Why NO is the next best thing after YES

For some reason, folks in tech, particularly investors, have trouble saying NO.

Typically, the fear manifests itself in not even bothering to reply. After a number of seemingly positive interactions, the replies just stop.

Saying NO, whether to a potential investment, potential hire, current employee, or a family member or friend, is just basic respect and courage.

Saying NO, and briefly explaining why NOT, is the right thing to do.

Instead of pretending like NO will hurt the relationship, let’s face it—a direct NO actually creates clarity and respect, and improves our relationships with each other.

I just finished raising the next Techstars NYC fund. This fund is going to invest in the next four classes of Techstars NYC companies, starting with the Winter 2017 class.

The process only took me about a month. Of course I had an unfair advantage, because of the support of current LPs, and the strong reputation of our program.

Yet, during the brief period of time that I was out on the market fundraising, I was back in the founders’ shoes. I put together a few slides, got feedback from my mentors, created a pipeline of potential investors, and methodically reached out to new and existing prospective LPs.

What I appreciated the most during the process is when people gave me a quick (or not-so-quick) and clear NO.

“Sorry, Alex, not a fit right now because I don’t have the liquidity.”

“Sorry, Alex, my fund wouldn’t allow me to invest in another fund.”

“Sorry, Alex, we just bought a house and my money is tied up.”

“Sorry, Alex, I prefer to invest directly.”

I love getting a clear NO.

Don’t get me wrong, I love getting a YES a lot more, but NO is the best thing after YES.

The worst conversations are the ones that are a MAYBE. The worst conversations are the ones that hang in the air. The worst conversations go silent after a few follow ups.  The worst conversations start with strong momentum, then stall, and run out of air.

I can’t stand a MAYBE, and that’s why, if someone didn’t respond after two follow ups I moved them into a PASS category. I have strength and courage to face the reality—it is most likely a PASS.

When founders are fundraising they are full of hope, and pretend like NO is actually a MAYBE. Oh yeah, I am still talking to so-and-so, and while I’ve not heard back in a few weeks,  they’ve not said NO to me. Your gut knows it is a NO, but you pretend like it is a MAYBE.

Let’s stop pretending, and save ourselves time.

Instead of obsessing over a MAYBE, just move on. Start a bunch of new conversations. Fill up the top of the funnel. Talk to more and more people to maximize your chances. Be in control, and get to a YES.

The route to a YES is paved with many NOs.

Knowing that, and driving every single conversation to clarity, even if it is a NO, is how you can get the job done.

Now back to saying NO to others. Please do it. As a founder, you have an opportunity to start fixing this dysfunctional part of our tech culture. Don’t pass a MAYBE onto others.  Have the strength, courage, and respect to say NO, when the answer is really NO.


Fundraising Startup Advice Venture Capital

Alex Iskold View All →

Engineer, Immigrant. Vegan. 3x Founder, Managing Partner @2048vc. Previously ran @techstars in NYC. I write #startuphacks: http://alexiskold.net .

6 Comments Leave a comment

  1. Couldn’t agree more. Our first client went into a dead silence for a week and we had to reassure him that we are okay with a ‘no’, only then he said NO. That said, talking about this episode with sales gurus, we learnt that- had we keep his interest piqued and not let a week go by without talking, that MAYBE could have become a YES.

    Liked by 1 person

  2. Part of that “no-o-fobia” is because we are afraid to burn bridges. We want to leave ourselves a way back in had the situation turned out differently. That said, a clear No is indeed a sign of respect and frees up a ton of mental capacity for both sides. Neither party has to keep tabs on each other.


  3. As a start-up founder, I’ve come across some investors or potential mentors who’ve said they don’t have time right now but would like us to keep them updated on our progress. For the most part our team treats that as a polite ‘NO’. What’re your thoughts on this? Do these sort of investors turn around and come back?


    • Sure, but you have to make a lot of real progress and keep getting on their radar not just by following up with them yourself, but other people telling them about you.


    • Thanks Alex. So far our focus has been on introducing our product to customers and letting the product talk for itself. We have gained a decent amount of traction using that approach as our clients have started referring us to their partners which has started to generate a greater amount of interest with investors as well. We are hoping that through this approach we will generate enough interest to start getting more investor interest while continuing to raise our valuation so when we finally go and ask for investment, we are positioned properly.