Previously Talisman AI
NEWS

Redefining Legal AI from Brazil: Lessons from Enter’s First Two Years

[
September 23, 2025
]
Mateus Costa-Ribeiro

Co-founder
Chief Executive Officer

September 24, 2025

Today marks Enter’s second birthday. We chose this special date to announce the largest investment commitment by a Brazilian AI-native company: we have raised $35 million from Founders Fund and Sequoia to continue transforming Brazil’s legal system at its core.

The two years that followed felt like driving a car at full speed, where success means flying full throttle past a curve with your heart in your mouth, just to see an upcoming turn right in front of you. Before you have time to take a breath, it’s time to step on the gas again.

The challenges we had to overcome were so tremendous that only a relentless, impatient exercise of force allowed us to stand out from the crowd. Since we announced our Seed round five months ago, Enter has only accelerated and:

  1. Added eight enterprises to our customer list, all of them publicly traded, including Mercado Libre, Airbnb, Santander, Itaú, Banco Mercantil and Magalu;
  2. Crossed 250,000 lawsuits managed by our AI platform (about 2x the total number of civil lawsuits filed in Japan in a year); and
  3. Increased our average share of cases (the number of lawsuits handled by Enter) within customers by over 4x – a retention indicator of our success in extrapolating pilots and experiments and joining the long-term strategy of our customers to reduce legal costs.

Building a company has brought me both fulfillment and heartbreak. Often at once. Enter has allowed me to find for the first time what I truly love doing and showed me what pursuing a life mission feels like. That was the greatest gift from my founder journey: feeling an excited obsession to go to work. It also took away from me some of the things and people I loved the most: from dropping out of Stanford and letting go of a lifelong dream of living in the Valley to struggling to make time for the people I most care about in the world and suffering from watching them distance themselves.

The past two years boil down to two phases: survival and scale. In Phase One, we had to build a product that people acutely needed – and we had to do it fast; in Phase Two, we are right now building a religion to rally the best doers in the world around our shared vision of transforming Enter into Latin America’s largest AI company.

Phase One – Survival

In early May 2024, nine months into our founding, we still had not signed any paying enterprise. We had a little over a million dollars in the bank from our pre-seed and a handful of paying law firm customers. I remember going home on a Monday at 4am after spending the weekend in the office. I had to get some rest before a 9am meeting with what would become the first customer of our lawsuit answers product – a large Brazilian bank. The product still felt glitchy and we were about to launch it for 200 cases. It had to work out or we would lose our best shot at landing our first enterprise logo.

My anxiety coming back from the office that day made me keep biting my teeth so hard I thought I could have broken them.

Exactly a week before, I had pitched a PowerPoint to that bank's legal director explaining the concept of how AI would draft lawsuit answers in three steps: understanding a complaint, reviewing a huge evidence set and outputting a Word file ready for human revision. The client engaged and, most importantly, complained about very specific issues on answers drafted without AI – a job they spent millions of dollars to hire for.

There was a problem and there was money being spent – so I knew I was on to something. 

I came back to the Enter office that day, got the whole team together (we were seven) and said we had to ship the Answers product in a week's time so that large bank could try it out. In Phase One, everything is about finding a product people acutely need – and building it fast.

“Fast” because a startup is like a rocket ship trying to take off: the gravity pull keeping you from reaching orbit is so tremendous that only a relentless and impatient exercise of force (yes, I love this phrase) can break the inertia. A startup’s energy source isn’t fuel – it’s people, and their motivation disbands after 2–3 years if an early stage is not going places. You need to reach orbit fast to escape gravity and keep your troops rallied for the next challenge. There is a limited timeframe to do it. 

That’s why Mike, Vaz, Banduk and I cancelled everything else and worked the next seven days non-stop to meet the deadline we had agreed with our customer. A week later at 4am on a Monday, the day the launch was supposed to happen, we shipped the lawsuit answers product.

Apart from doing things “Fast”, the other priority for an early stage is building a product people “acutely need”. It’s a less fancy word for product market fit (PMF). In our first year of existence, I was obsessed with whether our clients’ lives had changed because of our work, especially because the AI hype led customers to test any agent tool that looked promising. 

I built a framework to measure if the Enter product (or any enterprise product) is “acutely needed”. If you don’t meet these three conditions, you might as well pivot or shut down your company because it won’t reach exponential growth:

  1. Meaningful Budget Commitment – Every CEO is hearing from their board that they should be using more AI tools, and the C-Suite is hearing that from their CEO. Landing a big logo at Enter was therefore not interpreted as PMF, because our product may have been chosen just to check a box or help some director look innovative. We had to earn customers’ trust and see them pay up in order to prove PMF. “Experiments” and “pilots” were the two words I heard the most during Phase One and became the ones I hated the most as a founder (still do!), because they meant small and short-term commitments to our AI product – and meant that it was not yet “acutely needed”. We relentlessly pushed back from pilots during Phase One and went on to persuade several customers to commit to Enter 20–30% of their budget for technology and services providers in the litigation space.
  1. Product Repeatability – Serving large enterprises ($10B+ market cap) will inevitably require a high-touch relationship with decision makers and last-mile customizations because every client has unique internal systems and legal problems. Repeatability means though that your value proposition to clients is specific and consistent across the board. It should delimit a clear target domain (consumer litigation), impact (15% reduction of legal losses) and feature (lawsuit answers) – as opposed to pitching something generic such as “we deploy AI agents to automate repetitive tasks”. That will allow you to reap compound interest from enterprise to enterprise and will ensure that the off-the-shelf, purely scalable part of your product is far more significant than its last-mile customization. If you don’t have a specific AI offering, you don’t have a product – all you have is a group of people running after the next client use case. I used some proxies at Enter to measure if scalability did trump our company’s services arm – and I still ask myself these questions: 
    1. Are over 80% of our software engineers focused on developments that all customers will profit from, even if roadmap prioritization is influenced by our largest customers?
    2. Do our Deployment costs represent less than 20% of our gross revenues at a contract’s maturity?
    3. Is our Sales team using virtually the same demo in every intro meeting?
  1. Excess Consumption – In large companies, the budget decision makers are removed from an AI product’s implementation and usage. That’s why filling the two previous conditions and signing a large contract of a services-light product is not sufficient to define PMF in enterprise software, because they indicate only solid support from leaders up the food chain but don’t demonstrate product retention on the ground. That’s why I would observe if our clients’ base did rally behind the product organically and exceeded their contracted usage of the Enter product to roll it out to unexpected segments. The ultimate sign is when a customer renews their annual contract earlier than expected to expand it to more lawsuits.

Phase One was all about fulfilling this framework in real-life – and managing to get there before running out of money or motivation. It ended in November 2024, when we signed our fifth $500K+ ARR contract with a publicly traded enterprise (meaningful budget commitment) selling the same AI-drafted lawsuit answers (product repeatability) and later had NRR numbers grow through the roof (excess consumption).

Phase Two – Scale

If Phase One is surviving, Phase Two is scaling the product that you discovered in Phase One. At Enter we always think of growth in terms of order of magnitude leaps, and I realized I had to completely change my role in the company when we hit $10M dollars in Contracted ARR.

Until that point, I had personally led every single Sales pitch at Enter and was keenly involved with the main product decisions and deployment squads. I felt in control and had my finger on the company’s pulse.

But then I sat down with my co-founders and laid out a plan to get to $100M in ARR. That was a totally different ball game. My intuition on what the product should become or persuasiveness to close a given client wouldn’t get it done – our plan required us to expand to adjacent markets and sign 5 enterprises a quarter, and that’s the sort of thing that only a product and growth machine can deliver. I realized that Enter was headed in a new direction. 

There are two founder archetypes – Plumber Mode, of knowing your company in detail and de-bottlenecking its pipes, and Preacher Mode, of inspiring others to join your mission.

In Phase Two, my natural Plumber Mode would have to be complemented with Preacher Mode: as the company’s founder, my next mission was to build a religion capable of attracting the best people all over the world to our office in Rua Butanta in Sao Paulo to bring Enter’s vision to life. I went on to dedicate about half of my time to recruiting for our most important positions and working hand in hand with our team, to share the Enter bar for what great looks like.

Preacher Mode allowed Enter to form the most talented early stage team ever assembled in Brazilian history. Over half of our team moved from outside Sao Paulo to join our fully in-person company – myself included. We’ve repatriated over 15 people back to Brazil from the US and Europe, from the world’s best universities, driven by the challenge of building Latin America's primary AI company. We’ve created a circle of excellence where people who love doing great work can feel at home.

We were tested when an amazing engineer (2x Brazilian ICPC champion), who had just accepted our offer, got a counteroffer with a 2x bigger salary and a $200K retention bonus; or when a dream deployment leader earned a three-year visa to work at Amazon in the US after graduating from Harvard Business School and had a clear path to living in a developed country for life. We won every one of those talent wars, because we were able to articulate that Enter is more than a job – it’s the opportunity to find purpose in a movement.

Finding our first sixty people was an Avengers Assemble moment, where everyone recommended the best 2–3 people they had already worked with, and we would race after them.

As brilliant people started joining, I went on to understand how religions were structured over the centuries in human civilization, as I wanted to find out how to keep all these people aligned and moving in the same direction. Religions, it turns out, boil down to three big pillars:

Behavioral Prescriptions are codes of conduct that everyone that is part of the religion must embody. In a company, they should reflect a description of how the founders behave in an attempt to scale their work ethic across the company. That’s why the best way to preach your prescriptions to the company is by just showing up and doing great work – people watch you as a founder and follow your style. The second best way is to explicitly name behavioral prescriptions that define dos and don’ts. In Enter’s case, I narrowed our religion to three prescriptions:

  1. Immediate Candor means not holding back your thoughts or sugarcoating your opinion to avoid conflict. Your teammates deserve your honest feedback on the spot — otherwise you don’t have their back. Holding back feedback creates resentment and hurts your team’s performance, so I chose to instill this value across the company by calling out immediately anything that is off – in our group dailies or team all-hands especially, for everyone to see – and doing it directly and kindly so everybody knows it’s expected that you will correct others to make Enter a better company.
  1. Deliver Wow means going above and beyond what the customer expects – and your customer may be a client (for the Sales or Deployment teams) or a candidate (for the People team) or a user blocked by a bug (for the Engineering team). The way you deliver what they need is faster and better than what reasonable expectations would look like. This principle guides us in simple decisions – such as always hosting customer events in the best possible venues such as the Palacio Tangará in Sao Paulo – to big prioritization decisions that released a quarter in advance a feature to spot document tampering by plaintiffs suing our clients, which made a client's legal manager get emotional for finally finding a tool to detect litigation fraudsters that were ripping off her company. Everything that carries the Enter name on it should be either flawless or built blazingly fast.
  1. The Ship is Sinking Mindset is my favorite because it’s a calling for everyone at Enter not to take for granted that we exist. It means impatience and urgency. We should all act like the founding team did when we had to launch the Answers product in a week and landed our first enterprise contract. It’s key to shrug off complacency. Everybody at Enter is forbidden to say that the company is successful or that we’ve made it. That will continue to be the case even after we go public.

Unified World View is what convinces people they should follow the behavioral prescriptions, which are typically uncomfortable. In Christianity, people avoid sinning (behavioral prescription) in order to go to heaven and follow Jesus’ lessons (unified world view), and our team works with insane urgency at Enter (behavioral prescription) because they believe in our core mission of building a global leader in AI from Brazil (unified world view). It's their belief in that grandiose future that allows them to embrace our discomfort zone. Every company must preach a vision of what it wants to achieve, and it must be ambitious in order to attract people that dream big.

Rituals are the primary reason why Enter chose a fully in-person work culture, five days a week, for all teams. Their purpose is to create a company with charisma and magnetism – one that makes people feel at home and part of a competitive Olympic team at the same time.

  1. Feeling at home – We are extremely intentional about planting the seeds for folks from the team to become good friends and over half of my best friends in life work at Enter. The company organizes monthly gatherings of six people in nice restaurants for the entire team, getting people to know each other outside work. Every weekend there is something going on among people from Enter, especially since many of them moved from abroad to Sao Paulo and became each other's support system. We also schedule an individual dinner with everyone who earns stocks in the company and becomes a shareholder, with their family (mother, father and plus one) and the founders, as a process of sharing how much we appreciate their effort but also of demonstrating to their loved ones how their excellence is recognized by the company they work in. It's an initiation ritual that families love. That way the people they will consult when making professional decisions are onboard with the Enter movement.
  1. Joining an Olympic team – We enabled a spirit of excellence without generating in-house competition by creating a “cult of equity”. That happened in two ways: we gave out beautiful, expensive jackets to people in our team as soon as they earned stocks in Enter – a sign of both status and embodiment of our company's movement. We deliberately chose the sharpest people to gain equity first and shared in our all-hands why each person was getting stocks, connecting their work and actions to our behavioral prescriptions. We also host quarterly breakfasts with our stock owners (about a third of the company) to discuss valuation, liquidity and our strategy to conquer our market, where nothing is censored from the conversation. Everybody is heard, and they are briefed on our latest board meeting. The fact that the jackets and the breakfasts are exclusive was key to everyone wanting to join them – and that meant everyone embodied our values in order to get stocks in the company. This ritual reaffirmed how it means the world to be a shareholder of the company and has led people to work extra hard to get there. 

I went from credential to credential before starting Enter – always looking for the next big academic box to check – and that relied entirely on my own cognitive and communications skills. And so I went on to become the youngest person to do this, to do that.

Yet that’s all peanuts compared to how hard it is to build a company because of the human complexity of rallying a team of diverging, exceptional minds in the same direction. 

The thing about Phase Two is that it requires you to excel at two completely different things – Plumber Mode, to contribute tangibly to the company's goals as an individual contributor and strategist, and Preacher Mode, to create the message that will rally others in the trenches.

Switches and boxes

The ability to seamlessly switch each mode on and off at will  – and cancel all the noise coming from your environment – is what separates the best builders from the rest.

I remember the day when a big potential customer called me saying they would postpone hiring Enter for a few months and my stomach turned because the quarter would close in a week and that client was critical to us meeting our revenue target. Yet I was at another prospect’s office about to pitch Enter to the CEO of a large telecom company, and I had to cancel out all my distracted thoughts about the revenue target. I got back to the office pumped because the CEO meeting went well and felt ready to revert the client’s decision not to sign with Enter – just to hear that a teammate’s father had been diagnosed with terminal cancer, and they needed to go home for a few days. While I spoke to him, I looked him in the eyes and showed them they were the only thing that mattered in that moment. As soon as he left, I thought about my father, who I hadn’t spoken to in several days because of how busy things were, and my eyes filled with tears – but I had to box that away to call that one client with energy and poise to get them across the finish line to sign the contract before the quarter ended. Spoiler: we did sign them.

Enter’s first two years have been a constant effort in creating mental switches and boxes for stuff in my head. It has become the most important skill to move from Plumber Mode to Preacher Mode, from comforting a teammate to closing our Series A to closing a million-dollar client – all in the same day.

As I reflect on my founder journey two years in, I wrote this to help other builders get their own thing off the ground. I hope you also find your true self in the process.

Enter became my life’s mission because I have found a routine over the past two years of self-actualization where challenges never end. Our outcome as a company is the result of thousands of vectors moving in different directions (team, customers, regulation, technology trends, marketing, interest rates) and handling all of them at once is the most stimulating thing I have ever done. “Pressure is a privilege,” like a big sign displays at the US Open Arthur Ashe stadium.

Looking forward, next month we will launch Enter OS – our operating system for enterprises facing mass litigation, which goes beyond drafting a lawsuit answer and handles a lawsuit end-to-end. Our platform now includes AI agents that are capable of detecting document tampering, recommending settlement amounts, interpreting live updates from the court websites and evaluating the chances of reverting a ruling on appeal:

As we begin our third year, Enter OS has kept us busy and reaffirmed the early-stage energy that our small team embraced back in 2024 when we launched the answers product in a week's time. The ship is still sinking, and it will always be sinking in the Enter religion no matter how much money we raise or clients use our product. 

That is the infinite game that keeps us going. The good news is that, unlike academic challenges, there is no graduation for building a remarkable company. Product puzzles never stop popping up. So now we head into year three at building Enter with the lessons on Phases and Boxes that we learned in the first two.