
Co-fundador & CEO en @LexgoLegaltech. Comparto mi experiencia en https://nitter.gq/t.co/AIR5SNyBsC.
Santiago, Chile
Joined September 2019
- Tweets482
- Following410
- Followers174
- Likes6.4K
when we went to raise our series A, every investor we pitched went with atrium and stopped calling us back. so we had to get profitable, which is probably why we're still here.
now there's a new wave of neofirms, and the hard questions haven't changed.
the big one is the exit. most of these are two companies stitched together, a law firm owned by lawyers and a tech company owned by investors. the tech company's only customer is its own law firm, and i've never heard a good answer to who buys that.
the work is the other problem. they're chasing startup contracts and redlines, the exact stuff AI is commoditizing fastest, while the real growth is companies getting sued faster than anyone can staff the defense.
and the AI-native label is for the pitch deck. no client has ever asked their lawyer how native the AI is
Hire out of pain. Don't hire because you think you'll need someone soon or maybe sometime later. Wait until you or your team are actually hurting: working weekends, missing family dinners, dropping balls. That pain is the signal that the role is real. I learned this the hard way after watching founders (including myself) hire ahead of need and end up with people in roles that weren't fully formed yet. When you hire out of pain, you know exactly what the job is because you've been doing it yourself. You can evaluate performance because you know what good looks like. And the new hire knows you'll step back in if they fail, because you were just doing it last week.
Leo Barrientos retweeted
After Brex I had decided I didn’t want to start another company. But I found my calling. I’m starting another fintech company that can change the world. I wasn’t looking to startup another startup but this one was impossible not to. The opportunity is too big. But the problem is very technically, operationally, regulatory and financially complex. So I’m looking for a founding CTO that is interested in coming in this adventure with me. It’ll be hard, it’ll take long, but it’ll be worth it.
Signs you’re a good fit:
- You're a technical dictator, not a facilitator. Consensus is cosplay for avoiding accountability.
- You've built systems where bugs mean lawsuits, not rollbacks
- You believe big engineering teams are a symptom of bad architecture and weak leadership
- You're obsessed with ontologies and data models. You know most systems are rotten at the core because engineers treat modeling as boring.
- You optimize your own taxes, loans, and entities like it's a competitive sport. You think most people leave money on the table because they're lazy.
- You've optimized your LLM setup obsessively. Engineers who use ChatGPT with default settings are bringing a mass knife to a gunfight.
- You think "speed vs. quality" is a cope for teams that are bad at both.
- Makes fun of 9-to-5 engineers that rest-and-vest
- You have an extremely high bar for talent and still aim to be the best engineer on your team. Not secretly. Openly.
- You believe the PM role exists because most engineers are lazy about understanding the problem. The best engineers make PMs redundant.
The role is in person. In the Bay Area. All-day every day. If you’re interested, send me an email at: [email protected] (we don’t have a name yet!)
Leo Barrientos retweeted
Everytime I get mad at people in the cheap seats criticizing founders in the arena, I remind myself of what Giannis said. Arguably my favorite response to a reporter ever.
Leo Barrientos retweeted
Este gobierno partio con la tontera extrema de Izkia Siches en el sur donde le dispararon y esta terminando con la negligencia extrema de Pardow que todos pagamos.
Espero que los chilenos no nos olvidemos de quienes son.
Leo Barrientos retweeted
Replying to @cgainza
Hola. ¿Dónde está la falta de respeto en encontrar demencial que un órgano del Estado (laico) solicite "pedir permisos a los espíritus" -de la creencia o cultura que sea- para autorizar construir un proyecto en plena ciudad regido por normas humanas establecidas democráticamente?
Leo Barrientos retweeted
"Durante años el área legal fue vista como una función aislada del negocio. Pero eso está cambiando hacia las Legal OPS. El rol del equipo ya no puede seguir siendo artesanal, la transformación digital llegó".
Lee la columna de Leonardo Barrientos aquí:
estadodiario.com/columnas/le…
Leo Barrientos retweeted
🔹Óscar Landerretche, economista del comando de Carolina Tohá.
Liquida a @GabrielBoric y al Frente Amplio.
" Me gustaría que si hay un gobierno de derecha traten de no derribarlo y convertir al país en un maldito infierno y de quemar iglesias ".
🔥
Leo Barrientos retweeted
La ley de funerales narco es el más claro ejemplo de la derrota del estado y la liviandad política. Regular el cómo se debe realizar un acto ilícito revela la tontería legislativa hecha en chile.
Leo Barrientos retweeted
The future is bright ✨
We have signed General Manager Nico Harrison to a multi-year contract extension.
#MFFL
Leo Barrientos retweeted
(1/5) Hoy en @icare_chile, con @RBergoeingV @AndreaButelmann y @OLanderretche hicimos una propuesta CONJUNTA por un PACTO DE DESARROLLO de largo plazo ambicioso y con medidas jugadas para abordar 13 verdades incómodas y salir del estancamiento estructural. df.cl/economia-y-politica/ma…
Leo Barrientos retweeted
As promised, here's the best publicly available version of Facebook's Little Red Book
Over 2.7k people asked for the link, and I don’t have time to send it out individually—so please share
Enjoy! Will link the PDF below 👇
Convinced a university to scan Facebooks little red book on a $150k archival scanner
The best PDF’s I could find were @amasad’s and a remastered version that were both low quality
Reply if you’d like me to send you the link when it’s ready - should be the highest quality publicly available version to ever exist
Leo Barrientos retweeted
Founder & CEO is a common title, especially in tech.
It happens to be my title too.
I've come to believe it's an impossible title. You're either CEO, or you're Founder. You can't hold both full-time jobs.
And unless your company is probably 100+, CEO isn't really a job anyway. It's more of a role someone needs to play occasionally.
There simply aren't that many big picture things or decisions to "execute" day in and day out — or even week in and week out — to make it a true full time job. A role yes, a hat to wear yes, a full-time job at a smallish company? No. It's part-time at best, quarter-time even better.
Further, the fundamental responsibilities of Founders and CEOs are at odds. Having them mashed up in the same title is as ridiculous as having someone who's a "CTO & Chief Luddite".
Why's that? Because a Founder's job is injecting risk into the business. It's flooding it with new ideas, stuff that seems hard to do, ideas that no one else would dare try, placing the kinds of bets that only someone who started the damn thing would be willing to wager. A Founders' job is basically to stay in business by almost always putting it out of business.
A CEO's job? Just about the opposite. It's reducing risk, executing diligently to achieve obvious goals, staying in business at all costs. It's primarily about about being conservative, keeping the company's collective cool, and not letting things get out of hand. Just about everything that a Founder isn't doing. A CEO's job is to stay in business by not allowing the company to do anything so stupid that it could go out of business.
See? They're such different things. The minds powering the pistons run on different fuel.
But I get it. It's a wonderful boost to the ego to hold the top two jobs in a company — especially when the original sin of starting the damn thing was your decision. And yes, someone ultimately has to make the big calls, no matter which side they fall on. And given that you were the first one in the door, you're the natural and convenient standard-bearer. Your skeleton key fits both locks.
Founder is a unique position as it's the one job that can't be replaced. It can be eliminated, certainly, as many companies go founder-free after some time. But once the person who started it isn't there, you can't bring someone else in who started it. The closest thing then becomes a CEO.
So I've shifted my personal thinking. As long as I'm still here, I'm picking a side. I'm a Founder. That's my strength, that's where I can bring the most. Which means we don't really have a full-time CEO. I'm simply the part time one that fills the void when we need to bridge the gap, make a final big decision, and move on. As it should be.
Leo Barrientos retweeted
The point of a startup is to make usable technology for others. When you make software, you have to watch at least 10 people use it. Sit next to them and say absolutely nothing. Force yourself to marinate in the failure of your product design.
Every version 1 of any software will be absolutely destroyed by first interaction with users. You need to watch your new creation be absolutely misunderstood by users to reform version 1 into the one that actually works.
There is only one path: figuring out where the sharp edges, the places people get caught, the assumptions you make as a builder that turn out to be wrong, and then relentlessly sanding it down so that anyone can use it.
That is good design. That is the key to a good product. There is no shortcut for this.
WATCH USERS AND CRINGE AND THEN FIX IT.
SAND DOWN THE EDGES.
Leo Barrientos retweeted
Conoce la diferencia entre los pre-money y post-money #safes (Simple Agreement for Future Equity) de @ycombinator, cómo funcionan y en definitiva, cómo cada uno de ellos puede impactar tu participación en tu #startup!
medium.com/lexgo/pre-money-v…
Leo Barrientos retweeted
En tiempos en que está costando cada vez más levantar financiamiento para lanzar o hacer crecer tu #startup, confeccionamos una lista de todas las opciones disponibles para conseguirlo, según la etapa de tu empresa: medium.com/lexgo/cu%C3%A1les…
Leo Barrientos retweeted
Una breve guía acerca de cómo elegir y trabajar con tu abogado (sin sufrir haciéndolo) de Lexgo con ❤️
lexgo.cl/blog/guia-para-eleg…

























