Jason Chicola

A billion people will work remotely in our lifetime

Jason Chicola, founder of Rev.com, predicts remote work will explode from a few million today to roughly a billion people working remotely by the time he dies, driven by maturing technology and bandwidth.

“There are so many people around the world that would love to work remotely but can't. They don't have opportunity in their small town or country. I just think that there's going to be a huge change in our lifetimes where by the time I'm dead, I think there'll be a billion people who work remotely.”

Rev hit a $206M valuation with 50,000 workers and 150 employees

Rev.com disclosed on the Forbes AI list that its last valuation was $206 million. The company has 50,000 people working on the platform each month, has raised $31 million, and employs 150 people, more than half engineers.

“We have 50,000 people who work on the platform, uh, each month. Uh, we've raised $31 million. We were on the Forbes AI list a few months ago and it said in there— there we disclosed for the first time that our last valuation was $206 million. We have 150 employees, more than half are engineers.”

Zuckerberg said he'd have built Facebook in Boston, not the Bay Area

Chicola opened a second office in Austin after a board member noted SF isn't the only place to hire engineers. He cites Zuckerberg saying he'd have done Facebook in Boston, and a Chaos Monkeys anecdote that only one of Facebook's first 30 employees besides Zuckerberg remained — evidence that Bay Area housing costs push talent to job-hop.

“I know I saw some interview once where Mark Zuckerberg said if you could go back in time, he would have done Facebook in Boston. I don't know if he meant it, but he said it, which is a big thing to say, um, for a guy like that. And I was reading one book, I think it was Chaos Monkeys, I talked about Facebook, and the guy said that when he got to Facebook, he met somebody who was employee number 29 of Facebook, and that he or she was the only person of, of the first 30 other than Zuckerberg that was still there”

Steal thisOpen a second engineering office in a lower-cost city to retain talent past the vesting cliff.

AI shrinks the price but expands the market by unlocking dead inventory

Chicola argues a cheaper AI transcription tier didn't cannibalize sales — it grew volume because customers ran their whole back catalog of content that was never worth paying a human for. AI delivers higher value at lower cost, expanding the addressable market rather than shrinking it.

“But what we also see even more so is that as we've rolled out, um, a cheaper AI service, our volumes have grown dramatically. Because what's happening is people are coming to us and saying, I have a whole back catalog of content that wasn't worthwhile for me. It wasn't, wasn't important enough to pay a human to do it, but at your lower AI price, I'll do all of it.”

Steal thisLaunch a cheap AI tier to unlock the back-catalog of work that was never worth full price.

Cheaper Uber rides tripled the SF taxi market, not shrank it

Chicola uses Uber as a parallel to AI transcription: even though the price of a ride dropped, the personal-transport market in SF got much bigger because every millennial heading to the bar now takes a $7 Uber Pool, an option that didn't exist before.

“The other example I would say is, look, how big was the taxi market in SF? You know, circa 10 years ago, right? It's a lot bigger now. The market for personal transport is so much bigger, even though the price has gotten lower. How can that be? Well, now every millennial who's thinking of going to the bar is probably going to use an Uber Pool and pay like $7, whereas before, there was no option.”

Watch workers with a stopwatch and kill every micro-friction

Rev doubled transcriber productivity before AI by building software stuffed with productivity hacks — like typing 'bc ' to auto-expand to 'because' — and by literally watching people work with a stopwatch to find and fix wherever they got tripped up.

“And it was full of little productivity hacks in the software. So for example, um, they would have, uh, the person would have shortcuts for things like, um, for a very common word they might see a lot, they might have a little shorthand for it. So instead of writing the word because, B-E-C-A-U-S-E, they would type B-C space and it would form because. And there's like 10 other different types of little hacks that's in the software that each one is not that big of a deal.. But when you put them all together, it makes somebody faster. And so what— and we had teams of people that would, um, we would watch people work almost like with a stopwatch and figure out when they're getting tripped up and say, let's go fix that part.”

Steal thisTime your power users with a stopwatch and eliminate each point of friction one by one.

Don't divide a pie that may never get baked

Joining oDesk (now Upwork) before it could pay him, Chicola worried about negotiating equity. A VC mentor told him to just work and demonstrate value first, because the information was asymmetric. When they finally had the equity talk three months later, both walked in with the same number in their heads.

“A lot of people want to spend a lot of time— to use a different phrase, you know, dividing a pie that may never get baked. And sometimes you want to start baking the pie and figure out a little later how to divide it up.”

Steal thisDemonstrate value first, then negotiate equity once the founder can't imagine doing it without you.

Join a high-growth startup before founding your own

Chicola advises aspiring founders without a burning problem to first do a couple-year stint at a venture-backed, fast-growing startup — ideally in product, which cuts across departments — to learn skills fast and develop judgment for evaluating opportunities, rather than bouncing between tiny startups that go nowhere.

“And most people who haven't been in the game for a while probably don't have the background to be able to evaluate a new idea with high confidence that they're going to get it right. It's all— it's all a really hard thing to do. And that's why, um, if you go— if you look at a startup that has raised venture capital from some decent venture capital firms, is growing quickly, is innovating a lot, um, and you can join in a capacity where you're building and growing something, ultimately hiring people. Um, you're going to learn a lot of skills”

Steal thisDo a two-year stint at a venture-backed high-growth startup before founding your own.

Beat a horizontal marketplace by guaranteeing quality on one job

Chicola built Rev by dissecting Upwork's weaknesses: because Upwork does everything, it can't guarantee quality. Rev does only one thing — convert audio to text — so it can guarantee the outcome. You hire a person and roll the dice on Upwork; on Rev you pay for a service they stand behind.

“And I was able to more or less dissect what did I think were the Achilles heels in Upwork's business model and build a different business model that we don't compete with Upwork in any meaningful way. But there's two things that are different about, about Rev than Upwork. For the customer, we guarantee quality because we only do one thing. We convert audio to text. And because Upwork does everything under the sun, they can't possibly guarantee quality, right, on infinite range of services.”

Steal thisNiche down to one objective service so you can guarantee quality where horizontal marketplaces can't.

Kill the job-application grind: vetted workers just get a queue

On Upwork or Fiverr the median freelancer applies to many jobs, gets rejected, and never gets paid for that selling time. Rev vets a tiered workforce; top-tier workers can take any job anytime, never bid, and never race to the bottom — they wake up to a queue of work.

“Never have a race to the bottom of saying, "That guy will do it for a dollar. I'll do it for 98 cents."”

Steal thisPre-vet a tiered workforce so top performers get a ready queue instead of bidding for every job.

Rev paid $400K for the Rev.com domain

After failing to acquire circle.com (which Jeremy Allaire later used for his Bitcoin wallet company), Chicola spent $400,000 to buy the Rev.com domain — a huge chunk of the company's assets at the time, justified as a drop in the bucket if the company succeeds and a resellable asset if it fails.

“I don't know if I've disclosed, but I'll say it now for fun, we spent $400 grand on the name.”

Rev paid $400K for the Rev.com domain

After failing to acquire circle.com (which Jeremy Allaire later used for his Bitcoin wallet company), Chicola spent $400,000 to buy the Rev.com domain — a huge chunk of the company's assets at the time, justified as a drop in the bucket if the company succeeds and a resellable asset if it fails.

“I don't know if I've disclosed, but I'll say it now for fun, we spent $400 grand on the name.”

Test a brand name on Mechanical Turk for 10 dollars

A Rev co-founder validated candidate names cheaply: he loaded $100 into Mechanical Turk and paid people ~15 cents each to name the first three words and the feeling they associated with each domain, producing a frequency-sized tag cloud per name. 'Rev' returned speed (good), reverend (irrelevant), and revolution.

“He went on Mechanical Turk and he filled his account with like $100. And I think I had at the time like 10 domain names I was thinking about. So for each domain name, he would pay people some small amount, like 15 cents, to answer a question. And the question was like, when you see this word, what are the 3 words that you think of?”

Steal thisCrowd-test brand-name associations on Mechanical Turk for a few dollars before committing.

Remote education is the next big remote-work market

Asked what he'd build if not Rev, Chicola points to online education — an industry the government dominates with little innovation. He notes Rev failed at a math-tutoring service, but cites China's VIPKid, where US stay-at-home moms and retired teachers teach English to Chinese kids over video, as proof of the opportunity.

“There's a company out of China called VIPKid that, um, that has a lot of people in the U.S., um, often, you know, stay-at-home moms or, or retired teachers who will work online on video teaching English to Chinese children. And that's a pretty big market.”

Steal thisMatch underused at-home teachers to students worldwide who lack access to specialized instruction.