In this second installment of the Free Game series, Rich and Kevin pull back the curtain on the communications and field operations that make or break a political campaign. From crafting a message that hits (and sticks), to building a data-driven ground game that actually turns out voters, this episode is a crash course in campaign mechanics—and a consultant-level education for free. With stories from Obama’s Iowa field operation to Bloomberg’s message meltdown, the Maroon Bison crew brings real receipts from the trail, complete with debate prep war stories, Chick-fil-A branding analogies, and a reminder that if your campaign doesn’t know its win number—you’re probably going to lose.

📍 (06:41) — Two Departments, One Mission: Communications & Field
Rich and Kevin explain why these two parts of a campaign must work in sync. Comms builds the message, field delivers it to voters—online, on the phones, and at the door. And if they’re not aligned? The whole campaign suffers.

📍 (10:35) — Who’s On Your Comms Team? Roles That Matter
They break down the communications hierarchy: director, press secretary, digital lead, creative director, and the all-important pollster. Messaging isn’t just writing good speeches—it’s science, branding, and strategy.

📍 (24:21) — Why Message Discipline Wins Elections
You may be tired of saying the same thing over and over, but voters need to hear it 13 times before it sticks. From Obama’s “community organizer” line to Trump’s MAGA branding, repetition = recognition.

📍 (34:27) — Field Game: Your Ground-and-Pound Strategy
A deep dive into voter ID, persuasion, and turnout—plus why the voter file is your Bible and your organizers better be building an army. The motto: organize yourself out of a job.

📍 (46:40) — Know Your Win Number—or You’re Toast
Rich and Kevin wrap up with a key principle: if your campaign doesn’t know how many votes it needs to win, you’re not serious. From contact rates to persuasion tracking, it's all about the numbers—and the numbers don’t lie.

🏆 Mamba Mentality Award
🐍 All the everyday candidates putting their names on the ballot and stepping into the arena. It takes guts to run.

🐍 And a special shoutout to Stew Cornelius, the behind-the-scenes MVP keeping the Maroon Bison team on point and ready for primetime.

In Part 2 of their deep-dive with strategist Jake Orvis, Rich and Kevin unpack the overlooked heart of modern campaigns: research, tracking, fundraising—and the politics of being a white dude in a Black campaign space. From tracking candidates with binoculars to dodging call time in the men’s room, this episode offers a behind-the-scenes look at campaign mechanics, racial dynamics in Southern politics, and why nobody really likes asking for money.

The trio blends real-world advice with hilarious personal stories—plus reflections on managing egos, getting cursed out at barbecues, and why campaign operatives are some of the closest people you’ll ever work with. It’s vulnerable, technical, and as always, Southern as hell.

📍(01:00) - The Research Game: Foyers, Memos & Receipts
Jake breaks down the vital role of political research—from digging up court records to vetting your own candidate before the opposition does. It’s about precision, receipts, and never mixing up “John Smith.”

📍(07:00) - Trackers, Camcorders & Binoculars
What happens when you’re the white intern who “looks Republican”? Jake tells the hilarious story of his first tracking gig (involving a canceled event and a parking garage stakeout), and how campaign surveillance has evolved in the TikTok era.

📍(18:30) - The Art of Call Time
No one likes it—but fundraising call time is the engine of modern campaigns. The crew discusses why it’s painful, who struggles with it the most, and why you'd better be ready to call your exes if you're serious about running.

📍(24:00) - Hardest Jobs on a Campaign
From body person to call time manager, the team explores the toughest campaign roles—the ones with all the responsibility and none of the power. Rich, Kevin, and Jake debate which position is the most grueling and underrated.

📍(31:00) - Race, Respect & Running in the South
Jake opens up about navigating race and privilege as a white campaign manager working for Black women candidates. They get real about the expectations, historical context, and the difference between “diversity” and empowerment.

🏆 Mamba Mentality Award
Campaign Body People win this week’s Mamba Mentality Award. These behind-the-scenes MVPs manage logistics, egos, schedules, and crisis control—often with no glory, no backup, and no sleep. Salute.

Rich and Kevin welcome longtime political staffer and campaign strategist Jacob Orvis. From his Statesboro, GA roots to campaign war rooms across Georgia, Jake shares his journey from intern to operative and the unexpected lessons learned along the way.

The trio reflects on grits and growth: how food built campaign families, how campaigns forge lifelong relationships, and how one Google Form changed Jacob’s life—both professionally and personally. It’s part origin story, part masterclass on political mentorship, and part roast—with cameos from Cory Booker etiquette fails, HBCU food spots, and one unforgettable Dogzilla hot dog incident.

📍(00:30) - Southern Hospitality & Campaign Meals
Why feeding your people matters—and how Rich’s tradition of buying lunch helped shape Jake’s approach to mentorship.

📍(09:00) - Statesboro Stories & Georgia Southern Rejections
Jake breaks down his hometown, growing up with two chemist parents, and how Morehouse shaded Georgia Southern’s "Harvard of the South" claim.

📍(21:00) - Finding Politics at Georgia Tech
Jake opens up about switching from pre-med to politics, discovering the field through college Dems, and accidentally dressing like Tom Cruise for a Cory Booker event.

📍(25:00) - Campaign Life & Learning by Doing
From interning at the Georgia Dems to working with Rich on major campaigns, Jake shares key lessons about persistence, execution, and learning on the fly.

📍(38:00) - Finding Love in the Field
How a campaign internship form led to meeting Maria, now his wife and professional partner—and why political life is often personal too.

🏆 Mamba Mentality Award
Jacob Orvis gets this week’s Mamba Mentality Award for his adaptability, hustle, and commitment to getting the job done—whether it's bodying a U.S. Senator or building spreadsheets in the trenches.

In episode 25, Rich and Kevin take listeners behind the curtain of what it really takes to win a political campaign—before the race even begins. Whether you're a first-time candidate or just curious about how the political machine works, this is a masterclass in early campaign strategy. From team structure and fundraising to political infrastructure and soft launches, the Maroon Bison boys break it all down. Oh—and there’s plenty of HBCU pride, jokes, and a little smoke for overpriced bookstore merch too.

📍 00:30 - HBCU Pride and the $250 Shirt Problem
Rich and Kevin reminisce about campus life, HBCU merch, and why Jordan Brand should sponsor every Black college. They also reflect on rising enrollment and the political climate that drives students back to Black institutions.

📍 13:24 - Early Campaign Moves for 2026
With the 2026 midterms around the corner, the duo lays out the political calendar and stresses that if you're just getting started now, you're already behind. Campaigns are won long before Election Day.

📍 19:53 - Building Your Campaign Team Like a Startup
From campaign managers to finance directors, they map out the essential hires and liken campaigns to scrappy startups with high burn rates and tight timelines. It’s not about your cousin—it’s about professionals who know the game.

📍 33:50 - Fundraising, Burn Rate & Donor Geography
They dive deep into donor strategy—why in-state support matters, how to manage optics around out-of-state funding, and why Twitter doesn’t translate to real votes. Spoiler: you can’t out-message a broke campaign.

📍 40:06 - Political Infrastructure and Soft Launch Tactics
Endorsements, party politics, grassroots groundwork—this is the inside game most folks overlook. Kevin and Rich explain why soft-launching your campaign at local events and radio shows can make all the difference by Election Day.

🏆 Mamba Mentality Award
No Mamba Award this episode. As Kevin mentioned, not every day is a championship day—even Kobe had rebuilding seasons. But the foundation is being laid, and part two of this campaign deep dive is on the way.

In this episode of the Southern Comfort Podcast, Rich and Kevin break down the escalating redistricting drama in Texas—a political chess move with national implications. Drawing historical context from the Voting Rights Act to their personal organizing roots, the Maroon Bison duo unpacks the GOP’s latest power grab, the Democratic pushback, and what’s at stake for Black and Brown communities. From busted quorum rules to gerrymandered maps and the failure of national Democratic leadership, this is a masterclass in political realness—Southern style.

📍02:11 - The Texas Redistricting Showdown
Rich and Kevin dive into Texas Republicans' mid-decade redistricting effort—an unprecedented move to maintain House control before the 2026 elections.

📍 08:30 - Texas Dems Flee the State
To block the GOP’s map, Texas Democrats flee to blue states like Illinois and New York, denying quorum and halting the legislative process.

📍 14:18 - Where Are National Democrats?
Frustration builds as Rich and Kevin call out the absence of national Democratic leaders. While state governors like Gavin Newsom and J.B. Pritzker show boldness, Congress remains silent and slow—despite looming threats to democracy.

📍20:38 - The Ghost of Shelby County
They reflect on the gutting of the Voting Rights Act in 2013 and its ongoing consequences.

📍 27:12 - Should Black ‘Safe’ Districts Still Exist? (27:12)
Kevin raises a tough question: Have majority-Black districts outlived their purpose?

🏆 Mamba Mentality Award

The Texas Democrats earn this week’s Mamba Mentality Award for their bold, strategic resistance. Fleeing the state to block an unjust redistricting plan shows real courage—and a deep commitment to protecting democracy, even at personal cost.

Rich and Kevin tap into the political moment as Congress heads into August recess. From the Democratic Party’s brand crisis to local leadership lessons, they unpack the credibility gap between voters and elected officials—and why the party must move from outrage to action. Through candid analysis and firsthand consulting wisdom, they call for bold messaging, practical policy, and deep grassroots engagement rooted in working-class realities. Whether it's Medicaid, tariffs, or crime, the message is clear: say what you're for, not just what you're against.

📍 01:23 - What Is August Recess (And Why It Matters)
Rich and Kevin break down how the August recess is a chance for Democrats to reconnect with constituents—but also how Republicans are using it to duck accountability over Jeffrey Epstein-related controversies.

📍 05:11 - Why the Democratic Brand Is in Crisis
A recent Wall Street Journal poll reveals that voters trust Republicans more on the economy—even when disapproving of Trump. Kevin and Rich explain why Democrats’ lack of a clear, compelling message is dragging down the party’s favorability.

📍 (10:51) The Case for Affordability as a Core Message
Kevin argues that Democrats need one central issue: affordability. He ties everything from healthcare to immigration to kitchen-table economics and calls for consistent messaging that speaks to everyday struggles.

📍 (28:28) What Mayors Can Teach National Democrats
Highlighting mayors like Randall Woodfin, Brandon Scott, Andre Dickens, and Karen Bass, the hosts explore how local leaders are winning by focusing on practical solutions and delivering measurable results—not talking points.

📍 (33:00) Southern Senate Shakeups and Ossoff’s Next Test
With Roy Cooper entering the North Carolina Senate race and Jon Ossoff stepping into a solo spotlight in Georgia, the episode explores how regional politics could reshape national outcomes—if Democrats get serious about fielding full, diverse tickets.

🏆 Mamba Mentality Award

This week’s honors go to Coach Deion “Prime” Sanders for revealing his battle with—and victory over—bladder cancer. His strength, faith, and advocacy, especially for HBCUs, reflect a relentless spirit worthy of celebration.

A second salute goes to Governor Roy Cooper, who stepped into the 2026 Senate race not for glory, but to serve. His record of consistent wins in a red state and refusal to sit on the sidelines exemplifies political courage at its finest.

A virtual summer session brings Rich and Kevin together to unpack the cultural legacy and modern challenges of Black family reunions, reparations research debates, political disillusionment, and historical philosophies that still echo today. From grassroots fundraising to federal policy, they reflect on how far we've come—and how far we still need to go.

📍 00:36 – Family Reunions and the Nuance of Kinship
Rich and Kevin reminisce about week-long reunions, fish fries, and talent shows—then explore how COVID, cost, and cultural shifts have caused traditions to fade.

📍 09:21 – Reparations: From HR 40 to Wes Moore’s Veto
The hosts analyze the renewed fight for reparations, including Maryland’s controversial decision to veto a reparations study and what that reveals about political courage.

📍 21:11 – Booker T. vs. Du Bois: Echoes in Killer Mike
The historic tension between accommodation and resistance resurfaces through Killer Mike’s advocacy for trades—showing that the same philosophical rift still shapes Black progress today.

📍 26:28 – Why Misinformation Still Wins Elections
From ICE raids to rural hospital closures, Rich and Kevin break down how race and misinformation manipulate voters into supporting policies that harm them.

📍 30:13 – The System Ain’t Broken, It’s Working As Designed
They argue that political gridlock isn't about a lack of solutions—it's about a lack of will. Real change may require investing in new voters instead of chasing the old.

🐍 Mamba Mentality Award

Malcolm-Jamal Warner - Rich and Kevin reflect on the cultural impact he had on Black families across generations and why his legacy feels personal to so many.

Rich and Kevin continue their conversation with Maria Andrade, diving deeper into immigration, coalition building, and representation in political consulting. From calling out lazy messaging in the Democratic Party to exposing the lack of diversity in press shops, this episode cuts through the noise. They unpack how misinformation harms communities, spotlight overlooked organizers, and end with laughs, marriage advice, and the politics of rainy-day ads.

📍 00:00 – Immigration Is Not Just a Brown Issue
Maria challenges the assumption that Latinos only care about immigration, urging campaigns to see voters as full people with full lives—not just single-issue checkboxes.

📍 03:01 – Branding, Messaging, and Media Power
Kevin and Maria critique the Democratic Party's tendency to rely on lazy, recycled talking points, especially when strategists don't reflect the communities they’re trying to reach.

📍 06:32 – Representation Beyond Optics
Maria shares her journey into consulting and the need for real leadership opportunities—not token hires—to shape meaningful strategy and change.

📍 13:19 – Protest Isn’t One Size Fits All
They explore what modern resistance looks like, from mass rallies to personal family sacrifices, and the emotional toll of always being “on” in activist spaces.

📍 18:31 – How Misinformation Fuels Division
Kevin lays out how misinformation widens the Black and Brown divide, and why reframing issues like immigration as economic concerns can strengthen coalitions.

📍 25:35 – Advice for the DNC Chair and First-Time Candidates
Maria urges new leaders to listen first and delegate often—and shares some wild stories from behind the scenes of campaign life.

🏆 Mamba Mentality Awards

🐍 Maria Andrade – For refusing to be a token, pushing for true leadership representation, and cutting through the noise with strategy and substance.
🐍 The Coalition Builders – For doing the work to bridge communities, correct lazy narratives, and fight disinformation with authenticity and truth.