The definition of an intrepreneur - three ways big companies can harness the entrepreneurial power of their people

There are many reasons companies are drawn to the notion of innovating, but three emerge as the most salient and widely-applicable:

  • The existing business is built around older technology or serves customers in antiquated ways
  • It is interested in a product extension perspective (i.e. retooling existing products to be more relevant across a variety of fields)
  • A threat looms within the company’s – or an adjacent – industry that could render the existing business irrelevant

The problem facing the majority of large companies looking to innovate is not a lack of interest in innovation or a rationale to invest behind it, but a systemic stymying of the entrepreneurial spirit within their own companies. This spirit which is the core qualities of an entrepreneur is a key ingredient in the success of any startup – whether an investment in innovation or a venture-backed company.

We have found there are two primary factors that lead to entrepreneurial spirit styming at large businesses: structural and philosophical. To increase the odds of success, companies should encourage entrepreneurial spirit among their employees. We recommend three strategies below.

 

WHAT MAKES A PERSON ENTREPRENEURIAL

Before a large company can implement a successful innovation program, they must first be capable of fostering the core qualities of an entrepreneur among their employees. Intra-company innovation is built upon the foundation of these five entrepreneurial characteristics:

  • Achievement Striving
    • This quality is the cornerstone upon which all other entrepreneurial traits rely. It is innate motivation: the imperative to move forward and to succeed. Without this quality, one cannot hope to innovate, as there is no desire to improve.
  • Industriousness
    • Industriousness is characterized by persistence and hardiness, the ability and DESIRE to overcome obstacles. Industriousness informs both the problem-solving AND problem-FINDING skills that characterize entrepreneurs – their ability to isolate unresolved (and even unidentified) issues, and generate solutions.
  • Passion
    • Passion is the lifeblood of every entrepreneur, it is the fuel on which they run. Innovation requires a profound understanding of any given field and an understanding born from a PERSONAL COMMITMENT to the project.
  • Taking Control
    • Those with a higher degree of perceived control over any endeavor will invariably operate with a greater sense of personal investment. While having a sense of ownership over one’s work is crucial for PASSION, it also generates a sense of ACCOUNTABILITY, making one more likely to charge into a problem head on.
  • Creativity
    • This is the quality that enables entrepreneurs to generate solutions that break the mold. Whether it be within the established practices of a single company or the zeitgeist of the industry at large, creativity allows one to shatter the established modes of thinking and truly innovate.

These defining characteristics of entrepreneurship can be found and/or cultivated within ANY employee.
However, within large companies, the infrastructure that has enabled their success has over many years grown inflexible. Certain structural and philosophical qualities have taken root and calcified, which can constrain (and even discourage) the ability for a company to innovate from within.

 

THE STRUCTURAL

Every business is outfitted with an array of standard practices and procedures, designed to streamline workflow, and ensure the scalability of the company. Unfortunately, all too often, these can become unnavigable bureaucratic systems, obstacles which all but destroy the desire and the ability to innovate among the company’s employees.

Of course, such structures are necessary for the growth of the company. They ensure rational practices, and protect the company from taking unnecessary risks.

Innovation, however, is about taking manageable risks to pursue crazy ideas. Some of the biggest success stories in the startup world involve “terrible” ideas that were given room to grow (think Twitter or Airbnb). This risk aversion manifests itself among a company’s employees as an utterly crippling blow to achievement striving and industriousness.

There can be no motivation to improve or innovate if any new idea is met by immediate disapproval from a risk-averse CFO. Why bother thinking outside the box if the box is the only place management feels safe?

THE PHILOSOPHICAL

Another major factor that hampers a company’s ability to innovate can be traced to the difference in the philosophical anchors of startups and those of major corporations.

Established companies tend to adhere to a “failure is not an option” approach to business, which in turn, encourages hiring outside the company when it comes to innovation. Management will typically turn to established platforms and practices to mitigate any kind of risk, opting for the safer option and all but destroying the chance to come up with something game changing.

By contrast, startups typically embrace the possibility of failure from the outset. As a rule, they are more experimental. Pioneers.

As such, they are far less likely to enlist the help of outsiders when they encounter obstacles. After all, who can possibly better understand what they are trying to do than themselves?

Instead, startups tend to source solutions from within, drawing ideas from the people with firsthand knowledge of the nuanced problems with which they are faced. This in turn, fosters a sense of personal stake in the venture, thereby increasing their PASSION for the project exponentially. If a member of the team feels they are keepers of crucial input – that they alone can solve the problem – they are much more likely to throw themselves into the challenge of generating a solution.

 

STRATEGIES

How do you encourage thinking outside the box combined with some risk-seeking behavior?  The solution is not to do away with standard operating procedure, nor is it to force CFOs to sign off on risky ventures simply to inspire employees to come up with crazy ideas.

Rather, companies looking to innovate need to package innovation as something palatable to management, something that fits within and ultimately enhances the structures upon which the company has been built.

Innovation watchdogs

One such system involves establishing a watchdog department/committee dedicated to monitoring the pulse of the marketplace. Their sole purpose is to identify new trends, keeping up to date on new and emerging technology and remaining watchful of adjacent industries for signs of potential disruption within their own.

Not only will this generate new ideas, products, projects, etc., but each innovation will be backed up by hordes of real world data, data with the power to put any risk-averse CFO at ease, comforted by the knowledge that their team’s findings have already been corroborated in the real world.

MVPs

Another way to mitigate risk without hampering innovation is the practice of generating minimum viable products. Whenever a new idea (perhaps generated by the aforementioned watchdog committee) is brought to the table, a group is put to the task of creating a prototype. Over the course of 6-8 months, this group will create a proof of concept capable of being tested in the real world.

In the event that it fails miserably, the project can be scrapped without having invested a substantial set of time and resources, while the work done is always preserved and usable in future endeavors

Minimum Viable Products simultaneously test drive products/ideas (making the CFO happy by mitigating risk) and foster a sense of purpose among employees, encouraging innovation by showing that ideas have a chance to be actualized.

Workshops

By sourcing solutions from within, startups foster a sense of personal stake in the venture and increase employees passion for the project exponentially.

Larger companies can easily take a cue from this practice. Hosting intra-company workshops designed to source solutions from their employee-base fosters a sense of inclusion and innovation.

These workshops motivate employees to contribute to solving the large company’s problems. Encouraging a personal stake in the project will enhance their passion, leading to increased personal investment, and – as we have found – many more solutions.

 

Entrepreneurship is not limited to being the founder of a startup or stand-alone business, but a set of capabilities that can be developed by anyone. An entrepreneurial culture will allow you or your team to identify problems, rethink them, and then build scalable and sustainable ways to solve them.  People with these talents are everywhere. Don’t miss the opportunity to identify and foster their growth within your organization.


Why Are Innovation Blog Posts So Boring?

Posts on Innovation Have Become Simple Entertainment. Not Actionable Specifics. Let’s Change It in 2017

Is innovation, broadly speaking as a topic matter, seen through a 21st century journalistic lens hampering real takeaways and insights? We live in a post Lewis DVorkin world, where editors at trendsetting online business publications have become so general (meaning catering to the absolute largest audience) they no longer do any sort of business leader any good.

DVorkin, for those that don’t know, kickstarter the model for incentive-based, entrepreneurial journalism. He doubled Forbes’ online audience in a very short time with the model and now Forbes has 380M unique visits a month…which is causing everyone else in business journalism to repeat the process.

It’s funny because on the opposite side of the spectrum, I think true entrepreneurs in Silicon Valley are reading trades now, and not general business magazines. Look at what Jessica Lessin has done with The Information as an example of what specificity can do.

So maybe all of us who write these blog post should try to repair what’s broken. Remember that we should serve the reader. When we build products at Prehype or Bark Box, we try to by solely user-centric. We want to offer solutions that lend to effortless buying. However, when it comes to this secondary journalism layer in the post-DVorkin world, what we are doing is essentially saying “Here are some broad concepts that helped get me to where I am…now you spend the mental energy applying them to your particular field.”

So lets start to write more specifically. I should focus for example, on how to grow/succeed in CPG good for example based on real stories from BarkBox. Stop trying to dress the same point up as something that sounds a little bit new.

There is a brilliant documentary 6 Days to Air on how the South Park creators continually turn around fresh content. One of my favorite takeaways was that Trey and Matt try to iterate a joke as quickly as they can because they feel it loses punch the more you intellectualize it. Thomas Wedell-Wedellsborg, a friend of mine who lectures at business schools told me that after I mention a new insight to him, I spent so much time turning it into a blog post, it becomes boring. So I’m trying a new format. I am pitching blog posts to fellow entrepreneurs and recording our short conversation. Then I get people who are quicker/better than I am to write the draft based on those — so I can post quickly. So what you will get here from now on are raw unpolished thoughts and specific suggestions. Let me know how you think it works?


What Chatbots Can Learn from Pickup Artists

Social engineering in the age of conversational UI can learn from Neil Strauss’ “The Game”

I believe messaging platforms are the new dashboard (or desktop) for people.

Wired’s Chris Anderson famously wrote in 2010 that apps were already changing the way we utilize the web. We went from desktop computers to cell phones with apps quickly, but now something like 70% of people use Facebook Messenger every day, so the next frontier for brands and startups to conquer is messaging platforms. Startups (like BarkBox), content providers and services are launching conversational initiatives where they send content to people exclusively on these platforms with great success. At BarkBoxwe rely heavily on this and interact with roughly 25% of our customers every month via SMS, messenger or chat. In this way we drive engagement with our customers, increase sales, product develop and provide service.

What we are discovering is that there is not a lot of advanced UX thinking or interface terminology at all with regards to conversational UI. It’s very two dimensional as far as how it was built, leading to very basic interaction models between users and customer service or bots. You ask a question. You get an answer back. How can we make that experience better and create a rapport…build in less friction and more empathy with conversational UI? We would like to turn it into an experience. It’s a bit of a curve ball, but I think we can learn a lot from pickup artists.

Back before I was married, I read that book “The Game” by Neil Strauss. It was written in 2005 and caused a fair bit of controversy. Neil was a Rolling Stone reporter who immersed himself in an entire world of pickup art. He went from being a nerdy writer, to become someone who used social engineering to befriend and successfully flirt with women. Some of the techniques are are morally questionable, however, they did highlight a systematic approach to arhiteting conversations with people you don’t know. Here are a few interesting things that pickup artists do that conversational UI designers can learn from:

  1. The opener After walking into a group of strangers, pickup artists immediately find something interesting enough to most of them to start a dialogue. They are programmed with ‘openers’. Takeaway: AI bots don’t have an icebreaker. No emotional way of engaging in the early part of the conversation.
  2. The Hook I think part of the reason for the title of Strauss’ book is that pickup artists have identified routines. A routine in this instance is a script for how to deal with specific situation and deploy empathy to create rapport. For a pickup artist, it may be as simple as changing focus on the conversation from a female target, to their male colleagues — or initiating a more interesting conversation rather than just offering a drink. Takeaway: In a conversational UI, if a user is changing a password, you can create better experience by creating a narrative (beginning, middle, end) and if our chatbot knows this, it can inject some scripted humor in the middle. “Good things dogs don’t write the passwords, since computer keyboards never respond well to paws!”
  3. The Exhange The Exchange is simultaneous focus on different outcomes. A pickup artist knows about different outcomes (and more importantly, is willing to accept them) before they ask for a number or a date. Leaving someone after you have engaged them in an emotional way is usually the best way to get them to come back. Takeaway: The bot should know “Hey it seems like you’re not really sure about this purchase yet, is it cool if I contact you again in two or three weeks?”
  4. The Context Pickup artists have learned a trick where a target will respond favorably if they think they already have a shared history and narrative. Meaning, they will try to move locales if they already initiated a conversation at a first bar or club. Takeway: We need to get the know the users — even if they engage with us on various platforms. If a user comment on your Instagram — you should know that when chatting with the user later on twitter.

In summary, remember the following things when working in conversational UI:

What is an engaging way to start a conversation? What is your icebreaker? This will be different depending on industry. A conversation initiated to reset a password is a lot different from one where a dog owner is trying to get ideas about gifts for their dog’s personality.

Remember an chatbot needs a narrative. Beginning, middle, and end. We are looking into different routines that can be reused — depending on scenario and user. This is The Game. The more routines we process, the better we become at finding what works in different scenarios and how to become more engaging. We’d also hope to be able to identify early if the human on the other end is short for time, and not looking for humor. Like code modules, our bots or service staff can become better if we test and improve on our routines for different user types. We also know from studying routines things like it’s best to offer a discount or sale at the beginning of a conversation. We’ve found that if you inject an offer toward the end, the customer feels like it discredits the entire exchange.

A pickup artist’s favorite way to end a conversation is what they call “The Close.” There is the phone number close, and the kiss. BUT, there are objectives along the way that can be met, such as an informal agreement to going out on another date. In the same way pickup artists utilize what I’m calling above “The Give”, a chatbot needs to have multiple outcomes that are acceptable, not just going straight for a sale.

Finally, we need to utilize social engineering tools to create rapport but with respect for the user. Referencing memory points in the past will create a stronger bond in the present. There are many tools to create a better experience for the user, but at the end of the day we need to keep in mind that we are serving them. Conversational UI can be amazing to create entertaining and engaging dialog with users and by being more analytical about our approach to this relationship we can create amazing experiences. However, as with any relationship, we should be mindful that that morality needs to play an essential part for checks and balances. You don’t want to sell someone a product that they don’t need or be that annoying person who text way too many time…


3 ways companies can innovate the way they do innovation

Innovation has become the workout regimen of the business world. Everyone claims they do it — or likes to believe they do it — but at the end of the day, very few are actually seeing results. It’s not the innovation or the exercise itself that’s failing to deliver; it’s the approach.

Just like running 10 miles a day won’t land you the perfect body, creating an innovation team and setting it free won’t translate to industry-changing products. The people in these teams are most often previous employees who think like a big company, not an innovative and fast-moving startup. Therefore, their innovations are costly, rule-abiding, and deliver meager results.

With BarkBox, we didn’t start out as a massive organization. We were once a small company focusing on what we thought was a small idea; mailing monthly boxes. But over time, that small idea — backed by traction — transformed into a large-scale entertainment / product business. We were open to small changes, but never prohibited starting something that could move us closer to our goal of becoming the Disney for dogs.

By avoiding pain (risk) and neglecting the stairs (early traction), many companies and exercisers alike end up sitting around waiting for the results to show up on their own.

Why Companies Prefer the Status Quo

It’s not that these larger companies don’t want to create meaningful innovation — they absolutely do. But their existing habits, much like eating poorly or skipping leg day, make it nearly impossible to create impactful results.

The first bad habit is spending patterns. Entrepreneurs normally lack the funds to go big on the first try, so they develop lean methods to test and prove their assumptions. Big companies, on the other hand, have processes in place that make testing of new ideas expensive — think millions of dollars down the drain. They have the money, so they spend the money.

Which leads to the second bad habit. Because of the large investment, the project creates a “failure is not an option” mentality. They’ve already invested millions, so they can’t stop now, right? Unfortunately, that’s the wrong perspective.

Entrepreneurs, with their limited capital, have the freedom to stop a project the minute it fails to move the needle. Essentially, entrepreneurs are a bit more rebellious in the early days, but more rational after three to six months in, whereas big companies, who are a little bit too rational in the outset, develop irrational behaviors once the project hits maturity.

Leading the Company to Innovation Fitness

If you’re a boss who doesn’t think innovation comes from the top, then innovation won’t come easily. Many CEOs focus so intensely on moving the needle bit by bit, they overlook the need to innovate, leaving the innovators without the funds and direction they need to make meaningful changes.

However, a true innovator won’t allow organizational obstacles to stand in their way. If no one is listening, hack the bureaucracy silences you. If no one likes your idea, show a proof of concept to change their minds.

When I was a producer at MTV, I had an idea I was super passionate about, and took it to my boss for feedback. He didn’t care for it, but I didn’t let that to stop me. I bought the equipment with my own funds and ran a test. My boss couldn’t fight me on viability when he had the data right in front of him.

It sounds uncomfortable at first — as does running wind-sprints — but investing your evening, weekends, and a bit of your own money will make your team feel more comfortable spending millions.

Don’t wallow in self-pity because no one believe in your idea; place bets and show everyone when you take home the chips.

How Overweight Companies Can Innovate Correctly

Leaders of large corporations are faced with an immense challenge. How can they make their employees think like entrepreneurs? How can they encourage risk without wasting millions? If you aren’t sure how to answer those questions, the following tips are for you:

1. Take some ‘before’ photos.

The first thing every company should do is to look at what has been done and whether or not it’s been working. If it’s working, do more of that. If it’s not, consider moving the funds and employees to a more valuable project. Innovating just for the sake of innovating won’t move you closer to the next big idea if you’re chasing down multiple dead-end paths.

2. Find the best workout buddies.

Spend time reflecting on how you attract entrepreneurial talent. Have you created an environment that would attract people who have a growth mindset? Have you thought about how you could attract those people? And when you find and attract these entrepreneurs, are you evaluating their potential fit?

Risky

and far-fetched entrepreneurs may not be a great fit for a more traditional company, so get to know innovation candidates before snatching them up. They won’t be happy with your structure, and you won’t be happy with their reckless abandon.

3. Celebrate small gains.

Innovating doesn’t have to mean betting the house. Implementing innovative innovation means creating an expectation of small and calculated bets. New ideas should be partnered with a testing strategy and a modest budget. That way, when the testing proves the value, your company can go all-in without fear of going broke.

It sounds redundant to innovate your innovation, but the proof is in the low-fat pudding. Approaching your methodology with open eyes will lead to better results and bigger ideas. So stop sitting on the couch, hoping you’ll land your dream product — get out there and chase it down.


Reducing the Risk of Innovation

Sometimes, the biggest obstacle to innovation isn’t too few resources — it’s too many.

When attempting to explore new directions, larger companies often find themselves struggling to accomplish what companies with just a fraction of the resources achieve. It’s one thing for workers at a large company to think “agile” but quite another to actually innovate.

Even worse, many employees tasked with innovative projects are hesitant to stray too far from the box. After all, few people are rewarded when risky ventures fail.

While no one can eliminate all risk in any business venture, there are a few ways companies can approach innovative thinking that will reduce the risk of trying new things and increase their chances of success.

The Wrong Way to Do It

Organizations love to focus on new ideas that can “move the needle.” If projects don’t sound like $100 million ideas, they often don’t attract internal enthusiasm and buy-in.

Consequently, many ideas get bundled into “portal” formats — situations in which companies absorb exorbitant resources in the planning stages, envision a massive scope for a project, and allocate large budgets to pay for development. Companies often spend 18-24 months on a single project, only to see it fail when finally put in front of actual users. By the time the project is half-redone and ready for relaunch, enthusiasm has waned, and the world has moved on.

The difference between big companies and small ones is simple: Many of the operational processes inherent in large businesses naturally lead to high test costs and elongated development cycles. Their payment policies and procurement systems, for example, are designed for working with other large companies — not agile freelancers and small vendors.

These factors make building a good product quickly and cheaply almost impossible without the proper mindset.

Lowering Risk and Improving Results

Small companies have flexibility and experience interacting with startup resources. As an alternative to the “big company” methods that cost more and accomplish less, we recommend identifying a problem and focusing on finding the quickest way to test a solution to that problem with real customers. If an idea fails to gain traction, let it go; if it succeeds, double down and move forward.

Here are a few more tips to help you think like a startup in a big business:

1. Go through different channels. Think about what new structures would allow you to work with external partners the way startups do. Whether that means partnering with an intermediary or getting creative with payment terms and standard policies, you must be flexible if you want to work with (and emulate) smaller, more flexible companies.

2. Make the start the easy part. Focus on ideas that have an easy start and a big finish. Big companies like to plan out entire projects from beginning to end, but innovation requires more fluidity. Put the bulk of your energy into projects that can get quick traction, and build from there.

3. Avoid tunnel vision. Look at your industry holistically. Innovation isn’t just about making your existing business operations better; it’s about identifying tangential opportunities you might not have considered otherwise. If an unsolved problem makes itself apparent during your process, see whether you can find an answer for it.

4. Facilitate entrepreneurial talent. Why not work with the people who do this every day? Seek out venture partnerships by setting up new companies that can work with more flexible rules than your parent company.

Innovation is never risk-free. That doesn’t mean you have to throw money away every time you want to try something new. Follow these tips to think more like an entrepreneur, and watch as your company begins to solve more problems more quickly


A style of entrepreneurship that Silicon Valley overlooks — but you shouldn't

When you read about entrepreneurship, you can get the sense that there is only one type of company. Invent some new technology, get hundred million users and IPO. The theme was echoed by the always thought-provoking Steven Black in his fireside chat on Startup Hacking. (link). During the presentation he caveats his point by outlining four types of entrepreneurs and suggest that there are other kinds of entrepreneurship that might be different from a classic Silicon Valley Startup;

– Lifestyle entrepreneurs, like a surfer that take a few students to help her finance her passion.
– Mum & Pop entrepreneurs, like corner shops and small family businesses
– Tech entrepreneurs, like the founders of Facebook and Google
– Feature entrepreneurs, people who make features or technology that then get bought by bigger tech companies.

I find it to be a refreshing thought that there are different types of entrepreneurship and that founders should build the kind of company that fit their temperament, skills and region. Especially because, I as a non-Silicon Valley founder, often find the advice and methodology provided by many in the startup community to be very specific for the type of tech startups that Silicon Valley create so well. What seem to be especially lacking (and sometimes even looked down upon) is what we can call the ‘Old School Startup’. New companies that are not enablers of new technology but powered by it. Startups that might not create a whole new behavior or industry but are replacing or expanding an existing one. Companies like Warby Parker, Vice Media and JustEat. I realize that for a VC, a perfect home run is a new tech startup where the returns are incredible. However, I suggest that there is a host of big innovative startups that are being built that use a different methodology than what is best practice in Silicon Valley. Theses companies might never become as valuable as Uber, Google or Facebook — but they, not small Mum & Pop shows either. A few properties that make them different;

– The are powered by technology not an enabler of a new one
– They are most often disrupting an existing industry that have been dormant or not innovated in their product, business model or service layer
– The founders are often not engineers
– They often have a business model in place from day one and can scale their business while they expand their user base (vs. focusing on getting a big user base and then figuring out the business model)
– They are often made by creating fresh brands — and using web tools to make products/services/experiences better and cheaper.

There are several other types of entrepreneurship (agencies and service startups comes to mind), but in our fascination of companies like Facebook that grow from nothing to 100B in a few years, we seem to be forgetting that the world is filled with these other amazing companies. Now the world is not binary, and there are certainly startups that are a hybrid between ‘Old School Startups’ and Tech Startups. (e.g. Uber), but as we talk about startups in general, we should become more aware that there are different types — and methods that work for growing one type — might not work for others.


I asked founders on mobile trends for 2016 — here are the six highlights…

Everyone has heard “desktop is dead” and “mobile is eating the world” a million times, but what does that actually mean? And, more specifically, what does it mean for you?

For starters, it means that 900 million people — almost 1 in 7 people on the PLANET — use Facebook on their phone every day. It means that over 3 billion videos are viewed on Snapchat, and 5 billion more on Youtube, every single day. And I don’t think I’d be far off in saying that you probably check your phone well over 100 times a day. In fact, I’d be surprised if you weren’t reading THIS on your phone.

So, what “desktop is dead” means is that mobile should not be part of your strategy. Mobile should BE your strategy. Whether you’re B2C or B2B, being customer-centric means living, working, and breathing mobile. Below is a handful of short, to-the-point, and directly actionable insights on mobile based on trends the team here sees that you should be thinking about as you head into 2016:

1. Video: vertical and… soundless?

Have you ever held your phone horizontally to type a text? Do you check your news apps or Facebook in horizontal mode? Thought not. But you probably engage in the all-too-familiar video-watching battle every day… You hit play on a video in your feed, and it starts to roll, but it looks small and distorted, so you turn your phone to the side, which makes the video pause or skip, so you have to rewind or flip the phone back to vertical… meanwhile, you’re frantically hitting the “volume up” button with one hand whilst trying to disentangle your earbuds with the other…

All of which is to say, we all need to rethink how video is made for mobile. Video viewing on Instagram is square, but we’re seeing more and more vertically rectangular video across content platforms. And a muted auto-start — which Facebook does — will have people deciding if they want to watch the video without the audio playing. So video content needs to capture your audience without audio and should probably be made in the way people use their phones: vertically.

2. App-less apps.

Texting is the native mobile interface. It’s universally easy, natural, and quick. In the past year, we’ve seen an influx of apps capitalizing on this interaction framework — apps that aren’t really apps at all, but deliver a service or a product via the text interface. These “hidden” apps — like Alfred and Magic — have tended to deliver luxury experiences, but we predict that hidden apps will start to cross over into middle-market products and services. Listen to more thoughts on chat-based interfaces here, on the Prehype podcast.

3. Platform agnostic content marketing

Yes, Facebook has 1.5 billion users, and you should be optimizing your content for Facebook. But Instagram has 300 millions users, Snapchat has 200 million users, Pinterest has 100 million users, and Reddit has 40 million users. Medium now has nearly 1 million. Outside of Facebook, where does your audience lie, and how can you optimize your content marketing strategy to span these platforms? At BarkBox, we’ve built an influencer community that spans all of these networks, and we run campaigns and contests that work fluently across the board. Think less about your content as a destination — and more as bite-sized part of the wider web.

4. Hey… you still reading this?

Okay, so maybe (hopefully) you are, but there’s a good chance you’ve clicked away or switched back and forth through other apps over the course of reading this. This is because mobile consumption is distracted consumption. Say goodbye to the traditional story arc of beginning, middle, end — content needs to be continuously engaging. Stories should be made up of smaller sound bites, and the format in which you publish your stories (text, video, audio) needs reflect that.

5. Your customers are on their phones — why isn’t your team?

Customers browse your products on their phones. They read your content on their phones. They chat with your customer service team on their phones. They make recommendations to friends about your products on their phones. If they are waiting for their car to get fixed, their doctor to see them, or for a friend at the bar — they are on their phones. However, I bet that all the presentations you see at work are on a computer, from the screenshots of your new website to the email campaign. Start making the mobile change today by demanding that products are presented in meetings in the same way that your customers see them — on mobile. A mobile future calls for a mobile now, in all aspects of business-as-usual.

6. The landing page is dying.

The traditional path for app discovery is getting turned on its head. We tend to think that people download apps because they see an ad, click through to a landing page and learn about the app, decide they like it, and then go to the app store. But this model is changing. What we see is, instead of turning to landing pages for information, people jump from the ad straight to the app store to download and test out the app. This means that the real discovery process takes place within the app, through users actually interacting with it, not on a site dedicated to explaining what it could do for them. The problem is, most app UXes don’t account for these totally unindoctrinated users. In lieu of landing pages for apps, apps themselves must offer introductory experiences, which also means apps must be optimized for conversion.

… Thoughts? Questions? Just want to say hi? Would love to hear from you.

PS. If you’re curious about what we have been up to lately at Prehype… here’s a few things that kept us busy this year…

Prehype partners continue to launch great homegrown startups … AndCo and Amberjack have launched in 2015.

In 2015 to date, we have co-created around 6 ventures with corporate partners like LEO Pharma, Dow Jones, and RBS, with more to come.

We have moved into secondhome for our London office, it has plants, entrepreneurs and other startups. Come by.

Ahh, and another shameless plug; we’ve launched Prehype’s podcast earlier this year, where we discuss everything from health tech to social engineering and architecture. Would love to hear what you think about it, and would always appreciate any topic suggestions.


The future of mobile interfaces and the rise of chat based apps

The future of mobile interfaces and the rise of chat based apps

The other week I was lucky enough to have Aaron Harris, partner at Y Combinator, take time away from reading applications to have a chat about… mobile stuff. Our conversation turned into an enlightening exploration of what is now not so much a trend but the way the world is (mobile-first), what’s coming next in mobile, and how he personally deals with the fact that, yes, mobile is eating the world.d.”

It’s safe to say we’re undergoing an overwhelmingly rapid transition to a mobile-first world. Mobile-first evangelists (myself included) tout the imperative of making mobile not part of your strategy but the foundation of everything you do. In the mobile-first onslaught, however, sometimes we risk losing sight of the fundamental objective: to solve a problem.

Talking with Harris served as a useful reminder to this obvious point, which nonetheless sometimes get buried. “Ultimately a computing platform is being built and that software has to be accessible wherever your users happen to be and in whatever mode they want to interact,” said Aaron. “The goal of creating software that solves a problem must remain on the forefront.”

Of course, that said, more and more, those interactions are happening on mobile devices; in five or ten years, I would be surprised if 99% of digital interactions happen on mobile. As we chatted more about this, a few themes popped up around what Harris sees as the next big shifts in mobile.

One was increasing simplicity — in terms of function and design. The great thing about phones is that real estate is small, naturally forcing simplicity upon app developers. Or so you would think — too often, users face an unintuitive jumble of buttons, interfaces, and controls. The best apps those with clear applications and clear UIs. Uber, vaunted prince of Silicon Valley, is a simple app. It’s function is simple — get a car to drive you from point A to point B — and users can achieve that goal in maybe three actions, if that.

But simplicity, Harris acknowledged, goes well beyond clear use cases and good design. One of the next mobile progressions he’s most excited about actually, is preemptive applications — apps that remove all friction points but not requiring anything of the user at all. Instead of even having to open the Uber app when you land at the airport or walk out of the subway station, your phone will have already figured out that you need a car and will have ordered it for you. There’s a lot of work being done on preemptive applications right now, but there’s a long way to go. Harris mentioned being particularly excited about what Google Now on Android has cooking..

After dissecting the mobile world for an hour, Harris brought up a curveball — something I did not expect from someone who is so utterly immersed in tech. Harris, it turns out, observes a technology Sabbath.. That’s right — no phone, no email, no Snapping selfies — every single Saturday. “It’s these 24 hours a week where I don’t have a computer, I don’t have a phone, I don’t have any of that stuff. I actually have to think.” Finding moments, let alone hours, that are truly unplugged is becoming increasingly difficult, yet, (remarkably given the demands on him) Aaron has found ways to give his brain room to breathe. Aside from the Sabbath, he recently started to only answer email for an hour in the morning. Periodically, throughout the day, he will check to see if there are any emergencies, but he has broken the habit of constantly monitoring his inbox.

Quite a feat — one we should all probably take inspiration from. Read on for more insights from this enlightened individual below, or scroll further for the full transcript.

You can also listen to the podcast on SoundCloud and subscribe on iTunes.

On the need to constrain problems:

“Constraints on a problem are some of the best things that you could possibly have and that applies to thinking about a new business or thinking about a new startup or tackling a new problem. Actually, constraining that problem is critical to creating something that’s useful. Otherwise, you just end up with hodgepodge.”

On the progression of technology:

“And then — it got personalized. You had to give the computer less and less information at any given time to accomplish the end goal. And when you jump towards things, if you follow that progression forward, you get to this idea that people really want technology to do something for them, right? And really interface is, in some ways, a barrier to that.”

On his hopes for Microsoft and healthy competition:

“…maybe Microsoft becomes the next integrated hardware/software maker, for the PC side. I can see it happening. Microsoft spends more on R&D than any other company or something like that. And there are still brilliant people there and they are capable of doing really incredible things. And I don’t know that necessarily, by the way, that Microsoft is making the best stuff or will, but I think competition on this is great.”

Transcript of podcast here:

A: Hi, my name is Aaron Harris. I’m a partner at Y Combinator where we work with lots of startups and I’m a longtime fan of Henrik Werdelin, one of my personal role models both in terms of hair styling and thinking.

H: I’m actually a pretty big fan of yours

A: Well, thank you.

H: So now this is awkward.

A: This is really awkward.

H: Aaron, tell me a little bit…what does a partner at Y Combinator do?

A: We’re basically responsible for finding new startups for YC to work with and invest in, whether that means going out and recruiting companies by meeting with great people wherever they are and talking to them, or sorting through the applications that we get twice a year for YC itself.

And then once we’ve actually selected those companies, we work with them for the three months that they’re actually in California with us. We spend quite a bit of time with them then, but also for the lifetime of the company — and even beyond. We help founders try to build great businesses and help in any way that we can.

H: We can honestly talk about many things, because you know about a lot of different stuff when it comes to startups and building different companies.

The thing that I was hoping to talk about today was I would say a little bit of a paradigm change in mobile occasions and how the interface of mobile and the avocations of it being done. I think it’s being referred to as hidden interfaces.

I think for people who are tuning into this podcast that would probably be most of the stuff that we’ll be talking about. Is there anything else that you feel we all need to know about?

A: You know, we might happen across some things at some point, but that’s the topic that you and I have talked about a little bit already. And I actually think the scale at which mobile devices have penetrated our lives is really, really interesting and so much larger than anyone anticipated.

And the platform itself is so new that I don’t think we’ve really hit what the right paradigm is for how we interact with computers in our pockets that are always on and always know where we are.

So, you know, there’s massive businesses yet to be built and that’s going to take a lot of iteration and a lot of different attempts at how those actually work.

H: I was sitting at a board presentation of a large PG company a few weeks back and I think it dawned on them — and actually it hadn’t even really dawned on me before then — how incredible this mobile movement really has become.

We’ve all been talking about it for a while…mobile is coming, mobile is coming, but where I am in my mind now is pretty much — there are no desktops.

Like even talking about mobile first is almost too dated because you should really just be thinking about mobile. Then, later you might be able to do a desktop application. Do you think that’s a fair assessment or is that just too extreme and dramatic?

A: You know, I think it’s a little too extreme because it depends on what kind of business you’re building. If you’re building something targeted towards consumers, then for a large, large portion of the companies I think that’s right. Though, what I would say is that mobile first feels a little dated, but I don’t think that it’s mobile not desktop.

It’s just the idea that you’re building for computing platforms, right? You’re building software and that software has to be accessible wherever your users happen to be and in whatever mode they want to interact. So that’s how you have to think about it.

H: In many ways building for a platform first is the wrong way of trying to solve a problem, right? Often you should identify a problem that you want to solve that customers at large have. Then, you should use technology to solve that problem and because people are spending a lot of time with their mobile, then, by design, it will probably be a mobile-first application.

But, it doesn’t have to be a mobile application: it has to be an application that solves a problem and then it has to be mobile.

A: Right, that’s exactly right.

H: The nice thing that we’ve noticed as we try to build these is that real estate in mobile applications is so limited and so everybody is trying to create minimum viable products. That term is starting to be used in a lot of different contexts.

And even if people try to make something that’s a minimum viable product, they still make the scope of what they’re trying to test very large.

So one of the things I like about mobile is that simply by there not being a lot of real estate it kind of gives you some limitations of how much you can shove into the stream. That actually forces you to be a little more specific about what you’re trying to achieve.

A: I think that’s totally right. Constraints on a problem are some of the best things that you could possibly have and that applies to thinking about a new business or thinking about a new startup or tackling a new problem.

Actually, constraining that problem is critical to creating something that’s useful. Otherwise, you just end up with hodgepodge.

And I think that extends to what you’re talking about which is: if you’re using a mobile device are you building for a mobile device?

When you say real estate, you’re talking about screen real estate, right? You can only show someone so much at any given time, which sort of drives you toward absolute simplicity or the least amount of interaction from the user required to accomplish a given purpose.

H: Over the last six to 12 months, I’ve definitely noticed an increase in the consigner’s apps. They are the text-only hidden apps or whatever you want to call them, that don’t really have a lot of functionality in the interface layout of the mobile itself. It has functionality in the back end and that’s exposed to the user by a kind of normal chat module.

First, do you think that’s true? And second, if it is true, why do you think that it’s happening?

A: I’ve definitely noticed the same thing and I’ve found it pretty fascinating because for a while everyone was talking about how important beautiful design was, right? Beautiful design is the differentiator, if your app is pretty and feels great, that’s the differentiator.

But if you look back at the progression of technology in terms of how we use things, each piece of technology is essentially trying to accomplish a given purpose, right? And the UI and the UX are really just ways to accomplish that goal.

And so, going back a few years, if you wanted to do X on a desktop, well the way things work, because the computer didn’t know very much about you and didn’t remember things you had to trigger each set of filters, categories and options every time you used it. And then, over time, that went away because computers can now remember the state from last time, remember who you are.

And then — it got personalized. You had to give the computer less and less information at any given time to accomplish the end goal. And when you jump towards things, if you follow that progression forward, you get to this idea that people really want technology to do something for them, right? And really interface is, in some ways, a barrier to that.

That’s kind of a weird way to think about things. Even the most beautiful interface is a barrier to accomplishing a goal when it comes to consumer services.

If you could eliminate that and basically just say to your phone: “Hey, do this thing for me.” And, you knew that it would come back with the right answer or the right solution, that’s kind of the ultimate in technology, right? That’s perfect. It does the thing that you want it to do without you having to do very much.

H: So there could be different thesis of why this is happening now, right? One thesis could be people are pretty used to complicated actions that a computer could do for it. But, the mobile screen real estate doesn’t really allow you to do that very well.

Therefore, you need to find an interface form that users understand, but that still allow the users to get a lot of complexity with very few clicks.

Now on the mobile phone, you can’t have 8000 different dropdowns and other tools that we’ve previously done on desktops and so the easiest form that people kind of understand is kind of like a chat system. Do you think that is a driver?

A: Yeah, I definitely think that plays a role. Do you know what an interesting interim sort of step is in this progression is if you look at…let’s take Uber right? It’s an app everyone kind of knows about, everyone appreciates…well maybe not everyone. I think a lot of taxi drivers hate it, but it works incredibly well. And it does one thing right? It sends a car to wherever you are. And as a user the only piece of that I really interact with is I pull it up, I open it up, it GEO locates me and I push, pick me up or whatever it is.

It’s one button. It’s one click. I mean, okay, now over the years you can select UberX, UberXL, this, that, the other thing. But, fundamentally it’s one button and if you thought about that from the previous paragon, it would seem crazy. That’s all you have to do. It’s filling in all the other information by itself.

And if you think about it, okay that’s one step, what if I could just come out of the subway, right? Or you know, land at the airport and my phone already knew that I want a car? And so the car would show up.

H: We’ve talked about that, even when Quantified Self was the talk of the town, everybody was measuring everything, but the computers couldn’t really even use the data for much other than the pretty graphs, right?

Like it wasn’t that suddenly it was coming with different types of running techniques. We didn’t use the data for anything meaningful to change our behavior or make our lives better. We just gathered and displayed it.

Do you see any examples of what you’re talking about? This kind of preemptive behavior functionality where the computer makes your life easier by knowing what you’re about to do and then suggest that you do it for it? Foursquare talked about it at one point a long time ago, but have you seen anything?

A: You know, I haven’t really seen anything that has done it well. There are glimpses of it when you use Google Now on an Android phone, right? It’ll tell you: “Hey, you have to leave now in order to get to that meeting by this time given traffic.” That’s pretty amazing.

But, I don’t think anyone has really accomplished that yet. But, I think that there is this idea of a text-only interface or even…kind of a Siri thing. Siri is just a bad way to input instructions because it doesn’t work very well, but text, you know?

It’s basically saying: “Hey do this thing for me, you already know the thing that I want, right? So now I’m just telling you to go do it.”

H: I think that’s true. I think when you search Google it probably does some of the preemptive stuff that you don’t even notice or see. I guess one of the elegant things about having a lot of intelligence in the computer is that ideally you don’t notice it if it worked.

One of the things that people have been talking about with text interfaces is this emerging of AI or neural networking or whatever the proper term is these days. Do you think that AI or neural networking applications are around the corner?

A: I don’t know, it feels like we’re getting closer in some ways, right? Our phones, our computers are definitely smarter; they’re able to do more on the predictive side.

Certain implementations of artificial intelligence and machine learning are revolutionizing the way that certain tasks are done. But it still feels like we’re quite a long time away from the robot companion or the computer companion, right?

H: You’re not going to install the Her emotional operating system anytime soon?

A: I don’t think so, but, again, this stuff is kind of hard to predict in terms of when it’s going to happen.

H: I think you’re right in the sense of some of the applications we’ve been working on. One of the things we’re launching soon is called Anco which is basically a back office for freelancers. So, it’s your emotional-rating system for doing all of the boring tasks of your freelancers.

One of the things we’ve been talking a lot about there is that because humans require so much emotional intelligence to interact with, you can actually build quite powerful super admin control panels that would allow a human to interface with quite a lot of people and scale it in that way.

So instead of going straight to AI where the computer is talking directly to the human, you are almost putting a human in the middle and then you give them a very powerful tool that allows them to talk a lot of people at the same time.

And I think that might be the in-between step, right? You have somebody, like a concierge type of functionality, where they are very good at being personable, they are very good at understanding you, and then they are very good at using tools that would be way too advanced for us to ever put on our phone.

A: I’m trying to figure out where our phones are going versus where other computing platforms are going versus where the computation takes place. It feels like it’s kind of talking about all of these things that we don’t know…it’s so hard to predict the path of technology in that way.

H: But isn’t that one of the points is that while technology is very difficult to predict, humans are like the slowest evolving point of that equation now? So one of the things that we probably need to optimize increasingly is how slow the human thinks or interfaces with computers.

And so I think we’ve probably been in a world for a few years where we kind of allow the human to adapt their behavior to optimize for ease of use from the computer’s point of view, right?

So we use a mouse because then a computer can understand that. We use a keyboard because that’s an efficient way. We use dropdowns because that’s something we can turn into a database and inquire really easily.

And I think increasingly it seems like we’re getting so fast and quick at doing stuff from the computer side, but the humans really don’t understand all these dropdowns and things. It would be neat to go a little bit back to basic where that is normal dialogue.

And especially on a platform like mobile phones where I think for the first 10 years was really used just for the chat dialogue, right? We text each other and therefore that we have like muscle memory and that kind of form of interaction.

A: One of the things that I would disagree with in what you just said is that humans are the slowest moving piece of this problem or of this challenge in a lot of different ways.

There are still these sets of problems that people are far better at solving than computers are and it’s going to take a dramatic leap in technology to actually equal how people do certain things, just based on how our brains work.

But, you know the computers are evolving probably at a faster rate than we are, so that’s right. But we’re making them evolve in a lot of ways, but they are getting faster probably at a better rate than our brains are changing.

H: I think that’s fascinating. I guess that goes into the whole singularity and what’s going to happen with that. You know, obviously computers can beat people now in a chess match, but I read somewhere that if you take a computer and a person versus a computer, then the couple of a person and a computer together will win over the computer.

A: Right.

H: So it’s obviously fascinating when you reach Chris Ward and people like that. Like how far are we from having to kind of superpower ourselves with technology tools?

I guess we do that already. We have our phones in our pockets and that’s basically extending our body with GPS and an internet connection and a camera and a few other things like that.

A: Yeah, it’s the combination of the two that’s so powerful. Then, to take it back over to the point about chat, where does chat fit into this as an interface?

And I wonder if it really has anything to do with AI or the singularity stuff. I don’t actually think that it has very much to do with that yet because it’s mostly, like the other side of these chat applications right?

It’s mostly not super complicated computer things that are happening on the other side. It’s not like you’re interacting with a complete chat machine on the other side that caters to your every whim. You’re usually giving a fairly simple set of instructions.

H: Let’s change gear a little bit on the chat interface. So one thing is obviously that you can do something fairly complicated in chat in a pretty easy way, that would require a lot of actions if you had to build interface for it.

Sometimes you could build something much easier on an interface right? Like a map or your example with Uber, that would probably take longer time to write out, like please send me a car to this and this address would take longer time than just clicking one button when you open the Uber app.

On the flip side, you see these concierge apps that are kind of trying. They are almost taking a number of different on-demand services and combining them into one, right? You take Butler or Magic or some of these other things that can text us anything.

Do you see a world where some of these on-demand apps will have less importance because these chat-based apps will almost create an abstraction layer before these underlying apps?

A: Well, I think there are two things happening there. One — I think there are simply too many automan apps which accomplish the same thing for slightly different pricing and so you have this paradox in price situation, right? Where people just don’t know which of the five different car share options they should use and they don’t know which of the four different delivery things they should use?

And two — no one wants to download all those apps and check all those things, so it’s much easier to offload that to someone else. And so you could do that in one or two different ways. You could do that by having people, by building some sort of solution that actually ties all those things together, right?

You could have some sort of magical interface that checks them all against each other. But, it’s much easier and certainly faster to say: “Hey, text us for this thing and then we’re going to do everything.”

H: Do you think that’s going to be a business model going forward? There are definitely some big players trying to become the interface to the rest of the world, just via text life, so they do everything pretty much. Do you think that’s a business? Or do you think it’s almost just a step in between and that in this on-demand era you will have to download a lot of different apps to get something else?

A: Well I think it’s a step, but I think it’s a step where if someone pulls it off right, it will actually be the next piece, right? If you have the right technology, the right set of people executing on that problem, what you end up doing is actually creating this thing that everyone kind of wants. Which is — going back to what you were saying before — not necessarily the predictive side, but I just say to my phone or tell my phone anything I want and it accomplishes it for me, right?

It’s like the computer in Star Trek, right? Anywhere on the ship, anywhere on the Enterprise you just say computer do this and it does that thing.

H: It is kind of fascinating. I just got one of those Amazon Echoes, have you tried one of those?

A: Yeah.

H: And so I bought it and I kind of hooked it up to my smarthome, so I can now go: “Alexa, turn the lights off.” And the light goes off in my living room.

It’s very powerful and it’s funny how we’re almost becoming so lazy that the alternatives are obviously either to go over and press the button or to take my phone out, open the app and then press a button and turn off multiple lights at the same time.

A: Right.

H: But, just by saving like eight seconds, which is like saying to somebody out in the living room to turn off the light, it’s actually pretty useful. I know it’s a first-world problem but it’s incredible how you can build something that is actually just a little bit better, but it just becomes a little bit magical.

A: Yeah, you know it’s incredible how important convenience can be and how important speed is and how we get conditioned to want ever-faster things. And you see this on web, right? Like Google prioritizes your website, if it’s fast. And that bar just gets higher and higher and higher.

Because it’s true, you hate watching things load, even though when you think about what’s happening, like you’re sitting on a beach with a little thing in your pocket that broadcasts a signal from your computer up into the world that gets information from the other side of the planet, that comes back to you, right?

Like it happens in the fraction of a second, when you think about that it’s crazy that you should be upset. It’s crazy that that doesn’t take hours, right?

H: Did you ever see that Louis C.K. clip where he’s being interviewed and he’s like: “it’s going to space, will you give it a second!?”

A: Yeah, it’s about being on an airplane with airplane Wi-Fi and how we’re so angry that the Wi-Fi is slow.

Conan O’Brien: In the 21st century we take technology for granted.

Louis C.K.: Well, yeah because now we live in an amazing, amazing world and it’s wasted on the crappiest generation of just spoiled idiots that don’t care because this is what people are like now.

They’re got their phone and they’re like: “Oh, it won’t…” GIVE IT A SECOND! (laughter) It’s going to space; can you give it a second to get back from space? Is the speed of light too slow for some of you?

(laughter and applause)

Louis C.K.: I was on an airplane and there was internet, high-speed internet on the airplane. That’s the newest thing that I know exists. And I’m sitting on the plane and they go open up your laptop, you can go on the internet…it’s fast and I’m watching YouTube clips…it’s amazing, I’m in an airplane. And then it breaks down, and they apologize the internet is not working. The guy next to me goes: “pssss this is bullshit”. (audience laughing) Like how quickly the world owes him something he knew existed only 10 seconds ago.

H: Another thesis that I’ve been playing around with is text-based apps. I increasingly have a lot of meetings and a lot of people, so I often don’t have an hour to research a plane ticket but I definitely have six 10-minute slots throughout the day, when I’m sitting in the taxi or whatever.

So, one of the things that I notice is that I use a lot text-based apps. For example, I’m using something called Pana for travel. I break up what would normally be a real research project into bite size projects. So you know I’ll need to go to San Francisco but I need to stop in Columbus, Ohio on the way.

Normally if I had to do it myself on my phone, it would take a bit of time, it would be a bit complicated and then something will come up or somebody will ring or the session will timeout and then I’ll have to start from scratch. So I’m using all these micro-moments in time and I’m using one of the apps to fill up that time and to be productive in that time.

Do you think that’s one of the reasons why this is working?

A: I think you’re an unusually productive person, so I don’t know that it’s fair to generalize what you do out to why things are working overall.

I do think that a lot of us feel the need to always be doing something now, which is kind of sad.

H: I was thinking the other day as I was using this mindfulness app and I was thinking of the irony of me using an app to make me just sit and think and just look into thin air. I thought “god, I should have an app, which one is the best app, I wonder where I should research which is the best app for me to sit and do nothing for 10 minutes?” Or I could just really sit and do nothing for 10 minutes and I’d be fine.

A: I mean you and I have talked about the fact of why I am so grateful that I’m Sabbath observant, right? It’s these 25 hours a week where I don’t have a computer, I don’t have a phone, I don’t have any of that stuff. I actually have to think.

H: That’s really interesting. Do you think that changes your mood or does it make you come up with better ideas? Should all non-Jews incorporate a Sabbath, a digital Sabbath into their life?

A: You know, I’ve heard people talking about the digital Sabbath stuff, where you just volunteer to put your phone down for a few hours or even a day, and I think that’s great. I think it’s awesome for people to unplug for a little bit because it’s such a constant noise.

If you’re standing in line waiting for a coffee and everyone is on their phone — and I know a lot of people have said this, there’s nothing new to this idea — but I have to work so hard not to pull out my phone in that situation.

H: Yep.

A: Because what am I going to get by looking at my phone in that situation? Check my email for the thousandth time? Nothing is that important.

H: Isn’t there quite a lot of research to show that basically you get some kind of endorphin rush when you do that? It’s a little bit like using a kind of drug.

A: It is. And it’s hard to break yourself from that situation. I used to do this thing when I got off the subway, coming back from my apartment at night. I would try not to look at my phone for the three blocks and it was so hard. (laughing) You laugh, but try it, right?

H: No, it’s true, it’s true. I have a little son now, as you know. He’s 20 months and he’s at the age where he mimics everything you do and it makes you very self-aware of what you’re doing.

So the other day I was sitting having dinner with my wife and we both had our phones lying next to us and we were both looking at it and I was like I do not want my son to mimic the behavior of his mom and dad just sitting looking at each other through a phone.

And so we made this little rule now that we’re not allowed to bring the mobile phone to the table. And to your point right, like it sounds almost obvious, what the hell is going to happen in that 45 minutes that you can’t miss. If something really dramatic really did happen, what people wouldn’t just call?

A: Yeah.

H: I’ve done another hack with that — I started to have my email clients only pull emails every 30 minutes because often you send an email and it is just boomeranged back, right? There’s a good chance that one out of four you’ll get a response on…and so basically the more you send out the more you’ll get back.

A: What I try and do by the way — — and I try, it’s not that successful yet — — is I basically try to do email once a day at this point. I only actually open emails in the morning. Like there’s an hour in the morning where I go through all my emails and I usually get up through the previous day and then I’m done.

You know if something urgent comes in, I’ll flip through things throughout the day, just to kind of see if there is anything urgent, but if there isn’t I just don’t respond.

H: And do you think that you are less productive because of that? Or do you think that people get upset with you because you don’t answer?

A: I don’t think so; I mean 12 hours isn’t a crazy amount of time to wait for a response on something. What kind of world are we creating that everyone expects a response inside of 12 hours?

H: What do you think is another kind of micro-trend when it comes to the mobile? We have the text message or the text interface as being something that seems to have a lot of mojo. Are there other things that are happening that you think are interesting?

Like obviously the new OS of Android is very elegant and I think is getting very close to the slickness of IOS and it might even have some advantages because the notification system on Android is so good. Do you see other things happening in mobile that you think are really fascinating?

A: So I’ve gone back and forth between the two types of devices. I think I was on Android for a year and a half and now I’m back on an IPhone for the last six months.

And I always felt that Android had a lot of features that are completely superior to IOS as an operating system. And like a way to live your life.

But, all the phone makers keep screwing it up, so unless you have something running just straight Android, you’re not getting the real experience.

But in terms of the other things happening — the thing that I want to happen, honestly, I would love for Microsoft to actually become a real player on the operating system wars.

H: How come?

A: Because, well Apple is this unified system right? Where you have the phone and then the hardware and the software so it works really well together.

Google, for the most part, honestly, is just software. They had their phone unit but then they got rid of it and still don’t have as tight of control on it.

Microsoft is starting to actually prove that they have the chops to create great hardware. It started with Xbox, but now if you read the reviews about the new Surface, like the Surface 4 or the Surface book, they’re doing incredible things with hardware. Look at what they’re doing with the HoloLens. If you ever play around with a Microsoft phone, it’s actually got some really cool interesting features.

H: It seems that Apple kind of won the war by not going against the PC, but by inventing computer systems around it, like the IPod and the TV and then the phone and then suddenly you kind of needed the Mac, you know seeing they changed the infrastructure of the IOS and it became very good.

It would be interesting if Microsoft did that right back to them, like they do the HoloLens. If they do the game platform and then suddenly you have all of these devices that are Microsoft based and then you’ll end up back on the PC.

A: It might happen, but it won’t be just generic PCs. Maybe Microsoft does it, right? Like maybe Microsoft becomes the next integrated hardware/software maker, for the PC side. I can see it happening. Microsoft spends more on R&D than any other company or something like that. And there are still brilliant people there and they are capable of doing really incredible things.

And I don’t know that necessarily, by the way, that Microsoft is making the best stuff or will, but I think competition on this is great.

H: Wow, so you on tape are basically betting on Microsoft?

A: Ahhh, you know, I just love the idea of there being more options and competition amongst the major players. And startups are going to provide a lot of that and I think startups are going to create the next great companies, but these incumbents still have juice in them. And I’d love to see what they could do on a level playing field.

H: That’s very true. Okay, a few things here at the end. Do you have an app on anything that you’ve installed recently that more people should use that or that you’re excited about? It could just be a service online.

A: Let me take a look.

H: What’s on your home screen?

A: Yeah, what’s on my home screen?

H: I actually have a few…how many text-based apps do you have on your home screen?

A: The truth is, I don’t use many apps. Maybe I’m not supposed to admit this, but I have things that I kind of use on like a one-off basis.

H: I don’t really believe in the internet. (laughing)

A: The what now? The thing that I end up using the most are email and maps.

H: Yeah.

A: And then I try other stuff and all of the other stuff kind of comes and goes over time.

H: That’s fascinating. What do you think is the subject matter that people are not talking enough about?

A: Well, I think that there is a difference. I think that founders are talking about lots of things that maybe the press isn’t.

I think there’s a big problem with how the press talks about startups, where it’s kind of all about funding, which is fundamentally not the most important part, or the most interesting part, but it’s the easiest thing to write about.

H: I agree with that. I think that is incredible when you’ve done a few startups and you’ve done some that have done really well and sometimes you’ve even done some that go so well that you don’t need funding.

And then people think that it’s not going well because you haven’t been around raising capital and then you see companies that have raised all this capital and they’re going nowhere, but they raised a lot of capital.

A: Yeah it’s a crazy thing and it’s a crazy distortion. Things that people aren’t talking about though, I’m not sure. I’m really not sure. I’m also in the middle of like reading applications for the next YC batch so I’m seeing kind of a million different things so my brain is definitely a little frazzled.

H: Is there a trend in the new batch? Can you talk about it?

A: I’m seeing a lot of logistics companies in other countries, which is kind of cool.

H: And what kind of stuff? Like Uber type stuff or more like I need to get a product from A to B?

A: Yeah, more commercial stuff.

H: Oh, interesting. Do you think that the whole kind of the web app based world is going for enterprise now?

A: I think a lot of people are going after enterprise, which I think is good. I think there’s a lot to be done in enterprise, I think a lot of people who try it don’t realize quite how hard the sales cycle is, but I don’t agree that it’s like everyone is doing enterprise. I don’t think everyone is ever doing anything. There are rarely things that happen that tightly.

H: Aaron, you are an incredibly insightful person.

A: Thanks Henrik, I think the same of you.

H: Ah, thank you for spending all this time talking about mobile stuff. Is there anything that we forgot?

A: I don’t think so. I think that kind of covers everything kind of intelligent that I’ve been working on for the last month just to prepare for this.


The crucial difference between networkers and connectors and practical advice for introverts striving to network

When Michael Roderick went from being a high school English teacher to a Broadway producer in two years, he realized it was made possible by relationships. After stints both on and off Broadway, Michael founded his own company, Small Pond Enterprises. Small Pond Enterprises is a consulting firm focused on relationship design. Michael advises people on their professional relationships, providing guidance on where to invest time and energy.

In our recent conversation, he acknowledges the negative connotation often associated with networking, which he blames on “people who don’t do what it is that they say they’re going to do.” Notably, Michael differentiates networkers from connectors. While both parties focus on professional relationships, networkers, stereotypically, are focused on their own advances, while connectors are more focused on the success of others.

Michael offers a simple step people can take to practice the traits of a connector: “I think if you are just taking even a couple of extra minutes a day to think about what the other people in your life actually want, what is actually important to them? If you do that, you can start to move toward being more of a connector.”

He also offers a useful way to categorize the various types of connections — his ABCD concept. In his own practice, after a meeting, Michael notes what category the person falls into at that moment. Below are the categories with brief descriptions:

Advocates: people who are supportive and thoughtful

Boomerangs: people who are focused on reciprocity

Clients and Celebrities: people who have let you know they want you to work for them and people that it is “fancy to know”

Drains: people who are needy at that particular moment

Michael clarifies “that everybody is a celebrity to somebody.” He offers the example that if if a connection is a CMO, that person would be a celebrity to a company seeking to hire a CMO. He also notes that these categories are fluid.

Michael strives to learn beyond just the professional side of new connections, seeking out the personal and inspirational aspects of their lives, as well. In conversation, he notes any references they make to their personal life (where they live, their family situation) and their inspirational life (what inspires and excites them). He explains: “those little things are things that you can remember that really add an additional layer.” By writing down these facts after the introduction, the next meeting already has some common ground and talking points.

He also offers practical advice for people striving to make connections, including the “double opt in,” originally derived from Fred Wilson’s blog. In his own life, Michael has made a point of utilizing the double opt in which consists of approaching both parties and asking if they actually want the introduction. The practice helps to ensure the introduction is both wanted and warranted.

On the crucial difference between networkers and connectors:

“Networkers are people who are very focused on themselves and when you’re a networker, you’re really thinking about things in regards to climbing a ladder, so your thought process is often like who can I meet, what can I do and how can I get the things that I need to get?

…If you’re a connector, you’re really more focused on the success of other people. You have your own things that you want to make happen, but you don’t put those at the forefront of all your conversations…You’re not thinking about it as a game that you can sort of fix for yourself.”

On a metaphor for people who do not organize and evaluate their connections:

“If you had a bucket of change, you could have $2 in that bucket or you could have $2000, but until you dump it out and actually see like how many quarters you have, how many pennies you have, you don’t really know. So with wherever you are in your business, you know which people are the power players, you know which people are normally pretty helpful in terms of the work that you’re doing. Just start by, at the very least, sorting that out.”

On simple, practical advice for introverts striving to network:

“If you’re an introvert, rather than being like I’m going to go to this 200-person, 300-person thing, think about five to six people that you really like… Maybe you just put together a breakfast or a dinner…One of the things that worked really well for me when I first got started was this idea of hosting. Because when you put yourself in the position of a host who invited everybody over, you really don’t have much of a choice. Like you can’t sit in the corner, because you’re the one that invited everybody. So it kind of pushes you a little bit, but it’s not so uncomfortable as going into a room where you don’t know anybody.”

You can listen to the podcast on SoundCloud and subscribe on iTunes. In his own words, Michael strives for listeners (and readers) “to learn to be more thoughtful about the access that they have in their lives and how they treat other people.” Below are a few selected highlights, as well as the full transcript of our conversation.

H: Let’s do it.

M: Okay, you got it.

H: Are you ready?

M: Sure.

H: Okay, maybe if you don’t mind, just introducing yourself.

M: Sure, not a problem. My name is Michael Roderick. I’m the CEO of Small Pond Enterprises and I focus on relationship design. I help people take a look at their existing relationships and figure out where they should be investing their time, who they should be investing their time with, really thinking carefully about that.

I came to that having been a high school English teacher and moving from being a high school English teacher to a Broadway producer in under two years. So as a result of that, I decided to study the ways that we develop relationships and the ways that we build relationships and use these opportunities and connections to grow our own opportunities.

H: If people just listening to the first 30 seconds of this podcast, what do you think they will learn by the end of it?

M: I think they will learn to be more thoughtful about the access that they have in their lives and how they treat other people.

H: Hmm, fascinating. The reason why I was fascinated when we spoke the other day was because I think that people who network are often pretty annoying, right? So when somebody was like hey, here’s a guy who knows a lot about networking, I was like ohh, one of those guys. You made the difference between connectors and networking, because you think there is a subtle but important difference in the way people conduct themselves, but also what their objectives are.

M: Definitely.

H: Do you mind explaining a little about that?

M: Sure. Networkers are people who are very focused on themselves and when you’re a networker, you’re really thinking about things in regards to climbing a ladder, so your thought process is often like who can I meet, what can I do and how can I get the things that I need to get?

So you’re probably a little more savvy than people who are just sort of like bulls in china shops and just knocking down all doors. But for the most part, when you’re making introductions, you’re probably making introductions to people who are at the same level or lower and you are always trying to cut yourself in, in terms of that dynamic.

If you’re a connector, you’re really more focused on the success of other people. You have your own things that you want to make happen, but you don’t put those at the forefront of all your conversations, do you understand? There’s more of a balance, that some things will work out for you and some things will not. You will resonate with some people, other people you won’t. And you’re not thinking about it as a game that you can sort of fix for yourself.

The other thing that I think really distinguishes a connector, is that you’re willing to let somebody else leap frog you. So even if you know somebody that could make something pretty substantial happen for you, you will make the choice to introduce somebody slightly below you to that higher-level person that you know because you feel for that that person on that lower level. You’re almost like an agent and you’re saying: “I think that this person could be very, very helpful to this person at the higher level, even more so maybe than I could be.”

H: Do you think people can be a connector without that being almost their profession? It seems that most people — including the people listening to this — are actually interested in meeting and probably don’t see themselves as either a networker or a connector. How should people think about how they use their network? Can you be just a little bit of a connector?

M: Sure. I think so. I think if you are just taking even a couple of extra minutes a day to think about what the other people in your life actually want, what is actually important to them? If you do that, you can start to move toward being more of a connector. The other thing is that a lot of the time people don’t actually make introductions, even though they can see that there could be an opportunity there or people could be helpful. They just don’t take the time to think: “Okay, who in my life could actually really benefit from knowing somebody else in my life?”

So I think while you’re not going to be this major connector and doing all these things, just being a little bit more thoughtful on a daily basis of who are the people in your world and how might you be able to help and whom it might even be cool for them to know each other, even just once a week, being able to make one introduction can kind of change the dynamic of what you’re currently doing.

H: It’s such a subtle balance, right? Because I think a lot of people just like the idea of giving but at some point people also just need to think of their connections as being some of the value that they’ve got.

M: Sure.

H: I read…have you read Influences? That book?

M: By Robert Cialdini?

H: Yeah.

M: Yeah, I loved that book.

H: It’s a really, really nice story about fear. I think it was originally monks who came up with the idea — they give flowers to people before they asked for a donation?

M: Yep.

H: They basically will see the donations go up because of factor X.

M: Yep.

H: Again, maybe it’s a little bit the same, there is actually a science that proves being good actually helps you.

M: Yeah, there is, I mean there is a psychological aspect of reciprocity, where if somebody gives us something, we are inclined to give something back. So if we’re in the supermarket and we get the free sample, there’s a good percentage of us that will buy the full product because they liked the free sample, right?

H: So one of the reasons why we got to talking was because the partnership that I have with the database with all their contacts…and we have 25,000 people, whatever.

And we’re constantly looking for good people to join the projects and stuff like that and at one point it dawned on me: “Hey we probably know all these people, we just forgot we knew them.” And so you’ve been helpful in trying to help us basically sort out how we should think about that.

What would be your advice to somebody who is into their career, and has a contact list, is there something that they should really just start doing tomorrow that will make it easier for them to act as a connector and then also generate value out of that?

M: Yeah, I think if they haven’t taken the time yet to put that somewhere where they can kind of categorize it, they should. For some people it’s a spreadsheet, for some people it’s a CRM, but if you just sort of have like this massive list of contacts, you have no idea what sort of value you have.

The metaphor I often use is that if you had a bucket of change, you could have $2 in that bucket or you could have $2000, but until you dump it out and actually see like how many quarters you have, how many pennies you have, you don’t really know. So with wherever you are in your business, you know which people are the power players, you know which people are normally pretty helpful in terms of the work that you’re doing. Just start by, at the very least, sorting that out.

So if you’re in the real estate world, you know who has sent you good opportunities and good business. So you can say: “Okay, it looks like these 10 people seem to send me a lot of business. I wonder what the commonality is between these 10 people? Oh my god, they’re all lawyers, oh that’s interesting. I wonder why this is the case?” And then you start to dig in and you start to figure out, why is it that this group of people seem to send me more opportunities than this other group of people?

H: When you’ve done that for yourself, have you figured out where the patent is?

M: Yeah, I would say that the biggest thing that I’ve noticed is that the people who…I like to refer to them as advocates…they are people who are very thoughtful, some of them are connectors, some of them are not, but they’re really thoughtful, they’re always asking you really good questions and they really take the time to figure out what is an actual referral versus a connection?

And I think a lot of the time people mistake the idea of a referral and a connection. So they’ll say: “Oh I sent you a referral.” But you get on the phone with the person and they have no idea that you have a service, no idea what your price point is and they’re almost flabbergasted that you’re going to talk to them about you know buying something or using a service.

Whereas if somebody takes the time to find out what is your price point, what type of service do you provide and then tells somebody, has that conversation ahead of time, they’re in essence handing you a warm lead. So what I’ve found is that my advocates are people who have taken the time to talk to me about what it is that I do, talk to me about who I serve and what my price point is and then actually send those people my way.

H: How do you change people from being referrals to connectors?

M: You have to have an honest conversation. I think a lot of the time we don’t want to have those uncomfortable conversations, so people will send us things that aren’t really useful for us and most of the time we’ll just kind of sweep it under the rug. Like well you know, that’s just who that person is, but you’ve got to go back and have that conversation.

You’ve got to go back to the person and say: “Listen, you know, I really appreciate you thinking of me. It means a lot that you think of me. Right now when I talked to this person, they had no idea what my service was, what I was actually doing. So would you be willing to, in the future, give them a little bit more color before making the introduction? Or have a conversation with me before making the introduction?”

And certain people are going to be like screw you, you’re way too specific, I hate you and go their way. And other people are going to be like thank you so much for the feedback, I really appreciate that. And they’re going to think about ways that they can do better.

H: I think that’s an interesting thing because I think we all have people who are very kind to refer people to you and sometimes the high-quality introductions happen because they need something from you. You talk a little bit about double opt in…

M: Yeah, double opt in. Yeah, it was originally introduced by Fred Wilson on his blog. The concept is you basically go to both parties and you ask them if they actually want the introduction. And I have made it a point to start doing this with all of my introductions, because you never know what is going on in somebody’s life.

And you may make introductions between two people, and think wow, these two people are fantastic, they’re going to love each other, but you just made an introduction at a time when somebody is about to launch a business. Or you just made an introduction at a time when somebody just lost a family member.

And now this person on the other side is thinking your friend is a jerk because they haven’t gotten back in touch and they have no idea what’s going on in that other person’s life. But, if you take the time to ask both parties, they’re going to give you an honest answer as to whether or not they even have the bandwidth right now to take that introduction. And, also to let you know whether that introduction really is warranted and really is useful and helpful.

H: It’s interesting because after we spoke, I started to ask people about it so sometimes now when I get these cold indirect directs and I email back and say: “Hey, it’s a really busy time, I’m traveling over the next two weeks and I don’t want you to look bad so would you mind sending me an email next time just kind of saying, ‘is it okay to make introductions?’” People seem to very open to that. Yeah, they seem to think it’s a good idea.

M: Yeah, it’s one of the things where a lot of the time we worry so much about how people are going to see us when we ask for something, especially when we ask them to clarify or help but very rarely does anybody come back in and just be like a total jerk.

I mean my attitude about that is if somebody comes back after I’ve politely asked them you know to help or solve a problem and they come back in and they’re just absolutely rude, then that’s what anybody I send their way is also going to experience, so I don’t want them in my network and in my world because that ultimately reflects back on me.

H: You have a framework for how you are talking about people, you mentioned one of them. Could you talk a little bit about the ABCD concept?

M: Sure, sure. So the ABCD concept is that your first serve top tier people are your advocates, which I spoke about. These people really support you, they’re really thoughtful, they’re really helpful. Your Bs are what I like to refer to as your boomerangs.

And your boomerangs are people who are very focused on the idea of reciprocity, so often you’ll encounter people in life who are brokers of some type and they will say if I do this for you, I get this percentage or you know, whatever the situation is. And very rarely do they send anything your way, unless something is sent their way. They’re very, very focused on what you are going to do for them and then they might send something back. It’s very transactional.

Then you have your Cs, which have two categories. Your clients and your celebrities. So clients are people who have let you know that they want to work with you. They’ve asked about your services, they’ve kind of broken it down, in some cases they’ve asked about your price point, etc.

And then your celebrities are people that it’s fancy to other people that you know this person. And that could be a Hollywood celebrity or it could be something as simple as a CMO of a particular organization. Because if you have a company that is obsessed with finding CMOs and that’s the most important thing to you, the fact that somebody else knows a CMO, for you that person is a celebrity, that CMO is a celebrity. And it’s really important when you’re thinking about this idea of a celebrity, that everybody is a celebrity to somebody, so really thinking through who you are connected with and what do people think of that particular individual.

And then the last one…the last category are the Ds, which I refer to as the drains. And it’s really important to understand that this is not that drains are bad people, it’s that drains are people that are significantly more needy in life, at this point in their life than others.

Which means that you, as somebody that can help or support, you only have so much energy to deal with people who cannot even comprehend being able to support or help back because they’re in such a state of need or pain.

So it’s important to understand the people who are draining you of your time and your resources and not necessarily to always say like you know there’s folks that I don’t want in my life, but to understand that I can’t give three hours of my time to this person who is not going to ask me anything about me and basically spend the entire meeting or conversation trying to get as much as they possibly can.

H: And so you categorize people as A, B, C, D…do you actually write that down or do you just think about it?

M: Yes. I always document it. So when I finish a meeting, I write down what my first impression is and that can change over time. People can start out as advocates for you and over time they start to become more boomerang-ish, where it’s much more trading. Or some people you may meet and at the very early stages of their career and maybe two, three years down the line…they’re a celebrity. You never know where people are going to end up.

H: Why do you think that networking and connecting has such a bad rap? I would imagine most people either feel neutral or cringe slightly.

M: I think because there are people who are out there who don’t walk their walk. And I have this saying that it’s very unfortunate in life that many times your heroes are only your heroes until you meet them face to face.

And there are lots of people who will present this idea of networking, connecting, helping each other, and supporting each other and then you’ll get on the phone with them or you’ll meet them and they will basically treat you like crap because you were not at the level of whoever they want to meet or whoever they want to connect with.

So I think that one of the main reasons that networking, connecting ends up having a bad name is that there are a lot of people who got to a certain place as a result of being sort of savvy and smart about networking and connecting, and maybe they’ve even started to teach other people sort of this process. But then when those same people come to them and try to use those principles or get to know them, they’re still treating them like second-class citizens.

So when you have that many people who get burned by the experience, what happens is then there’s sort of this hubbub of like networking is BS or connecting is like ewww. So all of a sudden you’ve got this murmuring amongst the crowd, I think that’s what happens. I think that people get introduced to these concepts but then there are a lot of people who don’t do what it is that they say they’re going to do.

H: Do you have any good advice for people who might be more on the introvert side? Networking seems to be an extrovert’s game.

M: Yeah. I’m very introverted myself, though, every once in awhile I’ll have extroverted tendencies, but I love one-on-one conversations and I actually get very drained if I’m in a large crowd for any long period of time.

So I think that if you were an introvert, the very first thing is you don’t have to go to a gathering of 200 or 300 people. You do not have to go to that. If you want to go as a way to stretch yourself, fantastic. But you don’t have to do that to build relationships. If you’re an introvert, you need to make it on your own terms.

So if you’re an introvert, rather than being like I’m going to go to this 200-person, 300-person thing, think about five to six people that you really like and maybe you could find somebody that might be a co-host. Maybe you just put together a breakfast or a dinner, or some sort of gathering where you get a bunch of people together but you’re the one hosting.

One of the things that worked really well for me when I first got started was this idea of hosting. Because when you put yourself in the position of a host who invited everybody over, you really don’t have much of a choice. Like you can’t sit in the corner, because you’re the one that invited everybody. So it kind of pushes you a little bit, but it’s not so uncomfortable as going into a room where you don’t know anybody.

The other thing that I would say specifically for introverts who get stuck…I have this concept of when you’re in a crowded room, it’s sort of like the ocean and within that ocean there are a couple of archetypes.

So you have your sharks, who are the people who are like running around handing out business cards, dominating conversations, right? You have your dolphins who are the people who are clustered together and won’t let you into their circle, right?

You’re at this event and the dolphins just want to stay with each other and you’re like hovering on the outside and you kind of feel awkward, right? And then there are those who are drowning. And these are the people who are like sitting at the bar, they’re like standing with their phone or they’re hovering outside of a conversation and they’re feeling very uncomfortable.

The last group are the lifeguards and the lifeguards are the people that basically look around and say: “Who is feeling uncomfortable and why don’t I go up to them and have a conversation?”

I would say if you’re an introvert and you’re freaked out, one of the best things that you can do in social situations where you’re really worried is to be a lifeguard, because very, very rarely will you go up to someone who is feeling uncomfortable and miserable, say hello and have them be like get the hell away from me. They’re going to be like “thank you so much for talking to me.”

H: So you coach the person standing looking awkward at phone…what would you open with?

M: I might just ask them: “So what brought you here?” Or something very, very simple, like, “did you see the most recent speaker?” Just something to get the conversation going? Heck, if they’re on their phone, it might even be the new iPhone, and that can be a conversation starter, too.

Just something to make them feel less uncomfortable. Because I know that was something that I struggled with — going to an event where I didn’t know anybody and then having to sort out who I should talk to. And many times the people who I ended up building the best relationships with were the people that came up to me while I was standing there sort of awkwardly and said: “Hi, I’m so and so. What are you doing here? How are things going?”

H: I like that…be a lifeguard.

M: Yeah, it’s so, so useful…it’s so, so useful.

H: If you are just starting to think about your contact list and this idea of putting it into associate and taking long notes after one sounds kind of daunting.

What do you do to get things going without committing too early?

M: Yeah. I think it’s one of those things where the how do you eat an elephant, one bite at a time kind of scenario fits. What is something really simple that you can do to just make it a little more expensive for yourself?

So maybe you start by taking a notebook with you to meetings and after the meeting, you jot down the things you remember. Maybe you’re not sitting there voraciously taking notes, right?

Maybe you have a great conversation and at the end of that conversation, the person leaves and you take a couple of minutes to say: “Okay, they told me they loved dogs, they told me that their wife is a doctor, and they live in Brooklyn.” And now you’ve got three points of conversation, that then you can sort of add that knowledge into the mix and you know more about them.? You remember those pieces. So I think something just that simple can really help that process.

H: When do you see connecting go really wrong?

M: Oooh. Definitely when people don’t ask. When people don’t ask, they don’t do the double opt in and there are circumstances that we just don’t know about. I’ve seen instances where somebody’s like I think these two would really enjoy meeting each other and they make the introduction and they’re competitors. Or the other person dated this guy or this girl, and it was a horrible experience for them.

I’ve seen instances where people have made an introduction and please don’t ever do this: If someone makes an introduction and you’re interested in dating the other person, don’t use a professional introduction from somebody else to ask somebody else out on a date. It’s just awkward. I had somebody come back to me one time, and be like what the hell? Why did you put me in touch with this person? They just asked me for a date. And I’m like ohhh, ewww, I thought that they wanted to talk to you about business, I guess not.

H: You mentioned a framework for what to ask about when you are in meetings with people, which I thought was pretty interesting. Most of us, ask what they do, what kind of a transaction and maybe there might be some kind of a personal kind of an introduction as you’re leaving.

But you’re trying to get a much more realistic picture of people when you’re talking to them because you think you can…I hate to use the word “use” but let’s say a good piece of information for creating rapport in relationships going forward.

M: Exactly, it helps sort of deepen the relationship if you’re able to touch on more than just the professionals.

H: So what would those be?

M: The first one, as I said is the professional, where you sort of get a sense business-wise, of where things fall. The second one, is the personal, where even if it is something as simple as finding out where somebody lives or if somebody just lets you know that they’re married or that they have kids…just the little things like that. Sometimes they’ll talk about the type of things they like. If you’re offered coffee, sometimes they’ll talk about the type of coffee they like.

You know, those little things are things that you can remember that really add an additional layer. In addition to the professional, I also like to look at the idea of inspirational. So what is it that inspires this person and why does this person like to do what they do? Because sometimes you can connect people around inspiration.

Sometimes, even though professionally they’re not doing the same type of thing, they’re both inspired by similar concepts and similar ideas, so you can kind of put them together, which is a really interesting dynamic when you start to look at what is it that excites this person, right?

So if somebody is a really great connector or loves being a connector or loves geeking out about connecting, their industry may be completely different from somebody else, but they’d be willing to meet each other because they both geek out about connecting.

H: When you have a person who wants an introduction to somebody else and it’s kind of more in the favor of one person than the other, but you’d still like to make it. Do you have a trick or method for doing that? Or do you just right straight up when you do the double introduction say: “Hey you might not be able to get a lot of stuff out of this person, but please be nice to them because they’re a nice person or I owe you one.”

M: Yeah, I try to. If I think that they have the potential to do something or help in some way, I will try to sell that to the other individual. And in some cases it could be who they worked with before, what types of things that they have worked on or it could be you know, I met this person and they’re just a phenomenal person, I’m not sure where this could go, I’m not sure how much you guys would be able to help each other, you may be able to help them a lot more, but I can tell you that this person is a great person.

H: Are you ever worried that you kind of caught by the intro? Sometimes when I know a founder who has a job opening and somebody emails me and asks for an introduction, I feel caught.

M: Yeah.

H: I sort of feel that way. I might know them from social events or stuff like that. But, I sometimes feel, that if they hire them and it doesn’t work out, then I feel on the hook because I made the intro. And so now increasingly I do a little bit too much of explaining: “Hey, I know this person, they seem to be super nice, I’ve never worked with them, but you know, they seem to be a perfectly good candidate for this opening you have and so do you want an intro?”

M: Yeah.

H: Do you think it’s worth it? It’s obviously a gift back to the original intro, but it’s also…it could be like a big gift and the downside could be pretty big because if they suddenly are a horrible person…

M: Yeah, I think what you’re talking about is so important because what you’re letting the person know is that you don’t have a very solid connection with this person. You are letting them know that you don’t know them that well. And you’re like, from their qualifications it seems like they’d be a good fit.

So when that person has that poor experience, what are they going to do? They’re going to go back and look at what you wrote, right? If you wrote, I don’t really know them that well, I think they have these qualifications, then, if it’s a bad experience, well it was a bad experience, but Henrik never knew, so that’s the thing.

A lot of times when somebody comes to me and they want an introduction, I’m always going to ask them what it is that they want to talk to the other person about. Especially if they’re coming sort of randomly, and what’s interesting about that, and this can work really well if you’re in a position where a lot of people come to you for introductions. Many times, just going back to the person and asking them why will tell you immediately what kind of person you’re dealing with.

Because people who are just trying to get something very, very quickly won’t even take the extra effort to explain to you why they want the introduction. They’ll just ignore you and sort of go on…

H: Or they’ll just ask for a meeting. And then you’re up against your back and wondering what they want to meet about?

M: Yep, exactly.

H: I’ve done that a few times. If I’ve been traveling and I don’t have time for coffee, I’ll email back and say: “Hey, I’m on the road but maybe you can list down a few things where I might be able to tell you whether or not I can help you over email.”

And you’re right, there is definitely a big drop-off rate of people that just can’t be bothered.

M: Right, where they just won’t give you that information. And I think anytime you’re thinking about making an intro for somebody, where it could be for a job opportunity, you definitely want to ask them why they want a job at that place. What is it that they’re actually interested in? Because if somebody is interested just because it’s a job, they’re probably not going to be the best fit for that organization.

But if they’re like: “I read about them. I really like what they do.I really respect what they do. This is a company that I’m really interested in.” That is a different dynamic than somebody who’s just like, oh my god, I need a job.

I really think that serendipity is a really good way of solving problems, right? If you know somebody that you really respect and like and think do great stuff, then chances are high that when you go through them you’re going to get good people. And that definitely works on the inbound. When somebody that you really like introduces you to someone they like, there’s a pretty good chance that you’ll like them, too.

H: Do you ever use that in a reverse way? For example, if I have a problem to solve and I actually don’t know if this specific person will be able to solve it, but I’m sure that if I asked them and they know somebody who could solve the problem, I would like them. So I email somebody I really like and say: “Hey, I’m trying to find a person for this or I’m trying to find a good solution for that or for something else.”

M: Yep.

H: Do you ever do that? Is that part of the framework?

M: Oh yeah, all the time. There was a study done by Mark Granovetter that was referenced in Gladwell’s Tipping Point. It was known as “The Strength of Weak Ties.”

Basically, they took two groups of college students. One group asked their close friends and family for jobs and the second group asked people that they kind of barely knew or maybe met like once or twice in their lives for jobs.

And the second group outperformed the first. So, if our strongest results come from our weakest connections, then it would make sense that if we reach out to people who really like us, those people have access to people that we have no idea that they have access to. And, they don’t even know that they have access to those people until we ask them to solve a problem.

I notice that some founders do this really well. They will send investor updates and then at the end of it, they’ll say here’s three things you can do to help. And they’re like we’re looking for this person, we’re looking for this person and then they…I find often that it’s a pretty useful way to solve those problems, because that’s such a good point. I suddenly look at it and to choose somebody that they didn’t know themselves and yet that was useful for that problem.

H: Do you have any like tools that you can recommend to me? Like do you have a new app or is there a new service online that you just recently just discovered that people should just know that this exists?

M: Yeah, there’s one that’s in beta right now. I imagine right now you’d probably have to just like put your email address in and maybe it will get to you kind of thing. But it’s called Brief and it’s an algorithm type of thing. Basically you put your info in and every day it reminds you of three people that you just haven’t touched base with. And it’s very, very short. It’s connected to your Twitter and your email.

It will send three things every day and it basically says you haven’t talked to so and so in 11 months, retweet their post to let them know that like you know they still exist. Or you have not answered so and so’s email and it’s been like seven weeks or something like that. I think that where this app is doing something different from a lot of the other apps that are out there is it’s brief, right? It’s three things, so it’s easy for you to do. Just three reminders or three sort of ideas for you to take care of.

H: That sounds cool.

M: Yeah, it’s been cool. I’ve definitely been finding like oh wow, I didn’t realize that I hadn’t touched base with that person in a while.

H: You also introduced me to Contactually?

M: Contactually, yeah. Contactually is incredible because it gives you this ability to do your curating and research in your emails. You can tag people and take notes about them while you’re sending your email. You can put them into buckets and all these different types of things, so it’s much easier than if you were sort of sitting down trying to sort all of it.

I sort of live in my spreadsheets, but it’s a very useful tool to be able to just sort of tag people within your email and have that information. And Contactually has a similar feature of reminding you when you haven’t been in touch with certain people, but you can set it. So unlike Brief, which is sort of random, with Contactual you can say, you know I want to make sure that every 30 days I reach out to Henrik, then it’s there and you know it. I like the fact that they do that.

H: If there is something to leave people with that you think is important or if they want to learn more, is there kind of a go to resource or…

M: It’s interesting; it’s sort of a collection of resources that you can go to. I mean I think that if there are people listening to this, this is kind of your first step. It’s kind of the benchmark of understanding psychology, like psychology 101. They want to figure out why people say yes to things and why they say no to things. I think that at the core is a really solid starting place, but you know there have been a lot of books that have started to tackle this concept, of how to win friends and influence people.

H: Switch I think is really good.

M: Yeah, Switch is incredible; it is incredible because it gets you thinking about why we make these decisions, why we make these choices. Another one that I really enjoyed was Smartcuts, by Shane Snow. What he did in that book was take a look at all these different people, who in essence, kind of skipped the line. Like, they started in one place and all of a sudden they were like way the heck up here and he starts to identify these very specific principles as to how they did it. He gives some very, very specific subject matter, ideas, and concepts and I like that because there’s not a lot of stuff out there that does that.

H: That’s cool. I’ll leave a link to it in the notes. Thank you so much for spending time talking with me.

M: Thank you, it was a blast.

H: It was really, really enjoyable.

M: Awesome.