What is Medium? I get asked this question frequently. Not by people who write on Medium, or people who read Medium, but by people who feel like their professions might be impacted by Medium. Namely the media industry, investors, content marketers and professional writers. Evan Williams’ involvement is certainly part of the intrigue but I don’t think fully explains the interest. Rather the desire for explanation comes from a series of seeming contradictions that left people trying to define something still evolving in front of them. A publishing tool, but one which pays some of its contributors. A technology company, but one which hires editors and agents. An agnostic platform, but one which heavily promotes showcase content. Medium is a platypus!

Recently though I’ve settled on how I describe Medium: it’s a magazine created by the 9%. I know, that’s not really clear without explanation. Let me start with the 9% piece first.

There’s an internet rule called 1%-9%-90% which states 1% create, 9% comment/interact/curate, 90% consume. Let me borrow this construct and apply it specifically to web publishing:

• WordPress is for the 1%. There are content creators who want their own dry piece of land, a full featured CMS and total control over their blog. I am one of these people. These folks also are happy to deal with their own content promotion and try to build an audience. They construct their own themes and topics to write about, and most of the content is original to them.
• Medium is for the 9%. These people want to write but don’t want to maintain a blog (hence the publishing tool and centralized namespace). They sometimes need inspiration or to feel like part of something bigger (hence collections). They aren’t focused on driving their own traffic (hence promotion). They don’t want to blog daily or necessarily establish an ongoing readership. They like feedback (hence comments) but don’t want to get into flame wars.
• Tumblr is for the 90%. The masses want to collect, comment and republish other people’s assets. They use Tumblr to express themselves. They’re part of a community and the content they create gets pushed and reblogged via Tumblr Dashboard. Most of the content is not fully original (that’s not to say there isn’t unique content on Tumblr or that the remixing itself isn’t highly creative, more so that if you look at Tumblr in its entirety – not just the popular hipster urls – it’s a lot of YouTube videos, imgur pics, etc. Not a judgment).

Succinctly, Medium occupies the space in-between WordPress and Tumblr. A creative space that’s less complex than a CMS but more geared towards writing original medium-longform content than Tumblr.

For consumers, Medium is a magazine. I don’t think the Medium team has accomplished this yet but that’s the metaphor they hold in their mind. Collections of thoughtful content based on your interests that is somewhat evergreen (notice their lack of emphasis on publish dates). The homepage increasingly serves as your personalized table of contents and even as you finish one article, they’ve preloaded the next for you. The design is clean and page like – consistent white margins, single column text.

While I’m not really in the 9% creators (I do publish occasionally on Medium but find http://www.hunterwalk.com to be more fulfilling), I am in the 100% that enjoy reading Medium. That said, the “contradictions” highlighted earlier create a veneer that leaves the service a bit more amorphous than it otherwise should. When it feels like it doesn’t know what it wants to be, it prevents me from emotionally attaching to it.

Why? Because it does matter to me whether some content is paid or volunteered. I feel like I don’t want to get too excited about a writer on the platform who is paid because their content will only continue along with the dollars. I want to attach myself to voices that would have previously gone undiscovered and unrecorded (the 9%), not writers who are effectively freelancing on Medium (the 1%).

I’ve also found myself disappointed when I encounter content that’s poorly written or crude or cliche hipster pageview grubbing. My reaction is “who let this on to Medium!” I’d never say that about a YouTube video or a Twitter account or a Blogger site. My assumption is that those are just tools where anyone can publish. But Medium is different – it’s not a fully open platform so I’ve imbued the http://www.medium.com/ URL path with a notion of editorial vetting. Because if they want to be a publication, that’s what I’d expect – someone did the filtering for me. But if they want to be a platform, and anything can occur on a Medium URL, then I’m forgiving but also will wait for the good stuff to rise up to me from my social graph, rather than build an ongoing visitation habit to Medium.com.

It’s like I want to decouple the publishing tools from the periodical. I want the Medium.com URL namespace to mean something. Let anyone use the tools and push content to a different central URL namespace, but let editors and algorithms turn my Medium into something which is reliably good for my tastes. Each time I click on a Medium URL that doesn’t interest me, it pushes me away from Publication and towards Platform – each of which has different cognitive expectations for me.

I don’t know whether these feelings are strangely my own but the Publication vs Platform distinction still gets in the way of me embracing Medium as tightly as I want to despite reading more and more good stuff on there each day. Having published on Blogger for 10 years and Twitter for 6+ I’m content to trust in Ev that the team may eventually have an even better answer than I do for “What is Medium.”

Disclaimer: I’m on WordPress Board of Advisors and friends with many Automattic folks. I’m friends with Ev and other folks on the Medium team. I know nothing about the future roadmaps for either company. 

Several months after starting our Homebrew seed fund I’m often asked “what are some things that surprise you?” My answer doesn’t have to do with dealflow or investment strategy. What really surprises me is how many similarities there are between being a parent and being an investor. And it’s about control.

As a product manager one of my fallbacks was the notion I could always do the task myself if necessary. I knew how to solve those problems. Of course I had a great team of product managers who owned their own scope of responsibility but if they had trouble, I would step up and help them finish it, or just do the work myself from the start. The liability to this style – documented in some of my 360 degree reviews – was that I could be hard on my team, that I sometimes needed to be more clear about expectations and then get out of the way. I recognized these issues and over time improved, but still hung on to the mantra that on my watch, I’d put it all on my shoulders if necessary. I thought I could make anything into a diamond if I just squeezed hard enough. If I applied enough pressure.

Fast forward to 2011 when we found out my wife was pregnant. Eschewing the dozens of new parent advice books I promised myself one thing: that I would approach being a dad differently than I did building a product. That I would try to provide guidance, support, a consistent point of view, stern feedback when necessary, but that I wouldn’t try to plan my daughter’s life. As parents we’d give her all the love and resources she needed to find her passions but it was ultimately her freedom. We are heavily invested in the outcome – with all our heart – but that her life was her script to write, not ours to hand over.

Six investments into Homebrew there are some similarities. Our mantra is to provide seed capital, operational expertise and love. Of course the founder<>investor relationship is much less paternal than the one I experience with my daughter but there’s a commonality. Namely that the most successful companies find their own path, not one I – or any investor – prescribes. Our investment is made with conviction that a great outcome is possible – fulfilled founders & employees, enriched backers. And as investors, we provide encouragement, information, capital and sometimes even deliver tough messages. But we don’t produce these results by just squeezing harder, because additional pressure isn’t how to turn a startup into a diamond, it just hurts your hands.

Technology is People. Whether it’s building your team, pitching potential partners or mining sources of capital, at the end of every decision is a person, so relationships still matter. Fortunately for founders, we’re living in an ecosystem where accessibility is increasing. Sure it still takes time to build trust, but if you think back to the limitations of 5, 10 or 20 years ago, it’s clear email/LinkedIn/Twitter are far more open platforms than, say, a Rolodex. Still takes work – especially if you don’t live in a tech center – but if you hustle, if you build something, if you contribute interesting ideas on blogs, you’ve got a chance to build a reputation.

“Who should I meet over the next 3-6 months?” A NYC-based entrepreneur who recently left his startup after a successful exit asked me this question, talking about how he’d gotten to know a few well-respected tech investors and founders. One path would be to crawl this network and ask them for introductions to other tech Bold Faced Names.

My advice was to do the opposite – spend time building out your relationships in areas that aren’t well-known to the rest of us. For example, since this particular operator has deep mobile knowledge, he could ‘trade’ that expertise for discussions with top CPG or retail execs. Instead of just getting to know the VC or founder one degree removed from his current friends (he can get those introductions any time), establish a base of expertise and connections that others want to transact through. Become the guy who can connect you into a particular industry. This has happened recently with celebrities, US government and international companies – there are several investors who have put significant time into bridging the gap between tech and these spheres. Now they’re the go-to people for those areas, leading to privileged deal flow and information.

Sociologists call these “weak ties” – the theory that the most valuable nodes in a graph aren’t just connected to each other (“strong ties”) but also have connections into individuals outside of the main group. This is where new knowledge and resources come from.

So whether you’re doing 50 Coffee Meetings or taking some other approach to building your network, think outside of the social graph and find areas where you can be the connection back to tech scene. It’s a longer-term bet than just trolling Sand Hill or SOMA but one which will give you social capital and unique perspectives.

Advisory boards come up often in conversations with founders, especially early in a company’s life when they’re looking to build out expertise, industry relationships and social proof. I’m not a big fan of the “social proof” motivation, pairing the right advisors with shared expectations can create value which goes way beyond the small amount of equity they’re awarded.

I’ve found you can separate advisors into roughly two types – Practitioners and Coaches. Practitioners are advisors whose value is based on a specific skill or ability (for example, make introductions or teach your marketing team about SEM). I’ve written previously about looking for Practitioner advisors who can “teach, not tell.” You want them leaving your organization stronger, not just telling stories about what they did at company XYZ.

Coaches are a bit different. As opposed to imparting a skill or filling a gap, they’re more like mentors, helping you – or another executive on your team – perform at a high level. For example, you might have a Coach Advisor who has built out large inside sales teams before and they can work with you over the course of several years on hiring, training, rewarding and evolving this part of your organization.

What are some differences in the structure of advisor agreements for Practitioners versus Coaches?

• Length: Advisory agreements are standard two years. For Practitioners you might consider a shorter span since their input is likely to be more concentrated. I wouldn’t go for less than 12 months though – if you need someone for less time, just set up a contracting agreement.
• Frequency of Interactions: Practitioners can often just drop in and add value whereas Coaches need to understand your strategy, capability and culture. Accordingly you probably want to establish some frequency of meeting with Coaches (anywhere from monthly to quarterly) whereas general email updates are fine for Practitioners since they’ll be used “as needed.”
• Investment: Giving Coaches a chance to invest in the company (or asking them to do so) makes sense because of the deeper interaction and ongoing commitment. You want them to feel connected to the enterprise. With Practitioners, it’s a nice complement but not a necessity.

While not everyone is a fan of Advisory Boards, I believe they can be valuable. Does your startup have advisors? Have the been worth the time and equity?

From an interview in Fortune with John Deere’s CEO:

How precise is agriculture getting?

On our equipment — large combines, large tractors, large sprayers — we have proprietary GPS that enables what we call auto-steer. We don’t even want the operator to touch the steering wheel. Going up and down a field a mile each way, if the farmer has a 60-foot boom on the back, 30 feet on each side, there’ll be only a two-inch overlap. Prior to this, a farmer would have overlapped by at least six feet.

Design isn’t just pixels and beauty; it’s about producing emotional connections with consumers. The rise of design coincides with the mass adoption of smartphones and tablets. This isn’t a coincidence. These devices are heavily anthropomorphic. You hold them in your hands, close to your body. You touch, pinch, swipe and stroke to produced desired outcomes. They sit in your pockets, close to your groin. You worry about them getting tired (battery life). And they feel warm to the touch after long periods of use. You worry about them getting tired.

If design is about emotion maybe your product has an emotional DNA. That is to say, design can help expose or amplify the soul of your product. Sometimes to the point of taking a small squeak and turning it into a SHOUT. But one thing design can’t do is disguise or alter the core of your product. At what’s at that core? Some combination of three motivations: Love, Greed and Fear.

My thinking is that all products are born out of some combination of Love, Greed and Fear. Love is the most powerful – long lasting, ability to evolve over time, easy to root for. Greed may be important to have in a secondary seat. It allows you to see opportunity and aggressively pursue it. The drive to have everyone use your product. Fear is weakness. It’s lack of originality. Products dominated by fear will always be hollow, will always be tainted. Something will just feel off.

The products I feel closest to have Love, some have Love + Greed. I can’t think of a product born out fear that makes me happy, or has been successful over time.

Google is Love + Greed. Amazon is Love + Greed. Foursquare is Love which needs some more Greed. Instagram is Love.

Fast-followers which are Greed can survive. Fast-followers which are Fear + Greed will never resonate with consumers.

This is a philosophical and incomplete lens through which to think about products and their origins but it’s sticking with me.

I love when people quit their jobs. Ok, that’s probably a bit strong. Let me clarify. I love when people leave a job because they’ve made an impact and want new challenges; or feel they could be accomplishing a greater number their goals somewhere else. But when these folks approach me for advice as to what to do next, there’s one question most haven’t asked themselves. And it’s a critical question. I don’t know how you decide without answering it first.

The question is, What Are You Optimizing For?

Now let me caveat that this question is most important when you’re deciding between several good opportunities. In a tough economy there are many who feel lucky to hold on to the job they have, and those making a transition might not have the luxury to hold out for the “perfect gig” or even be able to find a new one easily.

The most successful folks are rarely trying to decide between a good option and a bad option when it comes to employment. This is especially true in today’s technology sector where it’s not uncommon for skilled engineers to have almost daily inbound interest from recruiters, founders and former colleagues. Choosing between a good option and a bad one is easy – don’t do the bad one. However when you’ve got multiple intriguing roles available to you it’s not a question of good vs bad or right vs wrong. It’s a question of which one is best for you in this next phase of your career. And to do that you need to decide what to optimize for.

When you are clear on your prioritization, the resulting framework can cut through the noise. I find it helpful to narrow down to 2-3 attributes of how you’d describe the “perfect job” for you at this moment. What are some things you can choose to optimize for? Well the list is near endless so you can start by just naming all the characteristics important to you. Examples could include: nearterm compensation, longterm compensation, commute time, quality of colleagues, brand reputation, title, geographic location, flexibility of schedule, quality of manager, health benefits, and so on.

Next is the hard part – the narrowing. You need to be firm and clear. These decisions aren’t indelible but you’re trying to end up with a job that will meet your goals for at least 2-3 years, so be thoughtful and honest with yourself. Once that’s done, start force ranking or any other assignment of relative value for each attribute to the job opportunities you’re currently considering. At the end of this process you should have one or two ideas that rise above the others. Those are what you should pursue the hardest. If it doesn’t feel right then you’ve either misjudged what you want to optimize for or gotten your rankings wrong. Revisit.

Post-job change you can check back in every six months or so to assess whether you were correct in your assessment of the job you took and whether your optimization has shifted based upon your own evolution, life events, and so on.

This process helped me ultimately make the decision to leave Google and start my seed stage venture firm Homebrew. Prior to being honest with myself about what I was going to optimize for, everything I considered doing next was just a list of pros and cons, and it was difficult to turn that into conviction. With this process I let some other good opportunities drop away because I knew they weren’t right. And Homebrew was so clearly what I wanted to work on.

Good luck in any current or future career search!

Most anyone successful in technology has benefited from those who came before them – whether it’s indirect such as opensource code or more specific, like the guidance of a CS professor. Even if you’re just starting out in your career, there’s an opportunity to develop a ‘pay it forward’ mentality.

Code2040 is one of the organizations trying to solve the mentorship gap for Blacks and Latino/as. Each summer they match high performing software engineering students from these underrepresented groups with Mentor and summer internships. I’ve participated as a Mentor in each of their first two years and intend to do so again in 2014 – I’ll put more info at the end of this post if you’d like to join as well.

One additional thought about creating a culture of contribution in tech. “Defaults” are powerful – they convey norms and expectations. I’d love to see LinkedIn standardize the notion of community service as a field in your profile. Not just as a text box but as something where your profile is only 95% complete unless you fill in a charity you volunteer with, a person you mentor or a nonprofit Board you sit on.

[Update: LinkedIn let me know you can add volunteering info to your profile via this link]

Key Dates and Info for Code2040

Round 1 Applications: November 10th

Round 2 Applications: February 9th

Students can apply at apply.code2040.org

Companies can hire a Fellow at hire.code2040.org

Recommend a student: bit.ly/2040REF

Code2040 Stats To Date

UpCounsel, the leading provider of on-demand legal services, announced their funding today (yippee!) led by Homebrew (yippee!).

Very excited to work with Matt, Mason and team! Read more at TechCrunch.

If you haven’t noticed yet, we use a standard Who, What, How, Why format to our funding blogposts….