Best Phillip Cloud Podcasts (2026)

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Controversy, conflicts & money magic 1:37:00

Play Pause

4h ago1:37:00

1:37:00

It's a long one today -- we've been off for a couple weeks and have a lot to catch up on! First, Omar talks through a few highlights of the upcoming Martin Luther King, Jr Day celebrations and activities around Madison. Then, Rob has an update from Sun Prairie, where the school district released the results of the investigation into the dean of stu…

1
Making Time: Fatherhood, Creativity, and the Long Game 23:59

9h ago23:59

23:59

In this episode, I’m returning to the mic after a long pause to talk honestly about life, creativity, and making time for the work that matters. Over the past year, a lot has changed — becoming a father, losing my dad, recalibrating priorities, and learning what it really means to create space instead of waiting for time. We talk about the long gam…

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Who Are Wisconsin Schools Really Working For? 55:44

18d ago55:44

55:44

This week on 365 Amplified, Rob Chappell, Omar Waheed, and Stephanie Díaz de León dig into Wisconsin's latest school district report cards and ask a hard question: who actually benefits from how schools are graded? The conversation explores racial achievement gaps, how DPI weights "economically disadvantaged" students, and why some districts can ea…

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The No Wax Cloud Dancer Edition 1:11:25

25d ago1:11:25

1:11:25

As promised after last week's grammar discussion, Rob talks through the etymology of the word "sincere" and Omar coins a new slang term. All that only after: We get updates on stories we've been following in the Sun Prairie Area School District and the Dane County Department of Human Services.' We look ahead to the CEOs of Tomorrow "Pitch and Launc…

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It's Bazaar & Gala Season 33:45

1M ago33:45

33:45

In this week's episode of 365 Amplified, the team dives into a busy stretch of community events, local politics, sports news, and a thoughtful conversation with the leaders of the Urban League of Greater Madison Young Professionals. Highlights Holiday Black Bazaar returns bigger than ever, featuring 50+ Black-owned vendors, performances, and commun…

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Will Rodney Rave be Wisconsin's first Native member of Congress? 25:24

1M ago25:24

25:24

On the podcast today, Rob talks through a few news items before chatting with Rodney Rave, who's running for Congress in Wisconsin's Third Congressional District, which covers most of Western Wisconsin. A former Ho-Chunk Nation legislator, Rave could become the first Indigenous person to represent the state in Washington. Today's episode is brought…

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What is community journalism? with Kynala Phillips 55:50

2M ago55:50

55:50

Rob's flying solo today, with a few news updates: a new Congressional candidate in western Wisconsin, an effort to support a beloved local musician who collapsed on stage after a heart attack last week, a recap of Madison College's first-ever trip to the national junior college men's soccer tournament, and a review of "Planets as Stars," the poetry…

1
A "cosmic romp" & local news controversy 1:11:33

2M ago1:11:33

1:11:33

On the podcast today, Rob, Stephanie and Omar talk through some local news, including a summit of Milwaukee social justice nonprofits, a snow removal apprenticeship program and the Madison College soccer team's first-ever trip to the national tournament. Then, poet and performer Gina Cornejo joins the show to preview her new production at Theatre L…

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From Help Desk to IT Leadership: Andrew Johnson's Journey 45:03

2M ago45:03

45:03

Andrew Johnson shares his journey in the IT field, starting from his early days in education to his current role in systems management. He emphasizes the importance of community, continuous learning, and the evolution of technology, particularly in relation to AI and automation. Andrew also discusses his experiences with user groups and conferences…

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A false news story, a response and what it all means 1:10:13

2M ago1:10:13

1:10:13

This week, News 3 Now published an erroneous news story about Madison-based nonprofit Urban Triage, and Madison365 was the only outlet to correct the record. On the podcast today, Rob, Nicholas and Omar talk through how that went down and what it means for the larger landscape of journalism and media. Plus, this weekend, Midwest Mujeres is hosting …

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FoodShare ends this weekend 44:16

2M ago44:16

44:16

Hosts: Rob Chappell, Stephanie Díaz de León, Omar Waheed Guest: Prenicia Clifton Episode Overview This week, the team covers the end of SNAP benefits and its impact on Wisconsin families and small businesses, the return of Madison Nonprofit Day, the growing threat of media capture, and a few lighter conversations to close the show — including consp…

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Pumpkins, politics & a rising Disney star 53:38

3M ago53:38

53:38

Hosts: Rob Chappell, Stephanie Díaz de León, and Omar Waheed Guest: Nate Buescher, UW–Madison freshman and star of Disney Channel's Electric Bloom Runtime: 53:38 On this week's podcast, we catch up on a range of news stories from the week, and get acquainted with a new neighbor who's a rising Disney star. 🌟 Leadership Summit Preview The eighth annu…

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From Paramedic to Redmond, Sean Bulger’s tech journey (Replay) 1:12:06

3M ago1:12:06

1:12:06

In this conversation, Sean Bulger shares his journey through the IT landscape, discussing his experiences as a consultant, the importance of a growth mindset, and the value of mentorship. He reflects on his diverse career path, that included jobs as a plumber and paramedic, and emphasizes the significance of community engagement and continuous lear…

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"Fascism aims to divide us:" a conversation with Francesca Hong 45:33

3M ago45:33

45:33

Rob and Omar kick off this week's 365 Amplified with stories making headlines across Madison365: Hmong New Year 50th Anniversary – A preview of this year's celebration marking 50 years since Hmong families began arriving in Wisconsin, emphasizing renewed connections with elders and cultural traditions. Indigenous Business Conference – Omar reports …

1
Code, Cloud & Confidence with Hailey Phillips (Replay) 1:06:46

3M ago1:06:46

1:06:46

In this episode, Hailey Phillips shares her journey from an HR internship to becoming a prominent figure in the IT industry. She discusses her passion for technology, the importance of automation and cloud computing, and the role of soft skills in tech. Hailey also reflects on her experiences in the gaming industry, her travels to Japan, and the si…

1
Madison's first woman-centered sports bar is coming soon 27:54

3M ago27:54

27:54

Two big stories to discuss on the podcast today: first, editor-in-chief David Dahmer joins the pod to preview the opening of Bernell's, Madison's first sports bar focused on women's sports. (Don't worry, they'll show the Packers too.) Then, Omar has a recap of the Sun Prairie Area School District, where voters passed a no-confidence motion against …

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Bryan Dam – Onesies, Sysadmin Life & Sneakernet Solutions (Replay) 1:11:20

3M ago1:11:20

1:11:20

By Fabian Rodriguez

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Madison College has a new president 40:11

3M ago40:11

40:11

On this week's 365 Amplified, Omar and Rob talk through a tense Common Council session on a new men's homeless shelter that ended in confrontations between alders and protesters. Then, we go over a change at the University of Wisconsin, where the Office of Human Resources has eliminated its Equity, Inclusion and Employee Wellbeing Department, and w…

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Matt Zaske’s Mustache Origin + Task Sequences in 2025 (Replay) 1:14:18

3M ago1:14:18

1:14:18

Matt Zaske, a seasoned sysadmin in higher ed, dives into device management, Windows 11 migration, and how his theater background shapes his IT communication. He shares his path into tech speaking, explores home automation, and showcases his passion for 3D printing and custom conference collectibles. We also learn the fun origin story of his iconic …

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The GenXPats 1:17:58

3M ago1:17:58

1:17:58

Today on 365 Amplified, Rob, Omar and Nick give an update on what we know -- and what we still don't know -- about who's been trying to enforce Madison parks rules with unhoused people on Madison's east side. Next, we've learned a lot about some disturbing allegations that led to the arrest of the Sun Prairie West High School Dean of Students on ch…

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"A Court of Resistance." Judicial candidate Huma Ahsan 57:13

4M ago57:13

57:13

In this week's episode of 365 Amplified, hosts Stephanie Díaz de León, Omar Waheed, and Rob Chappell dive into a wide range of local and national stories — from media censorship and free speech battles to community leadership and grassroots democracy — before welcoming a special guest. Featured Interview: Huma Ahsan Madison attorney Huma Ahsan, can…

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Helpdesk Scars & PowerShell Wins with Andrew Taylor 55:51

4M ago55:51

55:51

Andrew Taylor shares his journey from studying business to becoming a seasoned IT professional with over 20 years of experience. He discusses his early days in help desk support, his transition to end user computing, and the challenges he faced in various IT roles, including managing multiple tenants in the MSP world. Andrew emphasizes the importan…

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Affordability, Equity, and the Road to 2026: David Crowley Joins the Race 1:02:06

4M ago1:02:06

1:02:06

This week on 365 Amplified, the team dives into national, state, and local news—and sits down with Milwaukee County Executive David Crowley, who has just entered the race for governor of Wisconsin. Highlights from this episode: Political violence and rhetoric: The hosts discuss the recent assassination of Charlie Kirk, the responses from both the r…

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Writing, Teaching, and Defending: Ru Campbell’s IT Adventures 57:59

4M ago57:59

57:59

Ru Campbell shares his journey from starting in IT in 2012 to becoming a Microsoft 365 consultant and security expert. He discusses the importance of help desk experience, betting on oneself in career progression, and the transition to specializing in Microsoft Defender. Ru emphasizes the value of understanding security practices, the challenges of…

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The percolator incident 32:12

4M ago32:12

32:12

On this week's 365 Amplified: The Dane County Sheriff's Office is ramping up enforcement on school bus safety Milky Way Tech Hub is giving away laptops Urban Triage is hosting its Harvest Festival this weekend and the North Side Festival is coming next weekend Shaunte McCullum from the Northside Planning Council joins the show with more details on …

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From Packaging Apps to Podcasting with Rory Monaghan 53:03

4M ago53:03

53:03

Rory Monaghan shares his extensive journey in the IT field, starting from his early days in application packaging to his current role in end user computing. He discusses the evolution of application virtualization, particularly App-V, and its impact on organizations. Rory emphasizes the importance of community through user groups and the value of p…

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Fathers in Focus 28:39

4M ago28:39

28:39

On the podcast today, Rob, Nicholas and Omar get an update on the immigrant labor troubles in Monroe, and get a preview of the Wisconsin Badger volleyball season. Then, Joe Maldonado from UW Extension joins to preview the second annual Fathers in Focus confererence, coming up October 18. Read Omar's update on the Monroe dairy workers strike here. R…

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Building Better Reporting with Garth Jones 1:08:13

4M ago1:08:13

1:08:13

Garth Jones shares his extensive journey in the IT field, starting from his early days running a BBS to becoming a pivotal figure in endpoint management with SMS. He discusses the evolution of IT roles, the importance of proactive management, and the challenges he faced while building Enhansoft. Garth also reflects on his experiences with blogging,…

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MGFC just fired its only Black head coach 1:11:56

5M ago1:11:56

1:11:56

On this week's podcast, Stephanie, Omar and Rob dig into two big stories from this week's news: Workers in Monroe have walked off the job after W&W Dairy's new owners, Kansas City-based Dairy Farmers of America, is forcing employees to reverify documentation status. About 40 workers, most of whom have worked there more than 10 years, are asking for…

1
Networking, Fundamentals, and the Future of IT with Mattias Melkersen 47:09

5M ago47:09

47:09

In this conversation, Mattias Melkersen shares his journey from dropping out of school to becoming a successful IT consultant. He discusses the importance of mentorship, continuous learning, and the impact of AI on IT management. Mattias emphasizes the need for networking and community building in the IT field, as well as the significance of unders…

1
Art House 360 is open! 30:03

5M ago30:03

30:03

Art House 360, a multicultural community arts space in Verona, officially opened with a ribbon cutting this week, and will host a fundraiser tonight. So we are revisiting our conversation with cofounders Monica Cliff and AJ Juarez from last month about where the idea and inspiration came from, and what the space hopes to offer the community.…

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Pedaling Through IT Careers with Paul Winstanley 1:02:43

5M ago1:02:43

1:02:43

In this conversation, Paul Winstanley shares his journey in the IT industry, starting from his early days in retail IT support to specializing in endpoint management and becoming a community leader through blogging and speaking engagements. He discusses the importance of mentorship, the evolution of his career into consulting, and the impact of AI …

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A Constitutional crisis and a local recall 49:30

5M ago49:30

49:30

This week, Stephanie, Rob and Omar preview: Madison Black Restaurant Week Freedom Inc's Health Day Africa Fest Then, Rob reports on the event celebrating the 60th anniversary of the Voting Rights Act and why organizers say democracy remains under threat. Next up, the effort to recall a member of the DeForest Board of Trustees has successfully promp…

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From Dismantling a PC at 14 to Co-Founding a Tech Company with Jose Schenardie 1:07:02

5M ago1:07:02

1:07:02

In this conversation, Jose Schenardie shares his journey from starting his IT career in Brazil to becoming a co-founder of a cybersecurity company in Australia. He discusses the importance of niche conferences like MMS, the evolution of endpoint management with Intune and SCCM, and the role of AI in shaping the future of IT. Jose emphasizes the val…

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The Gov race is on. Who's in? 53:51

5M ago53:51

53:51

This week, Stephanie, Omar, Nicholas and Rob preview Dane Dances and give an update on the Village Board recall in DeForest -- including why it's important beyond the village. Then, Wisconsin Governor Tony Evers announced last week that he will not seek a third term, setting up the first election with no incumbent since 2010. The pundit class has b…

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Cloud Skills, Content Creation & Cardio – Andy Jones IT Journey 1:01:01

6M ago1:01:01

1:01:01

In this conversation, Andy Jones shares his extensive journey in the IT field, starting from his early days in web development to his current role focusing on cloud technologies and Intune. He discusses the importance of continuous learning, mentorship, and the evolution of technology, particularly AI and its implications for IT professionals. Andy…

1
Arts & Access 46:17

6M ago46:17

46:17

This week on 365 Amplified, Stephanie, Rob, Omar, and David dive into a packed episode featuring serious local issues, fun community events, and a deep look at a bold new arts initiative in Verona. 🧑‍⚕️ Janesville Nurses Strike Omar reports on the ongoing strike at Mercy Health East, where nurses are demanding a 7% raise, better health insurance, a…

1
Helpdesk to Consulting with Chris Cavazos on Shaping Tech Careers 51:18

6M ago51:18

51:18

In this conversation, Chris Cavazos shares his journey in the IT field, starting from his early experiences in the 90s to his current role as a principal consultant. He discusses the importance of mentorship, the transition from in-house IT to consulting, and the impact of Azure Virtual Desktop during the pandemic. Chris also touches on his persona…

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From Construction Sites to Configuration Profiles with Jóhannes Geir Kristjánsson 55:40

6M ago55:40

55:40

Johannes Geir Kristiansson shares his unique journey from a construction background to a successful career in IT, particularly in endpoint management and Intune. He discusses the challenges and rewards of transitioning from a hands-on trade to a more abstract field, emphasizing the importance of community and knowledge sharing. Johannes also reflec…

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Sunsetting DEI, switching sports & saving schools 1:02:47

6M ago1:02:47

1:02:47

This week on 365 Amplified, Stephanie rejoins the team for a packed episode featuring tough conversations about education, equity, and opportunity. 🎓 Sunsetting Diversity at UW? The team breaks down the University of Wisconsin's controversial decision to "sunset" the Division of Diversity, Equity & Educational Achievement (DDEEA). What does that me…

1
How Dustin Gullett Went from Mowing Lawns to Microsoft MVP 56:29

6M ago56:29

56:29

Dustin Gullit shares his journey from mowing lawns for a school district to becoming an IT consultant with a wealth of experience in military network security, healthcare IT, and MDM solutions. He discusses the evolution of Intune, the impact of AI on technology and daily life, and his passion for photography and blogging. Dustin emphasizes the imp…

1
Foraging, football & Fortify Fitness 54:46

6M ago54:46

54:46

This week on 365 Amplified, Rob Chappell, Omar Waheed, and Nicholas Garton cover a wide range of stories and conversations, from exploring the outdoors to diving deep into sports and fitness. Rob shares his experience at a foraging workshop with Color in the Outdoors, featuring Alexis Nikole Nelson, better known as @BlackForager, and author Sam Tha…

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How Nearly Becoming a Doctor Led to a Career in Cyber Security with Spencer Alessi 53:22

6M ago53:22

53:22

Spencer Alessi shares his journey from almost becoming a doctor to pivoting to IT, emphasizing the importance of help desk experience, mentorship, and continuous learning. He discusses his passion for systems administration, the significance of disaster recovery testing, and his transition into security. Spencer also reflects on his experiences in …

1
Wine & cupcakes! 24:46

7M ago24:46

24:46

Today, we announce the date and opening of registration for the eighth annual 365 Leadership Summit, the state's premier professional development, networking and community building event. Plus, we wrap up the sixth annual list of Wisconsin's Most Influential Asian American Leaders and share a bit of basketball news. Then, Rob Chappell visits Shakki…

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Naming OUs and Racing Bikes: The Balanced Life of Michael Escamilla 56:31

7M ago56:31

56:31

Michael Escamilla shares his journey in the IT field, discussing his experiences at conferences, his involvement with OSD Cloud, and the importance of community engagement. He reflects on his career path, the challenges faced in IT, and the significance of automation. Michael emphasizes the need for continuous learning and offers advice for aspirin…

1
Madison Black Restaurant Week is coming 34:24

7M ago34:24

34:24

This week, Rob Chappell brings you news and voices from the community while the rest of the team is scattered. Highlights include: 📰 Top Stories: The Center for Black Excellence and Culture announces it has raised all $31 million for construction—debt free! A Black Lives Matter sign at Crestwood Elementary is vandalized. The Girls State Soccer Tour…

1
Imposter Syndrome, Authorship, and Entrepreneurship with David Brook 57:08

7M ago57:08

57:08

David Brook shares his journey in the IT field, discussing his early experiences, the importance of apprenticeships, and the challenges of starting his own business. He emphasizes the value of community, public speaking, and the need for continuous learning in the fast-paced world of technology. David also opens up about his struggles with imposter…

1
Chuck Brown is dead 50:05

7M ago50:05

50:05

In this week's episode of 365 Amplified, the team dives into the Juneteenth celebrations happening around Dane County and across Wisconsin, previews summer opportunities with the Maydm youth STEM program, and spotlights Madison Night Mares softball team in their second season. Then, Rob is joined by Anna Gonzalez, Alys Dickerson, and Patty Heaston …

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From Paramedic to Redmond, Sean Bulger’s tech journey 1:12:06

7M ago1:12:06

1:12:06

In this conversation, Sean Bulger shares his journey through the IT landscape, discussing his experiences as a consultant, the importance of a growth mindset, and the value of mentorship. He reflects on his diverse career path, that included jobs as a plumber and paramedic, and emphasizes the significance of community engagement and continuous lear…

1
We Tell the News 32:06

7M ago32:06

32:06

This week, the 365 Amplified crew covers a range of timely and thought-provoking topics: 🏥 Meriter Nurses Win Contract Fight Omar recaps the surprising outcome of the Meriter nurses' five-day strike, which ended in a new contract featuring an 8% raise over two years and steps toward improved staffing ratios and safety accountability. 🏛️ Hospitals S…