Brad Feld

Tag: bitcoin

Did you sell any bitcoin (or other cryptocurrencies) in 2017? If you did, do you know how to pay taxes on the transaction(s)?

I’m going to guess that a lot of people in the US that fit in the category of having sold some bitcoin in 2017 haven’t spent a millisecond thinking about what tax they might owe. There are probably others who feel like they shouldn’t have to pay any tax because they believe bitcoin is outside the reach of the government. And then there are others who believe the theoretically anonymous elements of the cryptocurrency they are trading should prevent anyone – especially the government – from finding out about what they are up to.

Two interesting articles came out in the past week. The first, When Trading in Bitcoin, Keep the Tax Man in Mind, is an excellent overview that addresses the following questions.

  • I sold some Bitcoin last year. What do I need to do?
  • I bought a computer (or another product or service) using Bitcoin. Are there tax implications?
  • I’ve successfully ‘mined’ Bitcoins. Now what?
  • I was paid in Bitcoin. Are there any special tax consequences?
  • What if I paid someone else in Bitcoin for their services?
  • Can I reduce my tax bill by donating my cryptocoins?
  • Will I receive any tax forms from my exchange? Do I have to track my own transactions?

The second article, Why the I.R.S. Fears Bitcoin, is an Op-ed in the NYT that I have mixed feelings about. While there are a number of scenarios about how to evade taxes, it ultimately leads to a proposal:

“A smarter response would be for the government to switch from taxing income when it is received to taxing income when it is spent. Many economists support moving to this kind of consumption tax, but it would require a major overhaul of the tax code.”

The “shift from a consumption tax” from an “income tax” is an endless debate that I’ve been hearing since I first started reading Forbes Magazine in college over 30 years ago. So, while logical, it feels like you could potentially compress the article into an argument for a consumption tax.

But, I loved the final paragraph.

“More generally, cracking down on tax evasion will require that the community learn to trust government. Since this goes against the very ethos of the cryptocurrency movement, it poses the most difficult — but no less necessary — challenge.”

The rabbit hole goes deep.


My favorite Onion article of all time (from 2010) is U.S. Economy Grinds To Halt As Nation Realizes Money Just A Symbolic, Mutually Shared IllusionIt starts off with some Bernanke brilliance.

“Though raising interest rates is unlikely at the moment, the Fed will of course act appropriately if we…if we…” said Bernanke, who then paused for a moment, looked down at his prepared statement, and shook his head in utter disbelief. “You know what? It doesn’t matter. None of this—this so-called ‘money’—really matters at all.”

“It’s just an illusion,” a wide-eyed Bernanke added as he removed bills from his wallet and slowly spread them out before him. “Just look at it: Meaningless pieces of paper with numbers printed on them. Worthless.”

This is not a new idea. From William Gibson’s book Neuromancer, one of the most important sci-fi books ever which established the idea of cyberspace in 1984.

“Cyberspace. A consensual hallucination experienced daily by billions of legitimate operators, in every nation, by children being taught mathematical concepts… A graphic representation of data abstracted from banks of every computer in the human system. Unthinkable complexity. Lines of light ranged in the nonspace of the mind, clusters and constellations of data. Like city lights, receding…”

Back to the Onion article.

“Sen. Orrin Hatch (R-UT) finally shouted out, “Oh my God, he’s right. It’s all a mirage. All of it—the money, our whole economy—it’s all a lie!”

Now, ponder Bitcoin.

“I’ve spent 25 years in this room yelling ‘Buy, buy! Sell, sell!’ and for what?” longtime trader Michael Palermo said. “All I’ve done is move arbitrary designations of wealth from one column to another, wasting my life chasing this unattainable hallucination of wealth. What a cruel cosmic joke,” he added. “I’m going home to hug my daughter.”

Or Ethereum.

“A few U.S. banks have remained open, though most teller windows are unmanned due to a lack of interest in transactions involving mere scraps of paper or, worse, decimal points and computer data signifying mere scraps of paper.”

I just read Kenneth Rogoff’s The Curse of Cash: How Large-Denomination Bills Aid Crime and Tax Evasion and Constrain Monetary Policy. I literally have zero cash in my wallet. On a daily basis, I’m dealing with very large sums of money across multiple companies, but it has completely become a functional abstraction to me.

As I did a fairly sophisticated transaction on my computer yesterday that moved cash into a cybercurrency, I had the phrase “money is a consensual hallucination” echoing in my head. Math and computers are helping reinforce this. And the government is watching.


If you are interested in understanding the business implications of blockchain technology, William Mougayar‘s new book – The Business Blockchain: Promise, Practice, and Application of the Next Internet Technology – is a must read.

I’ve known William for about five years. I almost invested in his company Engagio (there’s now a different company by that name) but decided not to. However, our friendship developed and he’s been an amazing host anytime I’ve been in Toronto.

Several years ago William became obsessed with Bitcoin and then the Blockchain. In January 2016 he launched his new book effort around the Blockchain on Kickstarter and I quickly backed him at the GENEROUS Supporter level.

GENEROUS Supporter
++ 50 E-BOOKs of The Business Blockchain.
++ 50 E-BOOKs of Centerless.
++ 50 Print copies of Centerless.
++ Your Name in the Acknowledgements for BOTH books, and on the website.
++ Invitation to Slack private channel
++ 45 mins Conference Call Discussion with your team to discuss your Blockchain strategy.
You will receive the digital copies of the first book in March 2016, and the second book in June 2016.

I love Kickstarter. I have such a delicious habit that allows me to exercise my poor impulse control whenever I feel like it, which if you think about it too hard, is a little contradictory.

William ended up getting a publishing deal with Wiley (through the same editor that I work with and had connected with William a while ago.) Wiley did a great job cranking things out extremely quickly, breaking all the normal publishing time frames, and the book comes out in a week (you can pre-order it on Amazon now.)

I read a draft a month or so ago and gave William a blurb for the book, something I rarely do anymore and only when I’ve read and commented on a draft. But when a friend asks and I’ve had a chance to read the draft, I’m game to do this, like I did for Steve Case’s recent excellent book The Third Wave: An Entrepreneur’s Vision of the Future.

On Sunday, after my two hour run, I laid on the couch and read the production copy of William’s book. He’d cleaned it up a lot since the draft version I’d read and it flowed quickly. While I know plenty about the blockchain – both technically and from a business perspective – I read it with beginners mind, assuming I knew nothing about Bitcoin and the blockchain, other than how to spell them.

It’s a quick read, but has a lot of depth. William is a good writer so it’s easy to read, especially for a book around a topic that is hard to get into. As a bonus, the footnotes and bibliography are solid, giving you lots of places to go if you want to explore more.

If you want to understand the blockchain from a business perspective, this is the book for you.


If you are interested in the blockchain or bitcoin, go support William Mougayar’s new Kickstarter The Business Blockchain Books.

William is writing two books on the blockchain. We had early discussions with him about doing them via FG Press, but since we’ve decided to shut down FG Press (more on that in a later post) we encouraged William to explore different options. He chose to launch on Kickstarter, which I think is an awesome place for an domain expert like William to do this instead of going the traditional publishing route.

I’ve gotten to know William over the past seven years. I originally met him through his previous company Engagio. We weren’t investors, but I was an early and active user and fan. We get together ever time I go to Toronto and I’ve enjoyed watching him engage deeply in the Toronto startup community, while building deep expertise around the blockchain (and corresponding technologies). He also publishes a really useful blog called Startup Management and has been making seed investments in a number of companies, especially around the blockchain.

I just supported his Kickstarter. Fred Wilson did also – and wrote about it at Let’s Give William A Big Advance.

I agree with Fred – let’s support William’s new books and learn a lot more about the blockchain in the process.


A few weeks ago a I wrote a post titled It’s Not Right vs. Left, It’s Old vs. New about the conflict between innovators and incumbents. As a society, we are just starting to wander into the real structural conflict around this and I don’t believe our government, either at the local, state, or federal level, really knows what to do about it, or how to effectively engage in it.

If you want a magnificent example of this, all you need to do is look at what’s going on with Bitcoin. Actually, you just need to read two relatively short “open letters” which appeared on the web this morning.

First, read U.S. Senator Joe Manchin (D-W.Va.) letter asking regulators to ban Bitcoin.

Now, read Fred Wilson from USV’s blog post A Letter To Senator Manchin where he explains how regulatory activity in the US is already inhibiting innovation around Bitcoin, rebuts Manchin’s perspective, and analogizes Bitcoin to the Internet.

It’s probably no surprise that I completely agree with Fred’s perspective.

For disclosure, I don’t have much of a financial stake in this game – I own slightly less than 20 Bitcoins (I’ve used fractions to buy some stuff), have no intention to be a Bitcoin trader (I don’t actively trade individual public company stocks or currencies either), and I don’t have a direct equity investment in any company around the Bitcoin ecosystem (although I have several investments in VC funds who do.) I originally bought the Bitcoins for the Coursera course Startup Engineering which I managed to get through the fourth week of before I couldn’t make enough time to keep up with it. I thought I’d bought 10 but was surprised to see a few months ago that I had 20.

While I don’t have a financial stake, I have a huge intellectual and emotional stake in this. Bitcoin is a fascinating innovation. It has the potential to transform a number of different things, where fiat currencies and payment mechanisms are merely two of them. As a computer science problem, Bitcoin is a fascinating one. And, as an innovation vector, it’s a great example of “new” in a world that is desperately trying to hold on to “old.”

We are going to have a very rocky road as a society over the next 40 years. As with every generational shift, there is a lot of disruption (the 1960’s immediately come to mind.) But the amount of change, pace of change, democratization of innovation and entrepreneurship, connectivity of communication around the world, and intellectual complexity of the new innovations being created will dwarf anything we’ve seen as a species since our first moments of sentience.

Bitcoin is just a visible 2014 example of this. As Fred says at the end of his post

“When something as new and as different as Bitcoin emerges, it is tempting to want to “put the Genie back into the bottle” and protect ourselves from it. But thankfully the US did not do that with the Internet. The impact of the commercial Internet on the US economy and our society as a whole has been massive and overwhelmingly positive over the past twenty years. We should approach Bitcoin in exactly the same way and if we do, I expect the benefits we will see will be equally important, impactful, and beneficial to our economy and our society.”

My message to all the incumbents out there is a simple one. The more you try to organize and control “the new”, the harder it is going to be on society. The new is going to route around things, just like the Internet routes around things. Rather than fight innovation, embrace it, encourage it, iterate on it, accept the mess of it, and play with it, rather than against it. It’s more fun and will serve us better in the long run.


Bitcoins Bitcoins EverywhereI woke up this morning to several articles about Bitcoins. From Dave Taylor’s explanation in the Boulder Daily Camera to a paywall article that you can’t buy with bitcoins (ironic) in the NY Times (A Bitcoin Puzzle) to Fred Wilson’s blog (A Note about Bitcoin), I was surrounded by words about them.

We have an awesome CEO list that covers plenty of topics. Early in the week I posted a link to Fred Wilson’s post Buying Your Holiday Gifts With Bitcoin. That generated a fun discussion including lots of “what are bitcoins and why do I care”; “here’s what they are” kind of things. And then Kwin Kramer of Oblong weighed in with a phenomenal essay. It follows.

I’m with Seth; I think bitcoin is interesting on several levels, including as a real-life experiment with a semi-decentralized currency.

Bitcoin is a software engineer’s implementation of money (as distinct from, for example, a politician’s, banker’s, or economist’s).

There’s a lot of overlap between bitcoin fans and folks with strongly libertarian views. Many of bitcoin’s most vocal proponents see bitcoin as a currency, a replacement for currencies that are created and managed by governments. These folks tend to view bitcoin as a sort of electronic version of gold, a new currency that’s not a “fiat” currency.

I’m deeply skeptical of this set of ideas. First, and very generally, I don’t tend to think that dis-intermediating government institutions is a useful goal in and of itself. I would describe a well-run central bank like the United States Federal Reserve the way Churchill described democracy: the worst solution to the problem of managing a monetary system, except for all those other forms that have been tried from time to time.

In addition, core design decisions in the bitcoin spec make bitcoin a pretty terrible store of value and unit of account, which are two things we expect from a currency.

As has been noted in this thread, the total number of bitcoins is capped at 21,000,000. Currently there are about half that number of bitcoins in circulation. The rate at which new bitcoins are mined is designed to decrease over time. This means the bitcoin market behaves more like a commodity market than like a currency market, prone to volatility and some specific kinds of market pathologies. In my view the fact that the money supply can’t be “managed” by a central bank that is able to turn various “knobs” (interest rates of several kinds, the amount of money in circulation) is a bug, not feature!

The cap also means that a bitcoin-denominated monetary system will be a system built around deflation — the opposite of how the monetary system we use today is constructed. Over time, prices will fall, rather than rise. Economists generally view deflation as a problem. If prices get cheaper over time, all the time, people have strong incentives to delay purchases and to save money. If everyone saves, rather than spends, economic growth is impossible.

Economists have lots of tools for talking about this stuff. And, while economists often disagree violently with each other, the collective knowledge in the field is important and valuable. To draw an analogy, non-programmers can and often do have very insightful things to say about digital technology. But it’s definitely worth talking to experienced programmers when trying to understand a particular platform, protocol, or application.

I’m not an economist, but I find convincing the economists’ consensus that deflation is “bad.” At the very least, I’d argue that we don’t know how to build a stable monetary system on top of a currency that is fundamentally deflationary.

On the other hand, even if bitcoin makes for a poor currency, it may well be a very useful payment mechanism. The original bitcoin paper focuses heavily on this aspect of the system design.

To explain this a little more, we can think about how we use US dollars in normal, every-day life. I usually keep some printed dollar banknotes in my pockets. These banknotes — these “dollars” — are a store of value. (They’re worth something in an economic sense.) The banknotes are also a unit of account. (Lots and lots of things I encounter every day have prices denominated in dollars.) Finally, each banknote is a payment mechanism — a transaction mechanism. I can hand over a banknote to most people I might want to buy something from. They’ll accept it. We’ll both know what that means.

But physically handing over a “dollar” isn’t the only payment mechanism I regularly use. I have credit cards, and checks (sort of — that’s kind of changing), and now some other electronic payment mechanisms like PayPal and Amazon points.

It’s possible to separate the functions of value store, unit of account, and transaction mechanism. They fit together neatly and are systemically related, but they’re three different things.

The bitcoin peer-to-peer transaction protocol is pretty cool. It’s basically strong cyptography, good timestamps, and a consensus protocol for blessing transaction reporting.

Which boils down to a way to “hand someone cash” electronically. With no trusted third party having to broker the handover. And, theoretically, anonymity for both the payer and the payee.

As a software person, I think of this as a platform. A new electronic payment platform that may have significant advantages over most of the existing ones. To get broad adoption, platforms need killer apps. So far, there aren’t killer apps for bitcoin. But there are some possible raw materials for killer apps. Cheaper international payments. Completely anonymous electronic payments. But the great thing about platforms is that it’s often quite hard to predict early on what the killer apps might be. Particularly for the really disruptive ones.

A couple of final caveats. It’s not clear (at least to me) whether it’s possible to separate the currency aspects of bitcoin from the transaction platform aspects. If bitcoin does turn out to be a flawed currency, that could be a problem even if the transaction platform stuff is really useful.

Also, the bitcoin platform is pretty new and there may be some fatal flaws in the design of its anonymity features and its transaction log. For example, the transaction log is a global, permanent thing. To verify any bitcoin transaction you have to have a full record of every bitcoin transaction ever. That’s okay now; the system is small. Our computers and networks will keep getting faster as bitcoin use increases. But a broadly used currency will have to be able to support a lot of transactions. Maybe the design can be patched, either in a technical sense or in a social/institutional sense. But we don’t really know.

Some links:


My long time friend Terry Kawaja (history question – which Colorado-based company was Terry once CFO of) from Luma Partners sent me his latest parody video titled Use Bitcoin. I knew it was a parody of something, but I didn’t remember “Wear Sunscreen” (which I saw when it first came out in the late 1990’s) until I read the liner notes on Terry’s Youtube post.

Both are awesome. But to really grok how awesome Use Bitcoin is, you have to watch Wear Sunscreen first. It follows.

Now – Use Bitcoin.

Count me inspired. And amused.

If you want something serious from Terry, his 20 minute State in the State of Digital Media 2013 is definitely worth watching.