A Digital Strategy Podcast

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

    23H AGO

    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

    38 min
  2. What a Design System Actually Is (Explained by Someone Who Builds One)

    MAY 15

    What a Design System Actually Is (Explained by Someone Who Builds One)

    Key Topics: • The Lego analogy: the simplest way to explain a design system to anyone • What's actually inside a design system: foundations, components, patterns, and documentation • How designers, developers, and product managers use a design system day to day • Why a brand guide and a design system are not the same thing • Design system governance: who owns what, and what happens without it • Opinionated vs. flexible: how Intuit decides what teams can and can't change • Why adoption is a culture problem, not a technical one • The ROI question: because it always comes back to ROI   Chapters: 0:00 — The Lego analogy for design systems 0:42 — Intro: Part 2 of the design system series 1:35 — Avi's role on Intuit's design platform team 3:08 — How the GenUX team serves internal business units 5:04 — Catching AI inconsistency before it scaled out of control 6:09 — Explaining a design system to someone who's never heard the term 8:42 — Why every new brick has to work for every set 9:52 — What a design system actually touches inside an organization 10:19 — Benefits: consistency, trust, and a shared language 11:47 — Drawbacks: slowing down in a world that moves fast 12:52 — Does a design system help resolve conflict between teams? 14:06 — When teams build outside the system (and why that's useful feedback) 15:55 — Fixed vs. flex: what's opinionated and what's open 17:20 — Advice for smaller companies: know your why 19:04 — The communication breakdown that kills adoption 19:52 — Getting people to actually commit: governance and culture 20:08 — Why it always comes back to ROI 22:42 — One thing to take away if you've never thought about design systems 25:08 — Symon's takeaway: know the why before you build 25:28 — Marcello's takeaway: the Lego analogy 25:55 — Where to find Avi 26:35 — What's next: Part 3 on building a design system   🔔 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

    26 min
  3. Why people don't trust your business

    MAY 8

    Why people don't trust your business

    Key Topics: Why AI is accelerating brand chaos at the mid-market level The difference between a brand guide and a design system What design debt looks like, and why you don't feel it until it breaks Single source of truth: why every team having its own components is killing your brand Why speed without systems is just expensive chaos Chapters: 0:16 — Why design systems are blowing up right now 1:12 — How AI is accelerating brand chaos 3:22 — What brand drift actually looks like in organizations 5:18 — Is this a design problem or a systems problem? 7:20 — The single source of truth problem 9:30 — What design debt actually costs 12:26 — Why you don't feel it until it breaks 13:41 — What to do if you're moving too fast 14:11 — Speed without a system is just expensive chaos 15:52 — Fix it upstream, not downstream 16:51 — The only real starting point 17:20 — One thing to take away 🔔 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

    19 min
  4. Design Is on Trial (And the Evidence Is Damning)

    APR 30

    Design Is on Trial (And the Evidence Is Damning)

    What we cover in this episode: 🔹 [0:00] — The verdict: What actually happened in the Meta/YouTube lawsuit 🔹 [2:16] — Kaye's story and why starting social media at age 6 matters 🔹 [3:55] — Internal Meta documents: "If we want to win big with teens, we must bring in tweens" 🔹 [7:50] — Section 230: The 30-year legal shield that finally cracked 🔹 [9:06] — Engineering addiction through design — and why that's different from designing for engagement 🔹 [11:07] — Infinite scroll, autoplay, and push notifications: tools or weapons? 🔹 [15:14] — Why this is a bellwether trial and what comes next 🔹 [18:02] — The Big Tobacco parallel: history is repeating itself 🔹 [22:27] — How this affects adults too: deleting Instagram, capping Reddit, and reclaiming attention 🔹 [26:36] — What should Meta do now?   This case isn't just about one family. It's a signal that real UX decisions made by real teams carry legal, ethical, and societal weight. If you work in tech, product, or design, this episode is essential listening. 🔔 Subscribe so you don't miss our next episode Links You can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

    29 min
  5. AI Didn't Commoditize Design. Designers Did.

    APR 24

    AI Didn't Commoditize Design. Designers Did.

    In this episode: • How design evolved from a contained discipline in 2006 to absorbing everything by 2020 • Why low-code, no-code, the gig economy, and nearshoring created a race to the bottom on execution • The three disciplines of market leaders — and which one actually resists commoditization • How network effects are reshaping agencies, product teams, and businesses • Why focus is the only real differentiator left   Chapters • 00:00 The Evolution of Design and Technology • 04:17 The Impact of AI on Design • 09:33 Redefining the Value of Design • 15:18 Focus and Niching Down in Design • 21:24 Operational Excellence, Product Leadership, and Customer Intimacy • 25:45 Navigating the Network Effect in Modern Business   Follow Tennis: tennis.digital @design_tennis Links You can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

    28 min
  6. Something Is Wrong With Your Website and Nobody Will Tell You

    APR 16

    Something Is Wrong With Your Website and Nobody Will Tell You

    Key  topics Definition of technical debt in web development How small decisions compound over time Real-world examples of web debt Strategies for auditing and addressing web debt   Chapters 00:00 Technical Debt in Web Development 00:19 Understanding Incremental Web Debt 03:19 The Impact of Technical Debt 08:21 Real-World Examples of Technical Debt 14:49 Addressing Technical Debt 17:42 Final Thoughts and Takeaways 20:09 outro.mp4   Resources Tennis - Web Design & Development Agency - https://tennis.co Symon Oliver on LinkedIn - https://linkedin.com/in/symonoliver Marcello Gortana on LinkedIn - https://linkedin.com/in/marcellogortana Links You can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

    20 min
  7. Your CFO Isn't Saying No to Your Website

    APR 10

    Your CFO Isn't Saying No to Your Website

    Notes Why does a website project that everyone agrees is needed keep dying in the finance meeting? Usually it's not the budget — it's the pitch. Symon and Marcello break down how to reframe a web investment as a business initiative, not a creative one, and walk through exactly how to build a case that finance can actually approve. Topics covered: current cost audit (hosting, content ops, lost leads), opportunity cost of inaction, competitive and technical risk, how to connect a website to revenue (and when you can't), OPEX vs. CAPEX considerations, phase-based budget structuring, and how to build a measurement plan before you ask for money.   Chapter List (YouTube + Podcast) 0:00 — Intro: Why website projects die in the finance meeting 1:41 — The business case is already there — it's a framing problem 2:20 — Why most website business cases fail 4:13 — Looking at risk: compliance, accessibility, and fines 5:13 — Current costs: what your website is actually costing the business 7:00 — Opportunity cost: the website as a go-to-market tool 7:46 — Risk of inaction: technical debt and competitive positioning 9:00 — The investment ask: phasing, fiscal year alignment, flexibility 9:25 — Defining project objectives from day one 10:30 — How to connect a website to revenue (and when you can't) 12:13 — Content bottlenecks as the baseline business case 13:34 — Page speed: the metric that impacts both UX and search 14:34 — Indirect value: brand credibility, talent, partner perception 16:22 — How Tennis grew its own inbound with SEO and AEO 19:10 — When the full budget won't get approved: the phase-based ask 21:00 — What to do first if you need to pitch in the next 60 days 22:28 — Build the measurement plan before you ask for the budget 23:00 — OPEX vs. CAPEX: how finance wants to spend matters 24:49 — Final takeaway: stop pitching a website Links You can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

    26 min
  8. The Mistake That Kills Most Projects (It's Not the Budget)

    APR 2

    The Mistake That Kills Most Projects (It's Not the Budget)

    Most projects don't fail because the team couldn't build. They fail because the team tried to build everything at once. In this episode, Symon and Marcello break down why project scope creep and feature bloat are the real killers of product development timelines—and what to do about it. They walk through how to run a fast complexity audit before committing to any digital project, why a discovery phase and product requirements document (PRD) belong on every project regardless of size, and the difference between a proof of concept and an MVP (they're not the same thing, and confusing them is expensive). Whether you're scoping a website redesign, building your first web application, or evaluating a vendor for a complex B2B product—this one will save you from a very avoidable mistake. In this episode Why ambitious timelines and bloated scope are a reliable path to failure  The complexity audit: how to pressure-test a project before you commit  Proof of concept vs MVP  what each one is actually for  What the Think Phase and a proper PRD do that no kickoff call can  Four rules for phased delivery that actually ships Chapters 0:00 — Intro 0:36 — You can't boil the ocean 3:25 — The complexity trap 5:19 — Feature bloat in the real world 7:57 — Proof of concept vs MVP 10:37 — The discovery phase and the PRD 14:43 — Four rules for phased project delivery 19:31 — Wrap About Tennis Tennis is a B2B Web Design and Product Development Agency based in Toronto. We help mid-market teams turn complex digital problems into staged, ROI-driven builds—where each phase moves something real and earns the right to expand. tennis.digital → Follow us on LinkedIn Links You can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

    20 min
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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
    46
  • Rating
    Explicit
  • Copyright
    © 2022 A Digital Strategy Podcast
  • Show Website
    A Digital Strategy Podcast