Lead essay

The Drumbeat Gap

How voters forget who Democrats are between elections

Between 2020 and 2025, right-wing organizations cut their off-cycle ad spending by 3 percent. Progressive organizations cut theirs by 75. The data behind the gap, and a framework for closing it.

Read the essay 18 min read5 figuresMay 2026

Writing

All essays

A series in four parts

Who Pays, Who Builds, Who Decides

What an acre pays, why the megaproject never pencils, how a neighborhood decides where its share goes, and a model a village board could adopt on a Tuesday night. With Jonathan Konkol and Rick Potestio.

Part oneWhich Acre Pays for the Pipes?The per-acre math every village board should know by heart: a 3.4-acre Oak Park block out-earns a 17.7-acre Walmart nine to one. Part twoWhy the Megaproject DiesFour Chicago megasites and the pattern they share: one parcel, one owner, one plan, and decades of nothing. Next door, small lots kept building. Part threeLet the Neighborhood Play the GameDynamic Density, the Irvington workshop, and why Chicago already has the map it would need. What it lacks is the number. Part fourThe PickupNeighborhood allocation, public land on ground leases, pre-approved plan catalogs, and a per-acre floor, welded into one model with Illinois precedents for every part.
Urban planning, Theory & philosophy The Pickup Neighborhood allocation, public land on ground leases, pre-approved plan catalogs, and a per-acre floor, welded into one model with Illinois precedents for every part. October 20267 min read4 figures Urban planning Which Acre Pays for the Pipes? The per-acre math every village board should know by heart: a 3.4-acre Oak Park block out-earns a 17.7-acre Walmart nine to one. October 20266 min read4 figures Urban planning Why the Megaproject Dies Four Chicago megasites and the pattern they share: one parcel, one owner, one plan, and decades of nothing. Next door, small lots kept building. October 20267 min read5 figures Urban planning Let the Neighborhood Play the Game Dynamic Density, the Irvington workshop, and why Chicago already has the map it would need. What it lacks is the number. October 20267 min read6 figures Campaigns, Politics The Drumbeat Gap Right-wing groups cut off-cycle ad spend by 3 percent. Progressive groups cut theirs by 75. The data behind the gap, and a framework for closing it. May 202618 min read5 figures Campaigns Why Local Campaigns Need Legislative Intelligence Most tracking tools are built for K Street. Down-ballot races need the same capability for a fraction of the cost. May 20266 min read

The practice

The essays are the thinking. This is the work. Strategy, paid media, and research for campaigns, advocacy organizations, and mission-driven groups. City council through Congress, and the coalitions in between.

Roughly twenty-five clients since 2019. About half came back for a second cycle.

How we work

Strategy

Campaign and advocacy plans, messaging, coalition building, and the honest read on where you actually stand.

Paid media

Digital, direct mail, phones, and peer-to-peer texting. Creative through optimization, run as one program.

Research

Audience work, landscape analysis, public data, and managed legislative tracking across the states and Congress.

"Despite significant fundraising constraints, their efficient digital advertising program and disciplined field operation delivered a higher voter-per-dollar return than campaigns with far larger budgets."
Eric Wilson, candidate for Congress, WI-03
"By strengthening relationships with key partners in the bipartisan bridge-building space and building a large-scale outreach program, they helped extend our partner network's reach by over 100,000 voters."
Bill Shireman, In This Together America
Miles Sisk

Miles Sisk
Founder, Cascading Strategies
Chicago, by way of Portland

Built by someone who has done the work.

I started Cascading Strategies because the organizations doing the most important work usually have the least strategic support. The county board candidate. The nonprofit tracking bills in three states. The coalition trying to reach a million voters on a fraction of the budget.

My background is field organizing, campaign management, and paid media, from city council races in the Pacific Northwest to congressional campaigns in the Midwest to national advocacy. Before that, real estate and a stint writing about how cities grow, which is why some of what you'll read here is about land and not elections.

I work directly with every client. You get me, and I bring in specialists when the work calls for it.

More about Miles