Why Are We Surprised That Startups Are So Freaking Hard?

Great online writing does two things. First, it makes you think, “Damn, that’s smart,” and second, it makes you snort green tea out your nose. This piece by Benn Stancil made me alternate between these two poles on a sentence-by-sentence basis. Benn approaches a simple yet profound question—“Why are startups hard?”—in a way that feels personal, real, and insightful. I highly recommend this piece even if you don’t currently run a startup—it connected with me on an individual level. —Evan 

In an interview this fall on the Acquired podcast, Jensen Huang—the 60-year-old founder of Nvidia, one of the most valuable companies in the world—dropped a bombshell. Inspired by Huang’s success at Nvidia, the hosts asked him what company he’d start today if he were 30 again. The 60-year-old Huang, without hesitation, said he wouldn’t start a company. The work he put into Nvidia—which, given his net worth of $36 billion, has netted him over $1 billion a year, $3 million a day, or $130,000 an hour—wasn’t worth it:

“The reason why I wouldn't do it—and it goes back to why it's so hard—is building a company and building Nvidia turned out to have been a million times harder than I expected it to be, than any of us expected it to be. And at that time, if we realized the pain and suffering, and just how vulnerable you're going to feel, and the challenges that you're going to endure, the embarrassment and the shame, and the list of all the things that go wrong, I don't think anyone would start a company. Nobody in their right mind would do it.” 

Founder to founder, I have some follow-up questions. Is Huang talking about how hard it is to build a company, or about the actual utility of being extraordinarily rich and relatively famous? If Nvidia wasn’t personally worth it, was the work worth it, for the greater good? And why was it such a surprise that building Nvidia would be hard?

Although it’s hard to relate to a man worth more than Delta Airlines, I can at least sympathize with that last question. Ten years ago, I started Mode, an analytics company that grew to hundreds of employees and tens of millions in revenue, and ended with a $200 million acquisition. Though Mode sold for only 0.02 percent of Nvidia’s current $1 trillion market cap, I was also surprised by how hard the journey was. This experience seems to be the rule rather than the exception. No matter how successful our companies are, nearly every founder I’ve met says the same thing: “This is so much harder than I thought it would be.”

Contrast Huang’s comments with every post-game interview or Hall of Fame speech from a professional athlete, who’s probably sacrificed more than your average startup founder. They always talk about the work; about endless hours in the gym; about adversity and blood and sweat and tears. But after decades of watching athletes reflect on the long climb from their neighborhood gym or Little League field to winning world championships, I’ve never once heard that they were surprised by how hard it was. The injuries were part of the game; the setbacks were what they trained for; the losing seasons were part of the process. 

Moments after winning the World Series last month, Texas Rangers catcher Jonah Heim said: “This is what you work your whole life for..We fought through adversity, injuries, and we came out on top.” Nobody’s surprised by the suffering, because the suffering is what made them great. 

Surprises aren’t supposed to be surprising when you’re told over and over that they’re coming. And yet.

Work, for better or for worse

When you tell people you’re starting a company, they will ask you what it does. If the conversation is with a venture capitalist, it will usually go like this:

Investor: So what does getai.tech do?

You: It’s like [some other popular company that you hope that they wish they’d invested in] but [different in what you believe is some clever way].

Investor: Couldn’t [that popular company that they did invest in, but later than they’d like, in its series E in 2021] build that? 

You: They could but they won’t, because [another clever-sounding point about market dynamics, innovators’ dilemmas, and being “[the latest megatrend]-native”].

Investor: Interesting, that does sound clever. [Emails their now-teetering series E portfolio company to ask if they’ve ever considered adding [trendy but useless feature that nobody would want unless they just wanted to be a part of the latest fad]. The company’s CEO says thank you and forwards the email to their trash can].

You: Yes, we’re excited about it. 

Investor: It is a very exciting time.

If you have this conversation often enough, you’ll stop looking at the popular company that’s been around for a decade for what it is—years and years of very hard work—and start seeing it for what it isn’t—a missing piece; a single blemish; one fatal architectural flaw. 

People will be excited about your company because you have that missing piece. They won’t ask you about everything you have to copy to build a great email client, or a new CRM, or the next enduring social network—they’ll ask you about your clever wedge. Tell someone about your cloud-first Alteryx, or your warehouse-native HubSpot, or your dbt-backed Tableau, or your AI-enabled Zendesk, and they’ll want to talk about the cloud-first, warehouse-native, dbt-backed, and AI-enabled parts. And we’ll deceive ourselves into believing those are the important parts. But all the work is in building the unremarkable features and business processes that Alteryx, HubSpot, Tableau, and Zendesk already have.

Because big businesses aren’t built on gimmicks. You can blitz your way through Sand Hill Road and spike up the App Store charts on gimmicks, but you can’t actually use them to replace Gmail, or Salesforce, or Instagram, or Instagram, or Instagram, or Instagram. Even seemingly instant successes can’t become lasting companies without putting in the work—developing checkbox features, building enterprise sales motions, creating support escalation policies, arguing about sales compensation strategies, defining career ladders, preparing for board meetings, negotiating office leases, hiring lawyers, changing lawyers, dealing with Trinet, helping employees deal with Trinet, responding to investor emails about trendy but useless features that nobody will ever want unless they only want to be a part of the latest fad, setting up the office Wi-Fi, fixing the office Wi-Fi, yelling at Comcast Business about the office Wi-Fi, emailing customers about your new pricing model, redoing your all-hands format, introducing and re-introducing OKRs, and a list of 100 other mundane things that every single one of us overlooks in pitch decks. And after we get to roughly 100 employees, there is a new list.

In other words, building companies and products are, to borrow Jeff Bezos’s famous analogy, like learning how to do a handstand. Most people “think that if they work hard, they should be able to master a handstand in about two weeks.” We get excited about our smart idea; we race it to market; we expect the cavalry to arrive and make this easier. But the reality is that doing a handstand “takes about six months of daily practice. If you think you should be able to do it in two weeks, you’re just going to end up quitting”—or, for the founders who endure, end up surprised by how hard they have to work. 

But nobody can outrun the work; not forever. Eventually—as the company grows, as the market figures out a company’s hacks, as more people copy what it’s done—the work becomes our only competitive advantage. Companies can’t outwit it any more than an athlete can outwit their training. 

Go in the front door

The upside of all of this is that you don’t actually need a clever idea to build a great company. When people ask us how getai.tech plans on beating Mailchimp, it’s tempting to say we’ll start with a freemium product in some vertical they’re missing, build a community of enthusiasts, use data from those users to collect training data for our proprietary LLM, and so on. We’ll win by outflanking and outsmarting the competition. We can’t take them on directly, because they have such a big head start. 

But this is a mistake, for two reasons. First, we can’t actually avoid taking Mailchimp on directly. The clever plan doesn’t remove the need to compete; it just distracts us from it. And second, a lot of companies’ head starts aren’t actually that big. Handstands don’t take two weeks to learn, but they don’t take a lifetime either. Over years of work, companies will spend a lot of time running in the wrong direction. There will be quirks and rough edges that come with constantly building new product additions.

The answer for how we’ll beat Mailchimp is that we’ll line up with them, toe to toe, and build a better product and business. We’ll make Mailchimp, but faster; but better designed; but with more dedicated and relentless customer support. We’ll make Mailchimp without the rust.

I don’t think it’s a coincidence that the companies that have a reputation for building the best products of this generation—Slack, Figma, Superhuman, Notion, and Linear—are basically new versions of successful predecessors. These companies didn’t distract themselves with four-step strategic maneuvers or clever wedges into a new category that they claimed to be creating. They took on the challenge directly instead—built a better Hipchat, or Illustrator, or Gmail, or Google Docs, or Asana. They knew they’d have to do it eventually, and rather than pretend that they could avoid it, they started with that plan. The strategy was to do the work. 

Which all startups have to do eventually. The only question is if we’ll be surprised by it.

Benn Stancil is the Field CTO of analytics software company ThoughtSpot. He joined the company earlier this year as part of its acquisition of Mode, where he was a cofounder and CTO. He regularly writes about data and technology at benn.substack.com, where this piece was originally published. Prior to founding Mode, Benn worked on analytics teams at Microsoft and Yammer.