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About the Episode:Chris Cunningham is a founding member and Head of Social Marketing at ClickUp, the fast-growing productivity platform now valued at $4 billion. Since shaping ClickUp’s brand voice and social presence from 2017, Chris has been instrumental in engineering a content system that regularly generates 200M+ monthly impressions and consistently translates content virality into real leads and customers.In this workshop episode of Uploading, Chris breaks down ClickUp’s journey from early hustle—making videos solo and closing deals by hand—to building a repeatable, scalable content operation with an in-house “writer’s room,” comedic actors, and a growth strategy spanning multiple platforms.Chris and host Blaine unpack content pivots, hiring creators, building brand voice, and why entertainment-first content matters for B2B. Chris also gets tactical: how to mix content types across the funnel, the operational playbook for consistent output, leveraging AI tools, success metrics, and what it takes to hit massive growth milestones.Finally, Chris shares actionable frameworks for solo founders and small teams starting from scratch—plus candid takes on virality, team structure, platform strategy, and what’s next for ClickUp’s $4B content engine.Today, we'll cover:- How ClickUp scaled from low-budget solo content to 200M+ impressions per month- The “bets” and breakthroughs that defined ClickUp’s content playbook- Building a repeatable system: team, workflow, “writer’s room,” and actors- Entertainment vs. product-driven content—and the ideal content mix- Measuring ROI: turning impressions and brand awareness into real leads and customers- Frameworks and advice for solo creators and early-stage teams to start content from scratch- Platform-specific strategies for LinkedIn, Instagram, TikTok, YouTube, and beyond- Personalization, AI, and creator partnerships: the new wave of B2B contentWhat You'll Learn1. Building a Scalable Content Engine2. Hiring and Leveraging In-house Creators3. Mixing Entertainment and Product Content4. Omnipresence across Multiple Social Platforms5. Testing, Iterating, and Doubling Down on Winners6. Aligning Content with Business Goals and Funnels7. Creating Efficient, Repeatable Content SystemsTimestamps00:00 Meet Chris Cunningham: ClickUp’s content architect02:11 Chris’s background: from agency to ClickUp’s founding team08:07 Platform-specific content strategy & goals11:28 Making content a team priority: systems & scheduling14:37 Inside ClickUp’s instagram strategy15:38 The ABCD formula: testing for virality16:09 Case study: viral skits, trends, & relatable office content19:29 Operations: writers’ room, shooting schedule, & execution23:23 Starting from scratch: building in public & early tactics25:47 Frameworks for virality: the anatomy of a viral video27:41 Winning concepts: relatability, shareability, & emotional triggers30:55 Scheduling vs manual posting: what works best32:18 YouTube strategy: current state & future focus33:36 Platform prioritization: focus, layering, & growth sequence35:52 Content funnel mix: brand awareness vs product promotion37:24 Content ratio: top, middle, & bottom of funnel by stage40:00 Staff vs. actors: who should be in your content?42:10 Video length: short vs long content & platform preferences43:35 Looking ahead: 2025 content experiments & new channels46:19 Where to follow Chris & ClickUp“We’ve very big on shots on goal. We want to put as many shots up as possible, but we want to have calculated shots. We want to take them with low budgets… I’ll make a bet and I’ll start it very cheaply.” — Chris Cunningham“The only way it’s really going to scale is if I brought in an expert... I took a bet that all companies would have content creators if they wanted to compete. They’ll have some kind of creator that creates content for them consistently.” — Chris Cunningham“Content's just another task, right? Like anyone can make excuses. So if you're just not making content, it means you don't prioritize it. We prioritize it.” — Chris Cunningham“The dividends content rewards with is nuts. The amount of people I’ve met, the people who DM me and just what I’m learning… There’s no reason not to make content.” — Chris Cunningham“If I had to start over and I’m at a new company—we’re building in public... No actors, just talking about what we’re working on. At the end of the day, I would just ask for like 5-10 minutes of all the early employees: what did you do today? And find a cool, clever way to chop it up. That’s exactly what I would do.” — Chris Cunningham“You need to know your ICP. If you’re creating content and you don’t know who you’re creating for, you really just lost the whole goal right there.” — Chris CunninghamShow notes powered by Castmagic---Have any questions about the show or topics you'd like us to explore further?Shoot us a DM; we'd love to hear from you.Want the weekly TL;DR of tips delivered to your mailbox?Check out our newsletter here.Follow us for content, clips, giveaways, & updates!Castmagic InstagramCastmagic TwitterCastmagic LinkedIn  ---Blaine Bolus - Co-Founder of CastmagicRamon Berrios - Co-Founder of CastmagicChris Cunningham - Head of Social Marketing at ClickUp

About the Episode:Eugene Khayman is the COO of Million Dollar Sellers (MDS), an exclusive community for top Amazon entrepreneurs that he helped grow from a humble Facebook group into a thriving six-figure membership of 700 members generating $11 billion in annual sales.In this episode of "Uploading...", Eugene shares the organic journey of building MDS alongside running his own Amazon brand. He discusses key strategies that made MDS successful, such as their "give more, get more" philosophy, setting a high bar for membership to filter out noise, and delivering immense value that justifies the $7,500 annual membership fee.Eugene also unpacks the business model powering MDS, including multiple revenue streams from membership, partnerships, affiliates, and events. He emphasizes the importance of member-only perks, local chapters, and a robust software platform to organize resources and drive engagement in a community. Finally, Eugene offers advice for content creators looking to launch their own paid communities.Today, we'll cover:- How MDS grew organically from a humble Facebook group to a thriving community- The "Give More, Get More" philosophy that drives member engagement and success- Strategies for filtering out noise and maintaining a high-quality, focused community- The business model behind MDS and why people pay over $7,000 a year to be part of the network- Eugene's insights on scaling communities while maintaining their identity and core values- Tips for building and monetizing your own niche membership communityWhat You'll Learn1. How to Start a Community from Scratch2. Strategies for Organic Community Growth 3. How to Filter Noise in Early Stages of Community4. When and How to Monetize a Community5. Thriving vs. Dead Communities6. Software for Managing Communities7. Application and Onboarding Process for Established Communities8. Tips for Creators on Building and Monetizing a CommunityTimestamps00:00 Intro and background on Eugene and Million Dollar Sellers (MDS) 04:45 Current stats of MDS community: revenue, members, ticket price 06:45 Starting a community organically and verifying/filtering members 08:33 Monetization: when to do it and how to create value14:44 Where to host a new community and who to bring in17:53 Seeding a new community: starting conversations and keeping it alive24:02 Application process and onboarding new members to MDS now 26:55 Where MDS community is going; chapters for local connections 30:30 Platforms used to run MDS community; GroupOS app development33:44 Opportunities for content creators to monetize via communities 38:33 Q&A: Strategies for specific community examples from audience 44:00 Building a wait list and leveraging existing audience for a community 46:02 Options for immediately monetizing a new community 50:44 Turning virality into community; setting criteria and values 55:15 Wrap-up; where to find Eugene on socialBuilding Engaged Communities: “I think your first objective should always be like that core group of the founding members. For us I think it was like 150 members before we started actually monetizing. But you know, I would say you want to get to 100 members, you want to have at least 40, 50 die hard members that are engaging in there every single day. You want to get at least five to 10 conversations happening a day. If somebody can ask a question and have it answered that same day like that, that's the value creation right there, right? You don't want to be the one, you yourself answering every single question because you yourself, you don't know everything.” — Eugene Khayman, 00:08:33 → 00:09:25Monetizing and Scaling a Community: “Whenever somebody starts making a profit because of others, there's going to be some level of, like, why are we doing this? And there's also going to be that, that hesitation to grow. Everybody's going to be like, ’We're so great, we don't need more people.’ Right? And we've crossed that bar—100 members, 200 members, 400 members—there's always that, ‘Oh, we're too big, we're too big, we're too big.’ And you're going to get that pushback. The biggest thing that I think that helped us do it together is one, once we started monetizing, we started putting all of that money back into more events and more resources, building a team… Once you start adding back value by hiring people that help keep things organized, putting on calls regularly, doing events regularly, you'll get that respect from those members, those existing members. And then the new people that are coming in, you have to show that these new people actually bring value to the community.” — Eugene Khayman, 00:11:33 → 00:13:03Show notes powered by Castmagic---Have any questions about the show or topics you'd like us to explore further?Shoot us a DM; we'd love to hear from you.Want the weekly TL;DR of tips delivered to your mailbox?Check out our newsletter here.Follow us for content, clips, giveaways, & updates!Castmagic InstagramCastmagic TwitterCastmagic LinkedIn  ---Blaine Bolus - Co-Founder of CastmagicRamon Berrios - Co-Founder of CastmagicEugene Khayman - COO of Million Dollar Sellers

Martha Bitar, co-founder and CEO of Flodesk, shares her journey of building a $30 million ARR email marketing platform. She discusses the enduring power of email marketing and shares strategies for creating engaging content. Topics include optimizing subject lines, the importance of segmentation for audience targeting, and future trends like AI in email marketing. Martha also offers actionable tips on improving deliverability, maintaining subscriber engagement, and the best practices for email design that drive conversions.

Jonathan Goodman, founder of the Personal Trainer Development Center and author of 11 self-published books, details his transformation from personal trainer to multimillion-dollar entrepreneur. He emphasizes the importance of understanding audience needs over chasing fleeting trends. Jonathan shares strategies for content creation that build sustainable businesses while avoiding burnout. He advocates a balanced approach to work and life, and highlights client-centric strategies to cater to high-value clients, ensuring overall business success.

Jay Clouse, the founder of Creator Science and a content strategy expert, shares his journey from product management to the creator economy. He discusses the importance of content packaging and effective techniques for engaging audiences across multiple platforms. Jay dives into the balance between scripting and spontaneity in podcast interviews, emphasizing active listening and natural conversation flow. He also explores creating a sustainable business model for content creators, highlighting income streams and the role of social media in audience growth.

JT Barnett, founder of CreatorX and former professional athlete, shares invaluable insights into building and monetizing a personal brand. He emphasizes the power of organic engagement over paid ads and discusses effective content strategies for platforms like YouTube and TikTok. JT highlights the importance of creating a signature series to foster audience loyalty and the role of AI tools in content creation. He also dives into the significance of partnering genuinely with creators for business growth and shares practical tips to avoid burnout in the creative process.

Chris Savage, co-founder and CEO of Wistia, dives into the future of video and the impact of AI on content creation. He discusses the rise of authentic storytelling in an AI-driven world and how to adapt to audience expectations. Personal branding for founders takes center stage, with Chris sharing effective strategies for creating engaging content on platforms like LinkedIn. He underscores the importance of goal-setting and self-compassion in overcoming the challenges of business growth and the content creation process.

About the Episode:Jay Yang is a content creator with over 100,000 followers and the Head of Content for Noah Kagan, founder of AppSumo. At only 18 years old, Jay has already made a significant impact in the world of content creation while still attending university.In this episode of “Uploading…,” Jay shares his journey from experimenting with various online projects to landing an opportunity to work with Noah Kagan using his TAG method. He discusses his content creation process, balancing his work with education, and overcoming imposter syndrome. Jay also shares insights into his upcoming project on creating accessible social content templates for beginner creators.Today, we'll cover:- Jay Yang's content creation and audience growth frameworks- How to land high-profile opportunities using Jay Yang’s TAG method- Overcoming imposter syndrome and embracing the learning process in content creation- Benefits of social content templates for beginner creatorsWhat You'll Learn1. Target-Audit-Gift Method2. Importance of Empathy and Pre-Work3. Content Creation and Repurposing Strategies4. Content Testing and Metrics5. The “Name Test”6. Top-Down Approach to Content Creation7. Bottom-Up Approach to Content Creation8. Benefits of Using Content TemplatesTimestamps00:00 How Jay Yang got into content creation03:03 Jay Yang’s “portfolio of failure,” TAG method06:42 Key learnings from working at Beehiiv09:59 How to land an opportunity with your favorite company14:38 Optimizing Noah Kagan’s content workflow17:27 Quantitative approach to marketing; content testing21:10 From experimentation to building a content engine that works24:13 Overcoming imposter syndrome in content creation28:02 Benefits of using social content templatesMastering Empathy in Business: “I think the greatest skill you can learn as a marketer, a creator, an entrepreneur, even just as a person, is empathy and being able to place yourself in someone else's shoes.” — Jay Yang [00:08:00 → 00:08:10]Keys to Building Professional Relationships: “I think that strategy of where most people ask, how can I help you? Or what can I do to work for you for free? The problem with that approach is that by asking, without showing, you're actually making the other person do more work to figure out who you are and if you're any good and what you can actually help with... And so the question that I ask myself, and I encourage people listening to this to ask is, how can I make this a no brainer for the other person? And that kind of ties back into that empathy, right? Putting yourself in the other person's perspective... To work with your favorite entrepreneur or company, basically, you need to show two things, that, number one, you want the job, and number two, that you can do the job. And the best way that I believe you can do that is to do the work upfront, to use the TAG method, to do what I like to call pre-work. And I think the coolest thing about this approach is you don't have to have any experience or, you know, credibility or a degree." — Jay Yang [00:12:46 → 00:13:13]Overcoming Impostor Syndrome in Content Creation: "I only have to be one chapter ahead of the textbook of life. Like, you don't have to be the guru preaching at the top of the mountain. You just have to be one or two steps ahead of the people behind you and the people you're sharing content to. So that's kind of what I'm realizing is, as I grow my brand, I'm not trying to be the professor at the front of the class. The way I like to view myself is as that kid in the back sharing his notes with the rest of his classmates." — Jay Yang, [00:25:21 → 00:25:49]Show notes powered by Castmagic---Have any questions about the show or topics you'd like us to explore further?Shoot us a DM; we'd love to hear from you.Want the weekly TL;DR of tips delivered to your mailbox?Check out our newsletter here.Follow us for content, clips, giveaways, & updates!Castmagic InstagramCastmagic TwitterCastmagic LinkedIn  ---Blaine Bolus - Co-Founder of CastmagicRamon Berrios - Co-Founder of CastmagicJay Yang - Head of Content at AppSumo

Kane Kallaway, a content creator with over 550K followers and a billion views, specializes in tech, AI, and cult brands. He discusses creating engaging short-form videos using curiosity loops and strategic hooks to captivate audiences. Kane emphasizes the significance of rhythm and pacing in editing for viewer engagement and shares his workflow for idea generation and scripting. He highlights the importance of tailoring content for various platforms to drive conversions to longer formats, making short-form videos a powerful tool for audience nurturing.

About the Episode:Dakota Robertson is the founder of Growth Ghost, a social media ghostwriting business with high-profile clients that include best-selling authors, prominent influencers, and 7 and 8 figure entrepreneurs. He scaled this venture to generate $30,000-$50,000 per month within its first nine months, then transitioned to his current role as a personal brand consultant after two successful years.Now with an audience of over 550,000 followers and generating monthly earnings exceeding $100,000, Dakota's mission is to help others to achieve freedom and make an impact through their content and online businesses. He offers a free personal branding course for creators, coaches, and business owners.In this episode of DTC Pod, he shares his strategies for creating viral content, emphasizing the importance of sharing personal experiences, addressing pain points, and providing actionable advice to connect with audiences. He also discusses his ‘what-why-how’ writing framework, his content repurposing workflow, and the value of ghostwriting for those who struggle with content creation.Today, we'll cover:- The art of simplifying your message and leveraging psychology in copywriting to create compelling content- The critical roles that relevance and curiosity play in content consumption and purchasing decisions- Dakota Robertson's proven "what, why, how" framework for creating highly engaging content- The growing importance of ghostwriting in the social media space and how it can help clients achieve their goals- Strategies for building a content funnel to nurture relationships and convert followers into customersWhat You'll Learn1. Techniques for Creating Engaging Content2. Social Media Growth and Ghostwriting3. Content Creation Workflow4. Repurposing Content5. Building a Personal Brand6. Relevance and Curiosity in Content7. The “What, Why, How" Framework8. Funnel Strategy and Long-Form ContentTimestamps00:00 Dakota Robertson’s background02:22 How Dakota Robertson started on socials05:15 Two important copywriting lessons07:24 Inciting relevance and curiosity in social content10:47 Dakota Robertson’s what-why-how framework14:19 On ghostwriting as a career path16:08 Creating content yourself vs employing a ghostwriter19:18 Dakota Robertson’s content workflow22:41 Ways to think of content ideas25:06 How to create a transparent relationship with your audience29:23 Sales funnel offers and how to convert with contentUnderstanding the Audience’s Pain Points: “Imagine you're in a desert and you have no water. It's scorching hot. You've been walking for days, and then someone has a little water bottle. How much would you pay for that? You’d probably empty your entire bank account. Opposed to, if you're just walking on the street, you're not thirsty, you're fine. It's like, you probably won't even buy it. The only difference is the context of the pain you're in. So something is showing, ‘Hey, like, I can solve this pain point for you,’ then it's gonna be more relevant to the person.” — Dakota Robertson [00:08:30 → 00:09:02]Creating and Sharing Personal Content: “I find a lot of people in business, they're so focused on, you know, giving value and actionable stuff, and they totally neglect the personal side of things. So I think there should be more of a focus on personal stories, worldviews, and opinions, even if it's polarizing, because that's the stuff that's gonna make people love you, even if it means other people hate you.” — Dakota Robertson [00:24:44 → 00:25:06]Impact of Long-Form Content on Conversion: “If someone consumes a three-second tweet, it's like, okay, but if someone consumes a ten-minute YouTube video, you're taking up more real estate in their mind, and you're nurturing that relationship way more because they can see and hear you. And that's the stuff that converts way better, is long form. So I'm always thinking about how can I convert my short-form content to long-form and ideally get them on my newsletter so they can have a direct line of access?" — Dakota Robertson [00:32:01 → 00:32:29]Show notes powered by Castmagic---Have any questions about the show or topics you'd like us to explore further?Shoot us a DM; we'd love to hear from you.Want the weekly TL;DR of tips delivered to your mailbox?Check out our newsletter here.Follow us for content, clips, giveaways, & updates!Castmagic InstagramCastmagic TwitterCastmagic LinkedIn  ---Blaine Bolus - Co-Founder of CastmagicRamon Berrios - Co-Founder of CastmagicDakota Robertson - Founder of Growth Ghost