Redeye VC

Josh Kopelman

Managing Director of First Round Capital.

espite being coastally challenged (currently living in Philadelphia), Josh has been an active entrepreneur and investor in the Internet industry since its commercialization. In 1992, while he was a student at the Wharton School of the University of Pennsylvania, Josh co-founded Infonautics Corporation – an Internet information company. In 1996, Infonautics went public on the NASDAQ stock exchange.

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I Don't Know...

Dontknow I don't know.

Why is it so hard for people (including both entrepreneurs and VCs) to say these three words?

This past week I had two distinctly different meetings with entrepreneurs.  They both were successful serial entrepreneurs.  Both were exceptionally smart.  Both had good ideas.

The first entrepreneur, however, thought that they were expected to know the answer to every question.  There wasn't a question I asked that he didn't have a definitive answer to.  He knew what their pricing model would be.  He knew why Google would never compete with them.  He knew what their consumer churn would be three years out (despite the fact that they hadn't launched yet).  Whenever I tried to discuss the different risks in the business, he told me why they didn't exist. 

The second entrepreneur, had a different approach.  He definitively stated answers when he had them, but when he didn't know he said so.  When asked about his pricing model, he said "well, we're considering a few different options depending on the outcome of some tests we're running..."  When asked about cost of customer acquisition, he said "well we don't know what our numbers will be...but here's our model based on other comparable companies."  When asked about risks, he identified several -- and then we discussed how to reduce/eliminate them.

I've come to believe that a key investment criteria is founder credibility.  And, I think the second entrepreneur was far more credible.  No one expects a pre-launch company to have all the answers.  (In fact, we get scared if you think you have them).  As I've previously discussed, rather than have an entrepreneur sell me on why they are 100% correct, I'd much rather understand how they are attacking the different risks facing the business.

And, by the way, the same applies for venture capitalists.  I often feel that during company pitches -- and board of directors meetings -- we're expected to have an immediate opinion.  Should we double our marketing budget?  Should I hire this person?  Will this strategy work?  While it's OK to offer opinions and thoughts, I think it is also appropriate to acknowledge uncertainty.   

Why do people feel pressure to have an answer for every answer?

I don't know...



Many believe that appearing to not know represents weakness - the rest genuinely believe they know the answer.
A number of studies show that what people are often most wrong about is just how wrong they likely are. And most founders are usually pretty confident in themselves (or at least publicly appear so) - which leads to a bias in overconfident or overcompensating interviewees.


Ignorance is too often confused with stupidity. We are all ignorant about many things, no matter how knowledgeable we are on other topics. Too say "I don't know" is to confess your humanity. Ignorance is curable, but not if you deny its existence. I'm much more comfortable with people who aren't afraid to say "I don't know" when they honestly don't.

Mark Evans

I spent many years as a tech journalist asking questions, and "I don't know" was not something I came across too often - probably because few people want to be seen as being out of the loop, ill informed, etc.

Glenn Fleishman

Like Mark, I'm a tech journalist, and I've interviewed maybe several hundred executives at companies, from Larry Page when he was wet behind his ears to the current CEOs of tiny (but clever) firms, to EVPs at multinationals. And I have to say that anyone who can answer every question definitively, and, often, as soon as I hit the question mark, makes me nervous. The people I trust when I interview have definitive answers to stuff they know, and will talk around stuff they don't -- without speculating.

John Furrier

Great post Josh. Credibility is the key.

One point in your post that is worth highlighting is how the second enterpreneur views the market. He looks at the market as a fluid dynamic - "running tests" with "base assumptions". Many entrepreneurs have been scorned for this view (myself included) in being "not focused". I hate that word. All early stage entrepreneurs are 'very focused' on the fluid market how to enter and plans based upon certain market conditions or scenarios. Key is the focus on the possible scenarios - for that there is no one answer.

Your last point is importan: VC Credibility - When VCs sit on 9 boards and shows up once a qtr for board meetings with 'the answers' then their credibility is on the line.

Early stage is about entering the market with a narrow value proposition that has the opportunity to take advantage of a massive growth trend when in market. For this the entry strategy should be very clear and the answers to the so called 'billion dollar' revenue plan should be scenario based.

Keith Teare

Of course you realize that every person who pitched you this week is now anxiously recalling their meeting and asking the question, am I one of these guys?


Srini Kumar

I think a good business plan should read like science fiction. A lot of ideas I first read about in science fiction later came through in the end. I like Heinlein, Asimov, PKD, and Ursula K LeGuin. The sociological stuff. That's how our business plan reads, and that is the substance of OUR pitch.

My take is that business pitching is storytelling mashed up with a football playbook. I'm really not sure where "I don't know" fits in that framework (maybe "topics to research"?). It really should be incumbent upon the pitcher to suspend the disbelief of the audience. Maybe one big honkin' "I don't know" slide to kick the PPT off.

Does vision means fiction means lies? I think Steve Jobs got a lot of that during his career, don't you?

srini kumar


I see your point but on the other hand I have met some guys who were so undecided... They didn't know anything.

I believe that in a start-up you are also looking for the action-men type. As long it is more like James Bond than Rambo!

Yossi Gliksman

Ego that overshadows rationale and leads to disconnect from reality.

Peter Rip


Allow me to elaborate on your basic point just a bit. When I meet with pre- Series A entrepreneurs, I tend to focus on the quality of the thinking, not the validity of their conclusions. When an entrepreneur says "I don't know," what I listen for is their approach to how they would *find out*. After all, admitting you don't have all the answers is better than than thinking you do, but it is even better to demonstrate how you would go about determining the answers. That thought process of (1) recognizing limitations and (2) analytically overcoming them, is ultimately what a VC is really investing in.


Once you start applying the scientific method to building companies and think of a startup as a set of hypotheses, "I don't know" becomes the answer for everything that hasn't happened already.

Shan Sinha


Great post. I'd go one step further and add that saying "I don't know" demonstrates that much more confidence, whether coming from the VC or the entrepreneur.

Coming from the entrepreneur side of the fence, what would be interesting to hear for you would be the more effective "I don't know but here's how we would do it" to various questions that come up in a pitch meeting.

- Shan

David Dalka

One of your best posts ever - and that is saying alot.

Form my early days at BlackRock I was always trained to be transparent about the things I don't know - mostly because someone could make a multi-million dollar decision seconds later off of that input on a major trade.

The venture capital world is no different, it's just that the results of an error in inputs don't become transparent as quickly.

I, like you, would much rather conduct business with someone who is not afraid of these words...

Christopher Mancini

I am really glad I found this blog. It is refreshing to see someone in your position share your thoughts, musings and frustrations with your experiences. I have never been before a VC, but I wish to be soon. Being able to read through your posts of experiences that were poor and ones that were perfect helps me prepare and improve my skills so that when I do get the opportunity to present my property management application startup, I am successful.


alan levy

Great Post. Things are moving so fast and barriers to entry are so low that it's virtually impossible for an entrepreneur to NOT say those three words.
If you have developed a useful application that would be hard to replicate by Google or anyone else AND it has a viable revenue model than those three words are not needed to answer those two questions. If that is not the the case than I suggest you revisit your initial plan.

CEO and Janitor


I think this boils down more to a difference in personality between the 2 entrepreneurs, as the first one would qualify more as the Alpha kind. Some people prefer the swagger and confidence of this type of person in meetings or presentations.


I expect they're playing to their audience.

Just as you've seen two types of entrepreneur, I've encountered two types of VCs through the funding process: those who reward and understand this type of honesty and those who punish it. Based on the small sample size we dealt with, the latter were far more prevalent.

Our supposition was that they were looking for a pre-packaged, no-risk story that they could take to an investment committee. Then, if the entrepreneur "missed the numbers", it could be written off as bad execution.


Great post again! Some VCs don't like these three words. I don't know!


The "I don't know" question/answer series seems to fit within a zero sum game ... sometimes. When an investor asks a question he typically wants a good thought out answer, but only if it is a common question (ie. customer acquisition costs, competitors, etc). The problem is that as a good investor I want my entrepreneurs to have already thought through the common questions as well as the uncommon ones. So the entrepreneurs that say “I don’t know” are automatically put in the “why don’t you know” category … Investor: 1, Entrepreneur: 0

The only good answer should be what Yossi and Glenn stated above: “we’ve researched this question and although currently there is no definitive answer, here are the steps/tests we will be doing to make the best decisions.” A good entrepreneur should have these answers in his back pocked for most questions.

On the other hand, I want my investors to make me think differently and see things from a unique point of view, and not just a skeptical pedestal. So if I’m talking with an investor and he doesn’t pose a question that makes me think differently, and go “I don’t know … I’ll get back to you,” then I’m unimpressed with the investor and should probably move on since there are hundreds of look-a-like deals and this investor was not intrigued enough to think differently … Investor: 0, Entrepreneur: 1

So it seems that investors should make their entrepreneurs think, and entrepreneurs should have already thought

Steven Cardinale


IT's because we've been judged all our life to give an answer. "I don't know" is never an acceptable answer to school exams, police officers, angry parents, priests, and especially job interviews at technical places. And this is to further into human ego.


It's called a 'deficit'. Regardless of any attempt at presumptive early experience or other drivers external to the person; we're expected to 'grow and mature' beyond such tendencies. It goes beyond personality or unique style. This one is clearly a sign of arrested development in a key area associated with integrity. That we succeed in spite of certain deficits is clear and this is one more example. However, it's one that would give me pause.


"I don't know", but I think that Josh has brought up a bigger question than whether entrepreneurs should, or should not have all the answers.

The question I think he is really talking about is how should you act, whether entrepreneur or VC. I say this, because it applies to how your presentations look to investors and other entrepreneurs, the way you dress, the team you chose, and just about anything else related to raising capital: It depends on the audience, the timing, your performance, and so many other dynamics, like the ambiance between you and your listeners.

Just the other day I showed my presentation to one investor who thought it was incredible, and loved the simplicity in the way I introduce the opportunity. Then, I spoke with a business school alumni, who is also a VC, and they said that they seemed like they were too raw and needed more content.

My point is that there are so many variables that make someone or something be perceived as great, but it was only for that moment, that specific audience, that time of day when they'd just had their coffee and were ready to feel good about anything, or that investor who seemed to want you to know every answer, even if its a misinterpretation.

I'll end by saying that there are some major actions that can damage categories that can be established to increase the chances of your success on average, such as the above article's "try not to act like you know it all", or don't introduce yourself with a 500 page manuscript. Once that's out of the way, I'd focus on who is my audience and what are they looking for, what will be my surroundings or medium of communication, how am I performing today, etc...

Those are the differences that will improve your batting average the most I think.

Eric Krock

This is absolutely correct. I made the same point during my SVPMA presentation on product management last year, actually: I use the phrase "I don't know" whenever it's the truth in sales, marketing, and product management and it does wonders for clear communication and building your credibility. If you try to pretend you have answers to questions when you don't, you're being unethical, sooner or later you'll get tripped up, and people will lose trust for you. Plus, you seem no different from all the glib, overconfident know-it-alls in the Valley. But if you simply acknowledge it when you don't know the answer to a question, you display the self-confidence to acknowledge you don't know it all and by so doing differentiate yourself from the glib know-it-alls. Also, anyone who has heard you say "I don't know" will conclude "This person tells me when they don't know, so if they tell me something, they must really know the answer." There's nothing more dangerous than a person who claims to know everything. It's bad enough if they know they don't and are just lying; it's worse if they don't realize the limits of their own knowledge. If you don't know, just say so! Everyone else realizes you're not omniscient; there's no harm in confirming it. Of course, you should have done your homework in advance so this isn't a common situtation and tell them what you've done to investigate the question and how you'd go further, but whatever you do, don't be deceptive. Just be honest!

Anthony Kuhn


I think there is generally too much swaggering and corksuredness in business and it's refreshing to see you recognize the value in honesty and humility. When these traits are combined with intelligence and energy, they can open almost any business door! I linked to your post in my blog entry today at the Innovators-Network so others can share in your kind insights with regards to pitching and startups. I'll be looking forward to more posts on healthy living, startup-style!

Salman FF

Charlie Munger (Warren Buffet's partner) calls it: "Doubt-Avoidance Tendency", via a great post by Marc Adreessen:
it's a good read.

Raza Imam

Didn't Socrates say that the only true wisdom is in knowing you know nothing?

Avoid slicksters and fast talkers.

Raza Imam

Kent Goldman

Today, the Freakonomics blog on the NY Times has a great Q&A with Bill James - the world's leading baseball statistician. In many repects, what his most striking about the interview is James' willingness to admit what he doesn't know. Undoubtedly, this helps him to better frame his future studies. Here's an excerpt:

Q: Has sabermetrics pretty much squeezed the last drop of new insights out of traditional counting statistics? If so, what data ought to be collected to improve our understanding of the game? If not, where can the boundaries be pushed?

A: We haven’t figured out anything yet. A hundred years from now, we won’t have begun to have the game figured out.

Q: Is clutch hitting a repeatable/retain-able skill?

A: I don’t know.

Rob Sandie

I remember overhearing a VC say "They were doing great till they couldn't answer a question".... and that was a graduate school Business Plan competition!

VC's can be sharks and the pressure is on for us Entrepreneurs to know our business better then anyone else.

That being said, saying something stupid is worst then saying "I don't know".

joe g

hmm, can't say i've ever had this problem.

I know everything. :)

lois Hoffman

I don't know how to answer your question to verify my E-mail address


Its interesting reading what the VC community discuss about the online communities. I think this recent move from FB shows that the original developers are still involved.


Its interesting reading what the VC community discuss about the online communities. I think this recent move from FB shows that the original developers are still involved.


Its interesting reading what the VC community discuss about the online communities. I think this recent move from FB shows that the original developers are still involved.


Great post. I wrote about "I don't know" recently as well. Entrepreneurs try to gain confidence by getting answers, what they don't realize is that you can attain more confidence if you start seeking answers by first acknowledging "I don't know."

Read more here:

Stephen Sprouse

Great post. I'd go one step further and add that saying "I don't know" demonstrates that much more confidence, whether coming from the VC or the entrepreneur.

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