Dots. | Podcast of Paul Syng

Paul Syng
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"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

  1. #32 Mike Grinberg — From Audience Engagement to Clients: Unpacking the Trust Gap for Consultants

    09/05/2025

    #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 PLATFORMS YouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5O Spotify: 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.biz READ PLATONIC BLOG https://paulsyng.com/blog/ NEED HELP WITH A COMPLEX CHALLENGE?  https://paulsyng.com __ SPEAKER LINKS Host, Paul Syng: https://x.com/paulsyng https://www.linkedin.com/in/paulsyng/ Guest, Mike Grinberg https://www.linkedin.com/in/mikegrinberg/ __ CHAPTERS 0:00 - 8:45: The Hook: De-Risking Boutiques Against Giants 8:45 - 17:32: The Trust Void: Why Engagement Fails Pipelines 17:32 - 28:05: Market Diagnostics: Align Growth with Reality 28:05 - 45:09: Sales Gravity: Questions, No's, and Proxy Busting 45:09 - 59:24: IP as Moat: From Nested Dolls to Bait-and-Switch Traps 59:24 - 1:20:18: Thought Leadership Unmasked: Outcomes Over Polish 1:20:18 - 1:39:31: The Missing Bridge: Awareness to Paid Work 1:39:31 - 1:56:35: Outreach Alchemy: Lurkers, IP Demos, and Reach Rules 1:56:35 - 2:01:31: Core Close: De-Risking for Challengers + Parenthood Paradox

    2h 2m
  2. #31 Tim Shore — Inside Tim Shore’s blogTO Origin and Exit

    08/29/2025

    #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 PLATFORMS YouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5O Spotify: 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.biz READ PLATONIC BLOG https://paulsyng.com/blog/ NEED HELP WITH A COMPLEX CHALLENGE?  https://paulsyng.com __ SPEAKER LINKS Host, Paul Syng: https://x.com/paulsyng https://www.linkedin.com/in/paulsyng/ Guest, Tim Shore https://x.com/timshore https://www.linkedin.com/in/tim-shore/ __ CHAPTERS 00:00 - Early days of blogTO and getting fired from his full-time job 5:20 - Why Tim started blogTO back in 2004 11:30 - Blogs, photoblogs and the importance of community 14:08 - Growing audience and brand awareness in the first few years 23:00 - Early signs of traction and success 36:25 - Tim's reader-first approach and saying no to advertisers 43:55 - Tim's iterative approach and responding to market disruptions 48:48 - Clickbait headlines and packaging web content 1:09:12 - blogTO's curatorial approach to covering the city 1:14:16 - The competitive landscape and respecting the reader 1:23:56 - What some competitors missed 1:26:42 - Tim's worst (but necessary?) business decisions 1:32:56 - Challenges retaining core staff and work-life balance 1:40:35 - Selling blogTO to ZoomerMedia and getting fired 1:53:35 - Closing

    1h 55m
  3. #30 Victoria Rudi — Digital Nomads, Multilingualism, and the Magic of Clear Messaging

    08/23/2025

    #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 PLATFORMS YouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5O Spotify: 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.biz READ PLATONIC BLOG https://paulsyng.com/blog/ NEED HELP WITH A COMPLEX CHALLENGE?  https://paulsyng.com __ SPEAKER LINKS Host, Paul Syng: https://x.com/paulsyng https://www.linkedin.com/in/paulsyng/ Guest, Victoria Rudi https://www.saasminds.com/ https://www.linkedin.com/in/victoriarudi/ __ CHAPTERS 00:00 Understanding Language and Bias 08:00 Crete: Greece's Self-Sufficient Gem 15:44 Reflecting on LinkedIn's Artificial Progress 16:35 "Over-Optimizing LinkedIn Posts" 25:59 Feature Prioritization and Information Architecture 27:43 Complex Software Usability Challenges 38:08 Public-Facing Software Taxonomy Explained 42:01 Zapier's Clear Communication Excellence 47:36 Emerging Regtech and Fintech Clusters 51:39 Selling Solutions, Not Products 56:17 Centralizing Decentralized Messaging 01:02:23 Effective Design in Diverse Industries 01:08:49 From Auditor to Fractional Lead

    2h 29m
  4. #29 Sara Loretta — The Secret Sauce for Business Ops

    04/07/2025

    #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 PLATFORMS YouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5O Spotify: 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 READ PLATONIC BLOG https://paulsyng.com/blog/ NEED HELP WITH A COMPLEX CHALLENGE?  https://paulsyng.com SPEAKER LINKS Host, Paul Syng: https://x.com/paulsyng https://www.linkedin.com/in/paulsyng/ Guest, Sara Loretta https://x.com/thesaraloretta https://www.linkedin.com/in/saraloretta/ CHAPTERS 00:00 Prioritizing Emotional Well-being 18:19 "Gratitude and Paying It Forward" 33:48 Perception Filters and Decisions 49:56 Empowering Solutions for Community Needs 01:12:24 "Mastering Gap-Filling in Business" 01:29:04 Viral Scandal Involving Sarah 01:42:50 "Pursuing Growth Without Virality" 01:49:38 Overcoming Self-Limiting Beliefs 02:15:15 Finding Language in Operations 02:21:21 Solopreneurship and Self-Management Goals 02:42:22 Targeted Quiz for Business Insights 02:56:44 Streamlining Work with Emojis and Ideas

    3h 5m
  5. #28 Steve Patti — From clicks to financial outcomes

    03/26/2025

    #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 PLATFORMS YouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5O Spotify: 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 READ PLATONIC BLOG https://paulsyng.com/blog/ NEED HELP WITH A COMPLEX CHALLENGE?  https://paulsyng.com SPEAKER LINKS Host, Paul Syng: https://x.com/paulsyng https://www.linkedin.com/in/paulsyng/ Guest, Steve Patti: https://www.linkedin.com/in/stevepatti/ CHAPTERS 00:00 Three Decades of Business Leadership 10:41 Rethinking Marketing Beyond Pipelines 13:23 "Product Marketing: Core Function Importance" 22:04 Marketing Career Crossroads Choices 23:27 "Embrace Change or Enhance Skills" 30:35 CMO Reporting Beyond Numbers 38:09 "Marketing's Role in Employer Branding" 39:14 Align HR and Finance for Recruitment 45:01 "Brand Accelerates Demand" 53:06 Marketing Strategies and Leadership Buy-In 57:02 "Measure Brand Marketing Effectively" 01:04:11 "New Marketing Alignment Proposal" 01:08:20 Problematic Marketing Partnership Dynamics 01:10:35 "Performance Data Disconnect"

    1h 12m
  6. #27 Cecilia Ambros — Design Leadership, Innovation and Creativity at Amazon and Nike

    11/21/2024

    #27 Cecilia Ambros — Design Leadership, Innovation and Creativity at Amazon and Nike

    Cecilia Ambros is a trained fine artist who has seamlessly transitioned from painting with colours and digital designs to "painting with data." Leveraging a versatile skill set, Cecilia embraces the challenge of learning new domains, thriving even without initial subject matter expertise. Her remarkable career has led her through unexpected opportunities, including roles at prestigious companies such as banks and Amazon. DOTS PODCAST ON ALL PLATFORMS YouTube: ⁠https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5O⁠ Spotify: ⁠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 READ PLATONIC BLOG ⁠https://paulsyng.com/blog/⁠ NEED HELP WITH A COMPLEX CHALLENGE? ⁠https://paulsyng.com⁠ SPEAKER LINKS Host, Paul Syng: ⁠https://x.com/paulsyng⁠ ⁠https://www.linkedin.com/in/paulsyng/⁠ Guest, Cecilia Ambros: https://www.linkedin.com/in/conceptualthinking/ CHAPTERS 00:00 Small studio grew; pursued MBA for job. 05:36 Missing two MBA classes; career shifts rapidly. 12:18 Differences in design approach: Nike, Amazon, Loblaws. 17:32 Observing brand adaptation, design validation differs greatly. 26:16 Nike tested gear innovations with University of Oregon. 32:21 Man's intellect challenged value of product branding. 36:50 Navigating creative differences between brands and agencies. 42:42 Nike nurtures curiosity, aligning designers across disciplines. 46:43 Understanding athlete rigor enhances design inspiration. 53:02 Nike's coaching philosophy shaped my leadership journey. 58:26 Impressed by leaders’ rapid document understanding skills. 01:03:51 Evolving client relationships through digital transformation. 01:08:33 Nike, Amazon, and Chase share service values. 01:12:28 Shattered ankle, long recovery, first hospital experience.

    1h 16m
  7. #26 Josh Lowman — From copywriter to category design studio

    10/22/2024

    #26 Josh Lowman — From copywriter to category design studio

    Josh Lowman founded Gold Front, an agency that’s helped major players like Stripe, Uber, and Clari carve out new market categories. Josh and his team focus on business strategy, positioning, and brand design, working with top CEOs, founders, and CMOs who want to be different in their industries. But that’s not all. Josh is also passionate about sharing his insights for free through his newsletter, LinkedIn, and live workshops. When he’s not shaping the future of tech brands, you can find him hanging out with his daughters or rooting for the Detroit Lions—a test of loyalty if there ever was one! DOTS PODCAST ON ALL PLATFORMS YouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5O Spotify: https://open.spotify.com/show/2z0Vgy7eNR6XSk3M0uSugp?si=eb5369dea4314099  Apple: https://podcasts.apple.com/us/podcast/dots-podcast-of-paul-syng/id1557392269   Anchor: https://podcasters.spotify.com/pod/show/paulsyng READ PLATONIC BLOG https://paulsyng.com/blog/ NEED HELP WITH A COMPLEX CHALLENGE?  https://paulsyng.com SPEAKER LINKS Host, Paul Syng: https://x.com/paulsyng https://www.linkedin.com/in/paulsyng/ Guest, Josh Lowman: https://www.linkedin.com/in/joshlowman/ Gold Front | Apex - Case Study https://www.goldfront.com/work/real-performance-apex CHAPTERS 00:00 Welcome Josh Lowman 02:38 How Josh created Gold Front (A category design studio) 11:53 Connecting the dots from strategy to execution 22:14 Category vs 'Brand' and why words you use matter 29:55 Positioning in category strategy 36:27 One thing that drives Josh about Gold Front 40:11 Apex case study 44:25 Working with founders and CEOs 50:07 3001 Questions all about me

    53 min
  8. #25 Alex Smith — The No B******t Strategy Guy

    10/03/2024

    #25 Alex Smith — The No B******t Strategy Guy

    Alex Smith is a strategist, writer, and advisor to CEOs and founders. He is the founder of Basic Arts, and he helps create brands that stand alone in their markets and bring true value to people. It’s my goal to increase strategic understanding and expertise among founders since it’s not only widely misunderstood but often completely overlooked. DOTS PODCAST ON ALL PLATFORMS YouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5O Spotify: https://open.spotify.com/show/2z0Vgy7eNR6XSk3M0uSugp?si=eb5369dea4314099  Apple: https://podcasts.apple.com/us/podcast/dots-podcast-of-paul-syng/id1557392269   Anchor: https://podcasters.spotify.com/pod/show/paulsyng READ PLATONIC BLOG https://paulsyng.com/blog/ NEED HELP WITH A COMPLEX CHALLENGE?  https://paulsyng.com SPEAKER LINKS Host, Paul Syng: https://x.com/paulsyng https://www.linkedin.com/in/paulsyng/ Guest, Alex Smith: https://www.linkedin.com/in/alex-m-h-smith/ 00:00:00 Meet Alex, monetize your quirks 00:03:42 Alex's unconventional path to strategy 00:15:03 An act of mischief 00:28:07 Elephant, monkey and a fish climb a tree 00:35:34 No one is buying strategy 00:43:15 What is 'strategy' and understanding founder motivations 00:55:33 Understand the person and their context first 01:05:17 Positioning and Simon Sinek's 'Why?' 01:14:26 Fame ≠ expertise 01:32:05 How Alex built an audience of 90k on LinkedIn 01:48:47 3001 Questions all about me

    1h 54m
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"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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