Jordan Cracknell is a New York–born finance leader who worked on trading floors before moving to the UK for her MBA at Cambridge. Now a UK CEO in financial management, she’s passionate about helping more women see finance as a real, reachable option — and starting that confidence early through her children’s book You Can Count on Penny. She’s also a debut recording artist (yes, really), a step mum to three, and has had a front-row seat to UK politics through her husband, Olympic gold medallist James Cracknell.

Episode summary

Imagine calling 100 people to ask for an opportunity — and hearing “no” 99 times. Jordan Cracknell did exactly that to break further into finance, and what she learned goes way beyond job hunting: confidence is built by doing the uncomfortable thing, repeatedly. In this conversation, Jordan unpacks what it’s like to lead as a woman in a male-dominated industry, why “I’m just not a maths person” can quietly limit our choices for decades, and how families and schools can change the story for the next generation.

You’ll hear how Jordan’s early exposure to finance (including “take your daughters to work day” at the World Trade Center) shaped her, why she believes budgeting should be a basic life skill, and how her book You Can Count on Penny makes maths feel friendly and possible for kids. Plus: her unexpected leap into music, what she learned from UK election canvassing, and the phrases that keep her grounded when life gets tough.

What You’ll Learn

• How to build career momentum when you’re getting constant “no’s”

• Why money confidence is often a confidence issue, not an ability issue

• The hidden cost of believing “I’m terrible at maths”

• How early exposure makes intimidating careers feel within reach

• What women can do to explore finance careers without needing an “in”

• Why budgeting is a life skill — and how to start teaching it young

• What finance is actually like (and what Hollywood gets wrong)

• How to stay civil (even with a strong New York streak) while leading in the UK

• A simple, free first step to take control of your finances this week

Guest Picks

• Book: Liar’s Poker

• Music: Classical music (influenced by ballet training and counting rhythms)

• Tool/Framework: Excel (the backbone of finance — and a skill worth building)

• Quotes/Phrases: “This too shall pass.” / “In for a penny, in for a pound.”

Connect links

• Jordan’s book: You Can Count on Penny

• Jordan’s debut single + music video: “Gordon Gekko”

• Next release: “Park Avenue Princess” (releasing 20 February)

• Website: Jordan Cracknell

• Organisation mentioned: Women in Banking and Finance

About Leading BOLDLY

Connect with Matt: Linkedin

Connect with Jenny: Linkedin

Leading BOLDLY is the podcast for leaders, founders, and ambitious humans building real lives and real businesses — with honest conversations about confidence, capability, and doing what matters (even when it’s uncomfortable).

If this episode sparked something, share it with one woman (or teen) who needs a money-confidence boost — and grab You Can Count on Penny to...

Carolyn Hobdey is a multi-published author and leadership/culture change specialist known for naming the conversations workplaces avoid. She’s the voice behind The Midlife Mistress and author of All The Twats I Met Along The Way, De-Twat Your Life! and Redefining Selfish.

Episode Summary

Male allyship is usually framed as men supporting women. Carolyn flips the lens: what happens when men feel they can’t speak honestly at work, online, even at home, without being judged, mocked, or written off? Drawing on 25+ years in leadership, HR and transformation, she explores the growing mental load many men carry: the pressure to “say the right thing”, the fear of backlash, and the confusion of mixed messages around vulnerability and strength. Together, Jenny, Matt and Carolyn unpack why labels like “pick-me” can shut down important conversations, and how women can advocate for men without excusing harmful behaviour. The heart of this episode is simple (and powerful): curiosity, listening, and creating environments where humans can be nuanced—because culture only moves forward when everyone has a voice.

What You’ll Learn

• Why some men feel “there’s no safe way” to speak up, especially at work

• How the “pick-me” label can silence advocates (and what to do instead)

• The hidden cost of mixed messaging: “be vulnerable… but not like that”

• How to support men without amplifying harmful behaviour

• Why connection beats correction when culture is tense

• How leadership stereotypes still reward the wrong traits

• What “inclusive” looks like when men are included too

• A practical way to build healthier workplaces: Carolyn’s SIMPLE model

Guest Picks

• Book: The Five Dysfunctions of a Team — Patrick Lencioni

• Music: “Lost Without You” — Freya Ridings

• Quote: “Feminist is my second favourite F word.”

• Tool/Framework: The Chimp Paradox (mind management model)

• Also mentioned: Why Do So Many Incompetent Men Become Leaders? (And How to Fix It) — Tomas Chamorro-Premuzic

Connect with Carolyn

• Website: The Midlife Mistress https://www.carolynhobdey.com/about-carolyn-hobdey/

• All The Twats I Met Along The Way (book)

• De-Twat Your Life! (book)

• LinkedIn: Carolyn Hobdey https://www.linkedin.com/in/carolynhobdey/

About Leading BOLDLY

Leading BOLDLY is the podcast for SME leaders, founders, and entrepreneurs who want practical strategies and real conversations that build bold brands and strong teams—hosted by Jenny Jarvis and Matt Clutterham of Q Branch.

https://www.qbranch.consulting/

https://www.linkedin.com/in/jenny-jarvis/

https://www.linkedin.com/in/mattclutterham/

We talk about all we have learned about Leadership, the highs of wedding planning and the lows of clients who don't pay.

Events this year:

Clarity that Closes 1 Day Live - London

Clarity that Closes 1 Day Live - East Midlands

Clarity that Closes 1 Day Live - Online

Mission Accelerator Live

Productivity App: Productivity Power Up

Fusion Score: Take the Quiz

Book:

The Bridge Across Forever By Richard Bach

$100M Money Models - Alex Hormozi

Unreasonable Hospitality: The Remarkable Power of Giving People More Than They Expect by Will Guidara

Music:

Defying Gravity - Matt Copley

Say It - Stella Cole

Pure Imagination - Wonka

Kevin Crawford grew up inside his dad’s architecture practice in Montrose, starting on the photocopier at 14 and eventually leading the firm through a major transition to 100% employee ownership. Today he runs Designing Success, helping architecture practice owners reclaim time, build stronger teams and design businesses that support their lives, not the other way round.

Episode Summary

What happens when your family name is above the door, the business runs on your shoulders, and your body finally says “enough”? In this conversation, Kevin Crawford shares the inside story of growing up in a family architecture firm, feeling trapped by legacy and responsibility, and the back injury that forced him to stop working 24/7 and redesign everything.

Kevin unpacks how Crawford Architecture went from a traditional family-owned practice to a 100% employee-owned firm, why that decision protected both his dad’s legacy and his team’s future, and what it really takes to let go of control without walking away. He talks candidly about resentment, cashflow panic, missed family moments and the loneliness of being “the one” holding it all together – and the systems, mentors and mindset shifts that finally gave him freedom.

If you’re a founder, family business owner or practice leader who’s ever wondered how to share ownership, protect your health and still move forward boldly, this episode is for you.

What You’ll Learn

• How starting in a business at 14 shaped Kevin’s approach to leadership and legacy.
• Why “just work harder” stopped working – and the back injury that changed everything.
• The real emotional pressure of having your family name above the door.
• How to think about succession planning years before retirement, not at the last minute.
• What an Employee Ownership Trust actually is – and why Crawford chose 100% employee ownership.
• The shift from reactive firefighting to data-driven resourcing, revenue targets and one- and three-year plans.
• How founders can move from “doing everything” to building a team around their unique strengths.
• The role of mentors, retreats and communities in breaking the isolation of practice leadership.
• Why investing in your own health, wealth and self-development is a commercial decision, not a luxury.
• How AI, systems and the Pilotes app are helping practices win back 7–10 hours a week.

Memorable Lines

• “I thought the answer was to go in at 4am and leave at midnight. My back proved me wrong.”
• “For years I woke up thinking, ‘I don’t have time.’ Now my job is to design time.”
• “Succession isn’t ‘one day when I retire’ – it’s a strategy for everybody’s future, including your family’s.”
• “Owning 100% of the shares but 0% of your time is not freedom.”
• “You can’t market well if you don’t even know which projects are actually good for you.”

Guest Picks

• Books
• Traction – Gino Wickman
• Always Free: How to become financially free to live an inspired life – Jason Graystone
• Music
• “Caledonia” – the lyric “my way is clear and I know what I’ll do tomorrow” as a reminder to keep going with conviction.
• Tool / Framework
• Tiers of Freedom programme – Jason Graystone’s framework for financial, time and mental...

Most of us were taught more about test tubes than intimacy. In this conversation, Tatiana Ashborn shares how growing up scared of sex – and deeply under-served by traditional sex education – led her to start a sex and relationships podcast at just 17. What began as a lockdown project in her bedroom has grown into Dirty Talk, a show and social movement that now reaches millions, tackling everything from first-time stories and porn to shame, consent and long-term love.

Tatiana talks candidly about failing at school until she found the BRIT School, the power of creative education, and how her family backed her when she chose the most taboo topic of all. She lifts the lid on building a podcast as a business; sponsorships, algorithms, burnout and why she became a certified sex educator to deepen her impact. At its heart, this is an episode about leadership: doing the work before you feel like an expert, sharing the messy middle in public, and turning curiosity into a bold, culture-shifting career.

What You’ll Learn

• Why so many people leave school scared of sex, not prepared for it – and what’s missing from traditional sex education.
• How Tatiana went from struggling in an academic school to thriving at the BRIT School by learning in a way that suited her creatively.
• The real story behind starting Dirty Talk at 17 – including imposter syndrome, “learning in public” and being the opposite of an expert at first.
• Tactics she used to launch: pilot episodes with family, low-budget setups, and using lockdown as a creative sandbox.
• How Dirty Talk grew into a TikTok and podcast phenomenon, and what actually makes content shareable in a crowded space.
• The emotional weight of being “the sex person” publicly – and how she navigates boundaries, judgement and staying grounded.
• Why she chose to become a certified sex educator and how that changed the way she shows up for her audience.
• What younger audiences are actually asking about sex, relationships, porn and identity – beyond the headlines.
• How to turn a taboo topic into a platform for leadership, advocacy and real-world change.

Guest Picks

• Book: How to Win Friends and Influence People – Dale Carnegie
• Music: “Someone Like You” – Adele
• Quote:
• “Screw it, let’s do it.” – Richard Branson
• “You’re only given one little spark of madness and you mustn’t lose it.” – Robin Williams
• Tool / Framework:
• A ruthlessly used calendar and handwritten lists – planning everything out on paper so the creative chaos has structure.

Connect with Tatiana & Dirty Talk

• Tatiana’s site: https://www.tatianaashborn.co.uk/
• Dirty Talk website & episodes: https://dirtytalkofficial.com/
• Dirty Talk Instagram: https://www.instagram.com/tatianaashborn_/
• Dirty Talk TikTok: https://www.tiktok.com/@tatianaashborn_?_r=1&_t=ZN-91hPemnRNSw
• Under The Sheets with Tatiana Ashborn and Friends (podcast): Available on Apple Podcasts, Spotify and major platforms.

About Leading BOLDLY

The Leading BOLDLY Podcast is where SME leaders, founders, and entrepreneurs

sharpen their edge—and tell the

What if your phone served your life — not the other way around? Techless founder Chris Kaspar joins Matt and Jenny to unpack the thinking behind WisePhone 2 (a healthy, tool-only smartphone OS) and Sage, a UK kids’ iPhone with deep, multi-layered protections “safe out of the box”. We trace Chris’s journey from brand and filmmaking into mission-driven hardware/software, why he believes phones are “broken at the philosophy level”, and how dignity (not “kiddie” design) is the secret to teen adoption. We also get candid on fundraising, pricing pivots, and launching Sage in London — including an intimate, press-packed event at the Tate Modern. Expect practical strategies for parents, principles for leaders building humane tech, and a refreshingly honest look at the grind behind a purpose-led scale-up.

What You’ll Learn

· Why the philosophy behind mainstream smartphones (not the chips) drives unhealthy behaviour — and how to counter it.

· The shift from minimal (8 built-in apps) to healthy (approved third-party tools, no social/games/explicit).

· How Sage keeps teens’ dignity (iPhone UX, rebellious brand) so they’ll actually use it.

· Why parental controls alone fail — and what “final-layer” protection looks like.

· How to handle FOMO: creating small “opt-out” friend circles to tip culture.

· Inside a lean, relationship-first UK launch at Tate Modern (and why the UK is ready).

· Building with brand and ethos over patents — and why that’s the real moat.

Practical Plays You Can Use Tomorrow

· Audit the defaults: Turn off non-essential notifications; delete one addictive app; set greyscale at night. (Defaults aren’t designed for you.)

· Create a family phone plan: Choose tool-only apps (maps, banking, transport), no social/games; trial it for 30 days.

· Beat FOMO in a group: Agree a four-friend no-socials pact for a month; meet IRL weekly.

· If you’re shipping product: Launch humbly; optimise pricing with real-market feedback; iterate in public.

Memorable Lines

· “The defaults aren’t for you — they’re for advertisers and investors.” 【

· “Phones aren’t broken at the hardware level — they’re broken at the philosophy level.”

· “Kids don’t want kids’ phones. Dignity is the secret.”

· “Take initiative. Do ten things, fix the three that miss.”

Guest Picks

· Book: Positioning by Al Ries & Jack Trout and Warfighting by A.M. Gray

· Music/App: Suno (prompt-based music creation)

· Tool/Framework: EOS (Entrepreneurial Operating System) for lightweight, company-wide...

From Tech CEO to Stay-at-Home Dad: Powering Practical Allyship

Guest: Lee Chambers — award-winning business psychologist, author of Momentum, and founder of Male Allies UK. He’s worked with brands like UBS, IKEA and Oracle, and is recognised for making allyship practical, well-being strategic and inclusion something people feel, not just hear.

Episode Summary

Lee Chambers’ story bends every stereotype. He grew up in Bolton, the first in his extended family to attend university, dropped out during a mental health wobble, returned to graduate, and saw his graduate banking role collapse in the 2008 crisis — prompting him to build a fast-growing e-commerce company from a spare room. He later lost the ability to walk and learned to walk again, which reset his valuaes and ultimately led him to step away from the CEO seat to become a stay-at-home dad — a leadership masterclass in disguise. Listening to women at a local toddler group opened his eyes to everyday inequities at work and sparked his mission: help men build the skills of allyship and redesign systems so everyone belongs and performs. He now equips leaders and teams to move beyond slogans to evidence-based, everyday behaviours that compound into culture change.

What You’ll Learn

• What “allyship” really means: working effectively across difference, not grand gestures.
• Why inclusion fails without foundations — and how to build them.
• Tactics any leader can use to make meetings fairer (and more productive).
• How resilience, neurodiversity and identity can shape courageous leadership.
• The surprising leadership lessons of being a stay-at-home parent.
• Why men often hesitate to engage — and what helps them step in.
• How allyship improves retention, applications and survey scores.
• A first step any SME owner can take this week.

Practical Plays You Can Use Tomorrow

• Add a no-interruptions rule in meetings and nominate a rotating chair to enforce it.
• Ask three colleagues: “What’s it really like working here?” Listen, capture themes, act on one item.
• Audit one process (promotions, project allocation, networking invites) for hidden barriers; change one rule.
• Bring frontline voices (depots, logistics, ops) into inclusion design — not just head office.

Memorable Lines

• “Discomfort is where the growth is.”
• “Inclusion isn’t a plug-in; it’s foundations tied to real outcomes.”
• “Allyship isn’t a stunt; it’s micro-moments that add up.”
• “Your comfort zone is a padded jail cell.”

Guest Picks

• Book: Invisible Women — Caroline Criado Perez.
• Music: “Harvest for the World” — The Isley Brothers.
• Tool/Framework: The Boston Matrix (applied with modern nuance).

Connect with Lee Chambers

• LinkedIn: Lee Chambers
• Website: Lee Chambers
• Book: Momentum — leadership and change lessons for uncertain times....

In 2020, Audrey was falsely accused after a catastrophic motorway incident that led to her mother’s death. Eighteen months later, the case was dropped. She rebuilt—leaving a senior banking role, launching Smart Perspective, and shaping a practical, human approach to leading through crisis. This episode is about returning to work, redefining value, and starting again with intention.

Key Takeaways

• Returning after crisis: choose confidants intentionally; accept support without letting it define you.
• Redefine value: today’s recognition is about adaptability, communication and collaboration—not just deliverables.
• Lead in public: own mistakes, apologise if needed, don’t hide; save your energy for the people who matter.
• Boundaries: every “no” protects a better “yes”.
• Reinvention: it’s not all-or-nothing—blend what you keep with what you change.

Tool / Book / Music

• Framework (Tool): 3i Framework — Intention · Influence · Impact (clarify purpose, understand others’ context, land 1–3 key messages and one action).
• Book: The Answer Is a Question — on using inquiry to think and lead better.
• Music: “Panama” — The Avener (Audrey’s pre-session energy lift).

Memorable Quotes

• “Success is a team sport.”
• “People are immune to pain—be thoughtful about where you share yours.”
• “Every time you say no, you say yes to something else.”
• “Make values a destination, not a cage.”
• “You’re okay. Be you—for you.”

Connect with Audrey

LinkedIN

Website

Official Bio:

Audrey Daumain is an internationally recognised Executive Performance Coach and Corporate

Communication Strategist with over 20 years of leadership experience across finance, energy, and

luxury sectors. French-born and globally minded, she began her career in London’s financial district in

1998 before holding senior leadership roles at Barclays Private Bank, the National Bank of Abu Dhabi,

and Edmond de Rothschild.

In 2010, she founded Smart Perspective, a consultancy trusted by global leaders to navigate strategic

transformations with clarity, confidence, and candour. Audrey combines expertise in organisational

design, NLP, and Non-Violent Communication to create environments where leadership is human,

impactful, and sustainable.

Her personal journey—marked by resilience, trauma recovery, and thriving in male-dominated

industries—fuels her mission: to bring authenticity and humanity back to leadership

conversations. In April 2025, Audrey was recognised by Sarah, Duchess of York at the Women

Changing the World Awards for her work in transforming leadership cultures on a global scale.

Audrey is also a key contributor to the CLAFG Women Leadership Academy, a new program under

CLAFG (Centre de Liaison des Associations Féminines Genevoises)—Geneva’s umbrella network of

women’s associations. The Academy is piloting a leadership certification endorsed by FEDE (European

Federation of Schools), an international NGO with participatory status at the Council of Europe that

accredits educational programs...