Brennan Haelig: How Can You Build a Service Business from Freelancer to Agency Owner?

Meet Brennan Haelig, founder and CEO of Jumpstart ROI. Once homeless and sleeping in his 10 × 10-foot recording studio while juggling a day job, he taught himself digital marketing, embraced paid-ads funnels and climbed to running a multiple seven-figure agency with an 18-person team.

If you’re an aspiring entrepreneur — whether you’re a young professional, a mid-career switcher or someone from an under-represented background — this story resonates. It shows how to move from doing the work yourself to building a service business that works for you. In this article you’ll discover key lessons about deal flow, team building, mindset and metrics — all through Brennan’s journey.

From suitcase at your day job to agency founder

At one low point, Brennan had 50 cents in his bank account, credit-card debt, and a suitcase he carried to his day job so coworkers wouldn’t know he was homeless. He then pivoted: taught himself Facebook Ads, Google Ads, approached clients, built case studies, and put everything on the line. He recalls:

“I actually got let go from my day job … which forced me to go all in on the business.

A lot of times there’s not that self-confidence … I still had to just be confident anyways.”

That leap of faith forced the shift from part-time side hustle to full-time agency and unlocked break-through months in revenue.

Why deal flow solves almost every service-business problem

One of Brennan’s biggest realizations: consistent lead generation is the lifeblood of a service business.

When you’re at ~$20K/month you worry “What happens if I lose a client?” When you have steady inbound you can experiment, raise prices, hire, and scale.

Brennan explains: “We get about 100 leads a month just from that channel… All of a sudden getting 20 leads a month, 30 leads a month, 40 leads a month…”. They used a freelancer-marketplace channel (like Upwork) to scale lead volume, which unlocked the jump from ~$20K/month to $100K/month.

Takeaway for you: Ask yourself — how can I build predictable deal flow? Without it, you’re always hanging by a thread.

Metrics & mindset: The two wings of growing a business

1. Metrics that matter

Service businesses often fall into the trap of vanity metrics: clicks, impressions, hours billed. Brennan emphasises: “Ultimately, we care about deals closed, new clients, and return on investment.” Tracking the cost to acquire a client, the lifetime value of that client, and the margin after software/labour/fulfilment becomes critical. Using CRMs, Zapier, dashboards — all help."

If you don’t know what a new client is worth, you’ll either under-spend on marketing or over-spend and kill your profit.

2. Mindset shifts

The journey from freelancer → owner-operator → owner of a business that runs without you is messy. Brennan writes candidly about doubts, impostor feelings, decisions like when to hire or let go. He describes his work with a “business therapist” consultant who reminds him:

“You have to drop the ball and let the team pick it up… They’ll never learn how to run with the ball.”

This shift—letting go, trusting others, delegating—makes the difference between you doing everything and your business working for you.

Hiring and fulfillment: Why you need both sides of the growth coin

Any service agency can get leads, but retaining those clients and scaling fulfillment is the second half of the puzzle. As Brennan’s business grew:

• He moved from doing all client communication to building a team that handles onboarding and fulfilment.

• He acknowledges he still does sales today—but the next phase is hiring a sales rep, training them, and stepping out of lifecycle involvement completely.The lesson: growth requires balancing lead generation with delivery excellence. If you hire too early without systems, you burn margin; too late and you bottleneck.

  
  

For who? Which businesses is this relevant for?

If you’re a service business that has found product-market fit (you already have revenue, maybe in the $50K-$100K/month range) and you’re looking to scale to $300K-$500K/month, Brennan’s playbook applies. Whether you’re B2B-tech, professional services, or local service business — the principles hold. If you’re still at zero revenue or purely referral-based and you haven’t yet built consistent deal flow, focus first on predictable leads and metrics. Then, once that’s stable, you can scale.

FAQ-Style Subheadings

• Q: How do I know when I should go “all in” on my business?

When your business income is approaching or exceeding your day-job income and you can support yourself without the job, that may be your cue. Brennan’s turning point: losing his day job pushed him into full time — scary but necessary.

• Q: How many leads do I need to scale an agency?

It depends entirely on your offer, conversion rate, client value and costs. Brennan’s agency went from ~20 leads/month to ~100 leads/month before leap-frogging revenue. The key is creating a system for predictable, repeatable lead volume.

• Q: What should I track to know if I’m profitable?

Track: client acquisition cost + labour cost + software cost + fulfilment cost → client lifetime value. If your first-month revenue from the client is more than double what you spent to acquire them, you’re in a strong position (echoing frameworks like those from Alex Hormozi).

Conclusion & Call to Action

Here’s what to take away:

• You can start from scratch. You can go from paying your day job to running an agency.

• Lead generation is foundational. Fix that and many other problems fade.

• Metrics and mindset carry you through the transitions: freelancer ➝ owner-operator ➝ owner of a business that runs without you.

• Systems and delegation are messy but essential.

So: choose one action this week. Maybe map out your lead-generation channel. Or build a dashboard that shows cost per client. Or pick one task to delegate and let your team handle.

If you’d like to go deeper, share this article with someone in your network, and if you’re ready to hire someone to help implement these strategies, consider reaching out to Brennan’s team at Jumpstart ROI for a chat.

Your challenge: Commit to one metric you’ll track every week and one thing you’ll delegate next week.

Good luck — you’re building more than a business. You’re building your future.