Quotes for Entrepreneurs Curated in November 2022

Quotes for entrepreneurs curated in November 2022 around of theme of prudent risk-taking, the art of sound judgment in uncertain situations.

Quotes for Entrepreneurs Curated in November 2022

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: prudent risk-taking, the art of sound judgment in uncertain situations.

Prudent risk-taking entails mastering the calculation of affordable losses. Commit resources (time, money, social capital) to learn more about the market or to improve your business operations–but only when you can recover from their complete loss.
Sean Murphy in “Purpose, Patience, Politeness, and Prudent Risk-Taking”

My current best effort at a definition for prudent risk taking.

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Rules for Entrepreneurs on prudent risk taking

“I have two basic rules about winning in trading as well as in life:
(1) If you don’t bet, you can’t win.
(2) If you lose all your chips, you can’t bet.”
Larry Hite

From an interview with Jack D. Schwager in Market Wizards: Interview with Top Traders (1989). Survival is a necessary precondition for being able to apply what you learned from an experience. You can also learn from others who don’t survive. I originally curated this in Sep-2022 and am re-running because it’s central to the theme for this month: prudent risk-taking.

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“There are really four kinds of trades or bets: good bets, bad bets, winning bets, and losing bets. Most people think that a losing trade was a bad bet. That is absolutely wrong. You can lose money even on a good bet. If the odds on a bet are 50/50 and the payoff is $2 versus a $1 risk, that is a good bet even if you lose. The important point is that if you do enough of those trades or bets, eventually you have to come out ahead.”

Larry Hite in an interview with Jack D. Schwager in Market Wizards: Interview with Top Traders (1989)

I learned this as “good decision, bad outcome.” It was a good decision based on the information you had at the time, but you still had a bad outcome. This framing guards against judging a decision purely by it’s outcome which can blind to you good opportunities.

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“I am superstitious to this extent–I believe that giving up before you begin is bad luck.”
Robert Brault

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Being “good with computers” means having the confidence/persistence to solve or work around computer-related problems. Zig Zigler said “Increase your confidence, increase your competence.” It’s true.
John D. Cook (@JohnDCook)

I think confidence to tackle hard problems is a hallmark of expertise but you may be inverting the causality. I think as your competence increases your confidence does as well. My take is the the overconfident tackle the whole problem at once, experts divide and conquer.

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Q: How long is a piece of string?
A: It depends.

A more polite, and more directly useful, response is “What is the problem you are trying to solve?”

From “How Long is a Piece of String?

When I started out at Cisco in 1990 it was a part of the culture that a request for help or question that was too vague or poorly specified would be answered with “How long is a piece of string?” Part of prudent risk taking is clearly framing the problem and the risks you are willing to absorb.

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“Just call me the little engine that said “ok, but I need some coffee first.”
Bruno Pieroni (@brunopieroni) May-29-2014 tweet

h/t Barry Popik. A good example of a bounded commitment, specifying what is necessary to complete a project.

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watashiato n. curiosity about the impact you’ve had on the lives of the people you know, wondering which of your harmless actions or long-forgotten words might have altered the plot of their stories in ways you’ll never get to see.

John Koenig in “Watashiato” in the Dictionary of Obscure Sorrows

I don’t do enough to express gratitude for the small kindnesses, the offhand insights,and the casual favors that opened doors and changed my perspective on what was possible for me. I need to recommit to expressing appropriate gratitude. My thought for Thanksgiving.

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“You’re advocating 1970s technology!”

“Yes, but that’s as far as people used to 1920s technology can go in one step.”

If you try to bring a flat piano up to pitch too quickly you can break strings.

Will Durant: “Woe to him who teaches men faster than they can learn.”

John D. Cook (JohnDCook)

It’s the “Zone of Proximal Development” or maximum amount of new information / learning that can be absorbed in a period of time. Marcelo Rinesi speculated that there is an “Expertise Acquisition Light Speed Barrier” in 2009. Related quote:

“There is a certain intrinsic rate at which a team can absorb new ideas while still turning out productive work. New ideas and new tools are usually disruptive. I don’t care how good the idea or tool is, there’s an inherent cost in taking it onboard. The cost of one or two at a time is manageable. The cost of several new things all at once can be ruinous. There’s a invisible line called “the maximum safe rate of change”, and you don’t want to cross it.”
Eric Lee (@SaintGimp) in “Do Not Exceed the Maximum Safe Rate of Change” (2009)

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“The public health apparatus’s reluctance, throughout this miserable event, to meet the public where it lives has become a cliché. They won’t budge, and the country is moving on without them. But moving on is impossible in the absence of a thorough reckoning. It’s incumbent on this generation to establish for posterity what went wrong over the last two and a half years, if only so that we will never do this again.”

Noah Rothman in “The Covid Reckoning is Coming” (Aug-12-2022)

One test that you have built an effective learning organization is a willingness to engage in after action reviews (also known as retrospectives or postmortems).  It would be fantastic progress if public health professionals would lead on this.

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“Nothing reduces opportunities for serendipity quite like pushes to increase efficiency.”
Lorin Hochstein (@norootcause)

Some other trade-offs (there is no good or bad side)

  • Security <–> Convenience
  • Resilience <–> Efficiency
  • Efficiency <–> Serendipity
  • Explore / Discover <–> Exploit / Deliver / Execute
  • “If Only” / Regret <–> “Next Time” / Anticipate
  • Promise You Rely Can Rely on <–> Experiment to Learn

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“The creative individual achieves his heightened awareness of some aspects of life by ignoring other aspects. And since the aspects he ignores are often precisely those routine matters on which the rest of us lavish loving attention, he is often put down as odd. […]

The creative individual has the capacity to free himself from the web of social pressures in which the rest of us are caught. […]

He is capable of questioning the assumptions that the rest of us accept. […]

He is particularly gifted in seeing the gap between what is and what could be (which means, of course, that he has achieved a certain measure of detachment from what is).”

John W. Gardner “Self-Renewal

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“When you close your laptop and suddenly realize you’re in the dark.”
“Very British Problems” (@SoVeryBritish)

This happens more often than I care to admit. It reminds me of an experience Greg Knauss recounted:

“Once, years ago, I had a morning deadline, a lot of code to write and a two-liter bottle of Mountain Dew. Around 4am, I realized that the window was still open and I was freezing, I hadn’t gone to the bathroom is something like fifteen hours and I was having trouble hitting the keys because my hands were trembling.

Man, do I miss those days.”

Greg Knauss in “Man, Do I Miss Those Days.

I have used  Knauss’ quote in three blog posts but this is the first time I have curated it in a “quotes for entrepreneurs” roundup.

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 “Creativity is the ability to identify self-imposed constraints, remove them, and explore the consequences of their removal”
Russell Ackoff’

I really like this definition and referenced it a times already:

And again this month:

I said–perhaps a little too automatically, “But a test board will be a significant extra expense!”

At this, several people in the group pointed out that our current fire drill had been very expensive in both additional spins and time to market. And I realized I had been an idiot (or that my team had helped me reach a creative solution in the Russell Ackoff’s definition: “Creativity is the ability to identify self-imposed constraints, remove them, and explore the consequences of their removal”).

Sean Murphy in “Managing Recurring Problems In Your Startup”

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  • Charles Lambdin (@CGLambdin): What are your fav methods for challenging assumptions?
  • Sean Murphy (@SKMurphy): I like the question “what would have to be true” to look at the implications of an assumption or hypothesis.

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Plan The Night Before
You never want to wake up with uncertainty.
Avoid it by planning your day the night before.
Make a to-do list of bite-sized tasks that will get you closer to your big goal.
Then when you wake up, you know exactly what you need to do.
Tim Stoddart (@TimStodz)

Most time management books recommend this approach but Tim’s observation about “avoid waking up with uncertainty” makes this more memorable.

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Tired: How can we do better next time?
Wired: What made it hard this time?
Lorin Hochstein (@norootcause)

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“Real year for the mainstream orthodoxy crowd. Big wins for the guy that thought

  • overdoing stimulus is dangerous,
  • that crypto is mostly just scams,
  • that authoritarianism is bad and inefficient.

Mike Bird (@Birdyword)

Related quote on crypto:

“It’s like somebody else is trading turds and you decide, I can’t be left out.”
Charles Munger in an interview at the  annual meeting of Berkshire Hathaway in May 2018

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“There is no friction here.
It’s a kind and buoyant place.
What you forget, living here, is that just because you have stopped sinking doesn’t mean you’re not still underwater.”

Amy Hempel in “Tonight is a Favor to Holly” in “Collected stories of Amy Hempel” [archive.org]

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“I’m a pessimist about probabilities, I’m an optimist about possibilities. Life contains both things and if you’re not able to face the fact that there are tragic and irreparable elements in life, you’re unable to understand the course of human development. ”
Lewis Mumford in “Lewis Mumford Remembers”  (1977)

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Quotes for Entrepreneurs: Five Question Kata

  1. What is the Target Condition?
  2. What is the Actual Condition now?
  3. Reflect on Last Step Taken
    1. What did you plan as your Last Step?
    2. What did you Expect?
    3. What Actually Happened?
    4. What did you Learn?
  4. What Obstacles do you think are preventing you from reaching the target condition. Which “one” are you addressing now?
  5. What is your Next Step? (Next experiment) What do you expect?
  6. How quickly can we go and see what we Have Learned from taking the next step?

Mike Rother (@RealMikeRother)

It’s a well thought out experimentation model. In my experience obstacles may be constraints or forces at work, often in organizations they can be incentives or fears (in particular, fear of loss of expertise or status after a change). I also think it’s good to proceed step by step but you can never do “one” thing at a time, no matter how careful. You always need to alert to multiple effects from what you may feel is a simple action.

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“I’d put Facebook somewhere around where Blackberry was in 2011–still relevant, still powerful, still incredibly rich, but absent some significant strategic shift, likely to evolve to be a shadow of its former self.”
Rita McGrath in “Lying–or not telling the whole truth–comes to haunt Meta

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“Are teams in your organization forced to handcraft extensions and substitutions to your “official platform” to overcome deficiencies and shortcomings that prevent them from getting work done productively? Perhaps you should focus less on control and more on enabling effective workflows.”
Sean Murphy

My message to IT in response to

Shadow Platform… the cousin of Shadow IT. Are teams in your org increasing the combinatorial complexity of your architecture in operation by handcrafting Shadow Platforms to avoid using your “official” platform?
Jabe Bloom

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“Often you do the right thing but the wrong thing still happens.”
William Stafford in “Sound of the Ax: Aphorisms and Poems of William Stafford

“Right thing” is predicated on your current understanding of a situation or related system. Sometimes it’s more complicated than you realize. Actions can have more than one effect so it’s hard to predict the final effect from “doing the right thing.”

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“Life doesn’t take breaks to allow us to catch our breath. Fate won’t hold back while we adjust our footing. Life just hits. And when it does, sometimes all you can do is to take it. But that does not mean you have to allow it to take you down. Circumstances that you thought would be the end of you can end up making you.

When nothing seems to be going your way, keep going.”

Kyle Creek in “Speech Therapy: 52 Pick-Me-Ups

I remember watching interviews with American veterans who survived the Normandy landings on D-Day. Several said the same thing in different ways: “it was a very difficult situation but I just put one foot in front of the other and kept moving forward.”  2023 may be a year that will test your ability to persevere even more strongly than the last two years.

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“A capacity for calm deliberation–the beginning of all wisdom, the source of all excellence.”

Marie von Ebner-Eschenbach in “Aphorisms”

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If you had just a minute to breathe
And they granted you one final wish
Would you ask for something like another chance
Jim Capaldi in “The Low Spark of High Heel Boys

The trick is to see that road you are on is not going to work before you head the dead end. If you never go “all in” on a particular strategy or course of action–keeping a reserve that will allow you to try Plan B and Plan C (or double down on Plan A if it works).  In “Andrew Grove on Recognizing Reality” I share a turning point at Intel from Grove’s “Only the Paranoid Survive

“If we got kicked out and the board brought in a new CEO, what do you think he would do?” Gordon answered without hesitation, “He would get us out of memories.” I stared at him, numb, then said, “Why shouldn’t you and I walk out the door, come back and do it ourselves?”

Andrew Grove in “Only the Paranoid Survive

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“Impostor syndrome is just a sign that you’ve found a bunch of stuff you’d like to learn.”
Steve Purcell (@sanityinc)

So is a

    • sense of wonder
    • a feeling of energy and opportunity
    • sense of surprise
    • a small accomplishment that tells you mastery is possible
    • a clear view of an objective that requires you to cross a valley

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“It is the possibilities which are the most terrible things in life.”
Phyllis Bottome

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“Instead of striving to be right at high cost, it will be more appropriate to be flexible and plural at a lower cost. If you cannot accurately predict the future then you must flexibly be prepared to deal with various possible futures.”
Edward De Bono in “Serious Creativity

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“The ability to learn faster than competitors may be the only sustainable competitive advantage. [..] The best learning takes place in teams that accept that the whole is larger than the sum of the parts, that there is a good that transcends the individual Arie P. de Geus in “Planning as Learning” in HBR March-April 1988

I used these two thoughts as a point of departure for  “Startups Where ‘We Are All In this Together’ Learn Faster

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“Building a company is not a short-term endeavor. For many, breakthroughs don’t come immediately, but rather occur later in the company timeline. Survival is often the primary strategy. This allows time to build the business model, find a product that resonates with the market, and develop an operation that can scale. Competition will exist. But the race is about who will survive the longest, not about who goes to market first.”

Alex Lazarow in “Startups Should Think Like Camels–Not Unicorns” (Oct-16-2020)

I like the camel metaphor for enduring companies instead of the “cockroach” model popularized by Caterina Fake. this write-up defines rules of thumb new businesses outside of Silicon Valley follow as a matter of course:

  • Value based pricing
  • Prudent growth built on paying customers
  • Cost management with expenditures following revenue (“bootstrapping”).

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“People speak of Hope as this delicate, ephemeral thing made of whispers and spider webs. She is not. Hope has dirt on her face, blood on her knuckles, the grit of the cobblestones in her hair, and she just spat out a tooth as she rises for another go.”

Matthew (@CrowsFault) Mar-10-2022 tweet

I like this perspective on hope as an aspect of a muscular faith. It reminds me of James 1:17: “Every good endowment and every perfect gift is from above, coming down from the Father of lights with whom there is no variation or shadow due to change.”

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“Programmers waste time improving the speed of noncritical parts of their programs to the detriment of debugging and maintenance. Don’t guess or rely on intuition: use measurement tools to determine the critical 3% of your program where speed improvements matter.”

Donald E. Knuth

Condensed from

“There is no doubt that the grail of efficiency leads to abuse. Programmers waste enormous amounts of time thinking about, or worrying about, the speed of noncritical parts of their programs, and these attempts at efficiency actually have a strong negative impact when debugging and maintenance are considered. We should forget about small efficiencies, say about 97% of the time: premature optimization is the root of all evil. Yet we should not pass up our opportunities in that critical 3%. A good programmer will not be lulled into complacency by such reasoning, he will be wise to look carefully at the critical code; but only after that code has been identified. It is often a mistake to make a priori judgments about what parts of a program are really critical, since the universal experience of programmers who have been using measurement tools has been that their intuitive guesses fail.”
Donald E. Knuth in  Structured Programming with go to Statements, Computing Surveys, Vol 6, No 4, December 1974

h/t Quote.Org “There is no doubt that the grail

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“We expect that most of our ideas won’t work, and those that do will require multiple iterations.”

Marty Cagan (@cagan)

h/t Holly Hester-Reilly (@H2RProductSci) This reminded of two insights from Gerald Weinberg’s “Secrets of Consulting”

New Law: Nothing new ever works.

The Rule of Three: If you can’t think of three things that might go wrong with your plans, then there’s something wrong with your thinking.

Gerald Weinberg in “Secrets of Consulting”

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