Design Discord

In this episode of Design Discord, Fernando Mastrangelo sits down with Holly Howard — founder of Ask Holly How and the new AI-powered platform Pyramid.work — for one of the most inspiring and practical conversations we’ve ever had.Holly’s journey is unreal: from training at the Joffrey Ballet, to becoming a music therapist who worked with Oliver Sacks’ methods, to managing legendary Williamsburg restaurants (Marlowe & Sons and Egg), to building a 14-year consulting practice helping designers and creative entrepreneurs build sustainable, values-driven businesses.We go deep on:• Why culture must come before strategy• The psychology of pricing and perceived value• The uncomfortable truth about social media & Instagram ads• How to stop copying other people’s paths • The origin story of Pyramid.work — the AI “strategic engine” that helps entrepreneurs define their purpose, values, and vision, then generates aligned strategy, operations, PR plans, and more!Whether you’re a designer, maker, creative entrepreneur, or just someone trying to build a business that actually feels like you, this episode is packed with hard-won wisdom. Learn more about Holly & Pyramid.work: pyramid.work | askhollyhow.comTimestamps:00:00 — Intro & why Holly is the guru for creative entrepreneurs01:13 — Holly’s origin story: Joffrey Ballet → music therapy → Oliver Sacks04:11 — The magic (and lessons) of Marlowe & Sons in post-9/11 Williamsburg06:29 — Columbia, dropping out of pre-med, and Egg as “business school”14:17 — Forensic accounting, P&Ls, and learning to read the story in the numbers16:38 — Culture before strategy — why values must come from your lived experience21:16 — The most important question most designers never ask24:52 — Pricing psychology, perceived value & the storytelling gap34:18 — Should every designer sell direct-to-client? (Some shouldn’t)36:15 — The brutal truth about social media, ads, and what actually moves the needle45:20 — Introducing Pyramid.work — the AI strategic engine for entrepreneurship53:26 — The wild story of building Pyramid (family investment, Hypatia séance & more)01:01:21 — Putting her own methodology into practice publiclyIf this episode helped you, drop a comment with your biggest takeaway and tag a designer or creative friend who needs to hear it. Subscribe for more conversations at the intersection of design, business, and creativity.#DesignDiscord #HollyHoward #PyramidWork #CreativeEntrepreneurship #DesignBusiness #PricingStrategy #AIForBusiness #ValuesBasedBusiness

In this refreshingly honest episode of Design Discord, Fernando Mastrangelo sits down with David Michon, the sharp, eloquent voice behind For Scale, the buzziest Substack in the design world right now.David shares how he went from writing for Monocle and Icon to creating his own independent platform for real design criticism. Together they unpack why so many design magazines feel identical, why celebrity homes dominate the covers, and how the industry has become strangely polite and risk-averse.They explore:Why “decor” might actually be a more honest word than “design”The liberating joy of imperfect, lived-in homes over sterile perfectionHow growing up in Winnipeg shaped David’s refreshing perspective on tasteThe myth of “timeless” design and why dated interiors can be incredibleWhat’s really wrong with events like Basic Space / Design SpaceThe missing critique in interiors and why optimistic criticism mattersDavid’s writing is smart, observational, and deeply human. He believes great interiors are about people, not just perfect objects — and that your home should never feel “finished.” This conversation will make you look at your own space differently and feel a whole lot better about the dents on your dining table.If you’re tired of aspirational interiors that feel fake and unattainable, this episode is for you. A must-listen for designers, design lovers, interior enthusiasts, and anyone who wants sharper, more honest conversations about the spaces we live in.Follow For Scale on Substack for David’s weekly writings that are quickly becoming essential reading in the industry.Timestamps:00:00 – Introducing David Michon & For Scale09:28 – Winnipeg roots and forming real taste13:00 – Reading rooms as people, not just objects15:00 – Why your home should never feel finished19:20 – Wealth, aspiration, and lived-in reality25:25 – The origin story of For Scale37:25 – Why David chooses “decor” over “design”47:30 – Honest critique of Basic Space52:00 – The future of For Scale: print, events & real-life energy

Join Fernando Mastrangelo on Design Discord for an in-depth conversation with Ashlee Harrison, powerhouse in collectible design. From helping establish Carpenters Workshop Gallery in the US to launching her own private salon Thirty8East in a historic Upper East Side brownstone, Ashlee brings unparalleled insight into the world of functional sculpture, curation, and cultural storytelling.Topics include the maturing collectible design market, working with legendary designers, the power of intimacy over scale, fair experiences, and practical advice for collectors and creatives.Timestamps:00:00 – Intro01:01 – State of Collectible Design Today02:43 – Advisors vs. Interior Designers03:36 – Joining Carpenters Workshop Young05:25 – Early Responsibilities & Building the Business06:35 – Market Expansions to LA, SF & Aspen09:21 – Defining Collectible vs. Fine Furniture11:35 – Collaborating with Artists like Campana Brothers & Studio Drift18:33 – Transition to Thirty8East Salon20:20 – The Salon Experience: By Appointment, Storytelling & Coffee29:48 – Value of Design Fairs & Relationships34:29 – Market Cycles, COVID Impact & Slow Growth39:56 – Future of Her Career & Excitement Ahead48:10 – Advice for Young DesignersPerfect for anyone interested in design, art, collecting, or building a meaningful creative career.Follow Design Discord on Spotify for more. Support the show and share with a fellow design lover!#CollectibleDesign #DesignPodcast #Thirty8East #AshleeHarrison

In this episode of Design Discord, hosts Fernando Mastrangelo and Alyssa Gerasimoff celebrate the end of the year with the first annual Design Discord Awards. They discuss their selections for various categories, including best fair, booth, interior designers, and galleries, while reflecting on the challenges of making these choices. They also highlight designers to watch in 2026 and discuss their plans for the upcoming season two of the podcast, reflecting on their journey and the insights gained throughout the year.05:26 Best Fair 10:30 Best Booth14:02 Best Interior Designer/Architect18:31 Best Gallery25:55 Best Showroom32:19 Best Breakout Star34:51 Best New Collection38:56 Most Innovative Use of Materials46:34 Best Chair49:45 Best Lighting56:45 Best Side Table59:30 Best Fine Furniture01:03:10 Best Ceramic Furniture01:12:46 Best Collectible Design01:18:35 Best Photography01:24:40 Favorite Design Discord Episode01:28:10 Designers to Watch in 2026