50 Questions Founders Should Ask Themselves About Investors

I have received investment in my business from top tier VCs and investors.

I have narrowly avoided taking investment from the wrong investors.

Now, I’m the CEO of a profitable and rapidly growing company.

I could not have achieved this if I didn’t pause and start to ask myself and potential investors better questions.

So if you’re thinking about taking investment from investors…

STOP!

Before you do, I implore you to think deeply and create a list of questions to think about. The questions that follow aren’t necessarily for you to ask your investors, they’re designed for you to think about, and to help guide you as you select what investors you want to work with.

That simple act can save you years or decades of confusion and pain.

And the right investors that you need… Those dream investors who can help you succeed…

They will thank you for asking better questions.

These questions have helped me slow down and think more clearly. It’s my hope that at least one of these questions will help spark an insight or realization that helps you find the perfect investor(s), avoid the wrong one(s), and achieve massive success in business and life.

Before we dive in, let me explain how we developed this list. The foundation of this article was developed from years of being and living amongst founders and investors in Silicon Valley.

As part of our research, we spent a week working with Founder Institute.

The Founder Institute helps tech entrepreneurs build a business and raise funding with the help of experienced startup mentors, advisors, and investors. They have chapters across 180+ cities and 6 continents. You can learn more about their pre-seed startup accelerator here.

During our time collaborating with their team, we had the opportunity to interview and chat with hundreds of successful founders, mentors, and investors. It is through these discussions, our own research, and years of personal experience that we compiled this list.

And now, 50 Questions Founders Should Ask Themselves About Investors.

1) Why are they doing VC instead of building another company? (Supposedly Jeff Bezos asked Marc Andreessen and Ben Horowitz this when they asked him to be an LP at Andreessen Horowitz)

2) When decisions or companies have they backed that are truly doing good in the world?

3) As F. Scott Fitzgerald says, “The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.” Can they do that?

4) The best founders and investors can be quirky, but also effective. Do the investors you want to work with embody this originality and quirkiness? And are they effective?

5) Why are you excited about working with these specific investors for the next 5–15 years?

6) Are you prepared to get to know who this investor is by having multiple conversations and hangouts with them? Are you excited when you get to hang out or spend time with them?

7) How will their expertise, knowledge, and connections specifically help you and the company?

8) What are their goals (business model) and how will your expertise, knowledge, and business specifically and strategically help them achieve their goals?

9) Could you take feedback from this person that is extremely honest, critical, and blunt (while still respecting them)?

10) Have they built and sold a company?

11) Was that company or outcome something you admire, and will the domain knowledge they gained in the process be complementary with what you’re trying to build?

12) What evidence is there that they are willing to bet on who you are (and are becoming) as a person? In other words, are they confident that no matter what happens with the business, you will be able to figure it out?

13) Are they fundamental or dogmatic in their thinking? Or can they, and do they, regularly change or adjust their beliefs?

14) What personal belief have they changed in the last year or so, and why?

15) What’s the most valuable thing they’ve learned in the last year?

16) The now classic, “what important truth do [they] believe that few people would agree with them on?”

17) Who are there mentors? Who do they learn from?

18) Have they had a job or time in their life where they were humbled? What evidence is there that they can check their ego, roll up their sleeves, and chop wood and carry water?

19) What type of questions do they ask you? Are they asking what your childhood was like (a first principles approach to discovering who you are), or are they only focused on the present and what you’re currently making?

20) What proof or evidence have they given that they thoughtfully read through your deck, or are listening to what you’re saying? Plenty of investors haven’t set up proper filters or systems and get mired in a deluge of inbound. Because of this, they have a tendency not to listen on the phone or read the decks or emails you send.

21) Do they take care of themselves physically and mentally?

22) What addictions do you suspect they have and do they have a substance abuse problem? (I’m serious here- plenty of investors have more than one skeleton in the closet, and even something small like a daily overdose of sugar or caffeine can signify they’ll never be able to lend cognitive capacities to you that aren’t befuddled by adrenaline or a sugar crash.)

23) Do they want to back founders like you? Sadly, there are still many investors who actively look for founders who are borderline psychopaths that will do anything to “win”. What type of founder do they back?

24) Have they had a successful long term romantic relationship in their life? This is one of the most undervalued tells to discover what people are really like, and how well they collaborate with others.

25) Do they respect you? Do you respect and want to learn from them?

26) What portfolio investments have they been the first or lead investor in? Do they have a track record that shows courage and conviction? Are they lemming-like? Do they spray and pray, or do they back the truck up when they have conviction?

27) Have they had an exit that was more than an aqui-hire?

28) What type of compensation structure is their firm rumored to follow? Are they choosing a lower salary in exchange for a larger upside or carry?

29) Who are their LPs, and are you excited about making these people or institutions more money? If you can’t find that information, do research, or ask them. Understand if they can’t disclose all of them, but you should at least be able to turn up a few. Do you want to work your butt off to generate returns for these LPs?

30) What are the economics of the potential investment they would be making in your company, and what result do you need to generate to make it a success? For example. If they’re investing out of a $1.3B fund, do you have a coherent answer for how the piece of your business that they would own will grow to be worth $5B+ within the timeline they need to return capital to LPs?

31) What is their response when you explain to them how you’ll reach your first hundred million or billion in revenue?

32) How well are their other investments in their current or previous fund performing? Are there past or present funds up by an incredible multiple (say, ~7.7x times) that’s better than industry averages? You should want to be on a winning team just as much as they do.

33) How much do they usually invest, and who else do you have to bring into the round to make it easy for them to say yes?

34) What percentage of the companies they back go on to raise subsequent funding rounds, exit, or IPO? Are they known for making (or being willing to make) extremely large follow on investments in their winners?

35) Do they have investments in portfolio companies that are working on big challenges (AI, human augmentation, preventing war, fighting cancer, education, space, hard science, etc…). Or do they have a lot of vanity investments in Series D rounds of popular unicorns?

36) Ask people they’ve worked with how this particular investor balances helping when needed and leaving the entrepreneur alone when it’s not.

37) What is the philosophy of their boss and the firm they work for? Do their philosophical beliefs and actions align with your own?

38) Do they ever express any of their personal philosophies publicly, especially if it’s different from that of their boss?

39) Reference Check: Connect with 3 founders of successful companies they’ve invested in, and get their take on the investor.

40) Reference Check: Connect with 3 founders of companies they’ve invested in that have failed, and get their take on the investor. Bonus points if you do a reference check on the individual founders who failed (it’s easy to blame your investors for what you failed to do).

41) Do their portfolio companies inspire and intimidate you (in a good way)? Are they important for humanity and society? Or, are most of their investments in things to just amuse humanity to death on the way to extinction?

42) Do they spot serious challenges, opportunities, and perspectives about your business that you haven’t thought about?

43) What are some of their daily habits and rituals?

44) Do they use buzzwords and phrases or substantive ones?

45) Wise men have said that “the world is made of language.” Several of the best investors in the world have started to hint that they are only looking for founders who speak indefinite future tense about what they will accomplish. What type of language does the investor you’re pursuing use? Do they make vague, indefinite comments? Or do they make definite, strong statements? Can they speak about your business indefinite future tense along with you?

46) Are they willing to trust or defer to your expertise or analysis of a market? Or, do they want a scientific study done by ‘experts’ about each observation, metric, theory, or insight you’ve discovered or generated? The devil’s advocate can be helpful if he wields logic and data, but if they can’t handle being proven wrong by you… you might want to run!

47) What type of people do they want to invest in and why?

48) What do they prioritize when investing: markets, tech, ideas, or people?

49) Are they willing to get to know you well enough to gain enough context to invest in you as a person, or make the necessary effort to do (smart) character and reference checks on you? If not, how can you ever develop a positive working relationship or friendship with them?

50) Who are the five people they seem to spend the most time with? They’re becoming like those they spend time with — just like you…

Thanks for reading! If you enjoyed this article, please share it with a founder who is thinking about taking on investors.