For those of you who have missed these essays for a few weeks, please know that family health issues have taken priority. All is well now. I have written often in this forum that time is the one thing no one can recover, and when your time is unexpectedly taken away from you, it’s a stark reminder of that.

It happens that I have recently seen a number of canned questionnaires about evaluating startup investment opportunities. All are heavily quantitative and written from the viewpoint of an investor looking for a venture return. They serve that purpose well. However, there are many tech startups that may have no need to raise external capital, that are designed by savvy operators just planning to make a good living by filling a customer need, and that are created with no preconceived exit strategy. You may have reason to join such a team or to do business with it. You may not have the right to do a due diligence inspection of the numbers. But, you do want to make a sound decision about whether this is where your precious time and attention are best applied.

To that end, I offer here ten lines of questioning that you can address in a straightforward interview. Complement these with some external references, and you’ll have a good basis for your decision. I can cite examples of startups that have flunked some, or all, of the questions in this essay, but they’re in my witness protection program. If you think nobody would be that misguided, think again.

  1. Is it a business?

Has the founding team come up with a plan to create a scalable business, including consideration of all the operational and financial details, as opposed to just a product idea? Do they speak the language of startup business building? Is there a business mind in a leadership role? Does the core team understand its own business model? Can they explain it succinctly?

  1. Is the business objective worth the time and effort?

Small opportunities can be just as consuming as large ones and waste valuable years of everyone’s time. Those generally fall into the category of “startup theater.” Can this business get to at least seven figures of predictable annual revenue in two or three years? Does it have a funding model that matches its ambitions? Exactly how is the start going to get started?

  1. Does the team have the right attributes?

Does the founding team have a history of working together? Do they have a following? Are they known by important people in their target market (as opposed just to knowing people). Is the organization clearly delineated? Are the relative equity/cash comp plans fair to all? Is there a nepotism problem, including even an over-weighted angel investor who is a family member of one founder? Are they all on the same page with respect to the priorities of the company?

  1. Is the team aware?

All too often teams come up with great ideas and fail to really appreciate the competition. They may not even view the status quo as a competitive threat. They produce a fabulous deck or website describing an idea that we have seen dozens or hundreds of times already. Have they done enough customer discovery to validate that others absolutely must have a taste of their Kool Aid and that no one else offers a substitute? Do they really understand pricing in their target market, and have they modeled the business accordingly?

5. Are their initial investors aware?

If any money has been raised, has it been done according to the rules so as not to poison future offerings? Does the initial investor group have experience in angel investing and know what to expect? Do they add value in terms of revenue opportunities and other connections? Which team members hold the investor relationships? Are there more where the initial batch came from? Is the structure designed for an orderly progression through subsequent funding rounds, if needed? Do the investors appreciate the need to preserve founders equity to keep those founders motivated? Are these investors truly passive unless called upon, or do they have a penchant to interfere?

  1. Are you a good match for this business?

What incremental value do you personally bring to the enterprise? Are you good at the skills or services it needs. Can you “get along” with the client? Does the leadership follow general business practices and understand the give-and-take of the marketplace? Do they pay their bills? Are they rational actors focused on operational success and not on an impractical quest?

  1. What is a realistic expectation for this company?

A pure service business that is well run may have no appeal to investors and no high-multiple exit potential, but it might be a great opportunity for you over the long term. You’re looking for the one in ten companies that can emerge from a pack of startups and achieve a level of stability and predictability and allow you to grow along with it.

  1. What’s missing for scale?

Is there a repeatable, turn-the-crank marketing and operational plan? Can each month’s progress compound on the month before? Do the founders have enough experience and industry inside knowledge to capture their fair share of the market? Do they exhibit the ability to anticipate and avert competitive threats? Are they circulating in their target industry where they are likely to find partners, customers, and key employees and to get advance warning of technology shifts?

  1. Is the company based on a “got to have” or “nice to have” concept?

As Flashpoint puts it, “authentic demand” is when you “can’t not want the product being offered.” Is it fair to say they the business can’t not want what you personally bring to the table? Will you be a key part of its success, whether as an employee, vendor, or customer?

  1. Would you recommend the company to your best friends, and would it enhance your own reputation?

Can you come to believe in the team and the business to the extent you are proud to be associated with them? Do you think they will lead you to the next quality step in career? Will your family be happy with your participation? A venture firm can easily and cruelly decide to ride its winners and ignore its losers. However, once you’re in with a company, you’re in. Your personal relationships become enmeshed in the business, and you can’t just walk out the door and leave them hanging. Down the road there will be that next opportunity where you want to be fondly remembered and given another spin of the wheel.


Don’t be bashful about asking interview questions along these lines. If you’re been around the block once or twice, you will recognize patterns that encourage you or warn you. You don’t need to fire up a spreadsheet, just immerse yourself in a conversation that reveals what’s important to your success.