A Digital Strategy Podcast

Tennis
  • 0.0 (0)
  • Management
  • Updated Biweekly

A Digital Strategy Podcast explores how design, technology, and business intersect to shape the way organizations grow and adapt. Through thoughtful discussions and interviews with leaders in tech, design, brand, and marketing, the show shares practical strategies, frameworks, and stories for navigating today’s digital landscape. Hosted by the team at Tennis, the podcast blends sharp takes on the industry with candid conversations about the systems, tools, and decisions that drive lasting impact.

  1. 15h ago

    People Are Using AI to Sue Websites Over Bad Design

    Before you even listen to this, scan your website here to know if you're accessible:https://www.designtennis.com/design-and-business-resources/website-accessibility-guide Most businesses think an accessibility lawsuit is something that happens to someone else. Then AI hands anyone with a browser the ability to file one. In this episode, Symon and Marcello unpack the sharp rise in ADA website lawsuits in the US—and why AI is the reason the numbers are exploding. They get into how AI has collapsed the barrier to filing, why Q1 2026 nearly matched all of 2025, the DOJ's last-minute reversal that pulled healthcare back into the compliance deadline, and why the one-shot AI tools and accessibility widgets people are counting on won't save them. Plus: why e-commerce keeps taking the brunt of it, the Ontario December 31 reporting deadline nobody's talking about, and why an audit is where you start—not where you finish. A web-first look at where accessibility law is heading, for organizations that would rather get ahead of this than get a demand letter. 💡 Key Topics: How AI lowered the barrier to entry for ADA claims, turning individuals into self-represented (pro se) plaintiffs Why Q1 2026 filings (3,500–4,500) nearly matched all of 2025 in a single quarter The rise of pro se lawsuits and the digital fingerprints—hallucinations included—that reveal they're AI-generated Why ADA web cases jumped from 28% of Title III filings to 36% The DOJ's four-days-before-the-deadline reversal that folded healthcare back into public-entity compliance The new targets: April 26 2027 for large entities, April 26 2028 for small ones, both on WCAG AA Why one-shot AI remediation tools and accessibility overlay widgets create more problems than they solve Why e-commerce absorbs roughly 69% of accessibility lawsuits The Ontario December 31 compliance reporting deadline and how self-reporting puts you in the queue Why an audit is a starting indicator, not a solution—and where manual testing has to take over 📖 Chapters: 0:07 — Intro: AI plus compliance 0:43 — How AI lowered the barrier to ADA claims 2:32 — The numbers: Q1 2026 vs. all of 2025 3:20 — Pro se lawsuits and AI's digital fingerprints 5:31 — The DOJ healthcare deadline reversal 7:31 — New compliance dates and the WCAG AA standard 8:00 — Why AI tools and widgets won't save you 8:37 — Why e-commerce takes the brunt 9:36 — Weaponized lawsuits and the chilling effect on cross-border business 10:00 — What to actually do: the Ontario Dec 31 deadline and the audit 11:01 — Audit, but find an expert: where tools fall short 🌐 Tennis web accessibility services: https://www.designtennis.com/services/website-design-and-development 🎧 Spotify: https://open.spotify.com/show/7tufP8mSXC1YrLxrLzw3Ju?si=3839798c83264d9b 📸 Instagram: Tennis.digital 💼 LinkedIn: https://www.linkedin.com/company/designtennis/?viewAsMember=true 🔔 Subscribe for weekly episodes on web design, digital strategy, and building better businesses. #accessibility #ADA #ADAcompliance #WCAG #webaccessibility #a11y #webdesign #compliance #ecommerce #b2bdesign #webdevelopment #inclusivedesign #digitalstrategy #websitedesign #AIlawsuits Links You can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

    People Are Using AI to Sue Websites Over Bad Design

  2. Jul 10

    50 Employees? Your Website Is Probably Breaking the Law

    💡 Key Topics: What AODA actually covers on the web, and why it applies to all public websites and content if you have 50+ employees in Ontario WCAG 2.0 Level AA as the current legal floor, and why 2.1 and 2.2 matter even if the law hasn't caught up The compliance report trap: how self-reporting non-compliance gets you audited within weeks How compliance officers really operate, and why they reward engaging a consultant with a real timeline Why remediation and redesign are different, and how a full enterprise rebuild can take 12–16 months The PDFs problem: the accessibility gap teams forget after redesigning the whole site Employee thresholds explained (20–49 vs. 50+), including part-time and seasonal, and why contractors don't count Why Ontario led in 2005 and how BC, Nova Scotia, and Manitoba are now catching up How accessibility failures can escalate into Human Rights Code complaints The "not practical" loophole that doesn't exist once you account for available tools and consultants Why the real case for accessibility is ethical, not just legal—the people you cut out when information is missing 📖 Chapters: 0:06 — Why web gets overlooked in accessibility 0:44 — Why organizations fail: not caring vs. not understanding 1:03 — A web-first breakdown of AODA 1:48 — What AODA covers online, and the 50-employee threshold 03:19 — WCAG AA vs. AAA, and who meets the higher bar 03:57 — Ontario, the federal split, and other provinces catching up 06:13 — How monitoring and enforcement actually work 07:23 — Budget cuts, spot audits, and the reality of fines 09:28 — Why 30–60 days is fine for remediation, not redesign 11:18 — What makes compliance officers flexible (or prickly) 13:15 — Employee thresholds and the compliance report obligation 14:40 — Reporting non-compliance and getting auto-audited 17:16 — It's never too late to get started 17:50 — WCAG is evolving: letter of the law vs. spirit of the law 20:30 — Being proactive as a design mindset 21:54 — First steps: count your employees, then audit 23:38 — Start with an audit—compliance is only part of it 25:20 — When accessibility becomes a Human Rights Code issue 28:29 — One hard truth and one piece of encouragement 29:49 — The "not practical" loophole that isn't 30:08 — Where to reach David, and how Tennis can help 🔔 Subscribe for weekly episodes on design, web strategy, and building better digital businesses. #accessibility #AODA #WCAG #webaccessibility #a11y #webdesign #compliance #ontariobusiness #b2bdesign #webdevelopment #inclusivedesign #digitalstrategy #websitedesign #uxdesign #McMillan Links You can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

    50 Employees? Your Website Is Probably Breaking the Law

  3. Jul 2

    Figma Config 2025 Review: Was It Worth the Trip?

    💡 Key Topics: What Config is really like in person, and why Toronto has no local equivalent (RGD, Tech Week, Web Summit gaps) AI fatigue at the conference, and audiences literally clapping when a talk wasn't about AI Why Figma let agents take a backseat in the keynote, unlike last year's AI-heavy product slate John on the new production and motion features, and where designers will push them Anna O on UX for robots and seniors, plus the idea that taste comes from the people you're responsible for Ella Rochelle Lawton on street art as a design system, and real data on murals improving communities The Waymo talk: designing for a driverless car and using the note E for calmness (psychoacoustics) Jezebel DC's "low-tech" talk: why 2000s design was better before attention became the product, with Lego and Animal Crossing as case studies Chelsea Larson (Anthropic) on language as design, prompts as UX, and AI as cars rather than the Industrial Revolution A Stripe designer (Matthew) on density in design and the ink-to-meaning ratio, plus "prove the question is a bad idea before dismissing it" The post-conference verdict versus the pre-trip guesses 📖 Chapters: 0:06 — Back from Config: first impressions 0:51 — Conference scale, and why Toronto has nothing like it 2:18 — Was it AI overkill? First day vs. second day 3:07 — Why Config is valuable: industry direction and art-based talks 3:44 — AI burnout and the crowd clapping for non-AI talks 4:14 — Why Figma let agents take a backseat this year 5:00 — John on the product release: production and motion 5:47 — Favorite talks begin 6:47 — Anna O: UX, robots, and design for seniors 7:43 — "Taste comes from the people you're responsible for" 9:01 — Ella Rochelle Lawton: street art as a living design system 10:14 — The Waymo talk and psychoacoustics (the note E) 12:10 — Jezebel DC: low-tech lessons from the 2000s 13:11 — Lego, Animal Crossing, and designing without dependency 14:53 — Chelsea Larson (Anthropic): language as design 16:25 — AI as cars, not the Industrial Revolution 18:50 — The Stripe density talk and the ink-to-meaning ratio 21:45 — "Prove the question is a bad idea before dismissing it" 23:33 — The secret second talk: too much talking about craft 24:40 — Final ratings: 9, 9, and 9.5   🔔 Subscribe for weekly episodes on design, web strategy, and building better digital businesses.   #figma #figmaconfig #config2025 #figmaai #designconference #uxdesign #uidesign #designtools #waymo #anthropic #designsystems #b2bdesign #designindustry #datavisualization Links You can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

    Figma Config 2025 Review: Was It Worth the Trip?

  4. Jun 23

    We Rated Figma Config 2026 Before Going

    💡 Key Topics: Figma's July IPO and the pivot to positioning itself as an AI company, right down to the software description The claim that ~80% of Config talks are now AI, and whether that's a good or exhausting thing What going public adds to the program: a new investor and analyst session Why 3Blue1Brown, a math channel, is speaking at a design conference Last year's product slate (Figma Make, Figma Buzz) and where those tools actually landed Why Figma's AI feels painfully slow, and why some people are leaving for faster platforms The talks that actually stuck: sentient car-factory robots, Nicole McLaughlin's upcycled fashion, the mouth-roof accessibility device The Weavy acquisition and what node-based generative tooling adds to Figma Anthropic on the Config lineup, and the design-tool overlap (they run on Webflow too) The real question: with the IPO and the AI rebrand, is Config still worth the trip? 📖 Chapters: 0:06 — Heading to Config (and forgetting to pack) 0:31 — What Config is, and why the IPO changes it 1:47 — The big theme: AI, AI, AI 2:00 — Is Figma an AI company now? 2:56 — The new investor and analyst session 3:34 — Last year's drops: Make, Buzz, and the rest 4:00 — Why Figma's AI feels painfully slow 4:46 — AI fatigue vs. hoping for real use cases 5:42 — The talks they still remember: robots and upcycled fashion 6:12 — Hardware, accessibility, and Config as a tech conference 6:53 — Content and community-building talks 8:03 — Why Config matters for a B2B design shop 8:45 — The Weavy acquisition 9:28 — Anthropic at Config (and why they're on Webflow) 10:43 — Rating the conference before they go 11:46 — The verdict: a six and a seven 🔔 Subscribe for weekly episodes on design, web strategy, and building better digital businesses. #figma #figmaconfig #config2025 #figmaai #designconference #uxdesign #uidesign #designtools #figmamake #aidesign #b2bdesign #designindustry Links You can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

    We Rated Figma Config 2026 Before Going

  5. Jun 19

    Italy Almost Had Its Own Silicon Valley. Then It Got Buried.

    💡 Key Topics: Why Italy was primed for this: arriving late to the Industrial Revolution and deciding to win on design instead Camillo's 1908 factory and the "Olivetti style" that predated Apple's design manifesto by 40 years Adriano embedding painters, architects, and writers as full-time co-builders, with design reporting to the top Ivrea as the original Google campus: housing, clinics, libraries, Pasolini lecturing workers at lunch, a five-day week and maternity leave decades early The Programma 101, the first desktop personal computer, and NASA buying it to help plan Apollo 11 The documented Steve Jobs connection: the 1981 "Italian Idea" conference, Bellini, Sottsass, and his pilgrimage to Ivrea The mysterious death on a train, and what happened to the company once the visionary was gone The real lesson: design-led is an operating model, not an aesthetic, and the culture dies if you never institutionalize it 📖 Chapters: 0:07 — The comment that started the rabbit hole 1:25 — How Olivetti made Italy an innovator 2:24 — Camillo and Italy's first typewriter factory 3:00 — Why Camillo looked to America 4:24 — 350,000 lire and a country playing catch-up 5:48 — The M1, and sending Adriano to the US in 1925 7:24 — Adriano takes over and hires artists as co-builders 8:39 — The backdrop: fascism, Futurism, and Rationalism 10:36 — The 1958 "Olivetti style" manifesto 11:28 — MoMA, and designing a whole society 12:56 — Ivrea as the original Google campus 13:43 — Where the idea came from: a double-minority origin 16:19 — A five-day week and maternity leave, decades early 17:30 — Exile and the Community Movement 19:30 — The Programma 101 and NASA's Apollo 11 order 20:48 — The Steve Jobs connection and the "Italian Idea" conference 24:12 — Jobs in exile: Italy, Apple Stores, and the 1997 return 27:11 — Why Apple doesn't look like Olivetti (enter Braun) 29:31 — Death on a train, and the conspiracy theories 32:17 — The real lesson and Italy's buried Silicon Valley   🔔 Subscribe for weekly episodes on design, web strategy, and building better digital businesses. Links You can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

    Italy Almost Had Its Own Silicon Valley. Then It Got Buried.

  6. Jun 12

    The 5 Website Principles Most Companies Get Wrong

    In this episode: Clarity beats cleverness: define the goal and the KPI before the design Structure is the real UX: information architecture as the invisible foundation Speed is a design decision: real speed, perceived speed, and the three-second rule Building for the person who knows nothing about you, starting with ICP work Why AI-generated copy keeps missing the mark Every page needs one job, including the homepage as a traffic mediator Why the first step is always an audit against your ICP Chapters: 0:08 — Series recap and back to basics 1:15 — Principle 1: Clarity beats cleverness 3:50 — Principle 2: Structure is the real UX 6:00 — Principle 3: Speed is a design decision 8:40 — Principle 4: Build for the person who knows nothing 13:46 — Principle 5: Every page needs one job 17:17 — Recap and the first move: do an audit New episodes weekly. Subscribe on Spotify, Apple Podcasts, or wherever you listen. Links You can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

    The 5 Website Principles Most Companies Get Wrong

  7. Jun 5

    Don't Build a Design System Until You See These 3 Signals

    The worst design system project is one that starts too early. Wrong timing, wrong scope, wrong people and it dies in a folder somewhere, untouched. In this episode, Symon and Marcello break down the three signals that tell you you're actually ready for a design system, the two signs you're definitely not, and how to scope a version one that people will actually use. They also cover the build or buy decision, and why adoption matters more than architecture. This is Part 3 of a 3-part series on design systems. 💡 Key Topics: The 3 readiness signals: when a design system actually makes sense 2 signs you're starting too early (and will waste the investment) Build, buy, or borrow: product systems vs. web experience systems Who needs to be in the room beyond design and engineering How to scope v1 so it ships in weeks, not months The 90-day check: how to know if it's working Why the first step is always an audit 📖 Chapters: 0:06 — Series recap and what we're covering today 0:56 — The worst design system project starts too early 1:30 — Signal 1: Multiple teams making decisions independently 2:22 — Signal 2: You're scaling, rebranding, or rebuilding 3:55 — Signal 3: Recreating instead of creating 4:30 — Not ready: your brand isn't stable yet 5:33 — Not ready: no one to own it 6:09 — Build, buy, or borrow 7:49 — Web experience systems: Relume and Osmo Supply 8:27 — Who should manage the design system 9:39 — Scoping version one: start with what you rebuild every time 10:48 — The most common scoping mistake 12:05 — The 90-day check: is anyone actually using it? 12:57 — Start with an audit 13:33 — It doesn't have to be perfect. It has to exist. Links You can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

    Don't Build a Design System Until You See These 3 Signals

  8. May 22

    The Truth About Agency Growth, Pricing, and Why Agencies Fail | ft. Eli Rubel

    💡 Key Topics: Why most agencies get stuck and can't scale past the founder How pricing affects client lifetime, team stability, and the work itself The story behind going from $2,500/month to $45,000/month and back down Why revenue is a vanity metric and what to measure instead Employee churn as the red flag most clients ignore What niching down actually looks like in practice Why mutual respect is the real foundation of a great agency-client relationship   📖 Chapters: 0:00 — How most agencies fail (it's not the work) 0:54 — Eli's background: SaaS, e-commerce, and the leap to agencies 3:52 — Starting MatterMade and the rollercoaster of scaling 5:04 — How an agency operator ended up running an accounting firm 8:26 — The three stuck moments every agency founder faces 12:25 — Why intent matters: choosing to operate as a business 13:38 — Pricing is everything: how it shapes the entire business 17:08 — Client lifetime value: from 7 months to 2.5 years 19:05 — Why agency profitability matters to clients 20:40 — How to vet agency health before signing 22:40 — Revenue vs. profit: what real scale looks like 25:10 — Niching down: why it's scary and why it works 30:58 — What a real agency-client partnership looks like 34:16 — One hard truth and one piece of encouragement   🔔 Subscribe for weekly episodes on design, web strategy, and building better digital businesses. #agencygrowth #agencyprofitability #B2Bagency #clientretention #agencybusiness #pricingstrategy #digitalagency Links You can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

    The Truth About Agency Growth, Pricing, and Why Agencies Fail | ft. Eli Rubel
See All (53)

About

A Digital Strategy Podcast explores how design, technology, and business intersect to shape the way organizations grow and adapt. Through thoughtful discussions and interviews with leaders in tech, design, brand, and marketing, the show shares practical strategies, frameworks, and stories for navigating today’s digital landscape. Hosted by the team at Tennis, the podcast blends sharp takes on the industry with candid conversations about the systems, tools, and decisions that drive lasting impact.

Information

  • Creator
    Tennis
  • Years Active
    2020 - 2026
  • Episodes
    53
  • Rating
    Explicit
  • Copyright
    © 2022 A Digital Strategy Podcast
  • Show Website
    A Digital Strategy Podcast