I lost it all. Here's what happened after the lunch wagon thread.

[Mr Shave]

Over a decade ago I documented my first coffee truck here. What followed was an amazing ride. 9 more locations, a license deal, subleasing, bootstrapping, roasting, competing and getting humbled at the USBC, traveling to origin. Being leveraged to the hilt, destroying my credit, getting engaged, ending the engagement and losing it all.

For years I felt like a failure. Like I was so close to taking it further and just couldn't get there. It was a lot of pain for a long time.

I wish I had kept a journal through all of it. Looking back at my old posts from the truck buildout I love seeing the energy and optimism. There is a lot that came after worth sharing.

AMA to kick it off then I will start filling in the lessons and things I wish I had known.

TLDR; A friend asked me if knowing what I know now and the same outcome was guaranteed,
would I do it all over again. I would.

 

[Mr Shave]

The Six Things That Haunted Us
I don't think there was one single thing that broke it. Looking back, it was circumstances I responded to, and some of those responses compounded on each other until the weight was too much. Here's what I wish I'd known.

1. I started as the wrong type of business.
Sole proprietorship. Quick, easy, done. What I didn't understand was that when I had to shut that down and incorporate as an LLC, the clock reset. In the eyes of banks, we were a brand new business. All that time building something real, gone on paper. That cost us more than I realized for years.

2. I had no real vision or plan.
I wanted to make a great product, be a good place to work, and never lose a customer. That was it. I had no idea what the exit looked like. No idea what we were building toward or why. I cared deeply and worked constantly, but caring and working aren't a strategy.

3. I never subscribed to Profit First.
Everything went back in. Every dollar, every margin, reinvested to grow. It felt like discipline. It felt like commitment. What it actually was, was a slow bleed. More hours, more equipment, more service windows, more espresso machines, branded cups, diminishing returns on all of it. Revenue is vanity. Cash flow is sanity. I learned that the hard way.

4. I had no board. No real accountability.
I had friends. I had people in the industry I respected and talked to. But I never had a small group I sat down with quarterly, people who would look at the actual numbers, ask hard questions, and hold me to a plan. That absence cost me. A lot.

5. The debt spiral almost broke me.
Factoring. Cash advances. If you know, you know. The APRs are predatory and the pitch is seductive when you're desperate. The math never worked. The solution was always "grow your way out of it," more sales, another location, expand. So we did. And then we needed another advance. Wash, repeat, sink.

6. I was afraid of real capital, so I stayed undercapitalized.
I cashed out my 401k. Paid the early penalty. Bootstrapped everything because I was terrified of debt and wanted to own it clean. What that actually meant was going into every expansion underfunded, with no runway, no margin for error. Sometimes I look up what I sold to build out that first truck, Nvidia shares, and I laugh, then I want to cry a little. The irony isn't lost on me.

None of these are unique. That's almost the hardest part. These are the same mistakes a lot of people make. But knowing that didn't make them hurt less. It just makes me want to say them out loud so maybe someone else catches them earlier than I did.

 

[Mr Shave]

The Locations, One by One
I ran a lot of spots. Here's the honest recap.

Location 1: College Campus, Main
The cash cow. We were one of six concepts in the building alongside Dominos, Panda Express, L&L, and others. We did a third of the entire building's sales. The problem was commission was a straight percentage with no cap, so the better we did the more we paid. We eventually lost it to Dunkin Donuts. That one hurt.

Location 2: College Campus, Library Cart
The other side of campus. There were grand plans to redevelop the site into something permanent, and I thought being there was building goodwill with the university. Everything had to be broken down and hauled back to the main location every single day. Heavy on labor, light on upside. The redevelopment plans didn't get published until ten years later. The site still hasn't reopened.

Location 3: First Off Campus
An amazing space. Roughly 250 square feet, no wifi, no AC. But it was on the right side of the street, had real foot traffic, zero coffee competition, and neighboring tenants with office hours and a restaurant so we could actually use the parking lot. This one worked.

Location 4: Mall Lease Takeover
One of the highest grossing open air malls in the region by sales per square foot. We took over a sublease from a waxing place that couldn't get out of their lease when their full buildout opened upstairs. That should have been the warning sign. We were told we'd be in the mall directory. That was verbal. We had to follow mall hours or get fined, which meant staying open until 9pm with zero foot traffic. We were sandwiched between a satellite DMV and the trash pickup area in the basement. We couldn't change the signage so we looked like a pop up inside Beyond Bare Waxing. There were a lot of Brazilian waxing and coffee jokes. It was not awesome.

Location 5: Cancer Center
An opportunity to open on the med school and cancer center campus. The plan was to run coffee and bring in a food partner to handle the kitchen. First two partners had serious professional experience and both backed out. We went with someone newer. Our proposal was strong but we had committed to a 100 item daily menu for a small captive population. Eventually they pulled out too. We brought in another partner but by then we were just chasing it. Fully built out kitchen, incredible opportunity. We fumbled it.

Location 6: Licensing Deal
A couple wanted to get into coffee. We helped them build out a coffee lab and coffee school, then they wanted a brick and mortar. Found a great location, co branded it, and had real plans to expand internationally if things went well. The problem was we weren't aligned on approach and we both wanted control of the brand. It ended at the close of the agreement.

Location 7: Mall Number Two
Apparently we didn't learn from the first mall. A new mall opened on the other side of the island. Their coffee tenant wasn't going to open on schedule so they offered us a space. Free rent until the other tenant opened. It was basically a vanilla shell with drywall and a big drape backdrop. We were already stretched on staffing. The thinking was that zero rent and no utilities would help cash flow. It didn't save us.

Location 8: Former Peet's Takeover
An asset sale. The buildout was done, the location was great. First time working with a large corporate landlord. Sales never took off and it became a distraction. I loved that spot though.

Location 9: Flagship Bar
Two blocks down from the original off campus location. Bigger, better, parking lot, great street frontage, and a landlord who genuinely wanted to work with us. This was supposed to be the flagship.

Location 10: First Out of State
Everything was going well so naturally we opened off island. We had solid workers but no single strong manager on the ground. Issues piled up and were hard to manage from a distance. The nail in the coffin was a drunk driver crashing through the front window. Once the boards went up, what little traffic we had disappeared with them.

The Exit
The first off campus location and the flagship down the road were sold in two separate transactions. One was a partnership deal, the other was an asset sale with a lease guarantee. The non compete radius in the second deal made the first deal complicated. We exited both. The university location was already gone by then. We went dark on the out of state spot and the former Peet's.

That's the map. Ten locations, a lot of lessons, and most of them learned the hard way.