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Stephanie Nakano operated a side of community the industry rarely discusses: the internal community for Salesforce and Slack. Her work focused on employee culture, conduct, confidentiality, and trust and safety for the company's 70,000 employees. Incidents affected people's wellbeing and the company's exposure to reputational and legal risks which could run in the millions of dollars and above.
We talk about building an operating system for trust between leaders and employees, establishing governance and principles, securing leadership buy-in, and acting with full awareness of the trade-offs inherent in high-stakes decisions.
This conversation covers the nuts and bolts of the job, building an early-warning sensing function, the value of trust, and the emotional cost to professionals in roles like hers. Stephanie gives the exact language that moves an executive to fund the work, what words don't work, and the reframe she's used over and over with leaders that help them back the tough calls.
Key Themes
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Links
About Tim
Tim works with leadership teams on community product strategy and co-creation programs. If this episode sparked something for your team, get in touch at roundabout.community.
At 17, Bjarne Tveskov answered a newspaper ad for a LEGO spaceship designer, quit school, and never went back. He designed the Monorail, early Blacktron sets, and helped shape LEGO's first digital products. Decades later, he prototyped Smart Brick concepts from his basement using childhood bricks alongside new ones. Every piece still connects.
This conversation maps the arc from bricks to digital tools to AI, held together by one idea: the best creative work happens at the resolution of imagination, not photorealism. Bjarne makes the case that repetition is a creative practice, point of view is the new competitive advantage, and weirdness might be the most valuable thing humans bring to a world of averaged-out content.
Key Themes
Key Takeaways
Chapters
03:07 - Becoming a LEGO Designer at 17
05:53 - The Birth of LEGO Space Factions
10:35 - Designing the Futuron Monorail
14:49 - LEGO Space Culture and the Internet
21:57 - LEGO Minecraft: From Viral Demand to Product
36:07 - Finding Joy in Repetition
39:00 - From Bricks to Digital: LEGO Darwin and Mindstorms
47:28 - The Smart Brick and Design Resolution
53:01 - Technology, Culture, and the Internet's Evolution
57:20 - Missing the Old Internet
1:02:18 - What Holds Value in the AI Era
1:06:05 - Vibes, Data Bankruptcy, and Human Feeling
1:16:09 - Bjarne's Red Thread: Combining Existing Elements
Links
About Tim
Tim works with leadership teams on community product strategy and co-creation programs. If this episode sparked something for your team: [email protected]
Thaniya Keereepart has spent 20+ years at the intersection of product, community, and behavioral economics, from MLB's first live streaming app to TED's founding head of product, scaling TED from 500K to 2 billion video views and building TEDx. She's navigated the tension between what a brand wants to be and what its community needs it to become at Patreon, Harvest, the Athletic, and MetaLabel.
Themes:
Takeaways:
Chapters:
2:14 - Growing Up on Airplanes
6:40 - Dreams Worth Helping to Actualize
13:25 - Building MLB's Live Streaming Product from Scratch
18:25 - TED's Founding Head of Product
20:59 - The Birth of TEDx
30:37 - Community as Brand Amplifier
34:54 - The Athletic and Sports Journalism's Future
45:12 - Harvest and the Business Case for Generosity
52:57 - The Circular Relationship Between Product and Community
58:50 - The Product Liaison Role
1:06:07 - MetaLabel and Artist Corporations
1:20:37 - AI and What Endures
1:28:51 - The Roundabout Brand Story
Links:
About Tim:
Tim works with leadership teams on community product strategy and co-creation programs. If this episode sparked something for your team: [email protected]
Customer experience isn't customer service with a bigger budget. It's the operating system. Jeannie Walters has spent two decades proving that to Fortune 500 teams, and her book Experience is Everything codifies the playbook.
Tim and Jeannie dig into what happens when CX leaders drive change from the middle of an org chart, why your B2B customers compare you to Uber, and how trust builds or erodes at scale.
Key Themes
Key Takeaways
Your customers compare you to every experience they've had, not just your competitors.
Start with a CX mission statement for your team. Results spread by osmosis.
Ask executives when they last talked to a customer. The discomfort opens the conversation.
Build feedback loops for frontline workers. They see problems before dashboards do.
Frustration is anger without control. Design for reassurance and agency at risk points.
Trust at scale requires systems: conscience, communication, consistency, credibility.
Chapters
02:29 - Origins in the Social Media Era
07:02 - The Story Behind the Book
09:25 - The Influence Problem
14:18 - Customer Service vs. Customer Experience
19:38 - Customer Experience as Innovation
24:41 - Making the Case with Tight Resources
28:47 - Mission Statements That Work
36:12 - Jeannie's Executive Worksheet Trick
41:53 - Building a CX Culture
50:19 - Moments of Truth
53:25 - The CX Case for your CFO
58:10 - The Four Cs of Trust
1:03:59 - Placing Customer Experience on the Org Chart
1:06:32 - Clarity Over Perfection
1:12:08 - Community is Downstream of Experience
1:19:56 - The Future of Customer Experience
1:23:11 - AI and Customer Experience
1:29:08 - Trust in a Cynical World
1:31:17 - Connecting with Jeannie
Links
About Tim
Tim works with leadership teams on community product strategy and co-creation programs. If this episode sparked something for your team: [email protected].
Steve Jennings has been building for four decades. Competitive cyclist turned founder of Maxim (Europe's top sports nutrition brand), then PepsiCo, open innovation, and now Jenerise, a creatine company co-founded with his daughter Rachael.
We cover why comfort kills your edge, how endurance sport trained him for entrepreneurship, building consumer community before the internet, and how brands must go all-in to win at open innovation. Steve tells the creatine origin story: a bag of white powder handed to him in a hotel, 47 days to a finished product and gold medals at Barcelona 1992. We close with how he's using agentic AI to de-risk product market fit.
Key Themes
Key Takeaways
Chapters
02:39 - The Drive to Keep Building
06:47 - Thriving on Chaos and Uncertainty
10:59 - Cycling as Entrepreneurial Training Ground
19:10 - Regulating as a High-Energy Founder
25:05 - Five Pillars of Everyday Human Performance
32:21 - Building a Consumer Community Before the Internet
39:58 - Product as the Catalyst for Conversations
46:21 - LEGO Ideas and Open Innovation
49:11 - Why Brands Don't Go All In on Community
57:14 - You Have to Invite Customers into the Brand
1:02:14 - The Creatine Origin Story: Barcelona 1992
1:15:21 - Creatine Beyond Sports: Cognition and Longevity
1:19:55 - Building Jenerise with Daughter Rachael
1:25:02 - The Whitespace in the Creatine Market
1:28:04 - Agentic AI for De-Risking Innovation
1:38:20 - It's Always Human First
Links
- Steve Jennings on LinkedIn
- Jenerise
- Scientists may keep UK athletes one step ahead
- The Untold Story Behind Creatine, and How I Played a Pivotal Role In It Becoming a Global Supplement Phenomenon
About Tim
Tim works with leadership teams on community product strategy and co-creation programs. If this episode sparked something for your team: [email protected]
Julie Mossler built the comms function at Groupon through its IPO, ran brand at Waze through the Google acquisition, and has been a four-time CMO across web2.0, crypto, and AI. Now she runs Common Fortune, advising founders on go-to-market and category building.
This conversation covers building brands from the inside out, why small cross-functional teams outperform org charts, what AI is doing to marketing roles, and why attention might be the last real moat.
Key Themes
Culture builds the brand, not the other way around. Groupon's voice came from comedy writers and improv actors. Julie built Groupon's PR prowess on top of that culture, where most comms teams rein in their creatives.
Speaking of reins, AI might be automating more and more operations, but it will never know when to put the pony in the freight elevator.
Small teams with decision-making authority multiply output. The best ideas aren't limited to roles, titles, silos, or seniority.
AI is collapsing junior roles, not eliminating marketing. One hire who builds agents replaces the headcount that used to do copywriting. The CMO of the future builds tools and tells stories.
Sycophantic AI tells you your ideas are great. Real strategy can't be prompted. Read the zeitgeist, make bets, and learn from mentors who've honed their skills over decades.
Attention is the last moat. Anyone can ship a product or press release; the differentiator is getting people to care and to keep coming back.
Key Takeaways
Chapters
00:00 - Introduction
01:38 - The Collapse and Rebirth of Media
05:14 - Journalists Learning to Vibe Code
06:46 - How Julie Picks Winners
09:20 - Inside Groupon's Editorial Machine
14:07 - Improv Actors in Customer Service
19:38 - The Pony in the Freight Elevator
22:23 - Categories Worth Watching Now
28:46 - Small Cross-Functional Teams and Leveraging Volunteers at Waze
36:52 - Where the Junior Roles Go
40:20 - Strategy Can't Be Prompted
43:33 - Campaigns End, Infrastructure Compounds
48:56 - The Ethics of AI Tool Choices
53:10 - Human Skills Julie is Long On
58:01 - We Shape Our Tools, And Thereafter They Shape Us
1:01:15 - Don't Build a Ferrari to go to the Grocery Store
1:03:10 - Attention Is the Last Moat
1:06:07 - Julie's Novel and Accountability Time
1:09:16 - Limitless Possibility
Links
About The Host
Tim Courtney works with leadership teams on community product strategy and co-creation programs. If this episode sparked something for your team, get in touch: http://roundabout.community.
LEGO® IDEAS turned fan creativity into a nine-figure product line. But the hard part wasn't the platform, it was integrating a disruptive innovation engine into an 80-year-old organization without killing the trust with users that made it work. Daiva Naldal led that integration, designing the systems that scaled a Japanese-language experiment into a global business, alongside host Tim Courtney who led Community and Experience for IDEAS between 2011-2018.
Tim and Daiva trace the arc from LEGO's near-bankruptcy in the mid-2000s through the first LEGO Minecraft set that hit its vote threshold in 24 hours, and beyond. They share the structural decisions that made scaling possible, and the willingness to walk away from commercial opportunities to protect community trust.
The views expressed by the host and guest are their own and do not represent those of any current or former employer. LEGO® is a trademark of the LEGO Group of companies which does not sponsor, authorize or endorse this podcast.
Key Takeaways
Chapters
0:00 - Show Intro
02:10 - Daiva's LEGO Journey and the New Business Group
04:46 - The Muji Experiment and LEGO Architecture Origins
06:37 - Finding Innovation as a Craft
08:59 - The Wild West of LEGO CUUSOO
15:32 - Minecraft: When Fans Read the Market First
18:39 - Building the First LEGO Minecraft Set
22:27 - LEGO's Near-Bankruptcy and the Return to DNA
26:39 - Making Innovation Relevant to the Organization
28:58 - Closing the Circle: From Fans, For Fans
33:28 - Building Trust at Scale
36:28 - The Participation Promise
39:44 - Capabilities the Organization Gained
43:50 - Open Innovation Beyond LEGO
46:35 - Principles for Early-Stage Founders
53:31 - Scaling Mistakes Founders Make
58:35 - AI, Human Foresight, and What Stays Valuable
1:03:14 - Three Takeaways That Click
Links
Danielle Baskin calls herself a situation designer — someone who creates bounded, episodic experiences that put people in novel interactions.
From staging a fake 7-Eleven onigiri launch that generated news coverage, to running BART Basel, a rogue art show that roams subway platforms, Danielle has built a playbook for manufacturing belief, testing ideas in public, and building cult followings without big marketing spend.
Danielle and Tim unpack how constraints drive creative output, her methods for validating ideas, and what her voice-based social app Dialup revealed about human connection — including how anonymous phone calls between strangers changed political beliefs.
The episode closes with a sharp exchange on AI's effect on cognition, relationships, and professional identity, and Danielle's take on what becomes more valuable when everything can be optimized.
Key Themes
Business theater as demand generation. Danielle didn't petition 7-Eleven or tweet at their brand account. She built a world where onigiri already existed at 7-Eleven and let people's excitement prove the market.
Permission structures and participation. BART Basel's irreverence gave hundreds of people permission to present art, tell stories, and be earnest without the gatekeeping of a gallery or application. The format creates the fans.
Constraints as creative engine. No advance notice, no large budgets. Danielle chooses creative constraints that keep her execution flexible.
Manufacturing belief and earning it. Danielle's work demonstrates the best satire is uncomfortably believable, and the reaction to it reveals latent demand, desire, or anxiety.
Human connection by design. Dialup (90K users, voice-based, anonymous) and Moonlight (interactive tarot platform, thousands of daily users) both create containers for deeper conversation — structured enough to feel safe, open enough to surprise.
AI, identity, and the moat of curiosity. Danielle's take: AI is eroding logical reasoning and gut intuition. The moat for creators is staying curious about things with unknown outcomes.
Key Takeaways
Links
"People who can’t build spend most of their time trying to keep their job."
"Give the product to the people who can build it and care most about it."
Steven Walker has led design at Groupon and Quirky, some of the fastest growth stories of the web2.0 era. In this conversation we explore what actually makes products succeed under extreme pressure. Great products are rarely the result of process or hierarchy. Rather they emerge from strong teams, tight relationships, and builders empowered to execute their ideas.
Throughout the episode, Walker shares a consistent philosophy: the people closest to the work should own it. Designers and builders who can prototype and test ideas outperform organizations built around layers of management and coordination.
We also zoom out to larger questions about technology, education, and the role of craft in an AI-driven world. While automation will accelerate many parts of product development, Walker believes the human elements of relationships, community, and hands-on learning will become even more valuable.
We Explore
* Design Leadership in Hypergrowth - What it means to lead product and design while scaling from scrappy startup to global platform, including hiring and firing fast, and relentlessly protecting team quality.
* Builders vs. Managers - Builders who can prototype ideas outperform organizations where managers make the call.
* Relationships as Infrastructure - High-performing teams are built on trust and strong relationships, not reporting structures.
* Crowdsourcing Innovation - Platforms like Quirky and LEGO Ideas reveal how communities can surface and refine product ideas.
* Signal vs. Noise in High Growth Enviroments - The hardest challenge during hypergrowth is filtering valuable insight from massive volumes of input.
* Technology, Craft, and the Human Renaissance - As AI automates knowledge work, hands-on skills, education, and human connection become more important. Teaching people to build and understand systems creates deeper understanding than passively consuming technology or content.
Chapters
06:15 The Internet: A New Era of Knowledge Transfer
09:01 Groupon and the Rise of Designers who Code
19:00 What Changed After Groupon's IPO
22:09 Great Teams Come From Great Relationships
26:32 Quirky and Crowdsourcing Consumer Products
37:37 Give Ownership to Builders, not Managers
41:56 Wasted Time as a Metric
45:44 AI, Craft, and the Coming Renaissance
51:24 Maintaining Real-World Know-How
53:35 The Foundations of Strong Communities
58:22 Designer Fund: Investing in Desgin-Led Companies
01:04:40 Teaching Kids to Build: The Antidote to Screens
Links
Steven Walker https://www.linkedin.com/in/walkersteven/
Andrew Mason https://en.wikipedia.org/wiki/Andrew_Mason
Charles Adler https://charles-adler.com/
Designer Fund https://designerfund.com
Stripe https://stripe.com
More episodes: [http://roundabout.community/show
She moved to San Francisco knowing almost no one.
Three years later, she’d raised $9M and built one of the strongest operator networks in the city.
In this episode, I sit down with Vera Maslova, a partnership and fundraising specialist who moved to the Bay Area without an existing network and built one deliberately.
Since arriving, Vera has:
• Raised over $9M
• Convened dozens of curated founder dinners and small gatherings
• Built trusted relationships with CTOs, investors, and operators
• Served on nonprofit boards and developed long-term strategic partnerships
Years before she moved, Vera built a list of more than 300 people she wanted to meet. When she arrived, she started reaching out. Sometimes she followed up for two years. If someone didn’t explicitly say no, she stayed in motion.
Her dinners are curated environments: ten to twelve people, cross-disciplinary, high generosity, low performance. She sets the tone intentionally, inviting ease, curiosity, and depth.
We explore:
• Why most new relationships fade at the second touchpoint
• The difference between the market of attention and the market of trust
• Follow-up strategy
• Why consistency compounds faster than charisma
• How curated rooms outperform large ones
• What AI can amplify, and what it cannot replace
This conversation looks at trust: how it’s built, how it compounds, and how it becomes durable advantage in an automated, distracted world.
If you build products, teams, or ecosystems, the question isn’t visibility. It’s where you are intentionally designing trust.
Chapters
02:14 The Importance of Connection
10:19 Building Trust and Professional Relationships
18:57 The Power of Curated Gatherings
21:42 Follow-Up as Strategy
25:15 Consistency as Competitive Advantage
28:05 Tools for Building Relationships
29:23 The Hidden Trust Landscape
30:56 Authenticity in Professional Contexts
33:54 Cultivating Advocacy Through Relationships
36:42 Trust as Compounding Capital
39:41 Navigating Distrust in Society
43:08 Leading by Example
44:33 The Role of Mentorship
47:27 The Courage to Ask for Mentorship
52:11 Designing Memorable Experiences
56:35 When Intelligence Becomes Cheap
57:17 The Nature of Intelligence and AI
01:00:01 AI as Tool, Not Substitute
01:00:48 Listening as Leverage
01:04:22 Fundamentals of Human Connection
01:07:49 Building Relationships in a Digital Age
Links
Boardy – AI Connection Platform – https://boardy.ai
The Culture Map by Erin Meyer – https://www.amazon.com/Culture-Map-Understanding-Global-Workplace/dp/1625276522
How I Built This Podcast by Guy Raz – https://www.npr.org/sections/how-i-built-this/
Gustavo Dudamel – Conductor – https://en.wikipedia.org/wiki/Gustavo_Dudamel
Guest Profile
LinkedIn – https://www.linkedin.com/in/vera-maslova
More episodes:
http://roundabout.community/show
From the publisher's feed
Conversations at the intersection of creators, community, and customer experience.
The Roundabout Show explores how community, customer experience, and creator ecosystems drive…
Host Tim Courtney is a community product strategist who helps companies build with their most engaged users. He was the founding Community and Experience lead for LEGO IDEAS, scaling a creator platform from beta to over a million members and $100 million in crowdsourced product revenue from LEGO fans' designs that became real products on store shelves.
In each episode, Tim talks with creators, builders, and leaders about what happens when you design for trust, participation, and belonging — and the business outcomes that follow: stronger loyalty, lower acquisition costs, and long-term brand equity.
Topics include community product strategy, co-creation programs, creator ecosystems, customer experience, the intersection of AI and human judgment, and people-first growth.
Tim works with leadership teams on community product strategy and co-creation programs. If an episode sparks something for your team: [email protected]
Learn more: roundabout.community/show