on Consulting."
That was the hook of a LinkedIn post designed to ruffle feathers in the AI world. It was bold, direct, and very Stephen Klein.
One quick scroll through your phone shows a media landscape dominated by incredulous promises about AI changing the world. But scroll a bit further and you might come across Stephen Klein, a beacon, holding firm to his values, questioning the big AI companies, and approaching artificial intelligence with a deeply human-centered mindset.
While most of Silicon Valley is busy building AI companies designed to automate and replace jobs, all in the pursuit of profit, Stephen is purposely, loudly, going against the grain.
He is the founder of Curiouser.ai, a startup building the world’s first strategic AI coach, Alice, designed not to answer your questions, but to ask them.
And not just any questions, thought-provoking, Socratic, destabilizing questions.
Welcome to Alice in Wonderland. And Stephen, like a modern-day Lewis Carroll, is inviting us to question everything.
Down the Rabbit Hole
Stephen Klein has had an interesting, varied career path. He didn’t set out as a teenager to work in tech, and he certainly never planned on being in AI. His is an inspiring story of becoming an entrepreneur later in life, a refreshing contrast to the usual lineup of impressive yet pubescent founders.
Originally a chemistry major in college, Klein fell into advertising after graduating. He then spent the next few decades in high-level marketing roles, flying around the world for work.
Later, wanting to fulfil a lifelong dream, Klein applied to and was accepted into Harvard Business School, and that’s when everything started to shift.
It was at HBS where Klein was taught how to learn. Not memorize. But really learn. Learn to question, deconstruct, rebuild.
He fell in love with entrepreneurship and jumped straight in. During a finance course at Harvard, he had an idea that led to the founding of LOYAL3 in 2008, a pioneering fintech startup that allowed everyday people to invest in top brands via IPOs, stock rewards, and fractional ownership.
It was about democratizing finance, leveling the playing field, and creating opportunities — a thread that has run through Klein’s work ever since.
From 2015 to 2021, Klein returned to his roots and headed up marketing and innovation for the world’s largest law firm, Dentons, with over 16,000 employees across 75 countries. It was part branding and marketing, part systems design. Klein developed infrastructure and platforms that let people share innovations globally and drive revenue.
While at Dentons, he also began speaking around the world, inside the firm, to clients, and to legal communities, about the risks behind AI and automation.
“I was given an opportunity to travel all over the world and speak on AI ethics.
And so I was considered an expert on the topic, which is not really valid. I don't know if anyone's an expert on the topic, to be honest, but I knew a lot.”
He continues, “I was able to speak to clients and lawyers within the firm, as well as independent law firms all over the world, and talk about the ethics around artificial intelligence, data bias, the things that could go wrong, what we need to be careful of.”
Fast-forward to today, and Stephen is now building his own company while still teaching entrepreneurship and marketing at UC Berkeley. Teaching is a passion of his, a way of giving back that he describes as central to his life.
Though Stephen may have spent decades in the corporate world, it’s clear he never found much fulfillment from that work. In contrast, his current multi-hyphenate career carries a real sense of purpose across every role. He works pro bono in the Bay Area, helping nonprofits with strategy and planning. One close to his heart right now is Poetic, a Dallas-based organization supporting sexually abused girls.
”I do quite a bit of work to help them around strategy, programming, funding and so forth,” he says. “That's a labor of love.”
It’s the same meaningful work philosophy that is at the core of Curiouser.ai, the company he now leads, with a team that’s 86% women.
Curiouser.ai has now been in development for over two years. And right from the very beginning, it was built to challenge the status quo.
“We are one of the few companies out there dedicated to helping people think,” Klein says, contrasting Curiouser.ai with the standard AI business model where automation and speed rule.
“We are an augmentation model, a partnership model in which we elevate people's ability to think critically and be more creative.”
We’re All Mad Here
A core part of Stephen’s personal brand is built on disrupting the AI Tech Bro narrative currently dominating the media.
According to Sam Altman, AI will soon replace entire industries, and the world as we know it is going to change beyond recognition.
And while most people in AI conveniently gloss over the very real limitations and accuracy issues plaguing automation tools, Stephen is consistently drawing attention to them. And to a rapidly growing following on LinkedIn. Personally, I like to think the tide is starting to turn, that maybe people are waking up to the reality of AI, and how it might not be all it’s cracked up to be.
According to Stephen, of course it’s not.
“It's unreliable. The error rates are getting worse as the models get more sophisticated, 30 to 70%. And the AI doesn't think. It doesn't have the ability to imagine or create. So, yeah, maybe you're gonna save some short-term money and boost profit, but you're not going to basically perform or create more value over the medium to long-term.”
Stephen calls it the “Hype as a Service” economy, drawing parallels to the dot-com bubble. Too much money, not enough sense.
In the past few years, Silicon Valley has been flooded with cash, investors racing to build the next ChatGPT, selling cost-cutting dreams to CEOs while quietly ignoring the people whose jobs they claim to replace.
The “Hype as a Service” economy promises that automation will slash headcounts and inflate margins. Never mind the millions of workers left anxious about their futures.
Stephen’s message, though, is clear: behind the glossy marketing, the narrative just doesn’t hold up.
“Most of the companies that have done that are already hiring people back; bringing them back because somebody has to manage the AI's inaccuracy quality issues.”
Like politicians out of touch with reality, the people who make the decisions to implement AI-tools are not the same people left to work with these tools. And as companies start to realize that AI tools aren’t quite the productivity-boosting, margin-expanding miracle they were sold, they’re quietly reversing course.
Beyond the question of accuracy, there’s another looming issue - commoditization. It’s a threat that affects everyone, from enterprise giants to tiny startups.
In a recent AI podcast, Inside Analysis, Stephen explains that when everyone is using the same prompts on the same models, trained on the same data, you end up regressing.
Innovation becomes imitation.
“At any one moment in time, 100,000 people are basically inputting a similar prompt to you, because the businesses are often similar, and they’re using the identical database, and the identical tool.
When I say, regressing to the mean, I mean, literally, you are becoming average.”
Curiouser and Curiouser
You might be wondering how on earth someone like Stephen could possibly be an AI founder with this sort of attitude; but he is.
Introducing Alice, the flagship product of Curiouser.ai.
“Rather than being educated, or trained as a model to perform tasks, which is what 99% of the generative AI is designed to do, perform tasks, make things easier, perform tricks.” Stephen explained, “Our generative AI is actually designed and educated to ask you questions. Her name is Alice, Alice in Wonderland, and that's sort of the origin story. She doesn't slow you down. What she does is challenge you to think more deeply by asking you some very deep, important epistemological questions.”
Unlike other models, Alice is deliberately not connected to the internet. Instead, she’s been trained in Socratic questioning, engineering design, and the “Five Whys” methodology first developed by Toyota in the 1930s.
And that’s where Alice shines.
According to Stephen, while ChatGPT and Claude are busy mass-producing generic content and turning marketers into clones, Alice is a refreshing alternative. She’s an augmentation tool, a brainstorming partner for strategy, designed to deepen your thinking rather than flatten it.
Stephen has spoken in multiple interviews about his ambition to turn every CMO into the next Steve Jobs for their company.
This philosophy of empowerment might have started years ago, when Stephen took a year out to teach in an underprivileged high school. There, he was struck by the genius of his students.
“I started realizing, you know, how many Mozart's are out there that have never been given a piano? I think it's that simple. You know, what if Mozart didn't have a frickin' piano? Or Lewis Carroll didn't have a frickin' pencil?”
Maybe that was the original seed of Alice?
The Queen of Hearts’ New Rules
Unfortunately, when it comes to AI and ethics, according to Stephen, “There’s no such thing,” he goes on, “There’s only the ethics of the people who build it. In other words, does the CEO stand for certain values and principles? And what are they and will they declare those? For most of Silicon Valley, ethics is just an inconvenient speed bump. Something to deal with quickly via a glossy PR campaign, then move on.
“We’re serious businesspeople,” Klein mimics the industry attitude. “Don’t slow us down.”
But for AI to be truly ethical, he argues, it has to be baked into the process.
“You've got engineers, you can have philosophers, linguists, artists, writers, who can all go into educating and building an AI. So, I would argue that ethical AI is part of the design and manufacturing process, which is human-centric and organizational. And if you can't have the discussion without thinking about whether or not that organization is ethical, has values, is principle-based from the inside out, from the ground up. It's just a waste of time.
“The technology doesn't have a clue what ethics are. A robot would just as soon go out and kill people as save lives. It does not know. Right now, ethics is basically discounted and the conventional narrative is sort of an annoying academic topic when it comes to the industry. Companies are building profit-driven AI with little to no regard for the consequences. Human greed is once again, at the crux of the issue when it comes to ethics and AI. A few select people at the top getting rich.”
Stephen goes on to point out other issues, “90% of all the internet has been basically used by five generative AI companies to train the models. That's a fact, they're all in court now.”
It’s a worrying thought, a world where lawsuits over copyright violations are just background noise. One where government regulation can’t and won’t catch up, and frankly doesn’t want to.
It’s scary, and sadly, it looks like it’s already our reality.
So, how can a company remain competitive in this post-IP, post-regulation world? Stephen, apparently, has the answer.
“I would argue that values and ethics will become the strategy of the future; shared values with your customers, your employees, and your stakeholders that realize that you stand for something. And it's not a poster on the wall; it's really something. If, in fact, that is true, there's no stopping you because that is an impenetrable mode. Because I will never, ever, ever leave you as a customer.
“If I believe in you, you believe in me, you treat me fairly. So I would believe ethics is actually going to become the significant competitive advantage, and shared values are going to become the strategy of the future because just about everything that can be measured is going to be automated.”
Klein believes shared values will become the moat of the future. Not flashy branding or features, nor IP. But principles, real ones, lived and breathed by the company that connect with customers.Ethics and humanness, he argues, won’t just be part of the conversation. It will be the only competitive edge left.
Which Way? Which Way?
Although Stephen acknowledges we’re still in the early days of AI, he believes we’ve already reached a fork in the road.
One path has companies chasing speed, scale, and short-term wins. It’s the automation route, profitable in the short term, but ultimately hollow. Fraught with inaccuracies and resulting in companies rehiring the very same workers they replaced, to “babysit” the AIs.
The other path is slower, harder, and many would argue, less profitable. It’s about consciously choosing a human-focused approach, developing AI to augment rather than replace.
There’s no prize for guessing which path Stephen has chosen. He’s betting that, eventually, human nature will choose meaning over momentum.
Until then, there might be some rocky roads ahead.
The rapid success of China’s Deep Seek has proven how quickly foundational LLM models can be replicated at a fraction of the cost, fueling a race to the bottom.
In response, Stephen suggested on the recent podcast episode, Inside Analysis, that a certain few American AI companies aren’t pushing for regulation, but financial aid from the government.
Hinting at a possible federal bailout happening right now.
Stephen isn’t sure what will happen after the correction, but he knows that only the companies with substance and meaning will be left standing.
Finding Your “Why” in Wonderland
Perhaps, that’s part of the reason Stephen speaks with such conviction.
The mission behind Curiouser.ai goes deeper than money. It’s about rediscovering human potential and rediscovering the imaginations we all had as children.
Stephen references a NASA study that found that 98% of children test as creative geniuses, but by adulthood, that number drops to 1.5%.
Stephen wants to reverse that trend. He’s trying to help people think more deeply, act more intentionally, and reclaim the creativity many of us lose as we grow up.
The goal at Curiouser.ai isn’t to scale the company at all costs for a quick profit. It’s transformation. It’s one of the reasons why there isn’t a free trial, instead, at time of writing, it costs $5 for two weeks.
He believes that Alice could be the key to helping more startups succeed. Currently, over 90% of new companies fail, and Klein believes that if Alice can help founders sharpen their thinking and avoid costly missteps early, the ripple effects could be massive. By helping just one more percent of startups succeed could mean the creation of 150,000 new jobs.
And it’s not just startups. Klein teaches the same ideas in his courses at Berkeley and brings them into his nonprofit work as well. Whether it’s mentoring students, advising social impact orgs, or speaking about AI ethics around the world, the throughline has always and will always be the same: giving back and helping people.
Writing this article, I can’t tell you how refreshing it is to come across an AI-tech founder sticking to his beliefs and building for the greater good.
Stephen Klein doesn’t want to be part of the AI hype machine. He’s building something deeper, closing the interview with one of his favorite sayings, “The trick with technology is to avoid spreading darkness at the speed of light. Let's spread some light here.”
We’re Painting the Roses Red
Part of Stephen’s charm comes down to his age. At a time when others are thinking about retiring, Stephen is like an ambitious teenager, genuinely trying to change the world.
It’s as if the world hasn’t worn him down yet; unjaded by greed and money, Stephen is driven by three main goals.
“Goal number one is to change the world and elevate humanity so that we can leave a better world for our children in the next generation. And that's what I'm doing and why I'm doing it.
“Goal number two is to basically create wealth, create a lot of wealth.
“Goal number three is to build a model diverse company that I believe in.”
While most of the AI industry is busy turning us into clones without us noticing, there’s Stephen Klein in the corner. He’s courageously cheering us on, believing in our potential to be creative geniuses, excitedly looking forward to what we can create.
Writing about Stephen and the Curiouser.ai team has made me feel something I haven’t felt in a long time.
Hopeful.
Image in the public domain. Illustration of "A Mad Tea Party" in chapter in Lewis Carroll's Alice's Adventures in Wonderland in which Alice meets the Mad Hatter, the March Hare and the Dormouse.
Author: Phoebe Gill
Phoebe is an SEO specialist, content marketer, and host of The Beginner's SEO Podcast, based in Sydney, Australia. She spent her twenties traveling across South America before settling in Sydney, where she’s spent the last seven years helping businesses grow. When she's not talking or writing about digital marketing, you’ll likely find her at a dance class or soaking up the sun at one of Sydney’s many beaches.
