In this episode of The Art of Commerce, we sit down with Chris Adamo, founder of Letterhead, to explore the unconventional path from corporate operator to startup builder.

Chris spent years at 1-800-Flowers, working at the intersection of partnerships, commerce, and media. Instead of staying in the traditional corporate lane, he eventually stepped out to build companies, invest in startups, and help shape the emerging tech ecosystem in Miami.

This conversation dives into the mindset that drives operators who choose to build instead of staying comfortable inside large organizations.

In this episode we cover:

• Chris Adamo’s journey from Queens to 1-800-Flowers
• How partnerships became his career superpower
• Lessons learned managing chaos early in his career
• The importance of curiosity and talking to strangers
• Why mentorship and breaking corporate silos matters
• How Miami became a growing startup ecosystem
• The story behind Letterhead, an AI-powered newsletter platform
• Why community and relationships are still the most valuable currency in business

Chris shares practical lessons on networking, entrepreneurship, and how operators can turn relationships into real opportunities.

For marketers, founders, and operators, this episode is a reminder that careers rarely follow a straight line and sometimes the most valuable skills are the ones learned outside the box.

About The Art of Commerce

The Art of Commerce is a podcast about creativity and conversions hosted by Anish Raul, a data-obsessed creative director, and Ajinkya “Jinx” Joglekar, a growth-obsessed CMO. Each episode explores the ideas, strategies, and people shaping modern marketing and business.

Connect on LinkedIn

Anish Raul:
https://www.linkedin.com/in/anishraul

Ajinkya “Jinx” Joglekar:
https://www.linkedin.com/in/ajinkyaj

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