Brad Feld has spent decades operating by a simple principle: give without expecting anything in return. This philosophy goes beyond traditional pay-it-forward thinking, he says. It’s about helping others, knowing only that meaningful connections and opportunities will emerge organically over time if you do.

The entrepreneur and VC, who began angel investing in the 1990s, rose to prominence through his candid blog “Feld Thoughts,” which pulled back the curtain on the then-secretive venture industry and sparked countless discussions across Silicon Valley. After decades as an investor and co-founding both Techstars and the venture firm Foundry Group — which backed hundreds of companies over 18 years before deciding to stop raising new funds in early 2024 — Feld has distilled his approach to business and life into his latest book, “Give First.”

TechCrunch talked with Feld last week about mentorship, boundaries, and why vulnerability might be the most important leadership skill.

You’ve been thinking about this “Give First” concept for over a decade. What finally pushed you to write the book now?

This is my ninth book, and I was getting close to being done with writing nonfiction; I’m interested in exploring science fiction writing. The intersection of maybe this being my last book and really wanting to capture these ideas made me sit down about three years ago.

The concept emerged in 2012 in my “Startup Communities” book as a paragraph called “Give Before You Get.” The idea was that if you want a startup community to really move, you need people willing to put energy in without defining upfront what they’ll get back. It’s not altruism — they’ll get something, but they don’t know when, from whom, over what time period, or in what form.

You were once seemingly everywhere, then you pulled way back. After taking a two-year break from public life, what brought you back?

I decided I didn’t want to be involved in anything public-facing. I was tired and burnt out. I focused on behind-the-scenes work, which meant [my wife] Amy and I were together all the time because I wasn’t distracted by other stuff. That’s been really satisfying.

When David Cohen came back as CEO of Techstars a year ago, I told him I’d engage as much as he wanted, but I still didn’t feel like being public. Working with him on strategy got me super deep back into it. I also took the [book draft] off the shelf, looked at it, and thought, “This is pretty good.”

This book is really about mentorship in its different forms. You also talk about the importance of setting boundaries to avoid burnout. There’s a reason for the adage ‘no good deed goes unpunished.’ How should mentors protect themselves while still giving generously?

There’s a lot of that in the book. I’ve been very open about mental health struggles to help destigmatize these issues. . .and there aren’t absolute answers to the question. One challenge when you’re willing to contribute energy without being transactional is that there are people who can’t do that, or who are extractors.

Adam Grant describes this spectrum in “Give and Take,” with givers on one end, takers on the other, and traders in the middle. Most of our world, really, is traders to takers. Over the short term, takers can do extremely well, but over the long term, people at the giver end are much more successful when success isn’t simply measured as power and money.

You emphasize the importance of saying “I don’t know” when mentoring. Why is that so crucial?

It’s extremely harmful to new founders when experienced, successful people position themselves as having the answer to everything. The magic in entrepreneurship is having lots of hypotheses, testing them quickly, and learning when most fail.

We’re in an environment where people can’t present things as hypotheses. They present them as assertions. The blurring between opinion and fact is a mess. The best mentors provide data and hypotheses, not assertions about what you should do.

One of [my] mentor manifesto phrases is “guide, don’t control.” Sometimes you do know the answer, but anyone who’s been a great manager knows the best way to get commitment is to get people to make the commitment themselves.

There’s a lot of opinion shopping that goes on behind the scenes. How should founders navigate conflicting advice from multiple mentors?

When I got feedback on my first draft [of the book] from 25 people, I absolutely got conflicting information. The more mentors can make feedback from their own experience, the more useful it is. Instead of saying “here’s what you should do,” they should say, “here’s an experience I had that’s similar, and here’s what I did.”

If mentees listen that way, mentor whiplash is no big deal; you’re getting multiple data points from multiple experiences. It’s less “choose your own adventure” and more synthesizing things that make sense in your context, making a decision, communicating it back to mentors, and then having them commit and support you.

At what point is someone ready to be a mentor?

Here’s the magic trick of mentorship: the best mentor-mentee relationships become peer relationships where the mentor learns as much from the mentee as the mentee learns from the mentor. That means essentially anyone can be a mentor at any point.

Some of the people I’ve learned the most from are at the very beginning of their careers—people still in college, running their first company. My friend Rajat Bhargava was 21 when we started working together in 1994. The amount we’ve learned from each other since then is unreal.

There are very successful, experienced people who are awful mentors, and people early on with little experience who are extraordinary mentors. Your ability to be effective as a mentor isn’t related to your success or experience — it’s a way of being.

How does this philosophy apply during times like now, where we’re seeing massive layoffs in tech, disruption from AI in everything . . .

Right now, there is almost zero predictive power associated with anything anyone is saying. We’re so disconnected from understanding what will actually happen. The very loud, extreme pronouncements people are making have the lowest predictive power I’ve ever seen.

We’re living in a space where it’s loud and jarring, but I’m hopeful this stuff is timeless. My goal with this book isn’t for people to say I got it right. It’s to stimulate people to think differently about some things, or reinforce what they’re already thinking in an additive way.

You’re still managing funds and assets dating back almost two decades. Any final thoughts on stepping back from the traditional venture model?

Amy and I say it all the time: we’re all going to die. We don’t know when that day is. What are you going to do with your precious life? The number of people hanging on to relevance by their fingernails in their 70s and 80s . . . if that gives you meaning, awesome. But for many, the answer [to the question of whether or not to do that] is not yes.