Greg Robleto

Greg Robleto

Design and product leader working at the intersection of finance, brand, and digital platforms—based in Rockville, Maryland and exploring how design, systems, and AI shape the future of financial products.

Design Director at Motley Fool Asset Management.

Signals

Notes on design, systems, and the work of making complex things coherent.

Design

Designing Trust in Financial Products

Mar 2026

Designing trust in financial products requires addressing survivorship bias and enhancing user confidence through clear, structured information. Effective design prioritizes understanding and aligns all elements to foster trust, preventing potential investors from disengaging.

Design

Not Everything Needs To Be Built

Mar 2026

Craft-driven teams often struggle with throughput due to bespoke deliverables. Instead of lowering quality to speed up, focus on using existing tools to solve operational problems. The goal is to prioritize meaningful work that truly adds value. Not everything needs to be built.

Design

Web Overhauls Under Real Constraints

Mar 2026

Facing tight timelines and complex systems, the author emphasizes mastering inherited platforms instead of tearing them down. By understanding HubSpot deeply, targeted improvements were made across multiple business lines, showcasing the value of working within constraints.

Design

Experiments in Public

Mar 2026

Experiments in Public highlights the importance of side projects in personal development, showcasing how creative experiments lead to skill growth, connection, and renewed confidence, ultimately enriching professional work and fostering innovation.

Writing

AI enhances design workflows by producing high-quality artifacts quickly, but it does not replace the deeper decision-making and intent behind design. The real work of design—narrative, trade-offs, and taste—becomes clearer as automation removes the labor that previously obscured it.

AIMar 2026
AI Hasn’t Replace Design. It Revealed What Design Wasn't.

This weekend, I enhanced the Rockville High School Booster Club Mulch Sale website by streamlining the checkout process and improving clarity. The changes reduce manual follow-ups and make ordering easier for families, ultimately benefiting the hardworking volunteers.

DesignMar 2026
Making the Most out of Mulch. Stay With Me.

After 20 years at The Motley Fool, I reflect on my journey from design to leadership, the teams I’ve built, and the joy of impactful work in a fast-paced marketing environment. Grateful for the experiences and people who shaped my path.

Personal DevelopmentJan 2026
20 Years of Fooldom

Using AI, I revived cheesy financial pickup lines from a 2010 spreadsheet, creating a fun generator with Chad Cattle, a confident cartoon bull. The project launched just in time for Valentine's Day, blending cringe-worthy humor with finance. Visit

AIFeb 2025
Margin Call Me: How I Misused AI to Deliver Cheesy Financial Pickup Lines

Create a dynamic word carousel card with pure CSS, showcasing multiple roles or titles in an elegant, animated display. Perfect for portfolios, landing pages, and storytelling, this reusable component highlights the power of simple, clean design.

CSSJan 2025
Building a Dynamic Word Carousel Card with Pure CSS