Gmail Catches My Mistakes

I was just writing an email and hastily cc’d the wrong person. Gmail uses machine learning to understand my common behavior and alerts when they think I might have made a mistake. Its awesome

1. Auto-populate my contacts (which are automated via frequency)

2. Recognizes my mistake

3. Enabled me to easily correct my mistake with one click

Saved me from emailing the wrong person. Impressive.

Why I Write.

I started writing because people told me it was beneficial to cultivate an online presence with a blog. At first, blogging felt like work. But the more I wrote the more I began to enjoy it and recognize its incredible benefits.

 Now I write every single day. I usually try to follow aspects of the artists way and write as soon as I wake up as well as just before I go to sleep. When I feel like others can derive value from what I write, I publish it on my blog. It typically ends up being a 50-50 split between what I choose to publish vs. file away internally. Ironically, maintaining a blog is now merely a positive externality of something I enjoy.  

The reason I have grown to love writing is because I’ve found that it inspires an exploratory thought process thats effectiveness is hard to emulate anywhere else. Writing forces me to really think, organize my thoughts, and ask difficult questions. In the process, I find myself riffing on thoughts I may have never encountered or considered questioning. I consider the exploratory thought process writing provokes akin to the serendipitous experience of browsing the web. As we start to explore, we see things that interest us along the way. We end up wondering down a path of discovery not sure how we got there, but often happy that we did. In both cases, the process facilitates serendipitous discovery taking the form of new learnings, thoughts, and understanding. 

 In my own life, habitual writing has inspired new ideas, direction, questions, insight, and clarity. In an environment increasingly characterized by digital stimulation and immediate gratification, this has helped me to distance myself from reactionary habits and live more intentionally.

 I highly recommend writing everyday for an entire week if you’ve never tried. Then of course, reflecting and writing whether there was any value there.

Building Online Communities, Content, and Purchasing Decisions

A loyal online community is one of the hardest assets to cultivate, but often one of the most valuable. Unlike one-off click-throughs, members of a community engage in an on-going relationship. Depending on the context, their value comes through in the form of support, input, awareness, data, SEO, repeat purchases…the list goes on.

Consistently publishing high-quality content is one way to cultivate an online community. Fred Wilson’s blog AVC is a perfect example of this. By churning out value on a daily basis he has cultivated a loyal community. Make no mistake, building this community is the product of lots of hard work; regularly publishing thought-provoking posts and accomplishing the things he has as an investor and community leader is no easy task. But his publishing labor does bare fruit. You need to look no further than the hundreds of comments on each post, AVC meetups around the world, and the composition of every entrepreneurs twitter followers to get the sense that Union Square Ventures is privy to some of the most exciting investment opportunities out there. The AVC community and their network effects certainly contributes to this.

Fred’s blog in the context of the entrepreneurial eco-system demonstrates how content can affect markets. In the case above, the brand is Union Square Ventures and the consumers are the entrepreneurs. The top entrepreneurs are looking to exchange equity with investors who they believe will provide the most strategic value (and best/fair terms). VC’s want to invest in the most explosive opportunities and the best entrepreneurs. In the most explosive investment opportunities, entrepreneurs have options. Their purchasing decisions take the form of determining which venture fund they’d like to trade equity for cash with to build their business. It seems that many of the top entrepreneurs want to purchase USV.

The main point I want to drive home here is that content drives purchasing decisions. Assuming that products are equal, consistent publishers of high-quality content can gain a competitive advantage. This is by no means meant to take away from the fantastic team and track record of USV. They have rightfully earned and deserve every skin on their wall. Rather it’s to demonstrate a market dynamic that holds true across verticals whether we’re talking golf balls or venture funding. The bottom line is content can drive purchasing decisions. Note that “content” can take the form of videos, photos, social media, etc.

Let’s shift the discussion to what we more traditionally think of when we hear brands like retail, online services, etc. One of the many reasons that brands have become publishers is due to the dynamic above: content can create communities that provide engagement and drive purchasing decisions. Just as this dynamic straddles verticals, so does the winning combination: brands must strive to publish original, high-quality content on a consistent basis.

But brands face a much more challenging publishing eco-system than venture capitalists. Their are more players in the space, a higher frequency of purchasing decisions, and greater distribution across multiple channels (web, video, social). Many brands have the resources to compete in this eco-system, but not all do. Producing high-quality content at scale is difficult and often expensive. Some look to hire more people to mitigate their output difficultites. Unfortunately, this is not a scalable nor inexpensive solution. Its simply a horizontal move that will again need to be readjusted as the demand and content eco-system continue to grow. Further adoption of smart mobile devices and real-time social platforms will fuel this. Are you as excited about the additional noise as I am?

A more scalable option is to make the publishing process more efficient. Automated content platforms have existed for awhile, but they lack any semblance of originality or brand curation. Cookie cutter solutions do not effectively build sustainable communities. Their audiences quickly become desensitized and relegate the content to noise.

Where am I going with this? Mainly, I think there are opportunities for companies that facilitate the ability for brands to efficiently publish high-quality content at scale. The ideal blend will most likely offer a mix of original and automated content. Brands will have the ability to quickly curate and offer a layer of originality on top of automated solutions in order to accommodate the necessary scale while avoiding the appearance of cookie cutter content. There are a couple of companies working on these type of solutions and I’m anxious to see how they do.


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Product Design: The Inevitability of Noise

My biggest problem with my Facebook newsfeed has always been that so much of the content is irrelevant. This is mainly due to the fact that many people I’m friends with I’ve only met once or haven’t seen in a long time. So I acknowledge that the noise is somewhat my own fault.
I made a friend request the other day on Facebook and was presented with an option I hadn’t seen before. I took a picture of it below:


Product Design

If you haven’t noticed, Facebook implemented a smart lists feature. Now each time I make a friend request, it prompts me to assign new friends to one of these lists.
I started thinking about it and realized that the more engaged I become on platforms and applications, the more noise I experience. This holds true on Twitter, Quora, Gmail, Evernote, and even Google Docs. Almost all of these applications try to mitigate the noise by providing filters. Where most of them fall short is the friction accompanied with applying these filters.

Why this new Facebook feature is so clever is that it prompts me to apply this filter within my existing workflow. Each time I want to add a friend I’m always going to click the Add Friend button. I’d never create my own groups and then manually segment my friend graph. I just don’t perceive a high enough ROI on my time. Yet, if one simple click after an action I’m already taking means that I can stay more organized I’m happy to do it. In short, they’ve made the filtering process as frictionless as possible by automatically creating “buckets” and prompting me to segment new friends into them without having to think.

The take-away here is that mechanisms that are aimed to improve the signal to noise on applications should be integrated into our existing workflows. Just because you provide a mechanism to stay organized does not mean people are going to use it. This requires extra work and often teaching users a new behavior. People need to have their hand held and Facebook has done a fantastic job of this throughout the lifecycle of their product.

My First “Hitenism”

I met Hiten Shah at the Lean Startup Machine in New York City. He was a mentor there so throughout the weekend my team had a chance to interact with him. Overall, he made a strong impression on me as a really bright, cool guy. So when I came across his newsletter “Hitenisms” I was intrigued and decided to subscribe. This morning I received my first one in my inbox:

I love those who can smile in trouble, who can gather strengthfrom distress, and grow brave by reflection. ‘Tis the business oflittle minds to shrink, but they whose heart is firm, and whoseconscience approves their conduct, will pursue their principlesunto death.” – Thomas Paine

Life has a funny way of acting normal most of the time, and thenone morning you wake up, and the ish hits the fan.

If you run your own company, this happens more and more often asyou grow, and bump up against competitors, naysayers, patenttrolls, and other awesome varieties of troublemakers.

Anyone who tells you that this doesn’t totally suck and make you want to question life sometimes either hasn’t been at it longenough to dole out advice, or is completely bullshitting you.

The reality of running your own business isn’t as glamorous as itis made out to be; for starters, there are tons of highs and lows,and also a heaping amount of uncertainty—even when you’re doing well.

However, I promise there is a silver lining in all of this.

As it turns out, you do actually have a choice about how to dealwith all of these experiences as an entrepreneur, and here it is:smile or die.

It may not seem like a choice—slap a grin on your face orperish—but there is actually an element of choice involved.

You see, you’re always going to have more obstacles in your paththan you care to have; some will be seemingly insurmountable, butyou overcome them and feel stronger for it. Then there are the onesthat rock your world and threaten to throw you off course for aperiod of time.

So, where’s the choice?

Well, in how you handle those obstacles.

Do you learn from your mistakes and make sure they never happenagain, or do you ignore the problem and hope it goes away quietly(hint: it never does)?

True power as an entrepreneur comes not in having a perfect trackrecord—it comes from effing it all up to the point of no return,then quietly reflecting and coming back with a smile on your face,happy that you’re getting a second shot.

I really liked this. Something I’ve learned which this email manifests is that we cannot let the situations we find ourselves in define us. Rather, its how we react to those situations that speaks volumes about who we are. We’re going to find ourselves in messy situations no matter how great of decision makers we are. As Hiten points out, this is especially the case as an entrepreneur. Instead of focusing on this mess, which in many cases is shaped by things completely out of our control, I’ve found it more effective to channel my energy towards my reactions/next steps. In alignment, I’ll try to attach my introspective assessments to these reactions instead of the “state of things” which can often be pretty rocky.

Hopefully, Hiten’s thoughts provide value to those reading this.


Customer Loyalty: Missed Opportunity at the Cash Register

After I made a purchase yesterday the cashier asked me for my email address. For the sake of my inbox sanity I respectfully declined. In alignment with my moleskin diet, I thought about this interaction for a good 15 minutes. It got me thinking, what is the conversion rate on this question and the roi on each email address?

Lets compare this with if she asked me for my twitter handle. Knowing that I’d have to opt-in to receive updates from the brand, I’d be cool with giving that away. Don’t kid yourself, we all want more followers.

Brands can derive a ton of value from their customers’ twitter handles. For starters, by following someone they’re potentially giving them a subtle nudge to follow them back along two touch-points: a new follower notification in their inbox and the chance that they happen to notice their avatar on the followers section of their twitter dashboard. The value of a twitter follower for a brand is non-debatable.

But even if a customer doesn’t follow them back there is a ton of value brands can capture. A few sources of value and ideas from a customer loyalty standpoint:

-Target their customers at a very granular level
-Gain a better understanding of their customer base via social profiles
-Monitor customer conversation and sentiment
-Determine influencers of their customer base
-Obtain location data via foursquare check-ins published on twitter
-Manually push deals to people who have checked-in nearby via @ mentions
-Identify and reward brand evangelists

Bottom line is their is a treasure trove of data here for any brand. Obtaining this data is certainly better than coming home empty-handed. At this point in time, it’s hard for me to argue that a twitter handle is more valuable than an email address. After all, email is asynchronous (tweets are ephemeral), provides conversion benchmarks, and offers a richer medium for advertising creative. Still, brands can take ground.

I think an interesting strategy to test this would be if cashiers requested an email first and then maybe a twitter handle if customers declined. I believe this qualifies as an elseif statement…

if (get_email) {
} elseif (get_twitter_handle) {
} else {

Actually Follow Through

One thing that I love about the New York Tech Community is everyone is so willing to offer help. Its almost as if “let me know if I can help you out” is a standardized signature on emails. The problem with this is few people ever follow through unless there is an explicit ask. This is why people that take the initiative to follow through by really providing help standout.

For starters, if you have any type of relationship with someone or understanding of their situation, you can typically make an intelligent guess how you can help them out. If they’re building a product, actually use it and provide candid feedback. If they’re fundraising, introduce them to investors who specialize in their space. It’s not rocket science. It’s just taking a genuine interest in their success. Far too many people never follow through or wait for the explicit ask to actually do these things. Stop waiting. 

Over the course of building Sfter, I sent the an alpha invite to a founder of a booming, growth stage company with a simple “would love to hear your thoughts” at the end of the invite. He responded in typical fashion with a “thank you, I’ll definitely check it out.” I didn’t expect anything. He was a busy guy and I’d become de-sensitized to the “I’ll let you know what I think” after so many people failed to do so. For the record, I’m sure I’ve done this many times and apologize for those instances.

The next day, I had a three paragraph email from him with some amazing feedback and 2 attached screenshots indicating how the product could be improved. I was blown away that he’d taken the time to really think about my product and how it could be improved.

The point is that the job isn’t done after you’ve offered to help. If you really want to stand out, follow through on those offerings and even take the initiative when there’s not an explicit ask. Demonstrating an authentic interest in someone else’s success goes a long way and pays dividends.