#32 Mike Grinberg — From Audience Engagement to Clients: Unpacking the Trust Gap for Consultants
Mike Grinberg is passionate about meaningful engagement and the power of a clear narrative. Rather than just posting for the sake of attention, Mike believes that every message—whether humorous or insightful—should support a bigger purpose and encourage others to see their challenges in a new light. For Mike, it’s not about being everywhere all at once, but about building trust and bringing a strong point of view that truly resonates. Otherwise, as he says, you risk becoming just another voice in the noise—unless, of course, your calling is to be a comedian.__DOTS PODCAST ON ALL PLATFORMSYouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5OSpotify: https://open.spotify.com/show/2z0Vgy7eNR6XSk3M0uSugp?si=eb5369dea4314099 Apple: https://podcasts.apple.com/us/podcast/dots-podcast-of-paul-syng/id1557392269 Podcasters: https://podcasters.spotify.com/pod/show/paulsyng__GRAB YOUR CEO CLARITY STARTER KIT http://claritytoscale.bizREAD PLATONIC BLOGhttps://paulsyng.com/blog/NEED HELP WITH A COMPLEX CHALLENGE? https://paulsyng.com__SPEAKER LINKSHost, Paul Syng:https://x.com/paulsynghttps://www.linkedin.com/in/paulsyng/Guest, Mike Grinberghttps://www.linkedin.com/in/mikegrinberg/__CHAPTERS0:00 - 8:45: The Hook: De-Risking Boutiques Against Giants8:45 - 17:32: The Trust Void: Why Engagement Fails Pipelines17:32 - 28:05: Market Diagnostics: Align Growth with Reality28:05 - 45:09: Sales Gravity: Questions, No's, and Proxy Busting45:09 - 59:24: IP as Moat: From Nested Dolls to Bait-and-Switch Traps59:24 - 1:20:18: Thought Leadership Unmasked: Outcomes Over Polish1:20:18 - 1:39:31: The Missing Bridge: Awareness to Paid Work1:39:31 - 1:56:35: Outreach Alchemy: Lurkers, IP Demos, and Reach Rules1:56:35 - 2:01:31: Core Close: De-Risking for Challengers + Parenthood Paradox
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#31 Tim Shore — Inside Tim Shore’s blogTO Origin and Exit
Tim Shore is the visionary founder of blogTO, Toronto's premier digital media platform for local news, culture, and events, which he launched in 2004 as a side hustle while working in advertising. His passion for the project grew so intense that it led to his firing from his day job, prompting him to go all-in and transform blogTO into Canada's largest independent blog of its kind. Drawing from early experiences as a CNN intern and managing digital campaigns for brands like Yahoo! and Microsoft, Tim scaled the site to millions of monthly users. In January 2022, he sold blogTO to ZoomerMedia for $15 million, marking a pinnacle of success — only for his journey to come full circle when the company terminated him on March 25, 2025. In this episode, Tim shares candid reflections on resilience, building a media empire from scratch, navigating viral content strategies, and advice for aspiring entrepreneurs and side hustlers eyeing the digital space.__DOTS PODCAST ON ALL PLATFORMSYouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5OSpotify: https://open.spotify.com/show/2z0Vgy7eNR6XSk3M0uSugp?si=eb5369dea4314099 Apple: https://podcasts.apple.com/us/podcast/dots-podcast-of-paul-syng/id1557392269 Podcasters: https://podcasters.spotify.com/pod/show/paulsyng__GRAB YOUR CEO CLARITY STARTER KIT http://claritytoscale.bizREAD PLATONIC BLOGhttps://paulsyng.com/blog/NEED HELP WITH A COMPLEX CHALLENGE? https://paulsyng.com__SPEAKER LINKSHost, Paul Syng:https://x.com/paulsynghttps://www.linkedin.com/in/paulsyng/Guest, Tim Shorehttps://x.com/timshorehttps://www.linkedin.com/in/tim-shore/__CHAPTERS00:00 - Early days of blogTO and getting fired from his full-time job5:20 - Why Tim started blogTO back in 200411:30 - Blogs, photoblogs and the importance of community14:08 - Growing audience and brand awareness in the first few years23:00 - Early signs of traction and success36:25 - Tim's reader-first approach and saying no to advertisers43:55 - Tim's iterative approach and responding to market disruptions48:48 - Clickbait headlines and packaging web content1:09:12 - blogTO's curatorial approach to covering the city1:14:16 - The competitive landscape and respecting the reader1:23:56 - What some competitors missed1:26:42 - Tim's worst (but necessary?) business decisions1:32:56 - Challenges retaining core staff and work-life balance1:40:35 - Selling blogTO to ZoomerMedia and getting fired1:53:35 - Closing
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#30 Victoria Rudi — Digital Nomads, Multilingualism, and the Magic of Clear Messaging
Victoria Rudd is a multilingual adventurer guided by perseverance and curiosity. Though English is not her native tongue, she uses it with ease and humor. The journey took a sharp turn when she moved to Spain for her master's degree, assured that all courses would be in English. On arrival, she discovered everything was taught in Spanish, and the Spanish classes clashed with her core courses. Faced with this unexpected challenge, Victoria dove headfirst into the language, mastering Spanish out of necessity to thrive in both academia and daily life. Her story is further colored by earlier language experiences—French being the first foreign language she learned—making her language journey one shaped by adaptability, resilience, and a willingness to embrace the unknown.__DOTS PODCAST ON ALL PLATFORMSYouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5OSpotify: https://open.spotify.com/show/2z0Vgy7eNR6XSk3M0uSugp?si=eb5369dea4314099 Apple: https://podcasts.apple.com/us/podcast/dots-podcast-of-paul-syng/id1557392269 Podcasters: https://podcasters.spotify.com/pod/show/paulsyng__GRAB YOUR CEO CLARITY STARTER KIT http://claritytoscale.bizREAD PLATONIC BLOGhttps://paulsyng.com/blog/NEED HELP WITH A COMPLEX CHALLENGE? https://paulsyng.com__SPEAKER LINKSHost, Paul Syng:https://x.com/paulsynghttps://www.linkedin.com/in/paulsyng/Guest, Victoria Rudihttps://www.saasminds.com/https://www.linkedin.com/in/victoriarudi/__CHAPTERS00:00 Understanding Language and Bias08:00 Crete: Greece's Self-Sufficient Gem15:44 Reflecting on LinkedIn's Artificial Progress16:35 "Over-Optimizing LinkedIn Posts"25:59 Feature Prioritization and Information Architecture27:43 Complex Software Usability Challenges38:08 Public-Facing Software Taxonomy Explained42:01 Zapier's Clear Communication Excellence47:36 Emerging Regtech and Fintech Clusters51:39 Selling Solutions, Not Products56:17 Centralizing Decentralized Messaging01:02:23 Effective Design in Diverse Industries01:08:49 From Auditor to Fractional Lead
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#29 Sara Loretta — The Secret Sauce for Business Ops
Sara Loretta is an entrepreneur, digital strategist, and operations consultant based in Austin, Texas. She is the founder and Chief Digital Architect of SYSTMS™, a consultancy specializing in helping service-based businesses streamline their workflows and scale effectively. With over a decade of experience in data management, compliance, and business development, Sara focuses on designing tools and strategies to support asynchronous and remote work environments globally.DOTS PODCAST ON ALL PLATFORMSYouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5OSpotify: https://open.spotify.com/show/2z0Vgy7eNR6XSk3M0uSugp?si=eb5369dea4314099 Apple: https://podcasts.apple.com/us/podcast/dots-podcast-of-paul-syng/id1557392269 Podcasters: https://podcasters.spotify.com/pod/show/paulsyngREAD PLATONIC BLOGhttps://paulsyng.com/blog/NEED HELP WITH A COMPLEX CHALLENGE? https://paulsyng.comSPEAKER LINKSHost, Paul Syng:https://x.com/paulsynghttps://www.linkedin.com/in/paulsyng/Guest, Sara Lorettahttps://x.com/thesaralorettahttps://www.linkedin.com/in/saraloretta/CHAPTERS00:00 Prioritizing Emotional Well-being18:19 "Gratitude and Paying It Forward"33:48 Perception Filters and Decisions49:56 Empowering Solutions for Community Needs01:12:24 "Mastering Gap-Filling in Business"01:29:04 Viral Scandal Involving Sarah01:42:50 "Pursuing Growth Without Virality"01:49:38 Overcoming Self-Limiting Beliefs02:15:15 Finding Language in Operations02:21:21 Solopreneurship and Self-Management Goals02:42:22 Targeted Quiz for Business Insights02:56:44 Streamlining Work with Emojis and Ideas
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#28 Steve Patti — From clicks to financial outcomes
Steve Patti is a seasoned marketing strategist with over 35 years of extensive experience. He has navigated a successful career marked by three significant phases. The journey began with a decade dedicated to working within diverse enterprise environments, ranging from small businesses to a Fortune 500 tech giant generating $5 billion in revenue. Building on this foundation, Steve launched a marketing consulting firm, scaling it impressively from zero to $20 million within three years, collaborating with prominent brands such as Visa, Intel, American Express, and Dell. The most recent chapter of this career has been characterized by roles as a growth advisor, serving as a full-time or fractional CMO and undertaking strategic growth roles that bridge sales and marketing for companies with revenues up to $160 million. This blend of corporate, entrepreneurial, and advisory experience showcases a profound expertise in driving growth and innovation.DOTS PODCAST ON ALL PLATFORMSYouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5OSpotify: https://open.spotify.com/show/2z0Vgy7eNR6XSk3M0uSugp?si=eb5369dea4314099 Apple: https://podcasts.apple.com/us/podcast/dots-podcast-of-paul-syng/id1557392269 Podcasters: https://podcasters.spotify.com/pod/show/paulsyngREAD PLATONIC BLOGhttps://paulsyng.com/blog/NEED HELP WITH A COMPLEX CHALLENGE? https://paulsyng.comSPEAKER LINKSHost, Paul Syng:https://x.com/paulsynghttps://www.linkedin.com/in/paulsyng/Guest, Steve Patti:https://www.linkedin.com/in/stevepatti/CHAPTERS00:00 Three Decades of Business Leadership10:41 Rethinking Marketing Beyond Pipelines13:23 "Product Marketing: Core Function Importance"22:04 Marketing Career Crossroads Choices23:27 "Embrace Change or Enhance Skills"30:35 CMO Reporting Beyond Numbers38:09 "Marketing's Role in Employer Branding"39:14 Align HR and Finance for Recruitment45:01 "Brand Accelerates Demand"53:06 Marketing Strategies and Leadership Buy-In57:02 "Measure Brand Marketing Effectively"01:04:11 "New Marketing Alignment Proposal"01:08:20 Problematic Marketing Partnership Dynamics01:10:35 "Performance Data Disconnect"
"You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever." — Steve Jobs
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