AI for Business Podcast
AI for Business is the podcast where founders, creators, and business leaders learn how to actually use AI to grow, scale, and stay competitive. Hosted by Francis Ablola and Brian Hanson co-creators of AI for Business, you’ll get behind-the-scenes access to private interviews, expert conversations, and tactical playbooks from industry leaders using AI to drive real results. Whether you’re a startup owner, agency leader, content creator, or operator, this show breaks down what’s working right now in marketing, operations, product, and growth all powered by AI. New episodes weekly featuring founders, investors, SaaS executives, and creators who are building smarter, faster, and better with AI.
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E11: Why Empathy Beats Algorithms: The Real Secret to Copy That Converts
09/05/2025
E11: Why Empathy Beats Algorithms: The Real Secret to Copy That Converts
In this powerful episode of AI for Business, I sit down with Darby Rollins for a behind-the-scenes preview of my presentation for the upcoming Scale With AI Summit. We talk about one of the most underutilized but essential elements in marketing: empathy. I share how this emotional superpower, when combined with modern AI tools like Claude and ChatGPT, can help you connect with your audience, write better copy, and drive real business results. We dive into my journey from the days of direct mail and radio ads to leading AI-powered campaigns today. I also share the turning point that taught me to never skip audience research, and how you can shortcut years of copywriting experience into usable, profitable content with the right process. If you’ve ever struggled with messaging that just doesn’t land—or if you’re looking to turn raw ideas into revenue—this episode is for you. Timeline Summary [0:00] – Introduction [1:15] – The shift from traditional marketing to AI-enhanced copy and testing [2:44] – How AI helps shortcut 20 years of direct response experience [4:02] – What empathy really means in the context of copywriting [5:10] – Why “understanding your audience” is more than just a buzzword [7:02] – A humbling story about learning from Gary Halbert, the hard way [8:02] – How to speak to problems your customers don’t know how to explain [9:46] – The one outcome you’ll walk away with from the Scale With AI Summit [10:34] – Why Claude is my go-to AI writing tool and how I use it for research [11:15] – Using market data from real comments to write high-impact copy [12:00] – The synergy between empathy-based copy and market research tools [12:40] – How AI helps you speak in your customer’s language—and sell more [13:30] – Final thoughts and how to join us at the live summit Five Key Takeaways Empathy is the missing link – Great copy doesn’t just sound good; it resonates because it feels personal and relevant. Old school meets new tech – My background in direct mail sharpened my instincts—AI now helps speed that process 10x. Research before you write – Knowing your market on an emotional level is what separates mediocre marketing from greatness. Use AI to echo your audience’s voice – Claude and ChatGPT can mirror customer language when you feed them the right data. You don’t need decades of experience—just the right framework – I’ll show you how to use the same process I teach my team to create content that converts. Enjoyed this episode? Please rate, follow, and share AI for Business with someone who’s ready to unlock the power of empathy-driven, AI-supported marketing. Your support helps us grow and continue to bring you next-level content.
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E10: Turning ChatGPT into Your Ultimate Marketing Assistant
08/29/2025
E10: Turning ChatGPT into Your Ultimate Marketing Assistant
In this special edition of AI for Business, I had the privilege of joining Darby Rollins live at the Genius University Summit for a deep dive into AI-driven marketing that actually connects. We go beyond buzzwords to unpack the exact research strategies, audience-building frameworks, and prompt engineering techniques that I’ve used to generate over $50 million in online sales—and teach to my clients and community. During this session, I walk you through how to build an AI-powered marketing research machine using tools like ChatGPT and Claude, so you can speak directly to your audience’s true pain points and desires. Plus, I share the story of how I was humbled in front of my marketing hero Gary Halbert and how that moment transformed the way I do research, write copy, and build offers. Whether you’re launching your first product or scaling to 8-figures, this episode is packed with practical strategies and tools you can implement right away. Timeline Summary [0:00] - Introduction [1:06] - Reflecting on 20 years in marketing and the evolution of direct response [6:12] - How being an introvert pushed me into mastering copywriting [10:41] - A tough lesson from Gary Halbert that changed how I approach research [12:22] - Why empathy is the true superpower of successful marketers [16:19] - The modern shortcut to old-school research: mining reviews, Reddit, and more [20:21] - Favorite tools for scraping and organizing customer insights [24:09] - How to prompt ChatGPT like a seasoned researcher [29:13] - The ChatGPT vs Claude debate: when to use each for best results [36:01] - Creating a style guide that mirrors your audience’s language and tone [43:10] - Writing a high-converting sales letter with the help of AI [47:14] - Generating product ideas based on real audience feedback [54:17] - Turning webinars and sales calls into powerful written content [55:42] - Training virtual assistants to follow this system—even without copy experience Five Key Takeaways Empathy drives conversions – The best marketers don’t just know their product; they deeply understand their audience’s pain, desires, and language. AI should be your assistant, not your crutch – ChatGPT and Claude can streamline research and content creation, but the quality depends on the inputs you provide. Real voices come from real data – Use Amazon reviews, Reddit threads, and YouTube comments to understand exactly how your audience speaks and what they care about. Create style guides based on audience tone – A persona-driven style guide helps keep your messaging consistent, relatable, and effective across all content. Prompts are the new skillset – Learning to engineer great prompts is what separates average AI users from high-performing marketers. If you got value from this episode, don’t forget to rate, follow, share, and review AI for Business. Your support helps us keep delivering powerful strategies and practical tools you can use to grow your business faster with AI. Let me know if you’d like this version tailored for a blog post or email newsletter.
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E9: How to Win Big with AI Tools, Prompts, and Strategies That Work
08/01/2025
E9: How to Win Big with AI Tools, Prompts, and Strategies That Work
In this high-energy, live-recorded episode from the AI for Business Summit in Orlando, I’m joined by my longtime friend and business partner Brian as we dig into the latest AI tools and strategies that are transforming how entrepreneurs operate, market, and scale their businesses. Whether you’re a seasoned pro or just starting to explore AI, this session is packed with insights, live demos, and real-world use cases designed to show you exactly how to stay ahead. We cover everything from building fully functional apps without writing a single line of code, to generating sales proposals in minutes, to using AI as your personal voice assistant, therapist, and business coach. You’ll hear how to unlock new revenue streams, automate tedious tasks, and harness AI as your creative sidekick. This is the era of the button pusher, and in this episode, we show you exactly how to push the right ones. Timeline Summary: [0:00] - Introduction [0:58] - Live intro from the AI for Business Summit in Orlando [2:03] - Agent browsers like Menace are changing the game in real-time AI capabilities [3:27] - How I built a full presentation with AI in minutes using Menace and our super prompt system [4:17] - Meet Yolanda: My ChatGPT voice assistant who knows my life story and helps me stay focused [10:11] - Live roleplay: Selling AI services using voice-to-text features in ChatGPT [14:35] - Real-time language translation with AI during client conversations [18:05] - Inside the AI for Business app: explore 10+ tools from business plans to brand voice creation [22:01] - Generating branded images, ads, and logos with text-to-image prompts [26:35] - Creating unforgettable AI ads with Vo3 and pattern-interrupt content strategies [36:07] - No-code app creation with Lovable: building an entire lead gen app live on stage [43:13] - Understanding MVPs and testing ideas fast with app builders [45:09] - Turning a single prompt into a viral marketing tool with the Super Prompt Generator [50:00] - Publishing your new app and connecting it to a custom domain in minutes Five Key Takeaways: You don’t need to be a tech expert to harness AI. With the right tools, anyone can create content, build apps, and automate workflows. AI voice assistants are more than productivity hacks. They can learn your habits, recall past conversations, and help you navigate life and business challenges. No-code tools like Lovable can build full-stack apps—including websites, quizzes, and lead magnets—faster and cheaper than ever before. AI-generated video ads and branded images are now accessible to everyone, making pattern-interrupt marketing a powerful strategy for social media. Prompts are everything. The quality of your AI results depends on the prompts you give. Use our Super Prompt Generator to stand out like a pro. If you got value from this episode, please rate, follow, and review the AI for Business podcast. It helps us reach more entrepreneurs like you who are ready to scale with AI.
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E8: How We Built a Multi-Million Dollar AI Business from a Facebook Group with Francis Ablola & Brian Hanson
07/25/2025
E8: How We Built a Multi-Million Dollar AI Business from a Facebook Group with Francis Ablola & Brian Hanson
In this behind-the-scenes episode, I sit down with my long-time business partner Brian Hansen to share the real, raw story of how AI for Business came to life. We take you back to our early days—hosting free meetups at local libraries and jamming 90 people into a hotel room to becoming founders of one of the fastest-growing AI education platforms in the world. We open up about the wins, the losses, and the pivotal moments that shaped our journey—from selling used car parts online to building multi-seven-figure businesses in real estate and digital education. You’ll hear how we used nothing but credit cards, a Facebook group, and obsession to launch AI for Business, and how we continue to pivot, build, and stay ahead in this fast-moving space. Episode Timeline & Highlights [0:00] - How a casual happy hour turned into a deep dive into our origin story [2:01] - From library meetups to selling out our first seminar—before we even had a product [4:45] - Leveraging partnerships to build an audience fast [5:34] - Brian’s nervous but unforgettable first time on stage [8:17] - Launching our first mastermind and building a loyal community [9:34] - Why imperfect action trumps perfection every time [12:06] - Creating a lifestyle business that generated hundreds of thousands in profit [14:33] - How a massive company shutdown forced us to rebuild from scratch [17:21] - Real lessons from losing seven figures during the pandemic [20:01] - Why AI presented the ultimate shortcut—and how we seized it [23:53] - Building AI for Business with no external funding or borrowed resources [29:04] - The unique opportunity to become an AI expert in your niche [34:44] - Why events and real-world relationships matter more than ever [41:09] - How the right people and partnerships built the foundation for everything 5 Key Takeaways Start Before You’re Ready – We launched AI for Business without a logo, team, or clear roadmap—just a Facebook group and a commitment to help. Imperfect Action Wins – Our first event wasn’t polished, but it sold out. Taking action before everything feels perfect is key to momentum. Relationships are Everything – From our first business partnerships to speaking opportunities 15 years later, relationships have fueled every major leap. You Don’t Need Expertise—Yet – AI is a wide-open field. If you combine it with your niche, you can become the go-to expert faster than you think. Resilience is Built in the Struggles – Whether it was losing revenue during COVID or getting burned by partners, each setback made us stronger and more focused. If you got value from this episode, I’d love for you to follow the show, leave a review, and share it with a friend or teammate who’s ready to build something big. Your support means everything.
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E7: Building ClickUp from a $0 Budget to a $4B Valuation with Chris Cunningham
07/18/2025
E7: Building ClickUp from a $0 Budget to a $4B Valuation with Chris Cunningham
In this power-packed episode of our Happy Hour series, I sit down with Chris Cunningham, co-founder of ClickUp, the $4 billion AI-powered project management platform. Chris takes us behind the scenes of ClickUp’s explosive growth and shares his no-nonsense strategies for scaling, networking, and leveraging AI to build massive business impact. From grassroots marketing to raising over $500M in funding, this conversation is loaded with entrepreneurial gold. We talk about what it means to lead with value, how Chris overcame a debilitating fear of public speaking, and why he believes in showing up and shipping—even if things aren’t perfect. Whether you’re building a startup, scaling an agency, or just trying to keep your business organized, Chris delivers both inspiration and practical advice to help you move faster and smarter. Episode Highlights [0:00] - Introduction [1:10] - Meet Chris Cunningham, ClickUp co-founder and master connector [2:07] - Joe’s automation genius: Why he’s the best ClickUp + Zapier trainer [3:28] - Why AI is opportunity, not threat—if you’re willing to learn [5:04] - What makes ClickUp the all-in-one productivity tool [6:12] - Competing with giants: How ClickUp disrupted a saturated market [8:05] - Raising $535M: ClickUp’s unique edge that won over investors [9:10] - Funny + bold: How ClickUp’s marketing crushed the SaaS playbook [11:10] - The scrappy moves that gave ClickUp early traction [12:33] - The AppGator tool that turned bad reviews into sales leads [13:27] - What it really takes to push through fear and doubt as an entrepreneur [15:15] - Why resilience, not perfection, is the true key to success [16:07] - The power of giving first and building real relationships [18:09] - The single most overlooked way to get your ideas noticed [20:18] - How Chris turned public speaking from fear into a superpower [22:03] - Tips on building an irresistible brand personality in your content [24:40] - Using short-form content to build long-term business relationships [27:55] - Why most people fail to get their ideas seen—and how to fix it [30:14] - Chris’s thoughts on ClickUp’s biggest missed opportunities [33:02] - The long-term play of community and audience building [36:18] - What Chris is excited about in the AI space right now [38:47] - Behind-the-scenes of running an AI-first business [41:10] - Chris’s playbook for startup founders in today’s tech landscape [44:55] - The one behavior shift Chris recommends to every entrepreneur [47:20] - Why the “ship fast, iterate faster” mentality still wins [49:45] - How to keep your energy and optimism high—even in chaos 5 Key Takeaways Be Scrappy and Ship Fast: ClickUp’s early growth came from prioritizing action over perfection. They pushed updates weekly and welcomed feedback—even when the product had bugs. Leverage AI with Intentionality: Embrace AI as a partner in productivity. Chris urges us to learn the tools rather than fear them—especially when platforms like ClickUp are integrating it daily. Build to Serve, Not to Take: Chris credits his success to focusing on adding value to others before asking for anything in return. That mindset built a powerful, loyal network. Content is Leverage: Whether you’re creating videos that get 200 views or speaking on a stage, consistent visibility in communities can open massive doors. Overcome Fear by Outworking It: From stuttering in childhood to commanding rooms of thousands, Chris proves that fear is beatable—with enough time, practice, and grit. Links & Resources Connect with Chris: [email protected] Enjoyed this episode? Please rate, follow, and leave a review! Share this with someone who’s ready to stop waiting and start building. Let’s grow together.
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E6: The Real ROI of AI & Building Systems That Save Time & Boost Revenue with Joe Zapiain
07/11/2025
E6: The Real ROI of AI & Building Systems That Save Time & Boost Revenue with Joe Zapiain
In this episode, I sit down with Joe Zapiain one of the world’s most sought-after automation specialists to explore the real power of AI and automation in today’s business landscape. Joe isn’t just about zaps and bots he’s about building systems that free people from the grind and empower them to focus on what they love. From working with Shark Tank’s Daymond John to helping a cloak company explode from zero to millions overnight, Joe’s stories are as actionable as they are jaw-dropping. We unpack the difference between flashy automations and the real pain points that quietly hold businesses back, and how solving those can lead to massive gains. Joe also gets candid about what excites him most in the AI world, what truly worries him, and the practical systems every entrepreneur should be thinking about now. Timeline Summary: [0:00] - Introduction [1:45] - Joe’s approach to automation: focus on freedom, not just profits [4:50] - What it’s like building systems for Daymond John’s companies [6:20] - The subtle automations that create the biggest wins [9:56] - How a viral TikTok cloak video led to a multimillion-dollar business [13:00] - Scaling a three-person team to handle massive order volume [18:00] - Automating customer support: returns, complaints, and sales follow-up [20:30] - Why brick-and-mortar businesses might be the real winners in the AI era [23:53] - Joe’s step-by-step client process: blueprint, implementation, ongoing evolution [27:00] - The darker side of AI: how Joe protects his own kids and sees risk growing [34:00] - From McLarens to Zapier: Joe’s unexpected journey into automation [38:00] - Why Joe prefers Zapier over other tools and his blunt take on Asana [42:00] - Real estate, email GPS, and overlooked opportunities in admin workflows [46:00] - Top 3 automation tools Joe uses in nearly every client setup 5 Key Takeaways: Automation is about quality of life – Joe’s core mission is helping business owners get their time back, not just chasing revenue. The biggest wins come from the smallest pain points – Simple automations like reminders or filtering emails can radically shift a business. Validation before creation – Joe shares how his client Chris Claflin validated his entire cloak business with one video before producing anything. Being ‘AI fluent’ is now a job requirement – Knowing how to use tools like Zapier and ChatGPT is no longer optional in modern business. Human connection is the new premium – As AI rises, genuine human interaction and in-person experiences are becoming more valuable than ever. Links & Resources: Joe Zapiain: ClickUp: Zapier: Enjoyed the episode? Don’t forget to follow, rate, and review the podcast. It helps more people discover these insights—and if you found it helpful, share it with someone who needs to hear it!
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E5: Building a Viral Real Estate Brand & AI Secrets with Dolmar & Keisha Cross
07/04/2025
E5: Building a Viral Real Estate Brand & AI Secrets with Dolmar & Keisha Cross
In this episode of the AI for Business Podcast, Brian and I are thrilled to welcome Dolmar and Keisha Cross, stars of A&E’s Zombie House Flipping: Tampa and our brilliant business partners. This lively happy hour conversation dives into how they’ve harnessed AI to build their social media brand, dominate the real estate market, and even land a spot on national TV. We explore how AI can humanize your content, the power of going viral on social, and how strategic relationships can open unexpected doors—like starring in a reality show. Plus, Dolmar shares his raw, inspiring journey from broke college student and balloon artist to multi-million-dollar real estate mogul, while Keisha reveals how she ghostwrites for bestselling authors and how AI is transforming her creative process. Join us for laughs, behind-the-scenes stories, and practical tips on using AI to accelerate your brand, whether you’re a content creator, business owner, or investor. And don’t miss the details about our upcoming Orlando event—it’s already almost sold out! Timeline Summary [0:00] - Kicking off happy hour: meet Dolmar & Keisha Cross from Zombie House Flipping. [2:16] - Updates on our Orlando event—VIP seats sold out, pushing for more availability. [5:44] - Brian introduces Dolmar & Keisha’s impressive backgrounds in real estate and course creation. [9:00] - Keisha shares how she uses AI to craft authentic, human-sounding ghostwritten content. [12:18] - Behind-the-scenes bloopers from filming the show, including Dolmar’s voiceover mishaps. [15:00] - Francis demonstrates creating an AI clone video using 11Labs and HeyGen in five minutes. [20:10] - Dolmar’s journey from balloon artist to a real estate entrepreneur closing over 1,000 deals. [23:31] - How investing in mentorship turned Dolmar’s early failures into a 7-figure breakthrough. [27:00] - Rebuilding the business after COVID by leveraging Instagram, leading to $10M in revenue in 18 months. [31:00] - Strategies for going viral with relatable couples content, including a video with 48 million views. [35:00] - Using AI to script creative content ideas for social media videos filmed in renovated houses. [40:10] - Plans for creating educational videos giving behind-the-scenes flipping tips while raising private capital. [47:13] - Keisha announces she’ll speak on stage for the first time ever at our Orlando event to teach AI-powered course creation. [49:00] - The power of adding value in masterminds and communities, and how relationships led to landing a reality TV show. Links & Resources Dolmar & Keisha’s Instagram: AI Tools Mentioned: and 5 Key Takeaways Humanizing AI Content – AI can create content quickly, but adding emotional nuance is critical to making it connect with real people. Relationships Drive Opportunities – Joining and giving value in masterminds can lead to game-changing introductions and opportunities, like starring on TV. Power of Relatable Content – Short, funny videos rooted in everyday experiences can go viral and attract thousands of followers. Mentorship Multiplies Success – Investing in the right mentors can transform early failures into long-term success and accelerate your path. AI Can Save Time and Scale Branding – Tools like 11Labs and HeyGen make it easy to create videos, clone voices, and generate ideas faster than ever. Closing Remark Thanks for tuning in to this episode of the AI For Business Podcast! If you enjoyed learning how Dolmar and Keisha use AI to grow their brand and business, don’t forget to rate, follow, and review the show. Share this episode with someone who wants to harness AI to transform their business—see you in the next one!
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E4: Mastering Positioning & Captivating Storytelling with 4 Time Emmy-Nominated Producer Brad Holcman
06/27/2025
E4: Mastering Positioning & Captivating Storytelling with 4 Time Emmy-Nominated Producer Brad Holcman
In this episode, we’re joined by Brad Holcman—a four-time Emmy-nominated producer known for hit shows like Duck Dynasty, Intervention, and Zombie House Flipping. Brad pulls back the curtain on the world of unscripted television, sharing his journey from A&E executive to entrepreneur and mentor, and what it really takes to create compelling content that resonates. Whether you’re a content creator, business owner, or just obsessed with storytelling, this conversation is packed with gold. Brad dives deep into the essence of storytelling—why transformation is so addictive, how to craft a memorable hook, and why your unique voice is the most valuable asset you have. He opens up about redefining success, learning to pivot in his career, and the surprising power of podcasts and AI in today’s digital world. Episode Timeline & Highlights [0:00] - Introduction [2:22] - Brad’s journey from TV executive to storytelling entrepreneur [4:04] - Why transformation stories captivate audiences—from homes to human lives [7:32] - What makes someone “TV ready” and how real relationships create hit shows [10:56] - Lessons from Duck Dynasty and the power of authenticity on screen [13:06] - The personal and professional impact of Intervention and getting Emmy-nominated [18:52] - Balancing authenticity and entertainment in reality TV [30:34] - What W-2 professionals need to know about owning their personal brand [34:11] - Why everyone has a story—and how to uncover and share yours [39:02] - The hidden power of podcasting to build trust and scale your business [44:04] - Letting go of a dream: Brad’s pivot from running a network to empowering others [50:24] - The future of creativity: Brad’s take on AI and what it means for content creators Links & Resources Zombie House Flipping on A&E 60 Days In on Netflix Real Advisors AI & Business community Brad Holcman’s daily storytelling insights on YouTube If you enjoyed this episode, please rate and review the podcast, share it with a friend, and follow to stay updated on future episodes. Thanks for listening!
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E3: The Framework for Storytelling That Converts & How Ai Creates Room for Innovation with Jason Feifer, Editor-in-Chief of Entrepreneur Magazine
06/20/2025
E3: The Framework for Storytelling That Converts & How Ai Creates Room for Innovation with Jason Feifer, Editor-in-Chief of Entrepreneur Magazine
In this episode of the AI for Business podcast, I sit down with Jason Feifer, Editor-in-Chief of Entrepreneur magazine, bestselling author, and advisor to early-stage startups. We recorded this conversation during the AI for Business Virtual Summit, and it’s easily one of the most powerful, insightful interviews we’ve had on how to stand out in an AI-saturated world. Jason shares how entrepreneurs can use strategic storytelling to make their message stick, build authentic connections in a noisy world, and apply AI to improve—not replace—human impact. He also introduces his frameworks like “bricks and mortar” storytelling, the “vertical mindset” of entrepreneurs, and why true success lies in helping people feel seen, heard, and understood. Whether you’re starting your business, scaling a brand, or exploring AI’s role in your work, this conversation is full of tactical wisdom. Episode Timeline Highlights: [0:00] Introduction [3:16] Jason shares how being around entrepreneurs transformed how he thinks about his own career [4:44] The power of vertical thinking vs. horizontal thinking in entrepreneurship [6:21] The “first question” every audience asks—and how storytelling answers it [9:12] Jason’s “bricks and mortar” framework for storytelling that converts [11:34] How AI is breaking what’s already broken—and creating room for innovation [13:06] Why lawyers fear AI (and why that’s a good thing) [15:59] The microwave oven metaphor for using AI effectively in business [17:13] Using AI for subject line testing and market research with CrowdWave [22:28] The “one thing better” mindset for simplifying AI adoption [25:38] Why starting small with AI creates momentum [27:25] The one big focus for entrepreneurs in 2024: human connection [30:03] How building community creates exponential value [31:32] Jason’s advice on building trust through simple, consistent engagement 5 Key Takeaways: Think vertically, not horizontally – Entrepreneurs don’t just create; they build each step as a foundation for the next. Use stories to stand out – Anchor your value in memorable stories that help your audience say, “This is for me.” Let AI complement, not replace – Use AI for efficiency and insight, especially where you previously had no access or time. Start with one thing better – Don’t try to learn it all at once. Master one AI tool or tactic, then build from there. Connection beats content – In a world of endless output, what people crave is real, human connection and community. Links & Resources Mentioned: Jason’s newsletter – https://www.jasonfeifer.com/newsletter CrowdWave (AI-powered market research) – https://www.crowdwave.ai CPG FastTrack (group coaching for early-stage founders) – https://www.cpgfasttrack.com Bookkeeping with AI: Kick – https://www.trykick.com Contact Jason directly – Jason Feifer on LinkedIn or reply to his newsletter Enjoyed this episode? Be sure to rate, follow, and review the podcast. If this conversation helped you think differently, share it with someone building something big with AI!
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E2: Scaling ClickUp into a $4B SaaS Empire with Chris Cunningham Co-Founder of ClickUp
06/20/2025
E2: Scaling ClickUp into a $4B SaaS Empire with Chris Cunningham Co-Founder of ClickUp
In this energizing episode of the AI for Business podcast, you’ll hear my business partner Brian Hansen in a high-impact conversation with Chris Cunningham, Co-Founder and Head of Marketing at ClickUp. Chris shares the raw, behind-the-scenes story of how ClickUp grew into a $4 billion company by thinking differently, moving fast, and staying scrappy. Recorded live during the AI for Business Virtual Summit, this session is packed with powerful insights for entrepreneurs ready to scale with AI and unconventional marketing strategies. Chris dives deep into the steps that took ClickUp from a tiny startup to one of the fastest-growing SaaS companies on the planet. From building their own lead-generation tools, to going viral on social media, to hiring intentionally and integrating AI across their business, he gives you a transparent look at what it really takes to grow fast without funding early on. Episode Timeline Highlights: [0:00] Introduction [1:30] Chris’s backstory and early lessons from a failed startup [4:20] How scrappiness became ClickUp’s competitive edge [6:01] Using negative competitor reviews to generate warm leads [7:03] The strategic customer grab that supercharged their growth [8:25] Hard lessons on hiring the wrong execs—and how to avoid it [10:20] Why standing out with bold, human marketing works [12:44] Social media strategy: how fun content built brand loyalty [14:01] Humanizing the brand like The Office meets Step Brothers [15:12] Taking small, smart marketing bets to unlock virality [18:05] Fundraising advice: when to raise and when to wait [19:17] How ClickUp replaces dozens of tools in one workspace [27:32] The AI advantage: ClickUp’s smart features in action [28:44] Why ignoring AI could put your business at risk 5 Key Takeaways: Be scrappy and creative – You don’t need big budgets to win early; you need hustle and smart tools. Stand out with your voice – Stop mimicking competitors. Be bold, be human, and be different. Leverage AI across the board – Use AI as a team multiplier for automations, messaging, and workflows. Make calculated bets – Test small, prove results, then scale what works. Don’t wait for permission. Build community and consistency – Content that entertains, educates, or connects will build lasting loyalty. Links & Resources Mentioned: ClickUp – https://www.clickup.com CoFounders Lab – https://www.cofounderslab.com Contact Chris Cunningham – [email protected] Chris Cunningham on LinkedIn – https://www.linkedin.com/in/chriscunningham Enjoyed this episode? Be sure to rate, follow, and review the podcast. If this brought you value, share it with a friend or fellow entrepreneur ready to scale with AI!
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E1: Building Billion-Dollar Startups & the Next Frontier of AI in Business with Spencer Rascoff co-founder of Zillow
06/19/2025
E1: Building Billion-Dollar Startups & the Next Frontier of AI in Business with Spencer Rascoff co-founder of Zillow
In this premiere episode of the AI for Business Podcast, I sit down with the legendary entrepreneur Spencer Rascoff, the co-founder of Zillow, Hotwire, and now a driving force behind several high-growth startups. This exclusive session, originally recorded during a private client event, pulls back the curtain on Spencer’s real-world experiences building billion-dollar businesses, navigating crises, and pioneering AI in business operations. Spencer shares unfiltered insights on startup success, building effective teams, the importance of go-to-market strategy, and why founder-market fit can make or break a company. He also breaks down the power of AI-driven productivity tools across industries, his contrarian views on crypto and real estate disruption, and the hardest part of running a multibillion-dollar company that no one talks about. Whether you’re launching your first startup or scaling your tenth, this conversation is packed with golden takeaways. Timeline Summary [0:00] – Introduction [3:11] – Why Spencer tells his Harvard students not to launch startups right away [5:07] – The #1 reason startups fail—and how to avoid it [6:08] – How to uncover great startup ideas using TAM, NPS, and personal insight [10:11] – The real story behind Spencer’s startup “Q” and how it solved a personal pain [12:34] – MVP secrets: why your first product should embarrass you [14:19] – The delicate art of knowing when to pivot—or pull the plug [17:12] – How surviving 14 near-death moments shaped Zillow’s culture [20:16] – Why storytelling and charisma matter more than code [22:05] – How Spencer reinvented his CEO role every 6-12 months [25:01] – The hidden downside of leading a 5,000-person company [27:02] – His servant leadership playbook (and why it works) [30:01] – How to hire early-stage employees who shape startup DNA [32:23] – Spencer’s top time-management hacks, including 15-minute meetings [36:14] – What he sees ahead for real estate—and how to prepare [40:58] – How AI assistants will transform productivity in every industry 5 Key Takeaways Founder-market fit is everything. Your connection to the problem you’re solving can determine your startup’s success. Great products don’t sell themselves. A strong go-to-market strategy should be built alongside your product, not after. AI co-pilots will redefine productivity. From real estate to wellness to legal, vertical-specific AI tools are the next frontier. Resilience is a founder’s superpower. Every great company faces multiple crises—how you navigate them defines your trajectory. Your team is your startup’s trajectory. Early hires set the cultural and strategic tone, so be intentional and inclusive from day one. Links & Resources Spencer Rascoff on LinkedIn: https://www.linkedin.com/in/spencerrascoff/ HeyLibby (AI Assistant for Wellness): https://www.heylibby.ai House Whisperer AI (Real Estate CRM Assistant): Email Spencer at [email protected] for access If you enjoyed this episode, please take a moment to rate, follow, and share the podcast. Your support helps us bring even more exclusive insights like this one. Thanks for tuning in!
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