The Other Venture: Coaching Entrepreneurs at Cambridge
Every founder builds two ventures: the company and the person the work is quietly forming.
When I began coaching entrepreneurs through Wolfson College’s Entrepreneurship Hub at the University of Cambridge, I expected business questions.
They came, but they rarely remained business questions for long.
Should I trust this partner? Take the money? Change direction? Keep going?
Beneath each decision waited another, quieter set of questions. Can I trust my judgment when the evidence is incomplete? Which ambitions are truly mine? What will this work require me to become?
Every founder starts two ventures. One receives a name, a legal structure, and a bank account. The other is harder to register.
It is the founder.
The first venture is visible. Customers test it. Investors price it. The market is seldom polite about it. The second is formed in private, through every compromise resisted, every rejection survived, every difficult conversation postponed or begun.
A company can grow faster than the judgment of the person leading it. That is where coaching earns its place. Not by giving the founder a borrowed mind, but by helping the founder use their own.
Advice Has an Ego
Advice likes to arrive early. It enters the room with its coat still on and begins rearranging the furniture.
At Cambridge, where intelligence is plentiful and opinions are rarely undercapitalized, the temptation to provide an impressive answer was real. An answer makes the coach feel useful. A good question can feel almost negligent by comparison.
Yet premature advice is often the coach’s anxiety dressed as expertise.
Sometimes advice is precisely what a founder needs. It becomes dangerous when it relieves the coach before it strengthens the person who must live with the decision.
Martin Buber, the twentieth century Jewish philosopher of human encounter, distinguished between meeting another person as a Thou and reducing that person to an It. The distinction belongs in the coaching room. A founder can be encountered as a living subject, capable of judgment and surprise, or managed as a problem, a case, a demonstration of the coach’s method.
My leadership and performance coaching training through Brown University and ACT Leadership gave discipline to this attention. At Cambridge, I listened beyond the stated problem: for repeated words, changes in energy, careful evasions, and the silence following an important question. I listened for the value being defended and the fear hiding inside impeccable logic.
Deep listening is not passive. It is the disciplined refusal to answer before discovering which question is actually being asked.
Intelligence can fill a room. Coaching must make room.
The Best Is Often Seen First by Someone Else
The best in another person is rarely invisible. More often, it is unrecognized, especially by the person carrying it.
This required something more exacting than encouragement: acknowledgment. Praise offers approval. Acknowledgment offers evidence. It names the capacity beneath an action: the courage required to begin again, the judgment exercised in refusing an attractive distraction, the honesty required to release an ambition that no longer fits.
People often know their deficiencies by heart. Their strengths can remain strangers.
Acknowledgment returns evidence to its owner. The coach does not manufacture the quality or award it like a medal. The coach notices what is already appearing and names it clearly enough for the other person to recognize and use.
Richard Boyatzis, an organizational psychologist who studies leadership and intentional change, contrasts coaching toward a person’s desired future with coaching centered on correction or compliance. One begins with deficiency. The other begins with possibility.
Often, I could hear the future before either of us could name it. A voice would lift. A sentence would grow longer. A dismissed idea would return with more detail and less apology. None of this was proof. It was an invitation to become curious.
What changed just now? What matters about that possibility? When have you seen this capacity in yourself before?
Seeing the best in someone does not mean imagining them flawless. It means refusing to confuse what is unfinished with what is final.
Care Without Capture
I once described good coaching as loving others into being. The phrase risks grandeur, so it requires precision. A coach does not create another person. A coach creates the conditions in which that person can exercise authorship.
Here, love means attention without possession, candor without conquest, and confidence in another person’s capacity without the vanity of imagining that we created it.
Edward Deci and Richard Ryan, the psychologists who developed self determination theory, identify autonomy, competence, and relatedness as basic conditions of healthy motivation. In plain English, people need choice, capability, and connection.
Good coaching should strengthen all three. The founder should leave with greater ownership of the decision, greater confidence in the capacity to act, and less isolation within the uncertainty.
At times, I invited entrepreneurs to remember themselves at their best. What qualities were present? What mattered enough to call those qualities forward? At other times, we looked ahead. If the venture succeeded without costing them what they valued most, what had they protected? Who had they learned to become?
Pressure shrinks time. Everything becomes immediate and close to the skin. A future perspective allows someone to examine the present from a place where today’s fear does not command the entire horizon.
Care also requires challenge. Limiting beliefs rarely introduce themselves as beliefs. They arrive dressed as facts. Reframing does not repaint reality in cheerful colors. It asks whether one failure has been promoted into an identity, caution has become captivity, or an old conclusion still governs a life it no longer describes.
Fear may contain information. It should not automatically chair the meeting.
Compassion without challenge becomes consolation. Challenge without compassion becomes conquest.
A coach cannot decide what another person’s best self should be. The moment the coach prescribes the identity, care becomes capture.
If a client leaves impressed by the coach but less able to think without the coach, the performance has succeeded and the coaching has failed.
Give Possibility Something to Do
Founders are expected to imagine markets that do not yet exist. They are less often invited to imagine the person capable of building them.
A founder can produce a model with seventeen tabs and still be unable to answer the simplest question in the room: Do I want this life?
Spreadsheets are excellent at modeling cash. They are less gifted at modeling regret.
Possibility, however, cannot remain imaginary. Entrepreneurship gives it consequences.
Saras Sarasvathy, an entrepreneurship scholar at the University of Virginia’s Darden School of Business, found that expert entrepreneurs often begin with the means already available: who they are, what they know, and whom they know. They cannot command the future. They can choose the next responsible experiment.
So the conversation returned to something real: a difficult call, a boundary, a prototype, a decision. What will you do? By when? What support will you need? The action belonged to the founder. So did the accountability.
The movement was not a staircase but a rhythm. See what is true. Name what is worth pursuing. Recover what can still be chosen. Act. Then notice what the action is making of you.
Every experiment tests two propositions: whether the venture can work and whether the founder can lead it without becoming smaller.
What Cambridge Gave Back
I arrived with frameworks. The entrepreneurs brought unfinished companies and unprotected questions. The exchange was never one way.
They taught me to resist proving my usefulness too quickly, to sit with a question until the obvious answer lost its authority, and to admire ambition without flattering it.
Sometimes the earliest capital a founder needs is not money. It is another mind willing to take an unfinished idea seriously without pretending it is finished.
That is what the best coaching relationship offers. Not wisdom in one chair and need in the other, but a disciplined encounter in which attention reveals capacity, honesty sharpens ambition, and possibility becomes action.
The company may pivot, close, sell, or outgrow its first imagining. The other venture keeps walking, carrying forward new habits of courage or avoidance, judgment or dependence, authorship or surrender.
What remains is not only what the founder built, but what building required the founder to become.
The coach should not write the ending.
The coach should return the pen.
Bibliography
Boyatzis, Richard E., Melvin L. Smith, and Alim J. Beveridge. “Coaching With Compassion: Inspiring Health, Well Being, and Development in Organizations.” The Journal of Applied Behavioral Science, volume 49, number 2, 2013, pages 153 to 178. Read the article details.
Brown University School of Professional Studies. “Leadership Performance Coaching Certification.” Explore the Brown University and ACT Leadership program.
Buber, Martin. I and Thou. Translated by Walter Kaufmann. Charles Scribner’s Sons, 1970. Read an introduction to Buber’s philosophy.
Ryan, Richard M., and Edward L. Deci. “Self Determination Theory and the Facilitation of Intrinsic Motivation, Social Development, and Well Being.” American Psychologist, volume 55, number 1, 2000, pages 68 to 78. Read the article.
Sarasvathy, Saras D. “Causation and Effectuation: Toward a Theoretical Shift from Economic Inevitability to Entrepreneurial Contingency.” Academy of Management Review, volume 26, number 2, 2001, pages 243 to 263. Explore effectuation and its applications.
Wolfson College, University of Cambridge. “Entrepreneurship Society.” Explore Wolfson College’s entrepreneurship community.