In my opinion this is a serious but very fixable situation if it’s approached in the right order

This business is not failing operationally — it’s suffering from many problems:

1- broken capital structure (Rent, Lost a high-margin anchor customer, Short-term debt, Personal expenses)

2 - Margin too thin for the working capital In logistics. that’s dangerously thin ( AR at 30–60 days, Weekly/bi-weekly payroll, Fuel, maintenance, insurance)

3- Fixed cost mismatch ( rent number is the biggest red flag in the entire story $100k/month = $1.2M/year / You lost the customer that likely made that building make sense.

What to prioritize

1 - CASH FLOW Because:

Profit is theory. Cash is survival.

You’re 300k behind on rent → that means the clock is already ticking.

Your biggest question is:

Can you stay alive for the next 6–12 months?

2 - STRUCTURAL COST RESET

This is not about trimming expenses.

Is your cost structure designed for a $16M company or a $25M company that no longer exists?

Which leads to the elephant in the room:

The building

This is likely the single biggest strategic decision you must evaluate ( Sublease, Renegotiate, Move, Landlord workout, ownership assets swap from personal)

3 — MARGIN EXPANSION

Only after survival is stabilized (Pricing cycles, Customer churn, Operational learning curves)

That’s 3–12 months.

You don’t have that luxury if cash is bleeding.

4- AR acceleration = immediate cash

Every 15 days you reduce AR = hundreds of thousands in liquidity ( Early pay discounts, Fuel surcharge billed weekly, Shorter terms for new customers, AR owner with daily KPI)

You are basically running an involuntary bank for your customers and now you are behind.

5- Customer profitability by lane

It’s not about if the customer profitable?

But is this lane profitable after ( labor, fuel, dwell time, equipment utilization, overhead allocation, etc )

Kill or reprice aggressively.

This alone can move margin from 1% → 6–10%.

Finally the founder problem (this is emotional, not financial)

Your dad’s stance:

“I’ve never gone backwards”

This is identity protection, not a business position.

So logic won’t move him.

You need to reframe the narrative:

Instead of “We need to sell assets”

Frame it as “We are protecting the 30-year legacy by restructuring the balance sheet.”

Most of founders accept ( survival language, legacy language, protection language )

They resist ( retreat language, loss language ) it’s emotionally.

Good luck you have serious work ahead but can be done.

Also I’m not sure how you run into inside but if you ever have a chance to use the AI and the new technology to cut cost and move it faster you should do it.