Ryan Smith

Flyering Korean high-rises turned a homeless 17-year-old into an $8K/month tutor

Stranded in Seoul with no job, Ryan Smith printed 5,000 flyers in Korean, befriended apartment security guards to get into mailboxes, and booked back-to-back 55-minute private English lessons. Within a month he was earning $8,000/month at 17 and realized for the first time he could have an idea and execute on it.

“And I got someone to write— I had a pager at the time. I got someone to write a message in Korean, and I made like 5,000 flyers. And I would go in and they'd have these huge mailbox rows, but there was a security guard there. So I would go in and talk to the security guard”

Steal thisWhen you have no money and no network, manufacture distribution: print cheap flyers, befriend the gatekeeper, and run a tight back-to-back schedule.

17-year-old made $8,000/month teaching English in Seoul

After flyering Korean high-rises and booking private lessons, Ryan Smith was earning $8,000 a month as a 17-year-old English tutor, his first taste of having an idea and executing on it.

“literally like a month later, I was making like $8,000 a month as a 17-year-old teaching English. And I was like, how in the world did I go from there to here?”

Use a tough person as a forcing function for focus

Ryan Smith's brother at Google refused to engage unless calls were on-script and focused, which forced Ryan and the team to narrow Qualtrics to the top 100 universities. A demanding gatekeeper makes you edit your own behavior even when they aren't in the room.

“If you're going to call me, stay on script, stay focused, and like actually finish something. And it was a little bit more like, get out of here, right? But he was religious about it. And it was actually an incredible forcing function for me and the team to be like, okay, We're going to go get the top 100 universities and nothing else matters, right?”

Steal thisReport progress to someone who won't tolerate scattered updates; their standard becomes your editing filter.

Trade weakness lists with your co-founder to cover blind spots

Ryan Smith's brother Jared opened the partnership by naming his own five weaknesses and asking Ryan for his, forcing Ryan to confront gaps he'd never examined. The pair deliberately filled each other's blind spots, one full engineer, one full business.

“No, he's like, hey, I suck at these 5 things. What do you suck at? I was like, I don't suck at anything, bro. And he was like, suck this up. Oh boy. And I've heard him say this, like, My job is to develop my younger brother. Who does that?”

Steal thisHave each founder write down their five biggest weaknesses and assign the other to backfill them.

'Who's stopping you?' — the only time his dad got mad

Frustrated that a rival had raised $40M with a better, cheaper product, Ryan complained to his cancer-stricken father, who slammed the table and asked 'Who's stopping you?' The lesson: with only two of you, there's no shortcut and no one to blame, so stop asking permission.

“And finally, it's the only time I ever saw him get mad. And he slams the table, turns around, and he's like, who's stopping you? Who's stopping you from going to do everything you want to go do?”

Know your product cold enough to demo it with no screen

Ryan Smith ran Qualtrics sales demos by sending a link and walking prospects through every feature over the phone, from a car, without looking at the screen himself. He tells reps that knowing your product this deeply is the bar for great selling.

“I could do the demo on the phone in a car with a link, walking them through, right, without me looking at the screen. And explain to them every single thing that's going on.”

Steal thisMaster your product so completely you can demo it blind, just by talking a prospect through their own screen.

Run your business from the outside in, not the inside out

Ryan Smith's core Qualtrics pitch was that a company's employees and customers are its biggest assets, and getting a pulse on them more than once a year lets you operate on a cadence of data instead of guessing. The user who adopts it gets a 'massive propensity of being correct' while everyone else guesses.

“we wanted them to run their businesses from the outside in instead of from the inside out. We, we believe that their employees and their customers were their biggest assets. And like, getting a pulse on them more than once a year was probably a good idea. And then we said, hey, actually, if your business operated with a cadence, right, of this data, you're going to win more.”

Steal thisSurvey your customers and employees on a regular cadence so decisions run on data, not annual guesses.

Don't sell too early: the WordPerfect mentor's warning

Every advisor told Ryan Smith to take the $500M and run, except mentor Duff Thompson, who had sold WordPerfect too early before Microsoft took the market. With Qualtrics cash-flow positive and growing 100%, Duff said don't take the money.

“And Duff's like, we sold WordPerfect too early. You know, we had the market, Microsoft was coming, like we sold too early.. And he was like, I, he was the only person that said, don't take the money. He said, in my mind, you guys are cash flow positive. You're cranking, you're growing at 100%.”

A 'burn the boats' headline killed a $500M acquisition

Ryan Smith's first-ever interview produced a Business Insider headline saying 'the kid who turned down $500 million,' which he feared looked like he'd publicly slammed the offer in Dave Goldberg's face. The article burned the boats on the acquisition, locking in the decision to keep building.

“So she writes this headline, the kid who turned down $500 million with my picture is excited about it. And I'm like, oh my gosh, because it looked like I went to the media with this story and slammed the story back into Dave's face.. And I was so embarrassed. But I knew at that moment that Dave wasn't coming back, right? It was a burn the boat moment.”

Set goals by the headline you want a journalist to write next

Ryan Smith reused the same Business Insider reporter and the same photo for each milestone, generating a series of near-identical headlines ('turned down $500M', 'just raised at $1B', 'raised $2.5B', 'sold for...'). After each one he asked 'What's her next article?' to set the next target.

“And I was like, no, no, no, no. What's her next article? Article?”

Steal thisDefine your next milestone as the exact headline you want written about you, then reverse-engineer the work to earn it.

The exit isn't a eureka moment; it's about the journey

When Qualtrics finally sold, Ryan Smith calls it 'one of the most underwhelming days of my life.' Watching the money hit, he realized it's about the journey, not the payday, and decided he'll work until 80 because he'd never check out.

“but it became clear to me that it is about the journey because even after all that, it wasn't a eureka moment. Right. And so knowing that I'm gonna work till I'm 80, I'm never going to stop working. I already know that about myself.”

Bought the Utah Jazz for $1.6B; Millers paid $22M

Ryan Smith bought the Utah Jazz for roughly $1.6 billion, pricing it off the Forbes valuation pulled up on a phone with no auction. The Miller family had bought the team for $22 million and held it about 35 years.

“I think she had sat across the court from Ashley and I. She knew what we were about. She cared about it being in Utah, and that was important. They had had 35 years. I think they bought it for $22 million.”

Don't blink: there are only 30 NBA teams in the world

Ryan Smith's philosophy on buying the Jazz was that scarce, once-in-a-lifetime assets demand decisiveness, since only 30 NBA franchises exist. You can't comp them like a house, so you go figure it out and don't hesitate.

“And, you know, my philosophy was don't blink. These chance— there's 30 of these things in the world, just go, right?”

The 9 most important minutes of the day

Ryan Smith's rule for parenting around a demanding career: the three highest-leverage windows are the three minutes when your kids wake up, the three when they get home from school, and the three when they go to bed. He schedules calls around them and won't book over them.

“When your kids wake up, when they get home from school, and when they go to bed.”

Steal thisProtect three 3-minute windows daily — wake-up, after-school, bedtime — and never schedule a call over them.

Pick a career by its attributes, not by a picture of the outcome

Ryan Smith argues that having a fixed mental picture of what success looks like makes you miss opportunities. Instead, define the attributes you want — uncapped upside, leadership, exposure to many industries, longevity — and test whether an opportunity fits, even an unexpected one like enterprise software or the auto industry.

“And like, I think those attributes is where I would advise kids and younger people or entrepreneurs to say, okay, don't be so caught up on what this looks like. See if it fits and you'll be blown away that it's like, oh, the auto industry actually works really well for me, right?”

Steal thisList the attributes you want from work (uncapped upside, leadership, variety, longevity) and screen opportunities against the list instead of chasing a specific job title.