The wonderful future, or my phone is slowly becoming my wallet

Since Alicia and I moved back into Boston proper, I've started to hold cash on me much less frequently. Back in NYC or up in Salem, most of the establishments we frequent only accepted certain credit cards; many were cash-only.

Now, I can use Apple Pay or order online from pretty much anywhere I frequent – cabs & Uber, groceries from Trader Joe's, Starbucks and most other local chains – for everything else, I'm only really using one of two debit/credit cards. My only actual use for cash, except when I'm not in Boston, is to pay my barber every month. This has been a wonderful way to live, if anything because I have to worry about having less with me at any given time. My only further request is that I could get my driver's license and MBTA subway pass somehow onto my iPhone – then I could ditch my wallet almost completely.

Having a thinner wallet is kind of amazing, but my iPhone is starting to feel like a single point of failure. What if I drop it and crack the screen or damage the NFC chip or the Touch ID button? The 6s Plus has amazing battery life1, but what if it dies? Do I replace my wallet with my little Anker portable charger in my back pocket? What if I lose or forget that? What if I get mugged? Or worst yet, what if I lose the phone due to my own idiocy? How will I get my goddamn Venti iced coffee?

It gets me thinking about product redundancy – the physical wallet begins to act as backup for my virtual Wallet. But what happens when I have no need for a physical wallet anymore, other than to cover my ass if my phone dies? That's kind of an annoying prospect? Is that what Apple's betting on with the Apple Watch, if you ignore the lifestyle play? When does the "all-powerful device" with several obvious Achilles heels require redundancy, especially when you don't want to also carry your phone in an Otterbox case and with a portable charger constantly?

It's all really fascinating, is all. It's interesting to me that we still don't have a good, trusted, redundant solution here that's also convenient and cheap. We have it with our digital files thanks to name-your-cloud-storage-and/or-backup solution, but credit cards, identification and other highly physical-world things are still confined in your pocket or purse one way or another.

I get excited for our inevitable Minority Report-like future in which we could have public kiosks where, via a retina or thumbprint scan, you could retrieve a temporary copy of your ID, driver's license, last credit card used, or whatever you lost while out in the world. Dropped your phone and it's useless? Scan your finger at a Touch ID kiosk and you can automatically have a temporary ATM card printed instantly for use. Got mugged or lost your phone in an unfamiliar place? A quick scan could get you quick access to emergency response care, your Medical ID and history, and/or automatically wipe your phone and notify a loved one that you're okay. I don't know nearly enough about the technical complexity of making this work in practice – the scanners would need to be sanitary, damage-resistant, weather-proof, whatever else – clearly there are a lot of holes to this. It's almost certainly easily hackable if we're not careful.

But it'd at least be super cool, right?

  1. Except when I'm testing iOS betas…oops, maybe I should stop doing that.

It’s a glorious day when Apple fixes your bug (UPDATE: oops, still broken)

UPDATE 3-16-16: I did some more thorough tests on my iPhone and MacBook Pro and have run into the Smart Reminders linking bug again – specifically when adding links from Safari on my Mac, then opening them up on my phone. Back to Apple Support forums. Ugh.

It takes a minor miracle to get Apple to fix a bug in any of its software or services. Just look at all the discussion threads about bugs on their forum.

The thing that’s been killing me for months? Dumb Smart Reminders. Apple claimed that, in iOS 9 and OS X El Capitan, you’d be able to remind yourself about virtually anything on your device – a note, a text message, a Trello card, a file on your FTP server – and the reminder would be saved with a simple contextual link for quick access.

Problem is, it’s been categorically broken. Ironically enough, it’s broken when you try to use your phone in the way Apple keeps pushing us to use it – through Siri’s (admittedly mostly great) voice recognition.

If you wanted to remind yourself about a website you were viewing on your phone, and you decided to use Siri to do that, Reminders would (sometimes) create a link correctly to Safari. If you happened to have another app installed on your phone at all (in my case, Ticketmaster, Google Chrome and TripAdvisor), Reminders would instead link to one of those apps – then if I tried to access the website, iOS would attempt to open Ticketmaster and fail to render the website. I’m not the only one with this problem; it apparently happens unpredictably with any number of apps that you may or may not use.

tripadvisor-reminders

Argh.

It wouldn’t have been as infuriating if this was only an issue on iOS – but of course it happened in OS X too. If I saved the same website to Reminders on my Mac using Safari, for some reason, Reminders would instead create a link to Chrome. This wasn’t as bad – at least the site would load – but when you’re like me and strictly use your web browsers for specific reasons (eg. Safari for personal, Chrome for work), this gets annoying.

The worst part, though, was that I could totally see what was happening: if I uninstalled TripAdvisor from my iPhone, Reminders would stop linking to it – but instead link to Ticketmaster. Then it’d link to Chrome if I uninstalled Ticketmaster. If I reinstalled TripAdvisor, it’d start linking there again. Basically, Reminders would work without any other apps potentially risking the link to Safari. You’d think that Apple coded this such that Reminders was aware of the source app of the Reminder, and persisted that link forever. There was some dumb app prioritization happening that was causing TripAdvisor to take preference over Ticketmaster, which got preference over Chrome, which got preference over Safari. (No offense to any of these apps, they’re all great – which is why I have them on my phone, god damnit.)

So, while I wanted to use Reminders for exactly what Apple intended it for, I couldn’t, and had to rely on another (admittedly great, but not for me) app, 2Do, to manage my tasks.


Six days ago Apple released the sixth (sixth!) public beta of iOS 9.3. Yesterday morning, I got frustrated because I was duplicating task lists for my upcoming wedding in both Trello and 2Do – so I decided to try out Reminders again. Saving Trello cards as a Reminder seemed to work. Saving a Note seemed to work. Reminding myself about something in my Amazon wish list worked. Even a stupid webpage someone had sent me went correctly into a Reminders list.

IMG_0154

Yesterday was a glorious day.

Eight months, in an office

10 months ago, I was living what I thought was a dream: working remotely for a decently-buzzed tech startup where I was the lead product guy. I could work in my underwear, start and end whenever I wanted, have free reign to work and travel wherever I pleased.

Then in May, said startup laid me (and pretty much everyone else) off with a week’s notice.

I had seen this coming for almost a year for various reasons I won’t get into – but what did surprise me was the ease of getting back on my financial feet. Those of us who got laid off were offered a new job pretty quickly by Wayfair, an e-commerce giant also based in Boston. So that’s where I ended up.

Eight months later, I find myself finally in my element again. The first three months in this job were total culture shock: I was uncomfortable around so many people, all of them wanting to talk to me all about the work and nothing but the work. I was frustrated with having to commute to an office at all, let alone walking down the street like I would regularly do in New York.

But over the last few months, I figured out a rhythm to make it work for me. It’s certainly not a perfect situation – but then again, what job is, really? – but I’ve had some time to reflect about being in an office again.

(Disclaimer: this is primarily about the experience of working in an office environment, particularly after a stint in startup culture, and is in no way intended to be a reflection of the work I do, or my employer, at all.)


Wayfair employs thousands of people and has an office right next to Copley Square in Boston. When you walk into the office for the first time, it’s hard to not feel like you’re part of something massive, given just how many people are flocking to the Copley Plaza complex between 8 and 9am. You’d think one of the stores in the Copley Plaza Mall was having a blowout – nope, these are just Wayfair employees trudging into work.

After a few weeks, though, the awe of big company size and impact turns into drone-like fatigue…especially as wintertime sets in. Droves of sleepy, freezing employees passing through subway turnstiles, huddling underneath half-broken umbrellas and avoiding puddles of slush (and being forced above ground to avoid MBTA construction), just to stare at a PC screen and talk in corporate-speak.

Simply having to be at the mercy of weather sucks. When I was working from home, if it was snowing out, I could just stay inside. I technically have the facilities to work from home in my current job, too – so it can be frustrating to eschew all this technological capability just to be present in the office culture. Wayfair has offices in several locations around the US and Europe; I can’t tell you how many times I questioned my battling of snowstorms to get into the office, only to sit on calls with my Berlin colleagues all day.

That said, if you’re stuck on calls all day at home, you might never leave the house. Get this: working in an office forces you out into the world. This is something I completely took for granted as a remote worker – I would occasionally run out to a coffee shop for a while to get stuff done, but nothing was more comforting than parking it on my couch for 9 hours straight save bathroom and lunch breaks.

Speaking of which, when you begin to compare home-work and office-work life, tiny subtle details start to surface about your lifestyle. For instance, The cost of your utilities start to become something you scrutinize monthly – I drastically underestimated how much I was spending to run electricity and heat during the ’14-’15 winter while working at home. Finding food to eat in an office is a really hit-or-miss thing, depending on where your office (or home) is located. I have the benefit of being right near Copley Square, where food trucks and solid restaurants abound. My last office job was in an awkward part of East Cambridge, MA, where our best culinary options were in a mall food court. At home, you’re really at the mercy of your grocery list or what (if any) restaurants are nearby; back in NYC, this wasn’t a problem, but in quieter parts of the world, this could certainly be a drawback.

Everyone who Product Manages knows the difficulty of trying to herd cats – oops, I mean colleagues – toward a shared product vision, and this difficulty is only amplified when doing it from afar. Being in the office ensures presence from everyone who matters, including my/yourself. I find myself more productive overall, simply because I had face time with colleagues working on projects with me – and no at-home distractions, like my guitars or my television. I can also use my commute to unwind and/or focus on things I’d never be able to focus on given those distractions. I’ve started writing again simply because I have over an hour of “free time” on the train every day.

Working in an office can be painfully social. To avoid talking only about the work, you need to find common interests with your colleagues: in Boston, it’s generally assumed that this is Boston sports. If you’re not actively following the Bruins/Pats/Sox (or worse yet, following another city’s team) you’re already at a disadvantage. I’ve come to develop a personal brand around music snobbery, pop culture savvy and a more casual tone, which people seem to appreciate outside of my general apathy for sports.

Once you figure your general vibe out, though, working in an office can be delightfully social. You actually start to make friends and engage in social conversations and outings you never would’ve had sitting at home or in a coffee shop all day long. Sure, there’s spontaneity involved with serendipitously meeting new people at your local coffee shop, but there’s something equally spontaneous in the side conversations that happen at work. My aforementioned music snobbery may manifest itself during a discussion of weekend plans, which may lead to a colleague/friend to check out a band with.

And what happens when the work gets to be too much, and you find yourself stuck at the office all day? Isn’t that the beauty of working wherever you choose? What about those giant cultish companies who directly incentivize their employees to spend all waking hours at the office, or even sleep there?

Well, so, you can just leave. If there’s more work to be done, and your company has a VPN, you can catch up on work at home after having a lovely dinner at a reasonable hour with your significant other. I’ve come to realize (again) the importance of balance – not necessarily the lofty, unattainable “work/life balance” construct of 9-5, but finding a personal balance where I’m challenging myself and working hard, but not burning myself out and still finding time to reflect and find fulfillment elsewhere in my life.


Certain parts of the tech/startup industry paint office culture as a thing of the past, rendered unnecessary by new collaboration technology. Fully-distributed organizations are popping up everywhere, promising uber flexibility and balance. I admire these companies’ ability to embrace technology to try and bring more happiness to their employees – though it is certainly not perfect either. Remember that distributed companies (or remote work at all) is a fairly new concept, far from perfected by any one organization – and the larger the company is that you work for, the harder it is to adapt the necessary processes and technology to enable that flexibility.

All in all? I certainly don’t hate everything. My commute is sometimes frustrating, as can be the work, but that’s part of dealing with everyday life. I genuinely like quite a few of my colleagues (both in and outside of work), which after being remote for a while is quite refreshing. And I’ve achieved a balance that, at least for now, I’m happy with.

The question I now find myself asking more frequently is: where does this go? Do I advance up the food chain of a strong brand with its corporate quirks, or do I keep my hand in some things that could result in more personal freedom? What will ultimately make me a better, happier person?

Well, how many licks does it take to get to the center of a Tootsie Pop?

Product Hunt for abcdefghijklmnopqrstuvwxyz

The other day I came across Telescope, a product that lets anyone launch their own community site, Product Hunt-style. Just when you think you’ve seen too many “Product Hunt for X” sites, someone gives you the ability to generate as many of them as humanly possible.

It’s not inherently a bad or stupid idea, I swear. But every time someone develops some sort of platform that “lets you make your very own X”, I get a little terrified at the implications that platform may have on society – or, more specifically, the silly ideas that the platform enables. If the “Uber for X” mentality gave us things like this, I can’t imagine what a well-marketed “Product Hunt for X” solution gives us.

Because I get bored during my commute sometimes, I came up with a few ideas for Telescope sites that I thought might be good1. Yay for rapid brainstorming!

  • Anxiety Hunt: submit what’s making you anxious at any particular moment; others can upvote the things that they’re also anxious about. Let’s all be upfront about our insecurities, k? (Speaking of which, is Post Secret still a thing?)
  • Bitch Hunter Hunt: Upvote the best lines from the amazing, non-existent movie starring Will Ferrell, Bitch Hunter.
  • Crack Overflow: Stack Overflow, but for people who periodically suffer from plumber’s crack. (What do you post on a site like that? I don’t know, I wear skinny jeans.)
  • Duck Duck Hunt Hunt: post and upvote screenshots and videos of your favorite moments from the classic game, Duck Hunt.
  • Ethan Hunt: Product Hunt for all things Mission: Impossible.
  • Fuck Hunt: Basically, Product Hunt for porn. V2: import the top voted porn images into a live web version of Duck Hunt!
  • Grunt Hunt: Inspired by Eugene Mirman’s I’m Sorry, You’re Welcome, this gem lets users upload and vote on the best interpretations of various sound effects performed by their own speaking voice.
  • Helen Hunt: Product Hunt for all people in the world named Helen. Vote which ones you think are the best! Except Helen Hunt, of course.
  • I Hunt Myself: For the ultimate narcissist, this platform allows you to submit virtually anything you care about and upvote them based on your personal ranking of those things. The twist? You’re the only one who can access your list. And every upvote triggers a little “Me me me!” sound effect.
  • Jerk Hunt: Product Hunt for douchebags. You literally post about a shitty person and something shitty they did, and people agree with you. The worst people are highest voted. We’re terrible people, right?
  • Karma Hunt: Post something good you did for somebody, and people upvote the most charitable acts. Do you get any actual good karma from this? Probably not. It’s mostly self-serving.
  • Luck Hunt: Product Hunt, but if you're the Xth person to upvote something, you win money. THIS IS THE NEXT LEVEL OF FANTASY SPORTS, BABIES.
  • Meta Hunt: Product Hunt for “Product Hunt for X” sites. Product Hunt is sort of already this, but I figure let’s cut out the BS and make a site dedicated to this thing.
  • Nuck Hunt: Same as the aforementioned Fuck Hunt, but for Canadians.
  • Oregon Trail, Telescope Edition: This version of insanity takes the original beloved computer game, The Oregon Trail, and puts every possible scenario in a list. You have a limited number of upvotes and can use them toward rations, game, diseases – literally everything the game has to offer – and the game returns a likeliness of you surviving the Oregon Trail with those decisions. Basically, a way less fun version of the game.
  • Problem Hunt: Upvote actual problems around which people should build products to solve – they can be any problems, large or small. (Disclaimer: this one’s kind of a real idea, and it already existed once as Real Problem Hunt but was shut down – I think this deserves to come back at some point.)
  • Quote Pilot: You know all those sites with huge lists of inspirational quotes? Ever want to make your own soundbyte-y quote? Submit it here and people upvote the most moving ones. Because we need more inspirational quotes every day!
  • Reverse Hunt: Vote for the least cool things. The less votes, the better. Countercultures, unite.
  • Sidetracked: the Game: submit something that distracted you today – anything at all. Other people upvote the things also distracting them. The test: seeing how many of those things you can avoid clicking on. It’s totally a game!
  • Telescope Hunt: Product Hunt for all sites made with the Telescope platform. (No relation to Meta Hunt, of course…)
  • Uber Hunt: Product Hunt for Uber drivers. Or is it Uber for Product Hunt fans? THE WORLD MAY NEVER KNOW!
  • Viral Hunt: Product Hunt, but with auto-sharing upon every upvote. You thought you couldn't post any more content to your followers? Think again!
  • Witch Hunt: Post people you think are witches, and then others can upvote if they agree with you. Then we burn the highest-voted ones at the stake!
  • X for Product Hunt: Post and upvote features for Product Hunt. (This isn't actually that bad of an idea for a feature request tool…?)
  • Yerba Hunté: Upvote the best kinds of maté…?
  • Zoo Hunt: Zoo animals. Which ones are the best? I’m done with this list.
  1. That is, ideas that will probably get made regardless of whether they’re actually good. In fact, most of these are completely ridiculous. But so are people who insist on making their own “hunt” sites for every possible niche they can think of. Yay products! ↩︎

Misanthropy in product management

When I started product managing, I quickly came across and fell in love with the Cranky Product Manager blog. It was everything that I had just started to experience as a new PM — the constant fight for attention in the roadmap, the terribly-defined feature requests, the working ridiculously late for reasons I couldn’t really justify for myself. That blog is no longer active, but the feelings are still alive in many of the PMs I talk to around Boston and NYC — and they haven’t really gone away for the most part.

In my five years managing products I’ve learned to separate my work frustrations from my personal life, not burn myself out and communicate better — yet I’m still at the mercy of external forces: stakeholders not being honest about their requirements, teams not communicating with each other, salespeople overpromising to clients, founders falling back to buzzwords, people being lazy.

And you’re ultimately accountable to deal with all that as the product owner.

This photo intentionally left blurry to signify my hand-shaking frustration.

With all the hyper-positive blogging out there about exciting new products, startups and giant companies doing great things (which I love, don’t get me wrong), it’s worth remembering that in many cases, Product Management is largely a tough, punishing, thankless job, and I’ve found that it’s a little more manageable when you reduce your trust in people just a little bit. This isn’t a bad thing, really — we’re reminded as product builders to test out others’ hypotheses, second-guess user feedback, question assumptions and your options are to blindly follow or question. Both of which lead to a frustrating and/or misanthropic end.

Don’t get me wrong — I love building and managing products, solving challenging problems, and creating awesome user experiences. But I have a little less faith in people as a result of that passion.

(That’s probably why so many PMs end up trying to build their own products instead of building for others. Maybe I should finally try that.)

Want to learn more about who I am and what I do? Go to my website or tweet at me and we’ll hang out.