Quotes for entrepreneurs curated in May of 2021, theme this month is confronting fears and anxieties.

Quotes for Entrepreneurs Curated in May 2021

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. Please enter your E-mail address if you would like to have new blog posts sent to you.


Theme for this month is confronting fears and anxieties.

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“Anyone who claims to 100% know how the future will turn out is lying (or deluded). everybody has a portfolio of epistemic bets with varying justifications. A reputation for accuracy comes from playing the risk landscape well enough to get lucky where it counts. preparation meeting opportunity ‘n’ all that. In fact it would be silly to optimize for maximum number of bets paying off versus being the most right where it matters the most.”
Sonya Mann in (@asonyasupposedly)

I think strategy organizes your efforts to be right where it matters most. Tactics are about increasing the chances for each bet (and therefore most number of bets) paying off.

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“When looking for your team, the co-founder rule of thumb is ‘shared values, complementary strengths.’ Many of the serious arguments between co-founders can stem from overlapping strengths.”
Sean Murphy in “Working Capital: It takes more than money

Cited by Phil Liao as a “nugget of wisdom” in his review — Phil Liao Reviews “Working Capital: It Takes More Than Money”

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“Healthy fear is specific and constructive. It sparks physical energy and mental clarity. It enables you to summon your deepest capacities to protect something that you value that is threatened. Fear is specific and constructive

Anxiety is diffuse. Where fear galvanizes you into action, anxiety debilitates you and paralyzes you so that you are unable to make a decision or act.

Fear is a thunderstorm that passes back into sunlight and green grass. Anxiety is a cold drizzle, it’s 34 degrees and raining all the time so that your soul starts to mildew.

Anxiety is a threat to your sense of self, when your identity and sense of security are eaten away. It’s deeper and more destructive.

Tim Keller in “Praying Our Fears” [link starts at 9:46 min mark with definition from Rollo May, Keller’s story begins at 11:06]

If fear is a thunderstorm then relief or grief; either I prevent the loss or end up mourning it. But anxiety requires me to renew my gumption or face disintegration or degradation into a dried husk. Here is a story Keller tells to illustrate healthy fear.

“When my middle son, Michael, was four years old, I had put him–like a really smart young father–at the top of this 8-foot tall slide and then walked a dozen feet to the other end of the slide. Michael, being a typical four-year-old, stood up and promptly pitched backward. And as he was heading down into the concrete, I caught him. Kathy and I still look back and say, ‘How did you do that?’ Kathy sometimes says, ‘Do that again.’ And I’ll never be able to do it again. Here’s what researchers will tell you happened. My autonomic nervous system was activated by my fear. I had this enormous burst of physical energy and mental clarity. It’s almost like time slowed down, I felt like I had five minutes to get there. There is such a thing as healthy fear.”
Tim Keller in “Praying Our Fears” [link starts at 9:46 min mark with definition from Rollo May, Keller’s story begins at 11:06]

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Liz and Mollie: Take What You Need (Quotes for Entrepreneurs)

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“The estimated value of perfect information places an upper limit on the value of any information gathering activity.”
Charles Lambdin (@CGLambdin)

This works for situations where the risk and range of unknowns can be calculated with some confidence. The challenge entrepreneurs that constantly need to manage is when to take action in the absence of certainty. Information gathering is always a good idea but safe actions can act as probes to help learn more. Delaying action–in effect inaction–can have as much downside as a the wrong action. The “expected value of perfect information” (EVPI) is a term of art used in Decision Analysis. “Perfect Information”means knowledge of the structure of the situation and the probabilities associated with each possible outcome. It does not include knowledge of competitor plans and intentions. Chess is a game of perfect information the complete state of the board and disposition of all pieces is known at all times.

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“Every storm runs out of rain”
Maya Angelou

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“Chess has only two outcomes: draw and checkmate. The objective of the game is absolute advantage–that is to say, its outcome is total victory or defeat–and the battle is conducted head-on, in the center of the board. The aim of Go is relative advantage; the game is played all over the board, and the objective is to increase one’s options and reduce those of the adversary. The goal is less victory than persistent strategic progress.”
Dr. Henry Kissinger in “America’s Assignment: What will we face in the next four years?” (Newsweek November 8, 2004)

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“We must travel in the direction of our fear.”
John Berryman

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“Courage consists not of the absence of fear and anxiety but the capacity to move ahead even though one is afraid.”
Rollo May in “The Meaning of Anxiety”

Which reminds of this quote from Mark Twain:

“Courage is resistance to fear, mastery of fear—not absence of fear.”
Mark Twain Pudd’nhead Wilson, opening quote for Chapter 12 (1894).

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“All revolutionary changes are unthinkable until they happen–and then they are understood to be inevitable.”
Theodore Roszak

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“Failing early” is a symptom of one-plan-at-a-time thinking. The aim should be to dissolve failure, using a more cumulative, as opposed to the traditional sequential, approach.
Charles Lambdin (@CGLambdin)

This is really good. In an operational plan you would have branches to anticipate contingencies where early operational goals are not achieved. I see clear mapping between operational art and an entrepreneurial mindset (e.g. for new product introduction or evolution).

  • Sequel: what’s next when execution and results are on plan.
  • Branch: contingency options built into the base plan for changing the mission, orientation, or direction of effort based on anticipated events, opportunities, or disruptions caused by competitor actions and reactions.

Operational art integrates ends, ways, means, and risks across the strategies, campaigns, major operations, tactics employed for success.
I have adapted this definition in part from Patrick Sweeny’s “Operational Art Primer” from military to startup / product applications.

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“The secret of science is to ask the right question, and it is the choice of problem more than anything else that marks the man of genius in the scientific world.”
Sir Henry Tizard

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“You haven’t mastered a tool until you understand when it should not be used.”
Kelsey Hightower (@kelseyhightower)

The ability to use the right tool for the problem at hand separates the lucky from the wise.

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“Failure is an event, not a person. Yesterday ended last night.
Some of us learn from other people’s mistakes, the rest of us have to be the other people.
Worry is interest paid before it’s due. ”
Zig Ziglar

“Yesterday ended last night” reminds me of the title of a great book by Michael Malone called “The Future Arrived Yesterday” that I blogged about in The Future, Arriving Yesterday, Remains In Constant Motion. I recycled that phrase as a section heading in “Moon over Soho: Nature, Technology, Magic” and closed section with this observation:

“The impact of a new technology is hard to spot when your mental models are shepherding you along familiar paths that are obsolete.”
Sean Murphy in “Moon over Soho: Nature, Technology, Magic

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“Spend a lot of time listening to your customer’s problems. Not every problem is one you can or should solve, but the aggregation of their issues gives you a solid base for making seat-of-the-pants decisions. You’ll never have enough information to make a MBA-style decision on new products or directions. But if you’ve listened to enough customers you’ll have a good “feel” and make better decisions.”

Steve DiBartolomeo in “Founder Story: Steve DiBartolomeo of Artwork Conversion Software

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“When people are all in, normal benchmarks cease to apply.”
Peter D. Kaufman

h/t Brian Norgard (@BrianNorgard). Commitment can tip the scales, but it “all in” can also lead to a loss of perspective. Peter D. Kaufman is the CEO of Glenair and the editor of “Poor Charlie’s Almanack: The Wit and Wisdom of Charles T. Munger.” Kaufman gave a recent talk on multidisciplinary thinking that included some very interesting insights:

“The three hallmarks of a great investment are:

  1. superior returns
  2. low risk
  3. long duration.

The whole world concentrates on Category 1. But if you’re a leader of any merit at all, you should be treating these three as what? Co-priorities. How do you get low risk and long duration? Win-Win. This is the biggest blind spot in business. This is the biggest blind spot in business. People are actually proud of a win-lose relationship. ‘Yeah we really beat the crap out of our suppliers.’ You know, ‘We’ve got these employees for…you know, we’ve got them on an HB1 visa, they can’t work anywhere else for three years.’ They’re proud of it! Total Win-Lose.”

Peter D. Kaufman in “The Multidisciplinary Approach to Thinking” (2018)

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“A love of tradition has never weakened a nation, indeed it has strengthened nations in their hour of peril; but the new view must come, the world must roll forward. ‘Let the great world spin for ever down the ringing grooves of change.’ as Tennyson said many years ago. Let us have no fear of the future.”

Winston Churchill in a Speech in the House of Commons, November 29, 1944 “Debate on the Address”

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A founder will make a thousand business decisions in a year. About half a dozen will matter 100x more than the others. Are you spotting those issues?

The reason to have advisers and board members is not to tell you what to do but rather to help you spot the most important “power law” issues.

When you’re in the weeds, as operational founders need to be, it’s easy to miss that a single decision might be more important than anything else you do that year.
David Sacks @DavidSacks

Here are three questions on my checklist of  how to evaluate a business challenge or opportunity:

  1. What are we missing?
  2. Knowing what we know now what should we stop doing?
  3. Where did we get lucky?

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“To be an inventor, you have to be willing to live with a sense of uncertainty, to work in this darkness and grope towards an answer, to put up with anxiety about whether there is an answer.”
Ray Dolby

Insight can be a flash of lightning on a dark rainy night or a growing sense of warmth and purpose as you iterate toward a solution. I think “smaller” insights and solutions are preceded by a feeling of warmth or getting close to a solution, where significant insight occur during daydreams or when your thoughts are drifting.

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“The right culture, the highest and best culture, is a seamless web of deserved trust.”
Charles Munger

h/t Tren Griffin “A Dozen Things I’ve Learned from Charlie Munger” via Brian Lui in “Upside Decay.” I added this as a closing quote to “Clayton Christensen: How Will You Measure Your Life?” along with a summary of Upside Decay because Lui’s scales up Christensen’s prescription for individuals to organizations and nations.

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“Farebrother turned his head to the the bombers plodding on toward their target, searching the horizon for the escorting Fighter Groups which hadn’t arrived. Who could see the bomber crews without admiring the phlegmatic determination which makes other kinds of courage seem no more than temporary lapses of judgment? They were the real heroes, the ones who came up here day after day as human targets for every weapon an ingenious, dedicated, and tenacious foe could use against them. So in life itself the true measure of courage is to fly on despite the tragedies of accident, sickness, or failure.”
Len Deighton in “Goodbye, Mickey Mouse” [Archive.org]

I have been reading a mix of Deighton’s fiction and non-fiction books related to World War 2. I found “Goodbye, Mickey Mouse” about WW2 American fighter escorts based in Britain very moving. Two good sites devoted to Len Deighton’s work are:

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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.

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“Don’t just do something. Sit there.
Don’t consider everything, just everything that matters.”
Bruce Pandolfini

Two from Pandolfini that neatly summarize two distinct hallmarks of expertise. Experts think hard when they are in trouble and they see the essential facts amidst the “blooming buzzing confusion of the world” in all of it’s rich detail. Two related quotes:

“Among a great many other things that chess teaches you is to control the initial excitement you feel when you see something that looks good. It trains you to think before grabbing, and to think just as objectively when you’re in trouble.”
Stanley Kubrick quoted in Kubrick by Michael Ciment

I used this in “Chess Quotes for Entrepreneurs” a longer version of the quote appears in the post.

“The baby, assailed by eyes, ears, nose, skin, and entrails at once, feels it all as one great blooming, buzzing confusion.”
William James in “Principles of Psychology, Volume 1” [Gutenberg]

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“Nothing is sadder than a happy memory, when everything is changed, and all the people are dead.”
Ashleigh Brilliant (born Dec-9-1933)

Like people, all happy memories will dwindle to one survivor’s memory and then just in stories handed down. We should treasure them all the more. This reminded me in a strange way of Achaan Chaa’s answer to Mark Epstein’s question “what do you mean by ‘eradicating craving’?”

“You see this goblet?

For me, this glass is already broken.

I enjoy it; I drink out of it. It holds my water admirably, sometimes even reflecting the sun in beautiful patterns. If I should tap it, it has a lovely ring to it.

But when I put this glass on a shelf and the wind knocks it over or my elbow brushes it off the table and it falls to the ground and shatters, I say, ‘Of course.’

But when I understand that the glass is already broken, every moment with it is precious.”

Mark Epstein’s Thoughts Without a Thinker (pages 80-81)

I used the Epstein quote in Thanksgiving 2011.

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“In real life, when you fill in pieces of a puzzle, the existing pieces also transform. Perhaps it’s more like color mixing than a jigsaw.”
Charles Lambdin (@CGLambdin)

Niels Pflaeging suggested in a recent article that change in these systems is like pouring milk into coffee, once it’s done it changes the coffee forever, you cannot take it back and the pattern in unpredictable. This highlights the need for feedback driven change as a more appropriate approach to work with the complexity, rather than plan-driven change that assumes predictable cause and effect:

“Spill a tiny bit of milk into coffee, and with this tiny nudge a new pattern is instantly being created. It’s altogether different from the original one, pure coffee, and the change is permanent. there’s no way of returning to the first pattern. This is much more similar to what change actually is than calling change a journey.

Change is like adding milk to coffee. This is a more helpful metaphor than the wide-spread notion of seeing change as a ‘journey from here to there.'”

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With the introduction of any new feature 5 questions must be answered:

  1. What problem does it solve?
  2. What downstream problems does it create?
  3. Who is this for?
  4. How can it be measured?
  5. How can it be simplified?

If you can’t clearly answer all of these questions don’t bother.
Brian Norgard (@BrianNorgard)

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“Ignorance more frequently begets confidence than does knowledge: it is those who know little, not those who know much, who so positively assert that this or that problem will never be solved by science.”

Charles Darwin in “The Descent of Man”(1871)

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“First there is a mountain,
then there is no mountain,
then there is.”
DonovanThere is a mountain

An entrepreneur sees a mountain of effort in the distance.
Then there is just the effort of climbing, no mountain, just next few steps.
Finally the vantage from the summit of a mountain of effort.

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“People say I ask a lot of questions.
I’m not afraid of looking dumb; I’m afraid of being dumb.”
Andrew Cronk (@ajcronk)

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“He had been saving it up too long. So had she, from the looks of things. Coolidge sat there, straining upward while Vera oscillated, nice smile on her face that kept breaking up, at first intermittently, then more often, until there was no more smile at all. None. She looked as though she were trying to remember something deep down. Something crucial. And Coolidge was jogging her memory. Then her face had a look of discovery and it all came back to her in a flash.”
Stan Lee in Dunn’s Conundrum

This is not the Stan Lee of Marvel Comics fame but the copywriter behind the “Daisy” ad than ran once in the 1964 Johnson-Goldwater presidential contest. The CONELRAD website has an extensive write up on Daisy. Lee also wrote “The God Project.” Both books are recommended as thought provoking Cold War thrillers that combine considerable humor with insights into the dynamics of how wars get started.

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“A nation or civilization that continues to produce soft-minded men purchases its own spiritual death on an installment plan.”
Martin Luther King, Jr.

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“Man lives in a world of surmise, of mystery, of uncertainties.”
John Dewey