Why do Rich People Keep Working?

This is a question I ask them, point blank on a weekly basis. In my role as an Industry Analyst, I meet with startup entrepreneurs who pitch me on their business so I can understand how they fit into our research publications.

Usually, they present a slide on the leadership team’s background to demonstrate experience and capability. More often than not, the CEO and founding team are serial entrepreneurs, they’ve done it over and over and over again.

First, I congratulate them on their success, then I often ask them, point blank “So why are you still working?”. Cheeky? It’s a valid, question, as I’m trying to understand motivation and commitment towards the vision in which they’re trying to convince me of.

Reason 1: They love to build
You may think it’s because they’ve over spent on a luxury lifestyle and must sustain it, however over and over, they tell me “I love to build things”, or “I want to make a difference”. They enjoy the hunt, thrill, the exhilaration of building something from scratch, growing the value, and then distributing value for those involved. It’s the thrill of the game, the opportunity to build a legacy.

Reason 2: They can’t sit still
More often than not, I see first time entrepreneurs who had an exit “take some time off”, which is a code word for enjoying a few months on the beach. I find that most of them can’t take more than a few quarters or years off, as they get the buildings itch again. Often, a VC taps them on the shoulder and asks them to get back in the game. Or, they simple worry they’re getting stale and wonder if they can do it again, beyond a one hit wonder.

Reason 3: Money isn’t as important
The other unsurprising thing is that those that are wealthy, are focused on higher order things in their live. Money is low on Maslow’s pyramid, I find a few entrepreneurs are now focused on using their power and money to help those around them, or to help them selves in their quest for self-actualization.

So there you have it, there’s a number of reasons why rich people keep working, they include: 1) They love to build 2) They can’t sit still. 3) There are more important things beyond money.

If you liked this post, read about my observation about young and old, rich and modest:

Image credits: Project Life Mastery

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State of The Obvious Corporation: 2013



Recently news came out that Obvious partner Biz Stone is starting a new company called Jelly. What is Jelly? Biz is planning to share more of that soon. I can tell you I’m super excited about the idea and think Biz and the rockstar team he’s putting together are going to kill it.

In related news, Medium — the main internal project of Obvious for the last few months — is now operating as its own company. We have 30 people focused on many big ideas for the site you’re reading now. Personally, I’m spending about 98% of my time on it.

Our third Obvious co-founder, Jason Goldman, relocated to New York City last year to spend most of his time working with Obvious partner company, Branch, which incubated in our office early last year. (Medium has a New York office that now shares space with them.)

What does this mean for The Obvious Corporation?

Turns out, we like focus. We rebooted Obvious in 2011 with a vague plan. We started investing, incubating, and experimenting to figure out what worked and what we wanted to do at this stage in our careers; we just knew we wanted to work together on stuff that mattered.

Among other things, the first few months taught us that we gravitated toward diving in more deeply on a small number of things — rather than having a lighter touch on many ventures.

That said, the collaboration between Biz, Jason, and myself — which we call “Obvious” — continues. This happens in several ways. For one, we have shared interest in each of the big projects we’re currently focused on and call on each other for help. Secondly, we have a portfolio of companies we’re very proud of and continue to help out however we can. So, besides Medium, Branch, and Jelly, we have working relationships with Lift (of which I’m on the board), Beyond Meat and GoodFit (of which Biz is on the board) and Neighborland. We also have a handful of less-active partnerships with entrepreneurs we were lucky enough to angel invest in, like Findery, LaunchPad Toys, and Faraday Bikes. (There are a couple more, which we’ll announce when the time is right.)

In the latter cases, Obvious is simply the vehicle through which we co-invest in entrepreneurs that share our worldview. We plug them into our greater network and increase the chance of being helpful by pooling our resources. As far as hands-on work goes, while Biz and I have our hands full, Jason is actively looking for another company he can (silently) partner with in New York.

More than anything, as Biz likes to say, Obvious is a philosophy. It’s a philosophy that has held us together as partners — and friends — through many years and, now, has launched a new chapter and new set of ventures which will be stronger through association.

As we announced almost two years ago when we started Obvious (the second time), our aim is to build systems that help people work together to make the world better.

That’s the thread that ties it all together.

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The Art of Feedback: 5 Tactics that Work

A few weeks ago, I wrote about the importance of real-time, 360 reviews in the workplace, or something I call “On-the-Spot” performance reviews. But feedback by itself won’t necessarily spur positive change—regardless of when it’s delivered. What matters is how team members receive the feedback and what they do with it. I think we’ve all delivered feedback, or at least known someone who has, when it wasn’t delivered well and was ultimately misunderstood.

Giving feedback that works is an art. And while the “On-the-Spot” performance review is a vehicle to delivering feedback, the tactics that you use determine whether your feedback falls on deaf ears—or is put into action.

Here are my tips for giving unforgettable feedback that works:

#1 Recognize how your team members prefer to receive feedback.

The easiest way to find out is simply to ask: “How do you prefer to receive feedback?” Some people prefer to receive feedback in person so they can have a discussion. Others may prefer to receive it in writing so they can reflect and process before taking the next steps toward improvement. By working with team members to deliver feedback in a format that’s preferable to them, you also improve morale by communicating that you care deeply about your team members and are sensitive to their working styles.

#2 Document any coaching sessions in writing.

I learned this strategy relatively early on in my career when I was having a problem with one of our managers. One evening, I discussed the issue with him face-to-face and thought I had done a pretty good job at delivering a tough but constructive message. To reinforce my points, I crafted a follow-up email, sent it, and intended to follow up again in the morning—but almost immediately, my phone rang. It was the same manager I had just spoken to, and after having seen my points in writing, he realized that the issues were more serious than he thought. We had breakfast early the next morning to help resolve any confusion.

This experience made me realize that we each had a vastly different understanding of the conversation, and my meaning became clear to my employee only after I had conveyed my ideas to him in writing. Now, whenever I have specific or difficult feedback to give, even if it starts in a meeting or over the phone, I make it a best practice to follow up with something in writing.

#3 Set and clarify the context for your feedback.

Team members’ responsibilities and your expectations of them should be perfectly clear. Talk to them. Coach them. Answer their questions. Their role should not be vague—and if it is, you should ask yourself, “What context did I fail to set?” This is another piece of wisdom I picked up from Patty McCord, the former Chief Talent Officer at Netflix. Says Patty, when giving feedback or mentoring, make sure you set the specific context for the feedback as it relates to your expectations of the team member. In other words, when they receive feedback, they should understand exactly why the feedback is constructive, congratulatory, etc.

#4 Create opportunities to identify and fix problems that are systemic.

I wrote about an experience I had when I discovered that employees of a particular department had given negative feedback in our team culture survey. This survey gathers high-level information about departmental performance. Because the metrics we look at in these surveys are systemic, not related to individuals, we are able to address overall issues rather than singling out any specific people, likely unfairly, as the root of the issue. This helps improve morale and performance among team members. When you create opportunities to fix larger issues like this, there will be less need to address challenges on the individual level.

#5 Find time to provide thorough feedback to make your own job easier.

Throughout my career, I’ve heard many managers complain that giving in-depth feedback takes too much time. But, trust me—the feedback you give will be worth it. The single most important thing you can do as a manager is to get the right people on the bus in a good environment. If you’re not providing feedback, you’re not creating that good, productive environment, and you’re potentially letting unseen problems fester. People don’t change if they don’t know something needs to be changed.

In the absence of feedback, team members and organizations aren’t optimized. Transparency and honest feedback, in real time, is the only way to go, and these five tactics will help you give feedback that works.

Gary Swart is the CEO of oDesk, a leading online workplace.

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How a Designer Paints Entrepreneurship

Why your definition of an entrepreneur is probably wrong.

We, entrepreneurs, are hopeless romantics.

We’re suckers for curiosity. We haul ass for lofty goals, sing Valley-speak gospels of Graham and Blank, and, by god, we’re driven by a heart-thumping vision. And as we’ve convinced ourselves that we hate working for others, we also eat uncertainty for lunch. The ideal entrepreneur embodies all of these traits—according to VCs and serial entrepreneurs. But take a second to ask yourself this question and let it percolate:

“Exactly why are you an entrepreneur?”

It took a coffee chat with designer John Maeda to help me realize that, as an entrepreneur, I’d been living under a rock, never having fully answered this question:

1. Mission is only a fraction of an entrepreneur’s DNA

A Sinek-ian response would be to state a company’s mission, like mine: To prolong pets’ lives by bettering access to pet healthcare.

Turns out this statement reveals nothing about why I’m pursuing entrepreneurship—that there could be another team out there who shares the exact same vision as me. Why not join them instead? If I’m truly driven by this mission, why not join a similar company with more resources and clout?

2. Working for someone else doesn’t have to suck across the board

Before my two startups, I had a brief stint in finance, long enough to convince me that the corporate hierarchy wasn’t for me. I loathed some of my bosses and thought, if this were the case at a company, I couldn’t possibly work for another person. Ever.

But feeling jaded with my job doesn’t necessarily mean I’m fit to take the leap of being an entrepreneur. This could mean that I just haven’t found the right team to work with.

3. Saying money doesn’t motivate you doesn’t make you a true entrepreneur

It certainly helps not to be money driven. If fact, I have better peace of mind because of it. But there are plenty of entrepreneurs who are driven, at least in part, by cash and have been successful.

Not caring about material goods qualifies you to be a kick-ass monk, though.

4. Entrepreneurs firmly believe only they can do what’s best

Maeda’s point.

We’re entrepreneurs because we don’t believe anyone else can do better than what we envision. We assume this highfalutin stance that we—only we—are worthy of pursuing this venture. There’s no one out there like that. Others’ efforts are subpar, which is why we want to take charge. That’s the true calling of an entrepreneur.

5. Start with audacity

With this calling comes a voracious killer instinct to destroy competitors, which Maeda euphamizes as audacity. In other words, having balls. It’s audacity that leads entrepreneurs into hell, your blind sense of not giving a flying fuck about what you’re about to face. I felt this way when I started Luna Pharmaceuticals, and the same feeling permeates since I’ve launched Nibbol.

All entrepreneurs begin with this fervor, then follow one of two paths:

i) Recklessness eventually kills your startup and you fail


ii) You learn, adapt to your roller coaster and survive—building courage

6. Die a slow, painful death

Put simply, courage is confidence with intelligent decision making. You begin to effectively navigate the pitfalls of running a company. Hence, you know what to do when shit hits the fan.

Everything sounds like smooth sailing until you encounter the grim realities of your hero’s journey:

i) You become complacent


ii) You die a slow, painful death, overwhelmed by the fast pace of your environment

Once you’re at the top of the food chain, everything falls into place. You snuggle into your armchair, sinking into complacent comfort, devoid of the euphoric excitement that lit your ass to start the venture in the first place.

In 2013, Maeda left for Kleiner Perkins Caufield & Byers (KPCB) after serving six years as head honcho of Rhode Island School of Design (RISD). Why? Complacency. What’s a designer to do after saving a world-class art institution from the financial crisis, multiplying college applications and the endowment, and refusing to buckle under the pressure of a traditional faculty hesitant to embrace change?

Bounce to greener pastures. Restart that terribly beautiful audacity.

That’s what I did. I was wilting away at my previous company, with the pressure high enough for me to leave everything I loved behind—my girlfriend, closest buddies—and move to San Francisco. I couldn’t pinpoint that feeling exactly, but whatever fallout I had, I wanted that sense of renewal, that sense of rebirth.

I needed a Web 2.0 William.

So now I can purposefully ask myself, “Why am I doing this?”

Is it really because of animal healthcare? Yes, partially. And, of course, we want to change people’s lives. But it’s also because I feel no one else can design and build something as beautiful as my team can.

Pretentious? No.

A lofty dreamer? Sure.

Call this my audacity. And maybe one day with my startup I’ll find courage. Or, perhaps better yet, never. I mean, which entrepreneur wouldn’t want to stay brave, young at heart and romantically foolish forever?

Did you like this post? I’ll update you with more good stuff.

Special shout out to mentor John Maeda, Aliaksandr Hudzilin, Alex Poms, Daihua Ye, and (last but not least) Hedan Zeng for being there every step of the way.

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The power of solving a real problem and making your users feel smarter

How I’ve learned to rely on (and love) Waze

During the month of December my wife and I made our regular trips to and from family members’ houses to celebrate the various holidays. Over the past year (especially since we moved outside of the city) Waze has become a part of all our trips, even when we know exactly where we’re going because you never know when there might be an even better way to get there, but Waze does.

Thanks to all the Waze users out there, Waze (now Google) operates from this panopticon-like vantage point, knowing where all the cars are and how fast they’re moving (sidebar: in my more cynical moments, I’ve imagined how they can use this information to control the traffic, and not just respond to it but I digress…). This means that it has the information to help you get from point A to point B in the most efficient way possible based on the unpredictable real time conditions on the road, making a standard GPS (that felt pretty special only a few years ago), feel dumb.

A UI that would give Jack Dorsey a stroke.

In fact, Waze solves that core problem so well that it didn’t matter that the design has long been a hot mess of chunky lines, more buttons than you know what to do with and costumed, fleshy pink dumplings. To be fair the redesign this Fall offered some nice refinements. All that aside, the reason people love using the product (and as a result, Google loved buying the product) is because it takes a bunch of genuine pain points that everyone who’s driven a car (giant addressable audience) has experienced and makes them go away.

I’d like to call out examples of my two personal favorite features: avoiding traffic (obvs!) and sharing your trip:


Back to our travel adventures… Last month we were headed to the in-laws for Christmas, we hit bumper to bumper traffic before the Throgs Neck Bridge and Waze suggested a crazy, borderline non-sensical, looking maneuver .

Since the product has earned my trust I just went with it and found that the unorthodox move — pulling off the highway and getting right back on before the bridge — helped us avoid a huge chunk of stagnant traffic. We had two similar experiences that same week. Not only does the product help you get to where you’re going faster but it makes you feel like you’re in the know along the way — using Waze can feel nothing short of magical, almost like you’re cheating the system. That emotion is a powerful one and over time builds a really strong bond with the product. We’ve always felt that Foursquare Tips (especially now that you get them serendipitously) often offer that same kind of unexpected magic that makes users feel like they’re getting more out of the world around them thanks to the product.

Say goodbye to all those “What’s your ETA?” texts.

My second most-used feature is sharing my drive. It’s a dead-simple way to, once you’ve set off on a trip, share that trip with someone else. The best part is that when they click on the link, they’ll get a map in a mobile web view with 1) a little dumpling moving its way across the map and 2) an accurate estimated ETA based on how far away they are and the traffic between them and their destination. All of this replaces the age old “What’s your ETA?” use case for all parties involved and you’ll be surprised at how nice it is to know exactly where a loved one is on a long trip to/from you as you see that plump little dumpling inch its way across the screen.

I’m personally partial to Mario’s raccoon suit but you get the point.

There are a bunch of other things Waze does a good job of (and many that feel superfluous ) but they’ve done an amazing job in ensuring that their core features solve real problems and in the process make their users feel more powerful — that is ultimately what building a great product is all about.

How is your product helping your users become a better version of themselves?

If you’re someone who drives, I highly recommend you give it a shot.

Further Reading

The power of solving a real problem and making your users feel smarter

 — cross-posted to my regular blog

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Pizza Hut #fail : 5 Easy Steps to Social Community Management

How One Hungry Guy Could Have Become a Brand Advocate

This screenshot is a clear example of customer service and social community management gone wrong on social media. When a customer takes the time to let you know that your technology isn’t working properly, telling that person to fill out a help desk form is more annoying that being ignored entirely.

Your customer is part of your social media community (whether you like it or not).

In the example above, all Pizza Hut had to do was acknowledge the causal factor (the iPhone app sucks, and nobody seems to care), and solve the main issue (Doug wants a pizza). That obvious fail aside, here’s the other thing that Pizza Hut failed to recognize: Doug Karr is a social media influencer and a major pizza enthusiast. Oops.

Doug has 31,000 Twitter followers and runs Marketing Tech Blog. He gives talks around the country as to how to use social media for marketing purposes, and as such he also gives examples of What Not to Do. This particular example is now in a presentation he gives about customer service on social media, and that’s how I ran across it. (Doug and I co-presented a social listening webinar on social media monitoring across the business organization, incidentally, and this example is in it.)

Social media community management is something that you need to do if you maintain a social media presence, whether or not you’re planning on an active social media community marketing program. Your customers are plugged in and online, and they are going to use the channels available to them to get your attention. With that in mind, this example illustrates a few key points that you want to consider when using your media channels for social community management:

1) Don’t pass the buck.

Whether or not you’re in the department that will actually fix the issue being reported is irrelevant. If you’re a human person and can address the issue being presented to you by a customer on the channel you manage, it’s your job to make an effort to address the issue.

2) Have a process in place to manage customer service requests.

People will use your social channels for customer service issues. You as a brand need to have a method to receive those messages, respond to them promptly, and route them accordingly. Some customer service software (Zendesk being one) now have functionalities that allow you to create a ticket from a tweet, but it’s really not that hard to do it the old fashioned way. Hopefully, there is a human running your social media account, and that human should understand both how to respond to a customer and how to make sure that the issue gets relayed to the appropriate person.

3) Use a good social media community management tool to identify influencers before you leave them annoyed and hungry.

Any good social media marketing tool will have community management features that give you the basic profiles and stats on a person who has engaged with your brand. If Pizza Hut’s social media marketer had been using that tool, those stats would have been front and center.

4) 1:1 customer engagement is an opportunity. Use it wisely.

When a person is taking the time to engage with you, this is an awesome opportunity to make a great impression and create an actual brand advocate. Awesome impressions are what spur good social media community cultivation. Making your customer feel heard is important; solving the issue is a chance to turn that person around and into an ardent fan. Excellent customer service is one of the easiest, best ways to get people tweeting about you in a positive way, and illustrates a brand promise that you actually care about your customers.

5) You’re human. Act like it.

If someone asked you for directions on the street, would you tell them to pull out their iPhone and use Google Maps? (If the answer is “yes,” you should definitely consider a career that doesn’t interface directly with customers.) I’m going to give us humans the benefit of the doubt here, and assume that people are generally nice and overall want to help each other out with the easy stuff. If you’re having trouble distinguishing where you should go above and beyond to help someone, just pretend that the person is your Mom. Would you tell your Mom to fill out a customer service form? I hope not. (And if your answer is “yes,” that’s the wrong answer. Trust me. Ask your mother.)

Good social community management happens when we act like people. The good news is that, as people, we have an instinctive understanding of community. In this particular example, just having some empathy for how someone feels when he’s hungry and hampered by a technology issue that’s keeping him hungry should have been enough for that anonymous Pizza Hut employee to take the happy path to customer satisfaction by making sure that Doug got his pizza.


The end of this dramatic story of an absentee pizza ends happily for Doug: Doug really did order from Papa John’s. And he ate that pizza. And since then, he’s ordered more Papa John’s pizzas than he would have otherwise. As for Pizza Hut, their iPhone app reviews would indicate that they still have some issues to work out, but it does now have 4 stars instead of the 1 star it had at the time. Hope for everyone!

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Enough with the ROI. Just follow your curiosity.

Leigh-on-sea/ ian sanders

Leigh-on-sea/ ian sanders

The guy across the table wanted to know…

“But what’s the actual ROI of being on Twitter?”

I muttered something under my breath by response.

Then I took a deep slug from my glass of Rioja and started telling stories.

I told him about the time I was at my kitchen table in Leigh-on-Sea, thinking out loud on Twitter about whether I should go to South By South West or not. And how I got an instant reply from a woman in Chicago inviting me to co-host a panel with her.

Then I told the story of when I’d tweeted that I’d seen the musician and entrepreneur @DaveStewart walking down Wardour Street. Dave tweeted me back, igniting a series of events that not only resulted in us meeting, but also in a random connection with his book editor who ended up publishing a book of my own. Yep, that book only happened because of a ‘blink and you’d miss it’ tweet.

And then I told him how one of my current gigs writing for the Financial Times started out when I met my editor on Twitter, after we engaged in a conversation with the management writer Tom Peters.

I explained my strategy . There was no strategy. All I did was follow my curiosity and enjoy the ride.

I showed up and stuff happened.

Like earlier this year when I tweeted from York train station that I was headed to New York that day (Long day ahead, doing ‘the Yorks’ in one day, I’d tweeted). I got a reply from a guy named Matthew Stillman asking to meet for coffee in NYC. Two days later we were standing at Stumptown sharing tales of following our curiosity over good coffee. Matthew told me:

“If you follow your curiosity to the smallest corners, you’ll find tremendous light there”.

That rung true for me. Not just on Twitter but across my life.

I don’t focus on a ROI, I just stay curious.

(So what’s the ROI of posting on Medium? Who knows? This is my first post. Come back and ask in couple of months…)

If you’re interested in living a more curious life, I’ve just published a little book ‘On Being Curious’. It’s available on Kindle for — the price of an espresso — and will only take you thirty minutes to read.

Ian Sanders is an advisor, a Financial Times writer and a business storyteller. He’s driven by coffee and curiosity.

Further Reading

Enjoy the ride. Suggestions for choosing a more curious life.

 — At the weekend I took my kids to a local amusement park.

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