Joseph Pipia

Cofounder at Carethink

[Joseph Pipia @josephpipia]

@bhalligan Starting the explanation with “reducing ~14%” makes it self-explanatory, and the rest of the letter loses its meaning afterward.

[Joseph Pipia @josephpipia]

@hthieblot Learn to work with constant uncertainty.

[Joseph Pipia @josephpipia]

For a long time, I have been working on my communication skills.
I want to explain ideas in a way that people understand clearly, and remember correctly.
I have received a lot of advice over the years from coaches, mentors, and other people close to me.

But one of the most transformative lessons came from my co-founder.

He helped me understand that clear communication requires sacrifice.
- You cannot say everything at once.
- You cannot include every detail, every angle.

Because when you try to say too much, the message becomes blurry.
- People stop understanding what really matters.
- And worse, they remember the wrong thing.

If you are describing a product, an idea, or a problem, you have to make hard choices:
- What is the core point?
- What do I want people to remember?
- What can I leave out for now?

The same is true in conversation. Once you move on from a point, going back to add forgotten details often weakens the message. It creates noise and confusion instead of improving clarity.

This goes far beyond communication. It also shapes how we build product, design workflows, and present value to users.

Simplicity is rarely accidental. It comes from making hard choices about what to include, what to leave out, and what truly matters.

Clarity is not just about using better words. It is about making better choices.

[Joseph Pipia @josephpipia]

Having design partners can be a huge advantage for a startup. Working closely with customers helps founders get close to the real problem. You see workflows firsthand, learn faster, and build with real-world feedback.

The risk starts when the relationship is not structured well, especially when a design partner has ownership and control over, the startup or the product. That is when a product can start drifting away from the market and toward the needs of one organization. Or even worse, internal politics can start shaping what gets built.

And in the long run, that is not good for the design partner either. If the product is pushed too far toward one organization’s needs, it may never become the best solution in the market. Eventually, a stronger and more market-driven product may win, and the same partner may end up choosing that instead.

The best design partnerships work differently: they give startups access, learning, and feedback, without taking control of the company or the product.

We’ve been lucky to work with design partners who understand this well.

[Joseph Pipia @josephpipia]

@bhalligan In my view, this is about laying off overhired employees, and in many similar cases, it is also freeing up resources for AI infrastructure investments.

[Joseph Pipia @josephpipia]

One thing we don’t do at Carethink is study other products as a reference when building a feature. It’s too easy to pick up complexity and overthink edge cases that may never matter. Instead, we immerse ourselves in the user’s actual job and build the simplest way to get it done.

This is one of the reasons our features get picked up so quickly by virtually all of our users.

[Joseph Pipia @josephpipia]

For the past several months, my cofounder @barrau_n and I worked directly from our customer’s practice.

They gave us desks, and we got fully immersed in the daily work, sitting alongside the team.

This experience shaped how we’ve built Carethink.

Instead of relying on interviews or feature requests, we focused on how users actually did their jobs. We observed how they navigated constraints, and solved problems in real time.

Most of the features we shipped were never requested by users. Yet every release saw immediate uptake because the features addressed the root causes of the problems users were facing, rather than hypothetical needs.

[Joseph Pipia @josephpipia]

Stuck in traffic yesterday, my Uber driver said Tuesdays and Thursdays are the busiest now since so many people WFH on Mondays and Fridays. Restaurants are packed on Thursdays too. Feels like Thursday is the new Friday. Hard to believe productivity is the same.

[Joseph Pipia @josephpipia]

@HarryStebbings @jonsid Internal teams at enterprises never lacked engineers. They are not solving a problems, they are completing tasks. Startups with scarce resources are forced to solve problems efficiently. SaaS/ready-made solutions will be needed even more with the next level of automation.

[Joseph Pipia @josephpipia]

Creating “AI employees” is the wrong way to think about automation. It’s backward-looking. New automation lets us redesign work in a fundamentally more efficient ways, which means creating new roles and removing old ones, not just replacing existing roles with AI.

[Joseph Pipia @josephpipia]

If a VC has just 1 pre-seed and 30 seed investments, it can technically call itself a pre-seed investor, but is it really?

[Joseph Pipia @josephpipia]

@barrau_n Most importantly we need to hire brilliant people who expand our capabilities and create new surface area for discovery. They notice patterns we miss, open new paths.

[Joseph Pipia @josephpipia]

Over breakfast before heading to AAO 2025, @barrau_n and I discussed how we are expanding our capabilities as we grow. We defined three areas:

[Joseph Pipia @josephpipia]

@barrau_n Thus, we need to hire to do tasks we already know we have but don’t have capabilities for.

[Joseph Pipia @josephpipia]

@barrau_n 3. Things we do not know that we do not know. These are blind spots. They can hide risks and also hide opportunities. This can be technical, about the market, or both.

[Joseph Pipia @josephpipia]

@barrau_n 2. Things we know we do not know. These are gaps we can close by learning or hiring.

[Joseph Pipia @josephpipia]

@barrau_n 1. Things we know we know. These are our current skills and experience.

[Joseph Pipia @josephpipia]

A must-read for aspiring founders

[first check $500k-1M pre-seed @ajhodls]

i've been getting *a lot* of inbound requests to check out founder pitches lately.

we have 100+ portfolio companies, many of whom I meet with on a monthly basis. so my bandwidth for cold inbound is unfortunately pretty limited. of ~300 cold emails a month, i only take ~1-2 meetings from cold outreach.

i know that sucks for founders, so i want to be transparent with some of my evaluation framework to help you calibrate outreach and help set expectations on how I think about opportunities at the pre-seed.

first, understand it's likely that venture funding isn't appropriate for your idea. venture is a very specific tool seeking outliers in markets that largely do not exist yet. most early-stage funds are looking for 100x (or greater!) returns, so your valuation and market focus needs to account for that. if you're hoping to raise at a $10M valuation, that means a $1B exit (or $2B+ exit factoring in multiple rounds of dilution). these types of outcomes statistically just don't happen often. there are maybe only a handful of liquidity events at that level per year.

so you probably should bootstrap until you have a clearer picture that there’s a real venture opportunity in front of you and be able to convince someone of the market potential.

but if you still want to try to pitch VCs, here's how you should focus your email outreach to capture attention:

1. you are "consensus"

if you have to ask yourself if you're consensus, you aren't. consensus founders typically have one these attributes:

- sold a previous company for $100M+
- raised $100M for a previous company
- raised $20M+ in previous company from a top VC
- early research team at top 5 AI lab (e.g. maybe one of like 100 people in the world)

if these aren’t you, you aren't consensus. These founders aren’t reaching out to me. they’re going straight to the biggest funds for the biggest checks. $20-100M++ in their first round of funding. There are only a handful of funds who write these checks and they all already know the founders.

2. you are "qualified"

qualifications are just linkedIn experiences. they typically are pretty poor signal for founder quality, but a lot of VCs seem to put a lot of weight on them. there are more popular qualifications like:

- worked at top 10 tech firm as engineer or PM
- graduated in CS/Math from top 10 university
- IMO medalist is now en vogue
- PhD in machine learning or equivalent is en vogue

there’s a lot of brand association weight here, so after the first 10-20 top companies or institutions, the allure starts to wear off. if this is you, congratulations, you get an easy pass to at least a handful of VC pitches.

if this isn’t you, you need to consider if it’s worth trying to work at one of these big companies for a few years to build the pedigree. I don’t think it’s worth it, but some folks do it and it’s a fairly predictable ROI.

if you worked at a lesser known company that's worth something, but the most important thing you can do is get a strong referral from another 1. consensus or 2. qualified founder (ideally someone where you worked on the same team)

3. you can build

ok so you didn’t work at the big labs, didn’t get a PhD from MIT, and are not a L5 eng at google. but anyone can build these days. and you can cook.

live products are king here. your pitch email should lead with a link to a live demo or a loom video showing your product. it doesn’t need to have thousands of users (or any users), but it does need to demonstrate your technical and/or product competencies. in the loom, talk about some of the features and why you think it’s special, talk about the inspiration and highlight the core 1-2 features you’re excited about and how you built them.

building software has never been more approachable then it is now with AI models and codegen. so if you aren’t able to ship a product demo that’s reasonably compelling, you probably aren’t ready for funding.

4. you have traction

ok you’re a decent builder, but maybe your product and tech aren’t anything to write home about. while it’s an important foundation, that’s not necessarily a dealbreaker.

if there are users of your product and they are using the product a lot, that’s pretty damn good signal. it doesn’t need to be thousands of users, even a handful of users is enough. but they should love the product. product outages or missing features should drive them crazy and have them messaging you at odd hours. 5 users in a discord that write you every few hours about feature requests is a great signal. if this isn’t the case, you probably aren’t onto something yet or you don’t sufficiently understand your audience.

many of the most popular companies started this way. If you aren’t embarrassed by the state of your product, you are not shipping fast enough. this is a signal that you aren’t getting out the door and engaging your customers enough.

and if you don’t understand your audience and how to engage them, you probably aren’t ready for funding yet.

5. you can tell a story

ok so you don’t have any traction and you don’t have any product to speak of. you aren’t in a great spot to raise venture capital. but there are the rare founders who can construct narratives that compel huge shifts in demand.

this is a very special and rare talent, so if you’re questioning if you’re in this bucket you probably aren’t. but your lived experience and empathy for a problem space is important, and you can build this muscle over time. practice your pitch and build an audience on x / substack / youtube. post on a regular cadence for months / years and demonstrate you can convince people of big shifts.

this is building latent demand; and it can be a valuable skill when paired with the builder profiles who can’t find a great market. if you have the following, you can usually convince great technical co-founders to join you on your mission.

but if you don’t have 10k+ followers all specifically engaged on a specific topic, you probably aren’t ready to discuss funding yet.

so to reiterate:

1. you’re consensus, congratulations. VCs come to you, you don’t even need to pitch.

2. you’re qualified. put together a pitch deck and hopefully some friends from your team at Facebook will make some good intros. this probably isn’t you, but if it is, congrats you’re also lucky.

3. you’re an outsider, no VC connections but you can hack. send demos! loom videos with voiceovers are even better. talk about what makes your technical insights or implementations special.

4. you’re an OK builder, but you understand your problem space incredibly well and you’re engaging customers on the regular. you have a product (it’s not perfect) but users are banging away on it and don’t churn even though it sucks. send anecdotes from users and early activation and retention statistics with ideally a few months of longitudinal data. revenue retention and revenue growth are the most important (if you have it)

5. you can’t build, you don’t have customers yet, but you’re architecting movements through narrative and mission. you’re still a few steps away from building a good foundation for a venture-backed startup but you have an important foundation -- attention. your narrative skills will be important for the next steps, but convincing a great builder will be important too.

those are most of what I think about when reviewing cold outreach. i only have time to spend maybe 30 seconds max on every email, so keep it short, and highlight one of the things above in a few sentences while linking to live demos, loom videos, linkedIn, github repos, etc...

follow-up emails are fine, but they should include meaningful progress on one of the items above (e.g. more customers, more product links, new builder co-founders, more followers). if you don’t have meaningful progress on those, it’s not worth following up until you do.

in conclusion, remember that founders are everything in this business. don’t be discouraged if VCs don’t respond. founders are the fuel of real meaningful change and innovation. i sincerely hope to see more venture capital in the world to catalyze more outliers who become the consensus founders of tomorrow. thank you for all that you do and having the courage to put yourselves out there! the world needs more founders.

[Joseph Pipia @josephpipia]

Started my first company at 28 with two kids (5, 1). Sold our condo, and later our only car, to get through. My cofounder and I worked day and night. Now it’s my second act, more intense. People say you should be 20 to do this. If age kills your love of building, it wasn’t love.

[Joseph Pipia @josephpipia]

Great article by MIT professors with lessons from the 1980s that are very relevant for today’s AI adoption.

https://t.co/rBxiLe95XH