My short bio: Was homeless, playing on the streets in York, England and was heard by a passer-by. Six weeks later, just as I found a home, and after we had spoke for all of a couple of hours on fb, she flew me out to America to play some shows. The ten day trip turned into six months. During that time I played a bunch of shows, was invited to The Grammys (and afterparty!) and swapped my guitar once held together by sellotape and coke bottle caps for a beautiful electric guitar (60th Anniversary Telecaster). I've since gone on to play for the BBC and gotten interest from various major labels, and am setting up my move to America now. She gave me a chance, and had absolutely no reason to. For that I am eternally grateful and I'd love to tell you more about the journey so far! I'm off to bed now so will reply what I can tonight and the rest tomorrow. My Proof:

EDIT: More people are engaging in this than I anticipated and many of you are asking who I am and what I do. Well, my name is Leo James Conroy and here I am in action. If you want to know more visit my website I guess:

EDIT: To clarify the homelessness situation, as some are throwing needless accusations: I was without a home for 3 months, and I slept rough for around 3 weeks. I know I didn't have it as rough as many, or for as long as many, but I was on the streets in an old sleeping bag, sometimes my soft guitar case too, and making ends meet with what I could get from passers-by on a daily basis. I was lucky enough to be performing for my change, and to perform in people's houses in exchange for a room for a night or two. It sucks, but many people are happier to help if you don't look like you're begging. If the title is too misleading or offending, I am happy to change or delete the post entirely.

EDIT: I have been on here for hours now but I cant keep up with you all. It is 7.20am now and I must get to bed. I'll get back to you all tomorrow. Thank you for all the questions. And to those of you giving me shit for no apparent reason; grow up.

EDIT: Holy damn. Front page. I cant keep up with you all but I will do my best. Thank you for your interest all.

LAST EDIT: I would just like to say thank you for all the attention my video is receiving and for all your kind words. I really recommend you support Samsara Sessions YouTube channel: . They are a fantastic team and they work with so hard with many wonderful musicians. I owe them a lot. Thank you reddit. I was NOT expecting this to blow up but its been a good ride. I'll answer as many more as I can.

Comments: 924 • Responses: 68  • Date: 

jabs811005 karma

Can you imagine if you had learned piano instead of guitar? Imagine having to carry one of those around...

lejaco455 karma

Haha I know right... Pheweeeee.

Rito_jail522 karma

Hey - your story sounds really cool! looking forward for more details.

  1. What were the reasons for becoming homeless?
  2. What was your best/worse experience while you were homeless?
  3. Can you tell something about the passer-by? What was she(right?) doing on England.
  4. Did you have regrets before you actually flew over?

lejaco657 karma

Hello there.

  1. I graduated university with a lot of debt. My family are very dysfunctional, and coupled with issues such as bankruptcy, prison sentences and other deep personal info it was not a place I wanted to go back to. With the debts I have, and the income I was on as a musician and other side jobs, my income fluctuated weekly but was really very low. Because I didn't have a steady income, landlords were uninterested in my application, as York is a very desirable place to live and there was always somebody wanting a house who had the safety net I didnt. I stayed with friends for as long as I could, but when that couldn't last I took to performing in peoples houses in exchange for a place to stay. It was actually a really cool experience. I didn't have it as rough as some people I met and I'm eternally thankful for that, and for the power music has to connect people.

  2. Like I say, I didn't have it as bad as some people. Not at all. In fact now I'm questoining myself if saying 'homeless' is misleading as I only had to actually sleep rough for around three weeks of the three months. One night I got all my busking money taken, clothes and sleeping back pissed on, took a few punches and was about to have my guitar smashed up before anyone stepped in. I dunno, because I was young and in a heavily student-populated city I think people just thought I was a drunk student most of the nights they saw me. Best experience is what this AMA is about.

  3. She is a successful business lady from Las Vegas, Nevada. She was visiting her (then) boyfriend in London, and he suggested they take a trip to York for the day, where they then bumped into me.

  4. I have no regrets. None at all. Things are better with my family since I have been gone and come back. It's been a blessing.

i_can_verify_this812 karma

What were your reasons for becoming homeless?

I graduated university with alot of debt.

Oh boy... My future doesn't seem so bright.

OwlHarrington226 karma

UK student debt is pretty much the kindest debt imaginable, you don't pay a dime until you're earning above a set threshold and then it's taken as a percentage of your earnings. Also if it's not paid off after a certain period it's written off.

Porridgeandpeas53 karma

I'm assuming he graduated with student overdrafts from banks, which are real loans. They will give you thousands in overdrafts and credit cards as a student even if the actual student loans are easy.

Ultimately it's down to money management, but if you make a mistake at 18 you could end up paying for it the whole way through uni.

Source: have crippling student overdrafts and credit card bills haha

lejaco91 karma

This is me. People messaging me questioning my finances isn't cool man. I had to take loans out all over the place to support various people throughout my time at university. I dont want to talk about my issues with family or money though, this post was for the power of music and charity.

lejaco46 karma

haha, well there was a lot more to it than that, but yes. It didn't help.

optogirl31 karma

What was your major and intended profession?

lejaco63 karma

I graduated in Music, I was a jazz trumpeter and I conducted orchestras/brass bands. I wanted to be a teacher but then this took hold.

ADHD-PI37 karma

Huh, we have four mutual friends on Facebook, two from the York Brass Band... Which year did you graduate?

lejaco35 karma

2014, amigo! And I was the conductor of the brass band for two years :)

shahnick349 karma

hey leo it's Nick from brass band. proof: you wedgehead filthy clopper

lejaco317 karma

Nick! You introduced me to reddit. Crazy this isn't it?

ImBored_YoureAmorous309 karma

I'm sorry if this is rude: Who are you? Where can I listen to your music?

you should really put that somewhere in your post

lejaco303 karma

Hey that's not rude at all and thanks for commenting! To be honest I posted this more to focus on what a brilliant woman this lady is, and to show how music can really bring people together. I guess I've missed a trick there though as a few people have asked that. I wasn't expecting even five replies so hey ho! I'll add it now as an edit.

ImBored_YoureAmorous95 karma

Hey, no problem man -- glad you're getting your big break.

As I"m sure you know, reddit can be an unforgiving place. Hope the assholes aren't bringing you down.

But still, I'm really not trying to sound rude, but I still don't know who you are, how to get your music, and now you've introduced a 3rd variable, the brilliant lady. Who is this brilliant lady? I need answers, my friend! I live off of answers! You don't me to be homeless too, do you?

lejaco226 karma

My sincere apologies amigo, it's 5.15am here so I'm not all there in the head right now. The brilliant lady is the passer-by that heard me and flew me out to the states to stay with her and play some music. All I can tell you is she is a successful business lady with a big heart. And who am I? Well I am called Leo James Conroy, and you can find out everything you'd ever need to know on or if you want to just watch me now then here I am in action.

bexyrex145 karma

Jesus fuck your voice is orgasmic. It's so airy but gritty ah damn. You could actually make a groupie out of me lol. I hope to hear you one day beyond this internet anonimity

lejaco64 karma

Thank you very much!

UF8FF64 karma

Jesus you're the next Jeff Buckley. I bet you can swim though

lejaco72 karma

Thank you so very much and.....ouch. I can,

UF8FF27 karma

Yeah. rough go for that one, haha. But really, you're great. If you have Forbidden Fruit somewhere I can purchase it, I would love to rock to that track tomorrow at work. Otherwise, I eagerly await the release! Thank you for your contribution to the music community. Bravo.

lejaco43 karma

Not yet my friend, but in a couple of weeks it'll be out. I'll update accordingly.

SwedishGrizzly28 karma

Wow, just wow. I don't think I can put into words how much I loved that song. Truly amazing work my friend.

lejaco17 karma

Thank you very much for listening!

Thatseemsright27 karma

Holy fuck man. That was awesome.

lejaco13 karma

thank you!

Devonic9616 karma

Your own website, not a bandcamp page? This feels so foreign to me.

lejaco18 karma

Hey, I know what you mean. I used to have a bandcamp but the only music I had out was released under my friends label and he had an online store so it was just more efficient that way.

DrDolphinrider201 karma

Are you still in contact with the lady?

lejaco542 karma

Absolutely I am. I'm even dating her niece now!

SnowGryphon389 karma

Sounds like your plan all along...

lejaco215 karma

haha, no not at all, not even slightly. I was only meant to be in the country 10 days!

_o_b_106 karma

Hey your song Forbidden Fruit is amazing. When can we expect to hear more of you? Got an album coming out some time?

lejaco70 karma

thank you very much! I have an EP coming out in a few weeks which is exciting. You can find out more about me on my website, if you'd like. I also have an older EP out, but I recorded that in 2012 and my voice has matured a LOT since then. But it's there if you'd like it.

altered_state12 karma

What shoes are you wearing in the main pic on your website? I like your style.

lejaco47 karma

I have no idea, I picked them up at one of those thrift store things in Texas. Sorry! $10 though...yes.

altered_state19 karma

leo's cover is 10x better than the original by j cole, so impressed

lejaco19 karma

I too just googled that. Well played.


That sounds like an amazing story. Have you got any pics of the old guitar? It must have a ton of stories behind it.

lejaco102 karma

Hey there, my guitar is stored at the house of the people who first took me in! I'll get them to take some snaps hopefully tomorrow and get back to you! The only pics I have don't really show the damage too well, as I didn't really want to broadcast it at the time.

taway_curious72 karma

Hi Leo. That is an inspiring story. These days how do you react when you see talented, perhaps homeless, musicians playing on the streets? Do you feel like helping them out, and paying it forward?

lejaco135 karma

Absolutely. I am humbled every single day by the beautiful, freak circumstances that got me on my feet. I always give what I can to anyone on the street, musician or not. If I don't have money I do my best to give them my time. Not to sound patronising with that, it's just street performing is an incredibly lonely 'profession'. You see thousands of people pass by you every day and most never register your existence. A friendly 'hello' or 'great chops' doesn't cost anything and does so much for the spirit, especially in the cold English winters!

I_say_no_alot60 karma

Where do you see yourself in 5 years?

lejaco165 karma

I'd like to be a dad who gigs enough to provide for my family, but isn't on the road so much that I miss out on being there for them. That's my ideal. Realistically, I see myself doing exactly what I'm doing now - gigging, teaching and just making sure I do what I do for the love of music, and not the want of money. Who knows. If 12 months ago you said I'd be where I am now, and done what I've done, I'd never have believed you. Five years...we shall see!

rw2041 karma

Wow that's amazing! I hope you plan on paying it forward!

How much could you bring in by street performing in England? Did you ever get anything else besides money?

lejaco47 karma

Thank you very much. Wow, busking as we call it, now that's a question I just cannot answer so easily. There are so many variables that can affect your income. These main ones are: your location, the weather, how long you play, how loud you are, your song choices (demographics must be observed), the time of the year...there is so much. But it varies, I've made not a single penny for hours of work before, and other times I've made hundreds in a couple of hours. I'm sorry I can't be more specific but if you'd like to know more about the world of busking I'm happy to answer!

windsisu40 karma

What kept you going despite the harsh condition?

lejaco123 karma

Good question. Playing in the freezing cold winds is horrible. I couldn't feel my fingers, my toes, my voice was disappearing. More than anything it was my determination to prove I could make a living from my music, even if it was the smallest most difficult living. But you know what else helped? The architecture. York is a beautiful, beautiful place so full of history. A lot of the time I got depressed, I looked around and imagined how much easier I still have it than the Tudors, the Romans etc. I escaped into their world a little and it really made things easier. Weird I know, but it worked for me.

Snotpuff32 karma

You got chops man. Thanks for sharing. No real question just wanted to tell u that. What's your favorite taco?

lejaco35 karma

thank you for the comment! My favourite taco...Um, I didn't really like them :( sorry!

bladeofire28 karma

Where are you living and what does the immediate future hold for you?

lejaco61 karma

Hey, at the moment I'm living in Manchester, UK, but I'm hoping to be moving to LA by the middle of 2016. The immediate future, well, at the moment I'm just playing as many shows as I can and trying not to get screwed by this horrible, horrible industry. I'm in talks with various labels and agencies...I'm taking it easy for now though. I don't want fame, just enough success to make music for a living.

rjupp2424 karma

Great story! Is there anywhere we can hear some of your music?

lejaco47 karma

Absolutely. I'm currently working with a great bunch of people who are shooting some lovely videos. Here I am live singing some bluesy music, and here I am in a more intimate setting. I hope you like the songs.

Wizolsd18 karma

This is absolutely incredible. I love your new guitar by the way! Telecasters are my favorite. Can't wait for an album to drop.

lejaco13 karma

Thank you. Yes she's a babe isn't she? Hehe. Thank you for the comment.

170L14 karma

Your voice is incredible, thank you for sharing it!

lejaco10 karma

thank you for the kind words :)

Goliath_Gamer10 karma

No question here; just wanted to congratulate you on your recent success and say you sound like a very humble and talented guy. I wish you the best.

lejaco6 karma

Thank you very much :)

BROWN-5218 karma

Who are your inspirations?

lejaco32 karma

Musically speaking, my idol is Jeff Buckley. My inspiration is to one day give others that feeling of sheer bliss that he has so regularly given me.

Anthoz14 karma

Dude, you actually strongly reminded me of him on that live bluesy vid. I'm a huge J Buckley fan and I wish you the absolute best.

Can't wait to hear more. Please let me/us know when an album drops.

lejaco15 karma

thank you so, so much. I owe an incredible amount to Jeff Buckley and it means a lot that a fellow fan can hear his influence. Album will drop in a few weeks but sure I'll update!

i_can_verify_this18 karma

Who is the woman that helped you out? By that I mean what was her occupation? She had to have some kind of connections to help you get to where you are now.

lejaco23 karma

She is a business lady, but not remotely connected to the music industry. I am not anywhere big or majorly successful right now, not at all, I'm just in a better place than I was through crazy circumstances. She just has two neices who loved my music and worked very hard to set me up with some shows - and then I met people at said shows.

SSDD_P2K17 karma

I live in NYC, where there are many people who are homeless. Your post made me extremely emotional because this hits close to home. I was not, nor have I ever been homeless, but someone very close to me has been close to homeless in the past.

That being said...

1) I want to know from your opinion what I can do to help those who are homeless. What's the most beneficial thing I can give to them or buy for them? If the number one thing is food, how can I assure them I haven't tampered with the food (as some homeless people have rejected food from me for this reason)?

2) When you were homeless, what helped you to keep going? How were you able to take life one step at a time, one day at a time? I'd imagine it took a toll on you psychologically, never mind physically.

3) Maybe this first question doesn't need answering, but did the actions of kindness from strangers help you remember that better times were coming? Did you hold on to a memento or something special (a key chain, coin, etc) as a memory to keep you comfortable when things got rough?

Thanks for taking the time out to answer me, if you get to my post. Congratulations on your success. You've come far and I hope to see and hear more of you from different places. Your story is inspiring, not just for those who are in the same situation you were in, but for people who are feeling down and need a reminder that better times are always on the way-- no matter how large or small that first step is.

lejaco18 karma

Thank you for the comment. Before I answer I'd like to really really stress that I was lucky. As bad as it sounds, I made more than fellow homeless people who were just sitting and begging. My situation was masked behind blues and folk music and people were happier to give me their coin. Although I didn't make much, I was still better off than most and I felt guilty for that at times. But, my whole three weeks rough taught me a couple of things:

  1. The most beneficial thing you can give is time. To speak with us on a level, without pity. Engage in conversation, even for two minutes, ask where they're local to, what their interests are. You'll find tha goes a long, long way. I guess from there you can make your own mind up as to whether money, food, coffee is best.

  2. Music kept me going, and so did the desire to not let my close family know what was going on. As far as they were concerned I was doing gigs around the country or staying at friends. Working hard to find wifi and make out everything was fine on todays ever present social media culture. That was my side task.

  3. Yes, the kindness of strangers has always been at the forefront of my mind. It would make my day when people came just to say hello or ask how I am. I never held onto anything physical, just kept keeping on.

oinkpigrock16 karma

Hello there! What a cool story, I'm so glad you've been successful. My question - what's the strangest thing that you've seen or experienced in the US compared to England?

lejaco31 karma

Thank you. As an Englishman the thing that nearly KILLED me with laughter was when it came to making coffee. I've never had a coffee machine so I had to go buy a kettle. The people I was staying with stared at it in amazement, asking 'what the hell is that contraption?!!'. It's a kettle! It boils water! Meh, boring I know but it really tickled me.

Flyadastra14 karma

That is so inspiring! What song were you playing/singing when you two met?

lejaco42 karma

I was singing Amazing Grace, and she is an angel for sure. I know she filmed it, so I will do my best to see if I can get the video from her (if she still has it) and I'll post it on here if I do :)

Beef503012 karma

How has your family reacted with your success? Has it had a positive or negative effect on them?

Great journey man, you worked hard and have really used the opportunity wisely. Keep it going brother! You stuff sounds pretty rad also.

lejaco20 karma

Thanks for the comment! It's been good. My family have some real issues, but it's been a good middle ground. Members of my family who never used to speak now meet up at my shows and that's just great. Music is a powerful force! But yes, so far it has brought us closer.

SausageZilla12 karma

Did you ever get to speak to the guy who sleeps down Lendal next to robson and cooper and banks music room?

lejaco13 karma

The dude with the long brown/blondeish hair who is always reading a book?

HolyCrapf10 karma

Forbidden Fruit was awesome. Any plans down the road for playing in the US? (Seattle area specifically)

lejaco9 karma

That's very kind of you, thank you. I'm coming to LA for a good few weeks as of the end of November...I know that's far but that's where I'll be, stateside.

shennenali9 karma

Where did you have the most fun in America?

lejaco22 karma

ooooh tough question! I did not like the fake nature of Vegas, but I did jump off of the top of the Stratosphere Tower(830ft) whilst screaming and plugging one of my CDs into a GoPro camera. Hehe. That was fun! in fact, here is the video.

buttpincher8 karma

Dude... Can you post some links to your music?

lejaco9 karma

Hey there, I've posted it in the main description now. Hope you like.

barscarsandguitars8 karma

Are you attempting to be a solo act, or are you trying to be part of a backing band?

PM me when you get a few free mins. I'd love to link up and share some stuff with you!

lejaco15 karma

I consider myself a solo act yes, though I studied Jazz trumpet at university, so I'm happy to jam along with anyone when the opportunity arises!

spudtatoe6 karma

This is amazing! But just curious, why does it say Facebook user? Rather than the name?

lejaco10 karma

Thank you :)"she deleted her Facebook account a while back, that's just what fb does to deactivated accounts I think as it also says I cannot reply to it

theyawny3 karma

Holy crap, you have an amazing and, probably more importantly, really unique singing voice/style. Wish the best for you and hope I have the opportunity to buy some of your music soon!

I don't really have a real question. Umm, why did you choose a Tele (I have a CS Tele that I'm nowhere near good enough to justify owning) and what's your best advice for learning fingerstyle?

lejaco4 karma

Thank you very much! I chose the tele because my idol Jeff Buckley played one, and this one has such a distinct and warm sound when I'm playing softer stuff which I usually do. It's just a great, versatile instrument. And I'm afraid I can't give you any advice for fingerstyle, I taught myself so I could be doing some killer no no's! I just listen to a lot and try and copy. I'm nowhere near as good but I love listening to Andy McKee.

lurkeydurkey3 karma

This is brilliant, nice one man! All the best to you in the future, hope everything goes well.

Was there ever a point where you started to fall out of love with music and question whether what you were doing was worth it? Especially on the long days where busking yielded no income?

lejaco8 karma

Thank you! Believe me I did. In my darkest days it was horrible. Like many people, and many musicians too, I had issues with depression and having absolutely no safety net and lots of debt really put me in some real shaky places. I came close to selling my instruments to pay my debts and giving up music completely to work at the next job I could find. The long days were horrible. I would sit and listen to Jeff Buckley's masterpiece of an album, Grace on my phone and just cry in the middle of the street. I'd cry at how bitter the music world was in taking him so young (he died at 30) and I'd cry at how beautiful it was and I'd cry at how I had no money to eat again and I'd just cry for the hell of it. But in the back of mind I always remember the twinkle in my Grandad's eye when he knew I wanted to be a musician. 'Music feeds the soul, and if you're not gonna feed yourself you may as well just lay down and die'. It always made me think, and it was true. For me, music is all there is and all there ever has been, so I could whine about it or make it work.

VeryTalentedArtist2 karma

In the forth pic of your proof you are sorry about the way you use cutlery. What's wrong? It looks like you're doing it right.

lejaco2 karma

I found out afterwards you're meant to eat them with your hands...

VeryTalentedArtist2 karma

Oooh, did you finish that meal? Looks like a lot of food.

lejaco2 karma

I did! But very much so out of courtesy.

badtradesguy0 karma

Cool story, but why werent you looking for work? Min wage jobs are pretty plentiful.

lejaco1 karma

Believe me I was. I didn't get anything. Such a huge student population in such a small city, it's a nightmare, and like I say - I was rough for three weeks, I was covered the rest of the time so I got by.

janomf-3 karma

I assume fb is Facebook. How does a real homeless person have the means to chat on fb?

lejaco13 karma

Hello. If you read the post, she got in touch just after I had found myself a house, a flat share/lodging with a young couple and their daughter. I wasn't homeless for too long, around 3 months. I had fb way before shit hit the fan and I ended up with nothing. And you'd be surprised how many 'real' homeless people have facebook, btw, especially people in the hostels.. I was only 21 when it happened to me, and much of the time I was able to maintain a semi-normal lifestyle as I would put on gigs in peoples houses in exchange for a stay for a night or two, so i managed with what I could.

chris101010-8 karma

Did you sleep with her?

lejaco13 karma

Whenever I tell this story, there's always someone who asks that, haha. Sorry to disappoint, but no, I did not. ...But I am dating her niece now! I've been so lucky with the music side of things, but honestly, the highlight of the story so far is being fortunate enough to have met someone who completes me like she does.

Marchosias777-37 karma

"homeless' is misleading....But it sure makes great clickbait doesnt it?

lejaco15 karma

It is and it isn't. I was without a home for 3 months, and I slept rough for around 3 weeks. I know I didn't have it as rough as many, but I was on the streets in an old sleeping back, sometimes my soft guitar case too, and making ends meet with what I could on a daily basis. I was lucky enough to be performing for my change. People are happier to help if you dont look like you're begging. If the title is too misleading or offending, I am happy to change or delete the post entirely.

yoooooohoooooooooooo11 karma

If you felt like you didn't have a place to call home (store your belongings, take a shower, etc.) then YES, you can definitively say you were "homeless". Dang trolls always trying to stir some shit up. Keep up the greatness - I watched the music video you posted and you've got a really awesome musical style.

lejaco11 karma

I'd also say sleeping in a gutter and getting pissed on constitutes that too, but hey, it was only for three weeks so that doesn't count, right? Edit: PS thanks, glad you liked it!