BOLD Business Podcast
Hosted by BOLD Business
A strategy podcast for business leaders where host Jess Dewell interviews CEOs and experts on the mechanics of leadership, growth, and resilience.
This is a tactical interview show where a growth strategist talks to fellow business operators about the mechanics of leadership. Conversations skip high-level theory to dig into specific scenarios like a marketing campaign failing, building team trust, or translating a vision for the frontline. The host often shares her own frameworks and connects guest insights back to specific, practical business problems.
“Unlike purely inspirational business shows, this podcast focuses on the "how" with a peer-to-peer feel. The host acts as both an interviewer and a fellow strategist, often using her own consultancy, Red Direction, as a recurring case study and source of frameworks.”
Who hosts this show
Jess Dewell, a growth strategist and founder of the consultancy Red Direction, hosts this interview show for business leaders. She talks with CEOs and experts about refining skills in strategy, communication, and team management, focusing on real-world situations and actionable advice. The podcast emphasizes asking better questions and taking decisive action to handle challenges like cultural shifts, market changes, and strategic planning.
Credentials & credits
- Strategic Growth Consultant
- Managing Partner at Red Direction
- Business Advocate
Other ventures
- Red Direction (consultancy)
- Business Basecamp framework
- Present Retreat Guide
What kind of podcast
When new episodes drop
- 01Clarity, Fairness, and Care: The Secret to High Trust OrganizationsJun 23, 2026 · 42 min
- 02Productive Struggle and Joyful Leadership: Redefining Success in BusinessJun 17, 2026 · 46 min
- 03Surviving Algorithm Shifts: Clear Messaging and Smart AdvertisingJun 9, 2026 · 36 min
- 04Workplace Legal Issues Every Company Leader Needs to KnowJun 2, 2026 · 39 min
- 05The Business Evolution Roadmap: Bridging the Gap from Here to ThereJun 2, 2026 · 51 min
- 06The Business Evolution Roadmap: Bridging the Gap from Here to ThereMay 20, 2026 · 1h 01m
- 07Guiding Growth: How to Keep Your Team, Tech, and Strategy RelevantMay 19, 2026 · 41 min
- 08Scale and Pivot: How Hard Decisions Shape Business EvolutionApr 29, 2026 · 44 min
Notable episodes
- 01Clarity, Fairness, and Care: The Secret to High Trust Organizations
A deep dive into the operational impact of trust, featuring a discussion on 'trust elasticity' and how a leader's self-trust affects the entire organization.
- 02Productive Struggle and Joyful Leadership: Redefining Success in Business
Introduces the concept of 'productive struggle' and explores how leaders can use discomfort and collaboration to drive growth and avoid burnout.
- 03Surviving Algorithm Shifts: Clear Messaging and Smart Advertising
Provides a tactical look at modern marketing challenges, including localized ads and the impact of bots, arguing for a focus on clear messaging over chasing trends.
What you'll be asked on this show
Jess Dewell opens by introducing the guest and outlining 2-3 key themes for the listener to track. She often validates her own premise ("What's your take on...") or shares a personal "business instinct" to kick off a topic. She probes by asking for "one action" or "tips for when...", pushing for concrete advice. She frequently uses her own experiences (like hiking) as analogies and summarizes guest points to ensure understanding before moving on, creating a collaborative, peer-to-peer dialogue.
The show is primarily guest interviews, but includes occasional solo episodes or panel discussions with other advisors. Host Jess Dewell often pre-frames the conversation by outlining key takeaways for the listener. She uses her own business, Red Direction, as a recurring case study and sponsor for its own products.
Questions BOLD Business keeps coming back to
12 cataloguedIf you're going on this show as a guest, expect some version of each of these. Each note explains when BOLD Business reaches for it.
leadership
1- Q.01
“What's your first reaction to [a common leadership scenario]?”
An opening question used to get the guest's immediate, unfiltered take on a relatable business situation.
advice
2- Q.01
“What's one action a company can take to [achieve a specific goal]?”
This question distills a complex topic into a single, practical takeaway for the audience.
- Q.02
“What are your tips for when [a common crisis] happens?”
A way to elicit practical, crisis-response advice for a common business challenge.
industry
1- Q.01
“Why is [a core principle] more important today than it was a few years ago?”
Challenges guests to defend the relevance of foundational business practices against current trends.
mindset
1- Q.01
“When assessing [an abstract concept like trust], does it start in the gut or are there other things to do?”
Explores the balance between intuition and structured process in leadership decision-making.
process
3- Q.01
“How can a team translate [a big vision] into language they'll receive well?”
Focuses on the practical execution and communication of high-level strategy.
- Q.02
“How do you identify the opportunity for an immediate reset to get back to neutral?”
Seeks to uncover a guest's process for course-correction during a struggle.
- Q.03
“How often are you able to schedule time for deep work right now?”
Probes into the personal productivity and reflection habits of successful leaders.
craft
2- Q.01
“What's the opportunity for a mid-market company to [achieve a specific outcome]?”
Tailors the conversation to a specific, and often-mentioned, segment of her audience.
- Q.02
“What are the key elements of an extraordinary customer experience today?”
Asks guests to define a core business concept in the context of the current market.
personal
1- Q.01
“Do you have a physical activity, like my hiking, that gives you feedback on your state?”
A signature question that connects a guest's personal habits to their professional effectiveness.
backstory
1- Q.01
“Did you ever see [a family member] hit a plateau and figure out how to get through it?”
Uses a personal, relatable angle to explore themes of growth and resilience.
Signature segments
- · Business Instinct framing
- · Present Retreat Guide promotion
- · Business Basecamp framework
- · Panel discussions with other advisors
- · Solo episodes by the host
Topics covered repeatedly
Who gets booked here
Guests are typically C-suite executives (CEOs, Presidents), partners at professional firms, or subject matter experts in areas like marketing, law, and leadership development.
- Kim Bohron Clarity, Fairness, and Care: The Secret to High Trust Organizations
- Dr. Jennifer Berryon Productive Struggle and Joyful Leadership: Redefining Success in Business
- Rihab Abouzakion Surviving Algorithm Shifts: Clear Messaging and Smart Advertising
- Jesse Weinsteinon Workplace Legal Issues Every Company Leader Needs to Know
- Christy Maxfieldon The Business Evolution Roadmap: Bridging the Gap from Here to There
- Dean Bartaon The Business Evolution Roadmap: Bridging the Gap from Here to There
Where to find this show
Audience & reach
The podcast is self-sponsored by the host's own consultancy, Red Direction. It promotes specific products and frameworks like the "Present Retreat Guide" and "Business Basecamp," positioning the show as a lead generator for her strategic services.
Subscriber and view counts are pulled live from YouTube and re-verified on a 30-day cycle. Listener estimates for the RSS feed aren't published here unless they're host-verified.
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People also ask
- Who is the host of the BOLD Business Podcast?
- The host is Jess Dewell, a Strategic Growth Consultant and the Managing Partner of the consultancy Red Direction.
- What is the format of the show?
- It's primarily an interview show featuring CEOs and business experts, but also includes occasional solo episodes from the host or panel discussions with other advisors.
- Is the podcast still running?
- Yes, the podcast appears to release new episodes on a weekly basis.
- What is Red Direction?
- Red Direction is the host's business growth strategy consultancy, which is frequently mentioned and promoted on the podcast.
- Who is this podcast for?
- It's designed for experienced business leaders, owners, and managers, particularly in mid-market companies, who are looking for practical advice on strategy, leadership, and operations.
- Where can I listen to the podcast?
- The podcast is available on YouTube, iHeartRadio, Apple Podcasts, and its official website, VoiceOfBoldBusiness.com.
Built from the show's public RSS feed, YouTube, the host's own websites, and the cited sources below. Computed and AI-extracted fields are labelled. Facts only — no private info, no fabrication, no transcripts republished.
Sources & how this page was built
This page is AI-assisted, grounded in the public sources cited below, and host-verifiable. We publish facts only; we do not republish transcripts. If anything here is wrong, the host can claim and correct the page above.Model: gemini-2.5-pro · high confidence
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