Welcome back fellow investopreneurs!

Im excited to share we are spinning up the Bootstrapping to Billions podcast.

The first episode is going to be recorded this coming week. If you would like to be a guest on the pod, reach out!

The podcast focuses on actionable insights, practical strategies, and the authentic journey toward building better businesses that maximize equity and create long-term freedom.

We aim to inspire entrepreneurs to build and grow businesses that thrive, focusing on freedom, control, and maximizing value. Whether you’ve bootstrapped or raised capital, this show is about navigating the stages from first dollar to final exit while retaining ownership, building equity, and making strategic decisions that align with your long-term vision.

About 10 years ago we spun up a bookkeeping firm.

It came directly out of demand we saw in the market from an economic development organization we built.

Over the past decade we have tried most everything we could identify to acquire customers and build the business.

Here is a 10 year case study of three of those strategies…

🧪 The 3 Ways We Acquired Customers:

1. Traditional Sales Team

We hired two reps: base + 25% commission after quota.

What it took:

• CRM + outbound email + paid ads

• $7K/month in salaries

• ~$3K per customer in landed CAC

• With commissions: $5,100–$5,700 per customer

• 6–12 month timeline to get to 18 clients

• 2.1x annualized ROI (break-even in ~9 months)

Upside: Human touch, consultative selling
Downside: Slow, expensive, hard to scale

2. M&A (Buying a Book of Business)

We acquired a QuickBooks-based firm with 31 clients at a 1.1x multiple ($121K purchase price) with a partial money down + earn out structure.

What we got:

• 18 retained clients after 60% post-acquisition churn

• Cost per customer: $6,722

• ~$194K ARR post-deal

• Break-even in ~8 months (at 50% margins)

Upside: Instant cash flow, proven customers
Downside: Retention risk, upfront capital required, slower ROI than AI

3. AI-Driven Agentic Funnel

We built a full AI-powered outbound system:

• Apollo + n8n for sourcing + personalization

• Instantly.ai for outreach

• VSL page with an AI voice agent for Q&A

• CTA to purchase at bottom of page

Here’s what it did:

• 5,000 leads → 18 customers at ~$1,000 CAC

• No commission. No salaries. No team.

• $5,500/month in total spend

• 35x annualized ROI

• Break-even in just 1.5 months

Upside: Fastest payback, cheapest CAC, runs on autopilot
Downside: Lead quality needs monitoring, tech breaks if not maintained

🎯 What This Means

When I ran these models side by side, here’s what stood out:

🧠 Final Take

If you're still scaling with sales reps or buying customer lists, it might be time to ask:

We still believe in human-powered brands—but the acquisition?
That’s may be becoming a job for systems and agents.

📺 I broke this all down in a video here.

And if you want to install this exact AI funnel in your business—just reply “Profit Me” and I’ll send you the playbook.

Build smart. Exit with ownership.