Brad Feld's Blog, page 5

Beware the Grinfuckers

I did a talk with a private community of 100 GPs and investors in venture capital called Aces last week. It’s an off-the-record, confidential group organized by a few people, including Max Beaumont, who said I could mention him in this post.

Max sent me the following summary. I asked him if I could post it, and he said yes.

Thank you again for taking the time to join us yesterday, and for staying well past the scheduled end.. I could tell how meaningful the conversation was for those who stayed..

A few takeaways that stuck with me:

Venture ≠ Asset Management – The game has drifted from backing outlier founders to chasing AUM. A painful reset might be needed before things get healthy again.Build a firm you enjoy – Not one optimized for market cycles. Sovereign wealth and busted endowments will keep distorting VC until liquidity dries up. Best to play your own game.Absurdism as antidote – Life is inherently absurd, so stop optimizing for status. Just be here now, with people you actually like.Beware the “grinfuckers” – Never tell people what they want to hear just to “gain.” The long game is living in alignment with your own beliefs.Stop passively avoiding – If something’s broken, confront it quickly. Avoidance only prolongs the pain.

Very grateful for your time and most importantly, your candor.. I find it hard to get “real” answers from most GPs today.. Too much incentive to bullshit. You were refreshing.

While there is plenty to unpack in each of those bullet points, especially since the conversation went on for about an hour (instead of the scheduled 30 minutes), the bolded headlines are an excellent summary of several of my core beliefs. None of this was scripted, thought through in advance, and all was summarized from Max’s perspective. I’m sure how I explained some things wasn’t as precise as if I had sat and written a long blog post about it.

So, look at the bold and apply your frame of reference to it. I’ve already written about The Cost of Passive Avoidance, so maybe there will be posts on the other topics, although I’ve also already covered Grinfuckers in the past.

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Venture Deals Summer Course 2025 Enrollment Is Open

Registration for the Venture Deals Summer 2025 online, self-guided, free course by Techstars and Kauffman Fellows starts today.

It’s based on the book Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist. When Jason Mendelson and I wrote the first edition, one of our goals was to eliminate the massive information asymmetry between entrepreneurs and investors. Venture Deals is now in its 4th edition and has continued to be a popular and helpful book.

This course will help you:

Understand the players within the venture capital ecosystemTarget the right investors for your companyLearn best practices for investor engagementLearn how to structure financings using term sheets, capitalization tables, and syndicationLearn negotiating tacticsLearn more about Diversity, Equity, and Inclusion in the venture capital ecosystemLearn more about mental wellness strategies during the fundraising journey

The course starts on June 5 and has limited availability. Previous courses reached capacity quickly, so sign up for Venture Deals Summer Course 2025.

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The Power Of Mentorship: A Conversation With Brad Feld and Phil Weiser

On Saturday, May 31st, from 3:30 to 5:00 PM in downtown Denver, I’ll have a public conversation with Phil Weiser about various topics, including technology and innovation in Colorado. We will also talk about what (and how) we’ve learned from each other over the years and how we’ve worked constructively through disagreements, conflicts, and mistakes.

Phil’s blog post Startup Community Leadership discusses many of the things he’s done to positively impact the Colorado startup community. My journey with Phil started in 1999 when he co-founded a new center at CU Boulder: the Silicon Flatirons Center for Law, Technology, and Entrepreneurship. While unfortunately named (I hate the name Silicon X for anything, and over the years, I’ve teased Phil many times about this), this began a collaboration between us that resulted in organizations like Startup Colorado and BEN Colorado. It also resulted in the New Technology Meetup, the Entrepreneurial Law Clinic, the Entrepreneurs Unplugged Series, and CU Boulder’s New Venture Challenge.

If you’ve read my book Startup Communities: Building an Entrepreneurial Ecosystem in Your City, you know about the incredible impact that Phil and Brad Bernthal had on engaging CU Boulder with the Boulder Startup Community, starting around 2007. It meaningfully impacted how I thought about how the culture across a University could be changed around entrepreneurship and engagement with a local startup community. I attribute much of the early leadership here to Phil and Brad, who worked as incredible thought partners early on the new approach to developing startup communities I codified in that book, and it has now had a global impact.

Given the other public conversations Phil and I have had, including one with Jamie Dimon at CU Boulder as part of Entrepreneurs Unplugged, I expect we will cover a wide range of topics. It’s a chance to get to know another side of Phil and better understand how we’ve learned from each other over the past 25 years on technology, entrepreneurship, startup community development, government involvement with technology and innovation, leadership, and mentorship.

Anyone who attends will receive a copy of my newest book, Give First: The Power of Mentorship, which I will happily sign if they wish.

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Turn Every Page

I learned how to do deals from Len Fassler. Last week, I got an email from Dustin Kloempken, who sent me a few quotes he wrote down from the Berkshire Annual Meeting. One of them jumped out at me.

“Turn every page. One important ingredient in the investment field that very few people do. And those people who did read every page aren’t telling you what they learned. You have to read every page.“

In 1996, I was sitting in a law firm conference room in NYC next to Len. We were working on the legal documents for Sage Hosting’s (which we renamed Interliant after we merged with a company named Interliant) first acquisition. It was tiny—a web hosting company doing maybe $100,000 of revenue annually. We had decided to buy this tiny company to get going.

Len read every page of the legal draft of the purchase agreement and marked it up. After reading a page, he’d slide it over to me to read and see what he’d marked up. We had the disclosure document, so we went through those pages.

By 1996, I’d done a lot of angel investments and a few VC investments, but only a few acquisitions. And, I’d deferred to the lawyers on the legal documents. While I generally knew what was happening, there was plenty of fine print that I hadn’t bothered to read or understand.

After an hour, I asked Len why he was going through every page. He told me, “Brad, in any document you sign, you should turn every page. It’s good practice for any document you read, but even if you are skimming, turn every page to make sure you don’t miss anything.”

I bought a green felt-tip pen and started doing this. As documents became predominantly online, I opened them and turned every page. I read every email I received. Even when I skim a book, I turn every page.

Today, I received many Docusigns with just the signature page. This bugs me, and I often ask for the entire document before I sign. Given that I’ve looked at a zillion legal documents, I can turn every page pretty quickly. But I still turn every page in a board package, a legal document that is new to me, or a long paper (academic or white paper) that someone sends me.

Fortunately, I’m a fast reader and have high reading comprehension. I can also read by paragraph (vs. by sentence), so skimming works for looking for things that are out of place.

I love it when people put easter eggs in documents to see if they get read. For example, a set of Return Path board minutes from about a decade ago had something like the following paragraph.

“After our lunch break, where we enjoyed Shake Shack, Mr. Feld drank two Shake Shack Chocolate Shakes in rapid succession. After a few minutes, he had to lie on the floor and nap for about 30 minutes.”

Turn every page—great advice from Len Fassler and Warren Buffett.

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Random Day on 5/28 at The Composition Shop

I’m going to have a Random Day on 5/28 at The Composition Shop in Longmont. I plan to be there from 11 am to 5 pm with a break for a lunch meeting from 1 pm to 2:30 pm. We will have copies of Give First: The Power of Mentorship in the store on sale, even though the book’s official release date isn’t until June 24th, because my Colorado friends get special bonus early bird stuff.

I have nine random day slots (15 minutes each), and I’ll hang out between them for anyone in the bookstore signing books. I’ll also have a bunch of my other books there that day in case you are interested in one of them (and yes – I’ll sign them also).

The Composition Shop is a new bookstore created by Greeley Sachs, an extremely close friend married to my Foundry partner, Seth Levine. Greeley has bought several buildings on Main Street in Longmont and is new and improving the area. So, in addition to participating in Random Day, give Greeley and her new bookstore some love (she’ll be there all day also, and maybe some other Foundry partners will come by).

Sign up is first-come, first-served below (click on the Jump to the next bookable date button). If Mailchimp blows the link up, like it did with my AC/DC YouTube video, just click through to my website – it works there.

If you don’t know how Random Day works, here’s an excerpt from Give First: The Power of Mentorship.

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Back in Boulder

As a proud early Gen Xer, I was in ninth grade when Back in Black came out. It was my favorite song for at least a week, and it’s still in my top 10 (something by Rush likely displaced it.) As a teenager, I knew everything about AC/DC (at least everything you could know before the Internet existed.) I wandered around that week proudly telling everyone who would listen that the song was a brilliant tribute to Bon Scott.

Amy and I arrived in Boulder on Friday and will stay for a month before heading to Aspen for the summer. As I emerge from hibernation, I feel the song’s energy. So far, I went to the Nuggets game Friday night, had brunch with friends on Saturday at Tangerine, took a long nap Saturday afternoon to try to reset my system, ran on the Boulder Creek Path on Sunday morning, and had dinner with Amy, my brother, and his wife at Barchetta last night.

Boulder Startup Week (the oldest Startup Week in the world) begins this morning. I’m about to head out to the opening event at Rosetta Hall, about three minutes from my condo, since we live downtown now.

Even though there is enormous craziness in the world right now, I’m bringing my full self to the summer. I hope to see you in person, online, or via email.

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My Upcoming Events in Boulder

Now that I’m out of hibernation for a while and back in Boulder for a month, I’m doing a bunch of public events.

My approach, in general, is fireside chats or AMAs, so that’ll be the rhythm rather than me getting up in front of a crowd and blathering about something for 30 to 45 minutes. While my new book, Give First: The Power of Mentorship, is part of the content (and a giveaway that I’ll be signing at some of the events), I’m planning on staying around, talking to whomever is there, and just enjoying a month of the Boulder and Denver startup communities.

The following is what is currently scheduled. I expect there will be a few more things.

5/12 @ 8am: 2025 Boulder Startup Week: Welcome Breakfast and Kickoff to Boulder Startup Week: There will be lots of socializing as Boulder Startup Week gets started. Join me for breakfast and a short talk on the roof of Rosetta Hall. The rumor is that the weather is going to be awesome.

5/13 @ 3pm: 2025 Boulder Startup Week: Startup Communities – The Next Generation: My partner Jaclyn Hester and I will have a fireside chat about the evolution of a startup community. We’ll talk about the importance of existing leaders (e.g. me) to hand off the torch to the next generation (e.g. Jaclyn), why the development of the startup community is not a straight line up and to the right, and how to incorporate concepts from my upcoming book Give First: The Power of Mentorship into your daily activities in the startup community.

5/16 @ 10am: 2025 Boulder Startup Week: Building and Managing Your Board: I’ve been on a zillion boards. This panel includes several people with whom I’ve been on great boards (Tim Miller, Todd Vernon), along with Walter Knapp (my partner Seth is on his board). I’m also been on a lot of mediocre boards and several crappy ones, so I’ll bring those experiences to the discussion also.

5/28 @ 11am – 6pm: Random Day at Composition Shop: I’ll spend the day at Greeley Sachs’ new bookstore in Longmont doing a Random Day (where I have 15-minute meetings with anyone who wants to meet). Look for a separate post with an online calendar to reserve spots soon.

5/29 @ 2pm: 2025 Conscious Entrepreneur Summit: I’ll share my perspective on mentorship, community, and how Give First applies not just to business but also to the way we live and lead.

6/5 @ 5pm: Techstars Workforce Development Demo Day featuring a Book Launch with Brad Feld: I used to go to every Techstars Demo Day. I think this might be the first one I’m going to post-COVID, and I’m excited to experience its energy.

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This Week In Vibe Coding Learning

Question: If you had limited experience with graphic design software but wanted to do basic stuff for web design, what software would you use? Leave the answers in the comments or email me.

As I play around with Vibe coding, I’ve decided to take a new topic each week. For context, look at my Dinostroids: My Journey into Vibe Coding. Or just go play Dinostroids.

This week, I’ve been learning how to modify WordPress themes. My website has a complex theme that is impossible to change without getting under the hood. The Foundry website is also excessively complex for what it is, but they both turn out to be great to learn on.

I understand PHP well enough to read it. After working through WordPress Studio, GitHub, and Cursor, I’ve set up my development pipeline.

While the code is a little gnarly, it’s not too bad, and it’s pretty easy to figure out what’s going on. But the wall I’m running into now is that I’m a lightweight at graphic design.

While Adobe Photoshop is an obvious choice, and Canva is another obvious choice, I’m looking for “what’s best for a graphic design novice.” Thoughts?

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Book: Carrie Soto Is Back

I had a weird, unsatisfying, and not particularly restful weekend because of Colorado politics and post-exertional malaise. So, in between work, a short run, a long nap, a bunch of online Swedish death cleaning, and lying on the couch responding to endless text messages, I read Carrie Soto Is Back and The Big Gamble (Kevin Kerney Novels Series Book 7). And when I say “read”, imagine me on the coach, with my Kindle in one hand and my iPhone propped up on my leg so I could read what came in and respond when necessary.

The Big Gamble was good. I’m enjoying cruising through the Kevin Kerney novels after consuming the entire C.J. Box Joe Pickett series (all 25). But Carrie Soto Is Back was spectacular.

I was a serious tennis player from age 10 to 14. While football dominated Texas sports, well, forever, tennis was up there in the mid 1970s alongside soccer (anyone remember Kyle Rote Jr and the Dallas Tornados?) I stopped playing tennis when I discovered computers and girls (in that order) and started running instead. For my 30th birthday, Amy took me to Bollettieri Tennis Academy (RIP Nick Bollettieri), which rekindled a casual interest in tennis for me and a serious interest in tennis for Amy.

Today, Amy is a tennis superfan. Our default TV channel is the Tennis Channel (turn on the TV and it goes to the Tennis Channel). She always talks about Rafa and compares all the new up-and-comers to him.

While I’m also a tennis fan, I’ve grown to enjoy watching the women’s games more than the men’s. Coco Gauff is my current fave, but I almost always root for the underdog. And while I rarely cheer for Sabalenka, she is an amazing player.

Carrie Sota was the best (fictional) female tennis player in the 1980s, winning the most Grand Slams of any player (20). She hurt her knee in 1987 and retired in 1989. The book starts in 1994 with Carrie watching the new top female tennis player, Nicki Chan win the US Open and tie Carrie’s record.

In 1995, Carrie decides to come out of retirement and compete in all the majors. If you are a tennis fan and this sounds familiar, it is a recurring theme in real-life tennis that rarely ends well.

The drama is phenomenal, and the character development of Carrie, Chan, Carrie’s father, her love interest, and a few other minor characters is outstanding. The story moves quickly, and the tennis match sections keep up the drama and pace. Our protagonist has multiple moments of increasing difficulty that aren’t histronic or hard to believe, many of which deal with her changing reality of life as she gets a little older.

When I watched (and then read) Daisy Jones & the Six several years ago, I thought Taylor Jenkins Reid was a gifted storyteller. I don’t know why it took me so long to discover and read Carrie Soto Is Back, but The Seven Husbands of Evelyn Hugo and Malibu Rising are now on my Kindle.

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The Cost of Passive Avoidance

It’s pre-order time for Give First: The Power of Mentorship. If you find this post’s topic interesting, help boost my input into the Amazon algorithm by pre-ordering the book.

I’ve failed at many things. Anyone with a lot of success has also had plenty of failure. If a successful person denies this, they are lying.

Reflecting on my professional failures, some resulted from passively avoiding a situation. These are the ones I regret the most because my behavior is under my control. While I’m comfortable with confrontation, living in a work world of endless conflict and negotiation, it took me a long time to fully acknowledge situations where I was passively avoidant.

Today, I separate passive avoidance, which I now try never to do, from active avoidance, where I’ve deliberately decided not to deal with or address a situation. When I’m actively avoidant, I tell the people involved I’ve chosen not to engage with the situation. When I realize I’m being passively avoidant, I either address the situation directly or decide to be actively avoidant and state that to the involved parties.

In Give First: The Power of Mentorship, I have a chapter for each of the 18 principles in the Techstars Mentor Manifesto. One of them is Be Direct. Tell the Truth, However Hard, and in that chapter, I have a section titled The Cost of Passive Avoidance.

Following is an excerpt.

Recently, the concept of “the truth” has become elusive. While mistruths, lies, and deceit have been a foundational part of our species’ communication, a new level of misdirection and deflection around being direct and telling the truth became popular when the phrase “fake news” became part of our vocabulary.

In entrepreneurship, passive avoidance is a pernicious version of avoiding the truth. Every crisis communication playbook has a chapter on ignoring the crisis and pretending it’s not happening. This approach is related to deflection, another deeply destructive maneuver from the crisis communication playbook, which follows another strategy: attack.

There are moments when I’m too tired or frustrated to deal with a situation. Or, I disagree with a path a team is going down, but I have other things on my mind, and I don’t feel like bothering with it. Or I’m tired of arguing with someone, don’t care anymore, or feel defeatist about the situation. That’s passive-avoidant.

Reflecting on my past, I often regret when I was passive-avoidant. Many of my disappointments can be linked directly to being passive avoidant. When Amy challenges me about something at work, it’s usually about me being passive-avoidant. I feel anxiety when I’m avoiding dealing with something. And, when I look back at some of my depressive episodes, they often were triggered by an accumulation of avoiding things, including my own physical and emotional health, that I let build up until I couldn’t handle it anymore.

If you realize you are acting passive-avoidant, pause and consider why you have fallen into this behavioral trap. Step back and get to the root cause of what is bothering you. Apply the Five Whys to the situation. Once you discover the root cause, decide if you should take action to address it. Or, should you disengage? Either way, you are now ready to be direct about what you are thinking, feeling, and going to do.

Passive-avoidant behavior is occasionally inevitable. But if you do it repeatedly, it builds up. You start being unable to confront situations. You begin avoiding being direct. Consequently, the other person doesn’t hear challenging information that could impact their behavior. You stop telling the truth and get caught up in your deceit around a situation. You withdraw, where silence can do as much damage as
hostility and attack.

I put much of myself and my personal philosophy into this book. In addition to conceptual explanations, there are plenty of examples from my own experience, such as the section immediately following, titled Young Adult Lessons from Lying and Being Lied To.

I’m looking forward Give First: The Power of Mentorship being out in the wild and getting feedback on what rings true, what I could have explained better, and what doesn’t resonate.

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