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what happens if you fail a class in college

Spencer Rascoff knows a lot about active a aggregation during a crisis.

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He’s the CEO of Zillow, which he ran through the apartment crash. That was afterwards he ran Hotwire, which survived the dot com blast alone to apprentice it awash alike tickets to the 9/11 hijackers.

“There’s the adumbration of this awe-inspiring affiliation to the absolute tragedy itself, and afresh from a business standpoint, basically cipher catholic for like six months,” Rascoff said on Business Insider’s podcast, “Success! How I Did It.” “And so it was a absolute difficult time and we had cogent layoffs.”

Through claimed and able tragedies, Rascoff and his companies bounced back. Zillow now has a bazaar cap that exceeds $5 billion. On this episode, Rascoff tells how he did it. Plus, he tells what Uber’s new CEO is like (they formed calm twice), and what it was like touring with bedrock bands as a kid.

You can accept to the podcast below:

Subscribe to “Success! How I Did It” on Apple Podcasts, RadioPublic, or your admired app. Check out antecedent episodes with:

Following is a archetype of the podcast, which has been agilely edited for accuracy and length.

Alyson Shontell: We’re absolutely blessed to accept you today. Thanks so much, Spencer.

Spencer Rascoff: Acknowledge you. I’m aflame to be here.

Shontell: Can you booty me aback to growing up – what it was like for you? I accept you were an amateur and a chess whiz, and your dad had an alarming job.

Rascoff: I grew up actuality in Manhattan through fifth grade. My dad was an administrator in the rock-and-roll industry, which I’ll acquaint you about, and my mom was a real-estate abettor and afresh a schoolteacher. I had a agitating upbringing.

I was absolutely academic, was a nationally ranked chess amateur and played absolutely competitively. I was the fourth-best chess amateur in the country aback I was a little kid and played every weekend absolutely hardcore. Afresh we confused to LA, and my eyes were opened to this accomplished added apple of possibilities area you could go pond and comedy basketball and comedy sports, and so my accomplished worldview changed.

From an aboriginal age, I was aggressive by my dad’s entrepreneurialism. My dad was a accomplice at an accounting firm, one of the Big Eight accounting firms, now is allotment of KPMG. And in 1972, aback he was aloof a adolescent accomplice there, this white-shoe, New York, early-’70s accounting abutting told the administrator of the Rolling Stones, Prince Rupert Loewenstein, to booty a hike. “We’re not activity to be the accountants for a agglomeration of rock-and-roll, drug-addicted crazy people.” And my dad anticipation that clear ambrosial absorbing actually.

And so he took a leave of absence from the accounting abutting and became the bout accountant on the 1972 Rolling Stones tour. And this was a brace years afore I was born. That started his career, which spanned decades in rock-and-roll and ultimately he was a bout producer, a business administrator of the Rolling Stones, U2, David Bowie, Pink Floyd, Paul Simon, and abounding others.

Watching that acquaintance and growing up in and about the rock-and-roll industry and watching him leave a ambrosial bourgeois industry of accounting for the music industry – and the addition that he brought to that industry – was a big allotment of my upbringing.

Shontell: Aback you see addition booty a big blow like that and afresh ultimately become acknowledged at it, I accept to brainstorm it makes you feel like you could accouterment a lot as well.

Rascoff: Yes, for sure.

Shontell: From what I understand, you had a ambrosial abominable ancestors tragedy appear early. Did that appearance your career?

Rascoff: Definitely.

When I was 15 and my brother was 17, he anesthetized abroad in a car blow aloof a brace canicule afore admission from aerial school, and acutely it afflicted me dramatically. It fabricated me abound up absolute fast. But it additionally kicked me into a altered accessory in agreement of my adventure for achievement.

Prior to that, I hadn’t accomplished abundant dust in my life. I grew up ambrosial flush – bluntly – spending summers touring with bedrock bands in Europe and in Asia with my family. And afresh aback you lose your brother at an aboriginal age, all of a abrupt you’re array of jolted into aloof a altered world. Those aftermost brace of years of aerial school, I affectionate of acquainted like I had to absolutely overachieve, and I formed absolutely adamantine and am still alive absolutely adamantine 25 years later.

Shontell: You went off to Harvard, and afresh you did what a lot of Harvard bodies assume to do: You anguish up on Bank Street.

Rascoff: Too many, in my opinion.

So I accelerating from Harvard, chic of ’97, and the internet was aloof a brace years old afresh and, of my admission chic of about 1,600, apparently beneath than 10 bodies confused out West to assignment in tech. They went to companies like AltaVista and Excite and Yahoo and eBay, which were tiny little startups at the time. Honestly, if you ask them why they did it, I anticipate best of them would say it’s because they couldn’t get jobs in consulting or advance cyberbanking at the time. Of advance these bodies went on to absurd careers and massive abundance from accepting been so aboriginal in technology.

But aback then, the Ivy League was aloof this abettor belt to Bank Street. And, in my opinion, unfortunately, not that abundant has afflicted actually, 20 years later. A huge bulk of our bookish basic aloof gravitates there, absolutely not out of affection for those industries but aloof because they don’t apperceive what abroad to do aback they alum from college. And I anticipate that’s unfortunate. I did my two years and couldn’t delay to get out of there.

Shontell: Aback you were acumen that the Bank Street and accounts apple was not for you, you said your wife helped point things out afore you alike accomplished that you’re black accomplishing something.

Rascoff: Yeah, I alarm this a “career mirror.”

I anticipate it’s abundantly important for anybody to accept a career mirror. It can be a spouse, a friend, a parent, but it has to be somebody that’s far abundant abroad from you that they’re not in the air-conditioned circadian – like it can’t absolutely be a aide – but they accept to be abutting abundant to apperceive you bigger than you apperceive yourself.

Every career accommodation I’ve fabricated has been because my wife told me to, because she’s captivated up a mirror to me. She said: “Look, you’re unhappy. You may not apprehend it, but you’re black accomplishing this thing.” And aback I larboard Goldman Sachs to go to clandestine equity, and I larboard clandestine disinterestedness to do a startup, aback I larboard that startup to do addition startup, every one of those career changes was because she saw article afore I did about how I was feeling.

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Shontell: So allocution to me about the move from clandestine disinterestedness into your startup, Hotwire. It concluded up actuality a huge success. Anybody remembers it. So acquaint me about how that got formed.

Rascoff: Aback I got to TPG, which is a huge private-equity firm, in 1999 afterwards I larboard Goldman Sachs, the private-equity firms were array of on their heels. But the acute affair that the clandestine firms did was they looked at their absolute portfolio companies and approved to bulk out how to advantage the internet.

And so in the case of TPG, we had bought Continental Airlines out of bankruptcy, America West Airlines out of bankruptcy, Ryan Air, which is the better airline in Europe, and we had awash abundant of the Continental pale to Northwest, so by the time I got there, in the backward ’90s, we basically controlled four airlines.

And so Hotwire was built-in out of TPG, adage to these airlines and afresh a brace of added airlines: “Hey, let’s actualize an industry bunch startup to attempt with Priceline.” I was basically staffed on that project, and I eventually larboard TPG to alpha the company. We had to alarm it article cool, and so we alleged it “Project Purple Demon” because that clear absolutely hip and this was San Francisco, 1999, you had to complete air-conditioned to allure employees, and Activity Purple Demon would eventually become Hotwire.

And the abstruse actuality is that, at the aforementioned time, those airlines that we went to, to actualize the company, said: “Hey, this sounds great. We’re activity to actualize an airline-industry-controlled and -owned bunch startup in the discount- biking amplitude to attempt with Priceline. Will you, TPG, additionally actualize one in the full-price class to attempt with Travelocity and Expedia?”

And the activity name for that was T-2, which stood for “Travelocity Terminator.” And we said: “No, we don’t absolutely do this. We’re a private-equity abutting already affectionate of out of our abyss accomplishing this one startup.”

And so the airlines assassin Boston Consulting Group to actualize T-2, which would eventually become Orbitz. So these two companies, Orbitz and Hotwire, were started at about the aforementioned time by about the aforementioned airlines but had absolute altered governance. In the case of Orbitz, the airlines controlled Orbitz, and in the case of Hotwire, the airlines all got non-voting stock, and so the administration aggregation had breadth on how to run Hotwire.

For example, Hotwire pivoted absolute bound to the auberge ancillary of the business, which is area best of the money is in the biking industry. But in the case of Orbitz, they ashore with airline tickets because the airlines capital Orbitz to basically be a antithesis to Expedia and Travelocity. Fifteen-plus years later, you apparently still anticipate of airlines aback you anticipate of Orbitz and you apparently anticipate of hotels aback you anticipate of Hotwire. The airlines capital it to be that way. Of course, now they’re all endemic by Expedia Group, which is who we awash Hotwire to and, ironically, who Orbitz eventually awash to as well. So Expedia Group owns Orbitz, Travelocity, Expedia, Hotwire, Hotels.com, Trivago, and basically everything.

Shontell: So you started what eventually became Hotwire, in the backward ’90s. Prime dot-com boom.

Rascoff: Bubble.

Shontell: And afresh in 2001, acutely 9/11 happened, and that rocked the absolute industry, but you were in the biking industry and it absolutely hit your business hard. So allocution about that, because it additionally sounds like, from what I understand, you all apparent that you alone had a role, unintentionally, in that day.

Rascoff: You know, 9/11 absolutely activated the aggregation for a lot of reasons.

So aboriginal off, for me personally, I was in New York on September 10. I batten at the Millennium Hilton at Apple Trade Center, which was, of course, ashamed the abutting day. I was on the Newark-to-SFO flight on the 10th – or maybe I’m off by a day – but aural a day or two on the aforementioned flight, aforementioned flight number, and so I was alone annoyed up by my affiliation to it, and I absolutely absent a ancestors acquaintance on the alike that went bottomward in Pennsylvania, and so that was acutely difficult. And afresh that morning we had tens of bags of barter who were abandoned about the world, who we had awash airline tickets and auberge apartment to. So we had this huge customer-service nightmare. And afresh to accomplish affairs worse, as you alluded to, Hotwire absolutely awash some of the tickets to the hijackers.

Shontell: How did you apprehend that? And what was it like aback you put that together?

Rascoff: Not that it makes abundant difference, but it wasn’t the September 11 flights, it was the flights a brace of canicule beforehand that put the aggregation in abode in Bangor, Maine, and afresh they flew from Bangor to Logan. I anticipate the way we begin out about it was the FBI told us, they came knocking, I think, apparently that day or aural a brace of days. And it casting this absolutely abominable adumbration of accountability over the company. So as we were disturbing with confused customers, advisers who we weren’t abiding of their location, and afresh there’s the adumbration of this awe-inspiring affiliation to the absolute tragedy itself. And afresh from a business standpoint, basically cipher catholic for, like, six months.

And so it was a absolute difficult time, and we had cogent layoffs. We did a bottomward round, which wiped out a lot of the disinterestedness that the advisers had in the company. To our credit, two years afterwards we had angry the aggregation about and pulled through all of that agony and awash the aggregation auspiciously to Expedia for about $700 million.

Shontell: In all cash.

Rascoff: In all cash, which at the time – this is so quaint, right? – in 2003, aback we awash the company, that was the largest-ever all-cash auction of a tech company. You know, now $700 actor is aloof like an Uber alternation E round.

Shontell: So advancing aback from that, it charge accept been adamantine because it rocked your business, and every tech business was rocked hard, and advancing aback to that affectionate of exit. I mean, how did you do that?

Rascoff: The aggregation ashore together.

I mean, the aboriginal affair we did was we cut abysmal at the company, and I’ve done layoffs, unfortunately, alert in my career, already at Hotwire and afresh already at Zillow. I anticipate it’s important to cut abysmal abundant that you never accept to accept a additional annular of cuts, if possible, because the abhorrence of, “Oh, am I activity to be next?” It aloof paralyzes the organization, so we cut apparently added than we had to, intentionally, to leave some cushion, and we recommitted the abettor abject to the mission and to anniversary other.

You fabricated me allocution about my brother, but I assumption it’s not that altered than that, it’s like, “Now we accept to array of accomplish so that those that are no best actuality didn’t cede what they sacrificed in vain.” And so we formed our butts off to accomplish Hotwire successful. We did a lot of absolutely acute appropriate business-oriented things about the axis to hotels, about innovations in the product.

At the time, Priceline was our capital battling and the “name your price” affair Priceline’s innovation, and Hotwire’s addition was that we showed you the price, and so you didn’t apperceive what the auberge was until afterwards you purchased, but we showed you what the bulk was and so it took some of the academic out of it. And that was absolute avant-garde and it fabricated for a absolute ambrosial bulk hypothesis to our suppliers, our airlines and hotels, but additionally to consumers.

And afresh we took a big bet on advertising. One of the allowances of the dot-com accident was TV advertisement was ambrosial bargain because all those startups that were advertisement in the backward ’90s were gone. And so at Hotwire, we invested absolutely aboriginal in TV. Today, of course, you about-face on the TV and two abnormal afterwards you’ll see an ad for Trivago and Expedia and Tripadvisor, they’re everywhere. But in 2001 to 2003, the airwaves were ambrosial abandoned from biking advertisement and that was a big bet that we made, and it paid off.

Shontell: So aback you’re affairs the company, it sounds like a huge, amazing exit. Was it was abundant for you guys as founders or was it not?

Rascoff: It was not. And this is a acceptable assignment for founders: a bottomward annular basically wipes out best of the abettor disinterestedness because advisers about accept accepted and investors about accept preferred, so a $700 billion auction sounds absolutely abundant but it’s mostly the adventure capitalists that fabricated the money, not the employees. You don’t accept to feel apologetic for anyone at Hotwire, they all did accomplished and they’re accomplishing fine. But it wasn’t the blazon of avenue that I anticipate bodies expected.

Shontell: Right, it’s not like aback you read, “Twenty-five year old sells his aggregation for $700 actor in all cash.”

Rascoff: Apprehend the accomplished print, or it usually doesn’t get printed as accomplished print, but usually belief like that accept a little band of complication to them.

Shontell: So you go on and you become a VP at what is now Expedia.

Rascoff: Yeah, so the two years above-mentioned to the sale, from 2001 to ’03, those two difficult years afterwards 9/11. I was absolutely commuting to Seattle because on September 10, 2001, my wife confused from San Francisco, which is area Hotwire was, to Seattle to go to med academy at the University of Washington. Our aboriginal day afar was September 11, and I bethink watching it on TV from San Francisco and on the buzz with her in Seattle. So for those two difficult years, I was additionally commuting to my wife from San Francisco to Seattle. As anon as we awash the aggregation to Expedia, which is based in Seattle, I moved, like, absolutely that week, and I formed at Expedia and I managed the auberge business for Expedia, Hotwire, and Hotels.com. And I was there for about a year.

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Shontell: And you formed with Dara, who is now the Uber CEO, right?

Rascoff: I formed with Dara, who I’d known. Aggregate affectionate of comes abounding circle.

When I was a summer analyst at Allen and Co., aback I was 19 and in college, he was at Allen and Co. as a inferior advance broker and he was my coach at Allen and Co., so I had accepted Dara aback I was a jailbait really. And in the awe-inspiring baby apple that it is, he concluded up actuality my administrator at Expedia aback he was the CEO at Expedia. And so I appear to Dara and he’s a absurd person, executive, manager, mentor, friend. I anticipate the apple of him and he’s the appropriate best for Uber. He’s absolutely what they charge appropriate now.

Shontell: So you’re basically adage I should accept alleged you two months ago and you would accept accepted that this was accident aback none of the apple did.

Rascoff: It was. And I was afraid how afraid anybody was.

I mean, and that’s absolutely a attestation to Dara; it’s because he is not a self-promoter. Best bodies apparently never heard of Dara Khosrowshahi until the Uber announcement, and that’s because he would accept it no added way.

So I address to Dara at Expedia, but I wasn’t that happy. I capital to be in a abate aggregation environment, added entrepreneurial, area I could accomplish added of an alone difference. And so in 2005 I larboard with best of the Expedia administration aggregation that preceded Dara, and we all larboard to alpha Zillow together. So the aboriginal apparently 15 or 20 advisers at Zillow all came from Expedia, and that’s basically the founding aggregation from Expedia.

Shontell: So were you, like, “Hey, I anticipate let’s do this Zillow thing.”

Rascoff: Bristles or six or seven of us were aloof absolutely in that appointment allowance for weeks discussing, debating, thinking, talking, autograph on whiteboards, aggravating to adjudge whether to do article in absolute acreage or article else.

We knew we capital a startup; we knew we capital to do it together.

We ultimately absitively that the customer charge was so abundant in absolute acreage that consumers were so disempowered. There was this admonition aberration amid consumers and professionals in absolute estate, and so we anticipation we could administer some of the aforementioned capacity about admonition empowerment. However, there’s a huge aberration that frequently gets absent in the details. In the case of travel, it’s a absolutely simple transaction and you don’t charge an intermediary. You can buy an airline admission from Expedia or Hotwire and you don’t charge to allocution to anybody. In the case of absolute estate, it’s a complex, infrequent, expensive, affecting transaction, and so I accept it will consistently accept an intermediary, consistently accept a real-estate abettor in the transaction.

So at Zillow, we never, alike from the absolute beginning, we never endeavored to annihilate the real-estate agent. We aloof capital to accommodate the customer with the aforementioned admonition as the real-estate abettor and afresh let them assignment together. It’s abundant added affiliated to a WebMD, area there’s all this admonition about bloom care, and the accommodating and the patient’s ancestors can apprehend it, but afresh they still go to the doctor and the doctor helps them adapt that information. They’re not acid out the doctor; they’re aloof allegorical the patient.

Shontell: So what’s the aboriginal artefact abundance of Zillow like? And how do you alpha accepting aboriginal absorption for it?

Rascoff: I still bethink we were in this high-rise at 2 Union St., in city Seattle, and we’re attractive at Queen Anne, which is this adjacency on a acropolis that looks at city on one ancillary and Puget Complete on the other. And aback you attending at Queen Anne from the high-rise of this appointment room, you can see this mural of hundreds of houses, and we said: “Every added real-estate armpit focuses on what’s for sale. What if we focused on answering this added catechism that bodies accept about absolute estate, which is, ‘What’s my abode worth?'”

And we looked at Queen Anne, and we envisioned “Imagine a bulk on every rooftop.” Wouldn’t that be amazing?

And afresh to added the Seattle allotment of the adventure actuality – this is absolute Seattle, so allow me for a additional as we sit actuality in midtown Manhattan, feels a apple away. Whales in Puget Complete frequently breach. And so as they canyon from Mexico and California up to Alaska during blast season; you can absolutely see them from offices in Seattle, you can absolutely see whales in Puget Sound, which is, like, can you brainstorm a blast in the East River? It’s awe-inspiring to imagine.

But anyway, so we talked a lot about whales and we said, “When you go blast watching and a blast breaches, a blast all-overs up aloft the water, everybody oohs and aahs and takes pictures of it and talks about “Oh, attending at the whale,” and afresh the blast goes aback beneath baptize for like 45 minutes, and it’s the best arid affair in the world. You accept no abstraction area the blast went. And that addled us as a lot like housing.

When a home comes on the market, anybody talks about it, you booty pictures – “Oh, did you see the neighbor’s house?” – but afresh the home goes off the bazaar and there’s no chat about it. But absolutely a lot of absorbing actuality is accident aback that blast is beneath water, and to the home aback it’s not on the market. We approved to accommodate accuracy to the accomplished real-estate marketplace, not aloof the 3% of homes that are for auction at any point in time. So flash a ablaze on what’s accident aback the blast is beneath baptize was affectionate of afflatus for us.

Shontell: And that was the Zestimate.

Rascoff: Yes.

We said: “OK, let’s try to bulk out what every abode in the country is worth. Great. OK. How do we do that? Able-bodied I apperceive – let’s alarm Stan,” and absolutely we alleged Dr. Stan Humphries, who was active analytics and personalization at Expedia, and we alleged him up and we said, “Stan, we assuredly ample out what we appetite to do. We appetite to bulk out what every abode in the country is worth, and we appetite you to be the actuality who helps us do that.” And he said, “Well, I don’t apperceive annihilation about absolute estate.” And we say: “It’s OK, this is not about absolute estate. This is a algebraic problem. It has annihilation to do with absolute estate.”

And we went about the assignment of accumulating all this abstracts from canton sources. So best of this admonition – bed, bath, aboveboard footage, tax assessment, auction history – is accessible in canton courthouses, but we had to go access it, digitize it, and afresh body the abstracts layer, the Zestimate, that sits on top of that.

And aback we launched in – I anticipate it was February 2006 – we got about a actor visitors aural the aboriginal day. Alike all these years later, I still don’t anticipate any added account – Snapchat, Facebook, whatever – I don’t anticipate anyone abroad has had a actor users in day one because it’s so air-conditioned and so avant-garde to say, “Oh, my god, I can grab my kid’s academy agenda and I can Zillow everybody at my kid’s academy and see what everyone’s abode is worth, see what anybody paid for the home.” That was just, like, this, “Oh, my God” affectionate of affair that launched the aggregation in 2006.

Shontell: So you launched Zestimate. Was there columnist about it? Were account autograph themselves?

Rascoff: Massive press.

I was the CMO at the time, and I met with Henry Blodget at Business Insider – it was a baby operation aback afresh – and we met with Walt Mossberg at The Bank Street Journal and we met with Bob Tedeschi at The New York Times and on and on. We abreast them, beneath embargo, and they were Zillowing their abode and they were Zillowing the houses they grew up in on the analysis site.

Then, the day we launched, there was this huge media explosion, and it brought the armpit down. So the acceptable of this huge bulk of cartage was, well, we launched with a bang, but about six hours later, the website comatose and was bottomward for about four or bristles hours afore we could clutter to get it aback up.

Shontell: And did you accept a apparent on it? Was that important?

Rascoff: We filed apparently a brace of dozen patents, including altered things about the Zestimate, but to be candid, we’ve never absolutely over invested in apparent aegis because it’s the blazon of affair in technology that it’s absolute adamantine to blow on. You can accept a apparent for article and afresh a brace of added companies breach that apparent and afresh you get abatement six years later, but by afresh it’s too late. It’s like, “Well, what acceptable is that?” It wouldn’t save the day, we don’t think.

Shontell: It sounds like you accept this amazing antecedent day of barrage that any startup would annihilate to have, by accepting this avant-garde allotment of technology that you’ve built. But afresh a brace of years later, 2008 happens, and you’re aback in addition crash.

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Rascoff: Yeah, history repeats itself. I’m starting to anticipate maybe I’m the problem.

Shontell: Maybe the businesses you alpha should accord us all a sign.

Rascoff: No, it’s true.

Almost two years to the day from launch, in both cases – Hotwire, ’99 to ’01, and Zillow, ’06 to ’08 – these companies hit aloof a huge brick bank and from an exogenous accident absolutely out of our control. Now, at atomic in this case, we alleged it, we saw it coming. You can still go aback and you can attending on the Zillow blog and see posts that I wrote, and Stan, who by this point had become our arch economist, wrote about how it was obvious, in our opinion, that apartment was activity to blast and that it was congenital on the foundation of beach and there was too abundant accessible acclaim that had accustomed bodies to buy homes who absolutely couldn’t allow them. And so our abstracts was admiration it. Abominably for us, we didn’t abbreviate apartment or annihilation like that. We could accept apparently done absolute able-bodied if we had acted on our data, but we didn’t.

Anyway, we saw it advancing but that was little consolation. Apartment still crashed, we still had layoffs, we abhorred a bottomward annular this time, though, and that is not insignificant. And as was the case with Hotwire, aural addition year or two, we got up off the mat and were accomplishing well. It was the aforementioned thing: It was cut abysmal and recommit the actual advisers to the mission. In both cases, the affliction that Hotwire and Zillow faced, there was a argent lining, it turns out, it fabricated both companies abundant stronger as a result, and I don’t anticipate Zillow would accept been as acknowledged today had it not been for the affliction that we faced in ’07, ’08.

Shontell: So from there you took the aggregation accessible in 2011 – your aboriginal time demography a aggregation public.

Rascoff: I had brash as an advance broker demography added companies public, but absolutely the aboriginal time as a accessible CEO, and it was a fun, absorbing acquaintance but not the end by any means. I mean, we beheld it absolute abundant as aloof a steppingstone, not the end, but the beginning. We had about $15 actor of annual revenue, we had about a $500 actor bazaar cap aback we went public.

Shontell: And now you’re accomplishing what? A billion?

Rascoff: Today, we do about $250 actor of annual revenue, but over a billion of revenue, and we accept about $7 or $8 billion bazaar cap. So the aggregation has developed tremendously: 16 acquisitions and 3,500 employees. Aback we went accessible we had about 300 employees. So aggregate is about 10x today as compared with the IPO about six years ago, and that’s been amazing. It’s additionally affected me to absolutely change aggregate about how I advance and how I administer and what my agenda looks like and what my circadian is because the aggregation is aloof a absolutely altered beastly today than it was six years ago.

Shontell: So allocution about that. You accept a podcast of your own alleged “Office Hours,” and there’s an adventure with Bill Gurley – a acclaimed tech broker who has been on your lath – that I was alert to. Bill was saying, “It’s abundant aback startups can bulk out how to abound to be account tens of millions and afresh accomplish hundreds of millions, but it is a Herculean accomplishment to get it from hundreds of millions of acquirement to billions.” And you’ve done all that, and now your job is to get it from a billion to more.

Rascoff: And it alone gets harder.

It’s true: The aboriginal $100 actor of acquirement is the easiest. That apparently sounds like absolutely callous, but the accuracy is that it alone gets harder. Aback you accept $1 billion in revenue, it’s absolute difficult to abound 25% year over year because you accept to ad-lib huge new acquirement curve to move the needle. And that’s a lot easier off a baby base.

The added affair that faces all companies is, as you get to a ample abundant size, there are bodies whose job it is to assure business curve – they’re aloof accomplishing their job – but this is the archetypal case of ‘The Innovator’s Dilemma,” the acclaimed business book, which says that aback companies ultimately fail, whether it’s Polaroid or whoever, it’s not because they were big and dumb; it’s because they were absolutely absolutely smart. They absolutely were attention their core; they were accomplishing what you anticipate you’re declared to charge to do aback you’re active a big company, but they don’t absolutely innovate because they’re not accommodating to blow the core, and so they get disrupted. And that is what I absorb best of my time annoying about now: We were the disrupter. How do we now abstain actuality disrupted?

Shontell: And best of the money, is it still ads? Is it putting bodies in blow with a realtor?

Rascoff: It’s all advertisement of altered sorts. So about 75% of our revenues – I alarm it $750-ish actor – comes from alone real-estate agents. And afresh we accept a big mortgages business, a rentals business, and a display-advertising business, new architecture business, all that calm is about a division of revenue. But it’s all advertising.

Shontell: You affected on this, but you’ve had to change your administration appearance and your accomplished agenda and aggregate now that you’re active a $7 billion company. How accept you ample out how to do that, and what are some things that you’ve learned?

Rascoff: So aboriginal of all, you accept to booty actively this absorption that for every actuality at the company, you charge to anticipate about, “Is that the appropriate actuality for the abutting two years in the role?”

So if you’re a manager, you accept 10 absolute reports; those people, they appearance up for assignment today aloof because they had the job yesterday, but you as their administrator charge to think, “Is that the appropriate actuality for the abutting two years?” And if not, change that actuality or bulk out to change their point of view. But I additionally anticipate about that for myself, and so I think, “OK, how do I set myself up for what the abutting two years attending like, and what changes do I accept to make?”

Everything I say now has a altered weight to it, which took some accepting acclimated to. I mean, aback we were a baby startup, I could array of ask accidental questions and bandy out accidental ideas. Now bodies absolutely do the things I about say.

Shontell: Your words accept weight.

Rascoff: Yes, and so acumen that requires me to afresh change alike my questions because questions are absolutely statements in disguise, and alike my appearance at things is a vote that I anticipate that affair is important. So actuality absolutely cogitating about those things is article that I’ve formed adamantine at. And so it’s ongoing.

Shontell: All right. So to allow these abundant big houses, you charge to accept a acknowledged career. You’ve had a abundantly acknowledged career. So attractive aback on it, what would you say has fabricated you the best successful?

Rascoff: I’ve consistently looked 10 years my chief and approved to acquisition somebody at my aggregation to anticipate about if I appetite that person’s life, their accomplished life.

Usually, adolescent people, beforehand in their career people, attending at a chief actuality and they attending at their compensation, and I’m advising not to do that. So you’re an accessory in the business department, attending at the VP of business and say, “Do I appetite her or his work-life balance, account in the community, bookish dispatch of their job, title, sure, compensation, yes, but array of the accomplished package?” That’s the aisle you’re on.

Like, you could deathwatch up in the blink of an eye and end up in that world. And if you don’t like that trajectory, afresh acquisition some added path. The added admonition I’d accord is article that Sheryl Sandberg has been absolute clear about, affecting about, which is this accomplished “Your career as a boscage gym not a career ladder.” It’s article that I begin in my career.

So what does that absolutely mean? It agency that you’re on a accurate aisle and afresh be accommodating to go off to the side. So in my case, for example, I was active supplier relations, so relations with the auberge industry, and afresh I confused over to a business role area I absolutely had no acquaintance or background, and afresh I confused over to a accounts role area yet afresh I had no absolute experience. And so it was affectionate of like one footfall to the ancillary to booty two accomplish forward, one footfall aback to booty three accomplish forward, and charting this absolute affectionate of circuitous route, which is different to this generation.

I mean, our parents and our grandparents had a abundant simpler career path, aloof array of do the time and you’ll get answer eventually. That’s not the way it works now. So you accept to body your own career aisle and be accommodating to booty some accomplish to the ancillary in adjustment to booty accomplish up.

Shontell: Spencer, acknowledge you so much.

Rascoff: Acknowledge you.

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