The Content Cocktail Hour

“Out-of-home marketing might be the most underrated B2B channel right now,” says Charlie Riley, Head of Marketing at OneScreen.ai

In this episode of The Content Cocktail Hour, host Jonathan Gandolf sits down with Charlie Riley to explore the creative resurgence of out-of-home (OOH) advertising—and why it’s becoming a powerful tool for modern marketers. From billboards and digital signage to guerrilla tactics and experiential stunts, Charlie shares real-world examples of brands breaking through the noise with memorable, measurable campaigns.



They dive into how OOH has evolved from guesswork to data-driven precision, what B2B marketers can learn from D2C, and why internal storytelling is just as critical as external messaging. Plus, Charlie offers sharp insights on the limits of marketing titles, the value of partners over vendors, and how small teams can make a big impact.

In this episode, you’ll learn:

1. How out-of-home fits into modern marketing, and what makes it measurable
2. Why internal marketing is often more critical than external campaigns
3. How to use data and instinct to find your ideal customer

Resources:

Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

Explore AudiencePlus: https://audienceplus.com

Connect with Charlie on LinkedIn: https://www.linkedin.com/in/charlieriley/

Explore OneScreen.ai: https://www.onescreen.ai

Timestamps:

(00:00) Intro

(01:27) Charlie’s path to marketing leadership

(03:15) Why out-of-home is more than just billboards

(05:30) Creative case studies and real-world OOH impact

(07:10) How OneScreen uses data to eliminate the guesswork

(10:45) The B2B vs D2C mindset shift

(14:15) Using out-of-home for ABM

(16:40) Storytelling with data

(19:00) Why marketing titles are often misleading

(21:10) Internal marketing is your hidden superpower

(23:30) Snorkeling vs. deep diving as a modern marketer

(25:00) How to partner with OneScreen

“Favor fit over fame for influencer marketing success,” says Vivien Garnès, co-CEO at Upfluence

In this episode of The Content Cocktail Hour, Vivien Garnès, co-founder and co-CEO of Upfluence, joins Jonathan Gandolf to unpack influencer marketing in the B2B and B2B2C space. Vivien shares why aligning your influencer’s audience with your brand matters more than follower counts, how influencer marketing has matured beyond vanity metrics to focus on real business impact, and why brands should give influencers creative freedom to unlock authentic engagement. She also opens up about her entrepreneurial journey launching Upfluence, how the co-CEO model works for her company, and an unpopular marketing opinion that changed their approach to ad spend.

In this episode, you’ll learn:

1. Why fit matters more than fame when choosing influencers
2. How to measure influencer marketing success beyond impressions and likes
3. The benefits and challenges of sharing creative control with influencers

Resources:

Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

Explore AudiencePlus: https://audienceplus.com

Connect with Vivien on LinkedIn: https://www.linkedin.com/in/vgarnes/?locale=en_US

Explore Upfluence: https://www.upfluence.com/

Timestamps:

(00:00) Intro

(00:06) Two schools of thought on B2B influencer marketing

(06:20) Favoring fit over fame in influencer partnerships

(09:00) Balancing editorial control and influencer freedom

(12:15) Tracking meaningful ROI in influencer marketing

(14:30) Vivien’s entrepreneurial beginnings and launching Upfluence

(18:00) How the co-CEO model works for Upfluence

(19:50) Branded ad campaigns and marketing assumptions

“Focus beats frenzy every time,” says Jason Hubbard, founder & CEO of DemandMagic

In this episode of The Content Cocktail Hour, Jason Hubbard, founder & CEO of DemandMagic, joins Jonathan Gandolf to explore the evolving world of growth marketing for B2B SaaS companies. Jason shares why narrowing your target market is critical to scaling from series A to B, how AI is transforming go-to-market strategies when applied thoughtfully, and why entrepreneurs need more grit than glamour. He also opens up about his journey as a serial founder and offers practical advice on using AI not as a gimmick but as a problem-solving tool.

In this episode, you’ll learn:

1. Why tight focus is vital for early-stage startup success
2. How to approach AI as a tool for solving specific business problems
3. The realities and mindset needed to thrive as a serial entrepreneur

Resources:

Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

Explore AudiencePlus: https://audienceplus.com

Connect with Jason on LinkedIn: https://www.linkedin.com/in/hubbardjason/

Explore DemandMagic: https://demandmagic.ai/

Timestamps:

(00:00) Intro

(03:00) Jason’s growth marketing origins and bootstrapped startup mindset

(04:30) The rise of services as software and AI’s role

(08:20) Why focus beats chasing a wide TAM

(11:10) Using AI to solve real business problems, not just for show

(14:30) Feeding go-to-market data into AI for actionable insights

(16:00) Personal uses of AI and digital nomad lifestyle plans

(17:30) The entrepreneurial mindset: why most won’t do it twice

“You don’t need to dumb down your message—you need to lift it up,” says Zach Messler, messaging strategist

In this episode of The Content Cocktail Hour, Jonathan Gandolf sits down with Zach Messler to unpack what clarity actually means in product marketing, and why so many companies get it wrong.

Zach shares the three deceptively simple questions every founder and marketer should be able to answer: “What is it? What does it do? Why does it matter?” He further discusses how to translate product complexity into compelling messaging, and why features don’t matter unless they’re tied to a deeper narrative. Zach also explains how to test your message in the wild, how to avoid the “everything, everywhere, all at once” trap, and the unlikely branding power of a Friday bourbon toast.

In this episode, you’ll learn:

1. Why product marketing starts with positioning, and not performance tactics
2. How to talk about your product without actually talking about your product
3. What message clarity really means 



Resources:

Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

Explore AudiencePlus: https://audienceplus.com

Connect with Zach on LinkedIn: https://www.linkedin.com/in/zachmessler/

Get Zach’s workbook: https://www.clarityrules.com 

Check out Zach’s newsletter: https://boomshockalocka.kit.com/e247950337

Explore zachmessler.com: https://zachmessler.com/ 

Timestamps:

(00:00) Intro

(02:18) The bourbon journey begins

(05:37) The art of sipping whiskey

(07:35) Bourbon collections and their value

(13:24) The shift to messaging

(14:49) The essence of product marketing

(16:40) Defining your product

(17:25) The importance of clarity in messaging

(17:38) Understanding the power of messaging

(18:08) The importance of positioning statements

(20:17) Balancing product and problem messaging

(25:24) Testing and refining your message

(28:45) Connecting features to value

(30:28) Creating a messaging guide

“Bold moves get bold results,” says JH Scherck, founder & CEO of Growth Plays

In this episode of The Content Cocktail Hour, JH Scherck, founder & CEO of Growth Plays, joins Jonathan Gandolf to break down what it really takes to win with content in today’s fragmented, AI-driven search landscape. JH unpacks why traditional SEO still matters—but only if it’s tied to real pipeline—and shares his candid take on how most companies are playing it too safe. From AI-powered discovery to the value of earned media and coined frameworks, he offers a clear-eyed perspective on what’s changing (and what’s not) in B2B content strategy. If you’re tired of surface-level tactics and ready to create content that actually drives results, this one’s for you.

In this episode, you’ll learn:

1. Why SEO still works—if you focus on pipeline
2. How AI is reshaping search behavior and discovery
3. Why bold, creative risks outperform safe plays in marketing



Resources:

Connect with Jonathan Gandolf on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

Explore AudiencePlus: https://audienceplus.com

Connect with JH Scherck on LinkedIn: https://www.linkedin.com/in/jhtscherck/

Connect with JH Scherck on X: https://x.com/jhtscherck

Visit Growth Plays: https://growthplays.com/

Timestamps:

(00:00) Intro

(01:09) Meet JH Scherck and Growth Plays

(02:18) Drinking Dominus and California wine habits

(03:06) Is SEO dead? Why it’s evolving, not obsolete

(05:18) Fragmented search, new discovery behaviors

(06:47) Search as an introduction, not the whole journey

(07:44) Differentiation and finding your point of leverage

(08:51) Why pipeline matters more than traffic

(10:38) Content’s role in qualified lead generation

(12:58) How AI and GEO are influencing visibility

(14:56) What earns citations in generative engines

(15:27) Coining phrases over chasing keywords

(16:51) Why no one has GEO figured out—yet

(18:36) Personalization, prompts, and user context in AI

(20:11) JH’s unpopular opinion: Play it safe, stay stuck

(21:29) Career-defining content risks that paid off

(22:41) Playing it safe won’t get you promoted

(23:16) How to connect with JH and Growth Plays

“Our content should be worth someone’s time—and money,” says David Ebner, founder & CEO of Content Workshop

In this episode of The Content Cocktail Hour, David J. Ebner, founder & CEO of Content Workshop, returns to chat with Jonathan Gandolf about the evolving expectations for content in a post-AI world. David shares why content should meet a new “threshold of value”—so good people would willingly pay for it—and explains how this mindset influences everything from newsletters to long-form assets. He also unpacks the tension between automation and authenticity, why “moral marketing” matters, and how brands can embrace SEO and backlinks even in a zero-click search environment. If you’re feeling stuck on the AI content hamster wheel, this episode offers a compelling case for slowing down and zigging when everyone else is zagging.

In this episode, you’ll learn:

1. How to create content that earns attention and trust
2. Why brands should rethink the ROI of SEO and backlinks
3. How to frame content creation as a moral decision, not just a metric



Resources:

Connect with Jonathan Gandolf on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

Explore AudiencePlus: https://audienceplus.com

Connect with David Ebner on LinkedIn: https://www.linkedin.com/in/davidjebner

Visit Content Workshop: https://contentworkshop.com

Timestamps:

(00:00) Intro

(01:06) David’s background and the origin of Content Workshop

(03:27) Ube mocktails and scaling back on drinking

(04:01) Why content should be worth paying for

(06:13) Valuing time and attention in the age of AI

(08:21) The ROI of high-value content

(09:57) Content libraries as recurring revenue assets

(11:21) Real examples of premium content from David’s team

(12:03) Give away the secret sauce

(13:54) Standing out with quality, not just quantity

(15:55) Why marketers must create with morality in mind

(17:22) Who does your content help—and hurt?

(20:54) David’s unpopular opinion: SEO still matters

(22:24) Why backlinks are more important than ever

(24:10) What generative engines reveal about good SEO

(25:20) How to connect with David and Content Workshop

“In the age of AI, the only differentiator is how you get your people to scale,” says Rachel Downey, founder and CEO of Share Your Genius

In this episode of The Content Cocktail Hour, Jonathan Gandolf sits down with Rachel Downey, founder and CEO of Share Your Genius, to explore what it really takes to build a high-impact podcast or content feed in today’s B2B world.

Rachel breaks down the difference between launching a “show” and building a “feed,” why downloads don’t tell the whole story, and how marketers should be thinking about ROI in human-first content strategies. She also shares how companies can start small, get scrappy, and make smarter content investments—without sacrificing authenticity.

In this episode, you’ll learn:

1. Why a podcast might not be the best place to start—and what to do instead
2. How to differentiate between metrics of performance and metrics of success
3. What “people-first” content actually looks like and how to scale it effectively

Resources:

Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

Explore AudiencePlus: https://audienceplus.com

Connect with Rachel on LinkedIn: https://www.linkedin.com/in/rachelelstsdowney/

Explore Share Your Genius: https://www.shareyourgenius.com

Timestamps:

(00:00) Intro

(01:26) The evolution of podcasting

(02:24) Personal journey in podcasting

(04:38) Show vs. feed

(06:29) Measuring success in podcasting

(14:08) Building a business case for podcasts

(17:21) The role of AI in content creation

(21:42) Why LinkedIn works better without a plan

“I don’t think B2B is as boring as people say it is. I think people are just bored in general,” says Brianna Doe, founder and CEO of Verbatim.

In this episode of The Content Cocktail Hour, Jonathan Gandolf sits down with Brianna Doe, founder and CEO of Verbatim, to unpack how B2B brands can show up with the same creative energy as B2C—without chasing trends or bloating their budgets.

Brianna shares why influencer marketing deserves a real seat at the B2B table, what a minimum viable pilot program actually looks like, and how building a network on LinkedIn helped her go all-in on her own agency with zero outbound. She also dives into how internal influencers (yes, even your CEO) can drive brand affinity more authentically than any corporate page.

In this episode, you’ll learn:

1. How to test influencer marketing in B2B—without a 6-figure budget
2. Why internal creators are your brand’s most underutilized asset
3. What it takes to confidently build a business and brand from scratch

Resources:

Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

Explore AudiencePlus: https://audienceplus.com

Connect with Brianna on LinkedIn: https://www.linkedin.com/in/brianna-doe/

Explore Verbatim: https://www.verbatim.com



Timestamps:

(00:00) Intro

(01:07) Brianna's background and current work

(01:52) From old fashioneds to margaritas

(03:06) Journey into influencer marketing

(04:42) Influencer marketing strategies for B2B

(12:28) Tools and resources for influencer marketing

(13:21) Internal influencers and company culture

(16:48) The journey to Verbatim

“Building strong relationships takes time, and that’s what many B2B marketers miss,” says Mike Allton, Chief Storyteller at Agorapulse

In this episode of The Content Cocktail Hour, Mike Allton, Chief Storyteller at Agorapulse, joins Jonathan Gandolf to discuss the evolution of social media marketing and why relationships, not quick sales, are the foundation of B2B success. Mike shares his journey from influencer ambassador to storyteller at Agorapulse, his thoughts on how brands can empower employees to share their story, and why relationship-building in social media cannot be automated by AI. He also discusses the challenges of AI-generated content, the importance of brand consistency, and why LinkedIn connection requests shouldn’t always lead to a sales pitch.

In this episode, you’ll learn:

1. How to empower employees to authentically represent your brand
2. Why building relationships on social media requires patience and time
3. How to balance automation with personal connection in B2B marketing



Resources:

Connect with Jonathan Gandolf on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

Explore AudiencePlus: https://audienceplus.com

Connect with Mike Allton on LinkedIn: https://www.linkedin.com/in/mikeallton/

Connect with Mike Allton through The AI Hat: https://theaihat.com/connect/

Explore The AI Hat: https://theaihat.com/ 

Explore Agorapulse: https://www.agorapulse.com/

Timestamps:

(00:00) Intro

(01:31) Mike Allton’s journey and role at Agorapulse

(04:03) The importance of empowering employees to share brand stories

(07:02) The shift from corporate to human voices in social media

(11:06) Navigating AI’s influence on social media content

(12:30) How AI is both a tool and a challenge for content creation

(13:04) The dangers of LinkedIn pitch slaps

(14:30) Balancing automation and personal connection in outreach

(19:17) The evolution of social media marketing in B2B

(22:19) The future of relationship-building in digital marketing

“Positioning and messaging might be perfect, but without distribution, it doesn’t mean anything,” says Jonathan Pipek, founder and CEO of Blue Manta Consulting

In this episode of The Content Cocktail Hour, Jonathan Pipek, founder and CEO of Blue Manta Consulting, joins Jonathan Gandolf to unpack the often-misunderstood world of product marketing—and why distribution, not differentiation, is the real battleground for startups. Jonathan shares why startups should consider fractional product marketing support before making their first full-time hire, what’s broken about personalization at scale, and why webinars feel increasingly outdated in today’s crowded B2B environment. He also dives into the critical role of language, community, and actionable content in building trust with modern buyers.

In this episode, you’ll learn:

1. When startups should hire product marketing and when they shouldn’t
2. Why AI personalization at scale often backfires
3. How distribution has overtaken positioning as the real growth challenge

Resources:

Connect with Jonathan Gandolf on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

Explore AudiencePlus: https://audienceplus.com

Connect with Jonathan Pipek on LinkedIn: https://www.linkedin.com/in/jonathanpipek/

Explore Blue Manta Consulting: https://www.bluemantaconsulting.com/

Timestamps:

(00:00) Intro

(01:31) Jonathan Pipek’s background and approach to startups

(04:03) Defining product marketing at early-stage companies

(07:02) When to hire product marketing full-time vs fractional

(11:06) What’s not working: AI personalization at scale

(12:30) Why ads are delivering diminishing returns

(13:04) The distribution problem no one talks about

(14:30) How product marketing and content marketing should collaborate

(19:17) Why webinars feel outdated in 2025

(22:19) Why actionable content beats thought leadership today