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‘The Operators’: Experts from WeWork and Brex talk marketing – Getting the most bang for your buck

By Arman Tabatabai

Welcome to this transcribed edition of The Operators. TechCrunch is beginning to publish podcasts from industry experts, with transcriptions available for Extra Crunch members so you can read the conversation wherever you are.

The Operators features insiders from companies like AirBnB, Brex, Docsend, Facebook, Google, Lyft, Carta, Slack, Uber, and WeWork sharing their stories and tips on how to break into fields like marketing and product management. They also share best practices for entrepreneurs on how to hire and manage experts from domains outside their own.

This week’s edition features Christiana Rattazzi, Head of Technology Marketing at WeWork, the leading coworking company that has raised over $8 billion and has a valuation of $47 billion and a rumored IPO impending. Also joining the show is Elinitsa Staykova, VP of Marketing at Brex, another fast-growing unicorn, recently valued at over $2 billion, that is the leading provider of credit cards to startups and tech companies.

In this episode, Christiana and Elinitsa explain how marketing works, how to get into and succeed in the field of marketing, and how founders should think about hiring and managing the marketing function. With their experiences at two of tech’s biggest and most innovative marketers, WeWork and Brex, this episode is packed with broad perspectives and deep insights.

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Image via The Operators

Neil Devani and Tim Hsia created The Operators after seeing and hearing too many heady, philosophical podcasts about the future of tech, and not enough attention on the practical day-to-day work that makes it all happen.

Tim is the CEO & Founder of Media Mobilize, a media company and ad network, and a Venture Partner at Digital Garage. Tim is an early-stage investor in Workflow (acquired by Apple), Lime, FabFitFun, Oh My Green, Morning Brew, Girls Night In, The Hustle, Bright Cellars, and others.

Neil is an early-stage investor based in San Francisco with a focus on companies building stuff people need, solutions to very hard problems. Companies he’s invested in include Andela, Clearbit, Kudi, Recursion Pharmaceuticals, Solugen, and Vicarious Surgical.

If you’re interested in starting or accelerating your marketing career, or how to hire and manage this function, you can’t miss this episode!

The show:

The Operators brings experts with experience at companies like AirBnB, Brex, Docsend, Facebook, Google, Lyft, Carta, Slack, Uber, WeWork, etc. to share insider tips on how to break into fields like marketing and product management. They also share best practices for entrepreneurs on how to hire and manage experts from domains outside their own.

In this episode:

In Episode 4, we’re talking about marketing. Neil interviews Christiana Rattazzi, Head of Technology Marketing at WeWork, and Elinitsa Staykova, VP of Marketing at Brex.

Neil Devani: Hello and welcome to another episode of The Operators, where we learn from the people building the companies of tomorrow. We publish every other Monday and you can find us online at I’m your host, Neil Devani, and we’re coming to you today from Digital Garage here in downtown San Francisco.

Joining me is Eli Staykova, Vice President of Marketing at Brex. Brex is the corporate credit card for start-ups, one of the fastest companies to reach a billion dollar evaluation, having launched barely two years ago, and its customers include Y Combinator, Flexport, SoFi, and many, many other startups.

Also joining us is Christiana Rattazzi, the head of enterprise technology marketing at WeWork. WeWork, with almost 10 billion dollars in financing to date, also counts major corporations and startups among its hundreds of thousands of customers. The firm is reportedly the largest leaseholder in New York, London, and Washington DC and has a footprint in almost a hundred other countries.

Eli and Christiana, thank you for joining us. Just to start, if you can share with our listeners about yourselves, a little bit about where you’re from and how you got into marketing, that’d be great.

Christiana Rattazzi: Happy to lead off. I’m actually from the Bay Area, go Warriors and I was pre-med through college and really thought I was going to go to med school and as I started studying for the MCAT, really discovered that that was what the path was going to be like.

One where you spend a lot of time in the library and maybe you weren’t up for it later and I wasn’t sure I wanted to sign up for that but I wanted to be at a company and being able to speak about a product that I was passionate about. And so that got me into cleantech, as I started my career, actually in cleantech, in marketing because I really loved to write and I love to tell stories.

So that was the beginning of my career and it’s been a great ride since then.

Devani: And what about yourself?

Eli Staykova: I came to the Bay Area in 2006 so I’ve been living here for the past thirteen years, it’s been quite the ride. I came here for the business school at the GSB, Stanford, and I started my career in finance, so I worked for IFC, International Finance Corporation, then for UBS in their LBO group, and I thought that you know after that I would stay in finance.

However, after Stanford I decided to work and live here in San Francisco and it’s so hard to be in the Bay Area not working in tech so I eventually joined the tech world. I work for Apple in their corporate finance team and I recently made the switch back in February at the new company Brex.

Devani: Very cool. These are two very exciting companies, two companies that do a lot of marketing, probably have very sophisticated marketing operations at least that’s what I would assume from the outside.

For the folks who are listening, who maybe don’t know much about marketing, can you help us understand at a very high level, the marking operation in your company. What are the different departments or roles, the different things that are just the nuts and bolts of how it works?

Ethics in the age of autonomous vehicles

By Arman Tabatabai

Earlier this month, TechCrunch held its annual Mobility Sessions event, where leading mobility-focused auto companies, startups, executives and thought leaders joined us to discuss all things autonomous vehicle technology, micromobility and electric vehicles.

Extra Crunch is offering members access to full transcripts of key panels and conversations from the event, such as Megan Rose Dickey‘s chat with Voyage CEO and cofounder Oliver Cameron and Uber’s prediction team lead Clark Haynes on the ethical considerations for autonomous vehicles.

Megan, Oliver and Clark talk through how companies should be thinking about ethics when building out the self-driving ecosystem, while also diving into the technical aspects of actually building an ethical transportation product. The panelists also discuss how their respective organizations handle ethics, representation and access internally, and how their approaches have benefitted their offerings.

Clark Haynes: So we as human drivers, we’re naturally what’s called foveate. Our eyes go forward and we have some mirrors that help us get some situational awareness. Self-driving cars don’t have that problem. Self-driving cars are designed with 360-degree sensors. They can see everything around them.

But the interesting problem is not everything around you is important. And so you need to be thinking through what are the things, the people, the actors in the world that you might be interacting with, and then really, really think through possible outcomes there.

I work on the prediction problem of what’s everyone doing? Certainly, you need to know that someone behind you is moving in a certain way in a certain direction. But maybe that thing that you’re not really certain what it is that’s up in front of you, that’s the thing where you need to be rolling out 10, 20 different scenarios of what might happen and make certain that you can kind of hedge your bets against all of those.

For access to the full transcription below and for the opportunity to read through additional event transcripts and recaps, become a member of Extra Crunch. Learn more and try it for free. 

Megan Rose Dickey: Ready to talk some ethics?

Oliver Cameron: Born ready.

Clark Haynes: Absolutely.

Rose Dickey: I’m here with Oliver Cameron of Voyage, a self-driving car company that operates in communities, like retirement communities, for example. And with Clark Haynes of Uber, he’s on the prediction team for autonomous vehicles.

So some of you in the audience may remember, it was last October, MIT came out with something called the moral machine. And it essentially laid out 13 different scenarios involving self-driving cars where essentially someone had to die. It was either the old person or the young person, the black person, or the white person, three people versus one person. I’m sure you guys saw that, too.

So why is that not exactly the right way to be thinking about self-driving cars and ethics?

Haynes: This is the often-overused trolley problem of, “You can only do A or B choose one.” The big thing there is that if you’re actually faced with that as the hardest problem that you’re doing right now, you’ve already failed.

You should have been working harder to make certain you never ended up in a situation where you’re just choosing A or B. You should actually have been, a long time ago, looking at A, B, C, D, E, F, G, and like thinking through all possible outcomes as far as what your self-driving car could do, in low probability outcomes that might be happening.

Rose Dickey: Oliver, I remember actually, it was maybe a few months ago, you tweeted something about the trolley problem and how much you hate it.

Cameron: I think it’s one of those questions that doesn’t have an ideal answer today, because no one’s got self-driving cars deployed to tens of thousands of people experiencing these sorts of issues on the road. If we did an experiment, how many people here have ever faced that conundrum? Where they have to choose between a mother pushing a stroller with a child and a regular, normal person that’s just crossing the road?

Rose Dickey: We could have a quick show of hands. Has anyone been in that situation?

How top VCs view the new future of micromobility

By Arman Tabatabai

Earlier this month, TechCrunch held its annual Mobility Sessions event, where leading mobility-focused auto companies, startups, executives and thought leaders joined us to discuss all things autonomous vehicle technology, micromobility and electric vehicles.

Extra Crunch is offering members access to full transcripts key panels and conversations from the event, including our panel on micromobility where TechCrunch VC reporter Kate Clark was joined by investors Sarah Smith of Bain Capital Ventures, Michael Granoff of Maniv Mobility, and Ted Serbinski of TechStars Detroit.

The panelists walk through their mobility investment theses and how they’ve changed over the last few years. The group also compares the business models of scooters, e-bikes, e-motorcycles, rideshare and more, while discussing Uber and Lyft’s role in tomorrow’s mobility ecosystem.

Sarah Smith: It was very clear last summer, that there was essentially a near-vertical demand curve developing with consumer adoption of scooters. E-bikes had been around, but scooters, for Lime just to give you perspective, had only hit the road in February. So by the time we were really looking at things, they only had really six months of data. But we could look at the traction and the adoption, and really just what this was doing for consumers.

At the time, consumers had learned through Uber and Lyft and others that you can just grab your cell phone and press a button, and that equates to transportation. And then we see through the sharing economy like Airbnb, people don’t necessarily expect to own every single asset that they use throughout the day. So there’s this confluence of a lot of different consumer trends that suggested that this wasn’t just a fad. This wasn’t something that was going to go away.

For access to the full transcription below and for the opportunity to read through additional event transcripts and recaps, become a member of Extra Crunch. Learn more and try it for free. 

Kate Clark: One of the first panels of the day, I think we should take a moment to define mobility. As VCs in this space, how do you define this always-evolving sector?

Michael Granoff: Well, the way I like to put it is that there have been four eras in mobility. The first was walking and we did that for thousands of years. Then we harnessed animal power for thousands of years.

And then there was a date — and I saw Ken Washington from Ford here — September 1st, 1908, which was when the Model T came out. And through the next 100 years, mobility is really defined as the personally owned and operated individual operated internal combustion engine car.

And what’s interesting is to go exactly 100 years later, September 2008, the financial crisis that affects the auto industry tremendously, but also a time where we had the first third-party apps, and you had Waze and you had Uber, and then you had Lime and Bird, and so forth. And really, I think what we’re in now is the age of digital mobility and I think that’s what defines what this day is about.

Ted Serbinski: Yeah, I think just to add to that, I think mobility is the movement of people and goods. But that last part of digital mobility, I really look at the intersection of the physical and digital worlds. And it’s really that intersection, which is enabling all these new ways to move around.

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Image via Getty Images / Jackie Niam

Clark: So Ted you run TechStars Detroit, but it was once known as TechStars Mobility. So why did you decide to drop the mobility?

Serbinski: So I’m at a mobility conference, and we no longer call ourselves mobility. So five years ago, when we launched the mobility program at TechStars, we were working very closely with Ford’s group and at the time, five years ago, 2014, where it started with the connected car, auto and [people saying] “you should use the word mobility.”

And I was like “What does that mean?” And so when we launched TechStars Mobility, we got all this stuff but we were like “this isn’t what we’re looking for. What does this word mean?” And then Cruise gets acquired for a billion dollars. And everyone’s like “Mobility! This is the next big gold rush! Mobility, mobility, mobility!”

And because I invest early-stage companies anywhere in the world, what started to happen last year is we’d be going after a company and they’d say, “well, we’re not interested in your program. We’re not mobility.” And I’d be scratching my head like, “No, you are mobility. This is where the future is going. You’re this digital way of moving around. And no, we’re artificial intelligence, we’re robotics.”

And as we started talking to more and more entrepreneurs, and hundreds of startups around the world, it became pretty clear that the word mobility is actually becoming too limiting, depending on your vantage where you are in the world.

And so this year, we actually dropped the word mobility and we just call it TechStars Detroit, and it’s really just intersection of those physical and digital worlds. And so now we don’t have a word, but I think we found more mobility companies by dropping the word mobility.

Understanding mental health in Silicon Valley, with professional coach and former investor Jerry Colonna

By Arman Tabatabai

Extra Crunch offers members the opportunity to tune into conference calls led and moderated by the TechCrunch writers you read every day. TechCrunch’s Connie Loizos recently sat down with VC-turned-professional coach Jerry Colonna for a chat about founder mental health, his less than predictable career path and his new book Reboot: Leadership and the Art of Growing Up.

After years as a successful venture investor, Colonna found himself confronting his own personal struggles with mental health. As a result, Colonna shifted his focus towards coaching founders and executives through the tensions that exist between personal happiness, mental health and traditional leadership practices.

In his book and in his conversation with Connie, Jerry discusses how one’s previously developed standards of success can impact their ability to lead and realize fulfillment from their work. Jerry elaborates on why many Valley executives encounter mental health pressures as their careers evolve, and details advice he gives to his own clients to help them re-engage with themselves.

“First, to unpack that ambition itself, is not a negative. It’s just ambition. But when we don’t understand the context of that ambition, what is it that’s driving us forward? Is it fear? Or is it excitement and enthusiasm about what’s possible?

Generally, it’s about both, right? When our ambition is primarily unconsciously driven be our fear, the likelihood is high that we’re going to drive the people who work for us crazy. Because nothing that they do, is ever going to make the fear go away. No matter how successful our ambition makes us.

Because the underlying motivation is fear. I am looking to become safe by what I’m driving towards. Now, if we were to flip it and say the thing that is really driving the ambition, is dreaming of a world that is possible. “I can’t imagine how cool it would be if this company were X.” Well, I may still act in a way that’s driven, but I don’t necessarily have to drive the people around me crazy.

And so by understanding the complicated nature of that word ambition, we get to, as I say, dial up the positive aspect of it and release a little bit from the less healthy more negative aspects of it.”

Jerry and Connie dive deeper into how media coverage impacts founder psyches and how it has evolved amidst an increased awareness around mental health. The two also discuss how external pressures are changing for younger generations of founders, as well as how society as a whole can truly tackle widespread mental health issues.

For access to the full transcription and the call audio, and for the opportunity to participate in future conference calls, become a member of Extra Crunch. Learn more and try it for free. 

Connie Loizos: Jerry, it’s a pleasure to be talking to you. We’ve been talking for many, many years. I’m afraid to say how many years…

Jerry Colonna: It’ll reveal how old we are.

Loizos: I know exactly. But I do remember you starting Flatiron, with Fred Wilson, many, many years ago and then going on to JP Morgan and I know that many of the listeners on the phone right now probably have traced your story because you are one of those characters of great interest in Silicon Valley. Can you talk a little bit about how you decided to leave venture capital and become a full-time coach?

‘This is Your Life in Silicon Valley’: Former Pinterest President, Moment CEO Tim Kendall on Smartphone Addiction

By Sunil Rajaraman

Welcome to this week’s transcribed edition of This is Your Life in Silicon Valley. We’re running an experiment for Extra Crunch members that puts This is Your Life in Silicon Valley in words – so you can read from wherever you are.

This is Your Life in Silicon Valley was originally started by Sunil Rajaraman and Jascha Kaykas-Wolff in 2018. Rajaraman is a serial entrepreneur and writer (Co-Founded, and is currently an EIR at Foundation Capital), Kaykas-Wolff is the current CMO at Mozilla and ran marketing at BitTorrent. Rajaraman and Kaykas-Wolff started the podcast after a series of blog posts that Sunil wrote for The Bold Italic went viral.

The goal of the podcast is to cover issues at the intersection of technology and culture – sharing a different perspective of life in the Bay Area. Their guests include entrepreneurs like Sam Lessin, journalists like Kara Swisher and politicians like Mayor Libby Schaaf and local business owners like David White of Flour + Water.

This week’s edition of This is Your Life in Silicon Valley features Tim Kendall, the former President of Pinterest and current CEO of Moment. Tim ran monetization at Facebook, and has very strong opinions on smartphone addiction and what it is doing to all of us. Tim is an architect of much of the modern social media monetization machinery, so you definitely do not want to miss his perspective on this important subject.

For access to the full transcription, become a member of Extra Crunch. Learn more and try it for free. 

Sunil Rajaraman: Welcome to season three of This is Your Life in Silicon Valley. A Podcast about the Bay Area, technology, and culture. I’m your host, Sunil Rajaraman and I’m joined by my cohost, Jascha Kaykas-Wolff.

Jascha Kaykas-Wolff: Are you recording?

Rajaraman: I’m recording.

Kaykas-Wolff: I’m almost done. My phone’s been buzzing all afternoon and I just have to finish this text message.

Rajaraman: So you’re one of those people who can’t go five seconds without checking their phone.