When your broker suggests buying 3 businesses at once

Deacon here with an update that perfectly illustrates why Travis and I make a good team – and why sometimes the most ambitious ideas need a reality check.

As these deals started flowing in, Travis and I realized we'd been thinking about funding in the abstract. "We'll figure out SBA or investors or bank debt when we need it."

Classic mistake: waiting until you need money to figure out how to get it.

So we started the funding process early, before any deals were locked down. Smart move, because the learning curve was steeper than expected.

Our first SBA broker had a fantastic initial call. We learned a lot, felt optimistic about the process. Then he sent over a stack of forms and... vanished. No follow-up, no guidance, just radio silence.

Red flag. If someone can't manage a simple client relationship during the courtship phase, what happens when things get complicated?

Our second broker came through a mastermind referral. Immediate difference in professionalism and expertise. They'd done deals with our contact before, which gave us confidence.

During one of our early meetings, we laid out our pipeline: "Here are the three deals we're evaluating. Here's roughly what each would cost."

I expected them to say, "Okay, let's pick one and structure funding around it."

Instead, they asked: "Do you want to do one of these separately, or do you want to try to buy all three?"

Travis, without missing a beat: "Let's buy all three."

The broker explained something we hadn't considered: you can roll multiple acquisitions into a single SBA funding package. One loan, three businesses, boom – instant portfolio.

Travis's reasoning? Our mentor always tells us: "You're not dreaming big enough. Whatever you're thinking about, add a zero."

Meanwhile, I'm having a minor heart attack.

As the operations guy who'd have to integrate three completely different businesses simultaneously, my brain immediately went to all the ways this could go sideways. Three different sellers with different motivations. Three separate due diligence processes. Three sets of legal docs that all need to align.

But here's the thing about working with Travis – he's not reckless. When he suggests something ambitious, there's usually strategic thinking behind it. So I figured: I teamed up with him for a reason. Let's ride with this and figure it out as we go.

As we learned more about the SBA process, we discovered a critical issue with the three-deal approach: all transactions would need to close simultaneously.

Think about that complexity:

• If any one deal falls through, the whole package collapses

• Triple the moving parts, triple the risk

• We'd be learning three businesses at once instead of mastering one

We quickly realized we were adding unnecessary risk to an already complex process.

After working through the implications, we made a key decision: even if all three deals materialized, we'd structure them as separate transactions and focus on one at a time.

Master one acquisition process before attempting three simultaneously.

This whole experience perfectly illustrated how Travis and I work together. He pushes for bigger thinking, I stress-test the operational reality, and we find the right balance between ambition and execution.

The best partnerships aren't about always agreeing – they're about challenging each other's assumptions and finding better solutions together.

Travis keeps me from moving too slow, and I keep him from spreading too thin. Together, we make decisions that are both ambitious and executable.

For Fellow Operators:

• Start your funding conversations before you need capital

• Interview multiple brokers (they're not all equal)

• Let ambitious thinking inform strategy, but let operational reality guide tactics

For Potential Partners: Sometimes the most valuable conversations happen when someone challenges your assumptions about what's possible. The difference between dreaming big and dreaming smart? Smart dreamers build systems that can handle the complexity their ambitions create.

This funding education set us up for everything that came next. Speaking of which, next week I'll tell you about the deal that almost worked perfectly on paper – until we discovered it was based in Canada.

Have you ever had to scale back an ambitious idea for operational reasons? Sometimes the constraint creates a better strategy.

Until next time,

Deacon

P.S. Based on some recent deal experience we’re starting to focus more on partnerships and not just buy-out acquisitions. If there’s one thing we’re great at, it’s scaling e-commerce brands. Hit me up if you want to chat.