Tom Maitland

Building @askfilly - AI analyst for founders. Previously co-founded Raisely ($1bn raised for nonprofits). BI tools don't let you ask 'why' — Filament does.

[Tom Maitland @TomMaitland]

Founders face an false choice: move quickly but blind, or slowly but data-informed.

Before building Filament, I spent 7 years stuck in this trap at Raisely.

Here's what I learned about why BI tools fail founders: 🧵

[Tom Maitland @TomMaitland]

export to csv should be the least used feature of software

[Tom Maitland @TomMaitland]

@s_chiriac Data analysis in minutes - https://t.co/fONkhya1CE

[Tom Maitland @TomMaitland]

I sold my last businsss to private equity. Heres what I'm doing for the next run:

1) build a growth engine. Read Traction and implement the principles. Lock in your growth engine and get really f'ing good at it so you can so a clear bow tie funnel.

2) keep meticulous records. Every contract. Every employment agreement. Every IP transfer. Keep them in a folder they'll all come up in diligence.

3) have a crystal clear shareholders agreement. It's so easy to say "we'll figure this out later" but sales move quickly. Make sure everyone is on the same page.

4) know my metrics. Speaking to acquirers and investors forces you to know your key numbers fast - churn, customers, pipeline, win/loss, if you don't know these you're missing a trick

5) optimise for ebitda. Profit is good! We were bootstrapped. Profitability signals health.

Lemme know what else you wanna know.

[Tom Maitland @TomMaitland]

Data is where most founders fail. Hear me out.

1-10 users you know them personally and you email them every month.

10-100 users you know them all by name but you kinda don't know what's going on with their accounts

100-1000 users and you've got no idea who does what.

Human brains can fit like 200 people in them. Users + family + friends and you're all out of space.

CRMs don't fix this. They are an external memory, but you can't see trends.

At my last business - this is when I turned to SQL. what are they doing? What is our activation rate? Why are numbers down?

Writing sql sucks. And most people can't do it.

AI is really good at it.

It's why we've been building Filament - it can write the SQL and just give you signal back.

[Tom Maitland @TomMaitland]

Installed iOS 26. Best pocket warmer.

[Tom Maitland @TomMaitland]

I don't know who needs to hear this. If you're in IT and you're rolling out Copilot as part of your "AI strategy", your whole team is already using ChatGPT on the side.

[Tom Maitland @TomMaitland]

This week surprised me.

Spoke to 10 different founders about how they're doing reporting and data analysis right now.

Everyone is trying to analyse data across multiple platforms. Everyone is doing it in Excel and it's taking hours 😱

Some examples:

- Checking sales pipeline against meetings booked in Calendly
- Analysing customer retention and repeat purchase rate after campaigns
- Associating traffic performance (email, specific campaigns, paid) with actual revenue
- Mapping service delivery by region and pulling impact data for reports

I thought the problem most folks were experiencing was just that data wasn't accessible. They couldn't dive into it.

But it's connecting data between different tools that stood out this week. Your customer journey doesn't live in one app... making those links invisible.

Building @AskFilly to solve this. Back to work.

[Tom Maitland @TomMaitland]

@thdxr claude code will win this one for sure – the vibe coder tantrum had to end.

[Tom Maitland @TomMaitland]

I'll be sharing founder lessons, building in public, and calling out the usual startup bullshit.

Welcome along.

[Tom Maitland @TomMaitland]

Founders face an false choice: move quickly but blind, or slowly but data-informed.

Before building Filament, I spent 7 years stuck in this trap at Raisely.

Here's what I learned about why BI tools fail founders: 🧵

[Tom Maitland @TomMaitland]

If you're a founder trying to make data-driven decisions without hiring a data team, you're who we built this for.

Try it: https://t.co/aLSC3auOoA

[Tom Maitland @TomMaitland]

At Raisely, we helped nonprofits raise $1bn online and exited in 2023.

5 years in, we built data infrastructure so the team could make informed decisions. Data warehouses, ETL pipelines, Metabase. The works.

It was amazing... and absurdly complex for what should be a solved problem.

[Tom Maitland @TomMaitland]

@dean_mcpherson no comment

[Tom Maitland @TomMaitland]

@s_chiriac Instant data analysis

https://t.co/YsGMeq8uzg

[Tom Maitland @TomMaitland]

@elonmusk Wait, we like cancel culture now?