A collection of quotes for entrepreneurs curated in June 2025 around a theme of growth, expansion, and scaling up.
Quotes For Entrepreneurs Curated in June 2025
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.
My theme for this month’s “Quotes for Entrepreneurs” is growth, expansion, and scaling up.
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“Work hard and take everything really seriously.
Wisdom is acquired by experience.
Energy begets energy
I attribute a lot of my career path to my working really hard and caring a lot about things.
When you find a good thing to focus on and pour energy into, it can be positive-sum. It can give you energy in the rest of your life, give you a sense of purpose.”
Tom MacWright in “Work hard and take everything really seriously“
His idea of working at pouring your energy into the right things is positive sum reminds me of a passage from “Slide Rule” by Nevil Shute where he writes, “I have always liked to do two jobs at the same time; one helps you to rest from the other.”
“I must have had a good deal of energy in those days, because on summer mornings I used to get up at about half-past five, drive six or seven miles to Chislehurst, where there was a livery stables, ride for an hour on Chislehurst Common, and get back in time to bathe, breakfast, and catch my train to Crayford. I think I felt that my surroundings at that time were so drab that it was necessary to regain contact with the country and do something different from all the other daily-breaders; I think the airship calculations benefited from these early morning rides, and perhaps they benefited from the novel, too. I have always liked to do two jobs at the same time; one helps you to rest from the other, and the fact that in the evenings my mind was fully occupied upon the novel gave me a clearer view of the airship problems next morning, I think, than some of my colleagues could achieve.”
Nevil Shute in “Slide Rule: The Autobiography of an Engineer“
“Daily-breaders” is British slang for commuters. More excerpts from Tom MacWright’s essay “Work hard and take everything really seriously”
“For me to really understand something, I need to build it two or three times, write about it, use it incorrectly, and learn the consequences. Working hard meant playing around, having fun, but essentially playing with a lot of things that were not directly part of what I was paid to do at that time. This, honestly, worked out extremely well and some of those things led to jobs and opportunities that I never would have had otherwise.
When your priorities shift, you’ll know: most people gain new responsibilities. You’ll have a baby or a family member to take care of, or a thriving social life that demands more of your time. Your priorities will snap into place and you’ll realize that you care about new things. This is great.
But before you have those new responsibilities, you don’t have those new responsibilities. You don’t have to prematurely act like you’re older.
You can burn out by going too fast, or your flame can dim because you don’t let yourself spend silly amounts of time on silly projects to satisfy your intellectual curiosity. Beware of both outcomes: cultivate your enthusiasm for the things you want to hang onto.
It isn’t a revolutionary idea that people who are excellent in their fields often get there by trying really hard. If you can figure out the difference between busy-work that only benefits your employer, and the kind of work that makes you as a person feel like you’re making progress and becoming more skilled, then you’re ready to learn.
Tom MacWright in “Work hard and take everything really seriously“
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“High achievement always takes place in the framework of high expectation.”
Charles Kettering
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“A man on a thousand mile walk has to forget his goal and say to himself every morning, ‘Today I’m going to cover twenty-five miles and then rest up and sleep.”
Leo Tolstoy in “War and Peace”
One common piece of advice you hear at a Bootstrappers Breakfast is “a startup is a marathon not a sprint.” Also applies to other self-improvement and organizational change efforts as well as your career and your life. See also “Successful Entrepreneurship Is Ongoing Self-Improvement.”
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Dan Hockenmaier: At the end of the day, the only flywheel that matters. Whoever spins it the fastest wins.
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“Just as the Panama Canal promised to bring east and west together, so Vail was now promising a corresponding revolution in communication [with transcontinental telephone service]. Observers could be forgiven, however, for interpreting the boast about transcontinental telephone services as a fait accompli. After all, they’d seen the unmistakable combination of innate American self-promotion combined with can-do brute force before. Wasn’t this the building of the Transcontinental Railroad all over again?
It was not. The pledge required technology that had not yet been developed. Long-distance service had expanded with the development of balanced metallic circuits, mechanical repeaters, and most recently, loading coils. But the technological innovations existing in 1909 could not provide commercially feasible transcontinental communications. Voice distortion caused by each mechanical repeater limited the number that could be used and sending a signal from one point to another. Loading coils, the most recent breakthrough in long-distance telephony, would similarly find their limits in the New York-to-Denver line.”
Stephen B. Adams and Orville R. Butler in “Manufacturing the Future: A History of Western Electric“
It’s interesting that linear growth, or a simple scale-up of a structure, design, or organization, often entails both super-linear increases in cost and performance problems that occur above a threshold of complexity that was not apparent in a smaller implementation. Sometimes, a phase change occurs that is not obvious from behavior or structure below the threshold: you can heat water out of the tap for many minutes before it suddenly bubbles into steam.
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“Peter Palchinsky realized that most real-world problems are complex, they have a human dimension, a local dimension, and change as circumstances change. He developed three methods to deal with this complexity:
- Seek new ideas and try new things;
- Try something new at a scale where failure is survivable;
- Seek feedback and learn from mistakes as you go.”
Tim Harford (Undercover Economist) in “Adapt: Why Success Always Starts with Failure“
#2 reminds me of Dave Snowden’s concept of “safe to fail” probes and the value of plan to dampen any negative consequences prepared before you try the new idea.
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Though the world does not change with a change of paradigm, the scientist afterward works in a different world. […] What occurs during a scientific revolution is not fully reducible to a re-interpretation of individual and stable data. In the first place, the data are not unequivocally stable.”
Thomas Kuhn “Structure of Scientific Revolutions”
A new product that is a platform for a new paradigm can have the same effect. Examples include the steam engine, the dynamo, VisiCalc, Mosaic, and YouTube.
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“The doers are the major thinkers: the people who create the things that change this industry are both the thinker and the doer in one person.”
Steve Jobs in what is know as “Lost Interview” from 1990 with WGBH Nova series “The Machine that Changed the World.“
Jobs’ thinking-doing model reminds me of “Pasteur’s Quadrant” by Donald Stokes. Stokes postulates that Pasteur was so effective because he solved problems and advanced theory at the same time. This approach contrasted Niels Bohr, who ran experiments that advanced theory, and Thomas Edison, who solved problems without advancing models or theory. In the lower left quadrant is someone like Linnaeus or Roger Torey Peterson, who engaged in structured observations, categorizing what they could observe without developing theories or solving problems–but laying the groundwork for the other three kinds of actors.
More context
“My entire life’s been spent only in one industry, but I’ve been in it now for about 15 years, and I’ve seen a lot of people make a lot of things. I’ve seen a lot of people fail at a lot of things. And my point of view on this is that the doers are the major thinkers. The people who create the things that change this industry are both the thinker and the doer in one person.
If we examine Leonardo Da Vinci, did he have a guy off to the side who was thinking about what he would paint five years out in the future or the technology he would use to paint it? Of course not, Leonardo was the artist, but he also mixed all his own paints. He also was a fairly good chemist. He knew about pigments and human anatomy, and combining all of those skills, the art and the science, the thinking and the doing, led to exceptional results.
And there is no difference in our industry—the people who really made the contributions have been the thinkers and the doers. It’s very easy to take credit for the thinking. The doing is more concrete. It’s very easy for somebody to say, ‘Oh, I thought of this three years ago.’ But usually, when you dig a little deeper, you find that the people who really did it were also the people who really worked through the hard intellectual problems as well.”
Steve Jobs
h/t All About Steve Jobs website: “Future of PC 1990” (also known as “Lost Steve Jobs Interview“). Also at https://archive.org/details/interview.with.steve.jobs.V_AD9E0BC353BF435E83F28DEF165D4F40
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“The greatest achievement of our technology may well be the creation of tools that allow us to go beyond engineering–that allow us to create more than we can understand.”
Dany Hillis “The Pattern on the Stone” (1999) [Archive]
h/t Steve Jurvetson in “Deep Learning: Intelligence from Big Data” (Sep-16-2014). This is true for many breakthroughs: the invention precedes the theory that explains it–or allows improvements that move from trial-and-error to engineering. Sometimes the breakthrough is a new instrument that extends the range of our perceptions in useful ways that allow us to refine the impact of existing inventions. More context:
“I believe that we may be able create an artificial intelligence long before we understand natural intelligence, and I suspect that the creation process will be one in which we arrange for intelligence to emerge from a complex series of interactions that we do not understand in detail — that is, a process less like engineering a machine and more like baking a cake or growing a garden. We will not engineer an artificial intelligence; rather, we will set up the right conditions under which an intelligence can emerge.”
Dany Hillis “The Pattern on the Stone” (1999)
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“A salient is a protrusion in a geometric figure, a line of battle, or an expanding weather front. As technological systems expand, reverse salients develop. Reverse salients are components in the system that have fallen behind or are out of phase with the others. Because it suggests uneven and complex change, this metaphor is more appropriate for systems than the rigid visual concept of a bottleneck.”
TP Hughes “The evolution of large technological systems.” (1987) in “The Social Construction of Technological Systems p 51–82
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“The Wright brothers flew right through the smoke screen of impossibility.”
Charles F. Kettering
quoted in “Charles F. Kettering: A Biography” by Thomas Alvin Boyd (original 1957 title “Professional amateur The biography of Charles Franklin Kettering” [Archive] quoted on page 88).
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“There are basically two games you can play with your career:
- Game One is optimizing for company outcome. Focus all of your energy on finding the highest leverage problems in your company and fixing them.
- Game Two is optimizing for personal outcome. Seek external signals like title, scope, and team size. Make sure you’re on the right team and working on the right things.
Play Game One.”
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“If we wish to make a new world we have the material ready. The first one, too, was made out of chaos.”
Robert Quillen
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“I became interested in long-term trends because an invention has to make sense in the world in which it is finished, not the world in which it is started.”
Ray Kurzweil
Products and markets co-evolve, complicating your survival, much less your ability to scale. Customer needs change, new competitors alter prospects’ perception of your value, and infrastructure evolves, obsoleting the context of initial success. Product-Market fit requires ongoing adjustment. See Product-Market Fit is a Fraction Not a Bit for more on this.
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“Remarkably, the GMail team has shipped a product that perfectly captures the experience of managing an underperforming employee.”
Pete Koomen (@Koomen) in AI Horseless Carriages
More context
Prompt: Let my boss Garry know that my daughter woke up with the flu this morning and that I won’t be able to come in to the office today.
MessageDear Garry,
I am writing to inform you that my daughter woke up with the flue this morning. As a result, I won’t be able to come into the office today.
Thank you for understanding.
Best Regards,
PeteAs you can see, Gemini has produced perfectly reasonable draft that unfortunately doesn’t sound anything like an email that I would actually write. If I’d written this email myself, it would have sounded something like this:
Hey garry, my daughter woke up with the flu so I won’t make it in today
The tone of the draft isn’t the only problem. The email I’d have written is actually shorter than the original prompt, which means I spent more time asking Gemini for help than I would have if I’d just written the draft myself. Remarkably, the GMail team has shipped a product that perfectly captures the experience of managing an underperforming employee.
Pete Koomen (@Koomen) in AI Horseless Carriages
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When a startup is first founded, it is nothing but risk. Successfully building a company is the act of slowly eliminating that risk until you have created a reliable cash flow machine.
There are five types of risk:
- Technology risk – can we get the product to work?
- Market risk – can we build something people love?
- Scaling risk – can we acquire lots of customers?
- Business model risk – can we serve customers profitably?
- Defensibility risk – can we maintain market share?
Dan Hockenmaier in “When to Join a Startup“
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“There is no bigger waste of time than doing 90 percent of what is necessary.”
Thomas Sowell? in “Is Reality Optional” (1993)
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“It is far better to weight the opinions of more capable decision makers more heavily than those of less capable decision makers. This is what we mean by “believability weighting.” So how do you determine who is capable at what? The most believable opinions are those of people who 1) have repeatedly and successfully accomplished the thing in question, and 2) have demonstrated that they can logically explain the cause-effect relationships behind their conclusions. ”
Ray Dalio “Believability Weight Your Decision Making“
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“Novelty ordinarily emerges only for the man who, knowing with precision what he should expect, is able to recognize that something has gone wrong. Anomaly appears only against the background provided by the paradigm. […] In the normal mode of discovery, resistance to change ensures that the paradigm will not be too easily surrendered; it guarantees that scientists will not be lightly distracted.”
Thomas Kuhn in “Structure of Scientific Revolutions” [Archive]
A critical aspect of successfully managing growth and scaling an organization is vigilance against results departing from plan, prior experience, or expectations. The challenge is that real life has a lot of noise, complicating your assessment of whether you are experiencing “normal variation,” a potential problem, or an actual problem. More context:
“Discovery commences with the awareness of anomaly, i.e., with the recognition that nature has somehow violated the paradigm-induced expectations that govern normal science. It then continues with a more or less extended exploration of the area of anomaly. And it closes only when the paradigm theory has been adjusted so that the anomalous has become the expected. Assimilating a new sort of fact demands a more than additive adjustment of theory, and until that adjustment is completed—until the scientist has learned to see nature in a different way—the new fact is not quite a scientific fact at all. […]
Normal science leads to a detail of information and a precision of the observation-theory match that could be achieved in no other way. […]
Without the special apparatus that is constructed mainly for anticipated functions, the results that lead ultimately to novelty could not occur. And even when the apparatus exists, novelty ordinarily emerges only for the man who, knowing with precision what he should expect, is able to recognize that something has gone wrong. Anomaly appears only against the background provided by the paradigm. […]
In the normal mode of discovery, resistance to change ensures that the paradigm will not be too easily surrendered; it guarantees that scientists will not be lightly distracted.”
Thomas Kuhn in “Structure of Scientific Revolutions” [Archive]
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“A nation’s debt is a numerator in a fraction. The denominator is the size of the economy incurring the debt. When government policy permits growth, the numerator (the debt) shrinks in importance. Often enough, the better way to overcome debt is to grow yourself out of it.”
Amity Shlaes in “Forgetting the Denominator“
Often true for startups as well. This is not an argument for using credit card or other high interest loans to get started but it’s worth considering regular interest loans for expansion when you have debugged your quote-to-cash timeline and probabilities.
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“Learn Ask Do – Why Not Give It a Try?” Janis Ozolins
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“I’ve never began any important venture for which I felt adequate prepared.
Without knowing for sure what’s right or wrong, take your best shot.
There’s just no way to get it all straight. Mistakes are inevitable.”
Sheldon Kopp in What Took You So Long? (1979)
h/t Ed Bautista; Scaling combines the alternating sensations of a feeling of progress with being over your head.
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“Entrepreneurs sign the front of the check.”
Scott Galloway in Entrepreneurs sign the front of the check
Founders sell to meet payroll not quota.
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“Confusion that never stops
Closing walls and ticking clocksCursed missed opportunities
Am I a part of the cure
Or am I part of the disease?”
I thought these lines captured the challenges of scaling. You achieve mastery and then feel it slip away as the problems get harder. Half of the time the tactics that used to work well are now the wrong thing to do.
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“The natural implementation of a new feature is addition, leaving other elements in place. As this process repeats, the simplicity of a system is lost, and complexity takes its place. ”
Edited summary of Alex Gaynor in “Why Software End Up Complex“
This default approach of incremental construction without architecture or reconceptualization is not only a risk for software but for organizational growth. Here is a longer excerpt for more context:
“The most natural implementation of any feature request is additive, attempting to leave all other elements of the design in place and simply inserting one new component: a new button in a UI or a new parameter to a function. As this process is repeated, the simplicity of a system is lost and complexity takes its place. […]
Every feature request has a constituency – some group who wants it implemented, because they benefit from it. Simplicity does not have a constituency in the same way, everyone benefits from it. This means that supporters can always point to concrete benefits to their specific use cases, while detractors claim far more abstract drawbacks. The result is that objectors to any given feature addition tend to be smaller in number and more easily ignored. Leading to constant addition of features, and subtraction of simplicity.
We need to spend as much time thinking about how a new feature will burden all of our users, as we spend thinking about how it will benefit some of our users. We should also spend time thinking about how to design new features in a way that maintains what Fred Brooks’ called the “conceptual integrity” of a system, rather than by merely tacking something new on.”
Alex Gaynor in “Why Software End Up Complex“
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“I would define the middle class as the people who expect their kids to do better than themselves.”
Peter Thiel in an interview with Ross Douhat [archive.is]
I think founders adopt a “middle class” attitude toward the future of their companies. Thiel continues, “And when that expectation collapses, we no longer have a middle-class society.” I think that’s also a model for how promising high-growth firms collapse into bureaucracy. They on longer hold themselves accountable for raising the bar, for high levels of achievement and increasing customer value.
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“Do not stand in a place of danger trusting in miracles. ”
Tahir Shah in The Caliph’s House: A Year in Casablanca (2006)
I have also seen this described as an African or Arab proverb, but none of the references seem to predate Shah’s publication date of 2006. I think this is a good rule of thumb for a growing business, every expansion carries risk and sometimes danger. You can hope for the best but remember advice ascribed to Hunter Thompson, “Pray to God, but row away from the rocks.” and this from Hippocrates:
“Prayer indeed is good, but while calling on the gods a man should himself lend a hand.”
Hippocrates in Regimen, Book IV, Section 87 [Archive]
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“Doing qualitative analysis can be a little arduous, which explains the popularity of tools that purport to help teams skip right to the insights.
While it’s important to make good use of everyone’s time, generating insights faster with less human participation might actually increase the amount of research that goes unused.
The goal of research is to change the behavior of decision-makers in favor of more evidence-based action. Behavior change is hard. And having more facts about the world around doesn’t mean people are going to act in accordance with them (especially if those facts contradict existing beliefs).
Research benefits from the IKEA effect. Everyone who had a hand in creating the insights will value them more, and have a better chance of remembering what was learned.”
Erika Hall in a LinkedIn post “Doing Qualitative Analysis“
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Image Credits:
- 5 types of startup risk by Dan Hockenmaier in “When to Join a Startup” used with attribution.
- “Learn Something Valuable -> Turn it into a Product or Process” by Dan Hockenmaier, used with attribution.
- 3 days vs. 3 years by Janis Ozolins used with attribution