Brennan Haelig is a digital marketer turned agency owner, and we spoke about going from sleeping in a 10×10 studio to leading a multi–seven-figure team of 18. “Back in 2018, I was homeless, sleeping in my recording studio,” he recalls, adding, “I remember having 50 cents in my bank account.” The early aim wasn’t millions—it was simply to support himself without “a full time corporate job.”

His turning point came when he was let go from a part-time day job and had to go all-in. Growth followed once he built dependable deal flow—first by mining Upwork for steady, qualified leads—and focused on what matters: deals closed, ROI, and CAC, not clicks. As he puts it, “lead gen and deal flow pretty much solves all of the problems.” Practically, that means one scalable channel (then more), paid ads (Meta/Google/LinkedIn) feeding a CRM, and an integrated dashboard (APIs/Zapier) tracking cost per appointment, pipeline stages, and payback—aiming for month-one revenue to exceed 2× acquisition cost.

We also unpacked the messy shift from freelancer to owner: hiring fulfillment before sales replacement, keeping standards high, and learning to delegate. A mentor taught him “knowing when to drop the ball” so the team picks it up, while Brennan admits entrepreneurship often requires “manufactured self confidence.” The why stayed constant: prove he could stand on his own and build something that lasts.

In short, this conversation gives a concrete system—lead flow first, metrics that matter, and staged delegation—to move from $20k months toward $200k and beyond.

Key takeaways

Build one scalable channel; Upwork drove ~100 leads/month.
Replace vanity metrics with deals closed and ROI dashboards.
Ask first: “How many clients do you want?”
Ensure month-one revenue exceeds 2× customer acquisition cost.
Practice delegation: occasionally “drop the ball” so teams learn.
Lead flow and hiring are twin levers from $20k to $200k.

Brennan Haelig: From homeless to 7-figure agency?