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Second in Command: A Veep Rewatch

Matt Walsh & Timothy Simons

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Join friends and Veep co-stars Matt Walsh and Timothy Simons for a weekly comedy podcast where they dive into a rewatch the Matt and Tim way -- beginning with the question, “what is memory? And is what we remember actually what happened?” They’ll also unpack the question “what’s it like to be two supporting actors on Veep as well as in their real lives in Hollywood.” So Veep fans feel free to ask your questions, leave your comments, and if you’re lucky, you may even win a free tuxedo. Expect ...
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Welcome to the “Second in Command” Podcast hosted by Cameron Herold, brought to you by the COO Alliance, where top-level COOs share their insights, tactics, and strategies that made them the Chief Behind the Chief. Cameron Herold founded the COO Alliance with one simple goal in mind: to provide COOs with the same professional development and growth opportunities CEOs have enjoyed for many years. COO Alliance is the world's leading network for the Second in Command. Cameron Herold is a top bu ...
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Podcaster and raconteur Van Lathan (Higher Learning, The Rewatchables) joins Matt and Tim to discuss the 1997 Luc Besson film, The Fifth Element. Tommy "Tiny" Lister Jr. plays President Lindberg, and that's not nearly the craziest thing in this movie. Presented in full and free for the holidays! Matt Walsh ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/mrma…
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What if the only way to build a company and a life with true resilience was to let everything break? Are you burned out, questioning leadership, or stuck in a plateau while everyone expects you to “scale perfectly”? In this episode, host Sivana Brewer sits down with Matt Rhodes, COO of The Phoenix Method and co-founder of Polaris Capital Investment…
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Ever feel like you’re stuck fixing fires instead of building teams that actually thrive? Imagine stepping into a legacy brand, mobilizing hundreds of operators, and transforming your culture from confused to unbeatable, all while modernizing for the future. In this episode, Cameron Herold gets real with Jackie Secor, COO of Taco John’s. She’s a 25-…
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Actor/TV Guide collector Patrick Fischler joins Matt and Tim to discuss the 1977 Alan J. Pakula film, All The President's Men starring Dustin Hoffman and Robert Redford. Richard Nixon is the President in archival footage. There's also some great David Lynch talk. Presented in full and free for the holidays! Matt Walsh ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instag…
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Ever wondered why so many remote teams fall apart while others scale to $100M and beyond… without burning out? This episode is a raw, practical look at exactly what it takes to build and lead a remote-first organization that actually works, not just in theory, but in the trenches. Cameron Herold sits down with Ryan Montgomery, COO of ClickFunnels, …
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Are you caught in the chaos of growth, struggling to build a team that actually wins together—not just on paper? In this unflinching episode, Sivana Brewer sits down with Christopher Wein, COO of Equiton Developments and a heavy-hitter in North American real estate, to crack open the mechanics of true team performance. Discover why chemistry, not j…
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To end 2025, we asked our patrons to tell us their favorite moments and episodes of the year. Here are their responses in episode form. For the rest of this conversation, go to ⁠⁠⁠https://patreon.com/secondincommand⁠⁠⁠ and become a patron! Matt Walsh ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/mrmattwalsh⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Timothy Simons ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠htt…
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Ever felt overwhelmed by relentless growth, leadership friction, or the challenge of building teams that actually scale? What if you could gain proven, insider strategies for multiplying operations by 20X while keeping chaos at bay? In this bold episode, Cameron Herold sits down with Harrison Crum, Chief Operating Officer of Ally Waste, to unpack t…
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Are you buried in the daily grind, afraid that missing one detail could wreck your team or business? Wondering how the best COOs stay energized, innovate, and avoid burnout while leading in a world that never slows down? This episode, guest host Sivana Brewer dives deep with Nick Dinsmoor, COO of Reel Axis, a fast-growing B2B marketing powerhouse. …
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Writer, director, producer, and improvisor Alex Fernie (Children's Hospital, Bajillion Dollar Propertie$, Convoy) joins Matt and Tim to discuss the 1996 Tim Burton film, Mars Attacks!, starring Jack Nicholson and Glenn Close. Jack Nicholson plays President Dale. For the rest of this conversation, go to ⁠⁠⁠https://patreon.com/secondincommand⁠⁠⁠ and …
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Ever wonder why most companies struggle to scale real culture as fast as they grow? What if the right blend of purpose, freedom, and radical alignment could make your team unstoppable? In this Fan Favorite episode, Cameron Herold sits down with Kshitij Minglani, co-founder of Mindvalley Quests and serial entrepreneur, to unpack the proven playbook …
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Ever felt overwhelmed by breakneck growth, scattered systems, and a CEO who just wants “more”—now? If you’re a second-in-command, this episode flips the pain of scaling upside down. Host Sivana Brewer dives deep with Inaas Arabi, COO at Block & Associates Realty and an industry veteran who’s engineered two rounds of company doubling (with a third o…
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In this episode of the Second in Command Podcast, co-host Sivana Brewer sits down with Richard Scheele, CFA, CFP, Managing Partner at Next Level Planning Group and former COO Alliance member. Richard takes us inside more than a decade of leadership evolution, from starting as an intern to stepping into the Managing Partner seat of a fast-growing fi…
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Comedian, writer, food show host, and podcaster Max Silvestri (I Love LA, Big Mouth, I Need You Guys) joins Matt and Tim to discuss the 2008 D.J. Caruso film, Eagle Eye, starring Shia LaBeouf. Madison Mason plays the President. Matt Walsh ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/mrmattwalsh⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Timothy Simons ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.ins…
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In this episode of the Second in Command Podcast, guest host Sivana Brewer sits down with Aldo Siciliano, COO and President of Watters International Realty, a fast-scaling residential brokerage serving multiple Texas markets. Aldo shares how Watters uses EOS (Entrepreneurial Operating System) to create alignment, simplify decision-making, and suppo…
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Comedian, actor, podcaster, and author Paul Scheer (The League, How Did This Get Made?) joins Matt and Tim to discuss the 1980 Richard Lester film, Superman II, starring Christopher Reeve, Gene Hackman, and Terence Stamp. The Richard Donner cut also gets discussed. E.G. Marshall plays The President. For the rest of this conversation, go to ⁠⁠⁠https…
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In this episode, Cameron sits down with Steven Huang, the Director of Finance, People, IT, and Community at MAPS, the Multidisciplinary Association for Psychedelic Studies. Steven helps lead global efforts to bring psychedelic research, policy reform, and public understanding into the mainstream, building on MAPS’ 40-year history at the forefront o…
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We’re bringing this episode back because listeners couldn’t get enough the first time around. Cameron sits down with Tom Keiser, COO of Zendesk, to unpack how he helped scale the SaaS powerhouse to a billion-dollar trajectory. Tom shares how he bridged the gap between IT and operations, built cadence-driven execution rhythms, and created visibility…
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In this episode, Cameron sits down with Brett Bruggeman, Executive Vice President and COO of Land O’Lakes, a 104-year-old, $16B cooperative spanning dairy foods, animal nutrition, and crop inputs. Brett shares how Land O’Lakes manages scale across 20 business units, supports more than 4,000 cooperative owners, and touches half of America’s farmland…
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Actors Carter Jenkins (Mad Men) and Romy Reiner (Curb Your Enthusiasm) join Matt and Tim to discuss our first TV movie, the 1998 Alex Zamm film, My Date With The President's Daughter, starring Will Friedle and Elizabeth Harnois. Dabney Coleman plays President Richmond. For the rest of this conversation, go to ⁠⁠⁠https://patreon.com/secondincommand⁠…
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In this episode of the Second in Command Podcast, guest host Sivana Brewer sits down with Matthew Rathje, Chief Operating Officer of TrueNorth Companies and long-time member of the COO Alliance. From starting in payroll and claims management to leading operations for a $165M insurance and professional services firm, Matt shares his journey of scali…
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Writer/Director/Raconteur Kevin Smith (Clerks, Mallrats, Dogma) joins Matt and Tim to sorta talk about the 1991 Oliver Stone film, JFK, starring Kevin Costner. President John F. Kennedy appears in archival footage, and the Zapruder film. Yeeps. For the rest of this conversation, go to ⁠⁠⁠https://patreon.com/secondincommand⁠⁠⁠ and become a patron! M…
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In this episode of the Second in Command Podcast, guest host Sivana Brewer sits down with Dr. Melonie Boone, Chief Operating Officer of Edesia Nutrition, a Rhode Island–based nonprofit on a mission to end childhood malnutrition worldwide. Dr. Boone shares her inspiring journey from corporate HR and executive consulting to joining a purpose-driven o…
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In this Fan Favorite episode of the Second in Command Podcast, Cameron Herold speaks with Anna Collins, President and COO of Bulletproof, the globally recognized brand behind Bulletproof Coffee, supplements, and biohacking products designed to help people perform better, think faster, and live healthier lives. She is also a Board Member of Ladies W…
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In this episode of the Second in Command Podcast, guest host Sivana Brewer sits down with Daniel Quinonez, Chief Operating Officer of the Plumbing-Heating-Cooling Contractors Association (PHCC) — one of the oldest trade associations in the United States, founded nearly 140 years ago. Daniel shares how this long-standing organization is transforming…
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Actor and writer Jon Glaser (Delocated, Late Night with Conan O'Brien) joins Matt and Tim to discuss the 1968 Franklin J. Schaffner film, Planet Of The Apes, starring Charleton Heston. James Whitmore plays the President of the Assembly (It counts!). Matt Walsh ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/mrmattwalsh⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Timothy Simons ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠…
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In this powerful episode of the Second in Command Podcast, co-host Sivana Brewer sits down with Brittany Dunn, COO and co-founder of Safe House Project, a national nonprofit dedicated to eradicating human trafficking in the United States. Brittany shares the remarkable story of how she and her co-founder built Safe House Project from an idea into a…
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In this episode of the Second in Command Podcast, co-host Sivana Brewer chats with Will Smith, COO and Managing Partner of Lone Star Pups, a multi-location Dogtopia franchise with 15 stores across San Antonio and Denver. Will shares how he’s scaled his team from zero to 140 employees in just a few years by leading with servant leadership, radical t…
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Actress and improvisor D'Arcy Carden (The Good Place, Nobody Wants This, Barry) joins Matt and Tim to discuss the 2004 Donald Petrie film, Welcome To The Mooseport, starring Ray Romano and Gene Hackman. Gene Hackman plays former President Monroe Cole. For the rest of this conversation, go to ⁠⁠⁠https://patreon.com/secondincommand⁠⁠⁠ and become a pa…
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In this episode of the Second in Command Podcast, Cameron Herold sits down with Ebert Grobler, COO and co-founder of Ruby Digital, one of South Africa’s top-ranked digital agencies now expanding across the globe. Ebert, who is a COO Alliance member, shares how his company has achieved near-perfect team retention and why their internal mantra—“Grow …
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In this episode of the Second in Command Podcast, guest co-host Sivana Brewer (Fractional COO for Remote Teams and former COO at Closers.io) sits down with Cory Raggi, COO of 1RDG The Financial Center, to talk about leading with empathy, navigating change, and building trust in teams both large and small. Cory shares her journey from leading HR at …
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Comedian, actress, and singer/songwriter Jackie Tohn (Nobody Wants This, G.L.O.W.) joins Matt and Tim to discuss the 2007 Jon Turtletaub film National Treasure: Book Of Secrets, starring Nicolas Cage. Bruce Greenwood plays The President and Glenn Beck (not that one!) plays Abraham Lincoln. For the rest of this conversation, go to ⁠⁠⁠https://patreon…
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In this Fan Favorite episode of the Second in Command Podcast, Cameron Herold sits down with Sarah Jones Simmer, former COO of Bumble, to explore how the company scaled from an empowering dating app into a billion-dollar global social platform redefining connection and kindness online. Sarah shares her journey from investment management to leading …
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In this episode of the Second in Command Podcast, Cameron Herold speaks with Brent Hagan, Chief Supply Chain Officer at Lob, a direct mail automation platform delivering billions of personalized mail pieces every year. Brent shares how he helped a 12-year-old startup kick off its “second act” by transforming complex logistics into scalable systems …
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Comedian, actress, and podcaster Kate Berlant (Once Upon A Time... In Hollywood, Dream Scenario, Berlant & Novak podcast) joins Matt and Tim to discuss the 2014 Greg Whiteley documentary, Mitt, about 2012 Presidential candidate Mitt Romney. For the rest of this conversation, go to ⁠⁠⁠https://patreon.com/secondincommand⁠⁠⁠ and become a patron! Matt …
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What does it take to help build one of the most influential e-commerce companies in the world? In this Fan Favorite episode, Cameron Herold sits down with Harley Finkelstein, President and COO of Shopify, to revisit one of the most downloaded and talked-about conversations in the show’s history. Harley shares his journey from law school student to …
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What really separates a COO who keeps the lights on from one who drives exponential growth? In this episode, Cameron sits down with Imad Jbara, COO of L2 Infinite Insurance and former COO of WoJo Media, who transformed a company’s client retention from 20% to 80% in just six months. Together, they unpack how COOs can build trust, fire with confiden…
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This Fan Favorite episode is a recast of one of our most impactful interviews, still packed with insights for second-in-command leaders. Whether it’s your first listen or a revisit, there’s timeless value inside. What does it take to scale a $100M company into a $365M powerhouse and beyond? In this episode, Cameron Herold sits down with longtime fr…
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In this episode of the Second in Command podcast, co-host Sivana Brewer is joined by Andrew Eisbrouch, COO of Abrams Media. During this fascinating conversation, Sivana and Andrew explore the unique journey of building and scaling businesses across multiple industries. You'll hear about the different challenges faced when moving from the early star…
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Actress and singer Beverly D'Angelo (Vacation, Entourage) joins Matt & Tim to discuss the 1993 Wolfgang Petersen film, In The Line Of Fire, starring Clint Eastwood, Rene Russo, and John Malkovich. Jim Curley plays the President. It doesn't matter. For the rest of this conversation, go to ⁠⁠https://patreon.com/secondincommand⁠⁠ and become a patron! …
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In today's episode of the Second in Command podcast, Cameron explores one of the most common yet challenging aspects of leadership: how to handle conflict without falling into the role of constant mediator. You'll hear strategies for equipping managers to address issues themselves, drawing from structured frameworks that encourage ownership, accoun…
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In this episode of the Second in Command podcast, Cameron is joined by Nick Malone, former COO of Sitecore and a seasoned executive with over 24 years of leadership experience in the IT sector. During this fascinating conversation, Cameron and Nick explore the complexities of driving growth in a rapidly evolving industry. You'll hear how leaders na…
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Actor and Emmy winner Lamorne Morris (New Girl, Fargo) joins Matt & Tim to discuss the 2012 Christopher Nolan film, The Dark Knight Rises, starring Christian Bale and Tom Hardy. William Devane plays an unnamed President. For the rest of this conversation, go to ⁠⁠https://patreon.com/secondincommand⁠⁠ and become a patron! Matt Walsh ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠http…
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Thinking about hiring a second in command? Getting it wrong can stall your growth, drain your energy, and wreck your culture. Getting it right can unlock scale, freedom, and balance. In this solo episode, Cameron Herold, founder of the COO Alliance and author of Second in Command, walks you through how to start the process of hiring a COO. He expla…
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In this episode of the Second in Command podcast, Cameron is joined by Andrew Rickett, Chief Operating Officer of Karmo, Australia’s largest car subscription provider. During this fascinating conversation, you'll hear how Andrew spent decades in a traditional industry before pivoting into a space that redefines consumer expectations. He shares insi…
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Comedian and actress Arden Myrin (The Righteous Gemstones, Will You Accept This Rose? podcast) joins Matt and Tim to discuss the 1982 John Huston film, Annie, starring Aileen Quinn and Albert Finney. Edward Herrmann plays President Franklin D. Roosevelt. For the rest of this conversation, go to ⁠⁠https://patreon.com/secondincommand⁠⁠ and become a p…
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In today's episode of the Second in Command podcast, Cameron discusses one of the most critical hires a business can make, a role that directly impacts leadership alignment, financial clarity, and long-term success: the Chief Financial Officer or CFO. The conversation highlights how small red flags during the hiring process, such as scheduling mish…
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In today's episode of the Second in Command podcast, co-host Sivana Brewer is joined by Sarah Harris, Fractional Chief Operating Officer at OMG Commerce. In this episode, you'll be taken behind the scenes of a dynamic leadership role that’s often misunderstood but critical to a company’s growth and health. Through candid stories and practical insig…
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Actress and comedian Caitlin Reilly (Loot, Hacks) joins Matt and Tim to discuss the 2004 Roland Emmerich film, The Day After Tomorrow, starring Dennis Quaid and Jake Gyllenhaal. Kenneth Welsh plays Vice President (VEEP) Becker. For the rest of this conversation, go to ⁠⁠https://patreon.com/secondincommand⁠⁠ and become a patron! Matt Walsh ⁠⁠⁠⁠⁠⁠⁠⁠⁠…
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