This newsletter is not yet good

The benefits of proactively seeking negative feedback to remain intellectually honest

This week's post is about intellectual honesty and proactively seeking constructive feedback, so if you can spare a few minutes this week, I would appreciate it if you could complete this 5-minute survey and provide feedback on this newsletter.


  • I’ve received positive feedback about this newsletter, but if it were really good, it would be taking off. The fact that it hasn’t taken off shows that there are a lot of opportunities for improvement.

  • To remain intellectually honest when receiving positive feedback, we need to go beyond the positive feedback and proactively seek negative feedback that deliver hard truths (something I’m working on with this newsletter).

  • One tactic is to having people you trust who are willing to deliver hard truths when I ask for feedback. They can be relied on for constructive feedback without consideration of your feelings and can deliver it quickly, creating a tight feedback loop.

  • Another tactic is to proactively seeking and encouraging constructive feedback from others, like by creating surveys which explicitly normalize and encourage negative feedback, or by following up with people who provide positive feedback and ask them explicitly for something constructive.

  • Getting our asses kicked with negative feedback is an inevitable part of the entrepreneurial journey. It’s better to seek out our own ass-kickings than to get blindsided by them.

  • Negative feedback exists – it’s just a question of whether we know what it is or if we’re choosing ignorant bliss.

  • Read on for some screenshots of conversations of me being humbled!

This newsletter is not yet good

Since I started this newsletter, I've received a lot of positive feedback. Some people I know (and some I don't) have reached out to me telling me that they found posts to have a unique, fresh perspective that is helping them. I've found that posts have been shared in private Whatsapp groups, and founders have shared posts with their teams and changed they way they measure progress with their startup.

But the truth is if it were really good, it would be growing a lot faster than it is. There are far more things I could be improving about this newsletter than things that are good. Buying into positive feedback too much can erode intellectual honesty, a concept I wrote about a few weeks ago:

Conviction is a trait that most entrepreneurs come by easily. It helps entrepreneurs overcome the inertia of starting to build things. But getting started is a small part of the journey. If building an entrepreneurial career (or building a startup) were a rocket ship, then conviction would be boosters, and intellectual honesty would be the controls. You need both to make it to space.

Intellectual honesty is the practice of seeking the truth – regardless of if it aligns with your personal beliefs or that you want to be true.

When I started my first startup, I mostly wanted to hear things that confirmed my firmly-held beliefs that we’d be successful, and avoided spending too much mental energy on anything that would prove those beliefs wrong.

The more positive feedback we receive, the harder it is to remain intellectually honest. We start hearing what we want to hear, and stop proactively seeking the truths that we may not want to hear.

With this newsletter, I'm being vigilant about intellectual honesty and constantly seeking hard truths. It's helping me consistently improve it in the pursuit of making it actually good. The two tactics I've been leaning into are (1) having people I trust who are willing to give me hard truths when I ask for feedback, and (2) proactively seeking and encouraging constructive feedback from others.

Having people I trust who are willing to give me hard truths when asked

Most people will not give negative honest feedback for fear of damaging a relationship. And even if someone is willing to give negative feedback, you may not listen to them if you don't respect their opinion! I had plenty of people who gave me negative feedback with my first startup, but they weren’t people who I trusted more than my own instincts, so I didn’t truly listen!

One solution is having people in your life where (1) you think they have high standards for what you're building, (2) you respect their opinion and will listen to them, and (3) the foundation of the relationship is strong enough that sharing negative feedback will not damage the relationship. When asked for feedback, these people will quickly give constructive feedback without much consideration for your feelings, which is good.

For example, here's a text exchange with a friend who I knew was reading the posts, and didn't hesitate to give me feedback that posts were dense and needed a way to summarize the insights, which led to the creation of TL;DR's at the top of posts.

Last week, I wrote a post on Founder/Product/Market fit. It's one of my favorite posts I've written. I was feeling good about myself and was getting some good feedback from readers. But I knew that couldn't be the full story. So I texted my old co-founder. He has an extremely high bar for writing, I respect his opinion, and our relationship has weathered lots of negative feedback over the years. There isn’t much he could say at this point which would hurt our relationship. He proceeded to hand me my ass, accurately telling me that the post tries to do too much and diving deep into how I can be improving my writing.

Having these high-trust sources of negative feedback that can give feedback swiftly creates a tight feedback loop, helping me improve my newsletter at a fast rate.

Proactively seeking and encouraging constructive feedback from others

In the Getting Shots Up Feedback Survey I shared at the top of this week's newsletter, I intentionally phrase questions to encourage the respondent to provide negative feedback. This doesn't come naturally to people when providing feedback, so I make it really acceptable (and expected) that they deliver the tough stuff. I try to normalize negative feedback. Here are two examples of questions:

Also, when I receive positive feedback from a reader, I take it as an opportunity to dive deeper and get negative feedback.

For example, after publishing Making progress on ventures before even starting, a reader (and friend) texted me:

“This piece might be my favorite of the series so far. Really like the traction vs. progress piece - ties into intellectual honesty too.”

After some banter, I pivoted the conversation to some constructive feedback. Even when he was hesitant to provide the feedback, I pressed harder and ended up getting extremely constructive feedback:

What you're writing is definitely share-worthy, I think the opportunity you have is making it easier for people to share.”

Negative feedback is part of what we sign up for as entrepreneurs. As Noah Shanok put it in our interview,

We're also resilient folks, entrepreneurs. We're used to getting knocked down. Our job is basically to get knocked down and get up every day.

It's better to seek out your own ass-kicking than for someone to blindside you with one. Normalizing negative feedback and thinking of negative feedback it like a fun, inevitable part of the entrepreneurial journey makes it easier to remain intellectually honest. With higher intellectual honesty, we remain in command of our entrepreneurial ventures (and careers) and can quickly take actions that improve. The truth is that there is always negative feedback out there – it’s just a question of whether we know what it is or if we’re choosing ignorant bliss.

One final reminder, feel free to kick my ass with this feedback survey. I’m counting on it.