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Episode 9 — Small audience, big leap

This week on Simon Says, five very different dreams share the same heartbeat: start before you feel ready.

• Daniel Sheehan — Travel creator
  He doesn’t have a million followers. He has a map and a point to prove. We swap “waiting to be discovered” for a simple promise: bring places to life so well that brands want to be part of the story.

  YT: I Wish I Did That When I Was Younger

  IG: iwishididthattravel

  
  

• Sav — Smile Shield
  A dad with an idea to help families actually brush, not just mean to. We turn good intentions into a movement you can feel — the kind that makes a kid proud to show their grin.

  IG: sav160

  TT: Sav1602

  Web: smileshield.co.uk

  
  

• William Matthews — Oyster Holiday Cottages
  A small team on a windy coast trying to build something that feels like home. We talk about hospitality as love: welcome notes, off-season memories, and leaving a place better than you found it.

  IG: Oyster Holiday Cottages

  
  

• Declan Natras — From the Army to founder
  Standing on the edge of civilian life with a head full of ideas. We talk about courage in quieter forms: buying back your time, making your first £1k, and choosing the long road on purpose.

  
  

• Lily (14) — Future sports broadcaster
  A teenager with a voice that belongs at the match. We sketch the first steps of a dream most adults are too shy to say out loud — and promise to check back soon.

  TT: lily.gallagher74

  
  

Follow Simon Says on Spotify and subscribe on YouTube.
Your support helps us fix the education system, teach people business, and give knowledge away for free.

Sponsored by HighLevel
This episode is sponsored by HighLevel — the all-in-one platform for funnels, CRM, marketing automation, and lead management.
With my link, you get 30 days free.

👉 Start your 30-day free trial here: https://www.gohighlevel.com/simonsays

—

In this episode of Simon Says, Simon Squibb helps four callers turn raw intent into real plans — from wildlife photography to wellness retreats.

• Hiran , @hiranmano— NYC technologist with a wildlife-photography dream. We scrap the “non-profit” label, set a $4,000/month client target in 6 months, and map revenue paths: paid shoots (zoos/NGOs/brands), print sales, a photo book, and gear sponsorships.

• Philip Gidding — Electrician launching a pie-and-mash shop with a pay-it-forward model. We design a zero-budget launch: niche first (serve trades), film taste-test reactions at wholesalers, partner for in-store sampling, and use content to drive preorders.

• Allegra Melloul, @a1legra — Paris-based creative torn between film, teaching, and service. We focus the mission: make the Divine Comedy film trilogy in Italy, fund impact work (orphans) via profit, and keep a small content-services roster for runway.

• Janine Hanlon, @janinehanlonlivingwell — Building affordable women’s wellness retreats. We kill limiting beliefs, expand beyond IG to TikTok/YouTube, and execute a revenue-share weekend pilot with an existing venue, then use profits to underwrite free places.

Follow Simon Says on Spotify and subscribe on YouTube.
Your support helps us fix the education system, teach people business, and give knowledge away for free

Sponsored by HighLevel
This episode is sponsored by HighLevel — the all-in-one platform for funnels, CRM, marketing automation, and lead management.
With my link, you get 30 days free.

👉 Start your 30-day free trial here: https://www.gohighlevel.com/simonsays

In this episode, Simon Squibb speaks with four young dreamers who are already challenging the system:

• George Pemberton (16) — wants to launch a hybrid athlete coaching business with his brother. We design a hook (“Get fit for free”) and debate whether he should pursue A-Levels or take a gap year to go all-in. (@nobs.club • @exalt_ekene)

• Francesca O’Sullivan — shares her raw story of losing her son and feeling lost after redundancy. In a 2-minute challenge, we explore how pain can become purpose, and how her writing could grow into a community. (@frankiesaturn)

• Harrison Nott (15) — already turned over £100K with his invention CoolTowel™. We unpack how to balance scaling a product business with building a personal brand that inspires millions. (@harrisonnott)

• Pijus Pranckus (18) — building a “Siri for business” to transform how companies train staff. We drill into clarity, focus, and how to pitch without losing people in the detail. (@jpcustomsie)

• Julia Hammond (18) — launching Haya, a modest fashion brand redefining style and accessibility. We map out low-cost launch strategies, from TikTok to “modest marketing” campaigns. (@hayacollectionca)

Follow Simon Says on Spotify and Subscribe on YouTube.
Your support helps us fix the education system, teach people business, and give knowledge away for free.

In this episode of Simon Says, Simon Squibb speaks with:

• Alex Montgomery (@generation.soil) — growing Generation Soil, aiming to get everyone obsessed with soil and normalize composting. Should he stay a CIC or switch to Ltd to scale?

• Rohan Dayal (@rohan31d) — building a global bookkeeping platform. How can he win UK SME clients and convert demos into paying contracts?

• Eilish Clarke (@cbt_by_ec) — a CBT therapist and nurse designing pre/post-natal mental health support. How do you market a service people don’t know they need until it’s too late?

• Chloe Moss — says she has no dream. In Simon’s 2-minute challenge, we uncover her true mission live.

• Caleb Cottam (@CertifiedRubbish) — tackling the UK fly-tipping crisis with Certified Rubbish. How to onboard users en masse without burning cash on ads?

• Snow (@snowapares) — aspiring to build the #1 global wellness platform for travelers. What’s the smartest path to land a first hotel or airline pilot?

• Ryan Loy (@_ryanloy) — launching a videography studio for trades, targeting £10k/month. What’s his fastest route to two paying clients in 30 days?

• Ben Fifield (@benvironmentalist) — innovating pizza packaging to replace single-use plastics. How to convince EU manufacturers to test and supply at scale?

Sponsored by HighLevel
This episode is sponsored by HighLevel — the all-in-one platform for funnels, CRM, marketing automation, and lead management.
With my link, you get 30 days free.
👉 Start your 30-day free trial here: gohighlevel.com/simon-says

In this episode of Simon Says, Simon Squibb speaks with:

• • Dani Ransom (22) — launching pocket-size flushable wipes; we map a 7-day street MVP and a 30-video validation sprint. (@danielleransom_ • @pocket.wipes)

  • Alex Garrett — quitting to install Apple CarPlay and audio; we design a co-founder plan, retail demos, and a simple quote funnel. (@alexgarrett_ • @GarrettsAudioWorks)

  • Oliver Fallbrown — building Farmploy to solve farm staffing. (@Farmploy)

  • Daniel Sheehan — says he has no dream; in our 2-minute challenge we help him find it.(@_dansheehan)

  • Roman Prokhorenko — aiming to build a global live-events company with 6-month runway. (@prokhorenko.roman)

  • Jess Telling — autistic theatre maker championing accessibility.s. (@thejesstelling • @chameleon.play)

• 
  

  Sponsored by HighLevelThis episode is sponsored by HighLevel — the all-in-one platform for building funnels, automating marketing, managing leads, and more.

  With my link, you get 30 days free.⁠Start your 30-day free trial with HighLevel now.⁠👉⁠HighLevel⁠

  
  

In this episode of Simon Says, Simon Squibb speaks with:

• Jack Evans (@Jack.the.ripper_13) — stuck at £300 and a day job, wants to launch a construction testing business. Simon helps him make a decision: get one client, take a 50% deposit, lease a van for a month, prove it in 30 days

• Noah Chant (@riznfootball) — changed careers to build a grassroots football brand/coaching offer. Simon helps him think about how to get the word out.

• Irene (@Thelittlelibraryltd) — has 74p and asks if a pop-up is realistic. Yes it is.

• Michael Soula (@lumnious) — wants a pancake brand to help his mum, but is stuck thinking about the production process.

• Tasha Armaine (@Get_tashed) — a burnout-recovery café/wellness hub concept.

• Josh Phillips (@joshphillips360) — dream: travel and build NeuroTrek learning hubs.

  _____________________________________

  Sponsored by HighLevelThis episode is sponsored by HighLevel — the all-in-one platform for building funnels, automating marketing, managing leads, and more.

  With my link, you get 30 days free.⁠Start your 30-day free trial with HighLevel now.⁠👉⁠HighLevel

In this episode of Simon Says, Simon Squibb speaks with:

Noah, a 16-year-old with $2,000 saved, dreams of building a fishing resort.

Harley, 25, wants to turn a van into a mobile music and podcast studio with just £1,000,

Bruno, 23 (@cyasecurity1), is building a free cybersecurity education platform while juggling university and work.

Nikhil from India has $100 and a mission to give artists freedom in manga and comic publishing.

Abby from the UK has £5,000 and a dream to launch “Trash Talk,” a litter-picking community group that tackles loneliness.

Sponsored by HighLevel
This episode is sponsored by HighLevel — the all-in-one platform for building funnels, automating marketing, managing leads, and more.

With my link, you get 30 days free.
⁠Start your 30-day free trial with HighLevel now.
⁠👉HighLevel