Every CEO says they are customer obsessed. That sounds right. It also hides a failure mode that shows up once your early product starts working.
Trip Adler put it bluntly: “You do want to listen to customers and you want to build based on their feedback. But at the same time, you can get caught in a loop where you’re just constantly listening to your best customers and just solving for them.”
That loop feels productive. It can also shrink your ambition without you noticing. You end up building a better version of what already exists, instead of creating what the market will need next.
Trip ran Scribd for nearly 17 years. He lived through long cycles of product shifts, monetization tension, and platform evolution. Then he did something most founders do not do. He immediately started again, launching Created by Humans to tackle copyright in the world of AI.
His lesson for CEOs is not “listen less.” It is “lead more.”
Experiment Like You Have No Budget
Trip’s first revenue story is not a growth hack. It is a mindset.
In Scribd’s first year, there was no revenue model. So he went outside the office and played saxophone for money. “We just joked that that was how we make money because we didn’t have a revenue model at the time,” he said. “That was kind of our ongoing joke, but that is how we made our first revenue.”
Most CEOs lose that muscle as soon as real funding and real metrics show up. Trip sees it as a permanent job requirement. “As a CEO, you want to always be experimenting,” he told me. “Trying things, putting yourself out there.”
The point is not saxophone. The point is staying willing to do things that feel weird, scrappy, and slightly irrational if they move the company forward.
Don’t Forget What Made It Work
Trip believes the biggest blind spot is not strategy. It is distraction.
As companies grow, CEOs get pulled toward process. He lived that drift himself. “I remember as I was growing the company, getting really focused on things like what are the company processes and management structure and performance review plans,” he said.
He paused, then gave the warning every scaling CEO needs to hear. “That stuff’s important, but I think a lot of CEOs probably lose sight of just making a really good product and just serving customers.”
The problem is not building structure. The problem is letting structure replace the work that made the company matter in the first place.
If you are scaling fast, you need systems. You also need to “stay true to what got that company started” as the company scales.
Culture Is Not Something You Fix Later
Trip did not treat his new company as a continuation of the old one. He treated it as a chance to design with intention.
Created by Humans started with what he called “a really big mission,” aimed at solving “how copyright works in the world of AI” and “how human creativity and AI are going to coexist in the future.”
Big missions are motivational. They are also filters. They help you decide what to build and what to ignore.
Trip also talked about culture in a way I agree with deeply. Culture forms no matter what. The only question is if you shaped it on purpose. “When you build a company for 17 years, the culture grows and changes over time,” he said. “It sometimes changes in ways that are somewhat accidental that you didn’t really intend for.”
Starting from scratch gave him a reset. “You can really be very thoughtful right from the beginning about how you want the culture to be,” he said. “You can design that culture from day one.”
Delegate, But Don’t Disappear
Trip described the CEO tension that never goes away. You have to delegate to scale. You can also delegate yourself out of relevance.
“It’s possible to delegate too much,” he said. He believes “the best CEOs are involved down to the smallest details of the company. Because those details really do matter.”
That does not mean micromanaging. It means staying connected to the work where quality, customer experience, and execution live.
He framed it as a moving balance. “It’s a constant tension between how much do you want to delegate and how much you want to stay in the details,” he said. “It changes year by year and depending on what the company needs.”
Your job is to sense when the company needs surgeon mode and when it needs architect mode.
Know When To Lead Customers
Here is the core insight Trip shared, and it is uncomfortable for many CEOs.
Sometimes your customers are right. Sometimes they are early. Sometimes they are loud. Sometimes they are narrow.
Trip’s warning was precise. “You can get caught in a loop where you’re just constantly listening to your best customers and just solving for them.”
So what do you do instead?
“There are times where you want to make a more visionary leap,” he said. “You say, sure, our customers want this, but we need to take this to the next step. And you just push that vision through.”
This is where CEOs earn the job. The company gets used to filing customer requests and shipping them. Then you ask it to follow you into a leap that is not yet proven. Trip said that part out loud too. “It’s often challenging to bring the company along,” he said. “It’s a little bit startling for folks.”
The answer is not charisma. It is commitment. “You need to have vision and you need to commit to it and you need to have perseverance,” he said. “You just sort of go for it.”
Where Vision Comes From
Trip did not claim he is magically smarter than customers. He described the structural advantage a CEO has.
“You’re spending a lot more time thinking about your business and the problems,” he said. “Your customers aren’t really thinking about it. They’re using the product and they’re just coming up with ideas.”
The CEO sees friction customers cannot see.
- Business model constraints
- Partner dynamics
- Supply chain or rights issues
- The system that needs to change for the next phase to unlock
“If you’re full time on a job and you’re thinking about it all the time,” Trip said, “you’re going to come up with insights that your customers are not going to come up with.”
He sees it as a responsibility. “It’s your responsibility as a leader to take the lead and show your customers what they’re missing.”
That is the real job. You listen. You synthesize. You decide. You lead.
AI Is The Problem And The Tool
Trip’s new company is built right at the fault line between human creativity and AI.
Created by Humans is building a marketplace connecting rights holders and AI companies. He described it as building “a model that continues to support the business model around creativity.”
They started with books because books sit at the center of the current conflict and because Trip has deep experience there. He also laid out a clear framework. “We created the concept of AI rights,” he said, then broke it into three categories:
AI Rights Categories
- “AI training rights”
- “AI reference rights,” which he described as using books for RAG
- “Transformative rights,” taking human work and transforming it using AI
Each category is “a whole different animal,” and the company is building around those distinctions.
Operationally, Trip is not cautious about AI. “Our perspective is to use AI as much as possible,” he said. He uses it as a thought partner. His team uses it heavily in engineering. “The vast majority of our code is now written by AI,” he said. “It seems like the engineering team is vibing more than anything these days.”
He also hinted at product work coming soon. “We’re also building AI products,” he said, “a lot of really cool stuff in the works that we haven’t announced yet.”
What This Means For You
Listening is not leadership. It is input.
If you only build what your best customers ask for, you will win their applause and lose the future.
Trip’s story is a reminder that scaling requires two different muscles at the same time.
- Stay scrappy enough to experiment
- Stay disciplined enough to protect what made the product matter
- Stay close enough to details to keep quality high
- Stay bold enough to make a leap that customers did not request
Listen to the full episode of The Scaling CEO here.
I am Glenn Gow. I coach CEOs. If you are trying to balance customer pull with real vision, and you want to scale without getting trapped in the loop, let’s talk.
