It must have been at least 20 years ago that I first had THE VISION. I believe I was lying in bed on an early weekend morning, thinking about…breakfast. I pondered my love of blueberry muffins, and much like Elaine on Seinfeld, I was reminded of how much better muffin tops are than…muffin bottoms. Everybody loves the “crunchy on the outside, fluffy on the inside”, and it’s inevitably a let-down when you’ve peeled off the muffin top and are left with all of the fluff, and none of the crunch, in the dreaded muffin bottom.

My idea is kinda simple. A typical muffin pan simply has divots where you put your muffin mix. What if you could somehow place muffin batter into a short cylinder with two open ends? Then, as the muffin mix rose, it could come out of both sides, and voila — a double-sided muffin. See below for a not-very-helpful visual representation of my idea.

OK, so you are shocked at my genius and wondering how something so brilliant could not yet have been built. Well, sorta. It turns out McDonald’s tried this. It looked something like this…

… and it apparently did not succeed (that’s not an actually researched fact; I’m just observing that I’ve never seen or had one so thus it’s not successful).

Plus, if you’re selling a muffin top, you’ve failed in two ways: 1) It’s only 1 top, and I think I rightly deserve to not “lose” the bottom, I just want it crunchy and top-like. 2) What is McDonald’s doing with the bottoms?

My plan would offer you two tops, perhaps slightly smaller than typical muffin tops, with a very small umbilical cord connecting the two tops, where the mix was originally introduced. This would take some super high-tech machinery and tech, natch.

Anyway, as is my theme with these posts, I ain’t doing this — in fact, I’m exhausted even writing about it — but please make me a double muffin top so that I can buy one, slather it in butter, and eat it.

It’s hard to believe that it’s been 15 years since I ran product at Facebook. Long enough that my then pre-school daughter is packing for college. Long enough that, sadly, I can’t help get you verified on Instagram. Other than Mark and Naomi, I don’t believe anyone else from my days above the Chinese restaurant on University Avenue remains with the company.

My experiences with social media have been the opposite of…well, everyone. Starting in 1996, I ran (and even created) many social media products at Yahoo (Chat, Message Boards, GeoCities, Personals, Mail, Profiles, Groups, etc) and then Facebook (Photos, everything else). When I was at Yahoo, what I built was primarily used by somewhat geeky folks who could tolerate God-awful bandwidth and excessive time in front of their Dell PC. When I was at Facebook, none of my 30-something peers had even heard of it (at the time, only .edu emails had access). Basically, I was deep into social…but sorta by myself.

Today, other than a minor TikTok obsession (don’t judge), I’m generally the last person to document every burrito or sunset I experience. I never really figured out Snap (as I think they intended all along), I rarely post on Facebook or Insta, I mostly use Twitter to rant about bad customer service, and I feel a twinge of sadness every time something beautiful/terrible/remotely interesting happens in this world and all anyone can think to do is record it. Perhaps it’s age or nostalgia, but I miss physical photos and physical art. I know far too much about random people I never really knew and far too little about people I should know better. Our collective level of self-absorption has surpassed anything I could have imagined.

A number of my former peers have come out hard against Facebook — Sean, Chamath, Chris, Brian Acton, etc — some even going so far as to write books or call for the company to be broken up. Personally, I find it incongruous that someone can take billions (yes, billions) of dollars in compensation from the company they helped build, then leave and then turn around and attack the source of your wealth (and a thing you helped create). Perhaps I’m just too loyal or too stupid, but I don’t feel I have the right to criticize when I have been so excessively compensated for my time and effort. Unless I give it back.

Thus, I haven’t contributed to the tell-all books (though incorrect stories have been written about me), been an unnamed source for an exposé, or even written a Medium post for my 6 followers. (I did, however, see the movie — to which I give a solid “meh” review.) Lest I sound like I have the moral high ground, also remember that I didn’t work at Facebook for very long (that’s a story for another day), and it was a long time ago, so I don’t think I’m much more qualified than others to opine on Mark’s current thought process as a 36-year-old (because I knew him when he was 21).

Driven most likely by severe personal insecurity, I started my tech career at Yahoo, and then went to Facebook, on the premise of impacting as many lives as possible. I left Facebook at the age of 35, still wanting to impact lives, but in a way that resonated more with the thirty-somethings and new parents that made up my world. So I started DailyStrength, which I always described as Facebook for health and life conditions. Later on, I started GoodRx, completing the transition to impacting lives through healthcare versus selfies. (I freely admit that sounds a bit douche-y.)

I have mostly positive memories of my brief time at Facebook. I met whip-smart, thoughtful, talented people like Aaron Sittig, Jeff Rothschild, Ezra Callahan and Scott Marlette, who later joined me to found GoodRx. During my tenure, there was little discussion of free speech, privacy or censorship; we were too focused on competing with MySpace (yes, really), tagging photos and hiring, hiring, hiring. In 2005, nobody was talking about the societal implications of social media — we hadn’t eaten the world yet.

Now comes the hard part. When I exited Facebook, I left with a small number of shares of the then-private company. That small number of shares split, and split twice more, and then went public, leaving me ridiculously over-compensated for the contributions I made to the company’s success. For a number of years, the greatest financial success I had ever experienced wasn’t from my decade at Yahoo or the company I started and sold, but from this accident of timing and luck. I will never complain about my compensation, but I’ll be honest - it drove tremendous feelings of guilt and “did I really earn this?” shoe-gazing.

In 2012, not long after Facebook’s IPO, I decided that I would set aside some of my FB gains for charity. A combination of an increasing desire to improve the world around me (having kids will do that to you) and a nagging feeling that I hadn’t earned that good fortune originally drove me to set aside about $1.5 million during those 3 years. After the 2016 election, like many Americans, I started to feel less comfortable with Facebook’s growth-oriented decision-making and the overall impact of social media on society. Rather than complain about it, I resolved to use my money instead of my mouth.

This past week, after 15 years of being a Facebook shareholder, I donated the last of my holdings to Chrysalis, an organization that helps homeless and low-income people get jobs. I am proud to say that my family has now donated over $15 million to 115+ organizations that focus on healthcare, social services, justice, education and arts, with a special emphasis on people of color. And that’s just the tip of the iceberg — we have bigger charitable plans for the remaining wealth we’ve accumulated. I’m still learning how to give with impact — doing it right requires research, soul-searching and commitment. I never seriously read a balance sheet in my career, but I’m now combing through financial documents of charities. I welcome any and all feedback as I attempt to learn this new skill.

What I know is that my demons have faded a (little) bit, and seeing the impact of Facebook’s success delivered to food banks, shelters and teachers helps me sleep better at night. I remain concerned about the societal and political impacts of social media, but while others lead the charge, I’ll use my unexpected, undeserved gift to help others.

Adios, Facebook stock. It’s been a trip.

Of all the (many) podcatsts I listen to, my favorite is 99 Percent Invisible. I’m a sucker for random bits of miscellaneous history and 45-minute long explorations of bad music, and I think of myself as a frustrated design/UX/product person, which basically makes me the perfect listener.

But I’ve learned that all podcasts have lame-ass episodes. For example, I’m digging the new Conan Needs A Friend podcast, which is loaded up with A-list comedians, but I’ve learned that 70% of comedians aren’t really funny when they’re with Conan; their lives are more boring than I thought (sorry, Sarah Silverman).

I felt this way when I started listening to 99PI’s recent episode about the lowly bus. Unlike this amazing odyssey into soccer history and the fascinating history of Northern Ireland, I just wasn’t excited when Roman Mars’ oddly satisfying monotone started talking about buses.

But I warmed up quickly as the story described how unappreciated the bus is as a solution to the god-awful bloody hell that is traffic in our cities. I’m a big, big, big Elon/Tesla fanboy, and when he first announced The Boring Company, I reacted as if he had just invented water. Tunnels! They’re safe! You can stack ‘em! Sign me up!

But then I listened to the 99PI podcast, and my perspective changed. See, the podcast pointed out that buses have a bad rap, but that’s mostly because we’ve chosen to under-invest in them relative to adding more freeway lanes and traffic lights. I know, I know — you’re thinking “Buses, yuck.” You’re thinking:

1. Buses are dirty, gross and unsafe.
2. They don’t run where you want to go.
3. They take forever to show up.
4. They’re no faster than driving yourself.

But if you think about it, all of the problems above could be solved with money. Dirty and unsafe? More cops, newer buses, etc. Not where I want to go? More/better routes. Never show up? Just add more buses. Not faster? Dedicated bus lanes; punish drivers.

I’m a big Uber fan, but it’s sobering to think that 40% of Ubers that are clogging up your city are empty drivers looking for their next fare. No matter how much we improve cars, they’ll always be less efficient that one vehicle that carries 40–60 people. Tunnels are awesome, but they’re still damn expensive and good luck getting one built in your town. Didn’t the new(ish) NYC subway line take 100 years to build?

Buses just have a bad brand. They’re old tech (Group riding? Zzz.), not easily disrupted by a small startup, and they’re damaged by decades on underinvestment. In my city (Los Angeles), some improvements are being made to light rail, but just imagine both how quickly and how impactful an awesome bus system could be. The right system would have to have powerful incentives and disincentives — free rides on buses? Wifi/plugs/snacks/sleep pods/mobile bars/driverless tech? Dedicated bus lanes that make private car traffic even worse? It would take a while, but for what seems like a relatively small investment and a much shorter timeframe, perhaps we could start to change minds.

We’ve tried lots of solutions — we currently use Zoom, we’ve used Google Chat / GoToMeeting / Join.Me / WebEx / Skype, all with varying success for video conferencing. Just connecting is a hassle, and no matter how much we spend on fancy speakerphones, hardware and bandwidth, inevitably there’s dropouts, echos and, my favorite, the “oh, didn’t realize mute was on”.

On the product / communication side, we use Slack, Asana, Confluence, etc., but none of these solutions make a remote person feel like they’re an engaged part of the in-office team. These apps are good for organization, but not good for spontaneous communication.

Thus, I wonder if there could be (or should be) a solution where you’d have an always-on video and/or audio solution to connect you to your teammates.

I’ve wondered about some of the features. For example, I don’t want someone listening to me / staring at me all the time, but I’d like to know if they’re at their desk / available to chat — so perhaps a translucent/automated presence indicator? I presume that my audio would be off by default, but with a click I could unmute. Should the unmute power be on the speaker side or the listener side? Is it like a walkie-talkie?

The key to my (not good) idea is the always-on video presence. The very act of having to dial/wait/answer a call removes the dynamic nature of a conversation for teams that work closely together. Some years back, I went to a fancy office that had an always-on video connection with a half-conference table at each end, so it looked like you were in one big room together. Smart, but also wildly expensive and space-consuming. Plus, only really useful for formal meetings. I want this type of a solution, but for everyone.

I want to be able to touch a screen / push a button / just speak and know that my teammate is on the other side, able to answer in real time. I’ve actually thought about this app for phones too — why do I need to call my wife and kids? Shouldn’t there be a simple press-to-talk app for your closest friends and family? I’m pretty sure this has been tried, but it’s late and I’m just too damn lazy to Google it.

My other issue is that the very nature of having yet another app on my desktop is depressing. I wonder if this would be better as a dedicated iPad, sitting next to my screen, showing me all my teammates in some shape or form. I could see who’s there or not, touch the screen to talk (which would unmute both sides), and just release when done. Or something like that.

Someone else should solve this so I can buy it. Please get on it asap. :)

I’ve been obsessed with social media for over 20 years now, and I’ve been fortunate enough to have played a part in the creation of a number of new ways for people to meet each other using new technologies. I built Yahoo! Chat, Groups, Personals, Photos and then went to Facebook for a time, so I’ve seen the good, bad and the ugly when it comes to human interaction.

While we’ve become a society that’s addicted to social sharing and self-publication, technology has yet to insert itself into some very basic human interactions.

One area I’ve always wanted to explore is Temporary Social Networks. Unlike creating a connection with someone you know via work or friends, this product would be based on limited time and place windows. For example, if you were taking a flight or staying at a specific hotel, wouldn’t it be interesting to be able to interact with fellow travelers? If you were at a conference or visiting Kauai for the week, it’d be fun to be able to browse and connect with new people with shared interests.

Limited versions of these products exist, but none seem to have stuck or created critical mass. Conferences often have apps these days, and you can browse and sometimes connect with other attendees. Tinder and other dating apps have the ability to geographically focus, but not the confined communities I envision. On some planes, there have been chat tools for years (although no one has ever used them). But I’ve never had a hotel or an airline ask me if I wanted to meet the other folks I’d be flying/staying with…and I’d certainly be intrigued.

While less temporary, I’d also love to be able to meet others in my condominium, apartment building or on my street. NextDoor and others have tried, although they’re less profile driven, and more message board.

The challenge with interacting with people you don’t know is that you may only want to meet certain people, and you may want to avoid others (i.e. a woman who doesn’t want to be propositioned in a hotel). OK…that’s a reasonable ask, and I think Bumble handles that well. This app could have similar thresholds — I only want to be visible to married women ages 30–40 who like yoga, for example.

I think my expectations are unrealistic and fail to account for human behavior, as I think most people get really weird around meeting new people. I’ve always tried to use technology to bridge the gaps that prevent people from meeting each other, but it seems that people’s aversion to meeting strangers has only gotten stronger over the years since the Internet was born.

So, I’d say this idea has a lesser chance than others at being a commercial success…this is more of an observation of a gap that, in a perfect world, would be a nice use of technology to increase human interaction. It would be fun to meet new people

When I travel, I like to pack small. I’ve had too many mishaps with luggage, and checking a bag costs about as much as a Michelin-star dinner these days. Plus, I have a family — including 2 teenagers — which means I can expect to be challenging basic physics as I attempt to stuff a dozen oversized suitcases into some tiny European micro-hatchback. So…I choose to pack light.

Of course, when you’re packing light, you end up with unpleasant decisions that start a few days into your trip — most of which revolve around the acquired fragrance of that t-shirt I’ve worn for 3+ days in tropical weather. See, I sweat. A lot. I sweat when I travel, I sweat when we go somewhere warm, and I even sweat in the cold. Heck, I burned through a surprising amount of t-shirts in Iceland in March!

There is a unique form of stress that accompanies this gradual decent into foulness. It generally takes the form of that plastic bag and 3-ply printed sheet that every hotel sticks into their guest closets. I call it their Fuck-Off Form, but they call it the hotel laundry service. I call it my name because the prices hotels charge for laundry are so outrageous…you’d think they don’t want to do your laundry. Which, now that I think about it, they probably don’t.

Here’s just one example I found on Google. In all honesty, these prices are low. I’ve seen $15 to launder a pair of underwear, $20 for a t-shirt. I’ve found dozens of items where the cost of laundering something exceeds what I actually paid when I bought it. Need express service (i.e. less than 2 days)? It’s 50–100% more. These prices make the minibar look cheap.

My solution to overpriced laundry has been to attempt to find a local drop-off or fluff-and-fold operation nearby. I’d say about 50% of the time, I can find a place that can turn my laundry in about a day, and they typically charge about $10, or about 8% of the $120–150 it would cost to launder the same amount at the hotel. But I have to lug my family’s laundry around the neighborhood, disrupt my vacation and work around the laundry’s hours.

About a decade ago, hotels used to charge a ton for Internet service. At the time, I had an idea of setting up wireless access points across the street from hotels and charging $5/day instead of $20. But…most hotels have begrudgingly accepted that they need to offer wifi for free. So I’d like to revise that idea to…laundry.

I would like someone to provide an app that allows me to order reasonably-priced laundry services to/from my hotel room. I’d gladly pay well above laundromat rates — how about $20–30 for a load of laundry, more if rushed — and I think many other travelers would too. Now that I think about it, these same services could provide everything the traveler needs — cheaper minibar items, forgotten toiletries, dry cleaning — all the services that hotels gouge guests on.

This idea just doesn’t seem that hard. I know that there are laundry service apps for busy people — including Rinse, iClean, Washrunner and more, but they all seem to be designed for residential markets. I suppose I could try to use them, but would they be able to access my room or pick up my laundry from the concierge? Not clear.

I’m guessing that generating enough demand from a given hotel might be hard, so you’d want to cover an entire neighborhood. Ideally you’d partner with the hotel, but if they consider laundry a revenue source, you’d need the guest to demand the service.

Interestingly, I’ve found many hotels recently have outsourced even room service — I can’t tell you how many mid-level hotels have told me to order from DoorDash or UberEats in the last year — so perhaps laundry is next?

I just want an easy, affordable way to not have to wear Tuesday’s sweat-stained dress shirt again. :)

I’ve bitched about this topic before (when Facebook IPO’d, for example), and I’ve always felt alone. All around me, the belief is that IPO’s must rise; otherwise, it’s bad for investors and bad for the company.

I guess I’ve just never understood the logic of punishing companies for what I would call intelligent marketing and perfect pricing (conversely, I don’t understand celebrating companies for a post-IPO “pop”). Companies go public to raise money and bring liquidity to existing investors. It’s your duty to existing shareholders to deliver returns on investment and not waste capital.

If I sold you a hat for $10, and you turned around seconds later and sold it for $15, I’d be mad at myself for giving up $5. I would be mad at myself for not correctly estimating demand for my product, and I would expect investors in my hat company to be mad that I had underpriced my product.

Yet, for some reason, bankers have convinced us that we should purposely undervalue our own equity when we go public. Completing a successful roadshow and extracting (temporarily) peak value is considered a sin. Why? This phenomenon is especially awful when you consider that most of the buyers on IPO day are day-traders who have no long-term belief in your company; they simply want to make a buck. So, in short, companies reward day traders and ‘friends and family’ with money that would otherwise go to the company’s existing investors and employees. I just don’t get it.

Worse still, this kind of thinking encourages the worst kinds of speculative trading; i.e. investing in a company not because you believe in it, but only because you can make a quick buck.

In the past, I’ve heard arguments about optics and market perception. I find that markets are, well, markets, and predicting them is next to impossible. I also find that what a stock does in it’s newborn days has very little bearing on the company’s ultimate performance (see the Facebook example again).

Someone please explain to me why we endorse and encourage this type of equity scalping?

Before you read this story, note that I haven’t dated since 1995.

However, I did build or work with some of the Web’s biggest (older) dating services, including Yahoo! Personals, JDate and others. I’ve been obsessed with dating apps for about 2 decades. And I’ve been a wingman for friends while they play with Tinder, so I get the basics (even if I swipe the wrong way sometimes by accident — does right or left mean you like?).

I had an idea almost a decade ago, and I even began work on it — video dating via an app. We called it Hello. The idea was simple, almost a throwback to 1980’s video dating. You’d fire up your app, and instead of seeing photos of a potential date, you’d be able to watch them interact and talk. You can Facetune the shit out of a photo, but manicuring a video is harder and hearing someone’s voice is surprisingly helpful in deciding if you could stand hearing it for an evening…or the rest of your life. We thought about requiring the post-match conversation to be video too. We had lots of silly ideas.

But then we got busy, and we never finished the app. We struggled with one issue — while it’s fun to watch videos of others, what incentive could we offer to get you to talk? It’s sorta painful when someone sticks a mic in your face and says “Go”. Perhaps we could present provoking questions or karaoke or something else that would be easy for you to respond to. In 2010, this seemed like an issue, although these days everyone wants to be on camera all the time, so maybe this issue isn’t really a big deal. And now that every human on the planet has Airpods perpetually stuck in their ears, they could listen to the videos in public.

Lots of folks have tried versions of video dating apps, but no one ever did it right. I find TikTok to provide the best video browsing experience, although it’s not a dating app (at least not officially). Are there others out there that I’m just too lazy to Google? In my cursory searches, I found:

• Cougar Mature Adult Dating
• Flirt Hookup

…and other similarly bad-sounding apps, most of which are focused on live video (which I can guarantee you will be 100% dick pix) or just plain sex (which will also be 100% dick pix). I’m not sure live video is the right platform? We all know how Chatroulette ended up (one last time, folks — dick pix).

Also, if you were remotely successful, I’d guess that Tinder and Bumble would just add video to their larger platforms and crush you. But still…it would be fun as hell to build.

So, I ain’t gonna build a video dating app, but someone should. And then maybe Tinder can buy you. :)

I’ve long been obsessed with organizing messy stuff (despite anything you’ve heard from my wife about the state of my closet). I started my career at Yahoo, where we tried to organize, well, the entire Internet. My company, GoodRx, does this for prescription prices and healthcare. I’ve percolated on dozens of ideas that involve taking previously unindexed stuff and, well, indexing it. I’m like a living Dewey Decimal System. (Just FYI, these kinds of sentences often elicit loud, obvious yawns.)

Over the past decade, I’ve become more interested in buying art. I am by no means an expert or even a serious collector, but I’ve managed to buy a few inexpensive photos and pieces. From my novice viewpoint, I have found the art market to be laughably inefficient and frustrating. There are no reliable sources for art transactions; heck, there aren’t even reliable sources for what art actually exists from a given artist. Fakes are a real problem. Galleries are awful at posting their inventory, and artist websites are anywhere from non-existent to unusable (or just Instagram). Auctions are for rich old people.

I find it incomprehensible that it’s virtually impossible to pull up the entire catalogue of a specific artist. Instead, you’re left hunting through awful gallery websites for the 3 or 4 pieces in their current exhibition. You’ll often end up on the phone with a pretentious gallery owner halfway around the world (once they bother to get back to you), or — wait for it — a ‘consultant’, who’s sole job is to help you navigate this mess. Person-to-person transactions don’t seem to exist for serious art; instead auction houses get rich.

We’ve managed to organize information and transactions for real estate and travel…what about art?

Yes, I’ve checked out ArtNet and Artsy. And I’ve checked with a handful of serious collectors and art experts. I’ve been told that there are professional databases that are too expensive for anyone but galleries and museums to access. I’ve tried calling galleries, but they just hawk the works they have. There is no comprehensive place to see all of the art by a given artist.

Now maybe that’s because artists don’t want you to see their “fuchsia phase”. OK, but musicians and movie stars seem to do just fine with their duds out there. Why hide?

I would like to see a comprehensive searchable, browsable database of art. I would like to see artists post all of their work (and get more exposure!). I would like to see a record of sales and know what art is available around the world (or even a “Make Me Move” like function where the artist or owner of a piece of art could post a reserve price). I would like auction houses and galleries to take less and artists take more. Perhaps it’s a Wiki-like non-profit or maybe it can be a transaction platform.

I just want it to have lots of art that I can browse from my couch. :) Someone build this please?

I sleep hot. And from what I can tell, I’m not alone. My wife recently bought us a big, fluffy down comforter, and while I love slipping into it every night, within about 2 hours it’s basically a wet sauna — blazingly hot and humid. I prefer to wear t-shirts to bed, but waking up drenched around 2am is both entirely unromantic and isn’t good for sleep quality.

Pretty much everyone I’ve ever talked to suffers the same fate. Sheets (even nice ones) aren’t particularly breathable and comforters / blankets are amazingly good at collecting and retaining the heat put out by one or two 98.6-degree humans.

We give short shrift to something we spend 1/3 of every day doing. I’ve seen a rise in fancy mattress purveyors, but nobody seems to have a great answer to just getting a comfortable night’s sleep.

So I’ve Googled a bit. I’ve learned a ton, and I’ve found all sorts of strange contraptions that are trying (poorly) to address the problem. The issue seems to be a combination of the heat and the humidity given off by a sentient human being, so the ideal solution provides circulation, dehumidification and heat removal.

The solutions so far are weak. The Chilipad and Bedjet are prime examples. I haven’t actually tried either because I’m disappointed with any solution that involves a super-unsightly mechanical device, pumps, maintenance and noise. Both of them require specific sheets or mattress pads. They’re all energy hogs. And they’re both expensive (i.e. $400–1,000 or more.) My wife simply wouldn’t allow any of these devices into our bedroom.

I don’t have the perfect solution, but I’d love for someone to try some basic (and ideally passive) stuff first . How about comforters with reinforced slats or holes in them to allow heat and moisture to escape up? How about risers at the edges of the bed that allow the passage of air (and possibly a low-energy circulating fan)? How about mattresses that have gaps a few inches under the top layer to disperse heat? Heat and moisture-absorbing mattress pads that pull the heat away (and maybe even store energy)? I’m confident any mid-level NASA scientist could solve this problem with materials that typically aren’t associated with mattresses.

I could do more research on this topic, but the point of this blog post is to accept that I don’t really have the time or motivation to solve this challenge. So I’m hoping someone else can take the lead, so that my days of awaking in a pool of sweat can come to an end. :)