Today’s guest is someone I’ve known for more than twenty years — an industry friend, a former competitor, and one of the rare creatives who evolved into a world-class operator. Marty Ringlein built nclud, the boundary-pushing digital agency acquired by Twitter; nvite, the elegant events platform acquired by Eventbrite; and now Agree.com, a modern challenger taking aim at a category pioneer and cultural verb: DocuSign.

What makes Marty’s journey so compelling is how he fuses creativity with business strategy. He understands how humans respond to clarity, trust, and friction — and he turns that insight into products people adopt and platforms want to acquire. Agree.com isn’t just another tool; it’s a rethinking of how commitments happen in an AI-native world where simplicity and differentiation are harder than ever to pull off.

Today we’re exploring how his personal brand has evolved across three very different companies, what incumbents consistently underestimate about challengers, how he balances being a professor, a CEO, a VC, and a dad — and what it would take for the phrase we’ve all said a million times (“send me a DocuSign”) to someday become simply: send me an agree.

Questions include...

You’ve rebranded yourself multiple times — from designer to creative director to founder to CEO.
What part of your personal brand has remained constant through every reinvention?

nclud had a rebellious, almost punk ethos. nvite was polished and UX-driven. Agree.com feels radically simple and trust-first.
How intentionally do you design the brand personality of each venture?

Every category challenger needs a story that reframes the market.
What’s the positioning narrative you crafted to make Agree.com feel like the future, not just a cheaper DocuSign?

In branding, timing is everything.
What’s the moment you knew the world was ready for a different kind of agreement platform?

Brand loyalty is earned through emotional clarity.
How do you inject emotion — trust, speed, confidence — into a product that’s inherently transactional?

One of your superpowers is reducing complex categories into simple, human forms.
How do you approach language when naming a company, a brand, or even a product feature?

You’ve built brands through massive platform shifts — Web 1.0 → social → mobile → AI-native.
What’s the hardest part of keeping a brand relevant when the ground keeps moving?

Agree.com is competing in a category where the leader has become the default verb.
What’s the playbook for turning Agree into a new verb?

Every brand has an enemy.
When you built Agree, who — or what — was the “enemy” you defined internally?

You’ve always leaned toward visual clarity and minimalism.
When does simplicity become a brand strategy versus just a design preference?

In your career, what was the moment a brand decision completely changed the trajectory of a company?

Positioning requires saying “no” more than saying “yes.”
What’s something you refused to let Agree.com become?

If you boiled your entire branding philosophy down to one sentence, what would it be?

Great brands have rituals.
What are the rituals or micro-habits that make Agree.com feel different from legacy players?

You’ve seen how acquisitions impact brand identity from the inside.
What’s the biggest branding mistake large companies make when absorbing a startup?

As a professor, you teach the mechanics of design and creativity. As a CEO, you live the mechanics of positioning.
How do those worlds reinforce — or sometimes contradict — each other?

What’s the hardest brand pivot you’ve ever had to make — either personally or professionally?

If nclud represented experimentation and nvite represented connection, what human truth does Agree.com represent?

Founders often underestimate the emotional weight of a rebrand.
What’s a branding decision you agonized over more than you expected?

If you had to write a new chapter in the “Marty” brand — post-Agree — what theme would it center on?