How Not to be a Founder

An expat who bounced between the US and Europe, she built a career in advertising, then led customer-success launches at Magento (Adobe) and Meta’s Workplace.

A pregnancy conversation, a chance walk across Clapham Common, and a fear of derailed careers sparked Roleshare, a platform that matches two professionals to one senior role.

Sophie and her husband Dave:

• entered the London Business School Incubator,
• graduated from Techstars,
• raised two pre-seed/seed rounds,
• landed pilots with global enterprises…

…and then watched the market turn. Tech layoffs, frozen budgets, and the worst “future-of-work” funding quarter in five years forced them to wind down the company.

In the season-one finale, Sophie gets radically candid about:

• The spaghetti test – 300+ investor pitches, 40 deck rewrites, and the one question that tells you if they’ll wire.
• Timing vs. runway – why a genius idea still dies if you can’t fund the wait.
• Couple co-founders – the upside (shared empathy) and the very real family risk.
• Calling time – the data-driven moment she knew Rollshare had to close.
• Founder ≠ Unemployable – how the “kill-what-you-eat” mindset now makes her a better enterprise leader.
• The AI/no-code era: why today is the cheapest, scrappiest moment to test a startup.

Real talk on resilience, identity, and how to carry the win-loss lessons into your next role.

£80k in week one… then the VAT bill hit.

Paddy McCubbin walked away from a cushy director role to co-launch WeDo Group with two friends.

Day-three revenues smashed £80,000, but a four-month wait for a VAT number froze the cash, and an impulse order of 40 adjustable desks soaked up the runway.

In this episode, we unpack the un-Instagrammable side of a “rocket-ship” start-up:

• The Hacker–Hippie–Hustler trio – why three very different co-founders trump going solo.
• HMRC limbo – billing clients you can’t invoice and the domino effect on cash-flow.
• Buying mistakes – the stand-up-desk fiasco & other ego-driven purchases.
• Keeping momentum – rapid-fire idea testing (and killing) inside a recruitment scale-up.
• Fractional firepower – hiring a part-time CFO and CMO before you think you can afford them.
• Authentic brand – flip-flops in a CFO pitch, paddle-board meetings and why “fake it till you make it” kills trust.

If you’ve ever wondered what happens after the champagne-spraying LinkedIn post, this is the real balance sheet.

Listen in for hard numbers, hard lessons, and a reminder that the fires you fight are often the ones you lit yourself.

After 25 years at a recruitment desk, Jo Major never planned to start until the 2020 social justice wave, which exposed a training gap no one was filling.

She left a trade-body role, ran six free beta programmes, and launched a modular ED&I course that took off during the 2021 boom. Then budgets froze, partners drifted, and Jo had to reinvent everything, while ditching alcohol and hiring a mindset coach.

What you’ll hear:

• Why did she build the whole brand before writing a single invoice?

• The 6-client, no-fee beta that generated her first paid testimonials.

• Pivoting from 6-week courses to 2-hour workshops when L&D cash dried up.

• Killing the “your worth = last month’s billings” habit from agency life.

• Sobriety, strength-training and a coach who reframed confidence.

• The partnership that cost a new Ltd, website and trademarks—then fizzled.

• Final lesson: sell the idea first; build the slides only after someone buys.

A candid playbook on staying relevant when the hype cycle vanishes.

Keith Langbo never planned to be a founder.

He grew up watching his dad spend 50 years in one company, started his own career at Deloitte, then became employee #5 (and eventually president) of a high-growth recruitment start-up.

In 2012 he quit, moved 900 miles, and launched Kellica—bootstrapped, no investors, no salary for six years.

What you’ll hear:

• 721 coffees in six months – the networking sprint that funded his first hires.
• Fail-forward culture – why Jeff & Bill (his first bosses) celebrated mistakes.
• Founder ≠ CEO – the very different skills that take you from 0-5 M vs 50 M.
• Moving to London and starting over: 456 cups of tea, 1st UK hire, zero office rent.
• Hiring lessons: fire faster, fill your gaps, culture > résumé.
• The longest dry spell: six years without a paycheck and how he kept going.
• Final advice: “If you can’t survive me telling you don’t do it, you’re not ready.”

Real talk on risk, resilience and why the fast now eat the slow.

Claudia Green went from agoraphobic teen to boiler-room recruiter, then hit absolute rock bottom in 2019—job gone, relationship over, family illness.

Lying beside her sick grandma, she registered “Scaling Up,” a fractional talent & HR firm that now supports VC-backed start-ups across Europe.

In this episode, we cover:

• Why burnout + “nothing to lose” can be the best launchpad
• The two founder traits, Claudia says, predict low attrition and high output
• Agency-recruitment war stories (holes-in-shoes firings, anyone?)
• Her biggest founder mistake: kindness that crippled the team
• How to be both a decent human and an authoritarian leader—no, it’s not easy

Raw talk on resilience, people problems and paying maternity out of your pocket.

Two totally different routes, one very real destination: founder reality.

• Sydney de Arenas grew up around family businesses, quit a soul-crushing sales job at 23 and never looked back—until a bad hire in Paris almost wiped her out.
• Audrina went from pro Latin-ballroom dancer to VP at a performance-marketing startup—then a shock lay-off pushed her straight into Summit Chasers and, eventually, co-founding Hive with Sydney.

Together they unpack:

• The myth of the “glamorous” founder life—and why their bank balances said otherwise.
• Why early wins can be dangerous (including the car Audrina wishes she’d never bought).
• Sydney’s jaw-dropping investor meeting that turned into a personal-space assault—and how she rebuilt her fundraising strategy.
• A Guatemalan hostel “fridge scam,” tornado-dodging sales calls, and other moments you truly can’t make up.
• What not to do next: overspending, saying yes to every client, and building a company that can’t survive without you.

Raw, practical and occasionally ridiculous—exactly what this show is about.

Luke Davis went from “employee #31” at a fast-growing tech scale-up to co-founder of Diversifying.io, a job board tackling workplace diversity long before it was headline news.

In this conversation we cover:

• Bootstrapping in real life – why Luke still hasn’t taken VC money and how that forces “creative discipline.”
• Fund-raising vs. reality – the hoops a Black female-led team still has to jump through (including an invoice-financing deal that disintegrated the moment ID was requested).
• The $20,000 domain lesson – how ignoring the “.com” cost Luke’s team a chunk of runway.
• Life-threatening illness mid-startup – Luke’s colon-cancer battle, what it did to his mental health, and the power of therapy and marathon training in the aftermath.
• Why “hire another person” is not the default answer to every scaling problem.

If you’ve ever wondered what it really feels like to juggle growth, cash-flow panic and a health crisis—while the market mood swings on diversity—Luke lays it all out.

Ben Read joins Tom to explore the dynamic between visionary founders and the integrators who keep them grounded. From 10-ideas-a-week chaos to the reality of execution, this episode dives into what happens when startups lack the balance between bold thinking and operational discipline.

Ben reflects on the early risks, personal sacrifices, and what founders often get wrong when they try to go it alone.

If you’ve ever tried to build while flying blind, this one’s for you.

🎙️ Episode 00 – What How NOT to Be a Founder Is All About

Before we dive into the real stories, the mistakes, and the moments nobody posts on LinkedIn, I wanted to quickly share why I started How NOT to Be a Founder.

This podcast isn’t about the highlight reel. It’s about the real journey — the screwups, the pressure, the near-misses — and what actually shapes founders.

Because sometimes the best lessons aren’t in the wins. They’re in the stuff that almost broke you.

New episodes every week. First full interview drops 28th April.

🔔 Subscribe so you don’t miss an episode: https://www.youtube.com/@howNOTtobeafounder

📣 Follow along on Instagram: @how_not_to_be_a_founder

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