Weekly Review #50: Prison Startups, Beautiful ‘Hire Me Please’ pages, and unflippable rafts

I spent some time at Powder Mountain, home to the Summit Series, this weekend. Pretty crazy to see how far this young team’s dream has come along – they paid for the first event out of pocket, and now they raised $40 million to buy an entire mountain. Now they’re developing the on site ski resort and curating invite only retreats for tastemakers and creatives. I love the vision, but from talking with the employees, Utah is pretty lacking in most innovative departments most of the time, which means I doubt they can create anything truly permanent. Great weekend retreat locale, though.

Unmistakable Creative’s interview with Frederick Hutson about founding a venture funded startup after 4 years in prison was inspiring on many levels. He touched on many of the same subjects vanilla entrepreneurs do, but he conveys them in a much cleaner, down to earth manner. Like:

  • Solve the problems you already enjoy working with
  • Don’t put any energy into things you cannot control (like race relations in prison, they’d apologize profusely if they accidentally bumped into someone else in line, because otherwise the entire ethnicity gets mad at you)
  • Situations aren’t good or bad – they’re just there. It’s up to you to figure out what to do with them.
  • Life is about balancing what you know with how you feel. You feel tired, angry, or loving, which can butt what you know is the best decision. But you need to acknowledge your emotions as well.

The New Yorker has a great piece on Drones and Everything After, examining how the little flyers have changed recreation and filming with dash of military use. Check out all the embedded footage for some real gems.

I’ve wanted something like Hemingwrite for years – a simple analog keyboard that syncs your writing to my butt but offers zero distraction and doesn’t require Wifi. Man if it isn’t the most hipster thing ever, though.

Tradecraft tells us how to ace a job interview: Research the company, Solve their problems, and Treat them like a human. Easy.

FlorianIsAllIn.com is one example among many of beautiful hiring landing pages created by job seekers to woo their dream employer. Reminds me of Alice Lee’s old Instagram love letter.

Only one startup this week: Photojojo rents out the expensive fun camera creative stuff in short chunks so your next creative endeavor doesn’t have to destroy your wallet.

Resources: Unbounce walks us through how to make a truly viral ebook landing page using existing tools, and Buzzsumo lets you see which articles have the most shares and views around certain keywords.

Fun stuff : Creature Craft Rafts, which are shaped like dragon heads and thus are impossible to flip, and What Would I Say, which generates FB status for you after analyzing your existing text.

The Dealmaker/Dealbreaker List To Determine Compatibility

Image from andilicious on Flickr

I was talking with my friends recently about what what it takes for a marriage to succeed. As the conversation went on, it become clear that the same principles that make a marriage work are what makes any healthy relationship work. Given that your ideal life partner should also be a best friend, the reasons you chose them should be the same reasons you choose your friends, your housemates, and anybody else you choose to spend time with.

We all have friends that we could never live with, and housemates that we would never even be interested in marrying, even if we get along with them just fine. In each of these relationships, the involved parties require certain criteria to be met, but what you look for in a friend obviously isn’t exactly what you look for in a wife.

Speaking personally, I choose my friends based of our personal chemistry and the interests we share. Then we can spend time together indulging in said interests, to the benefit of all. True, sometimes the interest supersedes the chemistry (for instance, I’ve had sports teammates who I wouldn’t ever see outside of practice, and nerdy video game partners who I only ever saw while next to a screen), but an ideal friend would have just as much fun doing both with me, because they’re things we’d do regardless.

That said, I’m not a total mercenary with my activity partners. Hanging out with someone just to fill out a sports team is lame, and if our chemistry is completely at odds then both are better off avoiding each other. Just as with marriage or cohabitation, friendships require certain fundamental agreements.

I call these Dealmakers and Dealbreakers – a list of must-haves and must-not-haves for any relationship. The list becomes more stringent as you move up the ladder of commitment: I’ll be more picky choosing my wife than a girlfriend, than a roommate, than a drinking partner. But each relationship has its own prerequisites, built on top of the criteria below it. Your list will differ from mine, but as an example, here’s a slipshod version of my own list (I haven’t ever written it down, but it doesn’t require much thought):


  • Dealmakers: Jovial, curious, and playful
  • Dealbreakers: Emotionally unstable, untrustworthy, deceptive.
  • Other: Outside of this list, we can differ all over the board (all the better, for diversity and new experiences), but if they don’t fit these rules we’re unlikely to enjoy each others company.

Living Partners

  • Dealmakers: Okay with my living space being messy, don’t mind me hosting friends for dinner or drinks
  • Dealbreakers: Steal my possessions, make me feel unsafe in my own house.
  • Other: I don’t care if the sink is always full – as long as I can find a dish that’s moot. Yet some housemates require their kitchens to be fastidiously clean, in which case I can wash my stuff along with the best of them. Since it’s not on my dealbreaker/dealmaker list, I can be flexible around the lists of my partners.

Spouse (under construction)

  • Dealmakers: Spunky, confident, ambitious (if I subscribe to GoodGuySwag’s Wife List, there’s a lot more)
  • Dealbreakers: Needy, acts like a princess.
  • Other: This is based off of the romantic relationships I’ve had so far – they’ve all ended because one of us eventually found a dealbreaker in the other. As frustrating as it was at the time, now they’re great examples that have taught each of us what we will and will not put up with. (Related: WaitButWhy on Picking a Life Partner)

Every friend, housemate, and significant other you have refines your Dealmaker/Dealbreaker list. It’s an iterative process, culminating in a perfectly accurate list that lets you impeccably sort out the makers from the breaker.

Everything not on either participants’ list is moot. They’re not relevant to your compatibility – just extras that spice up the game. They may be drastic differences of opinion or lifestyle, but as long as they’re not on either person’s list, you’re good. I’ve had great friends with completely disparate cultures, religions, beliefs, and lifestyle choices from my own, who’ve all taught me great stuff. Since we didn’t differ on any dealbreakers, the differences only served to make the relationship more interesting. We learned from each other.

If you don’t know what your list entails, (hopefully you do by now) then you run the risk of the relationships falling apart due to something the other person does that you can’t stand, or you ending it because they lack something you’ve decided you need.

What’s on your Dealmaker/Dealbreaker list?

PS: My mother notes that as relationship goes on, a new aspect comes into play – shared history. She’s been with Dad for decades, and raised kids with him, which becomes a powerful force for staying together as the shared memories multiply. She may have found new annoyances in his manner with age (I’ve seen a few of them myself), but even if they border on dealbreaker territory, there’s the entire life of shared history to keep things going. They know each other too well.

That doesn’t come into play at the start of a new relationship, but it certainly does with time, and is something to consider alongside the DM/DB list. Is this someone I want to have shared memories with? It’s the past tense version of the decision you’re about to make – is this someone who I want to spend time with? If they have the makers without the breakers, I’ll bet it is.

Weekly Review #49: Scratching the itch to create, @averylewis on conveying passion, and silly drones

I sat down with Avery Lewis for more job hunt advice, who was Getaround early Head of Product and now runs the powerhouse development team Collective Ray. A classic hustler only 2 years ahead of me, here’s what he said:

  • It’s all about hanging out with people you admire who are doing things you’re passionate about. Tell them about your passion for the team and their mission first, and have all the classical resume stuff on hand to back it up
  • When interviewing, talk about cool stuff you both like and then you’re just friends having a conversation
  • Be strategic in presenting yourself – look at their mission and tailor yourself to fit in to it
  • Push back gently with questions – ask them about the job beyond the description before interviewing to see if there’s a good fit
  • Know what you want, what they want, and how you can give it to them

Brian Chesky of Airbnb talks about scratching the itch to create in NYT:

  • “ I found (my identity) through industrial design. I think it helped me become a good C.E.O. because it really teaches you empathy. It’s like method acting; you have to put yourself in someone else’s shoes. It’s very easy for C.E.O.s to become transactional and focus on numbers and quantitative analysis, and that can create an emotional detachment. Industrial design teaches you exactly the opposite.”
  • “I removed all reticence whenever a crisis occurred, and I made a unilateral decision to be direct. And when I started doing that, I realized that people are thriving from this, and that it’s so much more helpful for people.”
  • “(When hiring), we’re looking for people who see the world as it could be rather than as it is. I also ask people to summarize their life in three minutes. I’m trying to figure out the formative decisions and experiences that influenced who you are as a person. Once I figure that out, I’m trying to understand the two or three most remarkable things you’ve ever done in your life. Because if you’ve never done anything remarkable in your life until this point, you probably never will.”
  • “Don’t listen to your parents for career advice. Assume whatever you do will be a massive failure, because then you’ll figure out what you want to do regardless of the consequences”

Ramit Sethi on the Tim Ferriss Podcast was a great two hours

  • Persistence is important for entrepreneurs because sometimes staying in the game longer than others is all it takes to win
  • It’s hard to get to the top, but easy to stay there (because everyone emails you cool stuff)
  • Ramit structures his company so that if any person in it got hit by a bus, they’d have reproducible systems down on paper so that anyone else could do their job the next day
  • When cold emailing, find a casual commonality, then talk about why you follow them, and end with a specific response desired (but flexible)

Clay Shirky has a long, rather technical essay from 2003 detailing the challenges of forging online communities, but it’s worthy stuff, and all the more relevant for today’s social media companies.

Redfin CEO Glenn Kelman preaches to 22 year olds, saying the happiest people he know have a craft and a calling, you should try to do as much as possible rather than see as much as possible, and concludes that the only way to be happy is to be needed by others (which doesn’t come from traveling).

Startups this week include Cameo, which makes it easy to create beautiful videos on your iPhone (kind of like Gopro’s 10 app), Pigeon, a tiny orange minimalist kick scooter, and Mosey, which allows users to curate worthy walks in any city.

Some fun with drones: Spotify put a subwoofer on one and is flying is around music festivals, and this guy programmed his to walk his dog.

Relationships Are Priceless Transactions


Arturo was a smart guy. He didn’t have many teeth left, but he eyes were bright and quick, his collared shirt clean and pressed, and his pantomimes of art history happenings more exuberant than anything I’d ever done sober. We had run into him at a museum in Mexico City, and he proceeded to walk us through every single aspect of Diego Riviera’s intricate murals. Our encounter encompassed almost two hours, 5 murals, and several conversations about both parties’ personal lives.

When it came time for us to leave, I held my breath and braced myself for the supplication that had been a foregone conclusion in the back of my mind from the moment Arturo started talking: “How much money is he going to ask us for in return?”

Thankfully, it never came. Arturo bid us goodbye with nothing more than a smile and a wave, and my faith in humanity was restored ever so slightly.

Yet the encounter remains poisoned in my memory due to the  suspicion I had harbored during the whole exchange. I expected him to demand money from us  because he had shared his time and knowledge with us, because he didn’t look well-off, and because, well, this was Mexico. Western travelers are used to shrugging off persistent pleas for alms or purchases at the numerous tchotchke shacks that line every tourist attraction in the developing world. It’s easy to shrug off the fusillade of begging when presented at you all at once, and as long as you speak firmly and don’t dally, such vendors usually give up and leave you alone.

But it’s harder to deal with the seemingly friendly local encounters that reveal themselves as scams designed to bring out your wallet rather than your goodwill. Like the man in Bulgaria who struck up conversation with us in the street only to foist the business cards of his gentleman’s club on us five minutes in. Or the Thai peddler who let my friend carry his bag on a stick for a block, only to turn around and demand payment for the privilege. Or the elderly Moroccan man who found me wandering lost in the medina of Tangiers and accompanied me to my intended destination amidst friendly conversation, only to sink to his knees upon arrival and beg for coffee money.

Such interactions are intrinsically disappointing, but what’s worse is that they poison the few legitimate relationships I happen upon (like Arturo) with suspicion and doubt. I cannot be sure of a stranger’s intentions in the Third World, but I’m usually not far off the mark when I guess them to be fiduciary.

And this is a terrible shame. I view all relationships as transactional – in any friendship things are being freely given and taken by both parties. Solidarity, a partner in crime, common interest, or just someone to talk to – these are all common things in the friendship marketplace. But what makes it magical is the lack of money exchanged for such services. You’re not friends with someone because they pay you to be – you’re friends with them because you like them and get just as much out of the relationship as they do. Accordingly, you give them little bonuses, like picking up their lunch here, offering a couch to crash on there, or a shoulder to lean on in times of need. These are starkly priced commodities outside of friendships (look at restaurants, hotels, and psychiatrists, respectively), but on the inside they are unspoken guarantees.

Romantic relationships have even more give-and-take going on, since they provide vitally important things to each party. That’s why they’re so much harder – so much is being given and taken that sometimes the balances are uneven, or one person comes in looking for something that the other is not willing to offer. And they provide an even more obvious distinction between organic and inorganic offerings – you can’t hire somebody to be your girlfriend; it becomes a completely different relationship at that point

This trust and goodwill is often absent when rich travelers come to developing counties, sadly. Certainly you can find authentic friends in such places – if you stick around and invest in the community with an open heart, there’s always true friends to be had. But on the street, when you only have a few days in the city, they see you as nothing more than a big walking dollar sign, and thus you come to see them as nothing more than greedy scavengers. Human interaction is transformed into a soulless accounts payable spreadsheet, and the joy of connecting with fellow humanity is lost, to the detriment of all involved

But who am I to condemn these opportunists? They’re never asking for more than what I would spend cavalierly on a candy bar at the gas station back home. That paltry sum is worth far more to them than it is to me, as it probably comprises the majority of their daily income. By refusing to play their game I may be shirking them of the daily bread, and the only cost to me is a few moments of annoyance along with a dollar or two. Shouldn’t I acquiesce to their demands and brighten their bland lives that short bit? Yet by doing so I reinforce their addiction, and the next hapless traveller to come this way will get set upon just as vociferously. Most importantly, I contribute towards degrading human kindness into commodity bartering.

This is why I detest the American policy of tipping. I shouldn’t have to pay you extra in order to receive my food or beer without hassle – the cost of the delivery of the product should be part of the product itself. It’s not like we’re shipping it across the country. By separating it, every nuance of my interaction with the waiter/waitress is now part of the balance sheet, and any kindness on their part becomes inauthentic, as it is now a calculated business decision. But that’s an entirely different blog post.

I still haven’t come up with a good answer to the question of whether to enable such commodification of human interaction abroad (or here, amidst homeless beggars who are just as grateful for a dollar). It makes me treasure the authentic friendships and interactions I have with others all the more, no matter where I am. Meaningful connection with other humans is possibly the most important and rewarding part of life, and thus it should remain sacred.

Photo from Greg Younger

Weekly Review #48: Startup School, @thinker on blog startups, and content toolkits

I attended half of Y Combinator’s Startup School Silicon Valley event this week, which was an accurate portrayal of the Hacker News crowd in real life. Very few blonds, lots of Russian and Chinese last names, mediocre social skills but all working on something awesome. Here’s some talk summaries:

Danae Ringelmann, founder of Indiegogo

  • Figure out the Why behind your project, as it attracts like minded cofounders, removes your ego, gets you through the tough years, and allows you to refine you strategy (similar to Simon Sinek’s mission)
  • Use the 5 Whys exercise – ask yourself why you’re doing what you’re doing 5 times, ending on a basic belief you hold. The last answer should be “Because I believe X”
  • Diversity is super important because without it everyone thinks the same and you cannot innovate
  • To build your culture and values, ask the early employees why they work there. Their answers determine culture.

 Kevin Systrom, founder of Instagram

  • Built ‘Treelist’ Craigslist competitor at Stanford – pretty sure a college student has this startup idea every year, to connect seller students with buying students
  • Built it while studying abroad in Florence, which helped because he didn’t have to see all the bad responses in person
  • Was able to have a successful launch because of a stellar network built over years. Then he just sent Instagram to everyone he knew saying: ”Hey can you use this thing and maybe tweet it if you like it”

 Reid Hoffman, founder of Linkedin

  • Game changing companies are usually funded when capital is tight, because there’s less competition
  • Raising too much money in Series A is a recipe for disaster, it makes you overconfident and feel like you have time/cash to spare when you do not. Track record for these companies is bad.
  • He asked all smart friends what they thought about his idea at first, and they said it was dumb, which is fine. You just have to know why they think it is dumb, and then address that issue. (With Linkedin was lack of initial value, without people)
  • He thinks that the fact that everyone has a phone remains underexploited
  • Key nuance of Peter Thiel’s infamous question is: against which audience?
  • Against Silicon Valley, he believes government is important, as its the platform we’re all on. We’re like fish saying that the aquarium water we’re in doesn’t matter. Somebody needs to optimize it better.
  • Entrepreneurship is facilitated by dense connections like those of Y Combinator
 I also sat down with a few smart SF denizens, namely Andrew Chen (who had enough advice to warrant a blog post) and Nick Frost, Mattermark’s BizDev guy and the founder of StartupList. He said:
  • There are 2 things to do with every startup idea- customer development, and things that don’t scale. That’s how you get to the next stage of growth.
  • He built StartupList from his tent in Afghanistan, and jumpstarted a strong network as a result, allowing him to move right into the Valley.
  • Find a niche market underserved by content and build THE platform for people to connect there. Bam, you’re an expert – now find sponsors, and you’ve got a business.
  • Many startups started like that – as blogs or newsletters
  • There are so many digests along those lines now that there could be value in cultivating a digest of digests
  • Look for ways to ‘increase your personal gravity’ – things that make others join your orbit. This is done through creating stuff that other people like – social media, business, content. Kinda like a personal brand.
  • His personal mission is to create environments for people to thrive in – what’s yours?

Nifty startups: Kitestring, which texts you to make sure you’re okay and will alert friends if you don’t respond, Downtyme, which cross-checks your friends’ schedules to find mutual free time, and Point, which lets you share specific parts of webpages super easily, and Trippy, a sort of Quora for travel questions. There’s definitely still a need for a smart personal scheduling app out there, and while the sharing space is over saturated, I’ve always wanted something that would almost automatically send the cool stuff I see to the people I know who’d like it.

Resources: SumoMe, with free traffic-growth tools that work on any website, Course Report, which helps you choose which coding bootcamp is the best fit, QuickSprout’s Content Marketer Toolkit, and the Lifehacker’s Best Of How We Work 2014. San Francisco’s Hill Mapper map is also helpful.

Blog posts: Scott Britton on getting a startup job – the best tactic is to do the job before you are hired. Serious Pony warns of the dangers of willpower depletion as a result of all these push notifications. And Psychology Today’s data on what makes marriages work remains as timeless as ever.

I find the Curators Code a novel experiment in today’s internet, where the curator matters almost as much as the creator. New symbols can’t be the right answer – surely there is a tech solution here where you can mouse over links and see where they came from?

Fun video of the week: French hobbyists races tiny drones through forests in first person view mode, which ends up looking just like the the Endor speeder chase from Star Wars.