The story of my mental breakdown on the side of the road in 2013 and how my business almost failed

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Failure, contrary to popular belief, is a huge part of business. You’ll have let downs more often than wins. You, as the owner of the business, deal with all of the problems.

Customers don’t ask to speak to the owner in order to thank them for doing exactly what they expected your company to do. They speak to the owner because they are pissed.

For every great thing that happens, you’ll deal with 5 problems.

Keeping a level, unemotional attitude during stressful situations is 95% of entrepreneurship. If you get rattled when your day doesn’t go as planned and turn into an emotional wreck like most people, you are not cut out for entrepreneurship.

And here is the cold hard truth:

Most people are better off getting a job than becoming an entrepreneur.

When is the last time you read that in a book about entrepreneurship? It is the truth.

For most people, the best quality of life can be achieved by going to work for a good boss at a good company and earning good money with minimal stress. Some stress is always good because it keeps you challenged and keeps you from getting soft, but you can get that from a job without worrying if you’re going to be profitable next month.

Most people don’t thrive in chaotic environments. Most people hate sales (and sales is the name of the game, as we’ll discuss in a later section). Most people are risk averse when it comes to finances. Most people can’t handle life’s uncertainty let alone an organization with 50+ individuals where every problem ends with YOU.

I’m about to tell you a story here that I haven’t told many people.

It was 2013 – our first operational year in Boston. It was the year I drove the box truck we had purchased on the south side of Chicago for $2200 to Boston and moved-in with my girlfriend (who is now my wife).

As you read earlier, I painted the town with chalk and flyers. I spent 8 hours a day for the entire month of March and half of April sneaking in dorms, passing flyers under doors, and drawing chalk advertisements for our services in high traffic areas on campus.

Our business wasn’t a real business yet. We were struggling through things like insurance and permits. We had just gotten workers compensation a few weeks earlier. My partner and I were running around like chickens with our heads cut off and despite taking 20+ business classes in college, nobody had told us anything about any of this stuff.

We were half of a business at that time. We had a bunch of “good enough” processes in place to handle a very small amount of business in 2012 – about $80k in revenue from 253 customers.

My skills were also under-developed. I didn’t know how to build processes. I wasn’t the best decision maker. I didn’t know how to delegate. I wasn’t a great leader. I was a below average communicator. I was emotional and immature. I was just an excitable 23 year old who knew how to work really really hard.

It was literally just me and a truck in Boston. I had one guy hired from craigslist and he was traveling around with me drawing chalk ads on the ground and dishing flyers for $15 an hour.

But by April 15th, about a week before go-time, we had over 300 customers signed up in just Boston. And they were pouring in by the hour.

From April 15th to about May 15th I didn’t sleep more than 3-4 hours a night. From May 4th to May 9th the peak days of pick-ups, my partner and I worked around the clock. We were driving trucks during the day, answering customer service emails all night, trying to keep enough employees on the schedule to survive, and we barely made it.

At one point during Northeastern finals week in late April we got a customer service call at 4:30am in the warehouse. Dan and I were both still awake unloading trucks and I answered the phone. It was a customer who was at the airport preparing to get on a 6am flight to China but she had packed her passport in one of her boxes.

Within 40 minutes of the call we had found the passport, driven it to the airport, and handed it to her. She was thankful and we were proud. I still have the picture saved on my computer of me smiling and her looking at me like I was an idiot.

We ended up with a full warehouse and over 700 customers in it. We had picked it up over a 1 month period and it was insanely stressful. But we had done it and we were proud. Our revenue had 4x’d over the previous years and we were going to be profitable. It was a huge win and we celebrated with a ton of $2 beers at a dive bar near the warehouse in Everett MA.

We spent the summer putting out fires, executing one-off pickups or deliveries, and largely oblivious to what was to come.

Here is something you might not realize about the student storage business:

Pickups are way easier than deliveries.

To execute pickups, you need to arrive at a specific time window with an empty truck and a dolly. To execute deliveries, you need to arrive at a specific location during a specific time window with the customer’s stuff.

The schedules have to be made in advance, the items need to be organized carefully on a delivery truck in reverse order. The items need to be labeled correctly so you can locate all of them! And if a customer changes an appointment or isn’t available to accept delivery, you have to work around those items the rest of the day, bring all of those things back to the warehouse, and then re-organize the stuff in the warehouse so you can find it when you go to load it up the next day.

Deliveries is 5x the stress as pickups considering the same volume, and the stress is all dependent on how good of a job you do with warehouse organization and labeling.

And in 2012 when we picked up all of those items with inexperienced employees, shit processes and little to no sleep, we DID NOT do a good job organizing the warehouse or labeling items. There were full orders left unlabeled. Only about ½ of the customers were even input into the warehouse locator, and a ton of one-off items weren’t labeled.

I had all summer to solve that problem. To look and think about warehouse organization and think about solving it. But I didn’t. I just lolly gagged around and waited for the inevitable hurricane to strike me right in the face.

On top of that – the schedule in Boston is nightmarish for what we do. Every lease in the city starts on September 1st and the first day of classes at all 7 of our colleges there is always the Tuesday after Labor Day.

And in 2012 the start of classes was September 4th, meaning we had 3 days, the 1st, 2nd, and 3rd to deliver all 700 customers. Each truck could fit 25 customers, so that meant 28 customers in 3 days, or about full 10 trucks per day.

I was too dumb to even do that math until about a week beforehand, and by then it was too late. I couldn’t hire enough employees and the warehouse couldn’t be reorganized in time.

We waited too long to reserve truck rentals and they were all taken by the time we tried. Remember, the entire city moves on that one weekend, and all of the moving companies are slammed as well. We had to rent trucks in outside cities and scramble. We only had 5 of them.

Later on we started renting 2x the number of trucks needed so we could load the mall a day or two beforehand. This made our lives way easier. But we were not that smart this year.

The hell started on August 29th when me and 4 of my employees were tasked with beginning to load the first 5 trucks worth of stuff, staging the next 5 trucks, and getting organized.

I realized the warehouse was a clusterfuck and 200 items across 150 customers of the 700 weren’t labeled and we didn’t know where anything was. I also started creating the schedule for the deliveries (I had no employees to do that) and realized we didn’t have enough employees. I had too many things I needed to do so I wasn’t able to go out and recruit, hire and train new folks.

I still, on the 29th, didn’t understand what I was in for – but I was learning fast.

I stayed up all night that night organizing customers and moving the warehouse around. I was already sore and chafing from the labor. I fell behind on scheduling so I had to do that from about 4am-8am that night as well. And i hadn’t notified my employees of their shifts, so I did that for the week from 8-10am, and then I got to work loading trucks.

After I sent out the initial schedule to all 700 customers I started hearing back from them with change requests. By 5pm when I was done working with the guys and they headed home I had over 200 customer service emails to sort through.

I knew at this point I was screwed. I didn’t have enough employees. I needed 10 people full time delivering items all day the 1st, 2nd, and 3rd but I had heard back from a few employees with excuses and that they were bailing. My partner flew in. His brother flew in. His brother’s friend flew in. We had 3 guys drive in from our Ithaca branch for the week. We couldn’t afford hotel rooms because the entire city was booked out with all of the moving going on and parents in town, so they slept in the warehouse on customer’s mattresses (with plastic covers, of course) and walmart sheets I had to run and buy at some point on the 31st.

By the 31st we had 5 trucks, or about 125 customers, loaded for the next day but I hadn’t slept since the night of the 27th. But it was all happening. I was getting customer service calls and answering them non stop. The scheduling was a mess. I was using Google Sheets and at one point I accidentally deleted 25 rows but didn’t know which ones so I had to re-build the schedule from scratch and re-notify everyone. It was horrific.

The morning of the 1st came and I had 8 employees at my disposal. 3 had to stay back at the warehouse and keep pulling orders and preparing for the next day. So me and my partner and his brother each ran a truck all by ourselves that day.

We had two types of customers, room service and main entrance. I took the truck with room service only because I knew my employees would quit or not show up tomorrow if I made them do the hellish routes. And this was my mess. I had to go down with the ship.

From 8am-2pm I drove around the box truck, answered customer service calls and hand-delivered boxes. It was the Bay Street brownstones at BU’s campus that I delivered. All of the boxes went up 2-4 flights of stairs. By hand. 150 items.

I was behind schedule so I didn’t have time to eat or rest. I was chafing really horribly at this point and was bleeding at the tops of my thighs. I had to stop at a Walgreens to get antibiotic ointment and gauze along with deodorant and a pack of undershirts and underwear. I realized I hadn’t showered in 4 days and was in close quarters with customers so I had to do something about the stench.

I got back to the warehouse at 3pm and picked up another full truck and set out to deliver all of the items on it once again, alone.

My wife had just gotten off work and she made dinner for all of our crew at the warehouse. She also let our travel guys come in and shower at our little apartment. I wasn’t part of those festivities but she ended up spending the entire weekend running around making sure our guys were fed and as comfortable as possible.

By 10pm when I got back to the warehouse I had a fever of 102 and my chaffing had stained my jeans with blood. I threw away the clothes, took an ibuprofen, and spent the night answering customer service calls, making schedules, and loading trucks for the next day.

I wasn’t done loading the last truck when the workers all arrived at 8am. I made sure they had their dollies, battery packs, clif bars and sent them on their way. I finished loading my truck at 10am and hit the road, 2 hours behind when I was supposed to start.

I finished the last delivery of the second truck by about midnight that night. My partner and his brother were on about the same schedule as I was and they were also dealing with their own physical ailments.

My right foot had locked up from the constant gas / break transition while driving the truck and a case of tendonitis was hitting me. I was in hell. Looking back it is all a blur. I remember multiple times wondering what the hell I’m doing with my life. This business will fail. There is no way we can do this. It is impossible and I have failed.

We pushed through and Dan and I spent the night loading up the next 5 trucks for the morning shift.

The next day, the last big day of deliveries and the day before classes started, was the biggest. Most customers had selected this delivery day and we had a TON of messy one-off items that had missed their first delivery attempt because they weren’t labeled properly or we messed something else up.

A lot of our customers were pissed. Our inbox was full of complaints. We were late to virtually every appointment by 30 minutes or 4 hours.

But the deliveries had gotten done so far.

It was all at the expense of my team, however. My employees were burnt out. They had worked 40 hours in 3 days. And it was manual labor for pissed off customers. Their tips sucked because I had done a poor job with the schedule. They got a lot of complaints. And they were physically exhausted from working 8am-10pm.

5 of the kids stuck by us. I remember them all by name and I would kill for those kids now. They layed it all on the line and suffered through. Never complaining. Always showing up. They’ve all moved on to bigger and better things and are ultra successful at this point, all these years later.

That day, September 3rd 2012, I had a mental breakdown on the side of the road in Boston and it was the lowest I’ve ever been.

I hadn’t slept in nearly a week. I was bleeding between my legs and my hands were blistered and cracked. My feet were blistered. My right foot wouldn’t move. And I had lost 20 lbs off my 6’3 inch frame.

I remember where I was standing. It was on Park Drive right near the intersection of Buswell Street on Boston University’s south campus. I had just delivered a customer’s 10 items up 5 flights to the top of a brownstone when my phone rang. It must have been about 3pm because I had just finished my last delivery and my truck was empty.

There had been a fair share of accidents already over the previous few days. An employee put gasoline in a diesel engine and it had to be towed and we were greeted with a $5,000+ repair bill. That was outside of the insurance coverage as well.

Another employee had ripped the top off one of our trucks by driving it down storrow drive. That also wasn’t covered by insurance and we were also given a ticket and I lost that truck and my employee for 5 hours over that ordeal. The cops had to shut down the road and back him all the way out with escort.

What did I expect? These employees weren’t trained. They weren’t qualified. They were 18 year old kids out in the big city driving 10,000 pound pieces of equipment. I asked for these problems with my own stupidity.

When the phone rings during chaos you know it isn’t good news. If your partner calls. Your employees. They are calling you with problems.

My phone rang there at 3pm

It was one of my employees. He had side swiped a BMW on harvard’s campus with the one box truck we owned. That means the claim was on us. If he had done it in a rental it would have been fine because we bought the insurance on all of them. But it was our truck which had also assumed a lot of damage. It was also my personal insurance policy because we couldn’t get business coverage. He sent me a photo. It wasn’t good. He had ran down the entire side of the vehicle. Ruining the rear quarter panel, both doors and the front quarter panel. Maybe totalled.

This wasn’t good.

He was telling me what happened when my partner dialed in.

One of our other employees had quit and left a full truck stranded over on Northeastern’s campus. He was fed up with the long hours and said screw this. He locked the truck, hid the key and texted Dan to tell him where it was hidden and that he was done.

But his truck had 25 customers on it that were expecting their stuff so that really sucked. We were already 2 hours late on that schedule, which was supposed to start at 1. I still had to go back to the warehouse and get my second truck of the day. I said I’d make my way over there and hung up.

All of the google voice calls from customers were transferred to my phone and I had been ignoring them all day. They were coming in hot now, one per minute. I sat down on the curb and hit ignore. Another one called and I hit ignore again. Then another.

And right then I felt the overflow of anxiety and slipped into my first ever panic attack. I became hysterical. Crying. Curled up in a little ball on the side of the road. It was 15 minutes of hell. I felt out of control for the first time in my life. In over my head. Like my business was slipping away and failing right in front of me and it was all my fault.

I picked up the phone and called my mom. I don’t know why I picked her. I guess I wanted the comfort of home. I wished I was back home. Back to safety. Instead of this big city going through hell and losing so much money.

She tried to console me but couldn’t. I knew I had made a horrible mistake and that she would only worry about me, so I played it down and got her off the phone.

I called my partner next. I told him I couldn’t do it. That it was over. We failed. I cried.

He told me to get my shit together. We’re close to the end, he said. He was in hell too, he said. But we’re in it together and if I lay down on him he is fucked. He told me that I was a badass and that if anybody could do it I could do it.

He lifted me up over the next 30 seconds and I snapped out of it. I hung up and pulled myself together.

I put one foot in front of the other. I got in the truck. I drove to the other truck. I just did what I could do in that moment. I kept ignoring the calls. I just kept delivering boxes. And about 24 hours later it was all over.

The phone stopped ringing. The warehouse was nearly empty. It was over.

And I came out the other side a harder man with a new perspective on what true stress was and what failure really looked like.


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About Me

I started the Sweaty Startup in December of 2018 because I believe the Shark Tank and Tech Crunch culture is ruining the real spirit of low-risk entrepreneurship.