Kieran Osborne — Advice-first estate planning, tech & consultancy
Advice-first · tech-forward

I am Kieran Osborne.
I build things that
help people be
better protected.

I'm not a lawyer. I'm not a salesman. I build advice-first estate planning, useful technology, and I help good people run their businesses better, because your legacy and your firm deserve better than a free template or a hard sell.

Connect on LinkedIn See what I do
All systems advice-first
Kieran Osborne, estate planner and founder of Squiggle Consult and YEPP
Squiggle · YEPP
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advice-first
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What I do

Four things, one principle: do the right thing, not the easy thing.

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The ventures

Six ventures. No external investors. No inflated nonsense.

See all ventures →
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Kieran Osborne, speaker and entrepreneur
On stage

I'll speak honestly, even when it ruffles feathers.

Estate planning, legal tech, AI and building a business the right way. I talk about the things most people in my industry would rather not.

Book me to speak

Let's talk. No pitch, just a proper conversation.

Whether it's your estate, your firm or your tech, drop me a line and let's see if I can help.

Connect on LinkedIn Other ways to reach me
Technology & legal tech

Good advice should scale without losing the human bit.

I'm a genuine tech nerd who happens to run an estate planning business. Honestly, this is just what I enjoy: building tools that kill the busywork so real people can spend their time giving real advice. YEPP is one that grew big enough to share, though I'm relaxed about where it heads next. And I'm always up for helping someone figure out their own.

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Building things

Built for planners, because I am one.

YEPP started as a fix for my own frustrations. Clunky tools, endless admin, software that clearly wasn't made by anyone who'd sat with a family at their kitchen table. I loved building it. If you're wrestling with the same problems, I'm always happy to compare notes.

Fancy a chat about tech?
Kieran Osborne at the Squiggle office
Business consultancy

Helping good people run their firms better.

I've built and scaled businesses the hard way, and I've made the mistakes so you don't have to. I sit down with founders and peers to find the friction, fix the systems, and put the right technology in the right places, so growth feels deliberate rather than chaotic.

Kieran Osborne, business consultant

How I help

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Book time with Kieran
The ventures

Everything I build sits under one honest mission.

No external investors. No inflated nonsense. Just thoughtful, strategic growth across estate planning, technology, training and giving.

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Visit site →
Speaking

Honest talks, from someone who's actually done it.

I speak to planners, founders and teams about the things that matter and the things people usually dodge. Here's what I'm often asked to talk about:

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Book me to speak
Kieran Osborne, speaker and entrepreneur
Kieran Osborne, black and white portrait
My story

Doing the right thing, not the easy thing.

I'm Kieran, an entrepreneur, estate planner and charity trustee. I came into this industry frustrated by how it treated people: too much sales, too little advice. So I built something different.

Squiggle Consult puts proper advice first. YEPP gives planners tools that actually help. Squiggle Academy brings good people into the profession, and Squiggle Giving turns our work into something bigger. As a trustee of The Bloomers Trust, I try to put my time where it matters.

Outside of work? I'm a tech obsessive, a builder, and someone who enjoys helping other founders untangle their businesses. I'll speak honestly, even when it ruffles feathers. I think you deserve that.

Get in touch
Say hello

Drop me a line.

The easiest place to reach me is LinkedIn. That's where I'm most active, and where a lot of these conversations start. No pitch, no pressure. If I can help with your estate, your firm or your tech, I'd genuinely like to hear from you.

Connect on LinkedIn Email me
Find me elsewhere
Same handle everywhere: @iamkieranosborne.
Blog

Thoughts on advice, tech and doing right by people.

Honest writing on estate planning, legal tech and building a business the right way. No jargon, no filler.

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Enjoyed this? Let's carry it on. Connect on LinkedIn