Adam Jackson and the price of getting people together

Adam Jackson’s first improvement to his working life was a roof. As a boy in northern Ohio, he cut grass, laid mulch and shoveled snow. By fourteen, he wanted a job indoors. A computer store offered an escape from the weather, provided he was prepared to clean toilets and take out the rubbish. He was. The shop also taught him to assemble PCs. Eventually, he ran a custom computer business while still in high school. Before he had a theory about marketplaces, he had learned to put useful things together.

That is a pleasingly literal beginning for a software entrepreneur. A computer either works or it does not, and a missing component is indifferent to your enthusiasm. Jackson would go on to study at Vanderbilt, build companies in San Francisco, become an investor and spend years arguing about the economics of connecting strangers. His career has accumulated different products and business partners. The underlying problem has remained remarkably familiar: somebody needs something, somebody else can provide it, and the introduction is harder than it ought to be.

An internet business with a pavement problem

Jackson studied computer science at Vanderbilt University, attending from 1998 to 2002. His early venture-backed business, MarketSquare, began in 2004. It helped physical shops put their products in front of people searching online. The distinction mattered. A local retailer could have exactly what a shopper wanted and still be effectively invisible to that shopper’s browser. Software offered a way to make the shop discoverable without requiring the customer to walk past its window.

This was a marketplace built around proximity. The internet was good at making distance disappear; MarketSquare’s usefulness depended on showing what was nearby. Jackson later described joining Intuit’s QuickBooks product team after the acquisition. The sale came in 2006. His progression from writing software to developing a product inside a larger company gave the young founder two views of the same work: getting an idea moving, then fitting it into an organization with an existing audience.

DriverSide followed in 2007, founded with Trevor Traina and Jad Dunning. Its subject was the long relationship between a person and a car. Buying the vehicle was only the opening scene. Service, maintenance, parts and eventual resale supplied plenty of sequels, some of them expensive. DriverSide gathered advice, owner discussions and reviews of mechanics and dealers around those recurring needs. There was editorial work alongside the software. A useful answer could matter as much as a clever matching algorithm.

Advance Auto Parts acquired DriverSide in 2011. Across the two businesses, Jackson had worked on making information useful at the moment someone needed to act. A nearby shop, a mechanic, a relevant piece of advice: each was more valuable when it reached the right person. A marketplace could earn its place by making the search shorter. The next question, increasingly prominent in his career, was how much of the resulting transaction the marketplace should keep.

Knowing which part of the job is yours

In 2012, Jackson co-founded Doctor On Demand with Phil McGraw and Jay McGraw and became its founding CEO. He held the operating role until 2016. The unlikely-looking partnership had an introduction behind it: Jackson has credited Nextdoor co-founders Nirav Tolia and Sarah Leary, together with Fenwick & West lawyer Cynthia Clarfield Hess, with helping connect him to the McGraws. A founder’s network can sound abstract on a biography. Here it had names and an identifiable consequence.

The partnership brought people from software and television into the same company. Jackson’s subsequent departure from the CEO role is a useful part of the story. Founding a business and running each later version of it require different appetites. Four years is long enough for a company’s daily work to change substantially. His career moved on to investing and another startup, while Doctor On Demand remained part of the record of what he had helped establish.

He also backed other founders. His disclosed investments have included Rapportive, Automatic, Superhuman and the Long-Term Stock Exchange. Those connections put him on both sides of the funding conversation: the entrepreneur assembling a company and the investor deciding which other companies deserve a chance. That experience would become relevant when he began proposing an ownership model that gave a network’s users a larger role in its direction.

The investor starts questioning the machinery

By 2017, Jackson was chief technology officer and a managing partner at Cambrian Asset Management, working with Martin Green and Jay Posner. Cambrian approached digital assets through a systematic, rules-based investment strategy. Jackson described the technology in terms of ownership, identity and contracts moving across the internet. His interest extended beyond a new instrument to trade. The engineer was thinking about what a programmable ownership system might let a group of people do together.

The question was relevant to businesses he already understood. A marketplace needs enough buyers and sellers to become useful. Attracting them can require substantial outside funding. Investors then expect a return, and transaction fees offer a straightforward way to produce one. Jackson’s objection concerned what happened when those fees became a reason for the people doing the work to leave. A business could make its own service less attractive by charging more for the connection it had created.

Braintrust, co-founded with Gabe Luna-Ostaseski in 2018, became his attempt to arrange those incentives differently. The network connected organizations with independent technical and design talent. Its early proposition included a zero fee on the talent side and participation in governance through the BTRST token. Contributors could help develop the network, bring in participants or assist with its operation. The people using the marketplace were also being invited to help build it.

“Talent is spread evenly across the world. Opportunity is not.”

Adam Jackson, 2020

In 2021, Jackson explained the model with an engineer’s hourly rate: talent could state a rate and keep it, while the client paid the network fee. The appeal was understandable without a blockchain vocabulary lesson. If the connection creates value, preserving a useful share for the people involved gives them a reason to return. Governance added another question: who gets a say when the rules change? His argument tied the price of participation to the power to influence it.

Then the customers stopped hiring

A marketplace’s design does not exempt it from the economy. In a 2023 network update, Jackson said roughly three-quarters of Braintrust’s enterprise clients were on hiring freezes, up from about half several weeks earlier. That is an awkward development for a talent business. His response was to focus on costs, existing customers and automation, while continuing to build the talent side of the network. A crowded pool of capable people cannot create a hiring budget by itself.

His interest in automation was becoming hands-on. Jackson described examining manual processes across the network and looking for ways to automate them. Braintrust invited its community to propose AI projects, with token rewards and the possibility of paid implementation. A June 2023 showcase included Jackson and Luna-Ostaseski announcing the competition winners. The ownership experiment now supplied a practical way to solicit improvements from the same people who used the product.

Braintrust AIR followed in 2024. Jackson presented it as a way to reduce the repetitive work surrounding recruitment: producing job descriptions, finding matches and screening applicants. His stated ambition was to leave recruiters more time for the human work of developing talent and building a company’s culture. The product brought him back to an old concern in a new form. This time the delay between two people included calendars, applications and the repeated first conversation.

He tried the AI interviewer himself. The experience, he said, felt “totally surreal.” It is a small reversal worth keeping: the founder who had spent years assessing products and people became the interview subject of his own software. In the same period, he described reading three or four books a month and being involved throughout AIR’s development, from concept to market launch. Selling the resulting product, he said, was then his principal responsibility.

A conversation still needs another person

By January 2026, Jackson was writing about the distinction between conversational voice interviews and recorded video submissions. AIR’s primary format was now described as an adaptive voice conversation, with follow-up questions shaped by a candidate’s answers. A human reviewer would receive scores and supporting evidence and decide who advanced. The product description had become more specific about where the software sat in the process and where the recruiter’s decision began.

That division of labor is the interesting part of Jackson’s current work. Software can make an introduction quicker and organize information for a decision. The people on either side still have to decide whether they want to work together. His public argument for automation gives recruiters room for judgment rather than treating every hour of their work as interchangeable. The recurring commercial challenge is to make that promise useful to the person hiring and tolerable to the person being assessed.

The other business runs on vineyard time

There is another Jackson enterprise in Coombsville, in the southeastern part of Napa Valley. In 2020, he acquired the property associated with Asymmetric Vineyards, which he runs with fellow proprietor Brent Walker. They focus on estate-grown Cabernet Sauvignon from a single vineyard. The setting introduces a different schedule to a career full of software releases. Vines offer no persuasive response to a request to bring the next quarter forward.

The local vintners’ account of Asymmetric supplies an agreeable detail: Jackson loves wine, technology and investing, and is awful at golf. It also describes an early idea for connecting bottle buyers through QR codes, with optional NFT membership. Even away from recruiting, the invitation to form a network had followed him. Walker, who comes from custom residential construction, brings another builder’s background to the partnership. One business starts with a database; this one starts with a place.

Jackson’s public biography includes a four-in-the-morning routine, strong coffee and loyalty to the San Francisco 49ers. These are familiar enough founder accessories. More revealing is the range of clocks he has chosen to live with: an applicant waiting for a reply, a customer waiting for a match, a vineyard waiting for its fruit. His work repeatedly asks which delays can be removed. The wine business provides a rather pleasant reminder that some things still take their time.