Have Caffeine, Will Travel: Searching For The Perfect Coffee Travel Mug

I like my coffee. And recently set out to improve my portable consumption experience by finding a better travel mug. My two primary motivations are (a) moving away from disposable cups and (b) preserving/improving the drinking experience versus paper. Secondary considerations -> aesthetics, ease to clean and price.

Non-goals: insulation (I don’t need my coffee to stay hot for hours) and durability (in the sense that I’m not looking for something that will survive a 10 ft drop, or needs to go into a backpack while biking). I also have a bias towards glass or ceramic, believing plastic or metal muddles the taste.

Here’s the three I’m currently enjoying. If you’ve ones you love, tweet them to me please!

Ello Jane 18oz Ceramic

The largest of my three and also the heaviest. Base barely fits into car cupholder – which is a negative – but it’s very comfortable in the hand and top feels secure + easy to remove/insert. Dishwasher safe.

JOCO 12oz Glass

Love the design (they also come with just a solid band). Glass doesn’t get too hot. So far I’ve got mixed feelings about the top – it’s easy to put on/off, but doesn’t necessarily feel secure (although I haven’t had any spills). There’s also a slight silicone aroma first few uses, but perhaps will go away. Dishwasher safe.

KeepCup 12oz

Probably my favorite so far in terms of drinking experience (also comes in 18oz size). The one bummer is that it’s a hand-wash only due to the cork.

High Tolerance for Stress, Low Tolerance for Frustration: Your Questions, Kinda Answered

Expanding a brief quip into a blog post might go against every law of internet nature, which suggests most content is improved by brevity. But something I suggested over the weekend raised enough follow-up that I committed to sharing more. And since my tweets are on a rolling 30-day delete, the below will last longer than the 280 character version.

A handful of replies asked questions or provided feedback. Here are my responses, starting with the skepticism, and ending up with the personal stuff.

@hunterwalk, Stop Pushing HustlePr0n About Stress: My tweet wasn’t anything about how hard you should work, or the cost of effort.

@hunterwalk, You Are Wrong In Some Way: I don’t know what to tell you. It works for me. Your mileage may vary.

@hunterwalk, What Can I Read To Better Understand Stress & Its Effects? I recommend these two books. The Upside of Stress by Kelly McGonigal, and Why Zebras Don’t Get Ulcers by Robert Sapolsky.

@hunterwalk, What Causes You Stress vs What Causes You Frustration? Ok, for me Stress has to do with a deep desire for something to be successful, degree of difficulty in executing, an urgency around the window of opportunity to do so and even skepticism from those around you. Most of the work I’ve opted into historically involves stress.

Frustration – again, for me – has to do with an inability to create change in my situation due to others’ process or incentive roadblocks, having to represent an idea that I disagree with as the product of my team, organizational politics, relying upon colleagues or partners who don’t always share my values.

Ultimately I’m a Work-In-Progress so I want to get better as a person. Maybe some of the things which frustrate me I’ll eventually learn to handle more productively. That would be great! But I also rather minimize or route around them, especially when i believe the downside is higher than the upside.

@hunterwalk, What Happened in 2011 That Helped You Separate These Two? My midlife crisis. After 4+ years, I was removed from running the Product Team at YouTube for a variety of reasons – some of which I probably could have prevented, and others that I couldn’t have (or didn’t want to). It turned out fine but threw me for a bit of a loop, one which took the summer, and much of fall, for me to truly recover from. Here’s a blog post about learning to separate my identity and self-worth from my job, which was part of the tumble.

It wasn’t really until early 2012 when I became a dad that stuff started to fall into place for me from a “go forward” plan. A large portion of that clarity came from (a) deciding I needed to live an authentic life in order to be the type of father I aspired to become and (b) I realized that perhaps I could design more of my time around what gives me energy vs saps it.

@hunterwalk, You Basically Seem to Suggest that Frustration Comes From Lack of Control, But You’re Now in Venture? Yeah, investing in other people’s companies for minority stakes does seem to cede control doesn’t it? But here’s how I live it:

  • Satya and I co-designed Homebrew very explicitly to optimize for the things we love doing – spending time with founders (especially post-investment) and each other. We’ve stayed small and focused which means no need to invest in a team that we don’t think we’re the right partner for. And we make decisions by consensus.
  • Once we invest (again, a decision we make by consensus), I’ve signed up to help the company become the best version of what it can be. It’s the founders/team’s startup. I don’t sit on the org chart. I care passionately about their outcome – even independent of the economics involved, but obviously because of that too. And we work closely with the founders to support them, even when or after we disagree.

Ok, I think that was most of the questions from Twitter. Thanks for caring and prompting me to think a bit deeper about my answers.

Oh Shit, Your VC Just Quit Her Fund! What a Good CEO Should Do Next.

Everything is setting up perfectly – you’ve got a great relationship with your lead VC – he’s even saying “we” and painting pictures of being on the podium with you for the NASDAQ opening eight years from now. Then he tells you he likes being an investor but *really* misses being an operator, and is joining another one of his other portfolio companies as COO. You grit out a smile and weak ‘congrats’ while thinking ‘“fuuuuuuck.”

Across town a different CEO is having a breakfast with her Series A Board partner. It’s off-schedule – the two usually meet every other week – but she’s an awesome VC, much better than the older dudes at her mediocre shop, so any time you have is appreciated. You almost spit out your coffee when she lets you know that she’s leaving for a Tier 1 firm but that her partners John, John Jr or Robert will be great stewards of your startup until she has the pull at her new gig to lead your next round.

Hunter’s draft script for SVU: Silicon Valley

There’s lots of movement in the venture world these days. Former operators return to operating; GPs trading up (or being managed out); wealth-effect retirements; whole firms dramatically changing strategy. All the disruption can be pretty jarring to an entrepreneur, especially in situations where the exiting partner represents the top line on your cap table. Observing this both inside and outside of our portfolio I’m sure of two things: a) there’s not a whole lot of public discussion on the topic and b) most founders (and their other investors) should be more aggressive addressing the implications of these changes. I’m going to try and make my contributions to both of these here.

Photo by Leio McLaren (@leiomclaren) on Unsplash

First though a few high-level points:

  • Needless to say, every situation is different. Below I’m really talking about startups between Seed – Series B. After that, there’s often enough people around the table to manage the loss/transition of a GP/Board Member (even if it sucks).
  • Founders (and the other investors) should focus on derisking the downside in these scenarios, not pushing for their own self-interests. It’s the COMPANY that’s being put at risk.
  • It really helps if you are able to remain in contact with the former Partner or have another trusted backchannel at their fund, even if that backchannel is a more junior professional.
  • You’ll often need the support – both structurally and symbolically – of some other investors on the cap table to make the case for some of the ideas below to work. Such as Homebrew 🙂

Okay, time for some game theory. A lot of what happens next is tied to the firm’s perspective on whether you’re going to be a meaningful investment or not (and how much their reputation is tied into your company). Basically they’re either Bullish, Written It Down/Off or Too Early To Tell.

BULLISH aka YOU ARE ABSOLUTELY KILLING IT: You’ll get the sense because the rest of the firm immediately is overly attentive to your needs, wanting to make sure there’s a ton of goodwill. In these cases you can usually negotiate who you want as a Board member from their partnership and if for some reason there isn’t a GP you feel comfortable with, even discuss a Board Partner scenario, where a mutually agreed industry exec/CEO from their network takes their seat on their behalf (but this is higher degree of difficulty). If the reason for your partner leaving was some sort of change in firm strategy or scandal and you just don’t want to be associated with the entity, you can sometimes get the firm to sell into the next financing to the point where they’re not the largest shareholder any longer, etc (but again, degree of difficulty here is expert-level).

WRITTEN YOU OFF: In these cases you’re gonna have almost no hope of getting a new, engaged GP on to your Board. Most likely either a junior representative or a GP that’s assigned to “clean up/wind down,” whether they’ve communicated that to you proactively or not. In these cases you are still basically looking at the options listed below under “Too Early To Tell” but with a very high degree of difficulty. Given that reality, the CEO probably needs to be very direct – challenge the firm to let you know under what circumstance they’d consider additional funding, and if the answer is “never,” try to negotiate them off the Board.

TOO EARLY TO TELL- SOME GOOD STUFF, SOME CHALLENGES BUT A LOT TO DO: Here’s where I think founders and cap tables can should be more proactive. The default is to let the firm assign another person at the fund (hopefully a GP) and then just keep working on the plan of record as if nothing changed. My experience suggests this will be neutral to negative long term, unless you end up in the “killing it” camp by next fundraise. Instead here are some potential shorter-term actions to take:

  1. Re-Pitch The Whole Partnership – Some firms are really good at keeping one another up to date on portfolio progress, others are lone wolf models. Either way it’s been a while since you presented to the whole partnership and you probably never really got the story from your original pitch. Yeah, they did the deal, but it probably wasn’t consensus and those Nays are still sitting there, just without your previous GP pounding the table. It’s time to go back in and win the room over. Note – this is also a reason to make sure you’ve got some redundant relationships – ie proactively bond with some other partners at each of your VCs.
  2. Propose a Top-Off of the Last Round – Again, every VC is different – and god bless those who behave as a true partnership (you know who you are!) – but this business is ultimately about who believes enough to put capital behind a company. Your new GP/Board member didn’t personally sign the check last time – get him or her to do so, sooner rather than later. Even at the cost of a little more dilution. I’m a believer in the psychology of sunk costs. Ask them to take X% of their pro rata reserves for you and do it now as a note or extension of the last round. And the rest of the cap table can come along or not with their pro rata. (A variation on this is getting the new GP to expend a bunch of social capital and increasingly tie their reputation to your company. You can do this through a variety of means.)
  3. Assume You’re Going to Need To Raise the Next Round on Your Own – Goal is to get a new investor on to the cap table who is just beginning their journey with you. Again, I think it’s worth taking a little more dilution than you planned if needed to get this round done as soon as you’re ready. And if the exiting GP can still serve as a reference for you, that helps a ton too.
  4. Ask to Keep Exiting GP on Your Board – If the exiting VC is retiring or returning to operating (vs moving to a different fund), you might be able to retain them until the next fundraise. They are still representing the firm but everyone agrees that due to relationship continuity and capacity for other GPs to absorb Board seats, that things should just remain ‘As Is’ for now. Years ago when my Homebrew partner Satya left Battery Ventures to run Product at Twitter, he kept all his Board seats and incrementally transferred them to his partners over time.
  5. Put Your Investors on the Spot – Make sure you have clarity from your investors whether you are on track to their continued support. If you don’t have Board-level milestones/targets agreed upon, the Board isn’t doing its job anyway. Make sure that your execution will result in support and ask these questions upfront.

As suggested earlier in the post, this is totally a Your Mileage May Vary. My POV is simply that when a company underestimates the impact of a change in their VC relationship, it has potential to be damaging down the road in ways that the founder can no long control, so they should address any elephants in the room ASAP.

If you have different opinions – or even better, experience! – let me know and I’ll append any supplemental thinkings.

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Updated Feedback From People I Respect:

Sean Byrnes, CEO/cofounder Outlier
Bilal Zuberi, Partner, Lux Capital
Enterprise Software CEO who messaged me privately

Why I’ll Sometimes Fund a Startup And Tell Them to Stop Making Money

“Don’t worry about making money right now” is not the advice you’d expect a seed VC to give a CEO right after writing them a big check. Do I not desire the UpAndToTheRightCurve needed to raise a Series A and get me that sweet sweet write-up? Doesn’t Homebrew want steak more than sizzle in the companies we back? Hunter, what’s gotten into you???

I’m longterm greedy, which means ultimately my venture success is going to depend on quality of company exiting, not pump and dumps, or millions in fees. Phosphorous burns white hot but not very long. Unsustainable revenue curves willed into existence in order to prove growth ahead of raising more capital is the organizational version of phosphorous. I want furnaces – a sustainable heat source which goes as long as you feed it. Well, technically I want furnaces that eventually stop burning wood and start spitting out wood, but whatever, it’s a metaphor.

There’s an increased belief (maybe reality for some), that seed VCs want to see revenue before investing in verticals like SaaS, marketplaces, commerce. There are several contributing factors to this spreading notion:

  1. 2019 Startups Can Do More With Less – Because spinning up a startup atop 3rd party infrastructure (eg AWS, Shopify, etc) is lower cost than previous eras, companies can often get to market quicker and start charging for a product, even in pilot/beta form.
  2. Availability of Angel/Early Capital – There are more individuals/funds interested in being your first $250-$500k.
  3. Attempts to Stand Out Among Large Number of Startups – There are so many SaaS, Commerce, Marketplaces these days that founder believe (again, sometimes rightly) that a headline about early MRR/customer traction will get them in the door at a VC versus just a pre-market

The sum total of these is actually pretty positive for the ecosystem – a bunch of aggressive startups who get customer feedback and that $1 in revenue earlier in their lifecycle than the previous generation. But as a seed investor, what really matters to me is how they’re going to get the next 10x, 100x growth, and often it’s not through sheer force of will, but by understanding a segment of customers, and building a cost-effective, repeatable acquisition channel or two.

So when evaluating these companies for investment I’m less interested purely in milestones and more about tactics and learnings. Does your customer base now represent what the next 100 or next 1000 leads will look like? Are your current customers using the product the way you intend and engaged – the stacking revenue heading towards a retention cliff once their 6-12 month contracts are up is a trap for investors. Did you pay 10x LTV in CAC?

These aren’t reasons that I’d pass on an investment but they’re reasons I might suggest, post-seed raise, hey, you’ve got 24 mths of capital in the bank now, let’s take a quarter or two and get the foundation correct, because once we get back on the growth curve, we need to hit those numbers for the A. I’m never afraid of showing a future investor a chart which has four quarters of growth followed by three months of flat/down, followed by another four quarters of even faster growth. I’m deathly afraid of starting each month less certain you’re going to hit the revenue target when you’re three to six months from a Series A fundraise. [I’ll caveat this by saying there are a special class of startups which just happen to find product/market fit very early and it’s explosive from there. In those cases, yeah, you’re just going to be stressed by hiring and keeping the service live, but you still need to start investing in a bit of stability/scale alongside. That’s < 1% of startups, and so statistically it’s not you. BUT IF IT IS LET ME KNOW 😉 ]

In closing: we don’t require revenue before we invest; if you do have revenue, we’re going to ask about what it has taught you; and if there’s foundational work to be done that would make the revenue growth even faster, we should discuss what it means to prioritize that work before getting back on the growth curve.

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What Does “Self-Made” Mean (Or Matter) Anyway?

Kylie Jenner was pronounced by Forbes as the “youngest self-made billionaire ever” and the internet started debating what exactly self-made means.

Hold aside that the Forbes lists are notoriously, well, estimates – I mean, this is the one that Trump was obsessed about ranking on, and would make up all sorts of numbers to successfully to do so. And hold aside that no matter what you think of Kylie’s success and what it says about America, she’s role modeling some notion of business-savvy and Get It feminism, albeit wrapped into a confusing package. What Forbes responded to quickly was backlash regarding the concept of self-made. And they did it in a surprisingly specific way – a scoring system!

First the definition….
Then the scores!!!!

The American mythology of meritocracy and mobility are being eyed with increasing amounts of skepticism by younger generations, and likely always by those less Caucasian and less male. Economic class mobility has statistically slowed as the inequality gap widens but many of us hew to the pick-yourself-up-by-the-bootstraps American Ideal, and if you reach far enough back into the family tree, tell an apocryphal story of a relative who landed on these shores with nothing and made it.

I saw this same reaction in the Twitter replies to an article shared over the weekend. The NYTimes ran a story about how large numbers – a majority in fact – of adults 21 – 37 had received some sort of financial support from their parents. As a friend commented to me, it’s was a weird age range (21 is very different than 37) and the tone of the article seemed to want to shit on someone but couldn’t exactly figure out who.

I circulated the article not because it was millennial shame-bait, or the perfect seed for calling out phony self-starters, but instead to promote why an increased public safety net makes sense — give the people who weren’t born on first, second or third base at least a fair at bat.

Turn the clock back a few days before the Times article and you’ll get to Ivanka Trump chiding AOC’s “socialism” by saying Americans don’t want handouts. Elizabeth Spiers, who once worked for Ivanka’s husband, responded in the Washington Post by articulating why this “self-made” myth prevents economic policies which would extend the type of headstart the economic privileged have to broader groups. They need to continue deluding themselves because so much of their self-worth is tied up in believing they did it themselves.

And it’s not limited to the denizens of the White House. I see this too in my own community.

It’s wonderful that some people are able to be helped by their families directly or have stability to fall back on. It doesn’t belittle the hard work that they did to continue or extend their success (the inability for some folks to concede that luck played a role too is a different rathole). My hope is that it starts a conversation about how to support others even fractionally to the degree they were kickstarted. We’ve had enough ladder-pulling and self-made self-delusions to last me until the next Presidential election (but hopefully not long after 😉 )

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Indie Software I Pay For

A tweet resulted in a thread…

Which then resulted in a longer blog post from Jason Rowley on what indie software he pays for. Which then spurred *this* post. For purposes of definition, I’m using “indie” as (a) not owned by a big tech company and (b) haven’t raised tons of venture capital (to the best of my knowledge). Like Jason’s disclaimer, I too am likely forgetting some stuff. So, in alpha order:

Bear – My favorites Notes app on MacOS/iOS. It’s not bloated with features and just feels, I dunno, fun to write in? I use Bear especially when I’m taking notes while also being on a video/phone call.

Feedly – My RSS backend feedreader (Per below, I use Reeder as a consumption frontend)

CopyClip2 – I actually haven’t upgraded from CopyClip Original yet, but this is the MacOS app I use for clipboard management. Copy, paste, copy, paste.

Magnet – MacOS app that makes rearranging/tiling application windows into a snap.

Overcast – There are a bunch of excellent podcast apps but I’ve settled on Overcast in a combination of satisfaction and inertia. Indie software is often opinionated and I like the fact that Overcast’s creator is unlikely to sell us out or ship something shitty.

Reeder – My feedreader of choice. RIP Google Reader.

Twitterrific, Tweetbot – Although I primarily use Twitter’s official client, I care enough about the ecosystem to historically support high quality alternative clients.

There are a bunch of paid/freemium iOS apps that I’ve bought, some of which I use, but the ones above are the ongoing subscriptions or the one-offs I wanted to highlight.

Would You Put Your Job On Your Tombstone?

As a kid I’d prowl graveyards with my mother, tightly holding sheets of wax paper and thick, flat Crayolas. Macabre backdrop for sure, but our interest was in art not mischief. Upon discovering a tombstone with especially interesting inscriptions or carved pictures we’d overlay the wax paper and rub the crayon up and down the sheet. The resulting artifact was a color representation of the words and images beneath. You can look at this rubbing of a leaf and imagine the equivalent.

Besides an awesome relationship with my mom (these weren’t even close to the weirdest stuff we did together), those days left me with an appreciation for how people told their final personal story. Around New York City suburbs and occasional trips to New England I read centuries worth of lives lived – maybe this was the spark which eventually turned me into a history major at college. Died young. Lived long. Families buried together over generations. My thoughts kept coming back to how they spent their time and the identities they chose to project from the headstone. Father. Son. Husband. These were common. Friend. Veteran. Those appeared frequently as well. Less so was your profession – maybe the oldest graves referenced a trade, but as you crept towards the late 20th century the idea of your work being important enough to chisel started to disappear.

Although I wouldn’t be able to articulate myself quite this succinctly until I reached my early 20s, it was around this time that I started to believe you should only work on projects worthy of your tombstone. Why otherwise spend thousands and thousands of hours doing something? And that if I had opportunity to use this heuristic as a filter, damn right I was going to do so.

And so I did and I have. I’ve worked at companies and in roles that I feel strongly enough about to make eventually part of my resting legacy. Not to the exclusion of the other identities and relationships I hold dear but not compromising either.

When I’m talking with a startup founder about their company and whether Homebrew might be the right partner for them, I probably over index on “founder < > market fit.” Why does this problem matter to them? Why do they want to work on it for the next ten years? And what would make them proud? Not just what would make you successful, but what would it mean to be proud of what you built. The financial outcome can (must!) be a part of that, but I think it’s a leg of the stool.

Sometimes I’ll say it directly: I want you to care enough about this company, and ultimately be proud enough of the outcome, that you want to put in on your tombstone, not just your resume.

This doesn’t mean sacrifice everything for your job. This doesn’t mean neglect other people and pursuits you care about. This doesn’t mean win at any cost. This does mean don’t be afraid to apply yourself to something that feels like your life’s work. And if you’re not currently doing that, what’s holding you back?

(1) In also a cute play on words, a “tombstone” is the term used for the small celebratory statues that an investment bank gives out for a successful transaction (IPO, M&A, bond issue, etc). So if you’re founder who ends up building something “tombstone-worthy” it kind of has a double meaning in a way that makes sense 🙂

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Wait, Did Amazon Just Build Their Version of Westworld? No, Of Course Not But…

Now it all makes sense! Bezos’ post about his penis and HQ2 dramatic break up with New York City was all just a con man’s swerve, a magician’s distraction, to cause us to look one way while the real story happened under our noses (and keyboards): Amazon built their Westworld!

As we now know, the plot conceit of Westworld is that there’s a corporation mapping our every desire to build the ultimate marketing database! Yes, that’s right Dolores, Delos is just another adtech play

So what am I supposed to think upon reading that Amazon has released a Sandbox MMO game? That this is just another way to build value into its Prime offering? Sorry n00b, but no.

By design a sandbox game is meant to provide open-ended exploration where a player’s true nature helps them pick a path of enjoyment, and which over time, their “player type” is revealed by their actions.

Now maybe you’re thinking “Hunter, you’ve lost it. Get out of the QAnon subreddits and come back to us,” but I’m not crazy, I’M NOT CRAZY…

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Five Questions With Jeff Berman (Public Defender Turned Kardashian App Builder)

I met Jeff Berman during my YouTube years. He was an exec at MySpace and we were probably talking about a host of different partnership-type ideas that I don’t believe went very far. Fortunate for me, the collaboration of our friendship has been more enduring. Jeff is huge brain, huge heart, huge presence. Involved across a variety of commercial and non-profit efforts, he’s quick to volunteer his help and always lives up to his words. It gives me great pleasure to introduce you to him as well via Five Questions.

Hunter Walk: You’ve got a perfect “dinner party” background – begins as a public defender, then Counsel to Senator Chuck Schumer. Transitions to social media with MySpace at their peak, and then, um, the less peak part. Then working with capital T talent at the NFL and helping the Kardashians create their digital empire. If someone just looked at your resume, what narrative do you think it tells?

Jeff Berman: Well it certainly seems random. And it definitely wasn’t planned. The reality is I made the leap from law, politics, and policy to the intersection of media, tech, and commerce because I fell in love and moved to LA to be with my wife. That required a hard reboot of my career. Over time, I realized one of the core skills I’ve learned across these industries is how to build teams capable of attacking problems that don’t have obvious solutions. I’ve also learned that I’m best when I have 14 plates spinning and 18 balls in the air at once. So I’m drawn to opportunities full of those challenges.

HW: Having been at MySpace 2006-2009 do you have empathy today for what Facebook, Twitter and YouTube are trying to solve (safety and abuse, manipulation)? Do you think regulation should play more of a role in guiding their forward plans?

JB: There’s a degree to which I have empathy and a degree to which I’m exasperated.

There’s a lot of grey in this. You have unwitting bad actors who should not be banned from platforms because of the honest mistakes they make or because they adhere to fringe ideologies which, while often odious, have a legitimate place in the public square. It is exceedingly difficult to establish clear policies to deal with that grey. So there’s empathy.

You also have a set of repeat bad actors where the only logical conclusion is that they intend to spread disinformation — where it’s patently obvious their mission is to sow hatred, fear, and division. Those parties are actively attempting to subvert our democracy and the platforms aren’t doing nearly enough to stop them. So there’s exasperation.

More broadly, this speaks to these corporations re-evaluating where stakeholders sit relative to shareholders. Reid Hoffman is among those who have argued that at a certain point in a company’s lifecycle, society becomes a key stakeholder. The major platforms are undoubtedly at that stage and their missions, values, policies, staffing, and investments need to reflect that. They have a long long way to go.

This only gets fixed when it’s properly prioritized by the CEO. Even then, it cannot be solved by algorithm alone.

You need clearly articulated policies and human beings exercising actual judgment in the process. You cannot be paralyzed by fear that your judgment may be criticized. It will be. And sometimes legitimately because your judgment will be imperfect. But it will be a heck of a lot better than it is today.

On the regulation front, there’s good and there’s bad. When I went to MySpace, Chris DeWolfe, our co-founder and CEO, made safety a company-wide priority and we owned up to what we were doing poorly. Then we proactively worked with Congress, state legislatures, state attorneys general, public interest organizations, and others to develop internal policies, promulgate best practices, and partner to craft regulation that would help protect customers without strangling business. That’s the best scenario.

Unfortunately, there come times when an industry is being irresponsible and facilitating such harm that government has to step in and act. Regulation can have major unintended negative consequences so it’s generally best when government can work with industry and public interest groups to craft solutions everyone buys into. I’m a born optimist and my hope is that as governments move to regulate the platforms, everyone will get onboard to craft the best solutions.

I’m also a realist and, like it or not, regulation is coming.

If industry won’t participate collaboratively and constructively and if we keep heading in this direction, that regulation is increasingly likely to be draconian.

HW: Whalerock, where you were President, is one of those stories where millions and millions of consumers have touched your products – such as the Kardashian apps – but probably never heard of the company itself. What did you do over there and how did it influence your understanding of what “influencer” means today?

JB: I’ve been incredibly fortunate to see how brands are built in a number of different contexts — politics, music, sports, celebrity, and even law. There are those who say that brand is dead in the age of Amazon. I would argue that reports of brand death are greatly exaggerated.

Identity is a core element of humanity and how we align with (or against) brands speaks to who we are. The music we listen to, the shows we watch, the teams we root for, the clothes we wear, the campaign bumper stickers on our cars, even the food we eat — these are all examples of how brands help us express identity. This is especially the case in the era of ubiquitous photo taking and social media.

The paradox of the current era is that it’s never been easier to build a brand (because the traditional gatekeepers have been swamped by the Internet) while it’s never been harder to build a brand (because it’s never been more crowded). At Whalerock, we were working with creative talent (you can call them influencers) who could organically break through the noise while working to build businesses that leveraged both the traditional and new worlds of media and commerce.

HW: Now you’re on to Magnet – I know you want to keep this answer high level (we’ll do a follow-up once the covers get pulled off), but what is it and why are the three of you working on it together?

JB: The next generation of great brands and businesses will be built on three pillars: content (watch, read, listen), community (engage, share, identify), and commerce (buy). My partners and I have all worked with transformational creative talent to do versions of this before and we came together with a very smart, very patient financing partner who agreed that the best way to do this in the 2020s will be a hybrid of venture and private equity. So we are set up to buy, invest in, and start businesses that will pull all this together. That’s about all we’ll say for now. More to come.

HW: You’re active in progressive politics – do you think the Democrats 2020 race will be about a person or a platform? That is, will the party’s platform ultimately be decided by whichever candidate catches momentum, or will the question of “centrist” vs “leftist” be answered first, and then a candidate selected from that ideological group?

JB: Modern politics really started in 1960 when television came into the mix. Since then, almost without fail, we have elected the president we more prefer in our living rooms. Social media only makes that relationship feel more intimate — for this new era, we are now more prone to elect the president we want two feet from our faces. We want an authentic and passionate communicator who says things that make us feel something real.

There’s a policy baseline, of course. But ultimately, it’s far less likely to be about which version of expanded health care she/he supports; it’s far more likely to be about whether we feel the candidate is genuinely committed to — and can communicate why we must have — high-quality, affordable, widely accessible health care.

At the beginning, middle, and end of the day, it’s about nominating someone who captures the energy of the moment not just to turn the page, but to start a whole new book. It cannot happen soon enough.

Thanks Jeff! To get posts from this blog emailed to your inbox, just sign up here.

Five Questions With Adam Davidson (New Yorker Journalist, Planet Money Cofounder & Generally Smart Person)

In the design of social apps, we’ll sometimes talk about how there’s a Friend Graph and an Interest Graph, and they don’t always mix. Well for my personal Venn diagram of those two, Adam Davidson sits squarely in the the overlap. We first got connected via a mutual friend around the cause of independently funded journalism, but found the topics of mutual joy (and distress) to be even broader. This is a longer Five Questions but I think an absolutely spectacular one and I hope you enjoy it.

Hunter Walk: You were one of the first reporters to focus on Trump’s money trail instead of his tweets, in both longform New Yorker articles and your Swamp Chronicles series. Are you still convinced that his downfall will be tied to these issues versus other accusations?

Adam Davidson: Donald Trump has spent the vast majority of his life–even the vast majority of the time he was running for president–doing business, not politics. His clear overriding ambition throughout his life has been to be celebrated as a rich person. Power and politics have never been a major focus of his. So, it seems to me, the money-trail is a great place to look to find out what is driving him and what he has done.

As it happens, the Trump money trail is fascinating. He ran a business that has long been famously riding the edge of legality, working with people that few other business folks would work with on deals that bear many of the hallmarks of financial crime, such as money laundering, foreign corrupt practices, and tax evasion.

So, yes, I think it all comes down to money. I think Trump is driven by money or, more precisely, driven by the desire to be perceived as someone who has money. I think Trump has shown himself quite willing to take enormously risky moves when he thinks he can get money. I think that his greatest legal liability–by far–is in his business deals. I feel confident that money was his motivation in running for President and in doing whatever it is he did with Russia.

I feel confident that money was his [Trump] motivation in running for President and in doing whatever it is he did with Russia.

If I were on Mueller’s team or if I were working for one of the many other federal, state, and local prosecutors looking in to Trump, I would spend around ninety-nine per cent of my time following the money. Which is, roughly, how I do spend my time.

I also imagine that Trump would choose impeachment and removal from office over losing money or being revealed to have far less money than he claims. If he were impeached, he could spin it to his base as proof positive that he’s their hero. But if he loses his money or is revealed not to have much, he will be laid bear in a way I imagine would be truly unbearable to him.

It would take many, many years for any prosecutor to actually get his money. That’s hard to do, even in non-political prosecutions. But the threat must feel terrifying, I would guess.

HW: I’m mostly an optimist, but sometimes when reading your Trump coverage, I think “yeah, that’s all true but the average person just thinks this is how all rich people act” and/or “this is just evidence of how the system is rigged in general.” So the greater risk beyond just Trump is severe mistrust in institutions – perhaps deservedly! Adam, respond to this question with something encouraging!

AD: Overall, I think it is important to see the Trump era as a net-negative. America is worse than it was before and, probably, worse in a semi-permanent way. Trump has revealed deep structural problems and has created to a path that a more careful politician can take advantage of. We are far more like a corrupt developing country than we had realized. And the shameful behavior of the GOP suggests that our assumptions of political party self-preservation were wrong (it feels a bit like the mistaken assumption that big banks, or the people who work for them, wouldn’t take company- and economy- destroying risks for short term profit).

So, I am deeply, deeply upset. But I am, somehow, also optimistic. Genuinely! And not just when forced to be in a Q and A. There is a good (though far from great) story to be told about the global fight against white collar crime, money laundering, and other financial bad behavior. Much of what Trump has done financially is extreme but far from unique. One of the main lessons of this period is that it is very easy to commit blatant international financial crime and get away with it. Just look at what Michael Cohen and Paul Manafort have admitted to, activities that wouldn’t have been prosecuted if they didn’t work for Trump. There are tens of thousands, maybe far more, doing the same. However, we know about their crimes–and Mueller was able to quickly suss them out–because of a transformation of global financial enforcement.

It’s hard to believe but up until 1986, money laundering wasn’t a crime in the U.S. Right through the 1990s, money laundering and foreign corruption were barely ever prosecuted. There were few tools prosecutors had access to, even if they suspected someone was up to no good. But the U.S. and British governments have forced much of the rest of the world to create a more transparent financial system in which bad actors are more likely to be reported to authorities. Most offshore jurisdictions have had to shift their businesses away from helping

I don’t want to jump up and down and say: problem solved! The current enforcement is both infinitely better than what existed before and only a tiny step in the right direction.  It is still very, very easy for people of means to launder money. But we now have some very good tools and there are some others that could be implemented. We just need political will to increase enforcement and to public will to ostracize those who engage in illicit finance. It may never be a fully solvable problem, but it is addressable and I allow myself to believe (or hope) that we’ll have reforms not unlike the post-Nixon reforms in the US, that make it slightly harder to do bad financial dealings.

I don’t know if this counts as optimistic, but recognizing you have a problem is the first step and boy oh boy do we have a problem and far more people recognize it.

HW: How’s the 2019 Twitter Resolution holding up? Spending less time tweeting? Fewer battles with trolls?

AD: It is amazing how great it is to be far less active on Twitter. I can’t think of anything I’ve done in years (aside from getting married and having a kid) that has brought me so much concrete happiness so quickly. I’m not joking. I was a frequent twitterer and a regular arguer with others on Twitter. It was often exciting, but also stressful, enraging, distracting. It’s embarrassing to admit, but I have more hours in the day, more focus on my work, more time with my family and more time when I’m not obsessing over some slight from someone. I feel pathetic to admit that I had that problem. But I feel like an evangelical with some good news: you, too, can break free of the clutches of evil and immediately have a better life.

It is amazing how great it is to be far less active on Twitter. I can’t think of anything I’ve done in years (aside from getting married and having a kid) that has brought me so much concrete happiness so quickly. I’m not joking.

I do still use twitter. I post random thoughts. I find many people on twitter to have great thoughts when news breaks. And I probably type and delete 10 vicious attacks on my enemies every week. But I don’t send them. And that is great.

HW: You were co-founder and longtime co-host of Planet Money, one of the most successful podcasts out there. You’ve also hosted a podcast on Gimlet. What’s a “commonly held belief” in the podcast industry that you disagree with?

AD: Oh, boy. So, so many.

I guess the biggest one is that there is a thing called “podcasting” or the “podcast industry.” It is still such a vague, umbrella term that covers an enormous spread in quality and nature of content. We don’t talk about the  “video industry” to refer to everything from your cousin’s bar mitzvah video to some random unboxer on YouTube to Better Call Saul to the latest Marvel blockbuster. Similarly, we don’t talk about the “print industry” to refer to holiday cards, kids books, The New Yorker, and a Dan Brown thriller.  We recognize that video media and print media are divided into many, many categories and industries that barely overlap. They have different business models, different companies, different creators, etc.

Quality long-form audio was an obscure business a decade or, certainly, two decades ago. Very, very few people cared about it or learned how to do it. It strikes me that, over the first 40 years of a national public radio network, starting in 1970, there was a new big, successful, enduring long-form shows about once or twice a decade: Fresh Air and Prairie Home Companion in the 1970s, Car Talk in the 1980s, This American Life in the 1990s, Radiolab in the 2000s. There are others but not many.

There were other audio formats, of course. Talk radio was huge. Public radio also developed the magazine style show, comprised, mostly of short produced pieces of 3 to 5 minutes in length. But those short pieces and the magazine show have been largely irrelevant in podcasting. (This has been a pet peeve of mine for years, that NPR is still obsessively focused on the 3 minute reported story, which is entirely a terrestrial radio product. The skills required to produce a 3-minute story are wildly different from those required to produce a sustained podcast of, even, twenty minutes, let alone 60. Some can make the transition–like commercial directors who make movies–but many can’t.)

So, I think podcasting is going through a very natural maturation and segmentation right now. There are the equivalents of talk radio–Joe Rogan being the big hit. There are a bunch of great interview shows, especially WTF and How I Built This. And then there are the highly-produced shows, like This American Life, Serial, S-Town, and many of Gimlet’s shows, like Heavyweight.

I find, when talking to people without audio experience, they are not all that sensitive to the differences between these formats.

Highly-produced shows cost a fortune: tens or hundreds of thousands of dollars per episode. They are like quality TV, requiring highly skilled production staff and a business model that can reward that level of effort.

The high quality interview shows are much cheaper to produce, but their success is tied to a host who then has enormous bargaining power and can capture much of the profit, so it’s hard for big companies to make money from them (a fact I like!).

Then there are the many, many other podcasts–half a million or more–that really are more like blogs or twitter feeds. They are small, inexpensively produced content for a narrow audience of friends or a small business network. These are more like hobbies or business promotion tools and most disappear fairly quickly.

I would like all the people entering the space–from VC investors to big media companies and others–to understand the different segments or categories of podcasts, to recognize that each has a different path to listeners and profitability, and, most crucially, each requires a different sort of talent.

A very common mistake that has happened again and again is that somebody–a news outlet, a media company, a celebrity–decides they want a podcast but doesn’t recognize there are different segments of podcasting. They try to do something like This American Life and learn, too late, that there are not that many people in the world who know how to produce audio at that level of quality. It’s not like TV or movies, where there is a long-standing, massive ecosystem of DPs and editors and producers. There’s, like, 20 people who are true pros in long-form podcasting/audio production and pretty much every one of them has a job they like and isn’t going to do work for hire.  

There are some–though not that many–solid, experienced radio producers, mostly from public radio, who can do a solid, if unexceptional job. And there are thousands of young folks who are working hard to acquire those skills and many of them will, so this problem will solve itself eventually. But there are very, very few audio producers who can do work at the highest level, work that has repeatedly proven itself with audiences. So, right now, the demand for quality podcast production is far, far greater than the supply of podcast production talent. But many people don’t understand the vast gulf between different levels of talent and, so, they hire incorrectly and are disappointed and conclude that podcasting doesn’t work.  

Just as understanding of podcast production is immature, I think the podcasting business model is quite underdeveloped and too much of an ad-driven monoculture. I would expect subscriptions, long-term IP value creation, overlapping podcast universes–like Bill Simmons–and other models, familiar to Hollywood, will become more common in podcasting.  

This is self-serving, because I will say, obnoxiously, that I do see myself as one of that small group of veterans who has proven an ability to create compelling produced audio that finds an audience. Though I definitely am not at the top of that list. There are several folks who are much better than me. I started to list them but then realized I’d inevitably hurt someone’s feelings by not including their name. But I do think that, if you asked the people who have created podcasts that consistently stay in the top 10 or 20, they would all give you the same dozen or so names, again and again, as the top talent in the field.

One other and related misunderstanding/pet peeve: podcasting, of any sort, can’t just be a quick add-on to whatever else you’re doing. Don’t just buy a USB-mic for $50, record yourself and a friend for sixty minutes, and then wonder why nobody listens. I am launching a podcast in May and I–along with a team of three–have already spent several months and well over a hundred thousand dollars getting ready and we feel way behind. Good podcasts are as hard to make as any other creative endeavor.

I find the telling example is the many celebrities who have failed in the space. The ones who succeed: Chris Hayes, Rachel Maddow, Conan O’Brien, stand out because they didn’t rest on their fame and built-in audience. They spent time and effort and had real pros helping them.

HW: Given that more people know your voice than your face, how many times a year does someone stop you midsentance and say “i just realized why you sound so familiar!”

AD: It’s probably happened a half-dozen, maybe a dozen times in my life. I’m always shocked.  

Thanks Adam!