Dan Medley
Creative Operations
and Physical Problem Solving
I work where plans meet reality - spaces, timelines, and expectations that leave no room for error.
For the last five years in New York City, I’ve helped residential, commercial, and institutional teams identify risks before execution, clarify unclear plans, and avoid costly missteps.I’m often brought in not because teams lack ideas, but because ideas tend to stall, distort, or fall apart once follow-through begins.
WHAT I HELP WITH
- Evaluating physical spaces and plans before work begins
- Identifying risks, weak points, and false assumptions
- Creating practical punch lists and execution paths
- Translating between creatives, managers, and trades
- Helping teams make decisions they can live with long-term
WHAT I PREVENT
Most problems don’t come from bad ideas. They come from breakdowns in follow-through. Instead of letting uncertainty turn into cost, delay, or rework, I help you see:- What will fail before it’s built
- What assumptions won’t hold up in real use
- What will get stuck, contested, or misunderstood during execution
SELECTED EXPERIENCE
LEGO · FAO Schwarz · T-Mobile · Roc Nation · Rudin Management · Central Park Tower · Nasty Gal · Mr. Beast
WHERE THIS FITS
This work is most useful for:
- Creative and media organizations
- Production teams building physical experiences
- Property owners and managers with complex spaces
- Design and architecture teams
- Institutions with aging or unconventional buildingsEspecially when timelines are tight and stakes are real.
HOW ENGAGEMENTS WORK
Some engagements are brief.
Some are ongoing.I’m typically brought in when judgment matters more than speed, and clarity matters more than force.I tend to be most useful after the idea stage, when plans need to survive real constraints, competing priorities, and incomplete information.If you’re unsure whether something will work the way it’s being imagined, that uncertainty is usually the right moment to involve me.
ADDITIONAL WORK
Some founders and small teams come to me not because of a single physical project, but because their business itself has become hard to think about.In those cases, I offer a focused systems and operations engagement called Second Business Brain, designed to help founders turn ideas, instincts, and chaos into clear, usable structure.→ Learn more about Second Business Brain
CONTACT
If you have a real problem and need a clear-headed second set of eyes, reach me at [email protected]
BACKGROUND
For the past decade, I have built and run a high-end handyman and general contracting company in New York City, supporting residential, commercial, and institutional environments where mistakes are visible, timelines matter, and people expect things to work.My role has often gone beyond execution. I am frequently brought in to assess situations that are unclear, overdesigned, or already drifting off course, and to help teams regain clarity before small issues become expensive ones.This work has included problem-solving and operational support for commercial and public-facing environments connected to organizations such as Lego, FAO Schwarz, T-Mobile, and Corcoran, as well as ongoing work with property managers, creative teams, and business owners responsible for complex spaces.What I am trusted for is judgment.I help people think through how ideas will function in the real world, how spaces will actually be used over time, and where plans are likely to fail if no one intervenes early. I translate between creative vision, physical reality, and operational constraints so decisions can be made calmly and responsibly.My background is hands-on, but my value is in foresight, communication, and restraint.If you’re unsure whether something will work the way it’s being imagined, that uncertainty is usually the right moment to bring me in.
A systems and operations partner for founders who love what they do but hate the chaos. The goal is to help businesses run with fewer decisions, clearer ownership, and less reliance on one person holding everything together.
Who This Is For
Second Business Brain is designed for:- Solo founders and small teams
- Creative or service-based businesses
- Owners with ideas, momentum, and revenue but no structure
- Companies with multiple people involved but no clear rules, ownership, or delegation
- Founders who feel like everything lives in their head
Common Problems
Most clients come in dealing with some version of the following:- Nothing is written down
- No SOPs or repeatable processes
- Constant interruptions and decision fatigue
- No clean handoff of work
- Business and personal life completely blended
- Growth feels harder instead of easier
Why This Works
Structure is not about control. It’s about freedom.- Every problem can be broken into simple, actionable steps
- Systems turn chaos into clarity
- Clear expectations make delegation possible
- Written processes reduce daily decision-making
- Structure allows the business to function without everything depending on one personI specialize in turning ideas, instincts, and tribal knowledge into practical systems that real people can actually follow.
Ways to Work Together
One-Off Systems Build (Project Based)Best for founders who want real structure, not ongoing meetings.
This engagement focuses on identifying broken or missing systems and building a clear first version that can be used, delegated, and repeated.Typical work includes:- Mapping workflows and responsibilities
- Creating simple SOPs and documentation
- Clarifying ownership and handoffs
- Identifying gaps and failure points
- Designing practical systems that fit how the business actually operatesWork happens in defined blocks over a set project window. Communication is asynchronous during the engagement, with thoughtful responses provided during scheduled work time.This engagement has a clear beginning and a clear end.----Ongoing Second Business Brain (Monthly Advisory)Best for founders who want a thinking partner without adding another hire.
This is a lighter, ongoing engagement focused on clarity, problem-solving, and system refinement as the business evolves.Includes:
- Asynchronous questions and context sharing
- One purposeful working session or call per month, as needed
- Review of ideas, systems, and decisions
- Help breaking complex problems into actionable stepsResponses are not real-time. Messages are reviewed and replied to during work blocks, typically within a couple of business days.The goal is steady improvement and reduced mental load, not dependency.
Communication & Availability
Communication is primarily asynchronous.Clients can leave questions, context, or materials in a shared space, and I respond during scheduled work blocks. This allows for more thoughtful, useful responses without constant interruptions.Real-time calls are used selectively when they serve a clear purpose. Standing weekly calls are avoided unless there’s a specific reason they add value.
Scope & Responsibility
My role is to design structure and help implement systems.I don’t manage day-to-day operations, motivate teams, or own outcomes if agreed-upon systems aren’t followed.The goal of this work is clarity and independence, not ongoing reliance.
How I Work
I work in focused blocks, not ongoing meetings.Most engagements start with a clear problem, followed by structured time to design and build a solution. That usually includes mapping workflows, defining responsibilities, and creating simple systems that can be reused and delegated.The goal is always clarity and independence, not ongoing dependence.
What I Don’t Do
To keep the work effective and focused, there are a few things I intentionally don’t take on:- Standing weekly calls without a clear purpose
- Day-to-day management or motivation
- Acting as an on-call problem solver
- Owning outcomes if agreed-upon systems aren’t followedThis approach keeps the work practical, efficient, and aligned with long-term results.