Using AI to Reduce Social Friction

from Katie Harbath

Running off my Friendly CRM idea, here’s another first world problem many young urban professionals have: not enough quality time with friends.

We’re all so busy living our own lives that we can’t find time to meet with the people we care about. Without proactive effort, your social network narrows to workmates and housemates. We have calendar reminders and Facebook events to keep us professionally and personally occupied, but this is all reactive, not proactive. I may want to spend time with a nearby friend, but the friction of reaching out, finding a time, and scheduling a place to meet is just too much.

Why not use technology to remove this friction? My social network is already online in a database, so a machine solution should be able to make meeting up truly effortless.

Reconnect with a Single Button

Maybe I hit a button, and it goes through my contacts (Facebook, email, whatever) and finds who I haven’t spoken to in a while, but who I have had close contact with before. It then finds a hole in my schedule (since it’s attached to my calendar) and searches for Yelp locations within a suitable distance. Bam – person, place, and time are found, and it reaches out to the person in question with the details to determine the final answer. We’ve got Clara for scheduling, so there’s no need for me to be a part of that process.

I see this as being very valuable, as trite as it may seem. There are plenty people in my life who I want to spend time with, but can’t find the time for. Except it isn’t that I don’t have the time – it’s that I don’t have the attention to spare, to find the time and make it work. This app could take care of the attention and find me the time.

All the data is already there in Facebook, your calendar, and Yelp – it’s just a matter of connecting them.

This ‘one button to solve social problem’ solution could be applied to other angles as well. Remember the couple that arranged their entire wedding through sharing economy services? They rented a venue with Airbnb, did catering with Instacart, and had servants from Taskrabbit. Final budget was under ten thousand dollars, in compared to astronomical normal wedding prices. I’m sure all of that required a lot of managing, but what if you made it easy?

Dinner Party with a Single Button

We already have operator boutiques like Magic – what if you took one of those workflows and streamlined it with trusted venues and Taskrabbits? I can tap a button, and a gourmet dinner is prepared at my house ready for my return, along with guests preselected. The what and how parts are easily solved, but the who part is tricky.

There you face the same issue as before – involving other humans complicate matters. But I think I could still hit a button, and it would search my contacts for recently non interacted people the same way, and send them casual invitations “Hey, hosting a dinner at my place on Friday, can you make it?”. Then Clara-ize the feedback until you arrive at a desired number or attendees. Hire the food with Munchery and boom, we’ve got dinner.

Apparently Factory X did something just like this –, and found that they couldn’t get people to show up. Even with human-curated gatherings with new people and down payments of 5 to 10 dollars, people said they would go and then didn’t.

But you could easily solve that with a human aide checking in, or bigger down payments, or people that they know they want to know. Don’t make it blind introductions. Tell them exactly why they chose this person to have dinner with them. Or use the curator’s personal network to facilitate their existing wish lists – maybe garnered from Twitter.

The system could even allow me to select certain types of gatherings using its machine data. I could select categories of friends, like ‘college buds’ or ‘professional friends in the same industry who should know each other’. Or it sees how many friends they have in common, to see who should know who but doesn’t.

My life is easier, my social capital is higher, my friends get to know each other, and it’s all without any extra work on my end.

I suppose what I’m talking about here is a way to add AI to social networking. It was a big jump to put our social circles into databases, but we haven’t yet leveraged that fact and put the databases to work for us yet. It sounds impersonal, but at the end of the day, it will encourage more social interactions. And that’s something we all want, right?

Why Don’t We Have Friendly Relationship Management Software?

There are literally dozens of services out there that help salespeople maintain and develop relationships with prospects. Salesforce, Yesware, Highrise, the list goes on and on. So called Customer Relationship Management tools are key in order to track, remind, and manage these professional relationships. There’s services that tell me who to follow up with when, relevant personal data, the history of our relationship, and everything I’d ever want to know about our relationship.

Yet in the end, I don’t really care about those relationships. They are means to an end – to get a sale. Meanwhile, my life is full of relationships that I truly do value – my family, friends, acquaintances, and everyone else I interface with willingly. Why aren’t there CRM platforms for people you care about?

Spending Time With Friends Is Still Hard

You might say that’s preposterous – if they were truly people you cared about, you wouldn’t need software to remind you their name and background details. But I disagree.

Ever since college, I’ve been amazed at how few opportunities there are as a young adult to connect with anyone outside of my inner circle. I spend plenty of time with my housemates, girlfriend, family, and friends in the regular meeting groups I attend locally. But outside of existing circles, it’s very hard to get together with people.

First one party has to reach out and ask, which is easy to forget to do when one has dozens of lukewarm contacts they’d like to see. Then you have to schedule them into your calendar just the same as a business contact, which is hard since we’re all busy. Then you have to find a place and time that works for both! There is undoubtedly friction here, since even dear friends will often deteriorate down to nothing more than a Facebook Like every now and then.

And yet these are truly people who I care about and want more of in my life.It’s ridiculous. If there were software that helped reduce that friction, it would greatly improve my quality of life, more than any social network app. Instead of creating secondary interactions with online profiles, it would increase the face to face time with real people.

An FRM Would Be Similar to a CRM

What would this look like? I daresay it’d be almost exactly like existing CRM solutions, but plugged into your Facebook and phone contacts rather than Linkedin and email. It would provide relevant information about people you haven’t talked to recently, and streamline outreach, perhaps even with templates like CRM solutions do. The key would be making things warm and personable rather than robotic and forced. That shouldn’t be difficult, given the wealth of information people already share to their social networks. There’s already bots that can post statuses that sound like you – why not use that power for outreach?

The friendly CRM could even prompt me to connect with friends based off what we share. If we both post about similar topics – thats a chance to reach out. If it’s been a year since some significant event, time to reach out. Have an unscheduled lunch hour? Pick a valued friend you’ve been meaning to see, and drag and drop to quality time.

Maybe it could prompt me to share content I’m already reading with friends who it knows would like it. Did Joe just post about Trump recently? Present me with an autocomplete template to send my thoughts on the piece I’m reading right now to him and spark a reconnection.

Integrate with Yelp and help us remove the friction of finding a conducive nearby place. Integrate with Open Table and take away the friction of a crowded restaurant. Cross reference my other dear friends and source up the people who have the most interests in common to allow me to double dip and host multiple friends at once. The options are endless, the data is already there, and the need is real.

You know when you reach out to a loose contact to ask a favor, and genuinely wish you were just reaching out to be friendly? I hate that feeling, but not enough to actually schedule warm contact with friends. There’s friction, and no reason to reach out today versus any other day.

That’s the gap this software would bridge – reasons to reach out, while streamlining the event itself to be as easy as possible.

Do Entrepreneurs Create Waves or Merely Surf Them?

Image from BillSOPhoto

There’s a 19th century idea called the ‘Great Man’ theory, which claims that history can be explained by the impact of ‘great men’ who used their power in a way that had decisive historical impact. People like Napoleon, Shakespeare, Muhammed, and the like who pushed humanity forward using nothing by their own charisma, wit, and understanding.

The idea has mainly fallen out of favor since World War 2, as critics have noted that such men are products of their society, noting that ‘before he can remake society, his society must make him’. In other words, their personal input was indeed critical, but it was more the result of him being in the right place at the right time than who he was. They weren’t the only one who could bring together the several converging movements into one (so the argument goes), but they happened to be the one who did.

Great Men of Tech

Today, the concept has resurfaced in tech, as men like Steve Jobs and Elon Musk are hailed as unique visionaries who explicitly created our modern reality. The MIT Technology review does a good job of pointing out that government subsidies play a large part in these successes and how the great man myth is harmful, but I don’t think it dispels it entirely. Yes, such men are products of society, and happened to exist at a time when converging technologies allowed them to catapult things forward, but their own agency has some say in the matter.

It’s unlikely Steve Wozniac would have made Apple such a beautifully designed company, for instance, and unlikely that Martin Eberhard alone would have turned Tesla into the dynamo it is today. Without their ‘great men’, these companies would not have been driven to accomplish what was previously thought  impossible or crazy.

Could someone else have pushed them in the same way? Would any visionary, controlling perfectionist have done instead? Perhaps. What, then, are the key personality traits that one would require for a modern, commodified ‘great man’?

It is not their peculiarities. One of the reasons why the theory is harmful is because it deifies the men and puts their eccentricities on pedestals. There’s a sense that if one wishes to be the next Steve Jobs, one must take acid, wear turtlenecks, and only eat fruit.

But these are not what made such people great. It is important to distinguish which personality traits are frivolities, and which were instrumental in their success

There are a few personality traits that will always be helpful – the ability to pattern match across many different topics, a drive towards perfection, and towering ambition all help. But even with all of these, one must have a good deal of luck, and the ability to see where the world is headed.

Luck: The Only Personality Trait That Matters

Some would argue that foresight coupled with luck is the only important trait.

In Shane Snow’s Smartcuts, for instance, he profiles Sonny Moore, an emo band guitarist who got decided to jump genres and start producing electronic dubstep music. He happened to start making EDM right as the genre became massively popular in the US, and now, as Skrillex, he’s one of it’s biggest stars. Snow notes that it was his ability to sense the impending dubstep wave that allowed him to produce the right stuff at the right time and be successful.

Bryan Lim, the founder of, is another person who benefited from the EDM boom. He was the only person selling rave gear stateside when the craze hit, mostly because he was frustrated with dealing with Chinese manufacturers who had month-long delivery times. While he acknowledges that he worked his ass off making the company, he says that his success was mostly luck and good timing.

Is luck and good timing, then, the only personality trait we should maintain? What should an ambitious young person who wishes to make an impact on the world do, if all who come before him were lucky and nothing more?

Passion + Luck > Foresight

I refuse to subscribe to this new ‘Lucky Men’ theory, that people are successful due to their time and place of life and not due to decisions made during it. It should be put down just as the Great Men theory was. Why? I believe the dichotomy here is not that of destiny vs agency but of passion vs opportunity, the same quandary I examined in Does Passion Trump an MBA?.

To be successful, one should not examine the times and find the wave that is likely coming to a head soon. One should not try to predict the next EDM boom. Jumping into a field because it looks promising will lead to failure, no matter how good the numbers look. Instead, one should jump into fields that one is authentically excited about, and use one’s own intelligence to see how it can fit into the times.

Skrillex and Bryan didn’t sense the coming EDM boom and jump ship – they were already passionate about what they were doing, and would have continued doing it regardless of market conditions. They were pursuing passions more than creating businesses. Even Elon and Steve were pursuing passions – Musk didn’t know anything about rockets, but he knew he wanted to, so he dove into all the regular texts on the subject, until he could count himself as an expert. He wasn’t doing that to make money – he did that because he cared about getting to Mars.

Then again, if they had decided to pursue passions in underwater basket weaving, farming, or horseback riding, it’s unlikely they would become ‘great’. Why? These are unscalable passions, that only affect a few people no matter how good you get at them. Integrate one of these with a technology wave coming to a head, however, and you’ve got something big. Run a farm using drones, track horse vitals using wearables, or make a platform that teaches people how to weave, and now we’re talking great.

Here, then, is my vote for the best way to become a ‘great person’, regardless of the times: Turn inward to discover what you re truly passionate about, and master it. Then turn outward, and see how evolving developments in your time and place are affecting your passion. Then put yourself in the right place with the right network to leverage your knowledge of the craft and the times to make a difference.

Find your passion, then get an MBA in the times to maximize your impact. How’s that for a recipe for greatness? (genuinely curious here)

Your Job As A Nontechnical Startup Employee Is Convincing People

from Marina Noordegraff on Flickr

Paul Graham has a saying that goes something like this: “In startups, you either make the thing, sell the thing, or pick up toilet paper at CVS.”

Harsh view of Operations people aside, I agree. Maybe we could say that ‘you make the thing, sell the thing, or facilitate that making/selling.” As any company grows, the number of administrators increase, but in startups, it’s mostly makers and sellers. Look at the classic founding duo – a technical guy makes it, and a nontechnical guy sells it.

It’s easy to forget that once startups blow out to ten to fifty people, but nothing has changed. If you’re nontechnical and in a startup, you’re a salesman. How far removed you are from the customer depends on your role, but strip away the business lingo, and everyone is convincing people the product is worthy (of their money, time, attention, whatever).

Think about it. Sales is convincing people to buy directly. Marketing convinces people to notice. Customer Support convinces customers to continue buying/noticing. Press Relations, Business Development, and Fundraising are all convincing journalists, partners, and investors to do something for you.

Who you are convincing and what you are convincing them to do varies, but at the end of the day, it’s all about making them believe in your product. If they do, something good happens that either prompts buys, or is a buy itself.

Not Selling, but Convincing

Therefore the best nontechnical startup people are the best convincers. It’s not about pure selling ability – this isn’t a used car. It’s about getting the person to believe in your product. The way I see it, there are three parts to a good convincing: 1)finding the right person, 2)connecting with them, and 3)the Convince.

Finding the right person isn’t hard in today’s digital world. Everyone has a guessable email address or digital presence of some kind. Sales prospectors have this down to a science, and customer service reps have people come to them. But for marketers and the rest, it’s a lot more freeform.

Connecting with people is tougher. Either you network your way into a relationship, or you do a good job of marketing yourself and your product. Assuming they stand to gain from talking with you, you can even do the cold email intro. Whether it’s warm or cold, now you’re at the Convince part.

Convincing is either Manipulating or Communicating

The way I see it, there’s two ways to convince someone of something: either you believe it yourself, and communicate that to them so they share your belief, or you’re adept at manipulating them to believe something you do not. I think we can all agree that salesmen who believe in their product perform better than even the best of manipulators, but go ahead, find studies that prove me wrong. At any rate, if you’re at a startup, you are probably a believer. Otherwise you’d work in corporate or another more stable job.

Therefore, the ambitious nontechnical startup employee who wishes to improve at their job must practice communication. Your success at your job is directly correlated to the skill at which you can find, connect, and convince relevant people. And given that any web-savvy virtual assistant in the developing world can find and send emails, the only thing separating you from them is your ability to communicate the company’s value proposition clearly and succinctly.

It’s one part art and one part science. There are right ways to approach people, and there are certain ways to convey your ideas in an attractive way (covered in Carnegie’s classic How To Win Friends and Influence People). But talking and negotiating is an art, and lots of it relies on your conviction and charisma. I don’t know if there’s one right answer in that regard. It depends on what your value proposition is, and how they stand to gain. (who you are vs who they are).

I’ve drawn lines rather black and white here, as I often do in short blog posts. There are a few aspects of nontechnical startup work that aren’t convincing people, but those veer into the technical, like optimizing marketing campaigns. But I look at my days as a Marketing/Partnerships guy, and see that half of my time is strategic connections over email, and the other half meetings or digital conversations where I present and convince.

Am I the only one that feels this way? What are some ways we can all get better at convincing people, beyond the classic sales tactics?

Elle Luna: An Artist at Best or Designer at Worst?

Ever heard of Elle Luna? You’ve probably touched her work. She was a crucial designer behind three of the biggest apps in Silicon Valley – Medium, Mailbox, and Uber. Uber 1.0 was super ugly until she came around, Mailbox was built under her design lead, and she scaled Medium from the earliest days.

Sounds like an accomplished, fulfilling career, no? Elle didn’t feel that way. She jumped from success to success never feeling content. She started having dreams about a white room with nothing in it, visions that she couldn’t escape. So she did the logical thing, and went to Bali for 6 weeks in order to find herself.

In Bali, she spent her time in a hut without walls, painting portraits of local villagers and discovering a love of textiles. The experience empowered her to pursue artistry full time, so she went back to San Francisco, found the white room of her dreams on Craigslist, filled it with paint, and has since left her designer days behind her entirely. Pretty heartwarming, right?

She even wrote a viral blog post about the experience that turned into a cult favorite book: The Crossroads Between Should and Must. Should is all the things that society says you should do, and Must is what your inner self says you must do. Needless to say Elle has embraced her Must, and she encourages many others to do the same.

It’s a fantastic parable for doing what you love. Girl works hard, hits the big time, isn’t satisfied, and quits the real world to go do what she loves. This is straight out of Eat, Pray, Love.

When I heard Elle’s story, I loved it. But then I saw her art, and the narrative changed. Her story morphed from a guiding light to a cautionary tale. Something about the whole thing seemed inherently wrong to me. I realized that my greatest fear in life is that I don’t live up to my potential, and to me, the story of Elle Luna is exactly that.

Note: I have no business telling Elle how to live her life. She’s happy, she’s making a living, she’s creating art, and what I think is completely irrelevant. I don’t mean to disparage her or what she’s doing. But her story is too perfect of a parable. not to share.

A Tale of Passion Pursued, or Potential Eschewed?

I don’t like Elle’s art. It’s not that I hate it – it just doesn’t speak to me. I think her moon banners are trite, her portraits unexceptional, and her sketches ordinary at best. It’s professional art, but nothing special when compared to other professional art. That’s my opinion, and it’s moot, since she has an audience paying hundreds of dollars for it.

But that’s the thing – Elle didn’t start off as an artist. She was a designer, and a damn good one at that. Look at how gorgeous AND useful her app designs are. They’re pretty, simple, and effective. Few can deny the value that she has added to those projects.

Meanwhile, I’m not the only one who doesn’t care about her art. Some love it, some don’t care, and most people aren’t affected; whereas her designs were unanimously praised, and used the world over.


As John Maeda phrases it above, design is the intersection of art and science (subjective and objective value in my phrasing), both beautiful and useful. She went from being a talented designer who positively impacted millions of peoples’ lives in the most meaningful of ways (reading, communication, transportation), to an unexceptional artist who makes a few wealthy art collectors’ lives marginally better. The value of her creations became subjective and limited in scope.

Must Is Easy When You’re Elle Luna

What if everyone did that? What if everyone chose Must over Should? That’d be the classic artist utopia offered after the Singularity, when robots become capable of taking care of humanity’s every need, freeing us to become artists and do whatever we like (or Must!).

But in the meantime, somebody needs to clean the toilets, take out the trash, and sell products. I doubt any of those are personal Musts, which means that if we all followed Elle’s lead, we’d all lose our jobs. And most people aren’t as privileged, successful, or wealthy as Elle Luna to make the artist jump sustainable.

Would she have been a successful artist if she didn’t have that glowing design career behind her? What if she starting making art right after high school instead of going to IDEO? Would anybody care? Would she be successful? Would she love her life more?

Those are big what-ifs, but unless you have 3 triple A apps to your name, they are the questions you grapple with, not Should vs Must.

Here’s another angle – what if her art was as successful as her designs? What if her personal brand was as well known as Ubers’? Art offers a very different kind of value than scientifically useful design, but it is value nonetheless. Making something people like to look at isn’t quite the same as streamlining daily processes, but both have value. Indeed, the value of a designer is a commodity, while the value of an artist is not – any talented designer can streamline a process, but the work of an artist is 100% unique.

An Artist at Her Best, or a Designer at Her Worst?

The tale of Elle Luna can be told as that of an artist embracing her true calling after years of languishing under the Man, or it can be told as that of a designer throwing aside her impressive talent for helping others in order to help herself. I see it as the latter, but I can understand why someone would see it as the former.

I come off as an arrogant, unfeeling Objectivist in this way. Who am I, or Ayn Rand for that matter, to tell Elle or anyone how they should spend their life? Then Rand is just another Man doling out Shoulds and holding us back from our Musts, which is not what I believe. I’m all about Musts and loving your job. But I’m also all about adding value to society.

If Elle is happy as a designer and ecstatic as an artist, should she forego that extra joy in order to pay her dues to the rest of the world? She owes us nothing, but if the Venn diagram below is apt, art is more of a passion than a purpose. (or maybe I’m just a fogey businessman who doesn’t understand the value of art).


Can Must Come With Should?

If Elle’s lifestyle is happy, fulfilled, and sustainable, that’s all that matters. It’s once she tells others to do the same that I get uncomfortable. I disagree because I value design for many over art for the few, and think that it’s simply not possible for most people to embrace their Musts today (without her star power).

Perhaps the right answer is a balance. For now, everyone does as they Should, and needs more Must in their life. But overcorrecting the scales and going full Must is just as bad. Perhaps to live well, one both Should and Must.

An artist who loves making art nobody else loves is just as bad as a scientist who spends their life writing theoretical papers with zero applications. Both love their lives, both struggle to get paid, and nobody (other than them) cares. If everyone embraced their Musts (Kant’s categorical imperative), the majority would be making stuff nobody else cares about. Isn’t a world where we’re making stuff we love to make that’s also loved by others the best possible? That’s the world I’m groping for.

Is Elle Luna in that world? I suppose she is, since she’s enriched my life and millions of others with her design, her story and (apparently) her art. And if she inspires even one more person to embrace their Must rather than their Should, she’s a true hero.