How did we get here? What’s with Holmes ‘stache? - Ruthless Q&A
Ruthless Podcast
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🎙️ We kick off our Christmas Day Q&A by answering the burning questions from the audience. We talk through how our careers actually started, how campaign instincts and comms muscle turn into real-world wins, and why the Progrum isn’t just “four guys with microphones,” but four guys who’ve lived the jobs we talk about.
⚡ Then, how the sausage gets made: how messages spread, why creativity beats policy-speak, and how the right phrase at the right moment can take over the conversation. We also talk about the early internet era in politics—how it worked, why it mattered, and what separated the serious operators from the scammy money-grab crowd.️
🥸 More of your questions in this proper holiday hang: Holmes’ on-again/off-again mustache situation, where ‘Progrum’ actually comes from, and whether we still have day jobs (we do). More Q&A in Part II - coming next week.
00:00 - Christmas Day Q&A - Our gift to you
04:16 - The backstory on the fellas
05:14 - How comms work actually gets learned in the Senate
11:12 - Selling stories to reporters and shaping the narrative
12:50 - Branding moments that stick in politics
17:30 - The road back to winning in 2014
24:58 - Building a real professional partnership
28:37 - Smug’s bio: finance to politics to operating in NYC
30:00 - Inside the financial crisis panic
35:52 - Where “Comfortably Smug” comes from and why it takes off
40:16 - Covid-era Zoom happy hours give birth to an idea
49:52 - Why does Holmes mustache come and go?
53:19 - Where “Grum/Progrum” comes from—dialects, sports, and Senate impressions
59:17 - Do we still have day jobs? What we actually do now
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