Dots. | Podcast of Paul Syng

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.

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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

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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

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SPEAKER LINKS
Host, Paul Syng:
https://x.com/paulsyng
https://www.linkedin.com/in/paulsyng/

Guest, Mike Grinberg
https://www.linkedin.com/in/mikegrinberg/

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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

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.

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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/

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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

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.

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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/

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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

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

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"