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My first startup actually landed me in CA state prison. (Read about my prison sentence and my new project here: http://comebackasap.com/burn_the_boats/ http://c

My first startup actually landed me in CA state prison. (Read about my prison sentence and my new project here: http://comebackasap.com/burn_the_boats/ http://comebackasap.com/burn_the_boats/ ) Though I "only" served a year, the one thing I missed more than anything --including family, friends, and the touch of a woman-- was internet access. (I love my family, friends, and lady friends but a year away from them wasn't so bad. Fortunately I have no kids.) I'd literally have dreams about the internet. One dream I remember in particular was winning an imaginary "Inmate of the Month" contest. My prize was an hour of unfettered access to the internet. It was absolute bliss checking my email, Google Voice, Hacker News, etc.) I remember that dream with vivid clarity to this day. It may seem innocuous, but to me it illustrates how we've become so accustomed to an information-driven existence. While in prison I'd seen numerous sports trivia arguments that resulted in all-out brawls that could've easily been resolved with a 5 second Google search. (Dudes were getting sent to the SHU for as many as 6 months because of a fight that stemmed from an argument over which team Kobe Bryant scored 81 points against. Insane.) So you may ask, "Why not ask the C.O.'s to look it up on their phones?" It's true, some CO's would do it for us. Others would tell us flat-out "no". But then you have to worry about the dk CO's that would pretend to look it up, then give us faulty information just to stoke the flames of discord amongst us inmates. (I've seen this happen multiple times.) As you can imagine, there is a lot of storytelling (read: lying) that goes on in prison. Imagine not being able to call a guy out on his nonsense with a couple swipes of the screen. "Oh you're in prison for moving 100 kilos of cocaine? Says here you were convicted for felony DUI." An extreme example but you get the point. In the free world, people simply can't get away with BS when each of us is walking around with miniature super-computers in our pockets. "Cruel punishment" indeed.

handelaar 13y ago
> Read about my prison sentence and my new project here Tip: In the UK, operating a fund which hedges against criminal proceedings (colloquially, a 'bust fund') is a severe criminal offence in its own right. Do reassure me that you've made very sure nobody where you are is likely to prosecute you a second time :)
- carlyle4545 13y ago
  Unfortunately there aren't any reassurances I can give you. Several code sections in CA prohibit insurance against "willful acts, wrongful acts and criminal acts." However, Comeback's goal with custodial insurance isn't to make the consequences of being convicted of crimes less severe, it's to reduce the likelihood of recidivism upon release. In a state where the recidivism rate is a staggering 65%, at a cost of tens of millions of dollars to taxpayers, we need something radical to turn things around. Over 40% of the prison population is incarcerated for violating the terms of their probation or parole. Custodial insurance is just crazy and disruptive enough of a concept to make a difference in reducing these obscene numbers. We're working diligently to garner support amongst community activists, religious leaders, and most importantly politicians in hopes of easing any potential restrictions in offering custodial insurance. Sadly there's a very real possibility that despite our noble intentions, Comeback may ultimately lead to a failed business and some very heavy fines...possibly even jail time.
  - saraid216 13y ago
    Please tell me you at least have some paid-for legal advice.
    - carlyle4545 13y ago
      Thankfully we have 2 attorneys sitting on our advisory board. Edit: That's not to say we have it all figured out by any means. I'd love to read some feedback from the HN community. Not so much legal advice, but in terms of the overall concept of custodial insurance, (an insurance policy that covers a person's expenses for up to a year in the event they get taken into custody.)
  - bramcohen 13y ago
    Low enforcement might start issuing warrants to hand over your customer list as a list of potential suspects. If I were you I'd start that rumor myself.
    - 13y ago
mahyarm 13y ago
So from what I understand from your story, if you hired the proper lawyers and put in the proper legal structure to properly protect yourself in the first place, you wouldn't of been sent to prison? Jesus
- carlyle4545 13y ago
  You're partially correct. Yes, our corporate attorney was useless. We had been under investigation for a year prior to formal charges being filed. He made a variety of changes to our contracts in an effort to make the company compliant with CA law, (mostly indemnifying us against any loss that may come as a result of a person placing their vehicles in our program.) He failed. I was sentenced to state prison. Our "proper legal structure" mattered little in lieu of the circumstances that led to the company's (and my freedom's) demise.
lambersley 13y ago
Interesting idea. What would the premiums be based on? Were you able to find insurers willing to back this business model?
- carlyle4545 13y ago
  We've developed some proprietary risk assessment software that takes a variety of risk factors like age, gender, zip code, employment status, # of arrests, etc. and calculates the likelihood of an applicant returning to prison. Based on that, we determine premium amounts, down payment, or whether or not we can write a policy for them at all. The CA Dept. of Corrections has a similar system called the CA Static Risk Assessment (CSRA) which they use to determine housing for inmates and eligibility for early release. Our algorithm uses far more variables than theirs to determine insurability. >>>Were you able to find insurers willing to back this business model?<<< Our underwriter backed out at the last minute before launch several weeks ago. We're scrambling to replace them as of this writing. Surprisingly we've gotten interest from a number of different insurance companies to offer this.

handelaar 13y ago

> Read about my prison sentence and my new project here Tip: In the UK, operating a fund which hedges against criminal proceedings (colloquially, a 'bust fund') is a severe criminal offence in its own right. Do reassure me that you've made very sure nobody where you are is likely to prosecute you a second time :)

carlyle4545 13y ago
Unfortunately there aren't any reassurances I can give you. Several code sections in CA prohibit insurance against "willful acts, wrongful acts and criminal acts." However, Comeback's goal with custodial insurance isn't to make the consequences of being convicted of crimes less severe, it's to reduce the likelihood of recidivism upon release. In a state where the recidivism rate is a staggering 65%, at a cost of tens of millions of dollars to taxpayers, we need something radical to turn things around. Over 40% of the prison population is incarcerated for violating the terms of their probation or parole. Custodial insurance is just crazy and disruptive enough of a concept to make a difference in reducing these obscene numbers. We're working diligently to garner support amongst community activists, religious leaders, and most importantly politicians in hopes of easing any potential restrictions in offering custodial insurance. Sadly there's a very real possibility that despite our noble intentions, Comeback may ultimately lead to a failed business and some very heavy fines...possibly even jail time.
- saraid216 13y ago
  Please tell me you at least have some paid-for legal advice.
  - carlyle4545 13y ago
    Thankfully we have 2 attorneys sitting on our advisory board. Edit: That's not to say we have it all figured out by any means. I'd love to read some feedback from the HN community. Not so much legal advice, but in terms of the overall concept of custodial insurance, (an insurance policy that covers a person's expenses for up to a year in the event they get taken into custody.)
- bramcohen 13y ago
  Low enforcement might start issuing warrants to hand over your customer list as a list of potential suspects. If I were you I'd start that rumor myself.
  - 13y ago

mahyarm 13y ago

So from what I understand from your story, if you hired the proper lawyers and put in the proper legal structure to properly protect yourself in the first place, you wouldn't of been sent to prison? Jesus

carlyle4545 13y ago
You're partially correct. Yes, our corporate attorney was useless. We had been under investigation for a year prior to formal charges being filed. He made a variety of changes to our contracts in an effort to make the company compliant with CA law, (mostly indemnifying us against any loss that may come as a result of a person placing their vehicles in our program.) He failed. I was sentenced to state prison. Our "proper legal structure" mattered little in lieu of the circumstances that led to the company's (and my freedom's) demise.

lambersley 13y ago

Interesting idea. What would the premiums be based on? Were you able to find insurers willing to back this business model?

carlyle4545 13y ago
We've developed some proprietary risk assessment software that takes a variety of risk factors like age, gender, zip code, employment status, # of arrests, etc. and calculates the likelihood of an applicant returning to prison. Based on that, we determine premium amounts, down payment, or whether or not we can write a policy for them at all. The CA Dept. of Corrections has a similar system called the CA Static Risk Assessment (CSRA) which they use to determine housing for inmates and eligibility for early release. Our algorithm uses far more variables than theirs to determine insurability. >>>Were you able to find insurers willing to back this business model?<<< Our underwriter backed out at the last minute before launch several weeks ago. We're scrambling to replace them as of this writing. Surprisingly we've gotten interest from a number of different insurance companies to offer this.