Sam Shear and the value of a canceled order

A canceled order is an awkward thing to put at the center of a founder’s story. There is no ribbon to cut. Nobody frames the confirmation email. Yet Sam Shear has described a practice at Yes Hearing that makes the departing customer unusually important: when someone canceled an order or returned a purchase, the founders would get on the phone themselves.

Consider the arrangement. A chief executive spends much of his working life persuading people to believe in a business. Investors need a reason to commit. Recruits need a reason to join. Customers need a reason to buy. Here is a conversation with someone who has already declined the invitation. The sales pitch has received its answer, and the founder gets to discover what his pitch left out.

Shear discussed those calls in 2023, four years after launching Yes Hearing in New York and shortly after the company announced a $10 million Series A. The financing supplied an obvious milestone. The calls offered a more useful glimpse of the work: an entrepreneur allowing a customer’s decision to interrupt his own account of how the business ought to function.

There is a practical appeal to this. A cancellation is specific. Something happened between interest and departure. A founder can ask about that something. The answer may be inconvenient, but inconvenience has the advantage of being harder to dismiss when a person is explaining it directly to you.

London before New York

Shear grew up in London and graduated from University College London. He earned First Class Honours. His early career included a strategy role at Hypit, followed by sales and marketing at Houzz. Before running a company of his own, he had worked inside technology businesses where attracting customers was part of the job.

The sequence matters because it gives his later interest in canceled orders some context. Sales and marketing place a person near the boundary between a company’s intentions and a buyer’s willingness to participate. A proposition can sound perfectly sensible in a meeting. Someone still has to choose it while attending to the rest of their life.

At Houzz, Shear worked in the United Kingdom during the company’s expansion. He then chose the United States for his own venture. Yes Hearing launched in New York in 2019, with Oliver Philips as co-founder and chief operating officer. The move put the new business directly in the American market rather than treating America as a distant chapter in a future expansion plan.

It is tempting to make a transatlantic founding story entirely about geography: London on one side, New York on the other, ambition somewhere over the ocean. The more interesting distance is between working on somebody else’s expansion and becoming responsible for your own. Shear’s career crossed that distance in a few years. A title changes immediately; the obligations attached to it tend to arrive in installments.

A launch cannot wait for perfect

One of Shear’s more candid admissions concerns the period before a business is properly underway. He described getting caught in the pursuit of perfection. The plan could always be improved. There was always another reason to delay. His lesson was to establish a workable foundation, proceed, and repair what experience revealed.

That is a familiar problem with a particularly flattering disguise. Perfection sounds responsible. It can even look industrious: another revision, another discussion, another careful adjustment before anyone outside the team gets a vote. A founder may be very busy without becoming any better informed about what customers will actually do.

The canceled-order calls fit beside this admission. Launching lets the outside world respond. Calling a departing customer makes it possible to hear the response in more detail. Both practices require the founder to give up a little control over the story. A plan offers the comfort of consistency. A customer is under no obligation to respect the plot.

Shear’s account is useful precisely because he includes himself in the mistake. He does not present the early difficulty as something only other founders suffer. The admission leaves room for a less theatrical version of entrepreneurship, in which judgment develops through work and correction. That is a sturdier starting point than assuming conviction will settle every argument.

“Be prepared to fail.”

Sam Shear · 2023

Ten million dollars, and the work behind it

In November 2022, Yes Hearing announced its $10 million Series A. Blue Heron Capital led the round. Primetime Partners, Ensemble Innovation Ventures, Maccabee Ventures and Gaingels also participated. For Shear, the announcement marked a change in the resources available to the company and in the number of people with a stake in what happened next.

The stated plans included expanding direct-to-consumer operations and developing the company’s technology platform. Those purposes are less photogenic than the figure in the headline. They also describe what financing has to become if it is to matter: software, operating capacity, and a business able to handle more activity without asking every problem to queue outside the founder’s door.

Shear later spoke publicly about the advisory support Blue Heron brought to the company. The relationship adds another dimension to the fundraising story. Money creates options; experienced operators can help a founder judge which options deserve attention. An expanding company produces plenty of decisions before it produces much spare time.

The financing also brought a planned board appointment: Todd Walrath, CEO of HomeCare.com and ShiftMed. The announcement assigned him a role in developing partnerships and supporting nationwide growth. That addition makes the round more concrete. A board appointment establishes another working relationship around the chief executive, with experience and expectations attached. It also places Shear’s company alongside people whose careers have involved organizing services at scale. For a founder coming from sales, marketing and technology, the composition of that wider circle is part of the company-building story. The business now had more than its original team looking at the next stage.

A funding round can make a career appear to move in one clean leap. An announcement has a date and a number, both excellent conveniences for a headline. Building the organization around it is less tidy. The relevant question becomes how authority, information and responsibility move through a team as more people join it.

For a chief executive who has personally called departing buyers, that creates a real management puzzle. Direct contact can teach the founder something valuable. Growth requires the organization to learn it too. A conversation has limited value if its lesson remains trapped in the memory of the person with the busiest calendar.

The people beyond the pitch

Shear’s public advice to other entrepreneurs has included learning from people they hire and maintaining a support network. There is a modesty to that prescription. Founding gives someone a reason to be involved in almost everything at the beginning. It gives them no permanent entitlement to have the best answer afterward.

The distinction becomes more consequential as a company grows. Early involvement can become a habit of intervention. A founder who once had to make every decision may keep making decisions that colleagues are better equipped to handle. The alternative requires trust, and trust rarely provides the immediate satisfaction of doing the task yourself.

Shear’s partnership with Philips places another operator beside him from the beginning. Their titles divide chief executive and chief operating responsibilities. The public outline of the company is therefore a shared founding effort, with different jobs attached. Any account that turns the business into a single person’s uninterrupted performance would miss that basic arrangement.

The customer calls provide a useful counterweight to the language of leadership. There is nothing especially grand about asking someone why they left. It is ordinary conversational work. That may be why it tells us something: the founder has to be willing to spend time with an answer that will not automatically become a testimonial.

The next answer is still outside

By August 2026, Shear was still writing publicly about the company he launched in 2019. His account returned to the reasons for choosing the American market and to the ambition of reaching more people. The continuity is striking enough without a prediction attached. Seven years after the launch year, the founder was still explaining the problem that had persuaded him to start.

The outline of his career now includes a London upbringing, a UCL education, work in technology, a New York founding, a co-founder, and an institutional funding round. Those are useful coordinates. They become more interesting when set beside his admission that a sensible assumption can fail once a business meets the people it hopes to serve.

That admission gives the story some welcome friction. Entrepreneurs are often asked to tell their careers backward, arranging each previous job into preparation for an outcome that now seems inevitable. Shear’s account of learning leaves room for surprise. The early plan did not contain every answer. The people buying, declining and returning things had information the founders needed.

A canceled order cannot tell a chief executive everything. One conversation is one conversation. But it offers a concrete place to begin asking better questions, and a reason to keep the company’s explanations open to revision. It also makes the word “feedback” rather less bloodless. There is a person at the other end of the line.

The neat version of Shear’s story ends with a financing announcement. The more revealing version continues after an order disappears. The founder picks up the phone. For a few minutes, the person who chose to leave gets to set the agenda.