Founded & Grounded

This week: the founder with one GCSE who bootstrapped his way from roadside marrows to a full agency exit. Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/founded. Application times may vary. Rates may vary.

"No one thought I'm gonna get through school. No one thought I'm gonna go to college. No one thought I'm gonna get to university. F*** it, I'm gonna do a business, 'cause no one's gonna think that either."

That's how this episode opens, and it's the engine behind everything Oliver Bruce has built.

A military kid who went to seven schools and was diagnosed with dyslexia and dyspraxia in an era when teachers just told him to stop being stupid, Oliver left school with a single GCSE in art. At 13, he was selling marrows on the roadside for 20p. At university, he built an app nobody downloaded, noticed businesses would pay for the videos instead, and pivoted into what became Pinpoint Media: a search, social and creative agency he bootstrapped for over a decade without raising a penny, then sold in December 2025.

It wasn't a straight line. Oliver gets honest about losing 110K during the pandemic chasing a side venture instead of focusing on the main business, and why even founders of rocket-ship companies have stared down payroll and wondered if they'd make it.

Then he opens up on the exit itself: why both sides used professional dealmakers, why he'll never negotiate his own deal again, and the 18 to 24 months of relationship-building that made the sale possible. Plus why retained revenue made the business sellable, what joining a big board has taught him, the burnout that paused his podcast for 14 months, his all-in bet on agentic AI, and the small matter of training to row 3,000 miles across the Atlantic.

Please note: this episode contains strong language.

3 KEY TAKEAWAYS

1. Ask for help as early as possible. Don't grind through it alone to prove a point. Asking is a quick hack; people genuinely want to help, and the founders who ask compound faster than the founders who don't.

2. Selling is a fair exchange, not a pitch. From marrows at 13 to agency retainers, Oliver's sales lessons come back to the same thing: trust, timing, and a clear understanding of what the other person actually needs. Get those right and confidence in your price follows.

3. Focus is what buys you freedom. Oliver's pandemic side venture brought in lots of turnover and no money. What actually built the business was staying on the core, building recurring revenue, and now learning to use AI well. That stability gives founders the freedom they were chasing in the first place.

WHAT WE COVER

- Selling marrows at 13, pricing confidence, and why every founder must learn to sell
- Cultural differences in selling: the US vs UK gap, from an Alex Hormozi event in Vegas
- Seven schools, one GCSE, and the neurodiversity the system missed
- The university app that failed, and the accidental agency it became
- Bootstrapping for a decade: reinvest everything, raise nothing
- Why distribution and strategy matter more than content alone
- Losing 110K in the pandemic, and the cost of getting distracted from the mothership
- Failure as feedback: "I have failed more times than I have succeeded"
- Nearly missing payroll, and why it's far more common than founders admit
- The exit: dealmakers, relationships built 18 to 24 months early, and staying friends with your buyer
- Why retained revenue makes a business sellable
- Life after exit: what a big board teaches you, and how to build one
- Burnout, the 14-month podcast pause, and relaunching as The Unlock
- Agentic AI, running content with agents, and rowing the Atlantic
- His curveball answer: why bother at all?

💬 Oliver has a question for you: what's your biggest fear around AI agents? Vote in our LinkedIn poll or tell us in the comments.

Guest: Oliver Bruce
Pinpoint Media: https://pinpoint-media.global
Website: https://oliverbruce.co.uk | LinkedIn: Oliver Bruce
The Unlock podcast: Spotify, Apple and all podcast players

Hosted by Ollie Tiramuragan Collard and Dr Becky Sage.

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The introvert who was told he looked too free-spirited, and whose software now runs ordering for the UK's biggest food brands. Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/founded. Application times may vary. Rates may vary.

"This poor lady had to say to me, 'There are concerns that you look a bit free-spirited.' They were worried I was suddenly gonna disappear and become a yoga teacher in Goa or something."

Simon Bos has spent more than 20 years building other people's startups at Gravitywell, his Bristol venture studio, watching entrepreneurs' hearts break over cheap builds that couldn't be rescued, and learning exactly what separates the products that work from the ones that die. Then he found his own gap: one of the UK's largest food-to-go manufacturers taking thousands of daily sandwich orders through a call centre. "Three BLTs, two chicken and bacon... no, three chicken and bacon." On the phone. Every day.

That absurdity became Mezze, the B2B ordering platform for food manufacturers. Since we recorded this conversation, it has grown into exactly what Simon describes planning here: the platform now handles over £10M of orders a month for names like Samworth Brothers, Pieminister and The Real Wrap Co. It has expanded into AI features and the US market. The playbook he lays out in this episode is the playbook that worked.

Along the way: a prime example of being an introvert founder, from months without networking to discovering that one-to-many content is the introvert's cheat code, plus the no-suit mantra, the three-month reset in Laos, and the client work (including the ADHD Love app) that reminds him why any of it matters.

3 KEY TAKEAWAYS

1. Cheap builds break hearts. Simon has had to tell founders "there's no way of fixing this, it's gone." Under-investing in your foundation doesn't save money; a bad build is often unrescuable, and rebuilding costs more than doing it properly once.

2. Introversion is a design constraint, not a defect. Simon went months without networking and felt guilty. The fix wasn't forcing himself into rooms; it was one-to-many: content, talks, a strong product. Build the version of visibility that suits your wiring.

3. Perspective is a tool you have to schedule. From regular stakeholder mapping to three months in Laos, Simon's pattern is to step back deliberately. When the day-to-day consumes you, you can't see the business; distance is what shows you where you actually sit in the ecosystem.

WHAT WE COVER

💬 Answer Simon's question in the comments or vote in our LinkedIn poll.

Guest: Simon Bos

Hosted by Ollie Collard and Dr Becky Sage.

🎧 New episodes every fortnight. Search "Founded and Grounded" on your favourite player.

#FoundedAndGrounded #StartupPodcast #Entrepreneurship #SaaS #IntrovertFounder

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Meet Greg, the adviser who built a career on saying what 1,000+ founders didn't want to hear. Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/founded. Application times may vary. Rates may vary.

The opener to this episode tells you two things about Greg McCallum: he's funnier than most business advisers, and he's more honest about the cost of the founder life than almost anyone we've had on the show.

1. Ask strangers, not friends. The most common founder mistake is failing to ask prospective customers whether the idea is good. Do it early and you're not just validating, you're building a pipeline, learning the language that sells, and writing your first sales playbook for free.

2. Sales is listening, not pitching. Professional sales hires get a three- to six-month ramp before anyone expects a deal, so give yourself the same grace. Never ask for the sale. Understand the need, demonstrate the solution, and let them ask you.

3. Honesty is the strategy. With customers, with investors, and hardest of all with yourself. Audit the skills you actually lack before you buy the domain or design the logo. Self-awareness is cheaper than failure.

Greg got kicked out of school at 15. By 16, he was running a restaurant floor. By 18, he'd quietly consulted for almost every bar and restaurant in Oxford. By his mid-twenties, banks were asking him into the boardroom. Then he deliberately took a soul-destroying telemarketing job for a year, because nobody would take his sales advice seriously until he'd done the hard yards himself. That decision led to sales leadership at Booksy (now unicorn status), C-suite roles across startups, and a mentoring practice that has helped over 1,000 founders worldwide, under a name he's turned into a brand: The No Bullshit Adviser.

In this episode, Greg gets honest about the mistake almost every founder makes, why working in sales won't teach you founder sales, the AI industry's dirty data secret his new startup Peer is built to solve, and the part nobody talks about: the anxiety, the dark years, and the alliances entrepreneurship never lets you make. Because when it all goes wrong, the question that matters is who you actually call.

Please note: this episode contains strong language throughout. Greg is called the No Bullshit Adviser for a reason.

WHAT WE COVER

- Kicked out of school, child of immigrant entrepreneurs, and managing hospitality floors at 16

- Accidentally becoming Oxford's teenage restaurant consultant

- A year of telemarketing to earn the right to give sales advice

- Booksy, C-suite roles, and 1,000+ founders mentored

- The one bad Trustpilot review that's secretly a five-star review

- Why psychometric tests are (mostly) bullshit, and skills audits beat personality labels

- Founders Unplugged: the podcast born from client calls that ran three hours over

- Peer and the dirty secret of AI: the data ceiling nobody talks about

- "Stop preaching work-life balance": Greg's unfiltered take

- Anxiety, depression, CBT, and becoming your own therapist

- The real sacrifice: friendship, founder loneliness, and why your support network is a survival mechanism

- The SaaS bubble, the bootstrapping comeback, and his one piece of advice: two words

💬 Greg's story got us thinking: when it all goes wrong, who is the one person you'd call? Tell us in the comments.

Greg also offers a free one-hour, no-strings advisory session to founders and executives. Details on his site below.

Guest: Greg McCallum

The No Bullshit Adviser: https://www.gregrcmccallum.com/the-no-bs-session

Founders Unplugged: https://podcasts.apple.com/gb/podcast/founders-unplugged/id1688034102

Hosted by Ollie Tiramuragan Collard and Dr Becky Sage.

🎧 New episodes every fortnight. Search "Founded and Grounded" on your favourite player.

👍 If you got value, leave us a review on Apple Podcasts. It genuinely helps the show grow.

#FoundedAndGrounded #StartupPodcast #Entrepreneurship #Sales #FounderAdvice

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The ex-model who turned an exploding kitchen of cauliflower into the pasta brand. Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/founded. Application times may vary. Rates may vary.

"My husband was just like, 'What's happening?' The kitchen was just an explosion of cauliflower."

That's how Sunny & Luna started, and this episode opens with it.

Giulia Berretti spent her teens modelling in New York on as little as 800 calories a day, inside an industry that treated food as the enemy. The daughter of a winemaker and a restaurateur, taught to make pasta by her nonna, she walked away. When COVID hit, she rebuilt her relationship with food into a business: vegetable-packed fresh pasta, born in her own kitchen.

She sold her first batches to neighbours on Nextdoor, pitched at the Bread & Jam festival with four gnocchi in a plastic bag, and Whole Foods and Planet Organic loved it. She then spent six months knocking on the doors of Italian manufacturers who kept asking "who are you?" until one said yes. When we recorded this conversation, Giulia was days from her first national listing and closing a £500K angel round. Today, Sunny & Luna is on the shelves of Sainsbury's, Ocado, Whole Foods and Planet Organic. Proof that everything she talks about in this episode worked.

3 KEY TAKEAWAYS

1. Never compromise on your non-negotiables. When the Ukraine war sent costs spiralling, Giulia held her quality line and raised prices instead of cutting corners, and customers rewarded her for it. Know what you won't trade, and price accordingly.

2. Passion plus authenticity beats playbooks. She built a standout brand in a category nobody had disrupted (fresh pasta) by staying close to what she genuinely knows and loves. Innovation came from her story, not from copying someone else's.

3. Persistence needs patience. "When the train is coming, you don't have to jump straight away." Ups and downs are the job. The founders who make it are the ones who keep going without rushing decisions that compromise the long-term vision.

WHAT WE COVER

- Modelling in New York at 18: the money, the pressure, and restricting to 800 calories a day

- Nonna's kitchen: the pasta-making childhood that became the business

- Testing demand on Nextdoor, and pitching retailers with a plastic bag of gnocchi

- Six months driving around Italy to find a manufacturer, and selling them the dream

- Why she'd never compromise on quality, even when costs exploded

- Two days of maternity leave, pitching Ocado ten days after giving birth, and the lesson in slowing down

- "A company fails when the founder is tired": mental health, therapy, and switching off

- Funding: bootstrapped on modelling savings, then a £500K round from angels who back her

- The future of food: real ingredients over fake meat, and Sunny & Luna as a lifestyle brand

- Why the business is named after her cats

💬 Giulia has a question for you. See the pinned comment and tell us your favourite.

Guest: Giulia Berretti

Sunny & Luna: https://sunnyandluna.co.uk | Instagram: @sunnyandlunaeats

Hosted by Ollie Tiramuragan Collard and Dr. Becky Sage.

🎧 New episodes every fortnight. Search "Founded and Grounded" on your favourite player.

👍 If you got value, leave us a review on Apple Podcasts. It genuinely helps the show grow.

#FoundedAndGrounded #StartupPodcast #Entrepreneurship #FoodStartup #FemaleFounder

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Nobody would give Hannah a room. So Hannah decided to control who gets one.Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/founded. Application times may vary. Rates may vary.

"I cold called all of the landlords I'd ever met at Bristol and got horribly rejected by most. Definitely cried a lot in the first few weeks."

That's how Hannah Chappatte started hybr and this episode opens with it.

Rejected by the University of Bristol on her predicted grades, she proved them wrong, got in, got a first, then skipped the consulting grad schemes to fix the thing every student complains about: finding a house. Fast forward, hybr has raised a £3.24M seed round and is building the one-stop rental platform for the UK's 3 million students, first-time renters drowning in jargon, deprioritised by agents, and at risk of exploitation.

This is a masterclass in validation, resilience and focus from a founder who did it with no network, no funding and no playbook, and who'll tell you straight: if you can avoid raising money, avoid it.

3 KEY TAKEAWAYS

1. Rejection is the R&D. Every landlord "no" became a rewritten pitch and a rebuttal, until the yeses came. Persistence isn't gritting your teeth; it's a feedback loop. Validate by selling, not by building in silence.

2. Focus is a system, not a feeling. Two company objectives per quarter, one North Star metric. If a project doesn't ladder into them, it doesn't get worked on, however shiny.

3. Build sustainably from day one. Validate on the smallest possible scale with minimal tech investment, prove the problem and market are big enough, and design for profitability early; it de-risks everything that comes after. And it applies to you too: Hannah calls out the sleep-under-the-desk myth. Sprints are real; burnout kills businesses. 

💬 Hannah has a question for you , see the pinned comment and tell us your answer. Guest: Hannah Chappatte LinkedIn: Hannah Chappatte | HYBR: https://hybr.co.uk Socials: @hybr.uk on TikTok, Instagram and X Hosted by Ollie Tiramuragan Collard and Dr. Becky Sage. 

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Surviving crisis - from a Beirut hostage ordeal to losing every client overnight. Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/founded. Application times may vary. Rates may vary. 

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They bought an office in lockdown when nobody else was buying. Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/founded. Application times may vary. Rates may vary.

Two mates met on a rugby pitch, became accountant and client, then bought an office building in the middle of lockdown, when no one else was buying.

In this episode, Ollie speaks to Rhys Jones (The Online Accountant) and Olly Ladbrooke (Moose Studios), business partners behind the Bristol Office Hub, about going from corporate life to running multiple businesses side by side.

They get honest about the mindset shift from employee to serial entrepreneur, the brutal moment a down-valuation left them scraping to fund a leaking roof, why complementary skills beat codified roles, and how community and referrals (not contrived networking) quietly built everything. Plus, we explore AI in accountancy and marketing, and why "just show up and take action" still wins.

Whether you're a solo founder feeling the isolation or weighing up a big risk, this one's for you.

LISTENER TAKEAWAYS

1. Resilience isn't a trait; it's a position. Their first building ran "like a dream", which is exactly what gave them the confidence and cushion to survive a brutal down-valuation on the second.

2. Cash buys you calm. Build six to twelve months of runway in the first two years, keep it lean, and you stop pouring energy into chasing bills instead of growing.

3. Action beats overthinking. No scaremongering about AI, these business partners just show up, make the call, and move forward. 90% of success is being there and taking the next step.

GUESTS

Rhys Jones, accountant and co-founder of The Online Accountant and The Property Accountant. Left corporate life to go solo, took on Olly as client number one, now runs a six-person practice.

Olly Ladbrooke, chartered surveyor (ex-BNP Paribas) and founder of Moose Studios, a marketing agency with offices in Bristol and London. Together they own and run the Bristol Office Hub.

Bristol Office Hub — bristolofficehub.co.uk (195–197 Whiteladies Road, Bristol)

Moose Studios - moosestudios.co.uk

The Online Accountant - theonlineaccountant.com

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Is software dead, or just being rebuilt? Ollie spent two weeks obsessing over Claude Cowork and turned 100 episodes of Founded & Grounded into a content engine. Becky spoke alongside the legendary Steve Blank.

We break down agentic AI, SaaS valuations, customer development, pricing as conversation, and why human connection is the moat that AI cannot copy. This will leave you wanting to experiment right now. 

Key takeaways

- Pricing is a conversation, not a number. Steve Blank's lesson is simple. Ask the customer the question, listen to the answer, then build the proposal. Skip that step, and you're guessing with someone else's money.

- AI raises the floor on output. It does nothing for trust. The founders who win the next cycle are the ones in rooms without laptops, building relationships that agents cannot fake.

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How do founders navigate a business landscape shaped by volatility, uncertainty, complexity and ambiguity?

In this live conversation, we speak with Matt Wilde from SWIG Finance about the funding gaps many businesses still face and what it really takes to grow in an unstable global environment. From working capital and supply chains to the role of trusted advisors and stronger ecosystem support, Matt shares what founders need to get right when the pressure is on.

Key takeaways:

We also explore the role of SWIG Finance as a social enterprise lender, supporting businesses with finance options that help founders start, sustain and scale. The conversation looks at the importance of good advisors, access to capital and stronger ecosystem connectivity, and how these factors shape a founder’s ability to build a resilient business.

Alongside this, we discuss the growing influence of AI on the way businesses operate. While technology can create efficiencies, Matt makes the case for keeping human judgment at the centre of decision-making.

The episode closes with real examples, reflections on smarter financial decisions and a broader look at what founders need to succeed in a VUCA world.

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7 billion views and counting: the growth secrets of Sidemen's creative mastermind, Jordan Schwarzenberger. 

Managing one of the world’s biggest creator collectives is no small feat. We dive deep with the man behind Arcade Media and the Sidemen’s explosive rise, blending sharp self-awareness, cultural intuition, and a bold approach to building in public. 

The creator economy is dead. Jordan reveals why relying on brand deals is outdated and how the Sidemen have built entire business models through strategic partnerships and leveraging their audience. This is a masterclass in staying relevant, building with intention, and growing without losing who you are.

Key takeaways

🔥 Know yourself to grow yourself. Jordan believes brutal self-awareness and personal branding are essential. When you understand who you truly are and fully embrace it, you unlock clarity, confidence, and business momentum. 

📹 Don’t just create. Document. It’s not just about creating content. Jordan shows how documenting your journey with purpose builds trust, drives growth, and keeps your brand aligned with your goals.

🤝 You can’t win alone.  Strategic partnerships are the key ingredient to scale. Find operators who complement your strengths and share your vision.

Have questions about this episode? Ask our hosts, chat now via our website

https://foundedandgrounded.com/episodes/lqtT800N1V6

Hit play and discover how to build something that actually lasts.

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