Welcome to Ask Gorick Anything, Edition #47. This week's question is: “How do I decide whether to stay at or leave a startup that may or may not be going under?”
Keep reading to find out.
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ASK GORICK ANYTHING
“Stay or go at this startup?”
3 questions that can help you predict your company’s future (and yours).
THE QUESTION
“I've been at a startup company for about 5 years, which has been a truly great experience, except I'm getting more and more concerned about my future here and the company's future as a whole.
Our competition is heating up and everyone knows it, while our market share seems to be declining further and further each day there's no clear course of action yet from higher ups.
Maybe it is a tough patch or maybe not, but if not, then I know I need to bail or at least have an escape plan in place.
How do I accurately analyze this situation so I can make a realistic plan, especially if I'm happy where I am but concerned about stability that's out of my or my manager’s control?”
—Javier from Austin, TX
GORICK’S RESPONSE
Hi Javier,
You’re right to ask these questions, especially at a startup.
After all, you’re investing the next few years of your life into this startup—but don’t have the benefit of “diversification” as a venture capitalist (VC) does. (If a single company in a VC’s portfolio becomes the next Meta, they’re set, even if 99% of their other companies flop. You don’t have this luxury as an employee.)
So, how do you figure out if this is just a rough patch or if it’s downhill from here?
I’d ask myself 3 questions:
- What are the dynamics of my industry/market?
- What are the goals of my company’s leaders?
- Is my organization making smart bets?
Here’s what each question means in detail.
1. What are the dynamics of my industry/market?
Knowing what kind of industry/market you’re in can tell you a lot about what “game” you’re playing. It can also help you understand whether you’re on the right track as a company.
Markets can take 4 forms—from most to least “concentrated”:
1. Monopolistic—where you either own the entire market or very little because it costs a lot to build the product and incumbents benefit from network effects (defined here)
- E.g., Online search (e.g., Google), utility companies
2. Duopolistic—where the market is similar to a monopoly, but is competitive enough to support two massive players
- E.g., Rideshare (e.g., Uber and Lyft), credit card networks (e.g., Visa and Mastercard)
3. Oligopolistic—where it’s not impossible for someone new to join, but the “barriers to entry” are high enough that only a few big players will succeed
- E.g., Airlines (e.g., Delta, United, and American in the U.S.), wireless carriers (e.g., Verizon, T-Mobile, and AT&T)
4. Competitive—Where it’s easy enough to start a company, easy enough for customers to switch around, and big enough of a market that many companies can succeed if they conquer their own niche
- E.g., Restaurants, independent coffee shops, niche consulting firms
So, which “game” are you playing?
- The more you lean towards monopolistic, the more your declining market share will be a problem long-term.
- The more you lean towards competitive, the more room you’ll have to stay relevant even if you’re not the market leader.
2. What are the goals of my company’s leaders?
The better you understand what drives your company’s founders and leaders, the better an idea you’ll have of where they’re trying to take the company (not to mention your fate in this company).
Broadly speaking, founders’ goals fall under 3 categories—from most to least intense:
1. “The moonshot”—To build the biggest company possible
- E.g., To become the next Adobe
2. “The acquisition target”—To build a company that can be easily bought
- E.g., To get bought out by Adobe
3. “The lifestyle business”—To build a company that fits with their lifestyle
- E.g., To build a tool that coexists with Adobe and makes easy and steady money
So, do leadership’s motivations line up with your own?
- If you want to build a moonshot but you’re stuck building a lifestyle business, you’ll be unfulfilled.
- If you want to be in a lifestyle business but you’re stuck building a moonshot, you’ll get burned out.
3. Is my organization making smart bets?
In other words: Is your organization allocating its resources in the right ways (or at least in ways that you personally believe in)?
Bets fall under 3 categories (pulled from The Unspoken Rules, page 198, “Secrets to Getting Ahead”):
- What to start doing
- What to stop doing
- What to keep doing
If your company is starting lots of stuff and isn’t stopping enough stuff, it’ll soon lose focus.
If your company is stopping stuff and isn’t starting stuff, it’ll soon be gutted until there’s nothing left.
If your company keeps doing stuff and isn’t starting or stopping stuff, it’ll soon be outcompeted by someone else who is betting on the right things.
The bottom line?
To build a career you’ll be happy with, it’s not enough to simply think like an employee. You need to think like an investor. So, put your investor hat on, look at your situation, and see if it’s where you’d put more of your precious time!
See you next Tuesday for our next story and unspoken rule,
Gorick
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MORE OF MY WORK
1. Keynote speaking: My early 2026 speaking calendar is filling up! If your organization is looking for speakers for your internship program, new hire orientation, new student orientation, manager training, all-hands meetings, recruiting season, year-end performance evaluation season, or something else, let's chat!
2. How to Say It: Flashcards that teach you to know what to say in every high-stakes professional setting via hundreds of fill-in-the-blank scripts (just like the examples above). Free shipping on all orders over $40.
3. The Unspoken Rules: My Wall Street Journal Bestseller that Arianna Huffington calls “a blueprint for anyone starting their career, entering a new role, or wanting to get unstuck.” Used by top companies and MBA programs.
