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Pigeon.ly, a Startup Focused on Serving the U.S. Prison Population, Joins YC (techcrunch.com)
324 points by doppp on Mar 24, 2015 | hide | past | web | favorite | 76 comments

I think this...ANY...effort to bring modern IT services to inmates/convicts is terribly overdue and applaud this effort with all my heart. Convicts (their preferred label, not mine) are treated worse than animals in many cases.

I spent 22.5 months in the Florida DOC system, and did hard time with the nastiest of them. I built out a simple single-user DB (using Access, what else?) system for the law library at Gulf CI in the panhandle that allowed lightning-fast referencing of case law and cites.

This was 11 years ago, and IT and web interest was big, but nowhere near where it is now, so I was amazed at the interest so many fellow convicts had in my work, and I tried my best to teach every single one of them what I knew and to maintain and extend my work.

It truly felt like God's work at the time.

A lot of "lifers" (people with life sentences, with no apparent chance of release) hung out in the law library, working on their cases for years, and these peoples were so grateful for the work I did...the common refrain was "no one will ever work as hard as you can when it comes to your freedom", and almost all this law library crowd knew way more about the legal system than the highest paid lawyers I've known and used.

They were hackers in the truest sense of the word.

Sometimes, it was hard to reconcile the charges I saw with the people I lived and worked with, I'll be honest, but as I used to say, one or two (really) bad hours/days do not always make a person "bad".


First, much respect to you for getting out and trying to help. I admire that a TON. Especially because i'm sure you know firsthand the difference it can make.

I'm hoping my work with Penmate (http://penmateapp.com) can help improve the library as well. In addition to helping keep families connected, we really want to improve the resources inmates have in prison, in particular books, magazines and learning resources. I'll be blogging more about it soon, definitely know what you mean here.

Hey, that looks awesome...what a great idea.

If you are ever looking for coding help with the project, please let me know.

I'd love to help with this work.

Unfortunately, it's so difficult for me to make any sort of consistent living since getting out that I have not been able to fulfill the promises I made to myself about developing systems like yours to help these almost-forgotten and totally marginalized souls, so seeing someone else doing it makes we want to help again.

From your site:

> Over 2 million people are effected by mass incarceration in the United States.

You probably mean affected.

And now... its been corrected ;) Thank you!

Planet Money just did a podcast on Pigeon.ly.


Fascinating to listen to the founder talking about the difficulty of starting a business as a former convict. Its ironic that because he was in prison he best understands the target market, however being in prison meant banks and other investors viewed him and his business negatively.

(edit: Planet Money did the podcast on Pigeon.ly, not another company)

Planet Money's podcast was about this very company -- they just changed their name. It's mentioned somewhere midway through the episode.

Oh, I must have missed that. Good for Frederick. Their new business of providing prison local phone numbers for families out of state to use was genius. That probably saves inmates so much money in long distance calls. I'd guess that the vast majority of inmates are incarcerated far from their home and family.

The concept of an expensive "long distance call" has been eradicated in every other aspect of life. It's too bad that prisoners and their families are being taken advantage of by the service providers here.

Actually that's not entirely true. There are a lot of places in the U. S. at least that still have very poor to no cell phone coverage, but do have landlines. In most of these places, calling to anywhere but the area around the nearest town is a long distance call (with a commonly 7 - 12 cent per minute charge on top of the monthly local phone access charges) -- unless you don't consider that expensive. Believe me it can add up quickly.

Yup. I just listened to this podcast yesterday it was quite good. Nice to hear about someone that made something good out of a bad situation.

Reading this just moments after shredding a prison map, putting a failed product attempt of mine on the shelf.

The idea was to provide a texting kiosk for prisoners to SMS friends and family.

Building the technology MVP to run an iMessage-like application on a tablet was the easy part. Getting prisons interested in making a few pennies per SMS - also easy.

Why did it fail? (why did we stop short?)

- The jails required hardware that, "cannot be turned into a weapon." Phone handsets are used as hammers and ripped from walls, so much that these came about http://media.columbian.com/img/photos/2014/08/25/257871_A_Po...

- Manufacturing and installing "safe" kiosks required for our app, like http://www.talton.com/images/kiosk_phone.jpg was a costly proposition.

- Internet access and power. Consider weak-or-no data signal, and ethernet & power that must be drilled through thick concrete walls.

- Existing jail phone systems with the hardware already installed are protective of their business and were not willing to put our software on their devices.

- Integrating with existing canteen systems (a prisoner's bank account) was also complicated. There aren't exactly APIs for that.

- Lastly, and I found this to be most interesting, in our discussion of beta testing with certain prisoners was deemed a bad idea, citing that those who have special access become targets for other inmates.

I loved Hutson's Shutterfly-like photo service when I first read about it, since it improved a prisoner's quality of life without introducing the technology hurdles above. Amazing founder story and product.

After my own experience, I'm even more impressed reading that Pigeon.ly is handling over 2 million minutes per month and would be interested to hear the "how we did it" story on that one some day.

I suspect Hutson's success is largely due to the fact that (from what I can gleam by the TC article) his core offerings require no prison participation at all - and certainly no hardware distribution/installation.

In fact, both core offerings have been around for quite a while as mainstream services. My family once used http://www.localphone.com to make intl calls over VOIP via local numbers. And, of course, Shutterfly and others have existed for years to easily distribute a digital photo from your smartphone in print form.

The beauty of Pigeon.ly is he's taken these relatively straightforward products and adapted them to the prison population (and their families) who may not have been as aware of more scrappy options.

In my mind, it's more a brilliant marketing and hustle play - very well done.

I've installed quite a few of the existing solutions in quite a few prisons. I think the biggest factor that you pointed out is the existing provider.

Currently, there are only a handful of major players that really offer services in corrections. They are all currently trying to turn into the Apple/Google/Microsoft of corrections. So when you are trying to offer SMS services, they already have those services bundled. Along with video visitation, commissary, grievance reporting (kites), inmate phones and just a whole list of other services.

If you are doing an application for a tablet device then you wouldn't need the steel inmate proof case. Quite a few of the current tablet solutions are see through plastic.

The best way to get your messaging solution into prisons is to piggyback on other solutions. There are quite a few companies with solutions that are running around trying to throw what they have on as many platforms as possible. The key is to build a platform and have it to where it runs your messaging app.

Another thing with some of the current messaging solutions in the corrections market is that they will charge the price of a stamp for messages.

If installation inside of a prison is another hurdle, there are companies that you can work with on that.

I was dealing with this for about 5 years and have a whole bunch more to say about the opportunities but I'll just stop here.

I'd love to pick your brain about the existing prisons you've worked with. I'm working on a new project soon w/ Penmate that I'm currently doing a bit of R&D on. If you've got time to chat, can you shoot me an email at nick[at]penmateapp.com?

First I want to put upfront that I work for Millicorp, who owns and operates ConsCallHome.com for the last 7 years, partially a competitor of Pigeon.ly

We think it’s fantastic that Pigeon.ly is going to YC. Every company that strives to help in this area helps reduce recidivism and even more importantly allows families to communicate with their loved ones. The more sunshine on the subject the better.

This has been an ongoing battle for inmates for the last 10+ years. Recently the FCC has brought rate regulation to the prison pay phone providers, but as part of that they require some pretty significant security requirements. A little much to go in here, but the declaratory ruling where the FCC allows companies like Pigeon.ly and ConsCallHome.com to operate require enhanced security to be implemented as part of the service which allows the inmates families to save on the calls. It was a four year battle against some very big companies to help get the first part of inmate phone reform accomplished, the second and final piece of reform before the FCC still has still not been ruled upon.

There are still areas and jurisdictions who are not following the FCC rulings. I hope everyone who sees this will reach out and learn more about this ongoing issue and this unfair tax on those who can afford it the least.

For more information on the security aspects, the best FCC document: http://transition.fcc.gov/Daily_Releases/Daily_Business/2013...


I know Frederick and am very glad to see that he's making progress. Many don't understand how much social disconnection to the outside world contributes to recidivism and even to social degeneration. It's a problem because its hard for the people who love these inmates to keep them abreast of their lives easily. This product is likely to change this issue in a major way.

Not to mention the exorbitant costs placed on inmate's families as well. That's the one part of the TC headline that nerves me a bit. This isn't just meant to serve the prison population -- It's the entire family unit thats grossly effected, which certainly contributes to recidivism. Change is needed.

I love seeing this problem tackled in YC! It's a personal issue thats effected my family & community as well, so much so that I've been focusing on helping try and solve it with Penmate (penmateapp.com). Seeing YC take interest in this speaks volumes, it's extremely motivating.

To the Pigeon.ly team -- If there's anyway I can help, lets get in touch. This definitely is a problem that needs to be solved. Best of luck!

Site looks really good. Have you gotten much traction?

Thanks! I spent a lot of time thinking about UX, so that means a lot (note: there's a full mobile version available at http://m.penmateapp.com) We've started allowing families to send a free letter and photos last week so that's helped quite a bit.

NPR's Planet Money podcast had a show about Hutson and Pigeon.ly, well worth listening too. http://n.pr/1FZPCvw

I really liked this Planet Money episode, Pigeonly's story is quite inspirational, both the founder's story, and the market it serves.

I liked it too. Classic entrepreneurial story of a smart founder identifying a niche, validating it, and scaling from there.

How depressing is it that the US prison population has become so large there are industries around not just the running of prisons, but the needs of the inmates themselves?

The US seems to be completely OK with locking people up for anything and everything.

If by "the US" here you mean "the US government", then yes. Otherwise, no, most people in the United States in fact do see a problem with our enormous prison population. If the prison population per capita is so much higher than it is in other countries (and it is), most Americans can recognize that this is indicative of a problem with the justice system much more than a problem with the American people.

> most people in the United States in fact do see a problem with our enormous prison population

[citation needed] because no, that goes completely against my experience.

Is your experience having meaningful conversations with Americans about the problem? Most conversations I have that drill down deeper than surface anecdote and superficial one-liners end with most people agreeing that our prison population (and its corresponding industry) is getting out of hand. This is something even relatively uneducated and ignorant people can see. I'm interested to hear what your experience includes.

My experience is people generally believe those in prison deserve to be in prison. That there are so many in prison because so many are breaking the law. That the US is a dangerous place and arrest indicates guilt.

These people also believe that crime ridden parts are crime ridden because they're full of blacks and once a few black people move into an area they needed to add and change locks on their doors because B&E's were going to go up to fuel their drug problem. That the prison population is majority black makes complete sense to them.

Is it possible that you are talking to people that already agree with you, or at lest people younger than say 40ish? Much of the above comes from people I would never choose to associate with, but through marriage and moving to a different part of the US I have been blessed with being able to listen to some absolute bullshit. Then I moved to a larger city, and heard less of it.

As pointed out above, one of the easiest ways to get votes for either party is to be tough on crime. One of the worst things you can do when running for office is to appear weak or lenient. These wouldn't be such a great go-to tactic if the population in general thought they had a runaway problem in the prison system.

And, yet, "tough on crime" politicians do remarkably well, particularly in polls on issues related to crime.

add to that that the most powerful union in pretty much any state is the prison guards union... The union's interest is obvious. Just several days ago heard on the radio about NY prison guard union opposing reform which would decrease the number of situations where juniors are charged as adults.

It's difficult to be tough on crime, but you can be tough on criminals instead and most voters don't notice it's not the same thing.

The US government is elected by its citizens, although the US President is elected via a labyrinthine political process. I haven't seen any reform to the legal system in the past decade. So even if the problem is seen, there does not seem to be any attempt to elect politicians that will do something about the problem.

Politicians are elected on so many different issues that it's really hard to get enough people to care enough about one specific thing in order to have elections actually mean something.

Fictional numbers:

90% of the population cares about Issue X, but on a scale of 1-10 in how important it is to them, it's a 3.

Meanwhile, 45% of the population cares about Issue Y, but to them it's a 10.

Issue Y is what people will choose their politicians for. It's natural selection. I still have an appendix because, while it's useless at best and dangerous at worst, it's never killed enough people to make it a threat to the survival of the human race. Likewise, people are going to vote on war, abortion, religion, economics, civil rights, etc. They care about the prison population... they just care about other things more.

Not to mention that fixing the prison overpopulation issue isn't just passing or repealing one law. It's a multitude of laws, it filters from Congress through the judicial system to the police officers. See how long it's taken to get marijuana decriminalized in just a handful of states? Now that's just one injust thing that people get sent to prison for in the US. Trying to fix the rest of them will take even longer.

You don't get elected on "reducing the prison population".

You just described the problem exactly. Instead of getting elected based on principled issues such as "America's prison population is out of control. We should reform the justice system to easier for citizens to understand", the only way to get elected is target some special interest group. You stand a better chance of getting elected on some relatively unknown issue that is relevant in a handful of people's lives than something based on principles.

The majority of Americans do not care at all about politics. Ignorance is a rational choice in the face of the enormity of the American Federal government alone. They don't care that if you started reading the Federal Register for last year today, you would die before you finished. They don't care that if you tried to be a good citizen and understand just the tax codes that apply to you, you'd never figure it out because it changes faster than you can learn it.

Pigeon.ly is a great idea.

One question though, is this the same startup that didn't pay the dev shop that built their website? Can't find those link anymore, but remember this was a big deal some time ago.

My apologies if I'm remembering incorrectly.

And this is why companies should pay ex employees and contractors in full and make be parting as painless as possible. Even if the contractor was horrible, unless it was criminal, pay in full for time, and err on the side of overpayment and a clean break.

Otherwise stuff like this gets brought up out of context, and even worse, sometimes it happens in private when someone is considering a job or purchase of product, and something like this can hurt you when you aren't even aware it is hurting you.

I'm interested to see what others say here. I commented on this type of activity over the weekend, saying you shouldn't make it public.

Now we get to watch. Does anyone care? Will all of us freelancers have to start requesting full payment, by check, upfront?

Or was this all sorted out already, and the details simply weren't posted to HN?

My contracts are prepared by a real lawyer who specialized in software contracts. They have long and detailed descriptions of how the quality of the work is assessed, what happens if it's not up to the client's standards, what happens if it's behind schedule, etc. etc.

"_____ will write software for ______ that does ______" is a valid contract, if you both sign it. The problem (and the reason that you hire a lawyer) is that it doesn't explain what happens if there's a disagreement or dispute somewhere in the process.

Pigeon.ly and the contractor both erred if they didn't sign a comprehensive contract. They both also erred by hanging their dirty laundry in a public place.

If Pigeon.ly still had a legal issue with this, I'm sure YC would have either A) not invested or B) forced them to resolve it.

I tried to open the doc for their job posting[1] before they opened it, it was locked... so I decided to look at their site.

Load the page and you're met with: "Technology products for those who need it most. Discover what Pigeonly solves for you."

Who needs it most? Hmm... the blind? Deaf? Poor? Homeless?

The only other hint (without scrolling) is in the title, another veiled reference: "Pigeonly builds technology products for the overlooked and underserved"

Is this the best way to introduce prospective customers or future employees to the product? It sounds very dispassionate for such a benevolent cause.

Consider being more direct about the goal of helping families connect with incarcerated loved ones. The current approach is something between meek and embarrassed. You need to tell people in no uncertain terms what you do, don't expect them to scroll and read to find out.

Why not just come out and say something like "Helping families keep in touch with their loved ones during incarceration"

[1] https://docs.google.com/document/d/1SCrkYMutodHHuVPOZt32fDBh...

You are looking at it from the wrong perspective. Pigeonly has a stated goal of serving more than just the prison population and the statements on their site reflect that. If you want to know more about their products then you should go go the product websites themselves[1] (that is where their customers will be looking.

https://www.fotopigeon.com/ https://www.telepigeon.com/

Good on Michael Siebel and YC (and everyone else mentioned in the article) for supporting Hutson. Companies like JPay and Securus are awful, awful businesses that prey on the families of incarcerated people.

There's a lot of evidence to that visitation and a reliable social network are key factors in improving outcomes for paroled and released prisoners, and lowering the rates of recidivism. Anything that makes it easier to maintain relationships between people in prison and those outside the prison who love them pays of a huge social dividend. We really need to reverse the trend of recent years towards making visitation and other forms of prisoner contact much more expensive and difficult in the name of 'security.'

What do they provide in phone service that Google Voice doesn't already do for free? Google will give you a local number and forward it to specific phones for free, and I don't see why someone would use a paid service over that.

They probably also do the dance of finding numbers that are unblocked. Prisons sometimes get kickbacks or have other corruption to limit inmates access to phone services.

It's often quite a bit of work for us to get numbers in the exact area needed for a particular prison. It's certainly not always as easy as picking out a random VoIP provider and picking a rate center.

Think of the demographic here. They are not techies.

Can I make money reselling GV's services? I could easily put together a system that made it very easy to set up a GV forwarding number and charge for that.

If you can find an underserved market that would benefit from such a service then yes, you quite clearly could make money doing that. I'm not sure what you're getting at.

Well, I could ask why Pigeon needed to develop their own system instead of piggybacking on GV. I could also ask why nobody else tried offering GV setup as a service, if the alleged difficulty of setting it up was great enough to create a market for Pigeon.

>why Pigeon needed to develop their own system instead of piggybacking on GV

Who said they aren't piggybacking on GV (or somebody else)? They were vague about the tech behind their VOIP. Which is what I would expect from somebody doing exactly what you suggested. They wouldn't be honest about that or they'd be telling their customers they could just use GV instead...

What they've done is found a market and figured out how to market to them. That's huge. If you can solve those problems, you could do it too. Not every business has to make a huge technological leap to be successful.

Why nobody else tried offering an existing solution to a new market? Is that a serious question? That exact thing happens all the time and has made many companies very successful. Hell, the site you're on right now isn't exactly revolutionary (user-content link aggregator with commenting system), but it found a target market in technically minded people and it has brought value to those people. Would you ask why people use Hacker News instead of Reddit or Digg?

And I don't know if they did develop their own system or are wrapping an existing VOIP solution, I didn't see it mentioned specifically.

It sounded like they were using their own system.

If a new site opened up that offered exactly what Reddit does, but wrote their own code from scratch, (and charged), I would also ask what they're bringing to the table over Reddit, what features they have that reddit doesn't, and would criticise them for not reusing old code that did what they wanted if they couldn't show me any better features.

I guess I'd ask again, do you critique Hacker News for this?

It is definitely not a new idea to reuse existing ideas, even if you don't reuse existing code, to provide previously unserved/underserved markets with already existing services/products, nor is it a new idea to charge for it. I honestly don't know what you're getting at. Do you think they should provide this service for free because others do? Should customers just be smarter and know that Google Voice exists? What exactly do you find is wrong about this situation?

Main reason is that GV is not secure according to the FCC ruling on prison pay phones. To be used with inmate calls a phone system has to have certain security items fulfilled and processed.

GV numbers are generally blocked by the pay phone providers and the FCC has allowed that.

About a couple years ago, the NYT published this fascinating article about Sendapackage.com, which it billed as "The Cellblocks' Amazon"


Sendapackage was created by a former inmate, and its story struck me as a great example of a promising niche that is in plain sight, yet only a member of that niche would go through the work to make it a business:

> Though it might surprise many who have no experience with prison, sending packages to loved ones doing time can be, as thousands of local families know, a Kafkaesque process. Beyond the hassle of going to several stores to assemble a package, and then having to take it to the post office or UPS, is navigating a welter of rules governing what is allowable.

> The New York State Department of Corrections and Community Supervision publishes a list, currently more than 20 pages long, of who can send what, and how, and what is permitted and what is not. Food cannot contain poppy seeds; emery boards must be “nonmetallic”; boxer shorts and briefs must be of a solid color only.

> “I thought there had to be a better way,” said Chris Barrett, Sendapackage’s founder, who seems to have discovered that way on the Internet. The items that Mr. Barrett’s service sells online (as well as through its catalog) have all been chosen in advance to adhere to the extensive directives put in place for gifts by the corrections department. His selection is comprehensive and diverse enough that the company bills itself as “New York’s inmate superstore.”

Not taking away from Pigeon.ly's announcement, just happy to see another business in this underserved, neglected niche (not sure how sendapackage.com is doing as I've never yet had the need to use it)...any service that makes it easy to navigate the data of the prison system is an overall net benefit to the public, as it impresses the need upon the system to provide this data.

Edit: to reference another NYT article: "Out of Trouble, but Criminal Records Keep Men Out of Work" http://www.nytimes.com/2015/03/01/business/out-of-trouble-bu...

Given the lede paragraphs of the OP, I thought Pigeon.ly would also deal with the problem of getting released inmates onto their feet and connected to jobs and resources...that seems orthogonal to their current products but seems like it could naturally grow from their network of inmate/relative contacts.

I like this. I would love to see it expanded to work for migrant families (maybe also a less extortionate method for sending remittances back home) too.

Depends on where they want to send the remittance to. You're not going to get that for places like Somalia.

Why not? Somalia already receives $1.3B/year in remittances, so clearly it can be done. Maybe it's already as cheap as it can be, but maybe not.


True, but Central America is a good place to start.

I am TORN because I love that YC is funding African American founders. I love the traction that the company has and that the team is solving a real problem. BUT I hate how it feeds into a stereotype that all black men are criminals. It is exhausting how hard we have to work to get others to see blacks in a different light.

How do you feel it feeds the stereotype

The article has the black CEO, Frederick, dressed in all black with gold chains and talks about him selling drugs. The article leads with the stereotype and not what makes the company unique. I believe we need more positive images of black men. Again, let me say I love the work that CEO and Pigeon is doing but I do not like they way this article portrayed him because it is perpetuating the stereotype that all black men are drug dealers and thugs.

I didn't see the image, thats helps me understand what you meant more, I see. I'm particularly sensitive to this because as a "young black male in tech" myself i've had to navigate around some the bias, though when I read the article I didn't get the feeling it added to the stereotype. I am excited to see YC involved with more minority founders though, so TC article aside, hopefully this leads to more.

A lot of it seems to come from the man himself:



It doesn't give the press a free pass, but the consistency with which those articles mention the prison time does at least suggest that pigeon.ly is embracing that angle when they deal with the press.

The article touches on it a bit, but I wonder what kind of value a company as mature as Pigeon.ly is going to get from YC.

Not saying it'll be lower than others, just probably different.


Just to be a pedant, you are talking about Registry of .ly cctld. Their registrar is a separate provider with a contract with the registry.

I'm not a fan of abusing ccTLDs as generics, although in the case of .io I'm willing to make an exception since Indian Ocean Territory isn't really a country.

He has a specific gripe about this because of an adult-themed website that lost its domain registration, since Libya is an Islamic country and the registrar adheres to a different set of cultural standards.

Yeah, I personally think using .LY is insane for a lot of reasons, including that.

I'm annoyed by .co, even, though.

DNSSEC makes the problems with misuse of ccTLDs even more apparent.

This is a good reminder that tech is about improving people's lives, not the latest NoSQL-Node-React-NextShit-OMGYouDontUseThisYet. Sometimes I need to remind myself.

Remember meeting these visionary founders a few years ago. Great product. Looking forward to seeing what will happen after YC. :)

It has been a little bit crazy over the past couple of days but I just wanted to say thanks for all the support. - Frederick.

Glad to see this news, Fredrick. Keep pushing!

now, someone just needs to submit a pull request to stripe for accepting cigarettes as payment.

I love this concept!


Video conferencing is a premium product and a big money maker for them. The hurdle comes from needing someone to monitor the video calls while they are on them. So video calls need active monitoring while voice calls are more passive.

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