David Walker and the trouble with a good idea

David Walker had an elegant answer to a familiar New York irritation. If real estate agents earned salaries, perhaps they would concentrate on finding clients the right home, with less pressure to rush a commission. It was an attractive proposition for anyone who had ever emerged from an apartment viewing wondering whose interests had just been served.

Triplemint tried it. The arithmetic became awkward. Strong agents earned too little, weaker performers earned too much, and recruiting the people who might improve the customer experience became harder. Walker’s retrospective verdict was refreshingly short: “In practice, it was a disaster.” A compensation plan meant to remove friction had manufactured some of its own.

The founders began asking buyers about their experiences. Conversations at a holiday party, discussions with investors, support calls and formal interviews supplied a less elegant, more useful answer. Customers wanted a good deal and a straightforward purchase. The brokerage’s payroll arrangements were a distant concern. Triplemint changed to a commission structure.

This is a useful place to meet Walker, co-founder and former CEO of Triplemint, now co-founder and CEO of Spara. His career includes a national rowing championship, a brokerage acquisition and another venture-backed company. But the salary experiment offers something the milestones leave out: a founder describing how his own reasoning let him down.

Before the pitch deck, a paintbrush

Walker’s early working life had two rather different settings: property development projects and places to sell his art. He spent summers on construction crews and in leasing offices. He also sold oil paintings and photographs. The person who would eventually build software for property transactions had already encountered buildings as both practical workplaces and visual subjects.

At Yale, he studied political science, with an interruption that turned out to matter. During the 2009-10 academic year, he stepped away from school and rowing to work at YouRenew.com. As director of marketing at the electronics recycling startup, he worked on its brand, marketing and business development. He returned to finish his degree.

The detour gave him operating experience before he had completed the academic qualification. It also complicates the tidy version of a university founder’s biography. There was a period of working inside somebody else’s young company, seeing the commercial tasks that sit behind the word entrepreneurship. A brand needed explaining. A business needed customers.

His rowing teammate Philip Lang became his business partner. They began the venture that became Triplemint under the name Suitey in 2011, while Walker was still finishing Yale. The early business focused on rentals, and both founders worked as agents. They were learning the apartment business by doing the part that customers actually encountered.

Twenty-two thousandths of a second

On June 4, 2011, another team Walker belonged to reached a finish line with considerably less room for interpretation. Yale’s varsity lightweight eight crossed ahead of Harvard at the IRA national championship in Camden, New Jersey. The official times were 5:39.904 and 5:39.926. Walker rowed in the six-seat.

Neither crew immediately celebrated. Officials consulted video before declaring Yale the winner. A margin of 0.022 seconds is enough to settle a championship and barely enough to say the word boat. For Walker, the return from his year away had brought a national title. He went on to captain Yale’s lightweight team in 2011-12.

The result supplies a pleasingly exact counterpoint to startup language. A boat has a finish line; a business keeps discovering that the course has changed. Walker’s two pursuits overlapped in time, but the commercial work would require a different relationship with certainty. A payroll model could sound sensible and still need throwing overboard.

The expensive pleasure of building it yourself

Triplemint developed tools to help agents reach buyers and sellers, including people whose homes had not yet come onto the market. By February 2017, it had raised a $4.5 million Series A, bringing reported funding to $7 million. Its agent count had doubled to 55 during the preceding year. The company was attracting money and people around its promise of a better property transaction.

Some of the engineering effort went inward. The founders wanted a customer relationship management system that fitted their own workflow, so they built one. Walker later described the product as better suited to their requirements than available alternatives. That made the decision harder to abandon. The thing worked; it was consuming attention the company needed elsewhere.

Maintenance drew engineers away from the customer-facing product. External deadlines slipped because internal software needed work. Eventually Triplemint scrapped its own system and adopted Salesforce. The replacement involved compromises, but it released resources. An internal tool could be technically pleasing while leaving the overall business worse off.

Taken together, the salary plan and the home-built CRM reveal a particular kind of founder’s mistake. Both began with dissatisfaction and a plausible improvement. Both created costs outside the initial frame of the decision. Walker’s willingness to describe them gives his later advice some texture: he has examples in which changing his mind required giving up work he had already done.

A weekly appointment with the small wins

There was a quieter system at Triplemint that required much less engineering. Employees could submit positive shout-outs about colleagues. At the weekly all-hands meeting, Walker read the kudos aloud. Help that might otherwise disappear into an ordinary working week became something the whole company heard about. Recognition had a recurring slot on the calendar.

He also met new hires early for a conversation about mission, vision and culture, and asked employees for their views through surveys. In a 2018 discussion of those habits, he said, “I try to listen more than I talk.” His account put responsibility on the CEO to set an example while leaving room for ideas from elsewhere in the company.

Hiring occupied plenty of his attention. In his writing for Inc., he described close to a thousand interviews conducted by him and his co-founder. His suggested questions explored previous bosses, workplace conflict and expectations about feedback. Those are revealing interests for a founder: how somebody handles disagreement may tell you more about working together than a polished account of personal ambition.

His published advice also acknowledged the uncomfortable link between confidence in a company and confidence in oneself as its leader. That distinction matters when a decision needs reversing. If every product choice becomes a referendum on the founder, admitting an error becomes considerably more expensive. The practical task is to keep learning without making colleagues pay for one’s pride.

“I try to listen more than I talk.”

David Walker · 2018

The company changes its name. The work travels.

The milestones accumulated. Triplemint placed No. 325 on the 2017 Inc. 5000, and Walker appeared on the 2018 Forbes 30 Under 30 list in consumer technology. Then, in May 2022, The Agency announced its acquisition of Triplemint in an all-equity transaction. Walker became chief strategic officer; Lang became chief business officer.

The pairing exchanged complementary assets. Triplemint brought technology to a brokerage with an international brand and network. Its people joined The Agency, and the businesses would operate under the Agency name. A separately announced $35 million growth-capital round accompanied the transaction. By September, Triplemint was formally The Agency New York.

For Walker, the acquisition carried his work into a larger organization. It also put the customer-experience problem at a different scale. Helping agents work effectively had always involved the machinery around them: finding opportunities, handling information, and making sure an interested person reached someone who could help. Those concerns would survive the change of sign above the door.

The next customer is already waiting

With Spara, Walker returned to a problem he had encountered while running sales operations: a buyer arrives interested, and the company makes that buyer wait. A form collects the details. A reply comes later. A meeting takes longer still. Each step may be convenient for the seller’s organization while being thoroughly inconvenient for the person hoping to buy.

He co-founded the company with Zander Pease. Spara publicly launched in September 2025 with $15 million in seed funding, led by Radical Ventures and Inspired Capital. Its software engages prospective customers through chat, email and voice, using a company’s information and sales rules to answer questions, qualify interest and arrange the next conversation.

The initials stand for Sales Performance And Revenue Acceleration, which is a substantial amount of corporate ambition to squeeze into five letters. Walker’s explanation is more approachable. Interested people should be able to ask useful questions and receive useful answers while they are still interested. Sales representatives should arrive at subsequent conversations with a better understanding of what those people need.

He remains interested in how other operators solve those problems. In October 2026, he published a conversation with Clay’s Nancy Mottice about building its partner business. The questions now concern selling software rather than finding an apartment, but the attention to the working details is familiar.

The salary experiment remains a useful companion to this new venture. Buyers had their own priorities, and a persuasive internal theory could obscure them. Walker has already had to learn that lesson at the payroll level and again in the engineering budget. At Spara, he is making another proposal about how buying should work. The people on the other side of the conversation will get their say.