Your Age is Irrelevant In Your Twenties

Ever notice how young people talk about their age versus the old? When we’re children, we always round up. “I’m almost 8″, or “I’ll turn eleven this year.” Then, around middle age, the verbs get indistinct . “I’ve just hit 40″, or “I’m past 50″. That’s understandable – once you’re an adult your age becomes a taboo, rather than a celebration. But have you ever noticed how in your twenties there’s no standard procedure? Your age doesn’t come up as much, if at all.

Until Marriage, You’re All The Same

I started noticing this effect while abroad in Barcelona at the tender age of 21. I partook in the usual expatriate behavior: partying, exploring the city, and generally being social with anyone who spoke my language. Everyone was excited and full of life – because they were as young as I was (or so I assumed.)  Imagine my surprise when I discovered my fellow playmates were 25, 28, even 31 years old! Turns out the opportunity to go live in Spain and take classes is just as appetizing for a 30 something as a 20 something. The lifestyle we were living was one familiar to any unmarried cosmopolitan around the world – it doesn’t matter how old you are as long as you can keep up with the nights.

Up until this point in my life, I spent time almost exclusively with people born within 18 months of me. In school, your friends are your grade. To associate with or date someone even one or two years ahead or behind was a spectacle worthy of school-wide gossip. I remember talking about 8th graders like they were a different species in middle school, and while the grade boundaries broke down slightly as we neared graduation, these arbitrary divisions were still the primary determinant of one’s social circle. After college, your age doesn’t matter – everyone is an adult.

Now I regularly spend time with people who are old enough to be my parents, if they had made some exceptionally poor life decisions 15 years ago. Imagine the scandal that would cause in high school! It’s still cause for gossip when the relationship is romantic, but somehow it doesn’t matter as much when you’re just friends. Yet I’m not hanging out with teenagers, so the gap still exists when I look down.

What brings about such a drastic shift of age range? I think it’s two things – the shift in activities, and the shift in maturity.

You Befriend People Doing What You’re Doing

 Your options in life are always limited by what you’re exposed to, and in school you’re only ever exposed to people very close to your age, due to classes and sports. In college the lines blur somewhat to include any other undergraduate, since you’re both on campus doing the same things  blur to any other college student. But the moment you choose to venture off campus into the world at large (or are forced to do so by graduation), the sky is the limit. It’s no longer how old you are, it’s what you’re interested in.

Whether it’s salsa classes, car modding, or  yoga, there’s a group of people out there you’re going to interact with once you dive in. And they don’t care how old you are – all they care about is how interested you are in the subject. You don’t have to talk about age related things like jobs or classes. Instead you can talk shop about the intricacies of some dance move, a sweet new racing stripe, or how to hold a warrior pose. The language of a craftsman is universal, as soon as you’re old enough to appreciate it.

(Who Are In The Same Stage of Life)

Therein lies the maturity aspect.  The difference between a 14 year old and a 15 year old is much greater than the difference between a 24 year old and 25 year old, even if the time differential is the same. When you’re young, your mind and body are developing at a rapid pace that makes it hard to connect with someone at a different stage. Activities change fast – from toys to sports to girls to drugs, or whatever it is for you. Once the 20s roll around development is essentially over, which means you can connect with anyone else. You’re just another adult talking with the grown ups.

Now the stages are much larger. I see only three left, after this current young bachelor stage: married, kids, and empty nesters. Once you enter those stages there’s no going back – you can’t live a freewheeling life once you’re chained at the hip to someone else, and that gets even more so once the kids come around. Then you’re back to associating with others of the same ilk, whether it’s at couples dinners or the kid’s soccer practice.

It sounds obvious when laid out like this, but for me it’s still a shock to be able to walk into a room and get treated as an equal by 30 somethings. I used to be the kid getting shouted off lawns, and now they care about my opinion? I sure don’t feel like a full fledged adult yet. But I also don’t want to be in the same place I am now in 15 years. Does that mean I’m just associating with the slackers and n’er-do-well’s of the last generation who never got the ‘Marry and have kids’ memo? No, I think I’m just finding the people who are super into the things I’m into. And sometimes I know more than they do about such subjects, which remains another shock, but one that makes sense. I’d hang out with someone younger if I thought I could learn from them.

I’m interested to see if others find this as noteworthy as I do. Do you notice the age gap in your social group lengthening, then contracting again once spouses and kids come into play? Is there another plateau later in life when the generations blur or coalesce further? I guess I’ll have to grow up and find out.

Weekly Review #63: Creative Manifestos, Hyrulean real estate, and SF street poop

I like 91-year-old Shimon Peres’ take on staying young: “Count the achievements in your life. Count the dreams in your brain. If the latter exceeds the former then you are young.”

Some creative manifestos: Bob Dylan told John Lennon in 1964 to stop writing shitty songs, which prompted him to start writing songs about things he cared about instead of what he thought would get to the top of the pops. A poignant reminder for any creative. And 99U reminds us that you can can have an easy life or an awesome one. They aren’t inclusive. Which will you choose?

Some nifty products: will tell you which sites are linking to yours, Inspectlet gives you an over-the-shoulder view of users interacting with your website, and Make a Gif lets anybody create .gifs easily. I’ve started using Wechat to communicate with my Chinese coworkers, and it’s hilarious – like Whatsapp with humor. For example, when you type ‘birthday’, the screen rains birthday cake emoticons. That’s just the beginning!

Startup-wise, Celebrate is an interesting concept – instead of robotically posting ‘Happy Birthday’ on friends’ Facebook walls, this app aggregates all the cool media relevant to the person throughout the year and then delivers them all at once. A touching gift, but then you miss out on the good stuff as it happens! And Horizon searches your personal network to find Airbnb or Couchsurfing hosts who are connected to you. I could see this going a step further – in dating, househunting, or job searching. Surely I could browse Linkedin companies by proximity of connection?!

In tech, Movoto’s journey to 20 million pageviews a month was an enlightening read – they looked at what kinds of online niches did a lot of linking, and then created content targeted at those niches. For example, nobody reads real estate blogs, but everyone links to video game blogs – so they wrote a piece on what fictional video game castles would be worth in real life. Bam – everyone links to it, fans get content, and Movoto gets pageviews.

This comprehensive post on how corporations are looking to startups for innovation reminds me that what’s hot in Silicon Valley takes a while to trickle outward. Cool to see how agile practices translate to big teams, though.

Here’s a reality check for you: app revenues surpassed those of Hollywood in 2014. Whoa. Those Clash of Clans coins add up.

In fun, Killer Queen Arcade is a 10 player boutique arcade game with multiple paths to victory. Nice to see arcade games are still being made. The #SelfieGame is a clever take on a modern trend – you take selfies and then players try to guess which emotion you’re conveying.

The Bold Italic bravely explains why there’s so much human feces on the streets of San Francisco, and wades into the ensuing debate about how to deal with homelessness. Man, this is such a complex problem. Amazing that it hasn’t been dealt with yet.

What I Wish I Knew When I Started My Job Hunt

After more than four months of the job hunt, I’m finally happily employed in a growth position at a small startup, just as I wished. It was a tumultuous ride, but a valuable one – it’s not often that you get to spend time sitting down with new smart people every week to get their help.  That said, when I started this journey I was going about it all wrong. Here’s what I wish I knew:

Online Applications are a Waste of Time

I started off checking all of the ‘cool tech’ job sites I knew – Linkedin postings, VC firm portfolios,, Hacker News jobs, Slack jobs, Product Hunt jobs, Growthhackers jobs,, and so forth. That introduced me to a whole lot of new companies and alerted me to job roles I wouldn’t have considered otherwise. I painstakingly tailored cover letters to the most appealing companies, sent off my applications, and – nothing happened.

Applying online is like adding your resume to the fat stack already on the hiring manager’s desk, except even worse, because they never even meet you and you’re a stranger from the internet. You’re essentially consigning yourself to obscurity by applying online.

Eventually I figured this out and used the posted jobs in order to prioritize my plan of attack. I’d target a company, browse Linkedin to find an introduction to someone at the company, and only after talking to someone in house would send in an application. That way, I’m either a referral who skips the resume pile entirely, or end up on the top with someone on the inside to vouch for me.

Networking is the Only Way to Go

If I did it all over again,  I’d start with my network rather than companies with openings. As the Bittorrent CMO told me, it should be more about which companies interest you within your network than which ones within your area have openings. I should have fleshed out my dream job first, and then aggressively networked in order to find connections with companies that matched that dream. Rather than trawling online postings, I’d meet with people in my network and ask them what companies they thought matched my wishlist and who they knew who could help.

It’s pretty easy in theory – just reach out to everyone you know in the industry and ask for a lunch or a quick phone call in order to get advice. I was consistently surprised with how responsive busy important people were to my young gun self. With few exceptions, a warm introduction will at least get you 15 minutes on the phone. Then it’s up to you to make the most of it.

Busy People Are Willing to Help

Once you know who you want to meet with, ask their contact in your network to connect you by email, not through Linkedin’s Introduction tool. I found that these invitations would often fall by the wayside, while the email inbox is just as easy and far more important. Tell your connection why you’d like to meet the person in question (“I’m interested in her job function and wanted to talk with her about how she got there” is simple enough), and let them do the rest. Usually they’ll acquiesce, you have a warm introduction, and now all have to do is find a time to meet. In person is best, but sometimes you’ll have to settle for a call.

Come prepared. Do research on the company and the person (Twitter is invaluable here) so that you can ask informed questions rather than easily Googlable ones. Treat them like a human, and show that they’re not just a means to an end. As my search wore on, I found myself asking more direct, specific questions here, rather than macro inquiries like where the market is going. How they ended up at this company and what they think you could do to do the same are more important.

Just make sure to end on an actionable note. Help them help you. Whether it’s another introduction, a referral, or feedback on how to approach the application, give them a next step. Then afterwards send them an email summarizing your notes and how you plan to execute their advice. This accomplishes a few things – it shows you paid attention, that you’re taking their advice, and as a reminder to do what you asked them to. Then connect on Linkedin and let sit. You’ve made an impression in person, tracked it in their inbox, and shouldn’t pester them any more until you have something new to say.

Cold Emails are Invaluable

Sometimes you don’t have any connections with the person, or your desired introducer doesn’t get back to you. At this point, don’t hesitate to pull out the cold email. This is another big thing I wish I had known – cold emails are far more powerful than any other job-related task you can do online. There were times when I had already been rejected online, but managed to get an interview anyways because I had emailed the CEO and he forwarded it to some lackey who then treated my application as an order from above. It shows daring, resourcefulness, and initiative. Done right, the cold email can do nothing but good for you.

To find their email, use This site was a godsend during my search and continues to be helpful. It tells you if a given email address is valid, which lets you guess email combinations until you find one that works. Oftentimes the big guys’ emails are nothing more that or (Sometimes Mailtester says that the domain does not accept verification, but most times I’ve found that my best guess works anyways, so don’t be dissuaded.)

As for the email itself, there are differing guides on this (Noah Kagan’s and Scott Britton’s are good starters) but for me, it’s got 3 parts: the hook introduction, your value proposition, and an action step. It should be as short as possible, with neat formatting.

I start cold emails with ‘You are’, which grabs anyone’s attention when personalized. You are an inspiration to me, I’ve enjoyed this blog post of yours, etc. Don’t lay it on too thick, but be sure to tie yourself to them in some way or another, be it through their work, a shared connection, or some other mutual hobby. If you’re bold, you can use the name of a mutual Linkedin connection without asking them for an intro first. (I’ll admit I did this when some contacts never got back to me, worked like a charm.)

Then explain why you’re emailing them. Why them in particular? What value do you bring to the table? The more specific your advice wanted is to them, the better. Most busy people get hundreds of ‘grab a coffee and pick your brain’ requests a day, so don’t be one of them. Ask for something specific, just like the actionable note from earlier. Your best case is an in person meeting, but an introduction or shunt to another lackey is also valuable.

With cold emails, it’s all about being a kindly brontosaurus: polite yet immovable. If they don’t respond within two weeks, send another email following up to make sure they got it. Gently push until you get a response – the worst that can happen is a ‘no’. Remember that these people don’t care about you – you’re a stranger from the internet. A cold email that shows why they should care coupled with gentle pressure remedies that, but only with persistence.

Track Progress Like It’s a Sales Funnel

Now you’re meeting with people regularly and slowly getting closer to a desired company, or a sense of one. Great! Now the trick is to keep track of it all. Much like a salesman, you are juggling many relationships relationships in different stages towards specific goals. You need a place to keep track of it all, and Salesforce isn’t going to be quite as helpful for you.

I kept track of all the company openings, warm connections, meetings, and weekly accomplishments in one big Google doc, but in retrospect I wish I had structured it more around people. Instead of a big list of company openings, it’d be better to have a short list of desired companies, with the people who could get you closer to them grouped underneath. Then you track where each person is in the cycle – emailed, met, or needs following up. Otherwise you might make moves towards a person only to have them fall through the cracks.

Ian Adams of the Senator Club was so dedicated that he built a special Excel file of his contacts, but whatever system works for you as long as nobody falls into the cracks. What’s important is that you don’t let people fall out of contact, even after you have already met with them. Nailing the follow up is as important as nailing the introduction. Let them know how things have moved forward since last you spoke, and how your advice was helpful. That way you’re nurturing an actual relationship, instead of a one-off meeting.

As it turns out, creating and nurturing real relationships are things I should be doing no matter how employed I am. There’s nothing about the end of the job hunt that means I should stop cold emailing people I admire to get their advice. Now I just need to come up with an ask more involved than ‘get me a job’…

Weekly Review #62: AI assistants, effective #contentstrategy, and the death of email?

OMG Meiyu is a Youtube channel where a perky blonde American woman with pitch perfect Chinese teaches Mandarin speaking youth about American slang, leading to hilarious spurts of English between torrents of Chinese. Her channel doing the reverse English to Chinese lessons is less mesmerizing but way more educational.

Startups include Tenderfoot, which keeps you in touch with acquaintances met while traveling, and Clara, an AI personal assistant that schedules meetings for you via email just like a secretary. At 600$ a month, though! Surely we’re closer to the Singularity than that…

This Ancient Viking Chess Game is apparently a favorite of war strategists the world over – it’s asymmetrical, with one player starting outnumbered in the middle of the board bent on escape and the other on blocking him.

Sahil Lavinga of Gumroad offers advice on keeping a company flat - ‘it’s all about achieving trust and clarity without bureaucracy’. Belle Cooper’s must have iOS apps of 2014 is a cool rundown of many apps I had never heard of before. And Nathaniel Ellison spells out Why News is a Waste of Your Time far better than the nascent blog post I had in my head ever could – I dare you to prove him wrong!

Great case study on app marketing from an interview with Tamara Steffens of Acompli fame- she offers countless priceless insights on the marketer/developer/user feedback loop and on getting the word out. Seriously, this article is insanely helpful.

Speaking of marketing, Citibank’s clever #incredouble campaign crowdsources ridiculously photogenic activity combinations and then hires youtube star DevinSuperTramp to film them. They get marketing, Devin gets work, and we get wrecking ball pinatas! Win-win-win.

Then we have some great resources on content marketing4 fundamental blogging tips from a former Buffer writer, and a rundown of 40 highly shared company blog posts from 2014.

The Verge claims that Slack is killing email, and shows some serious stats to back it up. The founder makes a point that most email today is from people we barely know, or marketing automation services, so why not makes high touch inter-office communication more like instant messaging? Sure, that works for small millennial companies, but what about the enterprise grey hairs? Email is immortal in my mind – though it is certainly in need of supplanting for certain communication needs.

Then there’s Yuri Milner, a Russian billionaire who only invests in surefire late stage companies in order to 10x his million dollar investments. Now there’s an interesting strategy!

The Achiever’s Argument Against Travel

Image from Trey Ratcliff on Flickr

I’m a big fan of travel. After living in Barcelona for a year during college and solo backpacking through almost every country in Europe, it’s safe to say I caught the travel bug pretty hard. Hopefully my Matador Network Portfolio conveys my positive stance on travel as the best way to discover where your identity fits in the world, gain perspective about disparate lifestyles, and have a blast while making the most out of the limited time you have on this planet. My time spent vagabonding (taking time off from normal like to travel for the sake of travel) introduced me to new experiences and perspectives that remain a formative part of me today. However, once you have an idea of what you want to do with yourself, traveling ceases being exciting and exploratory and merely becomes a distraction.

We are all preoccupied with finding meaning in our lives, and while travel is arguably the best way to find it, it’s not a good way to develop it. The itinerant backpackers lifestyle is inherently consumptive rather than creative. It is the best possible kind of consumption, such that it is almost incomparable to the consumptive lifestyle of a couch potato, but the fact remains that most travelers take more than they give to the place they visit.

Instead, they soak up the exotic surroundings, novel experiences, and rotating casts of characters like a video game with them as the protagonist. I did it, my hostel mates did it, and the millions of young backpackers currently crisscrossing the world are doing it as you read this. I notice it more when I’m a local – these exciting new characters enter your life for a few days or a week at most, only to drop out again afterwards. The first few are exciting, but after developing a few relationships that get cut off abruptly, you start to get jaded and stick to spending time with people who will still be around next month. Such interactions are fun, but lack depth or meaning.

How you find meaning in your life will vary. I can only speak for what has worked best for me. So far I’ve gotten the most out of the creation of value for others and fulfilling personal relationships. Neither of these are found on the road. 

Nobody Cares About Your Trip Except You

Near the end of the 3 months I spent living out of a backpack and jumping on whichever bus went east, I got jaded. I had gotten so used to new things happening to me all the time that it was no longer exciting. I started wanting to make things happen to the world instead.

After all those months, people, and experiences, what do I have to show? I’m certainly more worldly, experienced, and open-minded, but the hard truth is that nobody else cares. Think about the stranger at a party who walks up and says they’ve been traveling for a year. How interested are you to hear about that? It’s merely fodder for the next conversation or two. Unless this stranger mentions somewhere you’re planning to go, your interest is no more involved than it would be when prompted with ‘I work in theatre’, or ‘I visited my uncle in Canada last week’.

Compare this response to the stranger who walks up with something they’ve created, whether it’s art, business, or something else. No matter how relevant the creation is to your interests, you’re going to want to know more. For instance, just the other day I met someone who published an open-source the Bible rewritten so that all male characters were female and vice versa (to provide female Christian role models, since all the women in the original Bible were slaves or whores, sadly). I’m about as far from Christian as you can get, but that guy was damn interesting!

When I introduce myself as the author of a book on group games I’m bombarded with stories of their favorite games or questions about the self-publishing/Kickstarter process. These are constructive experiences I can use to teach others, learn from their experience, and ultimately create better stuff. Compare that to one of my best travel anecdotes –  the time I showed up to my Couchhost in Russia only to find that my bed was a pile of coats amidst 40 other commune members.  I can’t do much with it other than entertain.

Travel Relationships Are Of Convenience, not Compatibility

I’ve written plenty about travel’s transitory nature of relationships already. While you can and do meet fun ersatz characters on the road, most of the people you spend time with are shallow hostel friends focused on partying, or locals happened upon  in the street and bars. There are a few diamonds in the rough there, but most interesting people are busy leading their lives, not waiting around to entertain some ragamuffin.

The best example of this I’ve see was in Mexico City, where the people on the streets downtown almost belong to a foreign culture than those who live in suburban houses. Think about living in an American suburb – how often do you spend time with the people you’d run into on streets downtown? The middle class locals I met through Couchsurfing admitted that they had never ridden the metro – a fact I found astounding at first, until I realized how many times I’ve had my parents drive me to the SFO airport rather than take Caltrain.

You generally don’t meet the mover-shakers or the interesting people while traveling because they’re all too busy living. Instead you meet fellow travelers, locals with nothing better to do, and if you’re lucky, a few kind Couchhosts with the time and energy to spend on strangers they’ll likely never see again. Again, I have been one of those locals giving up my couch to foreigners every week, but I got tired of meeting people I’d never see again whose only reason for being in my life was the need for a place to stay. I’m way more selective about the Americans I choose to spend time with – why should they be any different.

Even the Best Travel Friends Become Long Distance Relationships

Plus, even best friends found abroad all become long distance relationships. We all know how well romantic LDRs work out. Personally I’ve never heard of a success story, barring those on the verge of marriage separated by grad school. If the romantic passion of lovers can’t hold strong across national borders, what makes you think you’ll stay in touch with those charming Canadians you drove across Spain with?

No, at best you’ll Like their stuff on social networks sporadically, but unless you can maintain Skype dates every weekend you’re not going to have much of an ongoing relationship. Some of the favorite people I’ve met in my life live abroad, and I don’t interact with them much beyond sending internet links that remind me of them. We’re both too busy living our own lives with people on our own continents to devote time to those elsewhere. That’s not say we don’t jump at the chance to see each other whenever we’re anywhere near the same time zone, just a simple truth that there’s no substitute for face-to-face.

Creation Trumps Consumption, and It’s Best Done Stationary

So, yes, everyone on Earth is a special snowflake with their own story to tell, and yes, traveling is fun and good for your mental compass. But given the choice, I’d rather use what time I have to connect deeper with the snowflakes who inspire me to be a better person rather than those who simply are new and different. And I’d rather work on creating things of value to others (which is also fun!) than focus on travel experiences that benefit nobody beyond myself. That’s much easier to do when you don’t have to worry about where you’re sleeping tomorrow.

But don’t take it from me – look at the REAL travelers. The people who have lived nomadically for years; who have made livings off of sharing exotic experiences. All of them eventually settle down to create something or develop relationships. From Nomadic Matt‘s seminal post on why he’s quitting travel to Tynan’s leaving behind the Life Nomadic in order to build a blogging platform, to Rolf Potts, who literally wrote the book on Vagabonding, halfway settling in Paris to teach writing workshops.

These men had all built their identities around being a traveler, and later independently decided that that life wasn’t for them anymore. That’s not to say they’ve gone cold turkey. Look at their blogs and you’ll see that they still travel for short stretches, mostly with good friends. That way their life affords ample time for creation, while using sporadic travel as a fresh perspective as well as a chance to spend more time with humans they want to have lifelong relationships with.

If such worldly and renowned travelers as these have come upon the same conclusion, who am I to disagree?

Once You Know What to Do, Live At The Hub

I plan to travel sporadically in a similar manner later on, but for now I’m focused on amassing skills and resources in the hottest startup place in the world. Your self actualization HQ will differ, but for techie me, there’s no contest. It’s all about San Francisco. My life direction discovered on the road has consistently led me to startup marketing,which is just what I’m doing, in the world startup capital.

The smartest people from around the world are coming here to make things happen – every week here I meet people from every corner of the world who have come here to affect serious impact, whether through companies of their own or working with powerful global agencies. It’s intoxicating – everyone at these parties is the stranger who has created something! My conversations with them leave us both thinking, questioning, and growing personally for days afterward, which certainly doesn’t happen with any conversation I’ve had in a hostel.

So for now, I’ll be one of those hapless locals who I used to ridicule for not exploring the wide world. Though I should re-iterate: if you don’t have a life direction, travel as a vagabond. There’s no better way to live to your utmost while finding out your place in the world. As for me, I’m got a decent ideas of what that place is, both figuratively and literally.

I’m confident I’m chosen well. On that same Russia trip where I slept on coats in a commune, I remember introducing myself as hailing from Silicon Valley, and got this wide-eyed response: ’I know that place – you are taking our best minds!’

You said it, babushka, not me.