Irina Calciu: Lessons from
Building AI Systems, Products, Startups

Irina Calciu, founding systems architect at Pervasive AI and former co-founder of Graft, shared lessons from building AI systems, products, and startups. Drawing on her background in distributed systems, VMware Research, and enterprise AI, she emphasized the challenge of turning AI into reliable production systems.

A major theme was the difference between building impressive technology and building a successful business. Startups must continually balance moving quickly with thinking deeply. Better technology does not automatically win; once customers adopt a solution, switching costs can make a technically superior alternative difficult to sell. Customer adoption can also fail for reasons unrelated to product quality, including budgets, staffing, timing, and organizational readiness. This makes working with multiple design partners essential rather than depending heavily on one or two early customers.

Irina strongly advocates dogfooding, using your own product every day. Founders should also stay closely involved with early customers, respond rapidly to problems, and learn from real attempts to deploy the product. However, customer requests need boundaries. If one customer pulls development toward highly specialized features that others will not buy, a software startup risks becoming a custom consulting business.

Product-market fit comes from talking to real customers, testing real deployments, learning constraints, and distinguishing valuable needs from distracting customization.

Her three closing lessons for entrepreneurs were simple: use your own product, don’t be afraid to fire customers who are the wrong fit, and grow your team carefully.

Full chat with Irina Calciu on Lessons from Building AI Systems, Products, and Startups

Related Blog Posts

• Bill Grosso on Startups after AI
• Build a Cannon to Kill a Mosquito with Mani Doraisamy
• Martin Hernandez Navarro on Data Science, Big Data, and AI
• Andrew Shindyapin: AI’s Impact on Software Development
• Matt Trifiro on Lessons Learned using AI for Marketing
• The AI Gold Rush: It Still Takes Teams
• Frank Tisellano: “Business First” Product Management
• Moe Arnaiz: Lessons Learned Bootstrapping eMOBUS and Weeldi
• Qualitative Research: Problem Exploration for Lean Startups
• Lean Culture Startup Community

Quotes for Entrepreneurs Curated In September 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 collect them in a blog post that adds commentary and may contain a longer passage from the same source for context.

My theme for the September 2026 “Quotes for Entrepreneurs” is character and ability, personal qualities that both benefit from ongoing cultivation.

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“Character is simply habit long continued”
Plutarch in “On Education“

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“Success isn’t finding the one trick or secret nobody knows. It’s doing the boring things everyone knows about but are too undisciplined to do. Get good at being boring.”
Mark Manson in a Sep-1 tweet

In “Pick Boring Or Grinding Over Losing Money” I suggested that, “The sad reality is that a business cannot be fun, educational, and profitable all at once. Pick boring or grinding over losing money.”

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“Character consists of what you do on the third and fourth tries.”
James Michener in Chesapeake

h/t WIST; more context

“For a woman to achieve her capabilities she must have an example. She cannot discover the truth by herself.”

“What example had you?”
“William Shakespeare.”
“What does that mean?”
“It means that I was an ugly child–had no young men pursuing me–and in God’s grimness I could do nothing but read. I read all of that heavy book you see on the table near the window, and I warrant it hasn’t been opened since I left.”
“I couldn’t understand Shakespeare,” Mark said honestly.
“Nor could I…the first two times. Character consists of what you do on the third and fourth tries.”

James Michener in Chesapeake

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“Talent is a gift, but character is a choice.”
John C. Maxwell in “21 Indispensable Qualities of a Leader” (section heading)

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“Character–the willingness to accept responsibility for one’s own life– is the source from which self-respect springs. Self-respect is something that our grandparents, whether or not they had it, knew all about. They had instilled in them, young, a certain discipline, the sense that one lives by doing things one does not particularly want to do, by putting fears and doubts to one side, by weighing immediate comforts against the possibility of larger, even intangible, comforts.”
Joan Didion in On Self-Respect

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“It’s good to do uncomfortable things. It’s weight training for life.”
Anne Lamott in Plan B: Further Thoughts on Faith

I originally curated this in December 2015.

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“Occasions of adversity best discover how great virtue or strength each one hath. For occasions do not make a man frail, but they show what he is.”
Thomas à Kempis in “The Imitation of Christ” (c. 1418)

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“There is only one proof of ability—action.”
Marie von Ebner-Eschenbach, in Aphorisms (1880–93)

Originally curated in February 2025. Sometimes the ability to be patient, to wait until the time is ripe, is also proof of ability or character. Benjamin Disraeli observed: “Next to knowing when to seize an opportunity, the most important thing in life is to know when to forego an advantage.”

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“People’s beliefs about their abilities have a profound effect on those abilities. Ability is not a fixed property; there is a huge variability in how you perform. People who have a sense of self-efficacy bounce back from failures; they approach things in terms of how to handle them rather than worrying about what can go wrong.”
Albert Bandura in “Self-Efficacy: The Exercise of Control” (1997)

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“It all goes so fast, and character makes the difference when it’s close.”
Jesse Owens

quoted in Jesse Owens, Champion Athlete (1990) by Tony Gentry

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“Character is a strange blending of flinty strength and pliable warmth.”
Robert H. Shaffer

I originally curated this in November 2023, noting: “To survive and manage the rich variety of situations we encounter in this life you need a range of strategies you can employ effectively. I like Shaffer’s suggestion that we need to combine hard strength with encouraging support as the situation requires. When you find yourself over your head or in a survival situation you will need to be able to try different approaches to persevere.”

It reminds me of this quote by Edna O’Brien I curated in November-2010 and January-2012:

“When anyone asks me about the Irish character, I say look at the trees. Maimed, stark, and misshapen, but ferociously tenacious.”
Edna O’Brien

I think this matches the character of many successful entrepreneurs who are not Irish as well.

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“Judge of your natural character by what you do in your dreams.
If you yield to temptation there, I am afraid you will, awake.
If you are a coward then, I jalouse of your courage by day.
Ralph Waldo Emerson in journal entry for “Naples March 12, 1833“

Jalouse is an old Scottish verb meaning to suspect or surmise. I am not sure that Emerson is accurate about dreams: may be as much our exploring implications of potential actions and exploring the impossible to find the limits of the possible.

“The only way of discovering the limits of the possible is to venture a little way past them into the impossible.”

Arthur C. Clarke in “Profiles of the Future” (1962)

This was reworked by Clarke in a 1972 talk “Report on Planet Three and Other Speculations” as “Clarke’s Second Law: The only way to discover the limits of the possible is to go beyond them into the impossible.”  h/t Garson O’Toole (Quote Investigator) in “Limits” for history of Clarke’s Second Law.

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“Man is like a card-player who receives from Nature his cards—his disposition, his circumstances, the strength or weakness of his will, of his mind, and of his body. The game of life is one of blended chance and skill. The best player will be defeated if he has hopelessly bad cards, but in the long run the skill of the player will not fail to tell. The power of man over his character bears much resemblance to his power over his body. Men come into the world with bodies very unequal in their health and strength; with hereditary dispositions to disease; with organs varying greatly in their normal condition. At the same time a temperate or intemperate life, skillful or unskillful regimen, physical exercises well adapted to strengthen the weaker parts, physical apathy, vicious indulgence, misdirected or excessive effort, will all in their different ways alter his bodily condition and increase or diminish his chances of disease and premature death. The power of will over character is, however, stronger, or, at least, wider than its power over the body. There are organs which lie wholly beyond its influence; there are diseases over which it can exercise no possible influence, but there is no part of our moral constitution which we cannot in some degree influence or modify.”

William Edward Hartpole Lecky in “The Map of Life: Conduct and Character” (1900)

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“Character is Destiny”
Heraclitus

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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.” I originally curated this in November 2022.

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“Character is what emerges from all the little things you were too busy to do yesterday, but did anyway.”
Mignon McLaughlin in  “The Second Neurotic’s Notebook” [Archive.org]

I like this quote and believe it is especially good advice for bootstrappers who are always pressed for time since they have less money to trade for time, at least in the early going. I have curated it twice before, first in December 2009 and again in November 2014. If I am still above ground and blogging in the 2030s I will doubtless find one or two more uses for it. I like a lot of McLaughlin’s aphorisms.

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“The acquisition of one sort of ability often makes that of another unlikely, if not impossible…To take the gifts one does have to concentrate one’s strength upon their development to disallow distractions–none of these is an easy task.”
Joseph Epstein in “Ambition: The Secret Passion” (1980)

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“There are many rare abilities in the world, which Fortune never brings to light.”
Thomas Fuller in Gnomologia

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“A special ability means a heavy expenditure of energy in a particular direction, with a consequent drain from some other side of life.”
Carl Jung

I am not sure I believe this completely, but it’s certainly the case that you cannot “ride out in all directions at once” and get good at everything at the same time.

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“The brain grows to the exact modes in which it has been exercised. Man is, par excellence, the educable animal.”
William James “Principles of Psychology” 1890

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“The world is created by fewer men than we often realize, and they tend to be more extraordinary than we’d like to acknowledge. Ground floor, it’s hard to replace people like this.”

Mike Solana in Flexport: Return of the King (Sep 13, 2023)

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“Uncertainty is not a property of the world, but of our relationship with the world”
David Spiegelhalter in “The Art of Uncertainty”

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“I always keep a bottle of chilled champagne on hand, just waiting for something to celebrate. And when I visited a friend after a sad event, I took them a bottle and told them to set it aside for when good things happened in the future, because they would. And, later, they did and they even called me to tell me they drank it. That’s faith in the future, and so far it’s worked out for me pretty well.”

Glenn Reynolds in A Tale of Two Centuries

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Image Credit: Moon with a wisp of cloud by Steve Houston. Used with Permission.

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

In “9/11 A Quarter Century On…it may be time to point our eyes forward” Cdr Salamander (@cdrsalamander) suggests, “It is time that we move on and stop treating 9/11 as a secular holy day of some sort. […] We should not forget 9/11, but it should be put is a place like the Fall of Saigon was in 2001, and the attacks on Pearl Harbor were in 1965. I think it is time.”

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

Image credit: “Questions licensed from 123rf.com/profile_maxborovkov 211007599

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 do 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. You are also welcome to drop by a Bootstrappers Breakfast, a number of serial entrepreneurs join us to kibitz and renew their gumption.

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

This post was republished on LinkedIn as https://www.linkedin.com/pulse/overcoming-post-acquisition-letdown-sean-murphy-x1huf/

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 Sellers–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