I Ran Operations From Series B to a SPAC to Bankruptcy to Acquisition. Here's What Founders Should Build Before Any of It.

I've been in the room for the whole thing.

Not just the fun part, the Series B announcement and the hockey-stick charts. I ran operations at Enjoy Technology through the entire arc a startup can travel: venture funding into hypergrowth, a public listing through a SPAC, and then the part nobody puts on a pitch deck, the down cycle, bankruptcy, and finally an acquisition. I've also built my own businesses from zero, so I know the founder's seat from the inside too.

Most operations advice you'll read comes from people who only ever saw the way up. That's a problem, because the way up teaches you almost nothing about what actually holds a company together. You learn that when the money tightens and everyone's watching to see what breaks first.

So here's what I learned, stage by stage, and what I'd build into a startup before any of it happens.

Hypergrowth: your systems are the ceiling, not your ambition

When the funding lands and the mandate is "grow," it feels like the only constraint is how fast you can hire and spend. It isn't. The real constraint is whether your operations can absorb the growth without tearing.

I helped scale fulfillment operations across a network of 13 fulfillment centers, all of it during COVID, which is to say under the worst operating conditions I've ever seen. And I did it cross-functionally, in the seams between field ops, construction, workplace, real estate, security, and procurement, because that's where scaling actually happens: not inside one tidy department, but across all of them at once. What I watched over and over was simple: the business could always sell faster than it could deliver. Every time growth outran the systems, the gap filled with heroics, people working nights, tribal knowledge, one person who "just knows how we do it here." Heroics feel like momentum. They're actually the sound of your operation running out of runway.

The lesson: growth doesn't reveal a great business, it reveals whether you built one. If your processes only work because specific people are grinding to hold them together, scaling doesn't fix that, it multiplies it.

What I'd build early: document how the work actually flows before you need to. Not a binder nobody reads, a living system that a new hire can follow on day one. The cheapest time to write it down is before you're drowning.

Going public: "we'll fix it later" stops being an option

Then we went public through a SPAC, and the whole environment changed. Under public-company scrutiny, the operational corners you cut in the growth phase don't stay hidden. Reporting, controls, investor expectations, all of it shines a light on how the business really runs behind the numbers.

This is where I learned to think about operational debt the way engineers think about technical debt. Every manual workaround, every undocumented process, every "we'll clean that up after the next sprint" is a loan. It carries interest. And the interest comes due at the worst possible moment, when someone with real leverage is finally looking closely.

The lesson: the operational debt you take on to move fast is real debt, and you rarely get to choose when you repay it.

What I'd build early: legibility. Build the business so an outsider, an investor, an auditor, a new executive, can understand how it works without a translator. If the only way to explain your operation is to have you in the room, you've built a liability, not an asset.

The hard part: what fails first when the money tightens

About a year after going public, the company filed for bankruptcy.

I'm not going to pretend that was anything other than brutal. But I'll tell you what I saw, because you can't get this lesson from anyone who's only ridden the way up: when the money tightens, the first thing to fail is anything that depended on abundance to work. Processes that only functioned because you could throw people or dollars at them collapse instantly. The stuff that survives is whatever was built to be efficient and legible in the first place.

Downturns don't create operational problems. They expose the ones that were already there, the ones hypergrowth let you paper over. Every weakness I'd watched us defer during the good years showed up at once, and there was no budget left to buy our way out of any of them.

The lesson: build like the money will get tight, because at some point it will. A business that's operationally lean and well-documented has options when things go sideways. A business held together by spend and heroics has none.

Acquisition: someone finally inspects the machine

The story didn't end at bankruptcy. The operation had enough real value that Asurion acquired it. Across my career, at Apple, Tesla, and Asurion, I've operated inside serious security and compliance regimes, environments where "the operation behind the audit" has to be real, not theater.

Here's what that taught me about acquisitions and diligence: a buyer isn't really buying your growth chart. They're buying whether the business can run without the specific people in the room. Diligence teams look for documented processes, clean data, systems that actually connect, and a company that isn't one departure away from falling over. A startup that lives entirely in the founder's head gets priced down or passed on, because to an outsider, that founder walking out the door is the whole risk.

The lesson: build for the diligence you hope you'll one day face. Operational legibility isn't bureaucracy, it's what protects your valuation when someone finally inspects the machine. And the beautiful part is that building for that outcome makes the business run better every single day in the meantime.

The one thread through all of it

Every stage taught a version of the same thing. The founder, or the handful of people everything routes through, becomes the ceiling. Growth stalls on their bandwidth. Debt hides in their heads. Downturns expose what they never had time to build. Buyers discount what only they understand.

The fix is never "work harder." It's to get the operation out of the founder's head and into a system the business actually runs on, documented, standardized, measured, and owned by the team instead of trapped in a person. A company that runs on a system can scale, survive a downturn, and sell for what it's worth. A company that runs on a person can do none of those things reliably.

That's exactly why I do fractional operations the way I do. Most fractional execs quietly build dependency, a seat they never give up. I do the opposite: I build you a running operation you own, and I aim to make myself less necessary over time, not more. I've seen where the road goes, all of it, and the businesses that make it are the ones that built the system before they needed it.

If you're a founder who can feel the operation starting to strain against your own bandwidth, that's the signal, not a crisis yet, just the early warning. It's the best possible time to build. Let's talk about where your business is stuck, before the bill comes due