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