A Quarter-Century After 9-11

“The world we see today is far different from that of September 10, 2001. On that day, who could have predicted that both New York and London would have radical Muslim mayors? That a real estate developer would be in the White House? That antisemitism would become a trademark of the Left and that the U.S. would be on the leading edge of technologies which weren’t even conceived at the turn of the 21st century? We have gone from a world that thought it knew where it was going to a journey in the dark.”

Richard Fernandez “September 10, 2001“

Watching People Jump Off the Twin Towers

The morning of 9-11 was completely disorienting: watching the first tower collapse seemed like a special effect. When the second one went, I had the strong sensation I was a minor character in a Tom Clancy novel. A number of us gathered in a training room that was not being used so that we could watch a working TV. It was working to the extent it could get a Spanish channel, but only a Spanish channel for reasons that none of us could figure out. The most chilling scenes that they played over and over but which I did not see on any network or US cable channels when I got home were those of people jumping off of the towers before they collapsed. I was reminded of an old movie, “The Towering Inferno,” and I kept thinking there must be a way to put that fire out or get those people off the roof. But no happy Hollywood was ending to be found.

From “Do You Ever Get The Feeling Everything You Know is Wrong?” (2018)

Anybody who survives the impact, we’ll go to an alternate center, and we’ll continue.

Lewis “Scooter” Libby, chief of staff to Vice President Dick Cheney: We learn that a plane is five miles out and has dropped below 500 feet and can’t be found; it’s missing. You look at your watch and think, Hmmm, five miles out, 500 miles an hour. Tick, tick, tick.

Dick Cheney: My Secret Service agent said, “Sir, we have to leave now.” He grabbed me and propelled me out of my office, down the hall and into the underground shelter in the White House.

Mary Matalin: My jaw dropped and the jaws of my colleagues dropped because we had never seen anything like that.

Condoleezza Rice: The Secret Service came in and they said, “You have got to go to the bunker.” I remember being driven along, almost propelled along. We had no idea where it was safe and where it wasn’t. We didn’t think the bunker of the White House was safe at that point.

Dick Cheney: They practice this—you move, whether you want to be moved or not, you’re going.

Gary Walters: The Secret Service officers started yelling, “Get out, get out, everybody get out of the White House grounds.” I remember early on, the chaos. People running, screaming. Fear was in my mind.

Christine Limerick, housekeeper, White House: The look on the faces of the Secret Service agents who were told that they had to stay—I will never forget that because we had at least the opportunity to flee.

Ian Rifield, special agent, U.S. Secret Service: We were fairly confident that plane was going to hit us. The supervisor in the [Secret Service’s] Joint Operations Center basically said, “Anybody who survives the impact, we’ll go to an alternate center, and we’ll continue.” It wasn’t a joke.

Garrett M. Graff (@vermontgmg) “The Only Plane in the Sky: An Oral History of 9/11

There was a mindfulness in Silicon Valley after 9/11 and the dotcom crash that I miss.

“There was a mindfulness in Silicon Valley after 9/11 and the dotcom crash that I miss. I don’t miss the terrible turmoil and the anxiety and the 25% contraction in employment, but I do miss the mindfulness. I remember attending a Churchill Club program “Beyond the Bubble: the Future of Technology and Investing” that was held on September 20, 2001; it was a little over a week since 9/11 and there was a minute of silence to memorialize the dead that lent a candor to the program that followed. Edward Howe has observed that “a good scare is worth more to a man than good advice” and that was true in late 2001 and 2002 in Silicon Valley.”

Lesser Sons of Greater Fathers

Related Blog Posts

• Reclaiming Nine-Eleven
• 9-11 at Twenty-Two
• 9-11 Twenty Years Later: An American Cultural Watershed
• 9-11 at 19: Looking back at a Unified America
• On That Day: 9-11 Eighteen Years On
• Thomas Schelling on Strategic Surprise
• Do You Ever Get the Feeling That Everything You Know is Wrong?
• If You Predict Rain, Build an Ark”
• Pearl Harbor to 9-11 to the Panopticon
• Lee Harris’ Insights on What 9-11 Means
• Second Sight: A Meditation on Silicon Valley and 9-11
• Remembering 9-11: Our Children Will Also Live in Interesting Times
• Take a Minute To Remember 11 Years Ago
• Remembering What Happened
• Take a Minute To Remember 9 Years Ago
• Take a Minute to Recall 8 Years Ago, Part 2
• Take a Minute to Recall 8 Years Ago
• Lesser Sons of Greater Fathers

Q: How Do Early Employees Get Founders to Listen?

Q: I am in my second full-time job; it’s my first time in a startup. I spent two years at a software firm with three hundred employees and absorbed insights into developing and shipping features. The startup has only a dozen people, and it moves faster but is much more disorganized. I have been involved in interview rounds for new employees that were poorly managed. That was frustrating, but what has been more frustrating is that no one seemed to see the problems. As a result, they were not open to my suggestions.

A: A startup with a dozen people is starting to gain some structure but can still be a wild ride, especially if there are not many experienced employees. The decision of who to hire is a critical one in a startup, as is the need to assess a potential candidate’s capabilities and fit with the team. It’s also the case that interviews are an opportunity to encourage qualified candidates to feel welcome and wanted.

It’s entirely possible that you had some good suggestions and should have been listened to but it’s also possible you don’t understand all of the constraints on what’s possible. While initiative and frank talk are expected, if not required, of early employees in a startup, most change is incremental and the result of patient persuasion and appeals based on organizational survival or robustness.

Since you are newly hired and have only two years of work experience, you probably have less work experience than many others on the team. I suggest a more indirect approach. Who, outside of the founders, has the most experience with managing an interview process? Can you talk to them one-on-one and get feedback on your suggestions? Ask how the process was defined and whether they see the same problems today that you do. This approach is likely to work for other areas as well. At a dozen people, the organization is in transition from a flat structure to one or more levels of hierarchy; it’s important to recognize who may be responsible for an issue or decision besides the founders and approach them first.

Different people absorb information in different ways. Some on the team may prefer numbers related to time savings or financial impact. Others may prefer stories or case studies, either in writing or in a conversation. Presenting to a group can be hard, so it helps to write down your suggestion, rehearse it, and have one-on-one conversations first with people who may be more willing to give you feedback or ways to improve your presentation.

In “On Being a Teacher,” Jonathan Kozol offers a perspective on managing learning challenges I have found valuable:

“Struggles that we and our students hope to undertake ought to be measured by their value, on the one hand, and real chances for completion on the other: Battles large enough to matter, small enough to win.”
Jonathan Kozol in “On Being a Teacher”

This often gets condensed into “Pick battles big enough to matter, small enough to win,” but I find his original compelling since it is clearly focused on learning.

My assumption is that you don’t feel you are being asked to compromise your values. If you do feel that, then it’s probably better to look for work at a company you believe is more aligned with your values.

SideBar: Some Traits to Develop for Success as an Early Employee

In “Working Capital: Assembling Your Team,” I suggested these key traits founders should look for in the first dozen employees:

• Experts in at least one area relevant to your business with a bias toward action: they can roll up their sleeves and get things done.
• Flexible contributors who can tolerate the irreducible uncertainties and ambiguities in a startup. They understand E. L. Doctorow’s insight that “Driving a car at night, you never see further than your headlights, but you can make the whole trip that way.”
• Constructive collaborators who communicate clearly, appreciate other points of view, spot defects in a plan or design, and suggest fixes.
• People who are willing to experiment and learn from the results, to manage multiple hypotheses and to look for complex causes and outcomes, balancing exploration and refinement to avoid premature optimization.
• People with a demonstrated commitment to continued self-improvement.
• People with a track record of taking the initiative to provide value to customers. Someone who bent the rules to do the right thing, or gave the customer the benefit of the doubt, or worked overtime when the customer situation called for it.

Related Blog Posts

• How to Influence Executive Decisions with Data
• Angel Rampy on Influence Skills for Technical People
• Orienting, Observing, Doing Homework, and Paying Dues
• Marshall McLuhan: How To See The Future
• Learning from John Perry Barlow’s Principles of Adult Behavior
• College Graduation: From Traveling Station to Station to Navigating a Borderless Sea
• College vs. Startup
• 12 From Sydney J. Harris’ “Winners and Losers” For Entrepreneurs
• Managing Change in an Organization: An Incomplete Resource List

Q: Overcoming Post-Acquisition Letdown

Entrepreneur: We sold our company a few months ago for roughly twelve million, and I netted almost two million. I am in my early 30s and not planning my retirement, but my wife and I have been planning to have children, and the money provides a lot of security. I am happy with the outcome, as better-funded competitors were slowly grinding us down. I look back on my journey with my cofounders and employees and consider it an absolute success.

But now I feel a strong sense of post-acquisition letdown.

We were a team of five and are now integrated into a team of 50 that is part of a big company in the same space. This is my first time working in a big-company environment, and it seems like all the jokes about it being incredibly slow are true.

AI has accelerated development across the board, and it feels like our slower pace means we are losing even faster to the competition. I continue to manage many of our older customer relationships, and every week another one cancels their subscription. We don’t have an earn-out as part of the acquisition, so it’s not affecting me financially, but it’s still incredibly frustrating. All the more because I cannot seem to do anything about it, I cannot get our development and product teams to take effective action. Is it normal to have such elevated churn after an acquisition?

I am under contract to stay another two and a half years, and the people I’m working with are great, but my motivation is starting to vanish. We used to work 60-hour weeks; now we work 40. The old way wasn’t exactly fun, but we had a sense of purpose that seems to be missing now. Now I find it hard to get up in the morning. I don’t plan to stay after the contract ends, but I have no clue what to do next.

I was elated when the deal closed, but now I am adrift. Any suggestions for how founders have navigated post-acquisition letdown?

Sean Murphy: You have 2.5 years to figure out what you want to to next. Take advantage of your current situation to learn how larger firms actually function as you may either sell to and/or compete with larger firms in you next startup. If you want children start now, it can take longer than you anticipate.

It’s completely OK to work only 40 hours a week, cultivate other interests and talents, and decompress. Write down your lessons learned, at some point you will need them. If you would like to share lessons learned at a Lean Culture event you are welcome to contact me directly.

Related Blog Posts

• How To Thrive After An Acquisition
• Wolfgang Huber Describes Bootstrapping Matrix Requirements
• Entrepreneurship’s Ups and Downs: Michael Risich shares entrepreneurship’s up and downs recounting his journey downs building a SaaS business and scaling to 10M in ARR.
• 7 Figure Solo Founder; What to Build, Delegate, Let Go
• eMOBUS Acquisition: How Bootstrappers Close Deals
• Founder Story: Acquisition Integration at 60 days
• Founder’s Story: An EDA Acquisition During the DotCom Boom
• James Jimenez on Exit Strategies for Startups
• Wine Management Systems Acquired by Process2Wine

Quotes for Entrepreneurs Curated In August 2026

I curate these quotes for entrepreneurs from a variety of sources and tweet them on @skmurphy about once a day where you can get them hot off the mojo wire. At the end of each month I curate them in a blog post that adds commentary and may contain a longer passage from the same source for context.

My theme for the August 2026 “Quotes for Entrepreneurs” is soliciting and responding to feedback.

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“Honest criticism is hard to take, particularly from a relative, a friend, an acquaintance or a stranger.”
Franklin P. Jones

This aphorism is also attributed to Jones: “Nothing produces such odd result as trying to get even.”

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“A Lean Canvas is not a plan. It is a list of everything you could be wrong about.
Nine boxes, all guesses, written in fifteen minutes.
The move is not to make them better guesses. It is to rank them by the cost of being wrong, then go test the one at the top.”
Ash Maurya

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“Life without industry is guilt, and industry without art is brutality: and for the words ‘good’ and ‘wicked,’ used of men, you may almost substitute the words ‘Makers’ or ‘Destroyers.'”
John Ruskin in “Lectures on Art: Delivered Before the University of Oxford in Hilary Term, 1870“

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“Some people have built-in filters that screen out the boos and amplify the hurrahs . Those are the people who never know when they’re in trouble.”
Tommy Davis, Venture Capitalist (quoted in “A kick in the seat of the pants” by Roger Von Oech)

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“Code never survives first contact with the users.”
Wally McClure (@wbm)

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“IF you shut your door to all errors truth will be shut out.

‘I HAVE lost my dewdrop,’ cries the flower to the morning sky that has lost all its stars.

What you are you do not see, what you see is your shadow.”

Three from Rabindranath Tagore in “Stray Birds“

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“The product of work isn’t only the work, it’s also the worker. Doing the work changes you; the up-close expe­ri­ence trans­forms your capa­bil­i­ties and even your desires. Insights and ideas emerge from that interface, and I believe the agent mae­stros lose a lot–too much–when they take their big step back.

I don’t merely want things done; I want to do them.”

Robin Sloan in “Fogbound“

h/t Marcin Wichary; emphasis in original. Sloan is making an important point: doing a task changes you, it gives you insights and skills that you don’t gain from just watching or delegating.

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h/t Jono Hey “The Wisdom Paradox”

“Wisdom tends to grow in proportion to awareness of your ignorance. When you come to see you are not as wise today as you thought you were yesterday, you are wiser today.”
Anthony Mello in “One Minute Wisdom”

Removing old errors, including misperceptions, misunderstandings, mistaken beliefs, and false assumptions, is a key skill for entrepreneurs. Many assumptions you make when you start are incorrect.

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“Every calamity is a spur and valuable hint.”
Ralph Waldo Emerson “Fate”

A calamity is feedback of a sort if you take the time to learn from it.

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“haec quae nocent docent”
Latin proverb: Those things which hurt also teach.

It’s hard to thread the needle: you often need to iterate to tinker with and refine your approach so even if an approach does not work the first time it’s worth trying a few variations before abandoning it. On the other hand you don’t want to keep making the same mistake over and over. Persistence pays off but you have to vary your approach: most problems are combination locks so that even if you are two thirds correct you may make no progress.

I originally curated this in April 2019 and explored the concept of “retry, vary, or make a change” in July of 2012.

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While there is a lot of truth to the proverb that “There is no growth without pain,” it’s also true that there can be pain without growth. As entrepreneurs we focus on bringing change but there is a risk that we waste a customer’s time and effort, or even leave them worse off, if we are not careful.

“Take care. It is so easy to break eggs without making omelettes.”
C. S. Lewis in “Letters to Malcolm”

I originally curated this C. S. Lewis quote in May 2024

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“Strategy is a system of expedients; it is more than a mere scholarly discipline. It is the translation of knowledge to practical life, the improvement of the original leading thought in accordance with continually changing situations.”
Helmuth von Moltke the Elder, “On Strategy” (1871).

I like von Moltke’s suggestion that a strategy is not like pouring the foundation of a building and never adjusting it; instead, it should be improved “in accordance with continually changing situations,” which is also known as responding to feedback (or new realities, as the case may be). Experienced entrepreneurs learn that no plan survives contact with customer feedback and competitor responses.

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“Significant changes in human behavior can only be brought about rapidly if the people expected to change actively participate in deciding what that change will be and how it will be made.”
Herb Simon “Recent Advances in Organization Theory” (1955) in “Research Frontiers in Politics and Government”

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“Momentum grows faster than motivation.
Amateurs get ready; professionals get started.”
Mark Manson (@Markmanson) (May 19, 2026 tweet)

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“The most successful people I know don’t think of their career as a ladder. But rather, a jungle gym. They make sure that their vision is always peripheral so that they can see opportunities that come along—and swing to them. ”

Patricia Sellers in “Get Used to the Jungle Gym” (2009) [paywall]

I like this metaphor and it’s emphasis on the need to not only look up, but look around. It reminds me of a line by Francis Bacon,”All rising to great place is by a winding stair.” It’s from his 1625 essay, “Of Great Place”  (1625). Guy Kawasaki riffs on this metaphor–without crediting Patricia Sellars–in “Careers are Jungle Gyms Not Ladders”

Most career advice still assumes a ladder. You start at the bottom, climb rung by rung, collect better titles, more money, and more authority, and eventually arrive somewhere called “the top.”

It’s tidy, linear, and reassuring. It suggests that progress is vertical and that success is simply a matter of climbing steadily upward. It’s also a poor description of how real careers actually unfold.

Real careers look more like jungle gyms. You climb up, move sideways, drop down, hang upside down for a while, and sometimes jump across to something new entirely. Progress isn’t measured only by elevation, but by agility, strength, and perspective. The value comes from how many dimensions you can move in, not just how high you can go. […]

The most durable careers are built by people who optimize for strength instead of height. They focus on building capability—judgment, communication, resilience, pattern recognition—because those skills travel with them no matter where they climb.

Titles expire. Strength compounds.

If you invest in learning how to adapt, collaborate, and recover from missteps, you’re not dependent on a single company or industry to validate you. You can grab a new bar when the old one disappears. […]

Pay attention to where you’re growing, where you’re coasting, and where you might need to shift direction. The goal isn’t constant ascent. The goal is to keep developing the strength and flexibility to move with confidence.”

Guy Kawasaki “Careers are Jungle Gyms Not Ladders“

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“Any attempt to manage human beings needs to take into account that our evolutionary history is weighted towards surviving in small bands of savannah-dwelling hunter-gatherers.”
Byrne Hobart in “Open Thread 195” (Aug-15-2026)

.

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“I am an enthusiast, but not a crank in the sense that I have some pet theories as to the proper construction of a flying machine. I wish to avail myself of all that is already known and then if possible add my mite to help on the future worker who will attain final success.”

Wilbur Wright in a May 20, 1899 letter to the Smithsonian Institution requesting available publications on human flight.

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“Among the well-know phenomena of group dynamics is the alacrity with which members of a cohesive in-group suppress deviational points of view by putting social pressure on any member who begins to express a view that deviates from the dominant beliefs of the group; this pressure often takes the form of urging the dissident member to remain silent if he cannot match up his own beliefs with those of the rest of the group.”
Irving Janis in “Victims of Groupthink” (1972)

It’s a tricky problem because you want your team to be cohesive and work within effective norms, but the realities of early-stage startups require a full and frank exchange of views.

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“Just calling it “feedback” doesn’t mean that it has actually fed back. To speak precisely: it hasn’t fed back until the system changes course. Up to that point, it’s merely Sensory Input.”
John Gall in Systemantics: The Systems Bible

The best feedback for early-stage startups is direct input from prospects and customers, either in conversation or email. Surveys can impose a structure that screens out feedback that might surprise you, and is therefore the most useful. However, you should only ask questions or seek feedback you are prepared to act on. Gall warns later in Systemantics that, “A system that ignores feedback has already begun the process of terminal instability.”

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“Entrepreneurs are always taking feedback, especially from their customers, bankers, workers, and sales force. Without straightforward feedback, entrepreneurs cannot make sound decisions.”

Donald Trump and Robert Kiyosaki in Midas Touch

This is from a section credited to Robert Kiyosaki.

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“Information about past behavior, delivered in the present, which may or may not influence future behavior.”
Gerald Weinberg in “Quality Software Management. Vol 3. Congruent Action”

This is Weinberg’s definition of “feedback.”

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“When there are long delays in feedback loops, some sort of foresight is essential.”
Donella Meadows in “Thinking in Systems”

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“If you want to create the common sense that comes from twenty years of being in the world, you need to devote twenty years to the task. You can’t assemble an equivalent collection of heuristics in less time; experience is algorithmically incompressible.”
Ted Chiang in The Lifecycle of Software Objects [online text at Subterranean Press]

In “Marcelo Rinesi: The Expertise Light Speed Barrier” Marcelo Rinesi makes much the same point about fundamental limits on acquiring expert knowledge that Chiang offers as “experience is algorithmically incompressible.”

Much of common sense is plain dealing with other people: effectiveness here flows from developing the right values early.

Entrepreneurs are resistant to peer pressure; they can tolerate being viewed as an outlier and persist in the face of many people who see them as wrong. This serves them well when bringing revolutionary ideas and systems to market, but it can mislead them when it’s a values mismatch with a community.

There is an important distinction between feedback that says, “your idea is won’t work” and “you are acting in ways that are dishonest, deceptive, manipulative, or untrustworthy.” You should understand why the person is giving you either kind of feedback, but it’s rarely a good idea to ignore the latter.

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“A lean canvas is not a business plan. It is a list of everything you are betting on, in an order you can attack.”
Ash Maurya (@ashmaurya) in an Aug-25-2026 tweet

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“I discovered that starting a business is as much an act of self-expression as it is a professional one. I found that our beliefs, energetic patterns, and our thoughts manifest themselves in our careers in ways that I couldn’t have imagined. I also realized that many of us feel the need to bring more spiritual consciousness into the workplace, so that each of us can contribute to the world in ways that are more self fulfilling and holistic.”
Riz Virk in Zen Entrepreneurship (revised edition)

I like this  quote. It’s certainly a good idea to pay attention to your intuitions about people and situations, but I did not like the “business fable” format of  Zen Entrepreneurship and overall found it more mystical than practical. Rizwan Virk has an excellent book, Startup Myths and Models, that is factual, practical, and insightful. He fell short of the mark on this here. I also found his composite character, Ramaswami, frankly unbelievable.

Jon Winokur wrote a great biography of James Garner called “The Garner Files: A Memoir” that does a good job of explaining how Garner relied on “luck” and intuition in his career. Winokur does into some detail about how Garner also relied on careful observation and cultivated habits that led to his “luck.”

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“The trick to viewing feedback as a gift is to be more worried about having blind spots than hearing about them.”
James Clear (@JamesClear) Dec 15, 2020 tweet

Successful founders compare notes frequently with other entrepreneurs, form advisory boards, and join a Mastermind group so that problems and blind spots are uncovered by a friendly fire before a competitor can exploit them.

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“Even the most basic CEO building blocks will feel unnatural at first. If your buddy tells you a funny story, it would feel quite weird to evaluate her performance. It would be totally unnatural to say, “Gee, I thought that story really sucked. It had potential, but you were underwhelming on the buildup and then you totally flubbed the punch line. I suggest that you go back, rework it, and present it to me again tomorrow.” Doing so would be quite bizarre, but evaluating people’s performances and constantly giving feedback is precisely what a CEO must do. If she doesn’t, the more complex motions such as writing reviews, taking away territory, handling politics, setting compensation, and firing people will be either impossible or handled rather poorly.”

Ben Horowitz in “The Hard Things about Hard Things“

Founders must set performance standards based on what customers value and hold everyone on the team, including themselves, accountable. Because everyone has blind spots, they must solicit feedback on their own performance from other team members, partners, prospects, and customers. This wider perspective can also detect team-level blind-spots. Founders must act on this feedback, or the ask will become a performative ritual. The key is to understand what customers value and to pull that assessment into day-to-day decisions and procedures to minimize potential customer dissatisfaction, which can lead to sales that don’t advance, failed trials, and customer churn.

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“The first step in evaluating feedback is sizing up who it came from.”
Austin Kleon in “Show Your Work“

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“The art of concluding from experience and observation consists in evaluating probabilities, in estimating if they are high or numerous enough to constitute proof. This type of calculation is more complicated and more difficult than one might think. It demands a great sagacity generally above the power of common people. The success of charlatans, sorcerers, and alchemists–and all those who abuse public credulity–is founded on errors in this type of calculation.”

Benjamin Franklin and Antoine Lavoisier, Rapport des commissaires chargés par le roi de l’examen du magnétisme animal (1784), as translated in “The Chain of Reason versus the Chain of Thumbs”, Bully for Brontosaurus (1991) by Stephen Jay Gould, p. 195

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“Aragorn felt a shudder run through him at the sound, a strange cold thrill; and yet it was not fear or terror that he felt: rather it was like the sudden bite of a keen air, or the slap of a cold rain that wakes an uneasy sleeper.”
J. R. R. Tolkien in “The Two Towers“

Aragorn, accompanied by Gimli and Legolas, encounters Gandalf in Fangorn Forest but does not recognize him because he believes that Gandalf did not survive the fight with the Balrog. Tolkien’s metaphors for Aragorn’s sensation of “wake up and pay attention” are apt. It’s recognition at a subconscious level that, despite his inability to articulate it, triggers a  heightened sense of awareness. Stan Lee would have Spider-Man say, “my spider-sense is tingling” in situations like this.  I originally curated this in May 2021 but realized an entrepreneur’s intuition will often provide a very useful form of feedback.

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“I find conversations get much more real when the glint from the sharp edge of disaster is clearly visible on the road ahead.”
Sean Murphy in “Beston Jack Abrams: Recognize and Act On The Truth.”

Inspired by Abrams’ aphorism, “To the extent it requires a review of the status quo, adversity is not all bad.” I originally curated this in March 2017. If you are on the road to disaster, change course.

Eleven Sales Tips From Ian Smith

In IBM’s Rometty Gets Blunt With Workers, Ian Smith offered 23 tips, here are my top 11:

3. Recognizing when you can’t solve a problem gives you a distinct advantage.

A commitment to providing value keeps you out of trouble.

8. Authenticity comes from telling stories that you have lived through. Share details of roadblocks got round and solutions that failed. Sound human. Sound real.

I think this is easy advice for founders since they are there from the beginning. But later employees may start out telling “second-hand” success stories that have been passed down from the early years. In this case, it’s base to make it clear who shared the details.

10. Understand both the decision making process and the authorization process. The latter process may contain a key person you need to influence but may not get to meet or even talk to.

It’s entirely reasonable to ask the customer to explain their decision process and the criteria they will use to make it after a successful demonstration of the product.

11. Always prepare an ROI spreadsheet document for the prospect to play with and use.

You should play with it first to make sure you have a good chance of providing value for a reasonable range of scenarios.

14. Understand your prospects world as well as you understand your own solution.

If you work from your prospect’s operating reality and focus on delivering value it’s hard to go wrong.

16. Create realistic expectations in the prospect’s mind about how the product will be used and the timetable for success.

B2B sales success requires successful project management and the key to that is managing expectations, understanding how the customer plans to use your product, and how they will keep score.

17. Time kills deals: Deploy reverse timelines. Explain that a Dec 1^st delivery requires feet on the ground in October and a PO by the end of September type approach.

The key is to focus on when the customer will see value and then work backward from that. Too much sales advice is about securing the order when success is only assured when the customer has derived value from use in production.

18. Let the prospect define what success looks like, criteria, timing etc.

It’s legitimate to suggest possibilities that other customers have experienced but in the end the customer makes the call on acceptance criteria and implementation table subject to your ability to support it.

19. Use recap documents to summarize the exact solution, the timetable of deployment and the cost. Only once this casual document is agreed should you issue a formal proposal.

Plain English is superior to legal or contract language for achieving a meeting of the minds.

20. Build a sense of collaboration throughout the sales process not a combative, point scoring battle.

A successful software installation requires a collaborative business relationship. I think the challenge comes more from interactions with purchasing and legal staff, who take a more process-oriented approach to the deal, than from the actual users who know they will rely on you for support after the sale.

23. You are in the business of value achievement. Has your client achieved value from your product?

Unless the customer realizes value from your product you are unlikely to make a profit on the sale.

Related Blog Posts

• Effective Salespeople Commit to Providing Value
• Early Sales Efforts Foster Value Co-Creation
• Enterprise Sales Requires a Project Management Mindset
• The Value Pyramid as a Way to Structure and Define Your Offerings
• Sales KPIs for Startups
• How Founders Can Learn Sales on the Job
• Q: How Does a First Time Founder Learn Sales?
• The Robin and the Cherries: Sharing Value You Co-Create With Customers
• Newsletter: Pricing to Value
• Newsletter: Early Sales
• Do I Need To Be A Supplicant In a Sales Call?
• Successful Bootstrappers Are Trustworthy Salespeople Committed to Customer Satisfaction
• Price Based On Your Value To The Customer’s Situation

The Creative Act: A Way of Being by Rick Rubin

Rick Rubin started out as a musician and founded Def Jam Recordings, where he focused on producing albums with an eclectic mix of Rap and Rock artists. Bill Gurley recommended Rubin’s podcast, “Tetragrammaton,” and I listened to several. I learned a lot from his interview with Dr. Jay Bhattacharya and was impressed by the quality and thoroughness of his questions. I saw that he had written a book on “The Creative Act: A Way of Being.” I read it and came away inspired by several of his insights which led me to write this  post.

Each of us has a vessel

Each of us has a vessel that holds our thoughts, feelings, dreams, and experiences in the world. Unlike rain directly filling a barrel, new information enters the vessel through our unique filter set, which does not let everything through or capture what does faithfully. […] I think of a creative act as taking the sum of our vessel’s contents as potential material, selecting elements that seem useful or significant in the moment, and re-presenting them.
Rick Rubin in The Creative Act: A Way of Being

I find Rubin’s three metaphors of input filter, vessel, and creativity as selecting elements and remixing them useful. I think this model applies as much to entrepreneurs as to artists. Reading allows me to leverage other experiences, especially when I write about what I have read or try to put it into practice.

Living life as an artist is a practice; this is also true for entrepreneurs

“Living life as an artist is a practice. You can engage in the practice or not. It makes no sense to say you’re not good at it. It’s like saying, “I’m not good at being a monk.” You either live as a monk or not. We tend to think of the artist’s work as the output. The artist’s real work is a way of being in the world.”
Rick Rubin in The Creative Act: A Way of Being

I like Rubin’s perspective that an artist is engaged in a practice, a way of being in the world. In “Innovation and Entrepreneurship” Peter Drucker observes, “Entrepreneurship is neither a science nor an art. It is a practice.” In “The Great Crossover,” Dan Sullivan offers the following insight on entrepreneurial mindset:

“Successful entrepreneurs differ from other people–not in their abilities but in their mindset. They have internalized two fundamental commitments, by making these two decisions:

• Decision 1: To depend entirely on their own abilities for their financial security, because they realize that the only security is the security they create themselves.
• Decision 2: To expect opportunity only by creating value for others, because they understand that this is the only unlimited source of economic opportunity.”

Dan Sullivan in “The Great Crossover“

I agree with Dan Sullivan’s assessment that the key decision you make as an entrepreneur is to commit to quid pro quo.

Capture Thoughts of the Moment

“There’s great wisdom in transitional realms between wakefulness and sleep. Right before you fall asleep, what thoughts and ideas come to you? How do you feel when you wake from a dream? […] Keeping a dream journal might be of use. Place a pen and paper next to the bed, and as soon as you wake up, begin writing immediately with as much detail as possible before doing anything else.”
Rick Rubin in The Creative Act: A Way of Being

I adopted this practice a while ago and will capture thoughts as I start to fall asleep or when I wake up. I don’t write down dreams normally but I often wake up with ideas.

“Dreaming is neither consistently wise nor consistently useless. The dream’s power lies in the fact that is it so different a mode of thought–that it supplements and enriches what we’ve already done while awake.”
Deidre Barrett in “The Committee of Sleep“

In addition to the dream state there is hypnagogia or the act of falling asleep and the hypnopompic state of rational cognition and wakefulness after awakening. All three states can enable insight and creative solutions to problems. I keep a pad of paper by my bed to capture thoughts that occur as I am falling asleep or immediately after I have awakened.  Sometimes I will remember something I should have accomplished–or need to do tomorrow–as I am falling asleep. Writing it down allows me to relax knowing I have captured it. Other times I will wake up with an new approach to a problem or situation and write it down so that it survives my morning routine until I am ready to put it into practice.

Doubt an Idea, Don’t Doubt Yourself

“While the emotional undercurrents of self-doubt can serve the art, they can also interfere with the creative process. Beginning a work, completing a work, and sharing a work are all key moments where many of us become stuck. How do we move forward, considering the stories we tell ourselves? One of the best strategies is to lower the stakes. […]

All art is a work in progress. It’s helpful to see the piece we’re working on as an experiment. One in which we can’t predict the outcome. Whatever the result, we will receive useful information that will benefit the next experiment. […]

It’s worth noting the distinction between doubting the work and doubting yourself. An example of doubting the work would be, “I don’t know if my song is as good as it can be.” Doubting yourself might sound like, “I can’t write a good song.” These statements are worlds apart, both in accuracy and in impact on the nervous system. Doubting yourself can lead to a sense of hopelessness, of not being inherently fit to take on the task at hand. All or nothing thinking is a nonstarter. However, doubting the quality of your work might, at times, help to improve it. You can doubt your way to excellence.”

Rick Rubin in The Creative Act: A Way of Being

I think the distinction between doubting an idea and doubting yourself is a critical one. There is a world of difference between saying, “this idea is not working” and “I cannot come up with good ideas.” I think it’s legitimate to tell yourself, “I need better methods or better habits or a better approach,” which is different from “I am no good” or “I won’t be able to succeed.”

Learn From Your Scars

“In Japanese pottery, there’s an artful form of repair called kintsugi. When a piece of ceramic pottery breaks, rather than trying to restore it to its original condition, the artisan accentuates the fault by using gold to fill the crack. This beautifully draws attention to where the work was broken, creating a golden vein. Instead of the flaw diminishing the work, it becomes a focal point, an area of both physical and aesthetic strength. The scar also tells the story of the piece, chronicling its past experience.”
Rick Rubin in The Creative Act: A Way of Being

Learning from setbacks is part of an anti-fragile approach. There is a Latin proverb, “haec quae nocent docent.” It means those things which hurt teach. Human scar tissue is not as strong or flexible as regular skin and does not contain hair follicles or sweat glands, but it grows more quickly and minimizes the time you have an open wound. I think the challenge for entrepreneurs is to take immediate action to minimize damage and then continue learning and improving their methods.

Uncover Your Assumptions and Test Them

“It’s helpful to remember that when you throw away an old playbook, you still get to keep the skills you learned along the way. These hard-earned abilities transcend rules. They’re yours to keep. Imagine what can arise when you overlay an entirely new set of materials and instructions over your accumulated expertise. As you move away from familiar rules, you may bump up against more hidden rules that have been guiding you all along, without your knowledge. Once recognized, these rules may be released or used with more intention. Any rule is worth testing, be it conscious or unconscious. Challenge your assumptions and methods. You might find a better way. And even if it’s not better, you’ll learn from the experience. All of these experiments are like free throws. You have nothing to lose.”
Rick Rubin in The Creative Act: A Way of Being

The key is to document your playbook so you can continue to improve it. You may throw a play away but I don’t see throwing away the entire playbook.

“If several directions seem captivating, consider crafting more than one experiment at a time. Working on several often brings about a healthy sense of detachment.”
Rick Rubin in The Creative Act: A Way of Being

Sometimes one approach seems the most promising, but it never hurts to outline several potential approaches. Exploring two or three alternatives in parallel can give you more resilience. At a minimum, preparing a Plan B and a Plan C in advance means you are less likely to get locked into an approach that’s not working.

Be Patient With Yourself But Get Started

“Crafting contains a paradox. To create our best work, we are patient and avoid rushing the process, while at the same time we work quickly without delay.”
Rick Rubin in The Creative Act: A Way of Being

I think you have to be patient with yourself but work when you see a path  forward. Picasso is credited with the quote, “inspiration exists, but it must find you working.” This is the secret to the Pomodoro technique and other time-boxing methods: you force yourself to get started, and that can unlock the inspiration to continue.

“If you’re holding a center puzzle piece in your hand and staring at an empty tabletop, it’s difficult to determine where to place it. If all of the puzzle is complete except for that one piece, then you know exactly where it goes. The same is generally true of art. The more of the work you can see, the easier it becomes to gracefully place the final details clearly where they belong.”
Rick Rubin in The Creative Act: A Way of Being

I think we imagine the key elements of a design and capture them in rough outlines, sketches, and draft form before we start implementing in detail. In solving a problem or completing a puzzle it’s more common to work form the outside in, from the constraints or the edge pieces, but with a design I think you normally start with the core ideas. It’s useful to be able to work  both top-down, from the general to the specific, as well as bottom up, collecting “dots” or details to see what patterns you can discern.

SKMurphy Take

I got a lot out of this book and have filled this post with quite a few long quotes from it as a results. Although Rubin’s audience is artists, I found a lot of what he wrote applied equally well to the challenges that entrepreneurs face.

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Chip Cassin Software Rules

Chip Cassin posted a comment in the Software Development subreddit that are re-published here with his permission. They are outstanding:

Make it good, then make it better. The perfect is the enemy of the good.

Don’t wait, get started with something good enough. Use a Probe-Sense-Respond approach where you share functional prototypes and than act on the feedback they generate.

Avoid long release cycles. Many projects are like hacking through tall weeds. No one can see 6 to 9 months down the road. Aim for shorter release cycles.

Taking short steps, starting with low-fidelity prototypes and customer interviews, means you can gather evidence as you go instead of having to predict too far ahead.

Most users just want to do just 3 or 4 things in your tech. Put those things in front and easy to find and use. All the other crap features that you think are cool you can still have in there but put them behind menus. Only your most tech users will use them.

You get three strikes. My rule of thumb has been you only get to name three features or capabilities to move the needle in a conversation with a prospect. You can ask diagnostic questions to tune your approach but if the first three don’t do it, more won’t help.

Live by the 20/60/20 rule.

• 20% of your users are quick enough to figure everything out.
• 20% never will.
• Your job is to help the remaining 60%.

Where entrepreneurs get fooled is that the “20% of your users are quick enough to figure everything out” are first-movers who mask what will be required to get the persuadable 60%.

Perception is Reality. Once your users en masse believe something about your tech is true, it is really difficult to turn that around. Stay ahead of perceptions.

I think you have to pay attention how satisfied customers describe your product and echo  that language to prospects. Don’t fixate on your earlier positioning and attempt to change how satisfied customers tell others about your product.

As much as possible, help your users first and your stakeholders second. Your users will notice, and support you and give you lots of yardage down the line, and is how reputations are built.

I think this is more about making sure that the users are satisfied as a path to keeping the economic buyer happy.

It is OK if an app has bugs. It is how you respond that matters. How many of us stick with a product because the company supports it really well?

A few bugs that are fixed fast are acceptable. You cannot ship buggy crap  and hope to fix it fast enough to avoid getting thrown out.

About Chip Cassin

Highlights from https://www.linkedin.com/in/chipcassin/

CRM Implementations Sales, Marketing, Contact Centers/ Salesforce Expertise / Engineer / Project Manager / Business Analyst. Adobe, Intuit, HP, Symantec, Johnson & Johnson, American Express, Apple, etc.

Full Disclosure: Hands On Techo-Functional CRM. I would never call myself a developer, though that is where a lot of my professional success has been. Rather, I’ve always been more of a Jack of all Trades Project guy, meaning lots of years on projects in CRM. I have been Project Manager more times than I have fingers on my two hands, have done a lot of the BA stuff, ie architecting, data modeling, building requirements, training, but I also on occasion write code and perform configuration work if it needs to be written and/or figured out or if the developers are just too busy with other things. In addition, even though I have a lot of project experience, I am no longer SF certified.

Hands on Functional. Proficient in Apex, JavaScript buttons, Somewhat proficient in Visual Force
CRM expertise with multiple CRM packages and cross functional business groups.

12+ Years CRM Project Management, Business Process Change Management, CRM/Finance/HR
Multi-Phased Implementations (New & Upgrades)
Focus on Usability/Maintainability
Technology Re-Architecting and Design
Business Process Change Management

Specialties: All sorts of CRM, Salesforce, Siebel, Oracle Fusion, Peoplesoft, SAP, Apex, Project Management, Business Process Realignment, HR, Sales Force Automation, CRM, Partner Portals, Marketing, Call Centers, Project Manager, Business Analyst, Siebel, VB, VBA, Visual Basic, Salesforce.com, Cold Fusion, Vitria, Middleware, Connectors, Interfaces, SAP, Project Implementations, SDLC, Oracle Fusion

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