Taskrabbit’s Stacy Brown-Philpot — Keep humans in the equation

0:00AI agents can make your teams more productive, but if they aren't connected to other agents or your data or existing workflows, they can only take you so far. Any business can add AI agents, but IBM connects your agents across your company to change how you do business. Let's create smarter business, IBM. If you're focused on scaling your business, you know that complexity kills efficiency, which is why Freshworks is here to give you uncomplicated service software. Freshworks builds intuitive tools that make work easier and deliver real ROI today, not someday. Their AI doesn't replace your people, it unlocks their potential.

0:43If you want to increase your team's efficiency and uncomplicate your business, try Fresh Service for IT and Fresh Desk for customer support. Learn more at FreshWorks.com. Does it ever feel like you're paying for 20 platforms to do the job of what really should be just one? That's not software as a service or SaaS. It's SAD, software as a disservice. Replacing your stitched together tech stack with one platform for all your departments? Well, that's Rippling. Rippling eliminates the bottlenecks and busy work of legacy tools and point solutions by uniting your global HR, IT, and spend teams on just one platform.

1:25And right now, you can get six months of Rippling free when you sign up at rippling.com slash scale. That's R-I-P-P-L-I-N-G dot com slash scale. Don't get sad, get rippling. Terms and conditions apply. The rhythm is...

1:49That's D 'Laché Strouder. She's the director of music programs at the Mosaic Youth Theater in Detroit. And the song is... Six times six is 36. Six times five is 30. Even six times four is 24. And six times three is 18. Then get it, do the success, do the success, and so on and so on. And she knows the power of a catchy tune. When teachers need help making a lesson sticky, she goes into the classroom to inject a little music. We might make songs that help teach multiplication facts. We might do a rhythm piece that helps young people talk about syllables. Most people learn the alphabet through the ABC song, so it works.

2:38It's true. The ABC song is a stone-cold classic. Right up there with, I'm just a bill, and three is a magic number. My personal favorite of De Lachey's is Do the Sixes. There's just something about the beat. Six times six is 36 Six times five is 30 Even six times four is 24 And six times three is 18 Get it, do the success Do the success Few of us can resist the power of an earworm That magical series of notes That burrows its way into your brain And bursts out any chance it gets Like any good jingle, Delache's lessons stick. And not only do they stick, they spread. A few voices in a classroom.

3:36Six times six is 36. Six times five is 30 even. Spill out into the playground. From them, more kids pick up the tune. Six times six is 36. Six times five is 30 even. Till the chorus grows, expands beyond the school gates, and spreads into the world.

4:08Like any good cover band, each individual makes the song their own.

4:21It's 36. Do the success. Six times five is 30. Do the success.

4:31D. Lachey knows that possible interpretations are endless. All she has to do is open kids' ears, and they'll keep learning, growing, and singing their songs. And others, in turn, will learn from them. All those students need is the opportunity to sing. Where the tune leads them is anyone's guess.

4:55On the face of it, Delashe's teaching method is awfully simple. Just keep singing. But take a closer look at what Delashe has figured out. She doesn't direct her students to take an interest in math or science. She doesn't force them to memorize, and she doesn't even try to teach them. She knows if she grabs them with a tune and lets them sing, they'll all learn for themselves and then teach each other. Because humans are learning machines. All she has to do is hack their interests with a catchy song. And I'm hoping every tech evangelist out there just perked up at the word hack. Because I believe we can hack our way to a more productive workforce by doing something similar.

5:40Just as those students together create a choir of different voices, so is there a workforce unbound by geography formed by a multitude of people waiting to be tapped. You can call it the human cloud. It's a workforce that can teach itself, learn for itself, and discover its hidden talents. And I believe you can harness the power of this human cloud to solve almost any problem as long as you keep human in the equation. You've got to have incredible talent at every position. It's like this huge push. There are fires burning when you're going home. Can you believe it? Such an idiot. And then you go back to, this is totally going to be amazing.

6:23There are so many easy wins. I have no idea what to do. Sorry, we made a mistake. But you have to time it right. Oops. Working out of a three-bedroom apartment. Stuff that just seems absolutely nut balls. Ten years later, we're like, well, that's just how you do it. We haven't made it just how you do it. This is Masters of Scale.

6:47I'm Reid Hoffman, founder of LinkedIn, investor at Greylock, and your host. And I believe you can harness the power of the human cloud to solve almost any problem as long as you keep human in the equation. But before I go farther, let me define my terms. Most of you are familiar with cloud computing. In fact, you're so familiar with it that you've dropped the formalities. You just call it the good old cloud. Even if you're hazy on what the cloud is, you almost certainly use it every day. Every time you open a Google Doc or use Microsoft Office Online, share a file using Dropbox, or share a photo on Instagram, you're using the cloud.

7:29You're tapping the distributed power of computers across the world to store things and get things done. The human cloud is similar. But instead of tapping the power of distributed computers, you're tapping into a huge network of people. Like computers in the cloud, they're out there, waiting to be assigned a role. TaskRabbit is an example of this. Uber is an example as well. The human cloud has extraordinary potential, but it's more complex than a network of computers, and trickier to harness. Because humans are not robots, they are not a fixed variable. They're different from each other. And miraculously, they change over time.

8:12That's why the true X factor in any equation for scale is the human variable. And in particular, the very human capacity for learning and teaching each other. I wanted to talk to Stacey Brown Philpott about this, because no one I've met has thought more about how you harness the human cloud. Stacey is the CEO of TaskRabbit, the website where anyone can be hired to complete jobs ranging from simple to complex. Stacey is acutely aware of the humans that make up the human cloud and how to help them reach their potential. She's also seen the costs of not doing so. For her, it's personal. I grew up on the west side of Detroit.

8:55It wasn't the best neighborhood. It wasn't the worst neighborhood. But people looked out for each other. Of course, later on, things got worse for a lot of people very, very fast, but it was home for me. The Motor City was struggling as the auto industry's engine faltered and died. Times were tough. Communities were devastated by unemployment and despair. Stacey got an unflinching look at this reality from her very first job, the paper route. Stacey shared hers with her older brother. We would deliver the papers in the mornings, and then on the weekends, we had to go collect from people. And of course, there was always people who didn't want to pay, so I had to make sure we got paid.

9:38And how old were you then? Oh, I was about 10 years old. And so how did you get people to pay? Well, you just knock on their door a lot and often, and then you kind of watch when people's cars would pull up and see them going in the house, and you'd run out and catch them before they closed the door. Where's my money? And then I'm 10, so of course they're going to look at me and say I need to give Stacey her money. But sometimes they just wouldn't answer the door if they didn't have it. So you have to watch people when they go into their house. Most people would agree that stiffing a 10-year-old girl out of her paper route money is a jerk move.

10:13But Stacey wasn't deterred. Some people would see us, and it's like four degrees outside, and they would just give us that extra dollar. And that just meant so much. Because I know it came from people who didn't have a whole lot of money. But they were proud of us for doing real work, good work, you know, legal work in a community where a lot of people did illegal work to make money. And so I think that helped inspire me probably later on that, like, if you do get work for good people, it'll pay off. But there was a less sentimental reason that drove Stacey to lug heavy bags of paper through freezing Detroit streets.

10:53I like to buy candy. I think that's universal amongst 10-year-olds. There's a use for this money. It's called candy. Exactly. Cash equals candy. It's a fun equation you learn as a kid. But Stacey learned some tougher lessons, too. I would say that my upbringing in Detroit taught me grit. It taught me about not just the cold weather, but there's a community that needs to thrive and you need to figure out a way. Stacey found her way from her childhood in Detroit to college at Wharton, investment banking, and business school at Stanford. With her MBA in hand, she applied for a job at Google. Thirteen interviews later, I decided that this was probably one of the best set of people I've ever met in my whole life and that these are the kind of people I want to learn from.

11:44But something was missing. Stacey's high school had been 98 % African American. At Stanford and then Google, she found herself part of a vanishingly small minority. Why were there so few black people in the tech industry? What could be done to tap the huge pool of talent she knew existed? She took those questions to her then boss at Google, Sheryl Sandberg. I said, Sheryl, I think we need to create a network for black people, and I really think we should just recruit more. And you've done a lot of stuff with women, and she'd already really advocated a lot of things around women. And so can you help me with this?

12:20And she said, no, because I'm not Black and you are the person that needs to do it. And she says, Stacey, at one point, you have to realize that you're the person that we've been waiting for to make these things happen. True to form, Sheryl Sandberg got Stacey to lean in. And Stacey's initial effort was decidedly minimalist, a simple email chain. I added all the Black people that I knew and I told them to add all the Black people they knew. This initial move was as low-tech as it gets, but watch how the power of the human cloud kicks in. Recipients forwarded the email to their contacts, who in turn forwarded on to theirs.

12:59The conversation grew. All of a sudden, we were a club that then formalized into not just about recruiting, but we wanted to attract, we wanted to introduce people to the concept of working in tech. We wanted to retain people, we wanted to build community. That club became the Black Googler Network. It pioneered schemes to reach out to talented Black students who otherwise may have missed out on a career in tech. It was one of Stacey's first experiments in tapping pools of talent who sit outside the stream of opportunities. Stacey's time at Google took an unexpected detour to India. Part of her job in India was to make Google's ad platform smarter.

13:43The India team used to approve all the ads that showed up on Google. And there's literally a person that had to go yes, no, yes, no. And finally, we were teaching the machine to do yes, no, yes, no. But at some point, there's some judgment about what's on this page that the machine just can't learn. Most people assume that what's served by Google and other platforms is all technology, all servers. They don't realize the intensity of the human engine behind it. It was this human engine Stacey was building in India. You assume that all automation is possible. And when you're sitting in Silicon Valley, you have that mindset that everything can and should be automated.

14:27And our entire lives will be more efficient because of it. And that was the moment when we learned that there has to be some human judgment somewhere in society. Otherwise, we will make bad decisions. We talk a lot about technology teaching us how to be smarter. But I still believe that there's human beings who just teach technology how to be smarter. And I think that's an important concept that we took later to TaskRabbit. She was starting to explore the essential role that human intelligence plays in artificial intelligence. But her time in India also taught her a more subtle lesson about human nature.

15:04I was stubborn. I had my own way of doing things. I'm a very organized person, and so I would show up at my one-on-ones. When Stacey says one-on-ones, she's talking about the one-on-one meetings with employees who report to her. And I'd have like the 10 things that I wanted to accomplish. And then I'd get through like the first one and feel frustrated that we didn't get through the nine other things. On one level, Stacey was learning what every thoughtful executive learns when they want to work inside another culture. Things don't always work the way you expect them to. So I had that same meeting with the same person the next week and just get more and more frustrated.

15:46But what I needed to learn faster than I learned at that time was that this meeting is not about you, Stacey. This meeting is about the person that you're leading. And that person needs to talk for 25 minutes in the 30-minute meeting in order to be effective in their job. And so seeing more of what I needed to do to help others be successful than what I needed to do to be successful, I had to get hit over the head with that many, many times before it worked. That's a great lesson. The lesson here is more profound than just a cultural exchange. Stacey was learning something essential about humans and how to get the best out of them.

16:24As a manager, your job isn't just to direct your employees or drive their to-do list. Your job is to turn the light on inside them. With her task lists and efficiencies, Stacey had forgotten there was a human in the equation. And so many managers and organizations still do this today. We unknowingly treat our teams like an assembly line, units of work to accomplish tasks. We create systems based on efficiency and rationality. But humans aren't always rational or efficient, at least not the way a machine is. And that's a good thing. Unlike actual machines, which have to be coaxed into learning, people often spontaneously teach each other and themselves if you give them a chance.

17:14A new book zeroes in on just this point. It's called Build an A-Team, and it's written by disruptive innovation expert Whitney Johnson. She's helped countless founders lean into learning. I think we all mean to be a great boss. We mean to be a place that people love to work. The problem is, is that this on-the-job development gets lost in the day-to-day chaos. So then people get bored and stuck, and then they stagnate. And because they're stagnating, so does your organization. Of course, no one intends to let their employees stagnate. What happens is that the better they are, the more you need them to keep doing what they're doing.

17:55You want people to stay, you want them to stay right where they're going to do you the most good. But if you're going to have an organization where learning is taking place and engagement is taking place and you're avoiding getting disrupted, recognize that you and every person on your team is a learning machine. You want the challenge of not knowing how to do something, then learning how to do it and mastering it and then learning something new. Basically, you, me, everyone, we want to learn and leap and then repeat. Learn, leap, repeat. It's a formula for innovative companies and satisfied employees.

18:32As we'll soon see, it's also the formula for the human cloud. But that's getting ahead of our story. This is Mike Nicholas, Capital One business customer and co-founder of Ansett Uncles, a plant-based restaurant and community space in Brooklyn, New York. And he's telling us how they started a product line. We already had a space in the community. The food was an extension of our lifestyle and our values. So we know we wanted to create something that was an offshoot to that. Our pepper sauce. That's my grandmother's recipe. That's like a liquid gold, right? If someone wants to approach us and ask us, what do we do?

19:09We provide flavor. Growing a product line is no small investment, but Mike and his wife and co-founder Nicole were able to manage with the help of their Capital One Business card. Working with Capital One Business, we're able to leverage our limits and utilize those points, making sure we can continue the scale at the speed that we need it to go. To learn more, go to CapitalOne.com slash business cards. Every company wants to grow, but anyone who's scaled knows the truth. Growth creates complexity, and complexity kills growth. Bureaucracy creeps in, culture frays, and suddenly the energy that built your business starts working against it.

19:53I'm Jeff Berman, host of Masters of Scale. And when you want unfiltered insight on fighting that drift, turn to Founders Mentality, the CEO Sessions, with executive advisor, Jimmy Allen. Each episode, leaders from companies like Audible, Walmart China, and AWS reveal how they stayed fast, focused, and human, even at massive scale. Founders' mentality, the CEO sessions, business should be simple. Listen wherever you get your podcasts. We all remember the choices that shape the course of our lives. In business, world-renowned venture capital firm Sequoia Capital calls them crucible moments. Their podcast brings you inside the pivotal decisions that defined some of today's most influential companies like Stripe, Klarna, Zipline, and Supercell.

20:48Tune into Sequoia's new season of Crucible Moments to discover how some of the most transformational companies of the modern era were built. Crucible Moments is available everywhere you get your podcasts and at cruciblemoments.com. Go listen to Crucible Moments today. Stacey just returned from her tour of duty in India, turning over these new ideas about motivating and maximizing human behavior. She came back Back to Google HQ. Back to the confining familiarity of her executive suite. I looked around and I was in an office, two floor-to-ceiling windows. You know, my dog at the time was there. I had his own bed.

21:31I had a table. I had a couch. I had an assistant. I had everything that most people dream of in a corporate job. And I felt like my work wasn't done. And I said, I got to go do something else that grabs at my heart in a way that is going to allow me to accomplish more. But as luck would have it, she met Leah Busk. Leah was the founder of TaskRabbit, and she was searching for a new chief operating officer. Stacey had tried the service out and loved it. In 2013, she joined TaskRabbit. I'm a mission-minded person. And we talk a lot in Silicon Valley about missionaries and mercenaries. And I'm definitely in the missionary bucket.

22:14Google's mission to organize the world's information was, wow, that's huge. And I could do that for the rest of my life. But TaskRabbit's mission around revolutionizing everyday work really grabbed me. And it brought me back home to Detroit. It brought me back to the people who were good, hardworking people who lost their jobs because of the failure of an entire industry, who couldn't find work but had strong work ethics. And here's this great little app that is doing that. When Stacey joined TaskRabbit, it was a website and an app where anyone can hire and be hired to take on simple and not-so-simple tasks.

22:57TaskRabbit was eBay for services when I joined. Anybody can do anything, get anything that they want. And what do they want? Let us count the ways. They're the obvious tasks. Scrubbing grime off the stove so you can get your security deposit back. Helping move that ugly, heavy dresser out of sight into a spare room. But use your imagination for a moment. Because your imagination is the only limiting factor here. How about washing a prize show piglet? helping a jilted lover win their sweetheart back. You had me at hello. Steam cleaning Weird Al Yankovic's stage outfits. No, I'm not making any of those up.

23:41They've all appeared on TaskRabbit, and they've all been completed by taskers, as their freelance all-purpose workers are affectionately known. I couldn't resist asking Stacy about the strangest task she's seen a tasker be tasked with. It was the impersonate my best friend at the birthday party. This got coverage in LA on TV. And yes, no shock. It's like LA, right? No, you didn't mishear that. A tasker was hired to attend a birthday party and convincingly impersonate the guest of honor's best friend. We tracked down that tasker. Her name's Devette C. So I guess my most famous task, the one most people know about, is the time I was hired to impersonate someone at their friend's birthday party.

24:31That was pretty crazy. So Riz hired me to go to Holly's birthday party as Riz. Because Riz couldn't make it. That was Riz's answer, was to send somebody as her, as Riz. I mean, there was no hesitance on my part. Once I read it, I was like, this was custom made for me. We didn't look anything alike. I mean, there's like 20 year gap in age. There's a race difference. You know, I'm black. She's not. So there was another friend and she was going to be the one who called me by Riz's name when I walked in. The friend announced like, oh, Riz, I'm so glad you could make it. And I said, yeah, you know, surprise.

25:17and then there was just this moment of shock and then there was just laughter because it was just the kind of thing Riz would do apparently. Task Rabbit sounded like a blast, right? For clients, it was like having a digital genie in your cell phone who could make all your wishes come true. For taskers like DeVette, it meant every day was an adventure. But the freewheeling system had severe limitations. Taskers had to go through this bidding process for every task. Many found themselves in a race to the bottom to offer the cheapest prices. All right, everyone, I've got this prized piglet here that needs some serious washing.

25:55Now, he's pretty squirmy, very dirty, and he doesn't like strangers very much. Oh, and you're going to have to catch him yourself. I'll do it for$20. I'll do it for$15. I'll do it for$10. I'll even dress him in one of Weird Al's shirts left over from my last job. No extra charge. Pick me. Pick me. Pick me. This bidding system, which could be such a source of excitement for some, was exhausting to others. It took too much time to go through all those bids and choose a winner. And the open-ended Anything Goes framework set many clients up for disappointment. 50 % of the people had a bad experience.