Back to the Future–Revisiting My 2014 Article on Bitcoin

I wrote an article for an arcane financial journal at the end of 2013 which was published the first week in January 2014, discussing the necessary hurdles for Wall Street acceptance of the technology. It was scoffed at by all sides–first, by Wall Street, for all the reasons Jamie Dimon still harps on; but more interestingly by all of the bitcoin loyalists. It became the #1 most read article in that journal, because someone, somehow posted a link to the

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The Story of FutureEngine

A few of you have asked me about that secret, stealth startup I wrote about wanting to “commission”. Commission is probably the wrong phrase. It’s more like a sperm donation. I wanted to play a role at the conception, do none of the hard work, but still consider myself family. And I’m happy to say FutureEngine is not only born, it’s already crawling and will soon enough be running around full speed.

I don’t want to talk too much about … Read More

Introductory Syllabus for CryptoCurrencies and the Blockchain

(This post is specifically being written for my old friends Dan and Mark. They are both institutional money managers and are deeply familiar with the capital markets, having transacted many, many $billions in securities. But they are newbs with regards to cryptocurrencies. This post is specifically for them, but hopefully can be helpful to anyone wanting to seriously learn more.)

As promised at dinner, here’s my guide down the rabbit hole into cryptocurrency and blockchains. OK, I’m going to suggest Read More

I Can’t Quit You


Oh, startups. I am trying my absolute hardest to stay retired (this is the third attempt.) I know it’s wrong to keep at it, but I still feel the forbidden urge. My head tells me to “Do less, slower”, but…

The First Temptation: Ethereum

I have seen the future of fintech, and it IS distributed ledger technology. And Ethereum’s smart contracts are the key component for all payments. Accordingly, I’ve picked up the .eth domains for several hundred words, … Read More

My AMA at

Now that I’ve retired for the third time, (and am hoping this time it sticks), I think I want to get back to writing more. But for me, writing and editing is a huge pain, and I don’t like to edit. So I believe instead I’m going to do more stuff like interviews, AMAs, publishable chats, which are more fun…and certainly a little more sloppy and less edited, in keeping with the “Insufficiently Edited” concept.

My plan is to do … Read More

Tech Heavyweights Weigh in on Boston

A few years ago, I filmed a few of the leading lights of Boston Tech talking about the startup community here. Special thanks to Ahmed Hentati (who also did the initial work for the Boston VentureMap) for having archived the video. The video is old, some job titles are out of date, but the big themes: talent, tech, universities, and community are all still valid.

With no further ado, here’s Katie Rae (The Engine, Project11, Techstars), Eric Paley (Founder … Read More

Followup Comments on the Ultimate Startup Knowledge Base

Before I try to attack the next topic in the series—networks/connections—let me point out a few of the comments I’ve received offline on the last post. If you haven’t read that, read it first.

You’re back? Great. In no particular order:

*Excellent wiki efforts exist now to be copied/improved upon.  Specifically, there already is a good workflow and precedent established on GitHub for open-source guides, including this one on equity compensation. A new one is just forming to … Read More

The Ultimate Startup Knowledge Base

In “The New Virtual Accelerator”, we posited that all of venture can be broken down to knowledge, networks and capital. Today we focus on the first leg of the stool, knowledge. The problem is not that there is too little startup information publicly available–quite the contrary. The big problem regarding online resources are discoverability, quality control, maintenance, and to a lesser extent, access. This piece will not focus on those pieces of knowledge that you rent (e.g., legal services), … Read More

The New Virtual Accelerator

The early stage venture environment has changed enormously in the last 10 years. It has never been easier to start a venture and access seed capital; nor, arguably, has it been harder to separate ahead of the pack in the overcrowded startup world, which may have reached Peak MicroVC and Peak Accelerator. Seed only funds barely existed ten years ago, but now number around 300. Likewise with accelerators, which have gone from single digits to over 1000 in the last Read More

Why Demo Days Have to Change


I’ve attended dozens of Demo Days at 9 different accelerators. But this past Friday was my most comfortable one ever. And I didn’t even have to show up.

Thirty years ago, every Wall Street firm sent out their own research individually to investors. Investors hated the pile of reports, and the firms hated maintaining all the mailing lists. Then came a startup named FirstCall, which bundled them all together, coordinated the release of materials and let the investors choose … Read More