A Box of Rain Will Ease the Pain

While I’d been using the Internet since the early 1980s in my student job at Lawrence Berkeley Lab, the first time I remember using the worldwide web was in the mid 1990s. Well, August 9th, 1995, to be more specific.

I’d recently moved to Paris and heard about this layer atop the Internet that relied on hypertext transfer protocol to connect web browsers and web sites. Having seen what Apple had done with hypertext up that point, I wasn’t prepared to be impressed. So I fired up a browser and, to reconnect with home, I went to sfexaminer.com. The headline read:


“God, I hate this thing!” As an inveterate deadhead, the news was devastating if not entirely surprising. The episode set my web adoption back by a few years. While I won’t dive into my history following the band, I’ll show you the back of the car that we keep at our house in Oregon. (Morning Dew.)


Four years earlier, we’d lost the power in our Marin County home the night Bill Graham died in a helicopter crash west of Vallejo. If I was connected to Graham’s death via a power line, I was connected to Garcia’s via the web.

An SMS message connected me to last Friday’s death of Phil Lesh. Sent by a friend from so long ago that my phone no longer recognized his number, the news arrived as anonymous text message, containing only a link to the story.


I’ve written before (and as recently as three weeks ago) about business lessons from the Dead, so I won’t cover that again. Instead, as my tribute to Phil, I’ll write briefly about the power of metaphor using one of the relatively few Dead songs he wrote: Box of Rain. It’s also one of my favorites.

The song deals with Lesh’s feelings during the lingering, terminal illness faced by his father. Grateful Dead lyricist Robert Hunter worked with Lesh on the lyrics, and they are some of Hunter’s finest.

You can hear the frustration and impotence in battling illness via lines like:

“What do you you want me to do, to do for you, to see you through?”

The power and beauty of the song, however, comes from the primary metaphor: the box of rain.

“Just a box of rain, wind, and water. Believe it if you need it, if you don’t just pass it on.”

But what is this box of rain? It’s a metaphor. In fact, it’s a metaphor within a metaphor.

Hunter was thinking along the lines of a “ball of rain,” but that was probably both too obvious and insufficiently poetic. So the ball became a box. (Hence, the inner metaphor.)

So what is this ball of rain, wind, and water?

It depends on perspective, and in this case you’re going to need a wide one. Seen from far enough away, that ball of rain is our home. The earth.

“It’s just a box of rain, I don’t know who put it there. Believe it if you need it, and leave it if you dare.”

Once you understand the metaphor, that’s pretty literal.

“And it’s just a box of rain, or a ribbon for your hair.”

Hunter loved to write about certain things, such as calliopes and ribbons. While hard to interpret, I think this line is another metaphor. What do ribbons do for hair? Make it more beautiful. What does the box of rain do for the universe? The same thing. The earth is just a ribbon in the hair of the universe.

It adds a sense of utter smallness, rivaled only by how Tralfamadore used the earth in The Sirens of Titan.

(I feel obliged to say that Hunter hated to interpret his lyrics, maintaining that it wasn’t about what the words meant to him: it was about what they meant to you. He didn’t want his meaning to ruin your meaning. At first, the puzzle-solver in me found this offensive, but over time I’ve come to realize that it’s actually pretty cool.)

Now we’re ready for the last line.

“Such a long, long time to be gone and a short time to be there.”

There, of course, being here. On our box of rain. In this life. On this earth.

Thank you Phil for always putting the music first, the culture, and the reminder. May we all spend our time here as well as you spent yours.

The Impact of AI on SaaS Metrics: Video Now Available

Just a quick post to highlight that the good people of Benchmarkit, host of SaaS Metrics Palooza 24, have posted the video of my presentation, The Impact of AI on SaaS metrics. The slides are here.

Design Your Organization for the Conflicts You Want to Hear About

Organization design seems a popular topic these days. Maybe it’s the downturn. Maybe it’s just planning season. But either way, many people are asking me questions about how to design their organizations for 2025 and beyond. Questions like:

  • Should marketing report into sales?
  • Should engineering and product management (PM) report into a combined product org?
  • Should we unite customer success and sales?
  • Should North American and Europe report into a single head of sales?

The argument for combining teams is always about reducing span of control. This is a goal that many CEOs (and some boards) share, but one that somehow escaped one of the world’s most successful entrepreneurs, Jensen Huang, who has about 60 direct reports.

While 60 seems a bit much, I’ve frankly never understood span-of-control reduction as a top organization design goal. As CEO, you should be managing senior people so they shouldn’t take that much time. So, why not have 8 or 10 direct reports? If you can’t handle that, maybe the problem isn’t that you have too many reports, but that you’re managing them too closely. Maybe the solution isn’t to reduce their number, but to loosen the reins.

I have two rules for organization design:

  • Design for conflict. Specifically, design your organization for the conflicts you want to hear about.
  • Ensure value-add. Don’t put thing B under thing A unless the executive in charge can add value to both.

Design for Conflict

When you put, for example, engineering under product, what don’t you hear about anymore? Conflicts between PM and ENG about the time and resources required to build things. Those conflicts get silenced because the SVP of Product will suppress them, resolving them in the family.

When you put marketing under sales, what don’t you hear about anymore? Conflicts about whether sales strategy is too unfocused to enable marketing targeting. Or whether sales follows-up on new oppties in a timely manner. Those get silenced because the CRO wants to manage their own house. “Let’s resolve that at the sales QBR, not the e-staff meeting.”

When you put customer success under sales, what don’t you hear about anymore? Conflicts about whether sales is overselling to the point that customers won’t be successful and ergo won’t renew. If churn looks high, well, it must be the product. It’s not delivering, but against what expectations, set by whom? All silenced.

The rule is simple. By combining two departments, you are asking one person to resolve the conflicts between them. They’re not evil to do so; it’s the job you asked them to do. They will keep these conflicts in the family. And, as the organization grows, you will hire increasingly senior people to do just that. But with each layer and with each combination, you get more insulated from the ground truth.

So the question is simple: which conflicts do you want to hear about? Which do you want to pay someone else to resolve and which do you want brought to your office? Which are strategic to the company and potentially involve Crux-level issues?

  • If you separate PM and ENG, you’ll hear a lot about specs, resources, and timelines.
  • If you separate sales and marketing, you’ll hear a lot about awareness, leads, and follow-up.
  • If you separate customer success and sales, you’ll hear a lot about over-selling.

There’s no magical answer here. Just a framework for thinking about it. Determine the conflicts you want to hear about — presumably because you can add the most value in resolving them — and then design the organization to make sure you do.

Ensure Value-Add

The other principle is to always ensure value-add, beyond the (sometimes merely assumed) alignment that comes from having a common boss. So, sales wants the SDRs to report to them? Why? Has the sales VP managed an SDR team before? Are they good at it? Are they even interested in it? Can they add value? Are they sufficiently metrics and process-oriented, particularly if the VP comes from an enterprise background?

This principle drives a number of positive effects:

  • It defeats empire building. Sometimes the VP wants the SDR team not because they care about them, but because they want a bigger organization. Or they think it will look good on their resume for their next job search. They’re not actually interested in the job. They’re interested only in being able to say that they did it. That’s not good enough.
  • It encourages learning and development. When the VP of sales first asks about managing the SDRs, you can tell them to go make themselves a valid candidate. Get close to the SDRs now. Understand their challenges and offer to help out. Network with friends and colleagues on SDR team management. Read up on best practices. Convince me that you’d make the short list of candidates and then we can have a conversation.
  • You attract stronger department heads. Everyone should work for someone they can learn from. Saying the boss is the boss because, “well, we had to plug the team in somewhere,” is a terrible reason for an organizational structure. If you apply the value-add rule, functions will tend to report higher in the chain, creating a flatter org, and be placed only under those who can add value to them. This, in turn, attracts stronger candidates to run them. Who wants to be the CMO when it reports to a CRO who understands nothing about marketing? Nobody.

One great example is whether the VP of European Sales should report to the existing VP of Sales when you expand into Europe. If your VP of Sales is clever, they’ve already given themselves the title “VP of Worldwide Sales,” and you let them do it because it was moot at the time. But now they’ll argue it’s a demotion if Europe doesn’t report to them. And they’ll argue that they know how to sell the software in North America (really, the USA) and that knowledge should translate anywhere. And that everybody does it this way. You can almost hear them screaming: pick me, pick me!

But what they should be screaming is: I can add value, I can add value! And if they can, you should listen. But my questions would be:

  • Do you have a passport? (This wipes out about half of Americans.)
  • Have you ever lived in Europe?
  • Do you speak any European languages?
  • Have you ever sold and/or managed people in Europe?
  • Do you you have a network of people we can hire in Europe?
  • Do you have relationships with contacts at target customers in Europe?
  • Do you know any strategic partners we can work with in Europe?

So, other than not having a passport, never having been there, knowing no one, and not being able to communicate, you strike me as an outstanding candidate for the job.

We do this all the time nevertheless, and Europeans have grown accustomed to reporting into people who can’t add value. But for my nickel, I’d rather hire a VP of EMEA who had great answers to my questions and reported directly to me.

Mitigation Strategies

As your organization grows, you will invariably combine teams and lose your line of communication into certain conflicts. I know three ways to mitigate this:

  • Build a culture of transparency where direct reports into e-staffers are encouraged to and rewarded for speaking frankly about in-the-family problems.
  • Run an extended QBR. Don’t just invite the e-staff to the quarterly business review, but also invite people among their direct reports. For example, the head of customer success if it reports into the CRO, or the head of engineering if it reports into product. Ask them to deliver the same, standard presentation that the e-staffers do. This effectively flattens the organization by creating an extended leadership team that goes beyond the CEO’s direct reports.
  • Use reporting. Good reporting can reach through organizational layers and keep you in touch with what’s happening. For example, even if customer support doesn’t report to you and isn’t represented on the extended leadership team, you can still keep an eye on metrics and KPIs as well as simply on OKRs.

In this post, I’ve argued that the primary goal in organization design should not be reducing of span-of-control, but in surfacing conflicts most important to the company. I’ve also introduced a value-add rule that says no department should report into an executive who can’t add value to it. And finally, knowing that consolidation is inevitable over time as a successful company scales, I’ve offered three strategies to mitigate some of the signal loss that comes with such expansion.

Slides from SaaS Metrics Palooza 2024: The Impact of AI on SaaS Metrics

Just a quick post to share my slides from today’s presentation at SaaS Metrics Palooza 2024, entitled The Impact of AI on SaaS Metrics.

The short summary is:

  • The concept of ARR is already challenged by monthly-varying pricing, e.g., usage-based pricing.
  • AI will exacerbate that problem, bringing new forms of value-based pricing, e.g, unit-of-work or outcome-based pricing.
  • There are two schools of thought on dealing with this: (1) split the ARR baby into baseline and variable, then analyze the baseline as if nothing has changed, and (2) spend is truth, where we substitute trailing spend for ARR. I’m in the second camp.
  • AI will, gasp, require us to think about cost, something we don’t really like to do in the software business and something we’ve historically been able to kind of ignore.
  • All the heavy lifting is going to move to the pricing model.

In short, to know ARR we used to read contracts. In the future, we’re going to read invoices, instead.

Yes, for internal reporting we will do a lot of pricing model analysis and examination of the base/variable split. But for external reporting, the big six SaaS metrics all depend on ARR and going forward that won’t change. We’ll just use some proxy for ARR, as many quietly do already today.

Like a duck, nothing will change much on the surface, but they’ll be a lot of activity underneath. And the metrics won’t mean quite the same thing as they once did. For example, ARR and NRR will become less forward looking and work less well as leading indicators.

I’ve embedded the slides below.


You can download a PDF of the slides here.

Thanks for coming!

Marketing Lessons from the Grateful Dead by Scott and Halligan: A Belated Book Review

Since It Costs A Lot to Win, and Even More to Lose [1]

It’s hard for a DNA-level marketer and inveterate deadhead [2] to review a book that fuses both. While I first read Marketing Lessons from the Grateful Dead not long after its publication in 2010, I’d never wanted to write about it. There was too much to say, the subject too close to home, and the Dead were becoming passé anyway — who’d want to learn lessons from a band that supposedly peaked on 5/8/77 and that played its last show on 7/9/95?

Since then, three things happened:

  • Since 2015, John Mayer has breathed new life into the band, bringing new and younger fans to the community. Dead tribute bands blossomed and now play at swanky Nantucket venues [3]. My son started to borrow my old t-shirts to attend NYU college parties. Unexpectedly, the Dead became cool again.
  • I internalized that one of the authors, Brian Halligan, was the founder/CEO of HubSpot and that should, well, automatically make the book significant. [4] [5]
  • I recently had a series of conversations with Jacquelle Amankonah Horton, the dynamic founder of Fave, where I found myself talking about community to someone in the music business, something I find pretty much impossible to do without talking about the Dead. Those chats re-energized me on the whole topic.

So here we are. Let’s do my long overdue review of Marketing Lessons from the Grateful Dead.

Before diving in, let’s note that this book is not the only attempt to take business lessons from the Dead. Other notable efforts include:

Once in a While You Get Shown the Light in the Strangest of Places [9]

So, does this book show us the Dead’s marketing light in a way that can be applied more generally to business? Yes. It does. Though, to split hairs, I’d argue it’s more a book about strategy than marketing [10].

The book is structured in three sections. Each chapter discusses a principle from the Dead and a company that demonstrates the principle. While the chapters-as-lessons structure works, the consistent alternation between principles and examples makes the book feel somewhat formulaic. And, because tech changes a lot in 15 years, while the principles are timeless, the examples are often not (e.g., Mashable, MySQL, StumbleUpon) [11].

The first section takes lessons from the band:

  • Create a unique business model. The Dead made money selling tickets, not albums. This was, and is, pretty unusual in the music business.
  • Choose memorable brand names. The Grateful Dead is a memorable name, and far superior to their previous one, The Warlocks.
  • Build a diverse team. The musicians came from different backgrounds. Garcia loved bluegrass, Lesh was trained in classical jazz, and Pigpen was a blues harmonica player. You can get a 1+1 = 3 effect from the fusion.
  • Be yourself. The Dead were authentic in general and transparent about mistakes.
  • Experiment, experiment, experiment. A product of the Acid Tests, the band was born experimental and improvisational. They were always trying new and creative things (e.g., a song in 11/8 time).
  • Embrace technology. The most notable example was The Wall of Sound, a 600-speaker public address system that delivered unparalleled sound quality (and took four semi trucks to carry), but quickly proved impractical for a touring band [12] [13].
  • Establish a new category. The Dead defined a new category of music, which only after several decades got a name (“jam bands”). They were very much a category creation story [14].

The second section takes lessons from the fans:

  • Encourage eccentricity. Eccentricity was embraced by the band and its fans, allowing everyone to be themselves.
  • Bring people on an odyssey. The Dead, starting with a mailing list hooked to a San Rafael post office box, made fans an equal part in the journey (aka, the long strange trip).
  • Put fans in the front row. The band set up their own direct ticketing operation to ensure fans fair access to tickets [15].
  • Build a following. The Dead were pioneers in database marketing (and subsequent techniques) to cultivate the fan base.

The last section takes lessons from the business:

  • Cut out the middleman. Their direct ticketing operation not only enabled fair access, but it reduced costs, allowing the band to gross 100% of ticket sales.
  • Free your content. The Dead allowed fans to tape concerts, nearly unique in the industry, and an open source approach that helped new fans enter the scene.
  • Be spreadable. Concert tapes became collectibles that were copied and traded [16], whether between individuals or in Shakedown Street swap meets before and after shows.
  • Upgrade to premium. While the band allowed taping, they nevertheless released live albums, with amazing sound quality such as Europe 72 or Skull and Roses [17].
  • Loosen up your brand. While the Dead had standard icons, they defined a broad visual style and allowed improvisation within it. Contrast this to typically strict corporate branding style guides that stifle creativity in the name of consistency [18].
  • Partner with entrepreneurs. Rather than ban the use of their imagery, the Dead licensed it to entrepreneurs who could make and sell their own merch.
  • Give back. From benefit concerts to community support to the Rex Foundation, the Dead gave back, long before it was corporate-fashionable to do so.
  • Do what you love. My survivor bias detector triggers whenever I hear this, but the book’s point is more fundamental: if they didn’t love what they did, they couldn’t have kept doing it for more than 2,300 concerts.

Sometimes We Walk Alone [19]

When writing about the Dead, most people capture the contrarian, rule-breaking nature of the band. It’s hard to miss. The book does that and extracts 19 individual lessons that can be taken from the Dead’s success. Frankly, I’d have preferred if they took fewer lessons and examined them in more depth, as does Everything I Know About Business I Learned from The Grateful Dead.

What the book really misses, however, is the strategic consistency across the lessons. Using the language of Richard Rumelt, the book notes 19 different actions undertaken by the Dead, but fails to recognize that they are coherent actions driven by an overall guiding policy. Much as Costco works spectacularly well not because of the fifty things they do differently, but because of how those fifty things work together, so it is with the Dead.

The improvisational format means every show is different. That enables fans to attend consecutive shows, which enables fans to tour with the band, which in turn enables the Shakedown Street tailgates and community. The ability to tape concerts combined with the improvisational format means that each show is unique and ergo recordings become collectibles, further enabling the community. Licensing merchandising rights to small vendors enables the tailgate scene and nomadic vendors, who can effectively earn a living touring with the band (and using proceeds to buy tickets). Commitment to fan experience means playing small venues, and improvisational shows enables playing small venues for consecutive nights. This enables the community scene while the direct ticket operation keeps ticket prices reasonable despite the restricted supply.

You can allow taping, but if every show is the same, the tapes won’t be valued. You can play small venues, but if you don’t control ticket sales, pricing will box out your best fans. You can play in an improvisational format, but if you don’t repeat nights at venues and move in slow and systematic fashion, you won’t enable fans touring with the band and the community parking lot scene.

It is not any one of the lessons that matters. It is the strategic consistency across them that creates the magic.

Switching to Blue Ocean Strategy as my strategic reference, the Dead re-invented rock music in the same way that Cirque du Soleil re-invented the circus. They took the fundamental levers of the business (what the authors call a strategy canvas) and reset them to create an entirely different type of product.


For the Dead, this is best reflected by the old deadhead saying, “there is nothing like a Grateful Dead concert.” That’s because the levers are set differently.

Come and Join the Party

I’ll conclude with the original invitation to the Grateful Dead party: the first verse of The Golden Road to Unlimited Devotion, the first song of their first album. A song about The Summer of Love [20].

See that girl, bare-footin’ along,
Whistlin’ and singin’, she’s a carryin’ on.
There’s laughing in her eyes, dancing in her feet,
She’s a neon-light diamond and she can live on the street.
Hey, hey, hey come right away.
Come and join the party, every day.

That invitation, some 57 years later, remains open.

# # #

Notes

[1] Opening line of Deal, an upbeat song in the band’s Americana catalog. Guitar players (or those interested in music) should check out this Guitar Teacher Reacts video by Michael Palmisano.

[2] 300 or so shows and counting, including all variations.

[3] I’ll refer to the Dead as a capstone term for The Grateful Dead, the Other Ones, The Dead, Furthur, Fare Thee Well, Dead & Company, and other variations. When a band is 50+ years old, you can end up with numerous incarnations.

[4] I knew it in 2010, but somehow forgot it over the years and was frankly surprised to rediscover it only fairly recently.

[5] And the co-author, David Meerman Scott, is no schmo. He’s a well-known marketing author and speaker.

[6] The general idea being that all strategy is improvisation because things change so quickly, and ergo that companies should view strategy as structured chaos.

[7] “So can I go into the show,” to complete the famous fan quote from the The Grateful Dead Movie.

[8] Surprisngly, two of the three authors were at the Theoretical Division, Center for Nonlinear Studies at Los Alamos National Lab. Technically, this paper isn’t really trying to extract business lessons from the Dead, but I think we find one anyway in that fundamental tension, which in software would be expressed by “what we want to build” vs. “what they want to use.”

[9] One of the most-quoted Dead lyrics, from Scarlet Begonias. The complete line is “once in a while you [can] get shown the light, in the strangest of places if you look at right.” In 1976, they inserted the [can], which subtly changed the meaning, for the worse in my opinion. But to demonstate the depth of the Dead rabbit hole, go to the Good Old Grateful Deadcast for a two-hour exploration of this one song.

[10] Strategy is a little tricky to classify. Corporate strategy is definitionally company-level and I’d classify most of the lessons in this book as corporate strategy, not marketing strategy. For those who consider corporate strategy formulation a marketing duty (and I’m one of them), remember that marketing (or corporate development) typically drives the strategy formulation process (e.g., the offsite, the agenda, the topics, the pre-reading and data). But driving the process and “owning strategy” (i.e., its result) are two different things.

[11] Timeless principles can hopefully be illustrated with timeless examples. They did this in cases (e.g., Ronald McDonald house), but perhaps the temptation to use hot contemporary examples (that invariably date the work) was too strong. Songwriters face the same tension and Dead lyricist Robert Hunter did a fantastic job of resisting it, writing timeless lyrics as a result. In fact, the famous spat that ended collaboration between Hunter and Bob Weir was over Weir’s insertion of “Jump like a Willys in four-wheel drive” into Sugar Magnolia. Hunter strongly objected, I’m guessing, not only for artistic reasons, but because it would date the lyrics.

[12] A short video overview of the three-story Wall of Sound is provided here.

[13] Some enthusiastic fans recently built a half-scale wall of sound.

[14] Dispelling the myth that the category name matters enormously. Focus on building the category, the name can come later.

[15] While Billy Joel never tried to disintermediate ticket sellers, he does seem to have a fans in the first row policy as well. Few others do.

[16] In the analog tape world, copying was not lossless, so tapers would careful try to track the “generation” of the tape (original, copy, copy of copy, etc.)

[17] The amazing quality was achieved not only through high-quality audio equipment, but also through some level of studio doctoring of the recordings, e.g., overdubs.

[18] My definition of visual branding is: do we look like us? Attaining this goal is typically done via strict standards, but a few organizations manage to define a broader look and allow innovation within. The Dead were great at this. Salesforce does a pretty good job as well.

[19] From Eyes of the World.

[20] The Golden Road to Unlimited Devotion. The Summer of Love was also the inspiration for the more famous, San Francisco Be Sure to Wear Flowers in Your Hair by Scott McKenzie, and one far more famous song than that, All You Need Is Love by the Beatles.