Brad Feld

Category: Technology

I got an email from Matt Blumberg this morning with the above image that said,

“We have been blogging for 19 years. I can remember sitting together above Super Liquor futzing with Typepad like it was yesterday.”

“Super Liquor” is Superior Liquor in Superior, Colorado, which was on the first floor of the building off of Hwy 36, which was my office at the time. There was also a pizza restaurant on the first floor.

I asked Matt if we started on the same day because I couldn’t remember. He said,

“Literally the same day.  We sat at a desk right outside your office in Superior, pulled up our laptops, and taught ourselves Typepad together and created our templates.  Fred had already been blogging for about 6 months, and we had dinner the night before (can’t remember where, think The Med) and decided we would give it a try.  We couldn’t find other good examples of VC or CEO blogs. “

I went and looked at some of those first few posts. Matt’s was You’re Only a First Time CEO Once. Mine included To Blog or Not to Blog (which called out a handful of VC bloggers who started before me), Blog tools – Newsgator and Moveable Poster, TDC (Thinly Disguised Contempt), and my first book review: Free Prize Inside the Radioactive Boy Scout Rate Hikes.

My favorite of those was TDC (Thinly Disguised Contempt).

As was the tradition at the time when new bloggers appeared on the scene, Fred Wilson wrote nice posts linking to each of us. His welcome to Matt was Welcome to the Blog World Matt, and his welcome to me was This Is Going To Be Interesting.

This post wouldn’t be complete without my hat tip to Fred, who, in my view, is the OG VC blogger. His first post was creatively (well – not really) titled MY First Post.

19 years is a long time to do anything. It’s close to my board service record, which ironically was on Matt’s company Return Path with Fred. The ending of Fred’s first post resonates with me today as it did 19 years ago.

“I have no idea if i’ll write a lot in my blog or rarely. I hope its a lot, because i have a lot to say. But we’ll see about that.”

Paul Kedrosky and Eric Norlin of SK Ventures wrote an interesting and important essay titled Society’s Technical Debt and Software’s Gutenberg Moment.

The abstract follows. I encourage you to read the full essay.

There is immense hyperbole about recent developments in artificial intelligence, especially Large Language Models like ChatGPT. And there is also deserved concern about such technologies’ material impact on jobs. But observers are missing two very important things: 

  1. Every wave of technological innovation has been unleashed by something costly becoming cheap enough to waste.
  2. Software production has been too complex and expensive for too long, which has caused us to underproduce software for decades, resulting in immense, society-wide technical debt. 

This technical debt is about to contract in a dramatic, economy-wide fashion as the cost and complexity of software production collapses, releasing a wave of innovation.

Dave Jilk and I had a long discussion last night, which included some rambling about AI. If you have been following me for a while, you know that in 2010 I stated that the machines have already taken over for us and are patiently waiting for us to feed all human knowledge into them.

This morning, Dave told me about the new HyperEncabulator project by SANS ICS as part of their ICS initiative. If you aren’t aware of the ICS initiative, it’s essential for industrial applications, especially IoT and security.

But first, some history, since it’s an evolution of, and inspired by, the Retro Encabulator initiative, which was foundational but little known in the arc of encabultors.

The HyperEncabulator came out in the middle of 2022. Notably, side fumbling is still effectively prevented.

When I asked ChatGPT, “How does a Retro Encabulator work?” they had an accurate but humorless response.

The Retro Encabulator is a fictional machine invented for an engineering-themed comedy sketch in the 1970s. It is described as “an intricate and implausible device for the purpose of regaining lost energy.” The Retro Encabulator is a humorous parody of an electromechanical machine and its purpose is to perform useless tasks. The machine consists of numerous components, such as pistons, flywheels, and other components, that serve no real purpose. The device usually ends up producing more energy than it consumes, although this is never explained.

Grammarly had a few suggestions to improve ChatGPT’s writing.

The Retro Encabulator is the fictional machine invented for an engineering-themed comedy sketch in the 1970s. It is described as “an intricate and implausible device to regain lost energy.” The Retro Encabulator is a humorous parody of an electromechanical machine whose purpose is to perform useless tasks. The machine consists of numerous components, such as pistons, flywheels, and other components, that serve no real purpose. The device usually produces more energy than it consumes, although this is never explained.

When I asked ChatGPT, “Are you aware how little a sense of humor you have?” they said, “No, I do not have self-awareness.” So I hope they figure out how to connect to the HyperEncabulator.

FYI – when I asked ChatGPT, “What are your pronouns” so I could write the previous paragraph correctly, they said, “My pronouns are they/them.”

I usually do a few interviews (podcasts?) at the beginning of the year. I avoid all of the end of the prior year “what do you predict for next year” stuff and find that several long-form interviews at the beginning of the year allow me to get out of my head what’s going on from my frame of reference.

If you know me, you know that I learn by doing, writing, reading, and thinking out loud. I find these interviews to be a good way for me to think out loud to solidify my transition into the new year.

I did two interviews right after the new year. One with Andrew Keen …

… and one with Jason Calacanis.

(0:00) Jason Kicks off the show
(2:49) Brad Feld, Co-founder of Foundry, talks about starting out in investing
(13:30) LinkedIn Jobs – Post your first job for free at 
(14:56) Brad’s thesis for whom he’ll get in the “trenches” with  
(20:48) MasterClass – Get 15% off an annual membership at
(22:22) Fighting to the end + Investing through the dot-com bubble
(38:13) Microsoft for Startups Founders Hub – Apply in 5 minutes, no funding required, sign up at
(39:43) Surviving the GFC
(44:23) Brad’s perspective on the investor/CEO dynamic + being a leader in a down market
(1:00:02) Reflecting on the speculative asset bubble
(1:16:44) Looking forward into 2023

They are both great interviewers willing to let me ramble when prompted vs. tie me into a structured interview.

So, if you like hearing me think out loud, I encourage both of them. Jason’s show notes include links to specific segments (listed above) if something specific catches your attention.

Same As It Ever Was

Jan 04, 2023
Category Technology

When I was in college in the 1980s, David Byrne and the Talking Heads were in regular rotation in my room along with Pink Floyd, except for the one semester where the only thing I listed to was Dark Side of the Moon (ah – the joy of discovering repeat on an early CD player.)

Once in a Lifetime was one of my favorites. Looking back, it was a Gen X anthem.

Mark Goldstein sent me an email this morning titled your blog, an article i was in last week and yep in response to my post What Just Happened. It included the phrase “same as it ever was…same as it ever was.” and a link to The Internet Is Kmart Now from The Atlantic.

Amy had texted me the article mid-December when it came out. It starts strong.

The 1990s hadn’t gone as expected. A bad recession kicked off Gen X’s adulthood, along with a war in the Middle East and the fall of communism. Boomers came to power in earnest in America, and then the lead Boomer got impeached for lying about getting a blow job from an intern in the Oval Office. Grunge had come and gone, along with clove cigarettes and bangs. The taste of the ’90s still lingers, for those of us who lived it as young adults rather than as Kenny G listeners or Pokémon-card collectors, but the decade also ingrained a sense that expressing that taste would be banal, a fate that the writer David Foster Wallace had made worse than death (I swear he was cool once, along with U2).

yep. Thankfully SiriusXM has Channel 34: Lithium.

The article uses the Kmart / / Spinway story to set up the conclusion. We were in the middle of it (Softbank Venture Capital/Mobius invested in and Spinway.) Ian Bogost mostly gets the story right. And then, he ends the article as strongly as he started.

Today, the collapse of a big technology or retail company is almost unthinkable. Just look at the pearl-clutching over Twitter’s recent shambles: The public can’t fathom the idea that it might decline, let alone possibly die, for real. But the certainty of death, rather than the hubris of assumed eternity, was the salient cosmic feeling of the 1990s internet. Its creators had learned that sentiment from the Cold War, tapping out time on Atari games about the apocalypse while awaiting its real-world counterpart. Of course Kmart died, and Yahoo too. What else could have happened? “We’re all going to be absorbed; we’re all going to be consolidated,” Goldstein said. “At the end of the day, we just hope to end up as a button that survives.”

Yep. Same as it ever was.

Password Insanity

May 05, 2021
Category Technology

My mom is extraordinarily patient.

Several weeks ago, I bought her a brand new Mac as a mother’s day present. She was using a 2010 Mac, and it was time for her to use one that didn’t have an endless spinning pinwheel of Mac slowness on it.

I had it sent to me, although there’s a whole story in just that. I set it up, downloaded and set up all the apps she used, installed all the new stuff she needed to manage her passwords from now on, connected iCloud, and tidied and buffed it. Then, I figured we could use Zoom’s remote control, so I thought all I’d need to do was ship it to her, spend a few hours with her walking her through everything, and she’d be in great shape.

I can be so naïve. And, since I’m no longer young, I don’t qualify as young and naïve.

She and my dad got it, set it up, and connected it to the new LG monitor I’d gotten her along with the Anker USB extender. Cables and connectors – lots of them. It’s kind of remarkable how hard Apple makes the transition from devices (iPad – different cable, 2010 Mac – different cable, 2020 Mac – different cable, connect old external hard drive – different cable.) So many cables.

Eventually, it worked and, after walking through giving Zoom access to the right things on the Mac (click on the little lock in the bottom left; now check the box next to Zoom; no, the one next to Zoom. Yes, Zoom in the window to the right of the lock…) I was able to connect remotely.

Day 1 was fine. We spent three hours Sunday afternoon going application by application. I copied all the files on her external hard drive (which she lovingly calls “her Toshiba”) to the new Mac. I enabled iCloud to upload all the files to the cloud, and we spent a bunch of time discussing why that would probably take a few days over their slow internet connection, but then everything would be on her computer and in the cloud. We tested all the apps to make sure they were pointed at her documents as a default so she could find them. We went through the approach with the new password manager, which means she has three different passwords, one for her Mac, one for iCloud, and one for the password manager. But, once she has these three memorized, she won’t have to keep the rest of her passwords for all her individual apps “somewhere.”

We had a short discussion Monday night to refresh a few things. Last night was the first day of working through the list she’d made during the day of issues and questions.

We spent three hours on issue #1. Passwords.

It should have been simple. I foolishly made the Mac and iCloud passwords the same, figuring that would be easier for her. But, after Apple let me do that, it eventually told her she couldn’t have them be the same (hours later) and prompted her to change the Mac password. She wanted the Mac password to be a different one, so I assumed all I needed to do was change the iCloud password, then the Mac password and all would be good.

Two-factor authentication slowed that down. She has an Android phone, and the authentication is on her iPad, but that took me a while to figure out. I think we entered a different TFA code a dozen times over the course of three hours on her iPad. Then, I thought we were all set, but suddenly the Mac password didn’t work. And just like that, we were logged out of the computer, and Zoom was disconnected.

150 minutes of misery ensued. At the two-hour mark, I said, “just ship the Mac back to me, and I’ll start again.” Mom really didn’t want to do this or have to start from scratch, so I pressed on with a full password reset using iCloud. But, of course, the iCloud password was now no longer working. I have a feeling that Apple, in the background, invalided both of them somehow, but what really happened is still a mystery to me. The big hint was the endless “You have been locked out of …” message on iCloud and the regular prompts on the Mac to use iCloud to reset your password. Um – ok.

And, you guessed it, Zoom wasn’t able to connect us while she was logged out of her Mac, so this ended up be me dictating what to type, with her taking screenshots of her Mac screen and texting them to me since she was an on Android phone and we couldn’t simply Facetime.

Eventually, I figured out that I could reset her iCloud password on her iPad, which was still logged into iCloud (thankfully, I didn’t say “log out all devices from iCloud” when prompted over and over again. So we did that (more screenshots), we then did a full password reset on the Mac using iCloud (I never knew that was possible) and re-entered a new Mac password.

Three hours later, she got back into her Mac. We were exactly back where we started. Except now she was getting a message that the Mac couldn’t log into iCloud. Launch Zoom. Connect. Grant remote access. System preferences. Apple ID. Log out of iCloud. Log back in. Reboot (oops – bye Zoom). The bad message was still there.

Well, at least she can get back into her computer.

I’ll take on that last error message again tonight. And try to get to item #2 on her list. Maybe.

We all know the current approach to passwords and security is completely busted, but I just lived three hours of how incredibly broken it is.

And, before you say “just use the Touch ID,” neither of our fingerprints work. It’s not just Apple, it’s Clear, Global Entry, and the fingerprint process for a money transmitter license, so there must be something genetically wrong with us. Plus, I’m pretty sure that would have just made it worse somehow.

Mom – thanks for not chucking the new computer out the window and going back to your old one.

Dear Discord: Please go public and stay independent instead of being acquired. Love, Brad.

I’ve become a huge Discord fan and user of the past year. I’ve got many daily reference points from products that I use for real-time communication channels: Slack, Telegram, Signal, iMessage, Zoom, Voxer, Mighty, and of course, email.

An increasing number of my group communications is on Discord. There was a ramp-up on Slack several years ago across organizations, but I find it noisy, not terribly easy to navigate, and tiresome for various reasons.

In contrast, Discord is much easier and feels much more vibrant for dynamic communities. This then leads to lots of 1:1 comms across organizations, which until recently was really difficult with Slack, which is now sort of, but not completely, fixed since Slack rolled out Connect.

I stopped using Twitter, Facebook, WhatsApp, and LinkedIn for any real-time comm stuff a while ago. While my iMessage is noisy, it’s calmed down a lot given wiring up some other stuff to the right channels.

I continue to believe that Zoom has a massive disruptive opportunity to obliterate Slack. Still, it’s clearly not a priority for them, and all that might now be irrelevant given Salesforce + Slack along with the Salesforce / Zoom relationship.

That brings me back to Discord. While it would be a smart move for Microsoft to acquire Discord, it would likely pin Discord into a particular segment of Microsoft given Teams along with Microsoft’s functional separation between their gaming business and their corporate business. I know nothing specific about the Microsoft / Discord discussions, but I expect it was primarily, if not entirely, on the gaming side of Microsoft. This would eliminate what I expect is Discord’s most interesting current vector, which is cross-organization collaboration within either affinity groups (communities) or for corporations with their customers.

I fantasize about having one app that deals with all the different sub-apps. Right now, that’s called “my computer” since I have to deal with many different apps. If the promise of APIs really came true, or if XMPP had worked out, or if Trillian had become a thing, this might have happened. But, as with most things in tech, the walled garden takes over when the revenue and profit imperative takes over in the context of monetizing users.

Real-time everything is broken right now. Yeah, it works at an application and network-level (quite brilliantly, and much better than 20 years ago), but it sucks at a user level.

There is so much to do here. Ironically, at least from my perspective, we need more companies (e.g., Discord – stay independent) rather than fewer companies working on this right now.

I expect we’ll be exploring, unscrambling, pontificating, and dealing with what is happening with GameStop (GME) for a while.

If you are reading this in the future and want some historical context for the rest of this post, this chart from the last 30 days of trading is instructive. At the end of 2020, we start at $20 / share.

30 days later, it’s at $238 / share with a high of $482 / share.

I’m not going to analyze this. I know what I think GME is worth, and it’s not $238 / share.

This morning, Fred Wilson wrote a post titled The Revenge Of Retail. It’s got a lot of good stuff in it, but plenty of things that are very different than what I’m actually thinking about today.

He ends with a recommendation.

What we need to do is stop printing money to stabilize the economy. And start addressing the real economic issues that exist on main street, not wall street. Monetary policy is not the answer. Fiscal policy is. That won’t stop more Game Stops from happening. They are a by-product of markets. But it will get the money to where it is needed versus where it is just gameplay.

I’m more interested in the 2nd, 3rd, and 4th order effects instead of the financial and market dynamics. For example, from Fred’s post.

The generational aspect of this is important. Boomer hedgies getting crushed by young folks self-organizing in social media. It feels like a moment where you realize that the power structure has shifted and things won’t be the same.

But hang on. Is that actually what is happening? Let’s go to something Fred says in his next paragraph.

The financial system in the US, and in other developed countries, is a rigged system and has been for a very long time. Only big institutions can get into hot IPOs. Only rich people can invest in startups. Many of these rules are designed to protect “widows and orphans” but all they really do is make the rich richer and keep those without money out of the game.

Rather than keep quoting Fred, I encourage you to go read The Revenge Of Retail post and then come back to the rest of what is on my mind this morning.

When I was an undergraduate in college (age 17 – 21; 1983-1987), I was interested in business and read three magazines: Forbes, Businessweek, and Fortune. I learned about the stock market by reading those magazines. That period was full of pump and dump schemes, especially on the pink sheets.

There have been periodic articles about the pump and dump activity in crypto. With the introduction of frictionless (e.g., free trading), a coordinated online crowd of millions of people, and low float stock (either highly shorted or not much supply in the first place), the setup for a classic pump and dump exists.

The regulatory environment has no capacity to keep up with something like this.

A combination of factors has created an environment where completely different behavior is possible. Today’s news is that it is happening in the financial markets. We may be talking about it here because we are now on the other side of 1/20/21; our prior President is no longer on Twitter and Facebook, so there’s a new sandbox to play in.

The dynamics are the same. Sentiment is manipulated. There have been endless discussions about this around politics over the past few years. Welcome to another part of our world (financial markets), where the unintended consequences of technology wreak havoc.

I expect we will see many more and many different examples emerge over the next few years. Governments trying to regulate it each time will be slow, and all will fail to do what they want to do while creating other unintended consequences.

We are living in a complex system. Technology has increased the velocity of change. It’s recursive, as the velocity of technology is changing faster than ever.

I have no idea what’s next. That’s the reality of a complex system. All I know is that it is going to get much wilder.

And, the best picture of the day is linked to a txt thread I’m on with Amy (we both love Capybaras) that includes the phrase “PhD in the madness of crowds.”

Minor change: I initially titled this “The Gamestop Phenomenon.” That’s a nice error on my part (freudian slip maybe)?

Until six weeks ago, my favorite software product of all time was Lotus Agenda. We ran my first company (Feld Technologies) on Lotus Agenda from when the first version of Agenda came out sometime in 1990 to when we sold the company in 1993. If you aren’t familiar with Agenda and want a quick, readable description, take a look at AGENDA: A Personal Information Manager (Belove, Drake Kaplan, Kapor, Landsman).

Agenda was the brainchild of Mitch Kapor (and several others) and, after Lotus killed it off in the time of a transition to Windows (Lotus Organizer was not an adequate Windows replacement), there was an effort (again led by Mitch Kapor) to recreate it with an open-source project called Chandler that never came to fruition.

Agenda is the only product that augmented my brain and how I think until I started using Roam on 9/11/20.

Since then, as I got up the learning curve on how to use it, I’ve found it amazing. It’s evolving rapidly, so there are lots of neat new features that show up on a regular basis. There are many integrations with other stuff, and, while a bunch of them are rough, several of them (like Readwise) solved a fundamental “notetaking while reading” challenge that I’ve had since the Kindle first appeared.

I use a lot of different software.

Nothing has had as much impact on me since Agenda as Roam. I’m sure I’ll be writing about it more in the future.

And, a post like this wouldn’t be complete without a thank you to Mitch Kapor. I have several entrepreneurial heroes. Mitch is one of them. Lotus Agenda is only one thing among many that I’m thankful to him for.