Ciro Santilli @cirosantilli 35

The best article available so far is: www.theregister.co.uk/2019/01/29/how_i_caught_silk_road_mastermind (archive) which summarizes what one of the investigators said in a 2019 French computer security conference.

The key living posts are:

stackoverflow.com/questions/15445285/how-can-i-connect-to-a-tor-hidden-service-using-curl-in-php (archive) which was originally asked under the real name, and then the username was changed to "Frosty", which matches one of the server's logins after the laptop was captured
altoid early Silk Road mention: bitcointalk.org/?topic=175.70;wap2 (archive)

The big question is of course how libertarian free market ideologically motivated the website was, and how purely criminal greed it was.

The magnitude of the early operational security mistakes does make Ciro think that Ross did it "because he could" and "for the lolz" in a real world Breaking Bad way.

The entry in Ross' diary does resonate a lot with Ciro and any entrepreneur, full diary at: www.wired.com/2015/01/heres-secret-silk-road-journal-laptop-ross-ulbricht/ (archive).

[i]n 2011," [I believe I will be] "creating a year of prosperity and power beyond what I have ever experienced before,
Silk Road is going to become a phenomenon and at least one person will tell me about it, unknowing that I was its creator."

Having this kind of feeling, is the greatest thing any human can have, and what motivates all great things.

Capitalizing in illegal things though is a cheat, big things take longer than a few years to reach, but reaching them is that much more satisfying as well.

Other interesting quotes:

I hated working for someone else and trading my time for money with no investment in myself.

which Ciro also feels, see don't be a pussy, and:

Everyone knows I am working on a bitcoin exchange. I always thought honesty was the best policy and now I didn't know what to do. I should have just told everyone I am a freelance programmer or something, but I had to tell half truths. It felt wrong to lie completely so I tried to tell the truth without revealing the bad part, but now I am in a jam. Everyone knows too much. Dammit.

Also very worth reading is the San Francisco flat mate account: www.vice.com/en_us/article/ae3q8g/my-roommate-the-darknet-drug-lord (archive).

The murder for hire allegations are also interesting: mashable.com/2013/10/03/silk-road-hits, he paid 80k dollars to undercover DEA agents!

Except for the fact that Ross was an 80 million Dollar drug lord, those accounts sound exactly like what you would expect from any other nerdy startup founder! The:

"just do it" strategy effectively going to a minimal viable product (manual transaction management!), while making many mistakes along the way, including hiring mistakes and successes when scaling is needed
the hardship of self bootstrapping your own social network (here with some kilos of mushrooms)
the variety of periods, from relatively calm, to hair pulling stress during big changes

It is also amusing to see very concretely the obvious fact that the FBI can get a subpoena for all accounts you ever had, e.g. they knew his laptop model from Amazon and brought a corresponding power cable to the arrest! If you are going to be a cyber criminal, don't use your real name, ever!

Should justice be blind? Maybe. But it does hurt for mere non-blind men to see it sometimes. Especially when drug liberalization is involved.