Howard Yeh and the trouble with being good on paper

Howard Yeh had done the work. As a young investment banker at Merrill Lynch, he had put in the hours, built the models, answered the requests and earned the confidence of senior colleagues. A venture capital job was waiting. Then a performance review presented him with a problem that another spreadsheet would do little to solve: he needed more presence.

The advice was specific. Speak before certainty arrives. Take a position. Participate instead of sitting quietly at the end of the table. For someone accustomed to making preparation his contribution, this was an unfamiliar assignment. The work had been good. The person doing it needed to become more visible.

In March 2026, more than twenty years later, Yeh was still thinking about that conversation as he prepared for a leadership panel at Penn’s Pan-Asian American Community House. His recollection contained a candid admission: being dependable had become a strategy for being noticed. He had expected the output to make the introduction.

“My work needed a voice - and the willingness to use it.”

Howard Yeh, reflecting on his early career

Trading the model for the business

His original route was orderly enough to reassure a career counselor. Wharton, class of 2000. Finance, with an English minor. Merrill Lynch’s media investment banking group. Then VantagePoint Venture Partners, where he worked from 2003 to 2007 and advanced from associate to vice president. The sequence offered a sustained education in how other people’s companies worked.

At Merrill, the assignments included valuations, financing models, transaction research and presentations. His recollection of the job makes room for the abundant PowerPoint. At VantagePoint, he examined investments and worked around founders confronting the less tidy business of keeping a company moving. Building began to interest him more than advising.

In 2007, he changed course. Working with other founders, he joined the effort behind the original Healthcare.com business, which evolved into BrokersWeb. As co-founder and COO, he helped develop a customer acquisition operation. The business grew past $50 million in annual revenue in 2011, by his account. That September, BrokersWeb and Vantage Media announced their combination.

Yeh went on to co-found ContactUs.com in 2012, applying his attention to the seemingly unglamorous problem of capturing and following up on customer inquiries. WorkWave acquired it in 2015. A website contact form is unlikely to inspire a film franchise. It can, however, sit directly between a business and its next customer.

In 2014, he co-founded the new Healthcare.com with Jose Vargas and Jeff Smedsrud. His responsibilities would change through CEO, COO and Chief Revenue Officer. The company’s March 2021 announcement formalized his move from CEO to COO as Don Loonam took the chief executive role. Today, Yeh’s own account identifies him as co-founder and CRO, leading the Consumer business.

A board meeting, with improvised blinds

The more revealing account of his working life begins with office supplies. In February 2016, Yeh described consecutive board and team leader meetings in a Miami office where the blinds had yet to arrive. Disposable tablecloths, attached with masking tape, were serving in their place. Entrepreneurship had acquired its own window treatment.

The team was taking stock after its first year of meetings as a company. Business had improved, and its plans were becoming more grounded in evidence. Yeh used the occasion to examine assumptions that had looked reasonable at the start: that ideas would work, hires would quickly master their assignments and other people would share the founders’ enthusiasm.

He included himself in the review. This was his third startup, and he recognized mistakes he had made before. Experience had given him something to compare the present with; it had apparently declined to make him immune.

His recommendation was practical. Discover what the company can do well, concentrate on it and reduce the number of competing ambitions. A first-year team is learning its capabilities while trying to establish credibility. Its plans have to survive that discovery. The scene in Miami makes the argument tangible: there are decisions to make even while somebody is still finding the masking tape.

The things worth writing down

By June 2017, Yeh was describing another modest instrument of management: an Evernote note. He kept track of moments when people on his team surprised him. Each entry recorded a name, date, whether the surprise was positive or negative, and a short explanation.

The idea grew from advice he had read for engineering managers, but his examples extended beyond technical work. An employee might find an unexpected route through a business problem, make an unusual effort or teach themselves something faster than anticipated. Those moments could reveal development that a schedule of completed tasks would barely register.

Negative surprises belonged in the record too. A missed deadline without warning carried information about communication. The point was to retain enough detail to celebrate or coach a person properly, instead of letting the most recent event monopolize a later evaluation.

There is something appealingly unceremonious about the method. No new department is required. Someone has to notice, and then remember. For a former analyst whose own performance review remained vivid decades later, paying attention to another person’s progress seems an especially fitting discipline.

Fast experiments, longer memories

His technical writing supplies the operating detail behind that interest in development. In 2017, he set out twenty rules for conversion optimization, the repeated testing of changes to a customer’s path through a website. The rules dealt with hypotheses, priorities, measurement and the pace of releases.

Arthur Kosten, an advisor and investor with experience building Booking.com’s optimization practice, influenced his thinking. Yeh admired the rhythm of teams that kept testing. He also acknowledged the difference between the resources of a large operation and those available to his own company. The useful habit could travel even when the head count could not.

His instructions were more nuanced than a command to obey the numbers. Define success before launching. Have a reason for the experiment. Look at the customer’s journey before arrival as well as after it. Record what happens. An unsuccessful variation can still teach the team something. An inconclusive result requires judgment about the next step.

That last point matters to his portrait. Yeh explicitly made room for intuition in choosing experiments and interpreting incomplete evidence. The former financial modeler was arguing for a practice that needed both measurement and a person prepared to decide.

In a later essay about speed, he found an unlikely example in a cotton candy eating contest. A competitor’s decisive approach prompted him to think about how teams choose to move quickly. A piece of passing entertainment became a management question. His preferred examples do not always arrive wearing a tie.

The Eagles, the Sixers and the cost of going alone

The English minor has company in Yeh’s archive. In June 2017, he interpreted the Eagles’ “Desperado” as advice for founders. His reading moved through focus, spending, customers and the danger of trying to carry a company alone. A familiar song became a reminder that independence can come with an expensive shortage of people in your corner.

He also warned against taking other founders’ polished public updates as a complete account of their lives. Companies run into difficult periods. Their leaders still have to make decisions and hold uncomfortable conversations. His optimism allows for those chores. It has work to do.

Basketball receives a longer examination. A Philadelphia 76ers fan, Yeh wrote in 2016 about Sam Hinkie’s departure and the limits of a long-term strategy. He admired the attempt to approach team building with an investor’s discipline. He also considered why that approach needed support from people with different interests and different amounts of patience.

Owners, fans, advertisers and players all had a stake. An analytically attractive plan still had to keep enough of them willing to continue. Yeh’s interest lay partly in that tension: a decision could look sensible within a model while becoming difficult to sustain among actual people.

Read beside his note-taking habit and his early performance review, the essay adds another dimension to his working education. The numbers deserve attention. So do the people expected to live with them.

Still showing up for the next game

Outside work, there is another team to account for. Yeh co-captained Cherry Hill East’s volleyball team when it won its first state championship in 1996. The program was young; the opponents had longer histories. He still counts that season among his proudest memories.

He continues to play most weekends in New York, often with people roughly twenty years younger. Some are beginning careers in investment banking. Conversations at open gyms led him back to his own apprenticeship and toward a contemporary question: if AI accelerates the work junior professionals once learned by doing, how will they develop judgment?

His March 2026 essay treats the question as unfinished. Faster tools could support deeper investigation. They could also allow convincing output to get ahead of understanding. He is interested in how people learn to take responsibility for results, with enough experience and mentorship to recognize what an answer leaves out.

At home in New York, he and his wife are raising three boys. He wants more time with family and more encounters in person after years spent working largely through screens. His children’s eventual working lives give the apprenticeship question a personal future.

The young analyst wanted his preparation to carry him forward. The founder still values preparation, but his account now has room for speaking, testing, noticing and meeting people whose experience differs from his own. On weekends, there is a particularly concrete way to keep doing that. He goes to the gym, joins the game and finds out who is there.