Cry Me a River

I only get hired when shit’s really, deeply, spectacularly fucked up. Think Barack Obama getting elected after the Great Recession or Dusty Baker riding in to clean up the Houston Astros’ cheating scandal. With that, I joined as the Director of Engineering at a tech startup.

Clean Up

When I started, the iPhone and Android app was barely a month old and already in shambles. Picture an app that crashed randomly when a user dared to log in. It was a buggy mess, functional only in the sense that it took up space on your phone. The CEO was furious, ranting about how it was already six months late, and the Chief Technology Officer (CTO) looked like he hadn’t slept in as long. He was trying to fix bugs himself while managing a team of not very experienced developers, and the cracks were showing. They were both desperate—scratch that, thrilled—to have me take the wheel.

So, I whipped out the fundamentals—the unglamorous stuff no one really wants to do but needs if they don’t want the product to implode. Daily stand-ups to keep everyone accountable. Sprint planning so people knew what the hell they were supposed to get done that week. Agile principles to keep things moving without all the chaos. And unit tests—yeah, I made everyone write tests, even though they whined it was “slowing them down.” It wasn’t rocket science, but it was exactly what the team needed: structure, discipline, and a playbook that would actually get them to the finish line in one piece.

The Takeover

My changes were paying off. The app wasn’t crashing every five minutes, the team was actually proud of their work, and morale was through the roof! For the first time, people were excited to log in on Monday. It was the honeymoon period, and I was riding high.

Then the CEO called me. She asked, “How ambitious are you?” I told her, “Unlimited.” That’s when she laid it out: ever since my first interview, she’d been so impressed with me that she’d been planning a little coup. The game plan? Fire my boss, the CTO, and hand me the role. Did I want it? Absolutely.

She took it to the board, they signed off, and the CTO walked out with a golden exit package. Two weeks later, I was running the entire engineering team. I held off on taking the title right away, though—didn’t want it to look like I snaked my boss. But make no mistake: this was my show now. I was even able to poach some of my favorite developers from previous companies.

Worse Than Hackers

With the app finally working, I was ready for the usual security nightmares: data leaks, hackers, the kind of late-night panic that comes from knowing every line of code has a target on its back. But nothing prepared me for what actually hit us.

See, this app wasn’t for just any marketplace. It was a platform for child adoption—a highly sensitive and emotional arena. And with that came a whole different breed of chaos. First, it was fake moms. Scammers spinning stories to wring money out of hopeful families. Then, we got hit with relentless waves from anti-adoption activists, people hell bent on tearing down our mission from the inside. And the worst? Death threats. Some aimed at the company in general, others directly at our employees by name. I knew about anti-abortion groups. But this? This was something else entirely.

In a matter of weeks, my role shifted from CTO to crisis manager, and the stakes had just gotten a whole lot higher.

Show & Prove

Now that no one was murdered by radicals, It was time to work on a product I could truly call my own—something I’d build from start to finish. The target? Adoption agencies. These places were using janky SurveyMonkey forms and mountains of paperwork to do the most crucial work of their lives. It was a mess. And these weren’t tech-savvy, app-happy users; we’re talking older women, buried under stacks of paper, running every process by hand.

A full digital overhaul would’ve been a nightmare for them, so we didn’t force it. Instead, we found a middle ground. I built out a clean, streamlined app, something they could handle without needing to become tech pros. We kept it simple: PDF forms, DocuSign-style approvals, and a dashboard to help them stay organized.

My approach? One major product or feature a quarter. Before I joined, they’d waste months writing these 40-page requirement documents that got them nowhere—no timeline, no accountability, just pages of dreams that never made it off the paper. I took a different approach: prototype to MVP to V1. And instead of guessing how long it’d take, I set a hard deadline—three months out, March 1st.

Did we deliver on time? Hell yeah! For once, the agencies had a tool that actually worked for them, not the other way around.

Moving the Goal Posts

Here’s what happens every damn time I take over a failed project: it’s like walking into a locker room of a losing team, dragging them out of last place, getting them to mid-tier, and suddenly everyone expects a Super Bowl win this season. The team might be on track, but leadership? They’re already shopping for rings and trophies.

Worse, the good habits slip. Everything I put in place—the culture, the processes, the rules for how we’d actually win—start to get ignored or excused away by everyone outside my team. My engineers stuck to the playbook, but other departments? They slid right back into their old chaos, the exact stuff that tanked the project in the first place.

The first sign of trouble came soon after we started building the SaaS app. I got asked for status updates and milestones. Fine, fair. But what they really wanted was linear progress, like a conveyor belt: 10% done each week for 10 weeks. Software just doesn’t work like that. It’s binary—it’s either working or it isn’t. Realistically, you spend the first few weeks barely scratching 10%, then you jump to 50%, and that last 10% can eat up 90% of the timeline. I explained it to them. They nodded along, but soon enough, they were sweating bullets and asking why we weren’t further along.

Then, when the product launched, I kept it controlled—alpha, beta releases—because real users always uncover issues you couldn’t find in tests. I set expectations clearly: the first customer would be smooth. The next two or three? Rocky. We’d need to iron things out. By the time customer number 7 came in, everything would be tight.

But no. Every time a bug surfaced, my personal cell phone lit up. “Why aren’t your engineers working nights and weekends?” “Tell your team to have more urgency!” But I knew the drill, knew how this would play out. I kept them calm, told them to trust the process. Sure enough, it worked out just as I’d predicted. Because I've done this plenty of times before. I know how to deliver, even when everyone around me is losing their shit.

Board Meeting

I flew out for a board meeting, the timing was perfect. Things were going well—so well that the board members and venture capitalists wanted to meet me. I got some face time over lunch and a long walk through the city with a few of them. It was obvious: I was getting vetted for bigger things.

At the meeting, I gave a strong presentation. Laid out our progress, our roadmap, and the clear, positive outlook. The board concluded, if we hit even modest sales numbers, we’d secure the next round of funding, no problem.

Later, at the fancy dinner, I did what every good leader does when things are running smoothly. I gave credit to the team. Took a minute to call out one person in particular—a developer I’d brought over from my last company. “This guy’s better than me,” I said, which was true, by the way. He is a better developer than me, it's just that I'm the CTO, not a developer.

I’ll never forget the look in the CEO’s eyes: not surprised that I’d give credit where it was due, but something else like "How ambitious is he?"

Indecision is a Decision

The high from the board meeting didn’t last long. The next month came, and we missed our sales target right out of the gate. And there was a reason for that: we were split between two products. On one side, we had the mobile app—a consumer-facing platform connecting expectant mothers with families looking to adopt. Sleek, sexy, and it looked great on paper. But here’s the kicker: it didn’t make money. Then there was the SaaS app, built for adoption agencies. It was utilitarian, less glamorous, but it actually brought in revenue.

The board wanted the CEO to make a call: go all in on B2C with the mobile app, or focus on the B2B SaaS platform for agencies. It wasn’t just a matter of business strategy; doing both was a flat-out conflict of interest. No matter how we spun it, our adoption agency clients saw us as competition. We could preach “separation of church and state” all we wanted, but they knew we were undercutting their prices and aiming to disrupt them. They didn’t like it, and they didn’t trust us.

But here’s the real problem: the mobile app was the star of the show. It looked good, it was flashy, and everyone loves something they can brag about at Silicon Valley cocktail parties. The SaaS app? Solid but boring. It’s not the kind of thing you show off to friends and family. But it was the one actually keeping the lights on.

The CEO was supposed to make the call. B2C or B2B. But she couldn’t choose, so she didn’t choose. And when you don’t make a decision, you’re still making one. We stayed split, riding the line between two worlds, too distracted to succeed in either one.

Accounting Tricks

The coverup is always worse than the crime. When we couldn’t hit our sales goals—and not because of the product or engineering—the CEO pulled an accounting trick to make the numbers look good. Instead of charging adoption agencies a straightforward subscription fee like any other SaaS app, we started charging their customers for the entire adoption process, skimming off a hundred bucks and sending the rest of the cash straight to the agencies. It looked like revenue on our books, but it wasn’t revenue from our actual software, the product we were supposed to be selling. After credit card fees, we were practically giving the app away for free. But on paper? We were “hitting our targets,” setting the stage for the next funding round.

I kept wondering: How did the board not catch onto this? They got monthly reports, and the CEO’s little scheme was obvious to anyone with even basic financial sense. But they stayed happy and oblivious until the next board meeting—when the penny finally dropped.

My first board meeting had been upbeat. This one? Just the opposite. Didn’t matter that I had a solid presentation ready, or that we’d rolled out new features left and right. No one cared. I got the hint—shut the fuck up. I could read the room, and if they didn’t want to hear from me, fine. I was happy to be seen and not heard while the CEO tried to talk her way out of the mess she’d created.

Silicon Valley Bank

A few weeks later, my phone lit up in the middle of the night on a Saturday. It was the CEO, frantic. Our biggest VC had tipped her off: Silicon Valley Bank was about to collapse. And where was all our money? Sitting right there. She and the CFO were scrambling to pull out whatever they could, but my job? Keep the company calm when this news hit on Monday morning. Suddenly, my ability to keep people steady under pressure had become the most valuable asset we had.

This wasn’t just another bank in trouble—this was Lehman Brothers failing all over again, the spark that had triggered the Great Recession. And this time? It was poised to be the bomb that set off a wave of tech layoffs and froze venture funding.

If the Fed didn’t step in to bail out Silicon Valley Bank, we weren’t just missing payroll that Friday; we’d be out of business, along with 40,000 other companies. It was the kind of existential threat you don’t forget, and the entire company’s future rested on whether or not the government would swoop in to save the day come Monday.

Make a List to Santa

Shit got real. No more time for fun and games. I was told to make a list of three people to let go. I pushed back—hard. I’d seen the financial trouble coming from our missed sales targets, and I’d already made cuts in my department. I’d let an under-performer go, cut out expensive contractors, and run a lean, efficient team. If cuts needed to happen, maybe other departments should take a look in the mirror. Hell, I even offered to help with sales since that was the actual problem—not engineering.

But here’s the thing about working for startups: often, you’re surrounded by people who haven’t done this before. The CEO had never been a CEO or a founder. The head of sales had zero sales experience. I was the only one in the company who’d even been in sales, and I was damn good at it. But no, my offer to help drive revenue wasn’t taken. It was like saying, Hey, you want to actually make money? and getting blank stares in return.

I managed to buy some time, enough to quietly nudge my teams to keep their LinkedIn profiles open to recruiters. But eventually, time ran out. They wanted a list, and I had to give it to them. My name was on it.

Call My Bluff

The CEO was stunned. Who volunteers to get laid off? I laid out my reasoning: I knew the books, knew I was the highest-paid person in the company. My value should be obvious. I didn’t just turn the company around; I’m the reason we’re still here. She agreed—over and over—but I didn’t need her to say it; everyone knew it. Then I reminded her that people had followed me to this company, some of them to multiple companies. They had wives, kids, mortgages. We should be strategic about who stays, it’s us.

Monday rolled around. In our morning meeting, she let me know I’d been let go. Thanked me for saving her company, said my volunteering was the bravest thing she’d ever seen, that it was the hardest decision she’d ever made. And then came the tears. Ugly, face-scrunching, crocodile tears, pouring down. She told me the board had approved a “very generous” exit package for me, and when I asked if she’d saved the people I requested, she swore she had.

She lied on both counts. The old CTO left with a golden parachute; mine was cheap plastic. Two weeks of severance—two weeks. For my level, six months’ salary is the industry minimum. If you are going to fuck me, at least leave some money on the nightstand.

Runways are for Models

The problem with marrying your mistress is that you need a new mistress. I guess the CEO forgot to ask my replacement how ambitious he was, because a month or two after I left, he quit on her. And where did he go? Right alongside me—we started our own startup.

The real reason I volunteered for that layoff? I know a sinking ship when I see one. Startups are simple: VCs hand you millions to grow in 18-24 months. You either make it happen and raise more money, or you crash and burn. I knew the math—she had nine months left. I told my friends who stayed, warned them, but they didn’t believe me. Not until more layoffs hit, one by one. Each call was the same: shocked voices on the other end, asking for references. I gave them gladly. Nine months later? Everyone was gone. They ran out of runway.

But hey, I did learn one thing from the adoption industry - adopt a better CEO.