16 episodes

What does it take to win?How do you become a winner?Those are the questions we will answer with the help of America's top political operatives. No one knows what it takes to win cut throat fights like the people running campaigns. They give us their top lessons from both winning and losing.

The Cost of Winning Wesley Donehue

    • News
    • 5.0 • 3 Ratings

What does it take to win?How do you become a winner?Those are the questions we will answer with the help of America's top political operatives. No one knows what it takes to win cut throat fights like the people running campaigns. They give us their top lessons from both winning and losing.

    Winners Know How To Attack | Doug Stafford

    Winners Know How To Attack | Doug Stafford

    I’ve seen some stupid attacks in political campaigns. This one takes the cake. In 2010 Rand Paul was attacked for allegedly kidnapping a girl and making her worship his God, AquaBuddah. Yeah, that really happened. Obviously it backfired. 
    In this episode I chat with Senator Paul’s advisor, Doug Stafford. Doug Stafford is one of the best known general consultants in the Republican Party and a guy I really enjoy working with. He and I tackled Nancy Mace’s hot congressional race together in 2022.
    The lesson here is simple - winners know how to attack. Maybe don’t attack your opponent for worshipping a fake God.  It’s not very believable. 

    • 25 min
    Winners Build A Strong Foundation | Guy Short

    Winners Build A Strong Foundation | Guy Short

    Guy Short has been around the block enough times to see campaigns and businesses fail because they didn’t take the time to build a strong foundation in the beginning. We’re talking policies, procedures, structure and all the stuff that may not seem fun but are necessary for viability and sustainability. Winners know you have to get things right in the beginning. In this episode, Guy Short tells some fun stories from Michelle Bachmann’s 2012 campaign for President of the United States.
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    With over 25 years of experience advising and managing political campaigns, organizations, and parties at all levels of government, Guy Short serves as Chief Strategist for Campaign Solutions, now part of Push Digital Group.
    Guy has an extensive political résumé including serving as a chief of staff on Capitol Hill, senior advisor and national political director for a presidential campaign, and acting as principal fundraising and general consultant for several senatorial and congressional campaigns. Additionally, he has been a critical component in the success of many political causes, including numerous fundraising initiatives at the state and national level that set records for such projects.
    Guy has been a director of both national and state political action committees and has been elected as a national delegate to the last five Republican National Conventions from Colorado. Recently, Guy was elected to the 2012 RNC Platform Committee. He has been a member of the American Association of Political Consultants, Direct Marketing Association and is a board member of the National Right to Work Committee.
    A graduate of the University of California at Santa Barbara, Guy resides with his wife and two children in Erie, Colorado.

    • 31 min
    Winners Understand The Data | Mark Stephenson

    Winners Understand The Data | Mark Stephenson

    As tech innovations continue to change the world winners need to understand data if they want to win in the future. Georgia is becoming quite the swing state. It was ugly this year but not for Governor Kemp who easily won re-election. One reason he crushed it was his data operation that sliced and diced universes to deliver the right messages to the right people. That data operation was led by Mark Stephenson who joins us for this episode. We get real nerdy.  
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    Mark Stephenson is the Founder/CEO of Red Oak Strategic, an Alexandria, VA-based data science, analytics and targeting firm, and Amazon Web Services Consulting Partner.  Red Oak Strategic specializes in data science, data engineering, machine learning/AI, cloud consulting and strategy services, and for over 10 years, has worked with Fortune 50 companies, political campaigns and organizations on their data engineering, targeting and data analytics needs.  
    Mark has served as Head of Data & Analytics for a major 2016 American presidential campaign, is frequently called upon by national and local media for his data science insights and was called a top data scientist in 2015 by Wired Magazine.  In politics, Red Oak has worked with dozens of national committee, outside group, statewide and local campaign clients, and continues to be an innovative leader in the political analytics space. 
    Mark is also Co-Founder of Epidaurus Health, Inc., which is a software startup focused on automating and improving the prior authorization process in healthcare. Receiving their first patent in 2022, the company works on an improved data intake process, leveraging blockchain / smart contracts for security and data provenance and introducing machine learning to a complicated, cumbersome prior authorization process.

    • 29 min
    Winners Keep Their Foot On The Gas | Alex Garcia

    Winners Keep Their Foot On The Gas | Alex Garcia

    There are these humorous yet sad videos online of runners slowing down and celebrating a few yards out from the finish line only to be passed at the last second by someone who never let up. That happens in political campaigns too. A candidate has all the momentum and polls show them clearly in the lead. So they start relaxing only to be out hustled on the ground by a team putting in more time, making more phone calls and knocking on more doors. 

    Getting beat like that really sucks so don't let it happen. Run through the tape. In this episode Alex Garcia explains how he just eeked out a race by keeping his foot on the gas the entire time. Had he let up even a little bit he would have lost.
    Alex discovered his talent in grassroots campaigning nearly 12 years ago while serving as Deputy Campaign Manager in a State Senate campaign. Since then, he has served as chief of staff to sitting Lt. Governor Jeanette Nunez as well as many roles within the RPOF and RNC. He most recently served as the Regional Political Director of Florida. Today he serves as a Vice President at Push Digital Group.

    • 28 min
    Winners Find Creative Paths To Victory | Jordan Russell

    Winners Find Creative Paths To Victory | Jordan Russell

    A straight line may be the best way to connect two points but it’s not typically the path to victory. The winning strategy requires more creativity as the opposition moves, news pops and circumstances change.
    Today I’m joined by political operative Jordan Russell. Based out of Oxford, Mississippi, Jordan has worked as a senior staffer on Capitol Hill, presidential campaigns, and as campaign manager for US Senator Cindy Hyde Smith. He now serves as a senior strategist for political candidates at Push Digital.

    • 20 min
    Winners Don't Overplay Their Hand | Phil Bailey

    Winners Don't Overplay Their Hand | Phil Bailey

    Phil Bailey is one of my dearest friends and the head of our advocacy division at Laurens Group. He’s also our token Democrat 😀.  For years Phil and I had a weekly political podcast where we live-streamed (before it was cool) us talking to politicians over drinks in front of a live audience. We made national news a few times. Like when a state Senator decided to call Nikki Haley “a raghead” after a few bourbons and Budweisers. We briefly discuss that story here. 
    Phil and I weren’t always good friends. We met on the political battlefield when we went head to head a couple times in Aiken and Edgefield, SC. In this episode of The Cost if Winning Phil tells the story of how he overplayed his hand and accused the current SC Senate Majority Leader of being against the Lord’s Prayer. Smart people learn from their mistakes and Phil is one of the smartest operatives I know. He’s got a lot to teach you. Listen up. 

    • 27 min

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3 Ratings

BB in the Ville ,

A winning podcast

Whether you want to win in politics, business, parenting, or life, Wesley’s podcast is guaranteed to have something instructive to learn each show. Improve your odds of success. Hear great lessons from his guests and from the host. Follow this podcast.

Ian P. Hines ,

Absolutely Amazing

I’ve known Wesley for a decade, and if I had to describe him with one word, it would be “winner.” He’s more determined than anyone I know to do whatever it takes to cross the finish line first. His energy, enthusiasm, and authenticity make this podcast a must-listen for anyone who wants to be the best in politics or business.

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