Connor Gross has built and operated across multiple income streams: an early e-commerce exit, self-storage and real estate deals, an apparel e-commerce business, content sites, and now Constant Hire, a recruiting agency focused on helping e-commerce and consumer brands hire top talent.
In this episode, we talk through Connor’s path from selling his first business in his early 20s to buying a self-storage property off a Facebook group, tripling its revenue, and eventually narrowing his focus around recruiting for fast-growing consumer brands.
We also get into the changing labor market inside e-commerce: why creative strategists are becoming more valuable, how TikTok Shop is creating entirely new roles, what AI may or may not replace, and why employer branding matters more than most founders realize.
The second half of the conversation turns more personal. We talk about ambition, focus, family, cash flow, playing it safe, and what it really means to go all in on one thing. Connor is in the middle of deciding what kind of life and business he wants to build, and I share the mindset that helped me stay all in on Filterbuy for more than a decade.
Topics include:
Connor’s first exit with Cardly
Buying and improving a self-storage property
Why he started Constant Hire
Recruiting for e-commerce and consumer brands
The rise of creative strategists, TikTok Shop managers, and creator managers
How AI is changing marketing, finance, operations, and hiring
Why I’m pausing certain non-operational hiring at Filterbuy
The difference between stacking cash flow and building something big
What it means to emotionally commit to a business
Why top talent has to be recruited, not just hired
This is a conversation about business models, ambition, self-awareness, and choosing the path you actually want.
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