Tips for Entrepreneurs No VC Will Tell You: Stop Nodding, You’re Killing Your Company.

When entrepreneurs go from Seed to Growth Stage

Work Session with Krishna K. Gupta, General Partner at Romulus Capital

Come talk with me on @JoeyJinKim where I converse with techies, founders, investors, and everyone in between.

As an investor, I don’t create anything. I don’t provide goods or services. I sit around, talk to people smarter than me, and make decisions to invest in a given company.

Decisions. That’s my only product.

In fact, if you’re a founder, that’s eventually going to be your only product too. Founders graduate from the “builder” phase (Seed) to “manager” (Series A) to “decision-maker” (Later Stage) whether you like it or not.

But when your end product is a decision, how do you build a superior product?

Software? Add more features. Hardware? Reduce the costs of parts. In decision-making, the only real meaningful avenue to a superior product is stress-testing the robustness of your product through disagreeing.

Disagreeing exposes the points of failure in your decision-making. Your C-suite and Board should fill this role. All this is obvious. Material from corporate leadership training.

Yet, disagreeing is unnatural to most of us. I know it wasn’t to me and still isn’t.

In social settings, disagreements mean stilted conversations and difficult dinner guests. In school, we match our answer to the answer in the back of the book, not challenge it. In MBA programs, we’re taught the “yes, and-” mentality where you first agree with the other person before building your own agenda on top of it.

But if you’re an entrepreneur at the executive level or an investor, you need to put a stop to this mentality right now. You are responsible for your product. If you’re a C-suite, your product in your company is decision-making. And simply agreeing with your C-suite suite or Board Members is leading to a weaker product.


If you’re like me and have been conditioned to “agree first, think later” in almost every social situation so far in life, there are systematic changes you and I should implement:

1. Stop operating on an opt-out implicit approval model.

Implicit approval includes small acts like nodding, putting in fillers like “definitely” or “mhmm” in conversations, and implicitly agreeing through silence. The problem with implicit approval is that they become habits. Start nodding at the beginning of sentence and you’ll find that you’re still nodding by the end of it.

The worst version of implicit approval is the opt-out version. Stop handing out your agreement with an idea so freely. It cheapens the value of your approval. It exposes you as a lazy listener who is not critically analyzing what’s being said.

Agreeing with an idea is not something to be opted out of — only something that we opt into. We should only agree if we mean to agree.

This systematically raises the level of discipline and quality of our decisions.

2. Lead sentences with matter-of-fact disagreements.

Begin with “I actually don’t agree with your analysis.”

Follow up with the reason. “The data doesn’t support it.” Or “The case example of X doesn’t support it.”

No emotionally charged words. Just factual, unapologetic agree or disagree.

I find that the sentence of explicit disagreements are the toughest to spit out. When I start out in any other way, it becomes an uphill battle — a long prose of apologetic justification leading up to the conclusion…only to find that once I reach the conclusion, I’ve lost my courage to say those words of disagreement.

By saying the most difficult sentence as the lead-off opener in a succinct way, I find that the rest of my articulation of why I disagree becomes an explanation rather than a justification.

Stating authentically what I’m skeptical of is something I’ve been increasingly trying to do during the first conversations with entrepreneurs. Weak founders get defensive, but for strong founders, it leads to more enriching conversations.

3. Join a “study group” that feeds you disparate sources information.

Every May, I find myself in a room with the richest people I know during our annual investor summit. Here’s what I observed:

At the highest level, the top players are forming what are essentially informal study groups to learn from each other. They have different names for it — board of directors, dinner parties, catch-up over coffee, but they are essentially study groups to get the pack smarter against the crowd.

But my hypothesis is that best players belong to numerous “study groups”. Like a Venn Diagram with many overlapping circles, you’ll have different and at times conflicting information, which empowers you to disagree.

Trying to practice what I preach, I’ve been putting together my own “study group” where I can share every week information in an e-mail thread what I’m seeing from different CEOs. If you’d like, you can join for this week’s discussion:


Once we stop automatically nodding to people’s ideas as the default setting, our agreeing start to mean something.

Through thoughtful scarcity of our affirmation of others’ ideas, others come to recognize that our agreeing with their ideas implies we listened critically to what they were saying. And once we do agree, we are signaling sincere agreement.

More importantly, we ourselves come to see our own agreement as an affirmation of our own conviction. We become more sure in our decision-making.

If you consider yourself a decision-maker and most certainly if you’re a founder of a startup, your role in the company means you carry not the privilege but the obligation to disagree.

It’s the only way to deliver on the best version of the only product you’ve promised to deliver.

I mean, you’d agree, right?