Rahul Vohra

Stalk and Talk: reverse-engineer anyone's email with Rapportive

Sam describes a process he used to land an Airbnb interview: generate ~100 first+last+@domain email permutations in a spreadsheet, paste them into Gmail, and let Rapportive reveal which address surfaced the real social profile.

“And so I invented this thing, this process called stalk and talk. And the idea was I was going to use it to help me get a job at a company. I made this spreadsheet where I would put someone's first name, their last name, and then their URL, like @airbnb.com. And like, I would put Brian and then Chesky and then @airbnb.com, and it would give me like 100 possible combinations of what the name or his email could be. And then I would put it in Gmail and I would highlight each one and Reportive would tell me which email is his because it would show the social profiles related to each email. I ended up emailing the founders of Airbnb, an interview there using Reportive.”

Steal thisGenerate every plausible email permutation for a target, paste them into Gmail, and use an enrichment tool to spot which one resolves to a real profile.

Rapportive sold to LinkedIn making only 15 cents of total revenue

Rahul Vohra reflects that selling Rapportive 20 months in was an efficient outcome, but admits the business was brittle: across its entire history it had figured out how to make only 15 cents of revenue.

“You have to remember that I sold the company only 20 months into its existence for a sum that even to this day remains undisclosed. Assuming it was a good amount of money, then it was a very efficient outcome for the amount of time we put in for what was actually a very brittle business. We'd only figured out how to make 15 cents of revenue in the entire history of the company.”

Superhuman: 60 people, $51M raised, 360,000 on the waitlist

Rahul Vohra shares Superhuman's proxy metrics in lieu of user numbers: about 60 employees, $51M+ raised from First Round and Andreessen Horowitz, and over 360,000 people on the product waitlist.

“Other proxies or other things that people are interested in are we're about 60 people today. We've raised $51 million plus from investors like First Round Capital and Andreessen Horowitz. Marc Andreessen sits on our board. It's really exciting to be able to work with the likes of him. And let's see what else. We have a waitlist for our products. That's something that people are often interested in. We now have over 360,000 people on that waitlist.”

Intentionality: proact, don't react, and update the model when data breaks

Rahul Vohra defines being intentional (a Superhuman company value) as deliberate, model-driven thinking: you preempt rather than react, and when data stops matching reality you immediately update your model instead of staying on the back foot.

“When someone is intentional, they are a very deliberate thinker and actor. They tend not to react. But they proact. They preempt. They get ahead of things. They have a model for how the world or how their business might work. And when the data stops matching reality, they immediately update the model as opposed to constantly being on the back front— back foot, rather.”

Founder vs acquired founder: find the needle vs move the needle

Rahul Vohra distills why founders struggle inside big companies: a founder's job is to find a needle in a haystack, but once acquired your job is to move the needle and the haystack is gone, while your project drops from existential to a strategic bet.

“Unless you come in to run product, you've gone from your thing being existential to your thing is now probably an experiment or a strategic bets. As a founder, your job is to find a needle in a haystack. As an acquired founder, your job is to move the needle. The haystack has long since gone.”

Why incumbents leave premium white space: business model and bundling

Rahul Vohra explains why neither Google nor Microsoft built a premium email product: Google's ad model means you are the product so a paid experience doesn't fit, and Microsoft sells through all-you-can-eat bundles where email is just one checkbox in a one-size-fits-all suite.

“For Google, I believe it's the fundamental business model doesn't support creating a premium email experience, and the company is so large now that it doesn't matter. The fundamental Google business model is of course ads and AdWords. It's to know everything they can possibly know about you, secondarily to keep you in the browser, hence Gmail.”

Steal thisFind a premium segment incumbents structurally can't serve because their business model or bundling strategy forbids it.

Professionals do 3 hours of email a day, 3 billion hours daily worldwide

Rahul Vohra cites the McKinsey study that motivated Superhuman: of the 1 billion professionals in the world, the average does 3 hours of email a day, totaling 3 billion hours per day, second only to sleeping.

“That's the Average professional does 3 hours a day of email. And as we just discussed, they're doing it with one-size-fits-all tools, things like Gmail, things like Outlook. So 3 billion hours per day, every single day, go into email. There's in fact only one thing we do more than email, and that's sleeping.”

The aha moment: 'we kind of ruined Gmail', so rebuild email from scratch

Rahul Vohra recounts the Superhuman origin: realizing the browser extensions he and competitors built sit on Gmail like a virus that slows and clutters it, he asked what if email were rebuilt from scratch the way Apple builds a laptop.

“What if we just built it from scratch? What if we built an email experience the same way that Apple built a laptop? For me, that was like the aha moment that no one has done that because it's really scary and nobody knows how and it's very expensive. But I might be one of the few people in the world that could actually pull it off in the sense of pulling together the team and the capital to make it happen.”

Superhuman for X will mint multiple billion-dollar companies

Rahul Vohra predicts the 'Superhuman for X' pattern (premium, fast, well-designed versions of everyday tools) will produce multiple billion-dollar products and companies, noting it was the most common pitch at the last YC Demo Day.

“I do think that Superhuman for X is It's a very real thing. There's going to be multiple billion-dollar products and billion-dollar companies to be made. In the last YC Demo Day, superhuman for X was the most common X for Y. It's pretty interesting to see the trend take off.”

The Switchlog: timestamp every task switch in Slack to see where time went

Rahul Vohra's time-tracking system: every time he starts, ends, or switches a task he types 'ts:' plus the task name into a dedicated Slack channel, so he can later analyze exactly where his time actually went, unlike a calendar that only records intent.

“Every time I start a task, end a task, or switch a task, I simply go over to Slack, go to a channel I have specifically for this purpose, type in "ts:" and then the name of the task that I am switching to.. And this turns out to be remarkably effective, because then I can go back afterwards and analyze exactly where my time went. Your calendar, in theory, does this for you. But your calendar, at best, says what you wanted to do. And for most founders, it doesn't record what actually happened. The Switchlog does.”

Steal thisLog every task switch with a short tag into one Slack channel, then review weekly to see where your time truly went.

Why API companies are great bets: impossible to rip out once ingrained

Rahul Vohra explains his thesis for investing in business-infrastructure API companies like Clearbit and EasyPost: once an API gets ingrained in a company's stack, it becomes next to impossible to remove, creating durable lock-in.

“Some of my personal investments that have done the best have been companies like Clearbit, which is a rather well-known API for data enrichment, everything from an IP address to an email address. To EasyPost, which is an API for really super simple and rapid shipping. API companies are particularly interested because— interesting because once they get ingrained in a company, they're next to impossible to rip out.”

Steal thisBuild or back infrastructure APIs that embed deep in customer workflows so switching costs make them un-rippable.

Plug-and-play autocorrect library for web apps

Rahul Vohra pitches a missing dev tool: a drop-in library that brings native-quality autocorrect (capitalization, punctuation, transposition errors, conjoined words) to web and Windows editors the way macOS and iPhone do it natively. He says he has searched for it and it does not exist.

“One is a plug-and-play library for autocorrect. So Superhuman works in the browser, it also works in the native Mac app. We will one day build a native Windows app. When you type, I would love to be able to autocorrect the errors in your typing in the same way that macOS does natively. By the way, Windows doesn't do this natively, so if you live on a Windows machine, you probably don't really know what I'm talking about.”

Steal thisShip an SDK that gives any web or Windows text editor iPhone-grade autocorrect, sold to app developers who want a better writing experience.

Universal document-preview library to render any file instantly

Rahul Vohra pitches a document-preview API: throw it any file and get a fast, zoomable, interactable web preview. He notes the only current options (G Drive upload, Microsoft's 5MB-capped libraries, or Box's old Crocodoc library) all have major downsides.

“As far as I can tell, there isn't a really great document preview library that you can just throw any file and it will produce a zoomable, interactable, renderable preview.”

Steal thisBuild a document-preview API priced pay-as-you-go by file size, with enterprise integrations and SLAs at the high end.

You don't need a million users: 300,000 subs at $30/mo is a billion-dollar company

Rahul Vohra's VC-pitch math: at $30/month you only need 300,000 subscribers to reach roughly $108M revenue, which in today's market could value the company at $4-5 billion if growing well, so the question is just whether a path to hundreds of thousands of subs exists.

“It turns out that when you sell a product at $30 a month, which by the way, I agree is a hard price point, but I'll come back to that in a second. It turns out that when you sell at $30 a month, all you need is 300,000 subscribers.”

Steal thisBack into your subscriber target from your revenue ambition and price, then ask only whether that path is reachable.

Small-scale private equity for SaaS: buy, scale 10x, flip

Rahul Vohra's runner-up idea to Superhuman: buy bootstrapped SaaS companies past the hard early phase (making $10K-$100K/month) for $500K-$10M, scale them 10x using a centralized resource pool, and sell them on for far more once ARR grows from $1M to $10M.

“So I think there is a very good business model to be had, and I do know some people pulling this off, where you find companies that have done that phase. Maybe they're making $100,000 a year— sorry, a month, or maybe they're making $10,000 a month, and you spend anywhere in the region of $500,000 to $5 million $10 million to buy these companies outright. You own all of them.”

Steal thisAcquire post-product-market-fit SaaS companies outright, scale them with shared dev/sales/support, then sell at a higher multiple.

Browser extensions birthed Honey and Grammarly, both multibillion-dollar companies

Rahul Vohra notes that what looked like hobby browser-extension projects have become real businesses, citing Honey (a multibillion-dollar company) and Grammarly (another multibillion-dollar extension company).

“It was the thing I built for myself. It was a hobby project, and then I realized that a browser extension could be a real company. And today we have outcomes like Honey multibillion-dollar company. Grammarly, another multibillion-dollar extension company. People are building real businesses on these platforms.”

Superhuman: ~20,000 paying subscribers at $30/month for faster email

Sam pegs Superhuman, the premium email client from Rahul Vohra (who earlier sold Rapportive to LinkedIn for ~$15M), at around 20,000 paying subscribers at $30/month.

“He launched this thing called Superhuman. I think they have about 20,000 paying subscribers at like $300, uh, $30 a month. $30 a month. I bought it. It's cool.”