Prediction Markets: When Do They Work?

Prediction Markets: When Do They Work?

Don't Worry About the Vase

Epistemic Status: Resident Expert

I’m a little late on this, which was an old promise to Robin Hanson (not that he asked for it). I was motivated to deal with this again by the launch of Augur (REP), the crypto prediction market token. And by the crypto prediction market token, I mean the empty shell of a potential future prediction market token; what they have now is pretty terrible but in crypto world that is occasionally good for a $300 million market cap. This is, for now, one of those occasions.

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Asking for a Friend: How Do You Learn to Manage People?

Asking for a Friend: How Do You Learn to Manage People?

During the nine years Claire Mazur and Erica Cerulo ran the design-minded e-commerce business Of a Kind, they learned a lot—and a lot of it the hard way. To spare you some of the head- and heartaches they experienced, they’re answering a couple Qs about creative entrepreneurship to help you on your way. Here’s the second installment of a two-part series. You can follow their weekly newsletter and podcast for more intel—business, design, and otherwise.


Q. How do I become a good manager? There’s no one showing me the way, and I don’t want to screw it up. Getting good guidance feels especially fraught these days.

Congrats on wanting to get this right! That’s a heck of a start. It seems so many people just jump into a management role without dedicating much headspace to how they want things to function, and unfortunately our thoroughly modern work culture doesn’t do much to set anyone up for success on this front (Management training?! LOL.).

When we hired our first employees, we made a slew of mistakes. You will too—but hopefully what follows will keep you from making some of the same ones we did. You will also get better at it with practice, so cut yourself some slack when you flounder. While you’re at it, try to do the same for the person you’re managing, too. 

Set Some Boundaries

There’s a difference between being friends with someone who reports to you and being friendly with someone who reports to you. If you want this to be smooth sailing, you’re aiming for the latter. Where’s the line exactly? For us, it’s the difference between knowing the name of an employee’s significant other and knowing every detail of their WFH routine. Camaraderie is important—talk about an illustrator you discovered, a book you’ve been meaning to read, a recipe you’ve been cooking all you want!—but developing a too-familiar bond can, among other challenges, make it hard (on both of you) when you need to have a tough conversation. Suddenly, your employee can feel like you turned on them when you’re just doing your job, and the conversation can have a more personal undercurrent than it needs to.

But this doesn’t mean that everything personal ought to stay private. Say there’s a big thing happening in your life that affects your day-to-day, like a sick parent or a pregnancy. Share it in a way that feels authentic to you and appropriate to the setting—and encourage anyone on your team to do the same. Definitely tell people who work for you that you want to hear these things from them—but also lead by example. That’s what sets the tone to make someone comfortable sharing, and you’ll save your reports a lot of stress if they know that you seeming distracted in a meeting has absolutely nothing to do with the project they’re presenting. Navigating these conversations can be harder when they’re mediated by a screen, but that also presents an opportunity to lean into the literal visibility you have into people’s home lives to get (just the right amount of) personal. 

Prioritize—and Systematize—Face-to-Face Communication

How lucky are we to have Slack, email, and all of the collaborative tools we do?! Hugely. But as wonderful as they are, they’re not the best forum for everything you have to say. We hate a waste-of-time meeting as much as the next person, but a weekly check-in with someone who reports to you is never a waste; even if you don’t think you have so much to catch up on, it’s worth doing.

Our take: Create a shared agenda that you both have access to and can update. Ask your employee to drop in all of the projects they’re working on—whether they’re short-term or long-term. For starters, this gives you a full sense of what’s on their plate. Beyond that, it prevents things from slipping through the cracks. You’re much less likely to forget that you need the first round of design materials for the winter symposium in October if “Winter Symposium” has been on the agenda since August. Then, as you both go about your days, you can drop any item into the doc that needs addressing at your next sit-down. We’ve found this wards off poorly timed interruptions from someone wanting your input on something right now—because there’s already time set aside for all that. 

When you get in the same room—or the same Zoom—make your way through that agenda, glossing over anything that doesn’t need to be dealt with immediately (but not deleting those things!!) and, even more importantly, use the face time to get a sense of how your report feels about what’s on their plate, what their priorities are, how the broader team is working together. As in: Actually ask those questions, and phrase them in ways that don’t allow for a “yes” or “no” answer. You’ll get very different responses by posing the Q “Are you stressed?” versus “What project are you most stressed about right now?” This will give you a head start on dealing with potential issues. It will tip you off to minor grievances or scenarios that could go sideways—the smoke before the fire, if you will—and you can figure out how to solve them before they blow up.  

Give Feedback Fast

When the person who works for you knocks your socks off, tell them. That’s confidence-boosting and just plain nice—and it also helps soften the blow when you (inevitably) have to tell them they screwed something up. When that happens—and it will happen!—address it stat. Ask if you can chat for 10 minutes. Say something like, “Hey, I’m disappointed in how this went down. Why did that happen, and how can we prevent it from happening again?” And actually say these things: Don’t type them. Tone is key.

Don’t let the issue fester for a week and then try to deal with it. By giving it days to stew, you make it into something bigger than it needs to be (and likely leave your employee thinking, “Wait, you’ve been upset about that this whole time?”). Plus, being direct eliminates detective work. You don’t want someone spending their working hours searching for signs you’re mad, reading into any curt chat messages, and wondering when another talking-to might be around the bend.

If the “Uh, we need to talk” conversations are happening on a regular basis, well, that’s a separate topic.

Practice Managing Up

One of the very best ways to get good at management is having a boss—good or bad!—and learning to manage them. It might teach you how to best structure an efficient team meeting…or it might show you just how terrible many people are at setting expectations or giving clear direction. 

Sure, it can be frustrating to work for someone who’s not telling you what they want from you, but you can, in fact, ask. “How do you like to receive information?” and “When’s the best time of day for me to run things by you?” and “How do you see me being involved with this client?” are all A+ questions, and getting adept at posing them will remind you what you really should be conveying to someone who works for you. Because it turns out being a good boss and a good employee aren’t so different after all.

from Adobe 99UAdobe 99U

Asking for a Friend: What Does It Take to Build a Successful Partnership?

Asking for a Friend: What Does It Take to Build a Successful Partnership?

During the nine years Claire Mazur and Erica Cerulo ran the design-minded e-commerce business Of a Kind, they learned a lot—and a lot of it the hard way. To spare you some of the head- and heartaches they experienced, they’re answering a couple Qs about creative entrepreneurship to help you on your way. This is the first installment of a two-part series. You can follow their weekly newsletter and podcast for more intel—business, design, and otherwise.


Q. I’m thinking about starting a business with a friend because now, weirdly, is feeling like the right time to go for it. We’ve known each other a long time, but we’ve never worked together. Before we dive into this uncharted territory, what should we know about building a successful partnership?

First things first: We’re so excited for you! About a decade ago (during a recession, it’s worth noting), we were contemplating making this move ourselves, and taking the plunge was one of the best professional and personal decisions we’ve ever made. We feel so strongly about the partnership we’ve built and the life-changing magic of solid business partnerships in general that we wrote a whole book on the topic called Work Wife: The Power of Female Friendship to Drive Successful Businesses. That said, we also very much understand that teaming up with a pal doesn’t always work out the way it has for us. There are plenty of friendship-to-business breakups to look to—Steve Jobs and Steve Wozniak, Paul Simon and Art Garfunkel, and Lena Dunham and Jenni Konner come to mind—and probably at least as many people in your life advising you to never go into business with a friend because you’re putting the relationship on the line.

The fact of the matter is that we can’t imagine starting a company with someone who doesn’t know us in the way we know each other. How different would it be if we couldn’t glimpse across the table in a meeting and say a thousand words with just one look or if we didn’t have the context to help one another navigate the family drama that inevitably weasels its way into the work day? But making the transition from friend to partner takes a ton of trust and plenty of work. Below, our checklist for getting it right.

Kick the Tires on Your Relationship Before You Make Anything Official

You might not have worked together in an official capacity, but have you planned another pal’s birthday together or coordinated a big group trip? If so, were your communication styles similar? Did this potential future business partner do things during that process that made your eyes bulge or your head spin? Because you better believe the same is bound to happen in a high-stress work setting. Be honest with yourself about the clues your friend has given you about the ways they operate in the world—and the ways those things affect you. If your would-be partner dominated the conversation during a Zoom baby shower and you wanted to shout “MUTE!,” trust that the same is likely to happen during business calls. Also remember that if you find yourselves professionally incompatible, it says absolutely nothing about the value of your friendship.

Make Sure You Both Feel a Sense of Ownership

If you do decide to move forward with this pursuit (hey, congrats!), discuss who’s in charge of what early and often. Having clarity on this will keep you from stepping on each other’s toes and also ensures that you both feel like you have authority. As wonderful as collaboration is, you need to be able to divide and conquer—and you need a structured way to make decisions when you have differing opinions.

Our approach: Make an oh-so-simple spreadsheet with your names in two columns and everything that needs to be done to run your business in the rows. Divvy up the responsibilities, and, in doing so, determine that the person with the X by their name is the one who gets final say. This doesn’t mean that the other can’t and shouldn’t weigh in about, say, pricing strategy or social media—just that you’re not going to make every single call by committee and that you trust one another to make good decisions about something, even if it’s not the one you might have made.

Welcome the Power of “We”

A key to establishing a strong partnership is putting egos aside. This is hard! You will fail at it time and time again! One of the best ways we’ve found to remind ourselves—and everyone we’ve worked with, internally and externally—is to lean hard on the word “we,” as in “We’ll get back to you” or “We really appreciate your support.” It’s an itty-bitty, two-letter trick that hammers home that we’re doing this together, and that even if one of us didn’t sign the contract or deliver a piece of hard news, we are both on board. Over the years, we’ve been surprised by the number of people who try to play us off one another or figure out who’s really in charge (talk about infuriating), and this language guards against that, too.

Be Vulnerable

Listen, all of these tips are important, but we might have saved the best for last: You have to be willing to share your feelings, fears, and hang-ups with one another. Expressing that you feel insecure about your role in a project or that your personal finances are in a precarious, anxiety-inducing state is not a to-do list item any of us wants to tackle. But if your partner doesn’t know the things that are keeping you up at night—or the side projects you need to bite off to keep the bills paid—you can’t support each other and make sure this bond is serving both of you. 

One tactic that works for us is to end weekly check-ins (you’re having these, right?) by asking, “How are you feeling about everything?” This is a question that creates an opening for someone to voice any concerns or discontent—related to the partnership or otherwise. It can often feel hard or awkward to know when it’s the right time to bring up something tense. But creating this routine means there’s always an opportunity to do so, and if nothing tough needs to be addressed, great. It’s an opening to hear how the other person is doing, which is just as important.

We understand the instinct to put on a brave face and to want to prove how competent you are, but acting like everything is just peachy when it’s not serves no one. Over time, that will create distance between the two of you and take its toll. And we all (the two of us perhaps more than anyone!) want your partnership to last for the long haul.

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Obsessed: Building a Brand People Love from Day One

Obsessed: Building a Brand People Love from Day One

Welcome to 99U’s monthly Book Club, where we look at book releases that challenge us to think deeper, explore new perspectives, and spark a better understanding of the nuances of a creative career, from leadership and community building to productivity and everything in between.


Red Antler, the Brooklyn-based agency founded in 2007, is behind some of the most memorable campaigns of recent years and is responsible for the branding of some now-household names. Casper, Allbirds, Snowe, Hinge—the company has a knack for developing the stories of start-ups and new ventures, with a fine-tuned radar for what draws us to a brand. 

Co-founder Emily Heyward works with brands from their inception, during those heady first days of launching a product, so she has deep insight into what makes some brands stick. With an eye to the psychology behind consumer decisions, and a keen knowledge of cultural shifts that shape our choices, Heyward’s book Obsessed: Building a Brand People Love from Day One, is a blueprint for anyone thinking about branding and how to create a sustainable connection around a product or service. 

We drew out some key lessons from Heyward’s book, and what her branding strategies can illuminate about integrity, community, and storytelling. 

Start before step one

Red Antler starts working with their clients long before the product launch date. As Heyward says, “Half of our clients are ‘pre-launch,’ which means that we meet founding teams before they’ve launched their businesses, and help them to create the entire consumer-facing experience through the lens of brand.” 

It’s here that the work of brand building begins, and where the big questions need to be addressed and answered. With any venture, whether it’s launching your own studio or embarking on a freelance career, it is crucial to examine your intentions and take a step back to look at the big picture view. Long-term success is impossible without a deep understanding of your purpose and answers to the inevitable questions of who you are and what you stand for. 

“With any venture, whether it’s launching your own studio or embarking on a freelance career, it is crucial to examine your intentions and take a step back to look at the big picture view.”

Heyward says, “Founders need to be thinking about brand from before day one; it needs to be embedded in their culture from the very start.” By weaving it into the DNA of everything you do, your brand will always reflect a fundamental purpose, and help act as a North Star with any tough decisions. Think of branding as woven into your entire being, not a surface-level afterthought. “Leading brands are able to form deep emotional connections because they stand for something that people care about. When I talk about brand, what I’m actually talking about is what a business stands for, at its very core.”

Follow the “Why?” questions 

Obsession arises from the personal connection that consumers when brands speak to them on a deeper level—or when they encourage alignment of their lives and the product. Asking “Why should people care?” prompts a host of philosophical questions, and in Heyward’s experience, many of these eventually circle back to the big one—fear of death. This isn’t necessarily the grim concept that it sounds like! “To successfully launch something new and have people fall in love with it, you need to tap into a need that’s deep and true, and that has existed for a long time before you came on the scene, perhaps as primal as fear of death itself.”

At its core, it is about digging into what is behind all of our decisions, and following the trail of “Why?” questions to come to a common ground. Once you think you’ve reached the deepest level of understanding someone’s needs, go a step further. Does it connect to a universal, primal notion that we all share? That’s where you’ll find the answer to the real problem you’re trying to solve. 

Create community at every stage

Connecting the product to the personal story arc behind it is the strongest bond you need to create. The emotional idea needs to be backed up by practical function. If these don’t line up, your project will always be shrouded in inauthenticity. Start by forging connections between people, which will, in turn, create deep bonds to the brand. Even if you don’t have a brand that naturally lends itself to creating a robust community (Heyward cites Spotify’s playlist ads as a hugely successful illustration of the strong community the brand created), examine where there is potential to nurture community, create a shared vocabulary, and a sense of kinship among those who are users of the product. Heyward notes, “Brands build successful communities when they create a powerful feeling of inclusion. This does not require purposely leaving people out, but it does require a willingness to put a stake in the ground about who you’re for and what you stand for.”

“Brands build successful communities when they create a powerful feeling of inclusion.”

Part of inspiring genuine passion for your product means recognizing that you must make some savvy decisions—about who you’re brand is for and who is not part of your target demographic. Attempting to be all things to all people is a telltale sign of insecurity and lack of understanding of your purpose. Nobody wants to be talked down to, but at the same time, you don’t want to shut an audience out with impenetrable terminology or arcane references. Walking that fine line creates a community of insiders, with a shared passion, and as Heyward notes, “Passion is powerful within an individual, and unstoppable when it’s shared. When a brand creates a movement, it’s because of shared passion.”

The power of the personal 

Today, it might feel as though the world is saturated with new brands, spin-offs, and product launches. It can be easy to feel overwhelmed, cynical, or even wish to opt out altogether. Even for dedicated minimalists, though, consumer decisions come into play every day. So how does a brand appeal to those who are wary of the whole prospect, and what makes the brand-consumer relationship go beyond a merely transactional one? Heyward makes note of the glut of similar ideas that are cropping up in the marketplace, and how branding is ultimately what sets them apart from the rest. “Now, within a month, we’ll sometimes meet with three different teams launching nearly identical ideas. Because it’s so much easier to get things off the ground, and because technology has lowered the barriers to entry for everyone, the difference in success largely boils down to brand.” 

“What makes the brand-consumer relationship go beyond a merely transactional one?”

The success of a brand rests on making it personal and bringing customers into your world. Those who understand how to align their values with their venture are much better placed to succeed. Think about why you have embarked on starting a brand, project, or collaboration. What is driving you to work on it every day and to dedicate your time and energy? Where does your inspiration and motivation come from? Heyward mentions engaging with several clients whose personal stories behind their decision to start a brand set the tone for their story arc and subsequent messaging. This idea of personal alignment can always be traced to the founding team and staff. “Even if you don’t exactly mirror your target audience, you need to embody the values and spirit of the brand you seek to create.”

Start a conversation  

We know that the days of relying on television commercials and newspaper ads are long gone. To succeed in the now, a brand must be nimble and ready to adapt to ever-shifting arenas. Heyward is all too aware of how a brand needs to navigate this changed landscape, “With all the places a brand needs to appear today, you have to bend and flex to keep things interesting.” What’s more, the idea of a static, perfectly polished brand no longer rings true for most of us. We know all too well what goes on behind the scenes, and perhaps even have a healthy skepticism for advertising and targeted marketing. 

Honesty, transparency, and humility are the cornerstones of creating a foundation of trust and making the consumer part of the story. So how do you draw someone in and make them stick around? In Heyward’s experience, the key is to start a conversation. Sparking dialogue between the customer and brand is a way to invite them on the journey, with all the pitfalls and successes. This might mean relinquishing control, which is understandably a daunting risk with any new venture. But that can pay off with remarkable results. “Letting go of control is what allows consumers to become part of the story. Their content gets featured, they see themselves in the brand’s narratives, and they feel more invested. Instead of a top-down approach, it’s a conversation, and conversations are by their very nature unpredictable—at least the good ones are.”

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Stumbling Blocks and Obstacles: How to Overcome Creative Ruts

Stumbling Blocks and Obstacles: How to Overcome Creative Ruts

How do you overcome creative block? It’s a simple question, but one that we wrestle with as creatives over and over again. Just when we think we’ve found the answer to move past a current rut, a new challenge arises. Feeling stuck happens to all of us—newly minted graduates, creatives early in their practice, mid-career practitioners, and seasoned pros. 

Although I help creative professionals get unstuck frequently through my work as a career coach, I decided to turn to the internet for help answering this question: How do you overcome creative block? More specifically, I asked my Instagram followers, who generously shared practical tips, what helps them move forward, how to preemptively tackle getting stuck, and questions for further exploration when creative block strikes.


Preemptively write out your creative tasks. 

Benjamin Welch (@benjaminwelch) shared a new approach he’s been trying, which he’s found helpful so far. “I write out my creative tasks, but do this the night before rather than the day of or right before I start. Then my only decision required is to check the list and start doing something on it. This way I’m not relying on my mood or inspiration to give me ideas and I don’t have to feel pressure to come up with something on the spot.” Instead, he looks at his list, picks something, and starts.

The idea that you shouldn’t wait for inspiration to arrive was echoed by Kara Gordon (@kayessgordon), who said, “I try to remember to not wait for inspiration to strike to make art. Not every mark or work needs to be precious. It’s about the process.”

Shake up your routine.

Multiple people embrace the philosophy that changing things up, literally, can be effective by giving you a break and allowing you to still engage your creativity, but perhaps in another way. Kara Gordon shared that letting go of her routine can also help her move forward, whether that means taking a different route to work, going to a museum, or meeting a friend she hasn’t seen in a while. “Seeing and experiencing something new can allow you to shake up the patterns in your brain.”

Michaela Fiasova (@michaelafiosova) often works on more than one project at a time so she can switch in between them, and when she’s at a standstill, she’ll sometimes watch YouTube videos about something completely unrelated to her project. Indhira Rojas (@redindhi) also takes this approach, switching to a completely different task or activity to clear the mind, even if it’s recreational, “in the hopes that a new insight arises that sparks a new wave of creativity.” For Danielle Evans (@marmaladebleue), the ultimate goal is having some kind of output to build momentum: “I swap disciplines. Sometimes output is output and that’s all that matters.” 

Reconnect with your physical self. 

One of the most suggested tactics for overcoming creative block was to do something physical, whether it’s as simple as a brisk walk outside as suggested by Nicole Jacek (@nicolejacek), or as involved as taking a long swim as Anne Ditmeyer Stark (@pretavoyager) does, “The swimming pool is one of the places where my best ideas come. They flow. It feels counterproductive to getting work done, but the key is unplugging from my computer and screens.” 

Karoleen Decastro (@karoleend) likes to take her physical activity a step further and said that, “Mindful walks work wonders.” She might challenge herself to count ten blue things, nine red things, eight green things, and so on, until she feels grounded and open to her inner world. [Ed. Note: This approach sounds familiar.]

Regardless of how you get out of your head and into your body, making a physical change can help shift your perspective as Lys Hunter (@lyshunter) noted, “Sometimes you have to leave—leave the office, leave your house. Take a walk and try to think about a big world problem. Get out of your small problem.”

Stop resenting the ruts.

Wix VP of Design Hagit Kaufman (@hagitkaufman) has chosen to change her perspective on being in a rut. Instead, she sees it as an opportunity, “I used to hate it. These days I resent it less, because I now know that it always brings me to something or somewhere new.  A new idea, a new way of thinking or something simpler, like putting two old things together in a new way.”  

Payal Vaidya (@payalcv) also sees creative block as an opportunity rather than resenting it. She asks how she can look at it from a different perspective, or even try on different personas who might solve the problem from a new angle, “How might Paula Scher approach this or what would Debbie Millman ask?”

Commit to working through the block. 

While the instinct might be to take a break and do something else, some individuals said they can find it helpful to stay put and work through their block. Kate Aldridge (@k8.aldridge) dives into the part of the project that she enjoys least, or that is the least creative, so it becomes more about production versus pressure to connect with her creativity. “I do the part I enjoy least, like editing, so that I can still have my hands on it to craft it without the pressure of wanting to be creative.” 

For Kriz Bell (@krizbell), it’s about getting the not-so-exciting first draft of a project out of the way. “I start digging in and get the stick-flavored draft out of the way. And if I’m really blank I’ll go basic and dig into who, what, where, when, how. If you keep going, you’ll end up somewhere else.” 

Identify the source of your block.

Sometimes when we experience creative block, it truly is about the project. As Karoleen Decastro noted, it can sometimes stem from fear or boredom about the work. If she can identify the source, she can be more specific about how to address it. Devin Kate Pope’s (@devinkatepope) advice builds on this approach and asks us to consider that what’s stumping us might not be about the work at all. She suggested using the HALT Method. “Am I Hungry, Angry, Lonely, Tired?” If yes, address it and then make another attempt to progress. 

Ultimately, we will have many opportunities to come face to face with creative block over the course of our careers. Expecting it to be par for the course will help us accept that there’s nothing inherently wrong with us—we’re not broken or insufficient. We’re simply having a normal experience. Adjusting our expectations can be key as Indhira Rojas pointed out, especially when our creative block doesn’t dissipate overnight, “If the creative block is a long one, I let go of expectations for the project, give myself a break, relax, and try to gain perspective.” 

Want more on overcoming creative block? Read “How to Overcome Creative Obstacles” by Mia Pinjuh.

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