Alex De Simone was in a Stanford business-school dorm room, trying to arrange internet service. Comcast had him waiting on the phone. It was an unimpressive setting for a business idea: a customer who wanted to get something done, a company that could help, and an extended interval in which neither appeared to be accomplishing much.
His response was to imagine a different route. If a call went unanswered, could the conversation continue by text? The prototype had an appropriately hopeful name, Caller Zen. There are few ambitions more reasonable than bringing a little serenity to a phone call. There are also few places where serenity is so enthusiastically tested.
That question grew into Avochato, the business messaging company De Simone co-founded and leads. Its first customer, Pet Box, used the service to tell people their pet gift boxes were on their way. An internet-service irritation had produced a practical way to announce the arrival of treats. The earliest use case had rather more charm than the original problem.
The appeal of this story is its scale. A text about a delivery is a small event. For the person waiting, it can be the missing piece of information that lets the rest of the day proceed. De Simone has spent years building around that gap between a business having something to say and a customer being able to hear it.
An engineer learns to ship
His education began in mechanical engineering: a bachelor’s degree at Johns Hopkins, followed by a master’s at Stanford. He worked at Accenture and then Moovweb before founding companies. The sequence matters because it puts consulting, engineering and software development in the same working life. Each offers a different view of a problem: how an organization behaves, how a mechanism works, and how an idea reaches a user.
At Accenture, exposure to growing software businesses prompted him to learn programming on his own. Moovweb gave him a chance as a developer. Within a week, he and two teammates were building a mobile commerce site for Men’s Wearhouse. A month later it was finished. Millions of people used it.
There is a particular satisfaction in that sequence: make something, release it, watch strangers use it. A drawing can be elegant and a proposal persuasive, but a working product invites an answer from the world. For a novice developer, shipping a site that people actually visited was a fairly direct form of encouragement.
It also placed De Simone in a company founded by Stanford MBA alumnus Ajay Kapur. Several colleagues had attended the business school. The path toward his next degree emerged through people he already worked with, rather than through a sudden revelation about what a founder ought to study.
A swipe, a degree, two company milestones
Jobr, his first startup, applied the familiar swipe gesture to job discovery. A user could accept or dismiss a position with a movement of the thumb. The company also supplied recruiter tools. De Simone was a co-founder; TJ Nahigian was its chief executive when Monster announced the acquisition in June 2016.
The design borrowed a behavior people already understood. That is an interesting precursor to Avochato: the interface asks less of the user. Finding a job is consequential enough without making every exploratory interaction feel like an administrative assignment. A swipe makes the first decision quick, leaving the larger decision for later.
Monster’s plans went beyond purchasing an app. It intended to integrate Jobr into its recruitment platform, beginning with account access and membership workflows, and use the team to expand its mobile capabilities. The buyer saw both a product and a group of people who knew how to build for the phone.
De Simone had chosen to attend Stanford GSB while continuing to support Jobr. “I decided that I couldn’t pass up Stanford GSB,” he said. He developed Avochato during the summer between MBA years. Graduation brought a remarkable coincidence: Jobr was acquired, and Avochato received its first funding.
He had also pledged 2.016% of his equity in both companies to the school, honoring the Class of 2016. The Jobr sale made his the first such equity pledge to pay out. A class-year joke, carried to three decimal places, had become a real contribution. It is an unusually tidy meeting of sentiment and arithmetic.
The equity share De Simone pledged in each of his two companies to Stanford GSB.
The demonstration was already a conversation
Avochato’s early work concentrated on the product. De Simone, co-founder Christopher Neale and founding engineer Ted Hanson focused on reliability and functionality. As usage grew, they added a dedicated sales effort. Ryan Axt, previously at Salesforce, joined to lead it.
His initial target was $500,000 in annual recurring revenue within twelve months. He reached it in six. The company reached $1.5 million in annual recurring revenue during his first year, with a team of four. These are early company milestones, snapshots of a particular stage rather than a description of today’s business.
The demonstration was built into the sales process. A prospective customer could send Avochato a text, receive a reply from the team, ask questions and continue with a call. After becoming a customer, that person could use the same number for support. Calls and messages were logged together.
“We are truly living proof that the product works,” De Simone said. It is a useful claim because it can be tested in the interaction itself. If a business sells a quicker way to communicate, the conversation with that business becomes part of the evidence. A sluggish reply would be an awkward brochure.
The arrangement also makes the handoff important. Sales and support often describe the same customer in different language. A shared history can spare that customer the small indignity of beginning again. The value lies in keeping the thread, including the unglamorous details that explain why someone got in touch in the first place.
Avochato’s documented early sales and support workflow.
Five people, seven figures, then a bigger table
In December 2018, De Simone announced a $5 million Series A. Amity Ventures led the round. His update described a five-person team reaching seven-figure revenue in less than a year and acquiring hundreds of customers with Avochato’s own platform. The funds would support sales growth and further development of the messaging product.
“Customers are in the driver’s seat,” he wrote. It is a compact statement of a fairly demanding operating rule. The customer chooses when to reach out and brings an expectation shaped by other conversations. A business then has to organize its people and software so that answering feels straightforward.
Funding introduces another kind of coordination. The customer may still see one message bubble, while the company behind it acquires more employees, more functions and more decisions to make. The little exchange on the screen remains little. The machinery supporting it becomes more involved.
Former Yelp engineering executive Michael Stoppelman, already an early investor, subsequently joined Avochato’s board. De Simone welcomed his experience building engineering organizations. The announcement described plans to expand the engineering team and accelerate the product roadmap. A company built around conversation was assembling people who could help it handle more of them.
Avochato’s own founders’ collage supplies a lighter view of the machinery: De Simone holding avocado props, fellow founders in the surrounding photographs, and a dog getting a generous share of the frame. Enterprise software can tolerate a little visual absurdity. The customer’s problem will still be there after everyone has put down the oversized toast.
The reply needs somewhere to go
By 2021, De Simone was writing publicly about messaging trends. His advice included one-to-one conversations, combining communication channels, and connecting messages with customer-management systems. He argued for choosing the combination that suits a business and its customers, rather than adding channels indiscriminately.
That is an important detail in a messaging founder’s thinking. A text is useful when it reaches the right person and fits the task. A call can be useful too. A customer may begin with website chat and continue elsewhere. The operational question is how to preserve enough context that each transition moves the conversation forward.
His product updates have kept returning to that question. On LinkedIn, he described an Avochato Chrome extension intended to reduce tab switching, mobile calling features, and a Zapier integration that lets AI tools take actions such as sending a message or updating a contact. The work extends the product into places where customers and teams are already operating.
The about page now describes more than 1,000 customers and millions of two-way conversations. “Two-way” does a lot of work here. Sending a notification is only the beginning of a possible exchange. Someone may answer with a question, a correction or an entirely different need. The business has to be ready for the reply.
“Customers are in the driver’s seat.”
Alex De Simone · December 2018
A cloud bill sends him back to the hardware
In October 2026, De Simone described another irritation to his friend Alex Oppenheimer on the Very True podcast. Avochato’s OpenSearch workload had risen from roughly 20% to 60% of its AWS bill. He and a founding engineer reconsidered the setup, acquired their own hardware and moved that workload to a data center in Santa Clara.
He reported about half the bill and substantially greater compute potential. The move concerned a particular workload; its interest lies in the willingness to reopen an established decision. A service that made sense at one stage deserved another look when the economics changed.
The connection to the dorm-room idea is hard to miss. In both cases, the useful question begins with a routine frustration. Why does this process work this way? What would an alternative require? The answer may be a text message. It may be a server rack. Neither earns its place by sounding fashionable.
There is something appealing about a mechanical engineer coming back around to physical machines after years of software. The customer still gets a conversation on a phone. Somewhere behind it, choices about equipment, costs and maintenance determine whether that conversation is practical to provide. Convenience at one end rests on attention at the other.
De Simone’s stated ambition is to build a sustainable, profitable, long-term business that delivers value to the people involved. The word “long-term” puts ordinary decisions under a different light. A company has to keep asking what helps its customers, what it can afford to deliver, and which assumptions have grown stale.
Caller Zen was a cheerful name for escaping a wait. Avochato has become a longer exercise in the same habit: find the delay, understand the mechanism, and give the person on the other end a way to get on with the day.