Kings of Swag with Jeremy Parker
Kings of Swag with Jeremy Parker
Podcast Description
Kings of Swag is your front-row ticket to the world of promotional products—from distributors and suppliers to the brands that make headlines. Hosted by Jeremy Parker, co-founder and former CEO of Swag.com, each episode digs into the journeys, motivations, and lessons of the promo industry’s top leaders and innovators. Whether you’re building a career in swag or simply need a fresh dose of entrepreneurial inspiration, tune in and discover what’s possible.
Podcast Insights
Content Themes
The podcast revolves around themes of entrepreneurship, business strategy, and industry innovation, with episodes that highlight personal stories from leaders like Sharon Eyal, who discusses his growth from $1M to over $100M in drinkware sales, and the lessons learned from significant challenges such as legal battles and market crises.
Kings of Swag is your front-row ticket to the world of promotional products—from distributors and suppliers to the brands that make headlines. Hosted by Jeremy Parker, co-founder and former CEO of Swag.com, each episode digs into the journeys, motivations, and lessons of the promo industry’s top leaders and innovators. Whether you’re building a career in swag or simply need a fresh dose of entrepreneurial inspiration, tune in and discover what’s possible.
James Armijo, CEO of Taivo, joins Jeremy Parker to talk about his unlikely path into the promotional products industry — and what he's learned about building, acquiring, and integrating software businesses along the way.
James joined Inktavo as CEO in 2022 without a background in promotional products. Instead, he brought years of experience building software for highly specific customer groups, from small businesses to doctor's offices and childcare centers. That experience became the foundation for his approach to Taivo: learn the industry, listen to customers, and build technology around the problems they actually need solved.
James walks Jeremy through the evolution from Printavo and Inksoft to Inktavo, and ultimately the merger with OrderMyGear that created Taivo. He explains how he thinks about M&A through his “three-legged stool” of customers, employees, and investors — and why a deal needs to make sense for all three.
They also get into one of the hardest parts of scaling a company: people. James shares a leadership mistake that taught him the importance of recognizing when someone may no longer be the right fit for a role, and why making that decision sooner can ultimately be more humane for everyone involved.
Plus, James explains how Taivo approaches technology adoption, why software should improve existing workflows rather than simply digitize them, and why being willing to fail is an essential part of building a company that can keep adapting.
In this episode:
• James's journey from SaaS investing to becoming a CEO
• Entering the promotional products industry as an outsider
• The evolution from Printavo and Inksoft to Inktavo and Tevo
• Integrating different companies, cultures, and teams
• The three-legged stool of customers, employees, and investors
• How James evaluates acquisitions and mergers
• Getting customers to actually adopt new technology
• AI, automation, and reducing friction in business workflows
• A major leadership failure and the lesson it taught him
• Why successful companies have to keep adapting
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