Brad Feld

Category: Books

The third edition of Venture Deals is now available on Audible. It’s the unabridged version read by me and my partner/co-author Jason Mendelson with guest appearances by Matt Blumberg.

We’ve been getting requests for an unabridged audio version of Venture Deals since we first came out with the book in 2012. We like to think that it has now aged like a good wine.

If you are an audiobook person, you can know hear the dulcet tones of Jason’s voice alongside the scratchy whine (which has aged) of mine while learning how to be smarter than your VC and your lawyer.


I just finished the near-final draft of Cat Hoke’s upcoming book Second Chance. It is incredibly powerful on multiple levels.

I’ve gotten to know Cat reasonably well over the past year. I first heard of her through the Techstars Foundation, where we gave her organization – Defy Ventures – one of our very first grants. I first met her a few months later in my office. After hearing her pitch for 15 minutes, I said “Cat – I’m all in – no need to sell me. What can I do to help?”

Cat, in her inimitable style, said, “The first thing you should do is to come to prison with me.”

A few months later I spent the day at California State Prison, Los Angeles County in Lancaster with Cat, 50 EITs (Entrepreneurs-in-training), and 75 volunteers. I wrote about it as one of my top ten life experiences in my post Understanding Privilege – My Experience in Prison. Amy and I made a significant gift from our foundation (the Anchor Point Foundation) immediately after the trip and I joined the Defy Ventures board two months later.

Since then I’ve gotten to know Cat, her husband Charles, and the Defy Ventures organization. While I’ve learned a lot about prison, the criminal justice system, and the concept and experience of privilege, I’ve learned even more about myself. And I have Cat, Defy Ventures, and all of the people around Defy (both inside and outside of prison) to thank for that.

But, as Cat so eloquently says, she doesn’t scale. When I first heard of Defy, it was about 20 employees. Today it’s over 50 going to 100. Like many fast-growing startups, the CEO (Cat) has to evolve in her role. While it’s hard, Cat is doing a magnificent job of it. It was logical that she’d write a book about herself, her own second chance, Defy, the work that it does, and how/why it matters and impacts people and society.

Writing this book must have been incredibly challenging. Cat is an extremely hard worker. She travels constantly. Her work is emotionally intense and she puts 100% of herself into it. So, when I was on about page 80 of Second Chance, I thought to myself, “This is incredible. I can’t imagine how much extra energy of Cat’s went into this.”

She had one of the best guides in the world – Seth Godin. I’ve been friends with Seth since the mid-1990s when I met him doing diligence for SoftBank in conjunction with Fred Wilson on the investment that SoftBank and Flatiron Partners (Fred and Jerry Colonna’s new VC firm at the time) made in Seth’s company Yoyodyne (later acquired by Yahoo!). I felt a deep connection to Seth from day 1 and even though we don’t spend much time together, ever interaction with him is treasured by me.

I can see Seth’s fingerprints all over this book. As an enormous fan of Cat’s, I’m so glad Seth took this project on. I expect their collaboration will have an important and lasting impact on the world.

You’ll get more specifics, and a full review, once Cat’s book is published. Until then, if you are interested in learning more about Defy Ventures or getting involved in any way, just email me and I’ll connect you.


Recently, my friend Ross Baird came out with a new book, The Innovation Blind Spot. In the book, Ross outlines and diagnoses a problem that I’ve been exploring for over a decade: our innovation economy neglects many people and ideas.

Ross kicks off the book with some pretty stark statistics: despite the fact that promising startup communities (such as my hometown of Boulder) are thriving, in most communities in America, firm creation is the lowest it’s been in a generation. With women making up less than 10% of new startups that are funded and African-Americans and Latinos making up less than 1%, it’s obvious we’re not seeing the best ideas in our innovation ecosystem.

Ross’ book is important because he focuses on solving this problem through HOW we invest, not just WHAT we invest in. It’s not enough for tech firms to say “we need more diversity – let’s go find different founders!” The design in how we find companies, perform diligence and make investments have unintentional side effects that cut many people out. One example highlighted in the book is that the very act of “pitching” a business tends to favor men (a Wharton study showed that men were 60% more likely to raise money pitching the exact same business as women.)

I’ve been thinking about ways to design startup communities to be more inclusive. A classic investor problem is a tension between wanting to be accessible to new founders while at the same time giving existing portfolio companies the time they deserve. When you’re getting a thousand pitches a year, you often tend to gravitate towards the people you already know and ideas that are familiar. Techstars has been a key part of addressing this issue for us as we’ve met thousands of companies we wouldn’t have otherwise and have invested – both directly and through our investment in Techstars – in a wide variety of founders all over the world.

Ross’s book also explores ways to build a stronger pipeline of different types people. As I’ve dug further into the problem, I’ve seen consistent ways that many people are excluded. For example, entrepreneurs go to conferences and network in order to find customers and investors. If you don’t have personal savings or family members who can help support you, you can’t afford that plane ticket. Organizations like the Techstars Foundation are working on addressing problems like this.

My favorite part of the book is when Ross talks about how places and communities can support their own founders. Ross’ final section is titled with one of my favorite words: “Topophilia“, or “love of place”. It’s a phrase I’ve embraced as we’ve built our startup community in Colorado and have tried to share with other communities around the world, both in my travels and through my book, Startup Communities. Whether you live in Cincinnati or Jakarta, you are far better able to help the entrepreneurs in your hometown than I am. I think that in order for us to ensure that entrepreneurs flourish everywhere, communities need to embrace them, and I’ve enjoyed being part of a community of folks like Ross who are trying to help communities do this worldwide.

Ross’s book is a quick, entertaining, informative read that diagnoses how we can do better as a startup community, and more importantly, focuses on the HOW. I encourage everyone in the innovation economy to read it.


In response to my post Book: Against Our Will: Men, Women and Rape several people asked me for the feminist literature reading list that Amy had put together for me.

Following are the other ten books that I’m working my way through this fall.

Sexual Politics by Kate Millet
Sisterhood is Forever by Robin Morgan
The Feminine Mystique by Betty Friedan
Sister Outsider by Audre Lorde
Ain’t I a Woman by bell hooks
The Second Sex by Simone de Beauvoir
The Female Eunuch by Germaine Greer
In Search of Our Mother’s Gardens by Alice Walker
A Room of One’s Own by Virginia Woolf
Beyond God the Father by Mary Daly

If there are any that you’d like to add to my reading list, please leave them in the comments.


“Men are afraid that women will laugh at them. Women are afraid that men will kill them.” – Margaret Atwood

A few weeks ago, after reading the New York Times Sunday Review article The Book That Made Us Feminists, I asked Amy for several recommendations for books that were foundational to the feminist movement. I purchased all that she suggested and added them to my infinite list of books to read.

The past few days I read Susan Brownmiller’s book Against Our Will: Men, Women and Rape. Written in 1975, it’s 480 pages of intense and powerful writing. After about a third of it, I turned to Amy and said, “That Margaret Atwood quote has a clear basis in history.”

Today, again in the New York Times (this time online), I read the article Push for Gender Equality in Tech? Some Men Say It’s Gone Too Far. I was almost finished with Against Our Will so it didn’t take much to infuriate me about the article. There are several men quoted in the article and others referenced. The only one whose perspective makes any sense to me is Dick Costolo’s quote.

“In just the last 48 hours, I’ve spoken to a female tech executive who was grabbed by a male C.E.O. at a large event and another female executive who was asked to interview at a venture fund because they ‘feel like they need to hire a woman,’” said Dick Costolo, the former chief of Twitter, who now runs the fitness start-up Chorus. “We should worry about whether the women-in-tech movement has gone too far sometime after a couple of these aren’t regularly happening anymore.”

In many of the conversations I’ve had around sexual harassment and sexual assault, I’ve been discussing something I’ve been referring to as the “perpetrator / victim paradox.” In this situation, the perpetrator “assaults / harasses” the victim. When the perpetrator is discovered (or almost discovered), he becomes the victim and tries to manipulate the victim into “not destroying my life.” It alternates between threats (continued perpetrator behavior aimed at the victim) and pleas (where the perpetrator takes the role of the victim, often using guilt to try and keep the victim quiet.)

Now, this doesn’t only apply to sexual harassment and sexual assault, but to any power dynamic. Which leads to the well-discussed idea that rape is much more about power than about sex. Brownmiller’s book does an incredible job of linking power to sex, especially in the context of men using sex to assert their power over women. But there was another level that jumped out at me, which was the notion of women as property, where a first man asserts their power over second man by having unwanted sex (rape) with the woman who was “affiliated” (wife, child, sister) with the second man. While Brownmiller has an incredibly long and distressing chapter on rape as part of the spoils of war, this idea infiltrates much of the book.

When I read articles like Push for Gender Equality in Tech? Some Men Say It’s Gone Too Far all I can think of is “these men are afraid of losing power to women.”

As a man, I wish other men would get over this. As our current president assembles the most male-dominated government in decades it’s clear that there is still a lot of work to do here.


The Audible version of Startup Opportunities: Know When to Quit Your Day Job, 2nd Edition is available for pre-order and will be on out on 9/19. My co-author, Sean Wise, read it using his deliciously dulcet voice.

Jason and I also finished the Audible recording of Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist, 3rd Edition and expect to see it up on Audible in 60 days. More when it’s out.

It’s a lot of fun to read your own audio book like I did for Startup Life: Surviving and Thriving in a Relationship with and Entrepreneur, the book I wrote with Amy.


I read Sheryl Sandberg and Adam Grant’s book Option B: Facing Adversity, Building Resilience, and Finding Joy a few weeks ago. It’s a must read for every human on this planet.

Some of you know that I’m a huge fan of Adam Grant. His book Give and Take: Why Helping Others Drives Our Success is a key inspiration for the #GiveFirst moment, my own personal philosophy, and my upcoming book #GiveFirst: A New Philosophy for Business which should be out in 2018.

I’m also a huge fan of Sheryl Sandberg. I don’t know Sheryl well, but we hung out a few times 15 years ago and both Amy and I thought she was awesome. It’s been awesome to watch what she’s achieved – first at Google, and now at Facebook.

It’s even more remarkable to read the clarity with which she has processed the sudden loss of her beloved husband Dave Goldberg. I met Dave a few times in the last 1990s when he was running LAUNCH Media (we were investors via SOFTBANK) but didn’t stay in touch after Yahoo! acquired LAUNCH. However, many of my Bay Area friends were close to Dave and viewed him reverently.

Amy and I have lost several close friends in the past three months to cancer and suicide. Another friend was recently diagnosed with stage 4 cancer. We are getting older and death is becoming a more visible part of our life experience.

Exploring how to process mortality is hard. I talked to a friend on my way home last night who is struggling with this. While these conversations are hard, I learn a little with each one.

Recently, I’ve been referring friends to Atul Gawande’s amazing book Being Mortal: Medicine and What Matters in the End which is the best book I’ve read so far this year. I also send them to Paul Kalanithi’s book When Breath Becomes Airwhich was one of the best books I’ve ever read. I know “best” is a weak qualifier, so just know that they are both in the same league as Norman Cousins’ classic Anatomy of an Illness as Perceived by the Patient: Reflections on Healing and Regeneration which had a profound impact on me in my mid-20s.

I just added Sheryl and Adam’s book to this league. Life and death are complicated. If you, like me, are constantly exploring it and trying to understand it, and yourself, better, I encourage you to read Option B: Facing Adversity, Building Resilience, and Finding Joy. Sheryl and Adam – thank you for writing it.


The Red Web: The Struggle Between Russia’s Digital Dictators and the New Online Revolutionaries was one of two books I read this weekend (the other was Brain on Fire: My Month of Madness).

It was outstanding. I made it the August book club book for my dad and my brother. And then, this morning, I woke up to the following headlines.

This shouldn’t be a surprise to anyone who is paying attention. There is now a long history of governments trying to control the Internet. One approach over government is censoring the Internet; another is weaponizing it.

The Red Web covers Russia’s history around the Internet starting during the Cold War with a focus on the last twenty years. While Russia had a slow start, the Internet played a big part in both sides of things – the increasingly free flow of information combined with government control over information.

I believe we are at the very beginning of a new version of this battle. Since the beginning of humans, information – and the control of information – has been one of the key dynamics of power. At least we don’t need to use ravens anymore.  But, depending on which country you are in, they might be a good backup plan.


My newest book, Startup Opportunities: Know When to Quit Your Day Jobis available via Kindle for $0.99 today. If you are a fan of my books, a friend, or just someone who is interested in startups, buy a copy today.