— Media & Conversations
Podcasts & Media
Conversations about chaos, complexity, and the science of leading in the real world.
Most leadership advice assumes the future can be predicted. In real organizations it rarely can. In these podcasts and interviews, Derek Wilder explores how to lead through chaos and complexity, so leaders can shape culture and help teams solve problems.
— Latest Interview
Your Worth Is Not Your Performance: The Leadership Lesson That Changed My Life
Derek Wilder and Shah Huzaifa talk through why tying your sense of worth to your performance quietly undermines both your leadership and your wellbeing — and what to build in its place.
— Past Episode
Why 5-Year Business Plans Fail: How to Thrive in Uncertainty
Derek Wilder breaks down why rigid five-year plans collapse under real-world uncertainty, and what leaders should build instead to stay adaptable when conditions shift.
— Past Episode
Your Business Isn't Broken. You're Trying to Control Chaos.
Most leadership struggles aren't a sign something's broken — they're a sign you're fighting the natural, chaotic behavior of a complex system instead of learning to work with it.
— Past Episode
“A Weather Pattern, Not a Machine” — Founder Talk with Derek Wilder
Derek joins Caleb Pedosiuk for a Founder Talk conversation on why five-year plans are delusional and why a business runs more like a weather pattern than a machine.
— Past Episode
The Butterfly in the Boardroom — Live Conversation
Derek Wilder joins Sunny Ray for a live conversation on helping leaders build teams that can solve problems before they land on their desk.
— Featured Episode
The Butterfly in the Boardroom — Book Summary & Key Ideas
Derek walks through the full framework of the book — from Edward Lorenz's butterfly effect to the five operating habits leaders can use to build businesses that thrive through chaos, not despite it.
— Invite Derek
Request Derek as a guest
Derek is available for podcast interviews, virtual panels, and media appearances. He is a prepared, punctual guest who sends a one-page brief before each conversation so hosts can shape the discussion around their audience.
Ideal fit
Founder & Operator Shows
Host: entrepreneurs, operators, business owners. Focus: chaos theory applied to real business challenges.
Strong fit
Leadership & Culture Podcasts
Host: executives, team leads, organizational leaders. Focus: culture, decision-making, organizational design.
Excellent fit
Science & Ideas Podcasts
Host: curious generalists, science communicators. Focus: chaos theory, complexity, systems thinking.
Very strong fit
Finance, Strategy & Operations
Host: CFOs, analysts, strategy professionals. Focus: planning, forecasting, decision architecture.
— For Podcast Hosts
What Derek brings to the conversation
Derek spent more than thirty years running Hallmark Homes, Inc. — one of the Midwest's largest homebuilding companies — through recessions, rapid growth and every kind of turbulence a real business encounters. He brings hard-won operational insight, genuine scientific curiosity, and the ability to make complex ideas immediately recognizable.
- Why conventional planning fails in complex, fast-moving organizations — and what to do instead.
- The science of sensitive dependence: why small decisions at founding set patterns that are nearly impossible to undo.
- How to read an organization's 'strange attractor' — the invisible pull that shapes culture.
- Building modular, resilient structures that can absorb failure without systemic collapse.
- Why the best leaders stop trying to eliminate uncertainty and start designing for it.
- Real stories from Hallmark Homes, Apollo 13, Toyota, SpaceX, LEGO, Netflix and Shackleton's Endurance.
— What's Covered
Key ideas from these conversations
- Why businesses behave like nonlinear, chaotic systems — not predictable machines
- The butterfly effect in business: how small early decisions create outsized outcomes
- Edward Lorenz, Mandelbrot fractals, and strange attractors — applied to organizational culture
- Grace Winters: the fictional thread that carries the book's emotional argument
- Why turbulence isn't a problem to eliminate — it's a condition to design for
- Moving from a control mindset to a navigation mindset as a leader
— The Framework
The five habits Derek discusses in every interview
A five-part operating system Derek calls 'designing for turbulence'.
- 01
Shorter planning horizons & rolling forecasts
- 02
Feedback loops that surface problems early
- 03
Reversible moves instead of giant one-way bets
- 04
Modular structure so one failure doesn't infect the whole
- 05
Nonlinear portfolio thinking
Many small bets, one or two outsized wins.
A business is not failing because it is messy.
It is messy because it is alive — and once leaders understand that, they can build companies that thrive through chaos rather than despite it.
— Pre-Interview Resource
Book summary for hosts & producers
A structured summary of The Butterfly in the Boardroom for podcast hosts, producers and journalists preparing for a conversation with Derek.
01
The central argument
Business behaves less like a predictable machine and more like a complex, nonlinear, chaotic system. Leaders should stop treating turbulence as a problem to eliminate and learn to design for it.
02
The narrative thread
Grace Winters, a former math teacher turned business owner, learns to move from a control mindset to a navigation mindset.
03
Real-world case studies
Apollo 13, Toyota's Andon cord, SpaceX, Amazon's two-pizza teams, LEGO, Netflix, Wells Fargo, Uber and Shackleton's Endurance.
04
The final message
Leaders do not need more certainty — they need a better relationship with uncertainty: tell the truth, expect surprise, treat errors as information, make smaller bets more often.
— Invite Derek
Invite Derek to your show
A one-page guest brief and a PDF book summary are available on request. Response within 48 hours.