When Things Go Terribly Wrong

What to do when everything falls apart.

Apr 24, 2024

👋 Friends,

I’m currently in San Francisco and Menlo Park to host a 30-person founder dinner and a larger mixer. My first observation: there is an insanely high density of smart, accomplished in SF. It was fairly easy to fill a room with 30 entrepreneurs who meet a certain traction bar.

Tomorrow I’m in Seattle for the first time. Heard great things about this city and I’m excited to see what it’s about.

The past few months have been packed with travel (I’ve taken close to 30 flights in 6 months) and I’m excited to stay put in New York for most of summer. There is a lot of remarkable activity happening in NYC - many new companies built and new communities formed, and I’m looking forward to spending most of the spring and summer there.

I’m firm on my stance that New York City is the best place in the world to build a productive career and awesome life, and I’m willing to put my money where my mouth is and today I’m launching a new project with Rho:

ANNOUNCEMENT: We’re choosing five founders, creators, or entrepreneurs to fly in for Tech Week from June 3-9.

Your flights and hotel will be covered, you’ll get VIP access to my events, and you’ll get to hang with us.

Apply here.

I wrote today’s article immediately after the most stressful 72 hours of my career.

I was in Miami hosting a four-day event series at a private mansion as part of an ongoing series called Lumos House. It was our second time hosting the event, and things went terribly wrong. With $40,000 USD on the line and hundreds of people in attendance, we went through hell to avoid the worst-case scenario.

It was a humble reminder that things can be going well—but suddenly make a turn for the worse.

A short summary of what happened:

I hired an event vendor in Miami to host my four-day event: Lumos House
The vendor ended up being *really* shitty (…you have no idea)
They engaged in miscommunication, deception, lies, and gaslighting - the full nine yards
It resulted in me having to move my event FOUR TIMES to four different mansions, in four days
The final straw: me having to call an audible and find a new mansion, just an hour before the event
My partners and I invested ~$40,000 USD into this entire affair

So what do you do when things go terribly wrong?

What to do when everything falls apart

Throughout the entire affair — the team was surprisingly calm. Most of us are experienced operators, having worked an average of a decade in intense, high-pressure environments in the corporate world, but this was the first time our instincts were truly put to the test.

I’m proud of the work that our team did but wasn’t until a few days after the incident that I had the time to reflect on what had happened.

So this is my gift to you today: a guide on how to deal with a crisis… so hopefully when (if) you do go through one—you’ll know how to respond.

🫠 Right when the crisis occurs.

It’s normal to experience a myriad of emotions immediately following a crisis. You might understandably be fearful, angry or upset. This is when it’s important to pause, take a breath, and regulate your emotions to put yourself in the optimal state to solve the problem.

Impede strong negative emotions like anger, sadness, and fear. Your objective in the current moment is to make the most optimal decision given the circumstance you’re in. Strong negative (or even positive) emotions, like anger, are not productive for decision-making. Take a breath, and remain calm, grounded, and logical. It’s helpful to have your number 2 person remind you of this.
Delay counterproductive activities like venting, finger-pointing, and complaining. During a crisis, you need to save your most precious mental resources to make crucial decisions. Though venting and shouting someone’s face off can be therapeutic and might seem to be the right thing to do in the moment, try to delay the gratification of doing it and remain calm.
Maximize your access to useful information and data. While I was at Google and Facebook, we always used the same problem-solving framework. The first step was always to understand the state of the situation to help us understand what the “truths” were so we could operate from an objective point of view. From there, we’d evaluate all the feasible possibilities to solve the problem.
Minimize the number of decision-makers. While you want access to as much productive data as possible, you want to minimize the number of stakeholders in making the decision. More stakeholders mean more communication overhead, inefficiency, and potentially groupthink. Limit the decision to 1 or 3 people (keeping to odd numbers reduces the possibility of deadlock.)

🤯 To solve the crisis.

Ask yourself these questions to solve urgent problems in a logical and rational manner.

Problem Identification.
1. What is the immediate problem you have to solve?
2. What does it mean for the problem to be solved?
3. When do you have to solve it by?
Assessment.
1. What options should you consider that are within the realm of possibility?
2. What is the probability of success for each option?
3. What are your constraints and dependencies?
Decision.
1. What are the trade-offs for each decision?
2. What are the impacts?
3. What are the second-order effects you need to consider?
Action.
1. What should you do to maximize the probability of success for your chosen option?
2. What do you need to do to put the plan in motion?
3. How can you mitigate risks?

😮‍💨 After the crisis has occurred.

“Fool me once…”

To make sure you don’t make the same mistake again, do a proper retroactive assessment to understand what went wrong and how you can include preventative measures to avoid it.

I use Amazon’s Correction of Error mechanism (I write about it here.)

Here’s how it works:

Identify the cause
Evaluate business impact
Investigate the root cause of the problem
Initiate action items to fix the issue

Scenario: A digital marketing campaign failed to launch on time.
Issue: A digital marketing campaign for company XYZ wasn’t ready to launch on the proposed date of October 31st.
Impact: Missed incremental revenue opportunity of $100k from 2k new customers. Increased customer churn by 1.5% as a result.
Root Cause: Marketing materials and assets were not completed in time. This was caused by key team members being on vacation and not coordinating beforehand. The project leader did not have oversight over the roles and responsibilities of the team, and resourcing needs. The project leader was not sufficiently plugged into the workstream, which reveals a flaw in the operating model of the team.
Action items: Assess next best alternative on a proposed date for the marketing campaign. Remodel the new digital marketing budget to determine timing windows and alternative tactics. Conduct a retrospective on the team’s working model and create a proposal for a new operating structure.

For those of you who are entrepreneurs, executives or someone who operates in high-stakes environments, I hope this is helpful.

(And I hope you encounter as few crises as possible)

Let me know what you think in the comments below.

If you’d like to read about the full story, leave a reply and I’ll consider publishing it.

📌 Andrew’s Picks

Fascinating internet things I’ve come across…

Jim Carrey Speech at The Golden Globe 2016 – Something I keep watching over and over again. Beneath the humorous undertones, the message is clear: Nothing really matters. Or as Jim puts it: “If you blew up our solar system alone you wouldn’t be able to find us or any of human history…”
Storytelling – A short framework on how to tell great stories by Joe Previte.
The Rocket Ship Startup List: 2024 Edition – Jeff Bussgang is a long-time investor, senior lecturer at Harvard Business School, and General Partner at the fund I invest at. Every year, he publishes a list of startups that you should consider working for if you want to maximize long-term growth and compensation.

💃 Community Perks

🏨 Traveling for work? If you’re looking for a hotel with cozy rooms and social co-working areas, check out citizenM. I almost exclusively stay with them. They’ve even been kind enough to offer this community a discount. Reply here.
🚴 Discounted Equinox membership in NYC. Equinox is my second home. I recommend it. Reply here for a free trial and a discounted membership.
🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyer I worked with for my O1A visa.
🍽️ FREE FOOD! I found an app that gives you 30%+ off fancy restaurants in NYC. AND $50 off your bill every month, plus $25 when you sign up. Not sure how long the offer will last. Sign up here.
❤️ FOUNDERS NEED LOVE TOO. I partnered with Coffee Meets Bagel (the app for serious daters) to offer y’all a free 1-month trial of their premium product. Check it out here.
What other perks should I include? Let me know.

🖼️ Behind the Scenes

Meet Jacob, my new Chief of Staff.

A year ago, he attended one of my panels and approached me after to pitch me on working together.

I was cautious but offered him a few small projects to work on. Fast forward to today, Jacob has over-delivered on every aspect of our community building, sales, event production, and partnerships work.

He’s a crucial part of my team, helping me produce events and run 1,000-person tech networking events and hundred-person conferences in Miami, Austin, San Francisco, and

I like to think he’s got one of the most unique jobs a 23-year-old can have:

Host mansion parties in 5 cities across the US
Have breakfast and dinners with CEOs, investors, and founders of up-and-coming tech companies
Manage rooftop bars, clubs, and restaurants
Do research on interesting software and events businesses
Work with a product studio to build on consumer apps and productivity software
Scope opportunities for small ($100k - $1M/yr) businesses to build and incubate

Last week, it came full circle when he joined me on a panel at New York University - sharing his experience as a Chief of Staff with undergraduate students.

If you see him around, say hi. He’s a trailblazer and I have no doubt that he’ll be up to extraordinary things in a few years.

P.S. we’re recruiting two summer interns. If you’re interested, reply to this email with your Linkedin URL and two 100-word answers to:

What is the toughest problem you’ve solved?
Why do you want to work with us?

See you this summer.