Ambition, fun and not

Cheat on enterprise sales objection handling.

A brief programming note: It’s the Fourth of July, and I wasn’t planning on bothering y’all today. But the Cluely story that we talked about last Friday stayed a story this week, so here we are, with an American remix of last week’s topic. Because what is the Fourth of July for, if not a time to check your email while distracting yourself from your neighbors’ blaring music and all that, uh, liberty and freedom and winning. I do rather like the real fireworks, though.

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Here is a conversation you might imagine a 30-year-old having with Jensen Huang, the founder of Nvidia and tenth-richest person on earth:

Her: I’m thinking about starting a startup. But I don’t know if I want to do it. What do you think? Should I?

Jensen Huang: No. It is horrifically hard. You shouldn’t do it.

Her: Oh. Uh. Ok. Is that because you have to work on boring things? You get assigned a company to build, and sometimes, you don’t like the one you’re given, like an NBA player who gets drafted by a team they don’t want to be on?

Huang: Actually, you can work on whatever you want. Nobody tells you what to build. That’s completely up to you. You can choose anything, from lunar communications to scalping concert tickets.

Her: Ok, but you must get assigned your coworkers then? People don’t quit a job—they quit a boss. You get to work on whatever you want, but not for whoever you want?

Huang: No, you don’t even have a boss. And you can hire whoever you want. You pick the project; you pick the team. And since you’re in charge, you kinda get to pick your own job too.

Her: There must be some sort of catch. Is it money? If you’re doing whatever you want, you must always be stressed about figuring out how to pay for it.

Huang: You might do that, but most of the time, someone just gives you their money. It’s usually enough to pay for all of your bills for at least a few years.

Her: Like debt? Debt is very stressful.

Huang: Oh, they don’t loan you the money. They just give it to you. Of course they hope you’ll pay them back, but most people don’t.

Her: I guess that’s the catch then—you get to do this once, but if it doesn’t work out, they won’t ever give you money again. So you really don’t want to mess up your one shot?

Huang: If anything, it’s the opposite. If your first company fails, you can just try again, and people will probably be more willing to give you money.

Her: This all sounds pretty good? So maybe that’s it—other people will resent you for having this job? Founders must be seen as social leeches, as great vampire squids wrapped around the face of humanity, the hated bourgeois living off of nepotistic privilege and sucking society dry through some weird venture investment loophole in the tax code.

Huang: Actually, founders are revered. It’s a whole thing.

Her: Let me get this straight. You’re saying I can start a company around whatever idea I want, hire whoever I want, define my own job, pick my hours, get paid someone else’s money to do it, not have any particularly strong obligation to pay them back, and if it doesn’t work out, I can just do it again, all while being celebrated as an American hero?

Huang: Yes.

You: And it’s terrible?

Huang: So much so that I made $140 billion doing it, and I regret it.

If you hang around with people who start startups—including, apparently, the person who started the startup that became the biggest company in the world—they will spend a lot of time telling you how awful it is. They will talk about the stress, the hours, and how nice it would be to “take a break” and “just” work at Google. Some of them might say they love their job, but after a long week and a couple drinks, nearly all of them will say that they’re looking forward to when the job is over. It’s one of the unremarkable certainties in Silicon Valley: The billboards are weird, there is traffic outside Petaluma, and startups are a crushing grind.

But if you detach startups from their reputation, this is kinda bizarre? Because the stylized definition of modern startup—a job to do whatever you want, with whoever you want, paid for by someone else, with $140 billion of upside and effectively no downside—sounds impossibly perfect. Of all jobs, how is that the one that the one that Jensen Huang would never do again?

I mean, it’s not that much of a mystery. Startups might begin this way, as something close to a collective of enthusiasts getting paid to hobby, but they eventually become businesses. And businesses are a lot of work. To run a business, you have to do paperwork, create bank accounts, decide on healthcare plans, rent offices, recruit employees who aren’t your friends, interview them, reject most, hire some, onboard them, figure out complicated variable compensation plans for salespeople, use Salesforce, do accounting, fire people, hire lawyers, fire lawyers, hire these lawyers to fire those lawyers, pay all the lawyers, make Powerpoint presentations, post on LinkedIn, cold call customers, pitch customers, support customers when they call you in the middle of the night, convene board meetings, create a brand, create OKRs, write white papers about digital transformation, change the OKRs, change the brand, set up one-on-ones and pipeline reviews and roadmap syncs and sales kickoffs and quarterly offsites, and fix the office wifi. Building websites with friends is a fairly common hobby; arbitrating disagreements about sales territories is not.

To the extent that there is anything romantic about startups, most of it comes before all of this. It isn’t entirely right to say that startups are innovative and creative in their early days, and calcify when they start trying to “sell to the enterprise,” but it’s not entirely wrong either. Early in their lives, startups kind of are that idealized passion project; once they begin chasing quarterly targets, they become a business, and all the jobs that come with that.

It is also in that transition when a company’s ambition—the real, de facto, on-the-ground ambition, not the phantasmic mission statement that everyone has to pretend to be motivated by—gets defined. Prior to building all of this operational infrastructure, startups really can build what they want, hire who they want, and be what they want. They can pitch big visions or narrow ones; small improvements or revolutions. They are kids, still taking prerequisite classes and trying to decide what to be when they grow up.

After, once there are substantive customers and a corporate apparatus to support them, startups stiffen. And a company’s first declared major is its only major;¹ there is no step two:

When the first step doesn’t go as expected, companies spend their entire lives trying to finish part one. And when the first step does work, companies get captured by their customers, and can rarely escape the shadow of their initial successes. One way or another, prerequisites become permanent.

That’s the rough arc: A phase of youthful freedom, when you really are the boss; and everything after, when the business—including its customers, its board, and the choices you made yesterday—are the boss.

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It seems that nobody wants to be a kid these days. Even YC companies, the archetypes of Silicon Valley startups, are created as opportunistic hustles, founded straight into the business phase. They skip the loose part—the expansive part, the entrepreneurial part, the fun part—because, in a world where every news story is about a new startup going straight up, that part seems like an immature distraction.

Anyway. Say what you will about Cluely, the brash company that we talked about last week—they at least seemed to break this mold. They were all fun;² no business. All bravado and bold ambition, to change the course of human history. No mundane drudgery, no building internal company machinery or integrations with enterprise ERPs.

Ah well. Four hours after last week’s post, they officially launched the first version of their revolution: A meeting recording service that presents live notes and suggested follow up questions as a transparent overlay on your screen. But its primary use cases? Helping people keep up with corporate meetings and handle objections in sales calls.

Regardless of how you feel about Cluely’s whole schtick, its original conceit—to cheat on everything by putting a chatbot in your ear and the answers on your glasses—was genuinely bold. It was sold as the sort of uncategorizable idea that actually has the potential to break real norms.³ And if realized, the product paradigm of instant suggestions as you talk and type is, if not exactly novel, honest innovation.

In many respects, all of this has clearly worked quite well. Cluely has been an explosive meme and Silicon Valley attention sink (case in point). It has been a successful vehicle for fame and wealth creation for its founders, who are likely now worth tens of millions of dollars on paper.⁴ And it is evidently a booming business: According to a report yesterday, Cluely is now making $7 million a year, only a few months after it was founded. Though it’s hard to say how durable that is, and how much it’ll fade when the meme inevitably dies down, money made from selling memes is still money.

But companies can only make the messaging. The market makes the category. And in their rush to build a big company, they launched a small product. Because no matter how bombastic the brand, Cluely’s business isn’t “cheating on everything,” but meeting productivity software:

Which Cluely features are the most interesting to customers? According to [Cluely founder and CEO Roy] Lee, it’s Cluely’s ability to take real-time notes.

“Meeting notes have been a proven very sticky, very interesting AI use case. The only problem with them is they’re all post-call,” Lee said of competitors’ products. “You want to look back at them in the middle of a meeting, and that is what we offer.”

Cluely’s competitors are Granola and Gong. Its roadmap is a Salesforce integration, a Workday integration, an integration into corporate knowledge bases. The fourth link on its website is for “Enterprise,” and sells onboarding, training, and support escalation. This is the stuff of making money, but it is not exactly the stuff of changing the world.

Maybe that’s fine; maybe that’s the point; maybe the business was never even the point at all. But it is a business now, and this is almost certainly the business it will be.

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At the end of Aladdin (spoiler alert, but it’s a thirty year-old movie, so if you don’t know it by now, I don’t know what to tell you), Aladdin tricks Jafar into using his last wish to become a genie. He’s granted phenomenal cosmic power—and everything that goes with it. The potential to command and control the world, stuffed in an itty bitty living space. That’s the irony of Cluely, and often, of startups in general: In their eagerness to do something big, they let the urgency of building a business distract them from the time it takes to do something truly ambitious.

The potential to end human thought, now trapped in a company that sells sales software.

1. This is a bit hyperbolic; companies do obviously launch second products. But the one sentence definition of a company—Superhuman is an email client; Slack is for company chat; Uber is for calling a car; Shopify is for hosting online stores; Google is for search—rarely changes between launch and IPO. So, yes, startups can grow beyond their first product, but they are usually well beyond being a startup when they do.

2. I’m using the term fun loosely here, though they at least seem to be having fun.

3. Whether or not we want to break those norms and whether or not we want our new norms to be defined by Cluely are different questions, and one everyone can answer on their own.

4. The rough math here: Cluely raised $15 million on a reported $120 million valuation in this most recent round. Assuming they sold 10 to 20 percent of the company when they raised their seed round, investors would own about 30 percent of Cluely. The employee option pool is probably another 10 percent, implying the two founders own about 60 to 70 percent, or roughly $40 million each. On paper, of course.