My Worst Day As a Business Owner (Part 1)

Big Deal Small Business, Issue #121

Jun 30, 2025

Big Deal Small Business: My Worst Day As A Business Owner (Part 1)

June 30, 2025 | Issue #121

This is a blog written by Kaustubh Deo // Guesswork Investing about acquiring & operating small businesses. If you are a new reader / new searcher, please start here.

Side note — I’m planning an SMB/ETA golf retreat this November in San Antonio! In partnership with Bird Golf Academy, a searcher-owned business. If you’d like to join, check out the details here.

Level Set

Please excuse my dramatic title. In reality, I’ve had a lot of “worst” days as a business owner.

A sales arborist quitting with about 4 hours notice. Our bucket truck getting stuck in the “up” position at a client site. Our bucket truck blowing through multiple belts while stuck in a client driveway. A chip truck breakdown, leading to me sitting on the curb at a gas station for a couple hours, waiting for a tow truck. Chipper brakes catching fire on I-5.

You think I’m done? Here’s some more.

A crew accidentally breaking a second story window at a client site. An employee quitting to work for a competitor. A job being so underbid that I ended up paying another contractor to finish it for us.

The list could continue for pages. I could probably write a post about each one.

But this incident has been my worst-to-date, both for the immediate impact, as well as the resulting repercussions. I share this story to:

Give searchers a visceral sense of what being a business owner can be like.

Give fellow business owners some validation that this is HARD. They’re not the only one having some really bad days.

This piece is split into two parts:

Part 1 (today, for all subscribers) outlines the actual events of the day and the immediate aftermath.
Part 2 (next week, for paid subscribers) will outline the financial impact and the long-term repercussions.

Let’s dive in.

Sponsor Information

Big Deal Small Business is sponsored by Live Oak Bank, a leading self-funded search fund lender.

To learn more, reach out to Lisa Forrest and Sarah Andrews at Lisa(dot)Forrest(at)LiveOak(dot)Bank and Sarah(dot)Andrews(at)LiveOak(dot)bank.

Please mention that Kaustubh from Big Deal Small Business sent you!

It was a normal Thursday. May 18th, 2023.

We had completed our safety morning like we did every Thursday at 7am. The crews were off and had started up all their jobs for the day.

Usually, if something goes wrong at the first jobs, I’d hear about it by 7:30 or 8:00am, as crews get set up and begin work. If that time period passes without issues, we were usually in the clear.

That morning, I had a Zoom call scheduled from 8 to 9am. At about 8:35am, I got two calls from a crew leader — they’ve been instructed to call twice in case of emergency, so that I knew I needed to leave the meeting and answer the phone.

I pick up, and our crew leader gets straight to the point — one of our trucks had crashed.

It had been stationary, parked on a hillside in front a client’s home. We’ve parked on this hillside, with this truck, multiple times before as we have other client’s on the same street.

The truck had been parked for 15-20 minutes and the guys had started working. The wheels were even chocked.

The crew leader explained that the truck brakes & wheel chocks had failed somehow, and the truck started rolling downhill.

It hit a parked car almost immediately, pushing it all the way down to the bottom of the block, where the road met the cross-street at a T-junction.

Our truck pushed the car through that intersection. Along the cross-street, it hit another parked car, which still didn’t arrest its motion.

It went through that parked car and rolled straight into the house directly across the hillside. Here’s a poorly drawn sketch in Google Maps showing where the truck started (on the right side of the map) and the house it ended up hitting (at the end of the arrow) after the T-intersection at the bottom of the hill.

Home addresses and street names covered up for homeowner privacy.

We were lucky.

There was no one in our truck at the time. There was no one in the two parked cars. There was no one in the house. No cars drove through the intersection while our truck hurtled through. We were immensely lucky that there were no injuries.

My crew leader confirmed there were no injuries as we got off the phone. I texted him my ETA once I had mapped it, to which he replied: “Warning: It’s bad. Prepare yourself.”

I arrived at 9:05am to find our truck in a house and our crew sitting on the median planting strip. The parked car that got pushed all the way down the hill had ended up in an apple tree.

Here’s what the scene looked like:

The chipper was still attached to the back of the truck, having sustained no damage.

The house’s garage had been pushed in, and the truck had managed to hit a water pipe, causing water to begin pooling in the home’s basement.

If you’ve never seen a truck partially inside a house, well, now you have:

Now what?

What do you do next when you arrive at a scene like this? We triaged quickly.

How do we turn the water off to the house, to minimize further water damage?
Let’s get in touch with the homeowner & car owner.
How do we get the truck out of the house?

The homeowner returned home quickly and called her general contractor after we touched base. The car owner was also home, and I chatted with her, assuring her that we will get the situation rectified.

We went into the home to see where the water was leaking — thankfully, not a bad leak, but water was still coming in slowly. There was a puddle forming.

I dispatched two of the crew members to a nearby hardware store to buy mops & buckets so that we could clean up the water ASAP.

Then the homeowner’s GC arrived. Coincidentally, he knew our company — apparently we had worked on the trees at his personal home. He asked me how the seller was doing. Seattle is a such small town sometimes.

We jointly figured out how to get the water turned off — it required moving the homeowner’s car, which had also been hit by our truck and was in bad shape after being spun 90 degrees:

We managed to pull it off the water main cover by hooking up the vehicle’s front bumper to the GC’s truck and just dragging the truck a foot to the side.

This is one of those moments that I was so thankful that we were in Seattle — it’s a friendly, calm city. Locals treat each other kindly. In this scenario, both the homeowner and car owner were incredibly gracious to us — they knew it was an accident and they knew we were doing our best to solve the immediate issues.

I set up a camping chair for the homeowner to sit in as we problem-solved.

Removing The Truck

With all stakeholders in the loop, and the water damage mitigated, we turned our focus on how to remove the truck.

I started by calling a tow company — I already had two options in my phone (not my first rodeo towing these trucks…). Only a couple local companies can tow trucks this size.

While we waited for the tow truck, we needed to get the chipper off the truck — the tow truck wouldn’t be able to access the truck with the chipper in the way.

That chipper is around 8,000 lbs, and doesn’t have a front wheel — it’s only designed to be towed. Not exactly the easiest piece of equipment to maneuver when the tow hitch is facing 90 degrees away from the street, halfway up a small driveway.

We sent a couple other crew members back to the yard to pick up our other larger truck, which we would need to move this chipper. We also had some heavy-duty chains…you may be able to see where this is headed.

When the other chip truck arrived, we unhooked the chipper from the crashed truck, setting the trailer stand into the ground so it lifted off the truck. The chipper’s trailer stand doesn’t have a wheel on it, so it’s generally just stuck in place when it’s unhooked.

Given that, there was no way to get the trailer hooked up onto the other truck — first, we had to somehow reorient it 90 degrees to be lined up with the street.

Our solution — we propped up the trailer with some wood so that we could raise the trailer stand a bit. Then we placed several pieces of stacked plywood under the trailer stand.

The trailer was now propped on the trailer stand, which in turn was on top of a few pieces of plywood. We hooked up the trailer hitch to our truck with heavy chains…and slowly pulled.

As the truck pulled the chipper sideways, the plywood under the trailer stand started to move too, fanning out slowly like a deck of cards, allowing the trailer to rotate slowly.

Eventually the last piece of plywood was on the ground and the trailer had been rotated about 15-20 degrees. We re-stacked all the plywood under the trailer stand and did it again. It took 3-4 resets, but the chipper was now finally turned 90 degrees.

The backup chip truck took the chipper away, and then the tow truck arrived and began pulling the truck out of the house. Here’s what it looked like once it had been removed from the house:

To add complexity to the towing situation, the truck had to be pulled the wrong way down a one-way street to get out of the location. So I went and blocked the street at the end of the block with my car to stop any cars from entering the one-way street.

Immediate Aftermath

With the truck pulled out and headed to a mechanic shop (again, someone I had worked with previously) to assess damage, we dealt with the immediate issues.

The GC had called a remediation contractor to handle the water damage. They were getting to work.

I called my insurance team at Oberle, who walked me through the next steps:

File a collision report with the state
Begin the claim process with the insurance agency to get an adjuster assigned
Provide insurance contact details to the homeowner and car owner

I sent our guys home at that point — they were all freaked out by the incident, and there was simply no upside to attempting to push through the day. They didn’t have the truck they needed anyway.

To add insult to injury, we still hadn’t finished the actual work for the client…we had to reschedule that for the following week, with a plan to park along a different street just for peace of mind.

I also scheduled a team meeting for the next morning — we definitely needed a reset the next day to recover from the incident.

Friday morning, the full team gathered at the office and I gave them a quick summary of what happened — obviously they’d all heard from each other, but this gave us a chance to level set. We talked through what went wrong, but more importantly, what went our right — the on-site crew had handled the situation incredibly well.

They remained calm, they contacted me, they showed professionalism to all involved. While the situation truly sucked (no better word for it), I was proud of how they handled the aftermath.

Internal Processing

The above is a factual retelling of the day’s events. At the same time, as a business owner, you are managing your own emotions, right under the surface.

I was feeling a combination of relief, stress, and general anxiety.

Relief stemming from the knowledge that this could’ve been so much worse — there were no injuries.

The stress came from my brain immediately running through all the contingencies I’d need to sort out in the days to come. Do we need to rent a truck? We need to reschedule multiple jobs. How will the guys handle this?

The anxiety came from the unknown — this is a problem I’d never faced before. The potential downstream impacts were unclear and wide-ranging. Is the truck totaled? If so, how much recovery will I get from insurance? Will it be enough to buy a new truck? How will this impact my rates? What if this exceeds my limits?

In the moment, the actual first 24 hours of chaos, your role as a business owner is to manage the situation, which includes managing your emotions. It’s a time to hold space for your team and it’s a time to execute to mitigate the damage.

Once you’re past that part, you reach out to your support network. Your partner, your friends, your fellow small business owners — that’s the time to ask for help, even if it’s just having someone listen to you vent.

If I’ve learning anything as a small business owner the past few years, it’s that your ability to take a punch and keep going is 90% of the game. Your job is to continue pushing forward each day and not give up. Given that dynamic, having a well-built support network is a core part of being a strong business owner — you don’t get points for doing it alone.

End of Part 1

So, that all happened in the span of 24 hours. However, the impact on the business continued for months (years, really) — that’s the impact that small business owners really need to understand, so I’ll detail that part next week in Guesswork Unveiled (paid section, focused on SMB operations).

But for the searchers & search-curious who read this blog, hopefully today’s post gave you a bit of an inside look at what firefighting inside a small business can look like.

Feel free to reach out if you have any questions. Also, if any other business owners are up for sharing their war stories, I’d love to interview you and write them up! Just hit reply to this email.

Best,
Kaustubh Deo // Guesswork Investing

Big Deal Small Business