What If You Spent One Year Learning Something New? | Ravi Gupta

His first business got shut down by his school

I often start by asking guests about the first entrepreneurial thing they ever did.

Ravi had the standard kid businesses: mowing lawns and shoveling snow. But his first distinctive one involved a Memorex CD burner and the music people wanted to hear.

He was selling burned CDs in high school.

File-sharing sites sometimes gave him access to albums early. He could put the music onto a disc, and other students would pay him for it. He did that from roughly sophomore through senior year, until his school found out and made him stop.

“This all sounds super illegal,” I told him.

He called it his first and last illegal job.

There you go. A little entrepreneurial origin story with a school intervention.

When I asked for his first legal example, the answer moved pretty quickly from CDs to Ghana. In college, he started nonprofit work that included building schools and helping establish a debate program for women there.

That mattered because most of the scale in Ravi's career has come through nonprofits. He described a school network with a budget around $100 million and a political training organization operating in the tens of millions annually.

His for-profit projects had been much smaller. He mentioned health and fitness work and an education business helping people write books. He also said he had a bigger startup in development that wasn't public yet.

I didn't get details on that startup, and I'm not going to fill in the blank.

But the education business caught my attention immediately. I run a book publishing company. If somebody says they're helping a group of people write their books, I want to know how that works.

A Wednesday writing class that turned into more work than he expected

Ravi's program is called Analog.

As he described it in our September 1, 2026 conversation, people working on different kinds of books met with him on Wednesdays for a three-hour class. He coached their projects, taught writing, and helped them think about some of the things an agent might help an author think through.

The cohort had started in the first week of January. The intended finish line was the end of the year, with many drafts likely coming together around Thanksgiving. Some people had already finished a draft when we talked. Others would need the whole year.

So I asked whether this was the first year he'd done it.

It was. And he was pretty candid about the experiment.

It was taking way more work than he'd expected.

He wasn't sure he would run another cohort, especially with that larger startup potentially becoming an all-in commitment. He had started codifying how he taught writing, but that didn't mean he'd already solved how to make the whole thing fit into his life.

I appreciated that answer. A program can be useful and still cost its creator more time than they planned.

I'd thought about doing something similar: get a cohort of people who need to write a book, walk them through it, and write a book alongside them. I'd be doing the homework I was assigning.

That part is compelling to me. You aren't just telling someone to get through a difficult creative process. You're working through it too.

Then we talked price.

Ravi said the normal price was $400 a month, which he described as roughly $100 for each three-hour class. He also offered full scholarships for people who couldn't afford it.

My reaction was pretty immediate: That is an incredible deal.

If I start a cohort, I told him, it isn't going to be that cheap.

He laughed about the possibility of future price inflation, but there was a real reason behind the initial number. When he's new to charging for something, he can feel embarrassed asking for money. He wants to know the thing works before he asks someone to pay much for it.

His price was partly a way to make sure that even if he face-planted, he could still give people their money's worth.

By the time we spoke, he felt much more confident about the program.

The confidence had changed. That got me wondering about whether the price should change with it.

Those prices and his uncertainty about continuing are part of the interview as recorded. If you're looking at Analog now, check its own page for the current cohort and terms.

Price can change whether the homework gets done

Pricing is one of those problems entrepreneurs keep running into.

You can go online and find somebody making a confident case for almost any number. Meanwhile, you still have to pick a price and tell an actual person what it is.

I told Ravi I generally lean toward pricing high.

One reason is that price acts as a client filter. If somebody spends a meaningful amount of money on a service, they're often more committed to getting something out of it.

Another possibility is that you're serving someone for whom the price is a smaller fraction of their resources. In that case, they still need to see a clear path from working with you to an objective they care about. Having money doesn't make the objective disappear.

I also don't think charging a high standard price prevents you from offering scholarships. You can choose to help somebody you really want to work with who can't afford the normal rate.

That's a model I'm comfortable with, especially when I'm offering something I've spent years getting good at.

Ravi brought up a difficulty he'd seen with scholarships. In his experience, the attrition rate was higher among people who hadn't made a financial investment.

He also made a point of saying he'd had amazing scholarship participants.

That exception belongs in the conversation. We weren't establishing that somebody with less money is less committed. We were talking about a pattern he'd observed and one possible reason for it.

For a service business, this becomes very practical.

Sometimes you can do your part perfectly and still fail to get the promised result because the client hasn't done their part. They have to give you the information, make the decisions, or do the homework.

I joked about increasing the “obedience” of your clients.

If I pay a lot of money for something, I'm going to freaking do the homework.

That's the behavior I was talking about. The financial commitment can make the next assignment feel harder to casually ignore.

It doesn't mean you can slap a giant price on something and automatically create a great client experience. The work still has to be useful, and the person still has to understand what they're buying and what they'll need to do.

But Ravi's original question had been, essentially, “How do I charge fairly while I'm still proving this?”

My question was becoming, “Now that you've proved more of it, does the original price still serve the work?”

He said it was something he should think about if he did the program again.

Learning to write when AI can write something for you

Then I took us off the path I'd planned.

What's your attitude toward AI when it comes to writing?

For that cohort, Ravi wanted people to learn to write without it.

He was teaching a skill. If the point is to get better at writing, outsourcing the writing creates a pretty obvious problem.

But his answer wasn't that every tool use was identical or that people should be ashamed to discuss it. They were working through the distinctions in real time.

What is Grammarly doing? What is a system like Claude or GPT doing? What changes when you ask it to copyedit something you've written versus generate the text?

He also talked about AI detectors as one of the things they discussed.

Ravi said that when people wanted to use AI for something, he wanted them to bring it up so they could talk through how they'd used it and whether it was improving their writing.

That seems like a much more useful conversation than everybody quietly pretending the tools don't exist.

He used an analogy I wasn't expecting: steroids versus Botox.

If you're writing in a competitive environment, pursuing literary prizes, for example, you may think about AI assistance as a performance advantage that changes the competition.

If you're writing a general-interest book to be understood, you might think about it differently. In that case, he said, the tool can be more like cosmetic assistance. Something people feel bashful acknowledging even though it's widespread.

That's Ravi's analogy. You don't have to love it to see the question underneath it: What is the purpose of this particular piece of writing?

If the goal is to help the audience understand something clearly, he thinks using available tools to improve clarity and storytelling can make sense.

At the same time, he wanted his students to develop the underlying skill. Then they could bring an actual writing ability to whatever tools they used.

I told him I'm still wrestling with this myself.

I use AI a lot. But I don't love the thought of using AI to write a book.

Copyediting feels different to me.

Ravi thought we might eventually talk about books in categories: fully human-made, AI-assisted for copyediting, and other combinations. That was his prediction, not a settled publishing system.

He also argued that AI was already a better copyeditor than many people. Again, that was his view. We didn't test competing editors on the show.

What made the argument more interesting was his own publishing experience.

He said Penguin Random House had given him an excellent editorial team and three rounds of editing. That kind of support costs money. Most writers don't get access to a whole team like that.

So if a tool can help someone clean up their work, why close that door to them?

I was with him on that use.

Then I brought up another one: dictation for your vomit draft.

Your first draft doesn't have to arrive as polished paragraphs. Sometimes you need to talk your way through what you're trying to say. If a tool helps turn your own spoken thinking into a usable rough draft, I can see that being helpful.

Ravi had recently torn a biceps tendon while surfing and couldn't write normally for a couple of weeks. He'd used a voice-dictation program for much of that period.

He wasn't claiming he'd dictated some enormous new manuscript during the injury. He specifically said he hadn't been doing significant writing then. But he had experienced how useful the tool could be when typing wasn't available.

We kept coming back to the purpose of the work.

Are you trying to learn a craft? Communicate an idea you already have? Get a messy spoken draft onto the page? Have something else generate the prose?

Those deserve more specific answers than one giant yes or no.

Why my phone now stays downstairs

That discussion turned into a question about whether people will keep reading.

Ravi wondered how important the written word would be 50 years from now. He didn't know. He wouldn't be surprised if it became less central.

I could relate to the worry without needing a forecast.

When I became a regular YouTube watcher, reading went out the window.

There are still plenty of book nerds. I like book nerds. But I was talking about what had happened to my own attention, and I don't think I'm the only person who's had that experience.

Ravi explained that he'd leaned into memoir in The Invisible List. Each chapter takes you through a year in which he's learning something: surfing, training for a powerlifting competition, going to Italy to cook.

He wanted the reader to go on the ride with him and learn through the story.

That gives someone a reason to stay with a book beyond extracting an answer. You're following a person through time, watching things happen, seeing what changes.

I told him about a small change I'd made recently.

My phone doesn't come to bed anymore.

It stays downstairs. My bed is upstairs. Those two things no longer spend the night together.

That means I need something else to do while I settle down to sleep. Usually, for around an hour, that thing is reading a physical book.

It scratches some of the same itch as reaching for the phone. There's something interesting to pay attention to.

But the experience feels fundamentally different.

With technology, it feels like every piece of it is either screaming or quietly whispering that there's something else I might be missing. Hey, look over here. You'd be a dummy to ignore this.

A book feels more like a comfortable journey.

Ravi said it calms your brain. That matched what I was describing about my own evenings.

That changed when the phone stopped being the easiest thing to pick up.

And it connected directly to his memoir idea. You can spend an evening following somebody else's story without constantly being pulled toward 30 different things.

What he means by civic entrepreneur

At this point, I admitted we'd gone pretty far off the rails from what I'd planned to ask.

So I came back to a phrase in Ravi's bio: civic entrepreneur.

What does that mean? How is it different from conventional entrepreneurship?

For him, it describes the common purpose behind the things he's built.

Some have been nonprofits. Some have operated in the political world, with its own kinds of organizations. His media work has crossed different business structures.

The thread is improving civic life.

He gave several examples. Schools were about educational institutions. Arena was about the political system. The Branch was about the media ecosystem. Second Chance Studios helped people coming out of prison get jobs.

He hadn't necessarily set out with one neat label for his whole career. Looking back, though, he could see the pattern: the way people build shared institutions and make democracy work had been a continuing passion.

That's a useful distinction if you're trying to understand his version of entrepreneurship.

The organization can change. The problem he's interested in keeps showing up in a different place.

I asked which of those organizations came first and how he'd built it.

That took us to Tennessee.

Building a school at 26, after a Saturday in Harlem

Ravi moved to Tennessee at about 26 and started Nashville Prep, a middle school in North Nashville.

He described serious educational and community challenges in the neighborhood, including very low college-readiness outcomes. Those were the conditions he said he was trying to respond to.

The promise of the school was a college-prep education.

He said the results attracted foundation support and federal investment, and the work grew to six schools in six years.

I stopped him there, because 26 is young to be doing this.

I don't know many people in their 20s who even have “start a school” on their radar, much less know where to begin.

Why that? How did you get from a normal life to deciding you could build a school?

He'd been working at the United Nations, writing speeches for the U.S. ambassador. One of his other responsibilities involved organizing volunteer opportunities for people at the U.S. mission.

He arranged for staff to volunteer in Saturday school programs in Harlem.

While he was there, something clicked. This was the work he wanted to do.

The rest wasn't instantaneous. He approached foundations, found funding and support, and built toward starting the school. But he described the original pull as a calling.

He also acknowledged what came with being young.

He was inexperienced in some ways. He was energetic. And he didn't know what he didn't know, which helped him run straight at the thing.

That answer immediately created another question for me.

Hang on. How did you become a U.N. speechwriter in the first place?

He'd joined Barack Obama's first presidential campaign while he was in college and law school. The campaign won. Because he'd been involved early, he was among the young people in line for a political appointment when the administration began.

He thought working at the U.N. would be interesting. That became his assignment.

He said he appreciated it more in hindsight than he had while he was doing it.

I told him that was a wild thing to not appreciate.

His explanation was pretty good. After two years inside a historic presidential campaign, being around a motorcade could start to feel like regular life.

He compared himself to a child actor. You enter an unusual world young enough that part of you assumes this is just what life is like.

He knew, intellectually, that it was unusual. But knowing that and having the space to absorb it are different things.

There was also a lot of work to do.

From the outside, a résumé can read like one astonishing experience followed by another. From inside it, you may mostly be thinking about what needs to get done next.

That brought us back to the schools, and what running them had cost him.

The kind of tired that followed him home

I asked Ravi what his days actually looked like when he was running the schools.

That was where the 4 a.m. alarm came in.

Students started arriving around 7. Staff needed to huddle before that. He remembered the final morning bell being around 7:30, with the school day continuing until 5.

The extra time was deliberate. He said the average student was arriving more than two grade levels behind in core subjects. The school was trying to help them catch up.

So he got up early to plan, then spent much of the day on his feet.

Giving teachers feedback. Meeting parents. Walking halls. Talking with students. Investigating disagreements.

And sometimes riding the bus.

He said he felt buses were where school culture could fall apart. You could work hard on what happened inside the building and then lose a lot of it in the ride to and from school.

So staff rotated that responsibility. He'd go out into the community, ride in with students, spend the day at school, and sometimes ride back out with them.

Then he still had to return for the staff meeting.

“There’s no version of tired like the kind of tired I used to have doing that job,” he said.

But what stayed with him wasn't only the long day.

A student unenrolls. A student gets in trouble. Somebody doesn't go on to college. Somebody gets arrested. You're fighting political battles to keep the schools healthy. You have to let a staff member go, even though you care about them.

Those things don't necessarily stop existing in your head when you leave the building.

He described years of carrying that emotional weight along with the physical exhaustion.

By the end, he needed what he called a full-on reset.

I wanted to understand what leaving looked like, because “I got burned out and left” can skip over a lot.

Did he quit? Sell the organization? What happened?

This was a nonprofit. There wasn't a company sale waiting at the end.

He told his board, roughly a year ahead of his departure in 2016, that they should start planning for his exit. They agreed on a timeline and began a search.

He stayed relatively hands-off in choosing his successor because he wanted the board to own that responsibility. His focus was closing the year well.

That detail matters. He recognized he needed to leave, and he still tried to leave the institution with a workable transition.

He thought he might take more time off afterward. Instead, he jumped into another effort.

He said that next effort wasn't nearly as taxing as running schools. Within it, he started making room for an idea he hadn't been practicing very well: taking care of his own learning and interests.

The oxygen-mask metaphor showed up. He'd spent years focused on students, parents, and teachers. He needed to put some attention back on himself.

That was the beginning of what became The Invisible List.

Give one thing a year of your life

Ravi's invisible list is the collection of things you keep assuming you'll get around to.

Learn Spanish. Play guitar. Fly a plane. Go salsa dancing.

Whatever the things are for you, they can sit in the background for years.

As you get older, he said, the list can start eating at you. You begin to give up on things you used to assume would be part of your life. That can make you bitter or take some of the energy out of you.

His approach was to get those things out of the background and put them into a plan.

Write them down. Choose one. Give it a year.

Think of each year as your own school year, with yourself as the student.

The goal is to go from beginner to at least intermediate in something new. At the end of the year, you can continue or let it go. But when the next year starts, you choose a new thing to learn too.

You don't have to abandon surfing because it's time to learn something else. You also don't have to keep every past pursuit alive forever.

When we talked, he'd been doing this for roughly seven or eight years.

The part he felt strongly about was seeing the chosen year through.

He compared it to a parent who's already signed a kid up for karate. You can decide later whether karate is your thing. Right now, you've committed to the class.

That's how he talks to himself.

Otherwise, it's pretty easy to psych yourself out. You're awkward at the beginning. You're not sure you like it. Something else suddenly looks more appealing.

Then you can end up with a whole collection of activities you briefly started and never got far enough into to really experience.

The year gives the pursuit enough room to become something more than an initial impression.

I asked which item came first.

Powerlifting.

Given that he'd come out of the school years out of shape, that was a pretty practical choice.

His first goal was a number he could work toward

Ravi said that if you're unsure where to begin, he likes starting with something that builds physical capacity.

That was useful in his own case because feeling healthier and stronger would help him do more of the things that might come later.

For his first year, he chose a deadlift target.

He drew on a body-weight-relative metric he'd encountered through a trainer's work with athletes. The details of that training method weren't what we worked through on the show. What interested me was how he chose a goal that gave him something concrete to pursue.

I asked him how he picked the number.

It was relative to his body weight. That gave him two ways to improve the relationship: get stronger and, in his case, lose weight.

He said it also fit with sprinting he was doing around the lifting.

So the pursuit had a measurable target and a reason behind it. He wasn't just telling himself to vaguely get in better shape.

He hit that main goal and went beyond it.

He also competed in a powerlifting competition toward the end of the year.

That brought us to an important distinction in how he organizes these pursuits. He usually has a regular goal and a stretch goal.

The regular goal should be something he expects to reach if he shows up and works at it consistently.

The stretch goal can take longer. Sometimes a lot longer.

He doesn't need every ambitious thing he imagines to happen by December for the year to count.

I liked that distinction enough to keep asking about it. Because once you're putting deadlines and performance goals on your hobbies, there's an obvious concern.

Are we just finding a new way to stress ourselves out?

Getting to intermediate, and the barrel that took years

Surfing gave us a good way to work through that question.

Ravi had never surfed before his surfing year. It happened during the pandemic, when he could stay near the water and get out most mornings.

That's a lot of access. It belongs in the story because it helped determine what he could reasonably try.

His main goal was to reach intermediate.

He described using a skill-rating system where that meant being able to do particular things on a board. It wasn't only a feeling of being better.

Depending on the person and the circumstances, he'd heard that getting there could take months or years. Given his access and the way he was approaching it, he believed he could reach that level within the year unless he got injured.

I asked whether that kind of goal stressed him out.

He said intermediate generally felt achievable to him with a year of deliberate practice.

Mastery was different.

He could pursue it, but he had less control over when he'd reach it. The amount of practice, the demands of the activity, and sometimes talent could make the timeline very different.

He thought he might be able to become an expert surfer if he essentially stopped doing everything else and devoted himself to it for a long time.

That is a different commitment from learning to surf well enough to enjoy it and do meaningful things on a board.

I asked whether he believed intermediate was achievable for most people within a year.

He said that, while there were surely exceptions, he hadn't yet found a pursuit where a reasonable amount of deliberate practice couldn't get someone to an intermediate level in that time.

That's his working belief. The actual demands of your pursuit still matter. Intermediate in a language, an instrument, and a sport won't look like the same assignment.

Then I brought him back to the part of my question I'd interrupted: What was the big thing for surfing?

Surfing a barrel.

That's the move where the wave forms over and around you. Ravi described it as an expert move, though doing it once doesn't magically make you an expert surfer.

It also depends on the waves. Conditions have to be right, and the attempts can involve more danger.

He didn't do it during his surfing year.

It took a few more years.

He tried things to speed up the learning, including artificial waves, and said he spent a lot of money chasing that goal.

I wanted to make sure I understood. He'd picked the big thing that year but hadn't achieved it?

Correct. He hit his regular goal. The barrel remained a stretch goal.

Over time, he'd learned to set those stretch goals with the expectation that they often wouldn't happen in the first year.

They gave him something to keep pursuing afterward if he still loved the activity.

That made the structure make more sense to me.

You can finish the year successfully without pretending you're done learning. You can also keep a bigger possibility out there without making it the only definition of success.

The firm commitment is the year. The choice about continuing comes after you've actually given the thing a chance.

Choose the pursuit that fits the year you're in

I asked how he decides which thing gets the year.

First, Ravi gets down everything he can think of wanting to do. Then he sorts through the kinds of pursuits on the list and considers where they might fit into his life.

Some require a lot more time, travel, and money than others.

If your kids are about to leave for college, or you're approaching retirement, that might create space for a larger undertaking. He called an intensive learning period like that a “skillbatical.”

Surfing was his big one.

But that finally got us to the objection I'd been waiting to ask about.

What if you have very little time and real financial pressure?

He pointed to what he calls an anywhere, anytime skill: something you can practice in smaller pieces without a big financial commitment.

Writing was his example.

Thirty minutes before the kids wake up. Thirty minutes after they go to sleep. A regular half hour at a coffee shop.

Those periods can accumulate into meaningful work if you use them consistently. If you can make it an hour, even better.

He also talked about coordinating with your spouse. Maybe one person takes the kids for a period on Saturday so the other can go work on something, then you find a way to make room for the other person's pursuit too.

The activity itself can also change in size.

Ravi had taken up tennis as a more sustainable sport as he got older. He was moving away from basketball because of the injury risk he associated with continuing it.

You could approach tennis as an enormous project. Go to camps, devote a big chunk of the year to it, chase a high rating.

Or you could take lessons nearby, practice with your spouse or kids, watch instructional videos, and keep the commitment smaller.

Same sport. Different use of your year.

That flexibility matters if the big version is the thing preventing you from considering any version.

You might not have the resources for a year built around a beach. That doesn't settle whether you have the resources for 30 minutes of writing or a regular local lesson.

The question becomes specific enough to answer.

What does this pursuit require, and what can I actually give it in this season?

What about the people who really are busy?

Ravi's answer to the time objection was pretty direct.

He thinks most of us have more slack in our schedules than we admit.

We watch Netflix. We stare at our phones. We spend time without deciding what we want that time to become.

He reached for an example of someone working in a coal mine as a person who might have a particularly demanding life.

I told him I have a friend who literally works in a coal mine, and even he has slack.

Ravi pointed out that a more regimented work schedule might sometimes make the boundaries clearer.

We weren't claiming everybody has an identical amount of free time. His broader point was that you need to look at the schedule you actually have, including the parts you don't usually count.

Could you do an activity with your kids? Could you paint or write during an available period? Could you arrange a little distance from parenting responsibilities with your spouse rather than both being on duty every minute?

He wasn't recommending that every creative pursuit happen while you're simultaneously watching children. He thought deliberately making room could be better.

Then he made a point about what your family sees.

When your kids see you learning, they see you continuing to grow alongside them. When your spouse sees it, that can be attractive.

I agreed with him. Self-improvement in your spouse is incredibly attractive.

There is something compelling about being with someone who is still becoming interested in things and working to get better at them.

Ravi brought up his mom.

She was a nurse, worked two jobs, raised three kids on her own, and still went back to school for a history degree because that was something she'd wanted to do.

That was the example behind some of his conviction. He'd watched someone with real demands on her time make room for learning she cared about.

His advice was to say no to things that don't matter enough.

Your kids matter. Your spouse matters. But maybe some of the Netflix doesn't. Maybe some of the TikTok and Instagram reels can go.

I was very much in favor of saying no to those.

I brought up a phrase I'd encountered from an author whose name I couldn't remember in the moment: high-quality leisure.

Replace some low-quality leisure with high-quality leisure.

TikTok was my example of the first. Tennis was my example of the second.

We didn't have time to work through all the philosophical and practical questions I still had. But that gave us somewhere useful to land.

If you're considering this for yourself, you don't have to begin by finding a completely empty year. You can begin by finding the half hour you're already spending on something you don't particularly care about.

Then decide what you'd rather have practiced by the end of it.

Questions to take into your own week

• If you sell a service that requires client homework, does your price support the level of commitment the work needs?
• When you use a writing tool, can you name the specific job you're asking it to do and the skill you still want to develop yourself?
• What changes when your phone stops being the easiest thing to reach for at night?
• If your work has exhausted you, what would a responsible transition or a smaller commitment actually look like?
• Which thing on your invisible list fits the time and money you have this year?
• What would intermediate mean for that pursuit? What can you measure or demonstrate?
• What is a regular goal you can reasonably work toward, and what stretch goal can remain interesting beyond this year?
• Which recurring pocket of low-quality leisure are you willing to trade for practice?

Choose one pursuit and put its first practice session on the calendar. You can figure out what year two looks like after you've actually lived year one.

Watch the conversation and explore Ravi's work

Watch the full Ravi Gupta interview on YouTube

The Invisible List: official book page

Analog: current program information

Ravi's World on Substack

This conversation was recorded on September 1, 2026. Ravi described The Invisible List as forthcoming on September 22 at the time. The links above go to his current pages; program details discussed in the interview describe that recording date.