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How to Avoid Joining an Early Startup Failure by Interviewing Like a Boss

Or fix the trajectory of your own doomed startup before it fails by asking the right questions…

Recently, I had the opportunity to discuss joining yet another early-stage startup as their first employee, go-to-guy and general, all-around ass-kicker. This is basically my favorite position. It’s brimming with chaos, research, process definition, leadership, team-building and all the other aspects of work that keep me excited.

The other thing it is, is totally, crazy risky. High equity, low salary and did I mention the chaos? Joining a team of less than 5 means you’re going to interface with your founders and fellow team members in acts of design, definition and the discovery of what this company is really all about.

What happens when it turns out you had vastly different positions on this industry, this product, your users or what your job is? The truth is, if it doesn’t come to light in the interview, you’re facing probably a 1–2 year commitment of you being unhappy, because sad to say, you’re probably not just going to walk out, despite anything you discover.

In order to mitigate this job risk, I’ve developed a series of questions that I ask companies during the interview process. In my own interviews, it’s fairly common that I ask twice the number of questions the interviewer asks me. The secret side-effect is that not only do you discover what you need to know to reduce your own risk, but your curiosity and commitment will actually likely increase the chance you’re going to get the gig.

So, here’s the (default) list I keep of things I want to know before joining an early-stage startup — or that I want early startups I join to work at being able to answer:

Customer Data

  • Why do people sign up for products like this (what’s their primary motivation?) Have you directly observed the reason users sign up for products like this?
  • What mechanisms are we putting in place into the product to capture customer data and reveal it to our team (data science)?


  • Who are our key competitors? First and foremost, do we agree on who they are — and are we honest about who they are and how good they are?
  • How big are our key competitors teams? Do we believe we can compete on their level with a smaller team, or that we really need to scale up to their operational size to really compete?
  • How can we track competitive activity and counter or improve upon? (i.e. Trends, new features, partnerships)
  • How many users do our key competitors have?


  • What can we fuck up and this will still be a success — i.e. where do we have the least risk?
  • What can we absolutely not fuck up, because doing so would spell doom for the venture? — i.e. where is our highest risk?
  • What are the organizational values, and how we think they might impact our day-to-day work environment?
  • What’s our first huge milestone after launch?
  • What does launch look like, and do we agree on what a launch means?


  • What is the minimum required team we’ll need in-place to build this product or to operationally run this product once launched?
  • How long before launch does an operational team need to be in place and not just a building team?
  • In recruitment, do we need specialists in certain areas, .i.e. content genre specialists, legal issues, etc. to pull this off? We should identify these unique needs early.
  • Do we have a formal group of advisors to assist in positioning and high-level opportunities?
  • Do we have a formal board or accountability structure to keep leaders accountable and as a resource for employees?


  • What’s our total runway? Our expectation of profitability in the first year? How much do we expect to spend on marketing?
  • How much do we have to allocate to team growth — equity, salary, etc.?
  • What is our relationship with current investment and responsibilities and expectations toward them?
  • What are our unit economics (or what might we need them to be for the venture to be profitable (i.e. acquisition cost per customer, customer lifetime value))?
  • What do we need to export or be able to track related to accounting and measurement of business financial metrics?


  • If we’ve already started developing the product, what technology stack is it currently being developed in and is that a suitable one for scale/growth?
  • Is it a technology stack that is especially easy or difficult to recruit in to?
  • Out of what we’ve created so far, do we have more than wireframes and actual code? Specifications? Feature documents? What are we creating that attributes to the posterity/learning of the product and features?
  • What are the various data tables and data for each? i.e. X user, X group, X product
  • What can we assume to expect to need in customer support and customer communication right out of the gate?
  • What integration points have we planned for and what do we know we’ll need (payments, analytics, stats, etc.)?
  • What are our requirements related to security? Do we have any security risks?
  • How are we logging activities and presenting those logs to assist with customer support?
  • What will the product need to support in emails (product, marketing, transactional) to communicate with users?
  • What is the financial situation of the economies we’re selling this product in (taxes, app-store economies, etc.)
  • Where do we draw the line with the proposed product so far? Is every feature absolutely required to launch? Do we have an MVP? Or, an idea of what’s nice-to-have?


  • What is our marketing strategy for launch? For on-going?
  • What are we expected to need in a marketing budget?
  • What will marketing need in analytics or administrative functions to determine their effectiveness?
  • What marketing opportunities exist that require budget versus those that don’t (what have we yet outlined as tactics that are growth hack-y versus large campaigns)?
  • What marketing-centric features (on-boarding, viral acquisition/social invites, drip campaigns) have we considered baking in to the product?


  • What are we worried about? What keeps us up at night?
  • What hard dates are we facing for product components/issues for the next year?
  • How are we going to organize/keep track/stay accountable for all of our timelines/needs (i.e. what tools are we going to use to get this company going)?
  • As founders/organizational leaders, what do you see (or what would you like) your day-to-day responsibilities to be?
  • What are aspects of your personalities as founder(s) that might make you difficult to work with on a company level? That will be things to overcome? Or, maybe better said, what are your quirks that we should be prepared to face as an organization? (examples being things like: I’m terrible at responding to emails. I’m always in convos with important people, so my schedule is crazy. I’m hard to reach. etc. etc.)

So, that seems like a lot of questions, right? Well, you probably won’t get to ask them all, to be honest. Aint nobody got the time for that. But, by asking the questions here that matter most to you, you’ll start to get a few things clear before joining an early company, a set of cofounders or a new team.

1. How do these people think and do I agree?
2. How much thought have they put in to all the aspects of successfully launching a product, and if they haven’t — am I comfortable with that, or that I might need lead to us in these directions?
3. Honestly, are they on the level?
4. Are they honest about the state of their current industry and its challenges?

The only sentiment I want to leave you with is this:

You might assume that joining a startup means you’re working with bad-ass Google types and high-performance killers, but the sad truth is that they’re often not nearly as high-performance as you think. You need to take the discovery of how effective your potential founders and early team might be in to your own hands, because a good idea won’t get you to the finish line — good teams get you to the finish line.

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