IamA (once homeless) street-performing musician whose life was completely turned around because of the incredible generosity of an absolute stranger. AMA!

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

Haha I know right... Pheweeeee.

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?

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.

What were your reasons for becoming homeless?

I graduated university with alot of debt.

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

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.

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

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.

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

What was your major and intended profession?

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.

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

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

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

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

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

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.

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?

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 www.leojamesconroy.com or if you want to just watch me now then here I am in action.

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

Thank you very much!

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

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

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.

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

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

Thank you very much for listening!

Holy fuck man. That was awesome.

thank you!

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

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.

Are you still in contact with the lady?

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

Sounds like your plan all along...

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

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

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, www.leojamesconroy.com 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.

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

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

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

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.

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.

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?

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!

Where do you see yourself in 5 years?

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!

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?

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!

What kept you going despite the harsh condition?

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.

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

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

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

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.

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

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.

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

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

Your voice is incredible, thank you for sharing it!

thank you for the kind words :)

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.

Thank you very much :)

Who are your inspirations?

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.

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.

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!

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.

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.

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.

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.

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?

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.

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

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 :)

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.

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.

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

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

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

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.

Where did you have the most fun in America?

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.

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

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

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!

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!

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

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

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?

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.

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?

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.

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.

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

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

I did! But very much so out of courtesy.

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

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.

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

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.

Did you sleep with her?

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.

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

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.

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.

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!