
Written by a model from the transcript; not yet reviewed.
In this episode, A16Z general partner Alex Rampell sits down with Town founder and CEO Jean Denis Grez to discuss what it takes to make AI genuinely useful at work. Jean Denis shares why he walked away from a growing tax software business after one year to build Town, an AI assistant that integrates across email, calendars, and everyday workflows. They analyze why AI adoption remains uneven, how agents are changing commerce and software, and why businesses may want independent AI assistants that are not tied to a single model provider.
Jean Denis recounts leaving Plaid, building an SMB tax tool, and ultimately pivoting to create Town.
The founders discuss why tax automation, despite technical feasibility, struggled to achieve venture-scale growth due to market dynamics and timing.
After realizing tax automation’s limits, the team pivots to building an AI assistant that works across email, calendar, and business workflows.
Town quickly gains product‑market fit, with users driving continuous improvement and the team scaling the product from beta to launch.
The founders explain their strategy of starting with product‑led growth in SMBs and later expanding into enterprise through a scalable approach.
The discussion turns to how Town positions itself against large AI labs, emphasizing neutrality, data ownership, and the ability to switch providers.
Marc Andreessen opens the episode with a brief introduction and welcome to listeners.
The hosts explore why tinkering culture drives AI adoption and why many businesses lack the time or talent to experiment.
They argue that AI products must go beyond a simple text box to deliver real value and stickiness.
Marc highlights how agent traffic is surpassing human traffic and the implications for advertising and distribution.
The discussion turns to the tension between adversarial and synergistic approaches to AI agents and their impact on business models.
Walking Away From Tax Softwarestory
Jean Denis explains how his team built a successful pre-AI tax prep business with nearly a million in revenue, only to realize incumbents would catch up and tax is not a high-frequency daily tool.
Founders Core Motivations and Failureinsight
Admitting failure feels difficult in the moment, but founder motivation relies on believing the business can have massive impact and justify the team's opportunity cost.
Prioritizing Users Over Enterprise Buyersstrategy
The founders explain why building for the actual user first, as they learned at Dropbox, is vastly superior to starting with rigid enterprise compliance requirements.
Token Allocation and Cheap Prepinsight
Town operates as a token allocation machine where cheap tokens make long-tail tasks like generating daily meeting prep notes economically viable.
The Risks of Competing With Suppliersdebate
The guest discusses the inherent risks of competing with model providers like OpenAI and Anthropic while emphasizing the value of offering model neutrality to mid-market firms.
The Need for Tinkers in AI Adoptioninsight
AI adoption lags outside Silicon Valley not because the intelligence is missing, but because everyday businesses lack tinkerers who know how to prompt solutions to their problems.
Shifting Supply Aggregation in Commerceinsight
The hosts discuss how agent traffic threatens traditional supply aggregators like Amazon because automated purchasing bypasses standard web ads and human browsing behavior.
“We really wanted to build something that mattered and help people.”
“I think the second reason, which is like very important is.”
“We spent a year building that.”
“We were just like, hey, we're getting a ton of pull from users. Let's go after this for a few months really hard, and learn about the market, and see what the opportunity could look like.”
“I think the other strategy that you see in the market, which is I think what the labs do, is a FDE approach.”
“I think for the SMB and make market, I would say, I would agree with you, but the market is, but the, the market for AI doing more for a business and helping the business be more successful is bigger than the coding market.”
“And the, the unlock is, is there someone over there that gets AI enough to want to tinker a solution to their problem?”
“I think that's like the real unlock.”
“The reason why it's not diffusing is because even though in Claude or in ChatGPT, there has existed for the last 12 months, features that at a lot of small businesses, you could use to save you so much more time.”
“The other thing that is interesting to me conceptually are like experiences, like friction that you enjoy as a human, but that friction that you don't.”
Why hasn't AI transformed everyday work as quickly as coding? Town CEO Jean-Denis Greze argues the bottleneck isn't intelligence, but making AI useful to people who don't have the time or technical skills to build their own automations. Jean-Denis joins a16z General Partner Alex Rampell to share why he pivoted Town from tax software to a personal AI assistant built around email, calendars, and the workflows that run businesses. They discuss why consumer-grade experiences may win in enterprise AI, how Town discovers and automates tasks users wouldn't think to delegate, and why model neutrality and data ownership matter as AI labs increasingly compete with application companies. They also explore what happens when agents begin acting on our behalf, from managing everyday work to shopping and commerce, and why the next generation of software may need to adapt to each user rather than the other way around.
12,833 words · 3 speakers
Speaker names marked are inferred from speaking time and the show’s known hosts — they are not voice-verified.
Page updated · transcript and summary are machine-generated