Zach Simmons has spent a fair amount of his working life trying to make an expensive mistake less likely. The mistake is familiar: build something, polish it, announce it, and discover that the intended customer has other plans. There is something almost touching about the amount of confidence a business can accumulate before asking a stranger a question. Simmons made the asking into a business.
In 2012, he founded Discuss.io, the company now called Discuss. Its proposition was plain enough to explain without a conference badge: use video and online recruitment to get businesses talking to people who might buy their products. A conversation that once required a physical research facility could happen through a laptop. The consumer could stay put. So could the researcher. Geography would have to find another way to make itself expensive.
By January 2026, Simmons was announcing a different sort of transaction. He had acquired a strategic interest in Appraiva, a property-data business using computer vision, and become its board chair. This time, other founders had already built the product and attracted customers. He was buying into evidence that a market existed.
Read together, those two ventures suggest a consistent preoccupation. How do you get closer to a real customer before committing more time and money? At Discuss, he helped make the interview easier. At Appraiva, he chose a company that had already passed some of the tests. The route changed. The question survived.
A webcam, a transcript, a shorter wait
Before Discuss, Simmons worked in technical product management at Amazon Web Services. His background included responsibility for S3, Amazon’s cloud-storage platform. He also earned an MBA at the University of Chicago Booth School of Business, which he attended from 2006 to 2008. That combination placed him at an intersection of software delivery and commercial decision-making. A beautifully functioning product still needed somebody willing to pay for it.
Discuss paired his software experience with co-founder Jim Longo’s market-research background. Longo had worked at Harris Interactive and Itracks. Their respective histories mattered because an interview platform has two jobs: the call must work, and the research must be worth conducting. Getting people onto the same screen is only the visible part of arranging a useful conversation.
The early service bundled online interviews and focus groups with participant recruitment. Its recordings were synchronized to searchable transcripts, so a useful remark could be located and turned into a clip. That small detail says much about the product. A customer’s answer has a second journey after the interview ends: somebody inside the business must find it, share it, and persuade colleagues to pay attention.
In his early public description of Discuss, Simmons emphasized access from an ordinary laptop and internet connection. The ambition was to shorten research from months to days. For a product team, timing changes the value of an answer. Feedback arriving while a concept can still be revised has a different use from feedback delivered after the packaging has been printed.
- 01Find peopleOnline participant recruitment
- 02Have the conversationVideo interviews & focus groups
- 03Keep the evidenceSearchable transcripts & clips
The customers arrived before the cheque
The company’s early finances provided their own test of demand. Simmons described nearly two years of bootstrapping before investors took notice. He connected that restraint to bargaining power: a business already bringing in money could negotiate from a different position. It is an unromantic origin story, which is part of its appeal. Revenue does not require a flattering camera angle.
He was equally unsentimental about preparation. Big-company experience and formal education, he observed, did little to prepare a founder for running short of cash. Discuss required product choices and personal sacrifices. His stated achievement in April 2015 was a global rollout at Unilever. His next ambition was to quadruple revenue within twelve months. That was a target, rather than an outcome to be assumed.
By May 2017, Discuss had raised a $5 million Series A led by Unilever Ventures with Pereg Ventures participating. Total funding then stood at $6.35 million. The customer list included Unilever, PepsiCo, Nestlé, Danone and Godrej. There was a pleasing commercial symmetry in having the investment arm of a customer back a company devoted to understanding customers.
The organization was already distributed. Of 37 employees, 14 worked from Seattle’s Fremont neighborhood. Engineering also operated in Poland; salespeople were spread across the United States and Europe, with operations staff around the world. A company selling conversations across distance had acquired some practice of its own.
Confidence, with room for correction
Simmons’s answer to a question about his most valuable founder lesson was brief: “Being simultaneously confident and humble.” It is an awkward combination to schedule into a meeting. Confidence gets the product built. Humility lets a customer tell you that the button is in the wrong place, the offer makes little sense, or the entire premise needs another look.
There is outside testimony to that combination. When Shalendra Chhabra joined Discuss as vice president of product in 2016, he described having watched Simmons turn an idea into a profitable business over four years. Chhabra singled out focus and humility. Simmons, in turn, described Chhabra as a longtime friend and adviser, and pointed to his product and marketing experience. The relationship preceded the appointment.
Simmons also wrote about the stubborn practicalities of adopting research software. His 2017 industry commentary argued for simpler tools and less friction, using technologies that people already had: browsers, webcams, streaming and searchable language. The emphasis was on making research easier to carry out. An innovation that demands an elaborate lesson before its first use brings its own little tax.
His later commentary kept returning to the same issue. Research buyers cared about useful insights, speed and price. The mere presence of technology did not settle those questions. That distinction gives his career a more specific shape than a general enthusiasm for software. He was interested in established work where the process could be improved enough for people to change their habits.
“Being simultaneously confident and humble.”
Zach Simmons, on his founder lesson, 2015
A growth chart with a date on it
Discuss’s expansion eventually appeared in the rankings that companies like to frame. The 2019 Deloitte Technology Fast 500 placed it at number 124, with revenue growth of 1,013 percent over Deloitte’s measurement period. Simmons was named as CEO. Startup Weekly also recorded an Inc. 5000 placement of 296 and three-year growth of 1,509 percent. Those are company results achieved during his leadership, rather than personal financial disclosures.
The distinctions are useful when they retain their dates and definitions. A growth ranking records a particular interval. It cannot explain every hiring decision, customer renewal or product revision that produced it. Here, it supplies a check on the scale of what happened: the business that began by reducing the coordination surrounding interviews had become a substantial operation with recognizable global customers.
Simmons is now a former CEO of Discuss. In a later farewell, successor Simon Glass thanked him among the company’s board members. The succession is part of the story because a founder’s work can continue after somebody else takes the chief executive’s chair. The business retains the original problem while accumulating decisions, people and responsibilities that extend beyond its first author.
2019 rank
Deloitte measurement period
The next bet came with customers
Appraiva brought Simmons into a different workflow. Real-estate investors looking for properties have traditionally spent time driving through neighborhoods to inspect exteriors and identify possible opportunities. Appraiva applies computer vision to street-level imagery to produce property-condition information. Its attraction is easy to grasp: software can help narrow where a person should look next.
In announcing his investment, Simmons credited Arman Iranpour, Matt Aleali and their colleagues for building the product and establishing demand. He described his own priorities as product innovation and a more assertive approach to reaching the market. Aleali’s announcement welcomed him to the board and reported more than 750 customers and seven-figure annual revenue. Those figures described the business at that announcement, rather than a forecast.
The existing team remained important to the transaction. Keeping its knowledge inside the company was part of the transaction’s logic. Buying software does not automatically transfer the reasons behind every decision. Retaining the people who have lived with a customer problem preserves a kind of working memory that no handover document can fully contain.
Simmons’s public discussion with Andrew Gazdecki framed acquisition as a choice about risk. A business with paying customers gives its new owner more information than a fresh idea does. There is still work ahead: serving those customers, improving the product, finding the next market. His argument was that operating experience could be brought to bear on a business whose initial demand was already visible.
That makes Appraiva a fitting next chapter for the co-founder of Discuss. Years earlier, he helped companies hear from customers before making a decision. Now he was making a decision around customers already won by somebody else. The evidence arrived in a different form: subscriptions, a functioning product and a team prepared to continue.
His stated ambitions remain practical. Deepen the existing business. Improve the product. Explore where else its data can be useful. There is no need to turn those intentions into a prediction. What connects the two companies is already interesting enough: Simmons keeps looking for ways to make the next commitment with a little more information. The glamorous part may be the announcement. His career keeps returning to the question that ought to come before it.