46 Questions Every Tech Founder Should Ask Themselves


Follow this step-by-step questionaire to gain a deeper understanding of your startup:

1.   Clearly define your crazy idea that may have a significant chance of working.

2.  What type of company am I building? e. Is it an agency, SaaS, professional services?  This is an important question so you can understand the potential for an exit later on down the road.  If you’re looking for consistent cash flow to pay you for years to come then an agency model would be a good fit, but you won’t see the major multiples of revenue on an exit.

3.  Have there been any other exits in the industry?  If so how much and what is your differentiation/path to having a similar outcome.

4.  Who are the people on your team and what makes them great, and why are they so relevant to making your team great?

5.  Who is missing from your team today that you would want to have on your team in the future (think key roles, not necessarily names of people)?

6.  What are the key technology risks of your approach?

7.   What’s your plan for risk elimination at the lowest possible cost?

8.  What’s your plan to validate your hunches about the market that will help you decide what market segment you want to enter?


Problem overview

9.  What is the problem you are trying to solve?

Unfair advantage

10.  Do you have a scientific breakthrough, intellectual property, business-model innovation or a unique partnership?

11.  Why is now the right time?

12.  If your plan is successful, what economic or market benefit will the technology convey?  Address the innovation in significant detail—think science and engineering, not marketing. Explain the principles of the technology.

13. What, if anything, has been proven?

14.  How far is this from commercial scalability?

15.  What risks remain to be proven?

16.  What are the three major things that could go wrong?

17.  Have theoretical models been created or validated?

18.  What external third party has validated your models and experimental results?

19.  How long will it take to validate the viability of the technology, through experiments or otherwise?


20.  Who are you, and why are you qualified to lead this opportunity?

21.  What skills do you bring to this problem?

22.  What technical skills will your team need to add?

23.  Do you envision yourself as the long-term CEO or in another role?  The focus is mostly on you, your goals and your technical team. Address why you are uniquely qualified to solve this problem. People, who are key to your innovation, matter to your success.

24. What is the role of every member of your current team?

25.  Are they all working toward mitigating your primary risks, or are they working on non-critical development that can be addressed later?

26.  Are they the best possible people for meeting your current milestones?

27.  Are the founders thought leaders or associated with thought leaders in the field?

28.  What critical people, who could address your key risks, are missing, and where can you find them?


29.  What technical milestones will this financing help achieve? It is important to understand your path to mitigating the technical risks you face.

30.  What are your future milestones, and how much capital will you need to achieve each?

31.  What is the company status and burn rate at each of these milestones?

32.  What are your contingency plans if things don’t go well?

33.  Is the amount for which you’re looking in line with the risk-removal milestones you have outlined?

34.  What is your total and operating cash burn (the amount you’re spending) per month, in case months stretch into years?


35.  Do you have a good understanding of the competitive landscape? Explain how you do.

36.  Are you comparing your company against technology competition in areas that matter to the end customer?

37.  Are you comparing your future product to your competitor’s current product or to their future product?

38.  Is your innovation addressing a need in a large enough market (over a billion dollars)?

39.  How significant a step forward is represented by the technology or innovation?

40.  What impact will it have on the competition?

41.  Why can’t a competitor replicate your plan tomorrow?

42.  Why have other players in the field missed out on the technology?


“We project $XXXM in revenue in 2021.”   Your five-year marketing financials and revenue projections are a shot in the dark. All forecasts are wrong.

Instead, focus on your burn rate and your path toward achieving milestones rather than false precision at this stage.

“We expect to grow from 50M to 150M users in x-time frame.”

43.  How will you acquire your initial customers and how you keep them?   Plans often fail to explain how the founders will bootstrap themselves in startup mode.

44.  How will you get to a large customer base in the first few months or quarters? Details matter more than broad, unsupported assumptions. If you have indicators or solutions to the bootstrapping risk, that is important to us.

“I have the next Facebook / Google / Twitter.”

A better social network than Facebook is highly unlikely.  If your business plan is built on copying what existing companies are already doing, you are unlikely to succeed.

45.  Why you are the first in your field?

46.   Are you prepared to sell all of your assets and invest it all in this business?   Honestly, if you are not that truly convinced in the success of your business, then you may not have the right team or model.

But if you are indeed ready to go all-in, then throw the business plan out the window and get ready for trench warfare.

This list was in large part derived from the musings of billionaire Vinod Khosla and several other successful tech entrepreneurs.   I’ve found this exercise to be enormously helpful in analyzing potential startups I want to build and I hope you find it useful as well.