The Next Social Network

A decade ago people were flocking to Facebook and Twitter. Then along came Instagram and the cool kids (e.g. 18-25 year olds) jumped on board, many of them abandoning Facebook and Twitter for the shiny new network. More recently, Snapchat has become the dominant social network of choice for millennials, attracting advertisers eager for young eyeballs.

Now we’re seeing Snapchat mature a bit; both in the people it’s attracting and the business models it’s deploying to monetize them.

“Snapchat’s core audience of 18-to-24 year-olds is nearing full saturation but 25-to-34 year-old millennials will provide further growth…” — AdAge

It makes sense. There is a finite number of 18-24 year-olds out there and, according to Comscore, Snapchat has saturated that segment. The only way to continue growth is broaden the age range, which is happening naturally thanks to network effects.

More Eyes = More Money

Of course, Snapchat are aware of these trends. They know more accurate audience targeting leads to higher click and conversion rates, and that’s hot money for advertisers. Seeing a bigger opportunity they introducing Audience Match, a system that enables marketers to “…take existing lists of email addresses and mobile device IDs, and anonymously match that data with Snapchat’s own pool of consumer data, allowing enhanced ad targeting.” (full article) Spooky? Not really. Companies have been doing this for a while.

But For How Long?

Question is, how long will this last. Parents sign up for Snapchat to see what their kids are doing. More people are seeing yellow ghosts and deciding to hop on board. Long time users are now the old guard. And so it goes. This trend will inevitably lead to the younger generation feeling like Snapchat is old news, and they’ll look for something else.

With an older audience moving into the platform it begs the question: “When will the younger–typically trend-setting–audience find a new network?”

What will the next social network du jour be?

Does it already exist? Instagram is making a play to be dominant again. Facebook keeps experimenting with its properties. Twitter is grasping at anything it can to stay in the game. Seems like the field is ripe for a new player.

My guess is there’s a kid in a dorm room somewhere with a silly idea. By luck more than anything else, that kid will connect with the right audience and the right VC at the right time and become the next cool thing. They’ll catch lighting in a bottle. You’ll see them on TechCrunch, ProductHunt, and Times Square billboards. You’ll install it and tell all your friends. They’ll get press in The Journal and The Times. They’ll grow and monetize. People like me will write articles like this.

And the cycle will repeat.

What do you think? Let me know:

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Simple Document Collaboration

A VC client recently asked me:

“What’s the simplest way to upload a few documents about a company or deal and have a group discussion about them?”

They want to be able to have the pitch deck, pro-forma, legal docs, miscellaneous spreadsheets, PDFs, and other documents about a deal in one place with a single conversation thread about the deal below the list of documents. Simple enough, but is it?

The Use Case

  • Low-friction high-speed communication is very important to them.
  • Documents could be anywhere (Dropbox, Google Drive, Box, attachments), so platform agnosticism is important.
  • Their team is hardly ever at a desk, so a great mobile experience is critical.
  • Some of the people they work with (investors, analysts, etc) won’t install something new just for this. They need to be able to collaborate via email, because face it, email is still a thing and it’s not going away.
  • They don’t want to learn a new system or tool. It should integrate with their existing workflow.

I’m not aware of a tool that does exactly this, so I began thinking about the tools this client already uses and how they might adapt them for this use.


No doubt Slack is the pretty girl at the dance right now. However, there are valid concerns about it being too easy to use, allowing people to be lazy and rely on the fact that they posted something to mean that everyone else saw it and understood it.

Usage: Create a new channel for each company/deal in Slack. Keep all discussion about that company/deal in that channel.


  • Easy to use
  • Great UI and usability
  • Good mobile app
  • Easy to limit participation on a per channel basis
  • Lots of integrations with 3rd party services
  • Easy to invite others to collaborate
  • Private messages with one or more people via DM
  • FREE


  • Not everyone will want to use it on mobile since they have to install the app.
  • That ‘another thing to check’ feeling.
  • No easy email integration for people who still work from their inbox.
  • No daily activity report without a 3rd party integration
  • Can be hard to keep important discussion separate from chatter

Basecamp 3 (not previous versions)

Basecamp feels excessive for such a simple task. There are lots of tools that simply aren’t needed and might be confusing to people who aren’t familiar with them. The simple threaded messaging and ease of collaboration via email might be worth the baggage.

Usage: Create a project (a.k.a. a “Basecamp”) for deals, turn off all the other ‘Tools’, then create a Message for each company/deal and keep the conversation threaded there.


  • Easy to use via email with the right notification settings.
  • Good mobile apps.
  • Easy to invite others to collaborate.
  • Daily activity reports via email.
  • Easy to assign and track tasks via To-Dos (if that’s important).
  • Private messages with one or more people via ‘Pings’.
  • Applauding‘ a message is fun.


  • UI can be a little clunky and difficult.
  • There is a lot of cruft in messages sent via email. Basecamp hasn’t figured out how to strip email signatures and such from messages, so things can get cluttered real fast.
  • Difficult to have different groups of people without creating a ‘Basecamp’ for each deal/company, which feels excessive.
  • Campfire, the realtime chat that’s built in, totally sucks compared to Slack.
  • No good 3rd party integrations, but the API just opened so that may change.
  • $79/mo (not a deal-breaker, but still).

How would you solve this problem?

I’ve not found anything that does exactly what this client needs. Maybe I didn’t look hard enough, maybe it doesn’t exist. So tell me… how would you solve this? Do you have this pain, too? Should we build an app to do solve it?

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Can Microsoft leverage LinkedIn’s Platform?

Interesting news about LinkedIn today. Seems Microsoft is acquiring another gateway into the corporate world to strengthen their hold on office productivity and connectivity.

Could an Outlook integration speed business connections? Could Dynamics add a new dimension to CRM intelligence? Sure. But that’s just scratching the surface, and it’s making bold assumption about whether Microsoft can utilize LinkedIn’s platform effectively and that LinkedIn will thrive under the Microsoft umbrella. Based on the track record Redmond has established with previous acquisitions that’s a tall order.

It’s no secret LinkedIn leaves a lot to be desired in the user experience department. Listing only the most egregious issues with the UI a bizarre interaction patterns would take many more words than I’m willing to tap out on this small screen. Suffice it to say, it’s one of the least delightful experiences among large-scale social networks.

Microsoft isn’t exactly known for their prowess with pleasing experiences, either. The interface of the Office suite is held prisoner by the vast numbers of enterprise users who will complain quite loudly if any ambitious experience designer tries to move the cheese. Knowing this, a betting man would say LinkedIn won’t get easier to use any time soon.

A gap in the market?

Assuming LinkedIn stagnates (like Skype) there will be an increasing gap opening among savvy business users who become more and more frustrated by a ham-handed LinkedIn UI. Where will they go?

Nowhere yet. Unless and until Facebook decides to enter the fray. Hypothetically, Facebook could “flip a switch” and turn on business features that would make LinkedIn look like a toddler trying to tie a Windsor knot. All the baseline mechanics are in place, they wouldn’t need to change much.

Is it a stretch? Sure. But we might just see a new player in the professional networking space soon. And it could happen faster than Microsoft can close the books on the LinkedIn deal.

What do you think?

Carl Smith at Converge SE - photo credit Jason Beaird

Redesign our Design Thinking

ConvergeSE is one of my favorite events. It’s generally swarming with smart people sharing smart ideas. But all this talk about design thinking has me thinking about design thinking.

We need to rethink how we think about design. We focus too much on aesthetics, not enough on outcomes. Focus should be on pleasurable and frictionless achievement of the user’s goals. Sometimes we let visuals get in the way. We have to leave our design aesthetic ego at the door and focus on positive outcomes for the user.

Just as the great Frank Lloyd Wright said, “Form follows function”.

Photo Credit – Jason Beaird



The balmy afternoons of summer are coming. Kids will be out of school and some of them — the enterprising ones, at least — will be hauling card tables down to the curb to peddle their homemade versions of that cool refreshing drink.

Remember when you were a kid? Sitting on the sidewalk waving at passing cars, hoping one of them would stop and trade you a quarter for a dixie cup of liquid sunshine. Me too. It was the first venture into business for many of us. Our first taste of capitalism, powered by sugar, water, lemon juice, and little hutzpah.

There was no excitement like seeing someone pull their car over, stop, and walk over to that little table. And no reward like counting the quarters at the end of the day.

So the next time you see a lemonade stand, stop and buy a cup. It doesn’t matter what it tastes like or if you actually drink it. You’re encouraging a kid to pursue business, to understand commerce, to do things for themselves.

That empowerment is worth far more than the price of a cup.


A Dangerous Groove

Racing drivers call it “the line”. It’s the fastest way around the track. Each driver might have a slightly different line that works for them, and that’s okay. Finding it can be difficult, but the payoff is massive when you do.

Running a business is a lot like motor racing. You must constantly push your machine to the limits. You want the best parts on your car, and every one of them to perform at it’s best. You can’t afford to take it easy. The competition is in your mirrors and victory awaits.

If everything seems under control, you’re just not going fast enough.

Mario Andretti

It feels great when things are going well and business is smooth, consistent, and predictable. You’re in a groove.

You settle in and push the throttle. Lap after lap, things are working. The machine is running beautifully. Business is doing well.

It’s easy to stay in a groove. It’s comfortable. And dangerous.


Like everything else, grooves change over time. It’s gradual, but they start to deteriorate. Before you know it, the groove has deepened to the point it’s difficult to get out of. It’s become a rut. And at that point it’s too late. You’ve lost performance, or worse, crashed.

The most damaging phrase in business is “We’ve always done it this way!”

Grace Hopper

Just like in racing, if you stay committed to one way of doing things — one groove — for too long you risk getting trapped in a rut that slows you down.

Sector Times

Racing drivers measure the time of every lap around the track. Then they break the lap down into sectors of the track to understand their performance with even greater precision. The sector time is a metric. A racing driver looks at many data points, their KPIs, to determine where performance can be found (or lost).

Telemetry from a Ferrari F1 car at the Hungaroring

This chart shows throttle, braking, steering angle, speed, and several other KPIs. Drivers and teams analyze this data on a lap-by-lap basis to understand where they can improve performance. This steady and ongoing analysis is how they ensure they’re not falling into a rut.

Watch Your Metrics

You must constantly analyze your metrics to make sure your groove is still performing. Otherwise, you risk settling into a rut. Maybe it’s resource utilization, sales pipeline efficiency, shopping cart abandonment, or click-through rates. Your metrics might be on-boarding rates, search rankings, or any other of myriad ways to measure the performance of your business. It’s important to identify which metrics matter, and keep a close eye on them.

The only way to improve your business is to measure the right things and monitor those measurements closely. Things might feel great in the groove, and they are. Stay in that groove as long as it’s working for you. Just make sure you’re not digging a rut in the process.



I feel like a jerk. Airing my trials and tribulations out on the open Internet. It feels undignified.

“Nobody cares about your problems” they say.

“We have to maintain appearances” they say.

Well, maybe it’s time to say “screw that”. As Greg put it recently, we’re losing the web we once knew. The one that was personal, casual, and authentic. Sure, people post all over Facegram and Instabook and Tweeternet, but it’s just not the same. It’s too homogenized. Yuck.

Maybe I’m just succumbing to my inevitable inner curmudgeon, but like Greg, I miss the days when people posted authentic thoughts and commentary on a site of their own design (or at least their own domain). Going to someone’s site felt friendlier, more real, like visiting their home. You could easily see the other things they said and did. It was one-on-one, like a conversation.

Seeing their post on [insert social site here] feels like a passing comment in a crowded room. And who knows how the bots decide what to show you? Meh.

Maybe we, the people who helped build this thing, have failed. We should have seen this coming. Maybe we did and couldn’t act fast enough. Maybe our collective hubris clouded our vision.

What goes around…

Life — and everything in it — is cyclical. Computing was once done in a hub and spoke system where distributed weakling terminals connected to powerful centralized mainframes. Then the personal computer decentralized the world and put all that power on our desk, and later in the palms of our hands. Now we’re putting everything in the cloud and in the hands of a few giant companies, centralized again. Who knows what they’ll do with it all.

Our Internet lives used to be decentralized, too. Personal websites and blogs were the norm. Now we’re centralized on social networks and blogging is a dying art. My hope is that like everything else, we see the cycle come around. That a renaissance of thoughtfully designed personal websites will make the web fun and entertaining again.

Just think of it. At the very least we’ll be in control of our thoughts and photos. We’ll be producers again instead of a commodity being sold to advertisers.

There’s still hope. At least I’d like to think there is.


Presentation Tips

A friend of mine recently emailed me with a question:

I’m leading a workshop at an upcoming conference and I’d love to pick your brain a wee bit.

Do you have any advice, recommended reading, or informational wisdom-nuggets that helped you along in your presentation path?


A humble speaker newb

My Response

I’m not the most qualified to give advice on public speaking, but here are my quick thoughts anyway.

Best bet is just be yourself. Practice your talk at least 10 times in private. Speak slowly and pronounce everything clearly. If you can, make a video of you giving your talk. You’ll notice any strange mannerisms or verbal oddities you’ll want to correct.

Keep your slides simple. An evocative image with a few words is better than a paragraph. Don’t read from your slides, read from your notes (or better, memorize your material).

In a workshop format just try to keep things casual and conversational. You might be crazy nervous the first few times and that’s okay. The butterflies never go away completely.

Recommended Reading

(disclosure: these are affiliate links)

Hope that helps, and best of luck!


Non-Disclosure Agreements

“We need you to sign our NDA before we can discuss the project with you.”

From time to time a potential client will say this or something like it. I get it, they want to protect their intellectual property from the competition or the general public. This is an understandable concern, and we don’t take our client’s concerns lightly. We work with some startups, and they seem to be more sensitive than most companies. Larger companies are oftern trying to protect something they’ve already invested a lot of time and effort into. However, NDAs are not a great tool for protecting information. Mark Suster covered this in 2009, saying…

You shouldn’t worry about NDAs because they’re mostly unenforceable or unprovable anyways.

No matter the reasoning for deciding to sign an NDA, being careless about signing them can lead to trouble, so we’ve decided to simplify the process. Here’s the how and why.

Most NDAs Are Too Complicated

The problem is no two NDAs are the same. Different attorneys put emphasis on different things, or use slightly different language to describe similar things. If you sign every NDA someone asks you to it can get messy real fast.

At Nine Labs if we sign an NDA for the courtship phase we use this simple one. Here’s the entire thing:

Nine Labs hereby agrees upon receipt of materials from __________________ (“Client”), which contain information of a confidential and proprietary nature, to make all reasonable efforts to prevent unauthorized disclosure, copying or publication of concerned information and to protect it as its own. Without limiting the generality of the foregoing, Nine Labs agrees to take such actions as may be reasonable to limit disclosure by advisers, associates and/or co-workers who may gain access to the concerned information.

Nine Labs agrees to use the information solely for evaluation of the project concerned and for no other purpose without the prior written permission of Client.

Nine Labs shall not be held responsible for information already in the public domain, information which becomes public domain through no action or omission of Nine Labs, or information obtained legally from a third party.

This non-disclosure agreement ends one (1) year after date of signature.

That’s it. No craziness. Simple enough that a layman can read and understand it.

Reviewing Legal Documents Is Expensive

Signing different NDAs with different bits of language simply isn’t practical for a small team without in-house counsel. We’d have pay our attorney to read, interpret, and advise us on each one so we know what we’re signing. 99 times of 100 that’s not a justifiable cost.

Our Master Services Agreement Covers it Anyway

Our Master Services Agreement has robust language surrounding the issues of IP Assignment, non-disclosure, etc., so having multiple agreements which address the same issues is difficult for either side to enforce legally, should that become necessary.

We’ve made a decision to use our Simple NDA for the courtship phase, and let our MSA govern these issues once we actually decide to work together.

It’s Also About Focus

We don’t want to spend out time talking to attorneys. It’s nauseating and costs too much (sorry, Marc). Keeping the NDA process clean and simple allows us to spend more time doing what we’re good at, and what we love.

Next time you get an NDA request, see if you can simplify the process. You’ll be glad you did.


Swim Lanes

Two meters is much narrower than you think. Maybe it’s fine if you’re just lounging around. But if you’re trying to accomplish something, like, say, winning 22 gold medals, it’s a pretty small space to work in. There’s definitely no room for distractions.

Distractions are Toxic

According to Gloria Mark, a leader in interruption science, “once distracted, a worker takes nearly a half-hour to resume the original task”. There are numerous articles on how we’re actually not wired for multitasking, and how distractions kill productivity. We claim to know these things in the modern workplace, yet we fall into the same old habits of distracting ourselves and each other on a near daily basis.

This leads me to one of our core maxims at Nine Labs:

Don’t ask a question you can find the answer to in less than 20 minutes.

The idea is simple, if you can find the answer to your question in less time than it would take to distract someone else and for them to get back on task, don’t distract your team mate with the question. Now back to the swimming pool.

Whether it’s visual design or company strategy, everyone on the team has a specific range of skills and does their best work when they are allowed to focus on performing in that arena. Performance of each of these skills is necessary for the success of a project, and ultimately, the success of the business. These are the swim lanes defined for each team member. Everyone on the team should do their best to stay in their lane and – perhaps more importantly – not drag someone else out of theirs.

Being in your swim lane as staying is a state of flow; focused and productive. Getting out of your lane leaves you blurry and ineffective.

Easier vs. Better

While it might feel easier to ask a team mate a simple question about a project, if the answer lies somewhere in Basecamp, Slack, or a Google Doc, go find it there. Chances are it will just take a few minutes to find it, you’ll know where the answer is, and you won’t have pulled a team mate from their swim lane.

“But isn’t having the ability to ask for help part of the benefit of being on a team?”

Sure it is. Here are a few tips to try (they work for us):

  1. Have a time on the schedule for open team discussion and collaboration. This can be as frequent as you like. Find a rhythm that works for your team.
  2. Create clear signals for when it is and isn’t okay to inturrupt you. For us, it’s having your headphones in. Status messages are also good (that’s why all the chat apps have them). Set your status to ‘Do not Disturb’ when you need to focus. Conversely, you have to respect these signals when you see them and not distract your team mate.
  3. Have a bat signal, use it sparingly. Create a clear structure for what constitutes an emergency and how to communicate that to your team. Don’t abuse it, though. If you cry wolf too much your team won’t take you seriously when you do need help.

What if I can’t find the answer in 20 minutes?

This is bound to happen, so your team should have a plan for what to do when it does.

  1. Poke your head up and see if the person who has the answer is readily available.
  2. Ask if they have a moment to help (this is super-important).
  3. If they say yes, ask the question as accurately and concisely as possible (see: how to ask good questions).
  4. If they don’t know and need to get back to you, unless it’s urgent, post it in your project management system and tag a time to follow up.

Respect People’s Time

There’s a lot more to being an effective team than just getting your own work done. A lot of it is allowing other people to get their work done, too. This could mean overcoming your reflexive tendency to ask for help. It’s counter-intuitive. It’s hard at first. But after putting some structure around how and when you ask questions, you’ll see the team’s performance increase in short order.

So next time you think of asking a team mate something simple, first ask yourself “Can I figure this out?”. You probably can, and that’s better for everyone.