Sasha Cayward

Sasha Cayward

Chief Community Officer @ Hubble | Ex-Techstars FemTech Founder | Content & Storytelling Master | Startup Mindset Support Human

I specialize in

Career Advancement
Founder Advice
Mental Health
Go-to-market
Growth
Story & narrative
Personal Branding
Health

Your community is your moat when building a generational product

Background & Highlights

MSc Organisational Psychology, LSE · 5+ years coaching founders & VCs globally

London School of Economics

2022 – 2023

Built a distinctive personal brand of over 18k across platforms

Curator of high-touch cultural & networking experiences - from VIP cultural tech events on the French Riviera to founder gatherings at landmark London venues

TechStars '22 founder (~1% acceptance) - built an early AI powered cycling syncing apps, won competitive grants from UCL Entrepreneur Society & Starling Bank

About me

New here? The 15-min "Pick My Brain" is for ONE pressing question - fast, direct, and actionable :) — Here's what I've learned building companies, communities, and a following: the founders who win aren't the loudest - they're the ones people want to gather around. I hit rock bottom in 2018 — autoimmune disease, mental health struggles, injury, and walking away from my own startup. What pulled me back wasn't a growth hack. It was people. The right rooms, the right conversations, the right story to tell myself about who I was becoming. So I rebuilt around that — and it's now what I do for a living. Today I'm Head of Community at Hubble, where I connect early-stage founders with the operators and investors who've already solved what they're stuck on. I curate high-touch events from the French Riviera to London's landmark venues, and I write "the locker room" to 13.5k+ founders. The throughline in all of it: community and story are the real moat. Product gets copied. A community that believes in you doesn't. I coach founders on the two things most of them under-invest in — how to build a community that sells for you, and how to tell a story (in content and in person) that makes people lean in. And because I'm an organisational psychologist and ex-athlete, we do it in a way that builds you up instead of burning you out. Book a session for: ✔ Building community that sells your product (not just a Slack that goes quiet) ✔ Building a personal brand & content engine on LinkedIn ✔ Storytelling & narrative — for your brand, your raise, and your reputation ✔ Networking & real connection that don't give you the ick ✔ Founder mental fitness, resilience & identity as you grow It doesn't matter if you're pre-launch, mid-scale, or already exited. If you want to be the founder people gather around — and actually enjoy the building — this is your call. At the end of the day, it's you against the old version of you. Book a call. Let's get into the weeds. :)

You'll get advice on

  • How to build community that sells your product
  • How to build a personal brand on LinkedIn
  • Founder mental health and resilience
  • How to break into startups / VC

Real feedback from real sessions

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