Awesound

Feb 2021: I've started to add milestones here. I'll add more if people actually read and enjoy/care. I'm starting in 2014, 15, 16 and will add more to catch up with the present day. I'd recommend scrolling down and reading in chronological order.

This could be fun!

After interviewing for YC, I go to a bar and drink for several hours with SF friends, while I wait to hear from YC.

YC said they'll email ("Sorry") if you don't get in, or call you if you are accepted into YC.

I had interviewed with YC once before (six months prior), and I got the email… so I hope my phone rings this time.

I've flown to California from Ireland for the interview. I've given them a virtual US number (you have to give them a US number), so I try to make sure I have WiFi to actually receive the call. I occasionally check my email in between pitchers.

Bummer. I see a new email from someone at YCombinator.

But I don't get a "yes" and I don't get a "no".

They like my enthusiasm, and they're doing a new experiment called the YC Fellowship. They'll write a $20k check. They tell me this by email, so I've been programmed to think of it sort of as a "no". But hey, it's YC, and it's money! I didn't know the Fellowship existed until I read this; I never applied for the Fellowship, I applied for "YC". I don't even know how to react. I order more pitchers. I lose my jumper.

YC Fellowship is a new program they're trying for the second time; this time they give cash and take some equity (1.5%) – but only if the exit is >$100 million. No pressure. It's a clever, founder-friendly instrument:
https://blog.ycombinator.com/fellowship-v2/
OK, sounds great actually. Having got all the way to YC interview, I'm bummed I've missed out on getting into "real" YC, but I'm elated at the YC encouragement and injection of cash. ($20k is material for me, since revenue is like $100/mo.) It's the biggest validation I have so far that I'm not wasting my time.
Kevin Hale will lead the program and have a call with me a few days later.

I create a Delaware C company, and now I'm on the road to building a unicorn, surely?

I return to the bar, but they haven't seen my jumper. A mystery.

The YC vote of confidence makes me double-down on the vision they're excited by: "AdWords for Podcasts". Podcasting is woefully behind video/display ads, so the area is ripe for disruption. Midroll will find advertisers for you… but you'll have to do host-read ads, and they'll only represent you if your podcast has something like >50k downloads per episode. What about all the indie podcasters with 2,000 listeners each? And why do I as a listener in Ireland keep hearing ads for services only available in America?! It seems like a motivating problem to solve, and the right amount "hard".

The YC Fellowship kicks off with a few days in YC in Mountain View, so they fly me all the way out to California again… then every body flies home and the program is remote. During the Fellowship, I work from home: I drink pre-workout and code a lot.

Thing is, I'm still a solo founder learning to code. Each week of the fellowship, I'm supposed to be focusing on growth, but I find myself spending my time fixing bugs and losing all my time just trying to keep the product from falling over. I conclude I'm not as good a coder as they think I am.
I'm spend time learning about adding an index to the database to speed up queries, or de-duplicating IP addresses to make analytics more accurate, or wondering why my Heroku bill is a multiple of my revenue. Now I feel the pain of being a solo founder, because when I'm busy fixing some deployment issue or whatever… nobody is doing anything else to grow the company.

I feel like there are way too many basic things to do before I actually grow fast, and perhaps YC have over-estimated my ability to execute, or over-estimated the state Awesound is in currently.

The Fellowship is to end with "Virtual Demo Day". As the weeks go by, I do convince some more publishers to sign up, and I get some sort of a growth chart, but many of these new podcasters are signing up on the free plan… Far from unicorn I feel.
Getting to sufficient scale where Awesound can sell dynamic, targeted ads across a long tail of podcasts… that feels far away.
I check the maximum daily dosage of pre-workout, and consume exactly that.

I had limited savings, but plenty of enthusiasm.
I'd quit my job, but I couldn't actually code. So initial progress was understandably slow.

I hadn't enough confidence I would succeed to ask another person for their hard-earned money. And I would't ask a friend to "quit your job to join me in building X" until I decided what X should be. So I set about building it myself.
I had too many ideas and figured I put something out there, and iterate based on feedback and early users. That's what some startup advice said.

My main challenge building the platform was needing to code. This made things slower than if I had been able to code. But, it wasn't a deal-breaker. I had done some C++ in college, and a little bit of python, and Django was proving to be quite understandable. In fact Django was python, though I'm not entirely sure which commands are python and which commands are Django specific. It doesn't matter though, because users don't care about these details either.

A key feature of an audio publishing platform, I decided, should be the ability to upload audio. Indeed, this seemed like a rather critical thing to figure out.
Thankfully, Google offered over 200 million results for "audio uploader add to website". I learned I should be storing files on S3, separate from the code of the website. I picked a library called s3-fine-uploader because, well, that sounded fine.

I remember following the documentation for s3-fine-uploader. They seemed well-written; that's part of what drew me to using it. Unfortunately, though they boasted that many people use s3-fine-uploader, their documentation had typos, or I was mis-interpreting it somehow: I pasted the example code EXACTLY into my html file, and it didn't work. Hm.

After checking that I had indeed pasted the code exactly as in the docs, prepared to make my first contribution to the world of open source software: my first post in Stack Overflow, explaining how the documentation was wrong, and how it doesn't actually work. As I checked the details, to ensure I explained myself correctly, I realised something very important: the code I was pasting was "JavaScript", and I was pasting it into a .html file. This is possible, but you have to put the javascript inside <script></script> tags. Ahhh.

Learning the different between javascript and html turned out to be very useful, and I remember it to this day.

I felt they could have done a better job in the documentation, by saying something like, "the following lines are javascript" before just sharing the code snippet. Perhaps the author of the documentation thought it would be obvious to the reader. If so, I looked forward to the day when I'd know whether a code snippet was JavaScript or HTML, just by looking at it.

I persevered for several weeks or months like this: focused on some core set of functionality – log in, log out, upload, press play, press pause – no matter how the platform evolved, those seemed appropriate to build.
I used Google to reveal millions of answers to literally every question I had.
"Change the tiny image in the browser tab for my website".
"Make corners of button roundy".
"Make corners of button less roundy".
Google had it all.

I even used git for the codebase, like a programmer would. If I made a mistake or confused myself, no worries; just restore from Dropbox, create a new repo and start again.

Speaking of Dropbox, did you know you can use Dropbox as a CDN? Simply set the permission on a file to be "public" and you can embed .css or .js files right into the <head> of your page. This means you can make a file change to the .css file while testing on your machine ("local host"), and any users of your website will also see the change in real time – ideal! No need to worry about re-deploying. This way, you can use your users as testers: if you make a bad change, your users can let you know right away.
The only snag is that Dropbox has limits on how many times a public file can be accessed per hour, so if you have more than about ten users, sometimes the .css file won't load at all for some users. Thankfully this isn't really a problem if you have few users.

After gradually to learn to "code" (copy-paste) from Google like this, I eventually had a fledgling beta. It didn't feel worth of a "launch", so I guess I "soft-launched", without any fanfare or publicity, to get my first users: indie podcasters. By "soft-launch", I mean I messaged a few podcasters and asked them to try it; they warmed to me, and are excited to use it. Woo, that was easy. But for the most part, they're not paying customers.

I've built a Libsyn alternative. I believe I can build much more detailed analytics than Libsyn offers, and I have a future vision of building a dynamic targeted ads marketplace in future when I reach scale. For now the focus is grow the number of podcasters on the platform, and build out core features like robust analytics, automatic distribution to other platforms, and building time-saving tools for podcasters.

Awesound so far is an alternative to Libsyn. Better in some ways, worse in some ways.
I start to build some cool new features, like transcription with auto-advancing transcripts. But, transcription (with Speechmatics) costs me, and I pass this cost on to the podcaster. Turns out most podcasters don't care about this feature.

First podcasters using Awesound include Gregg Clunis and Jennie Friedman. I am grateful to everyone who takes a chance on me.
I confuse myself a little with what pricing makes sense, and wind up offering a very generous "free tier", which includes the first 100 hours of uploads for free (only transcription costs extra).

Having never built a website before, I'm excited people are actually using this thing I've built, though revenue is limited to a handful of folks on the $5/mo. plan and a handful on the $39/mo. plan. In some cases, people are on a paid plan when they don't need to be. They're as confused about pricing as I am.

I had been thinking of audio ideas for about three years, and mulling over a name the whole time.

In many ways the name doesn't matter at all. But you do need to pick SOMETHING to have SOME .com to build your website on, and to have some brand name for all the social media accounts etc.

I mainly chatted with one friend about potential names: Ciarán Gallagher – the same friend who first introduced me to podcasting back in 2012! I had an mp3 player back then, and he loaded some "This American Life" episodes onto it from his laptop.
Several weeks later, I'd listened to all he gave me, and I had to figure out how to get new episodes… on my Blackberry. And so I really learned what a "podcast" was and how to "subscribe"… Even on Blackberry, was a podcasting app! It was cool! New episodes showed up like new email. And not like annoying [ACTION REQUIRED] email, but more like email you're Cc'd on, so can ignore if you like, or enjoy if you like. Absolutely class.

I later discovered a better podcast app on my (personal) Android, and in 2014 work upgraded our Blackberries to iPhones.

As my love of podcasting evolved from "heard of it" to "want to build a business to improve it", I naturally used Ciarán as a thinking partner in coming up with a name. Well, specifically he offered "Name is important... Can I be of any help there?" and I took him up on the offer!

I got hung up on the name "awedio" but awedio.com owner wouldn't reply to my emails. Since he wasn't replying to my digital efforts, I even tried to reach him physically. In desperation, I paid ~$20 for a stalker type report online that promised extra information about the person, deduced their address in Los Angeles. I believe the site I used was legal. Now, I live in London, so I wasn't about to fly out there and harass they guy in person. I did the next best thing: I ordered flowers and a hamper with a "thank you" card… pre-emptively thanking him for getting in touch and being willing to talk to me. The flowers/hamper had no effect, I still never heard from the domain owner. Wasted about $100, all-in.

I bought awedify.com, but if you say "aweify", it's not obvious how to spell it. The worst reaction was "oh cool, like Spotify.com, but audio" and I thought nooo, it can't sound like a knock-off of another company!
Besides, audify.com was already in use for something else… I'd need a more unique name.

Ciarán and bounced a LOT of ideas back and forth…
Which ones sound unique, not like variations of other company names?
Which have good connotations vs dodgy ones? ("brAWEdcast" sounds like "brawl")
Which ones would you know how to spell just by hearing it?
Which ones have the .com available?
Which words sound good as a verb?

After 2-3 years of noodling around different names, I finally came up with one word I loved more than all the others: "Awesound".

Hm, if I could get "Awesound.com", I'd be glad the "Awedio" man never replied to me. Awesound is even better!

Alas, the .com was taken – bummer!

But it wasn't exactly an impressive-looking site… do they really need it? Perhaps they'd be willing to sell?

Reading back, the exchange of emails is a classic exchange laden with "sorry for my late reply" messages:

Sep 19, 2014: I sent the first enquiry email.
"I'd love to buy awesound from you if you'd consider selling it?"

Sep 20-25: Received several "delivery failed" messages for the email addresses I'd tried, and so I tried different emails.

Sep 26: I received the first reply.
"I have just now seen this and your previous message. Interesting project!
I will pass your request on to the domain's current owner, for whom my company provides technical services.
On his behalf, I will ask you what you are offering for the name."

Oct 22: I realise my reply is still in drafts, and I finally hit send. In this email, I pick a number and offer it:
"If awesound.com were available now, I would be willing to offer up to $800 if it's available immediately (will save me time further investing in another site). That's a lot right now, but it will turn out to be another sort of "waste" if I take several more weeks to settle on a name, so I am willing to offer that much now. I can paypal whatever email you give me directly, or use escrow if you prefer."

Oct 29: After no reply, I follow up.
"I realise I initially let a month slide by and now I am following up very impatiently!"

Later that day, receive a reply:
"Once again I didn't see your initial message right away (this one), but your second one prompted me to go back and check. I have just passed this along to the owner. Sorry for another delay.

Also, see a more direct email address for me in the Reply-To of this message.

I will await hearing from him with further instructions; if he agrees, you can work out the PayPalling of funds between yourselves, and I will transfer the domain at your instruction, or modify the DNS at its current registrar if that is desirable."

So the offer has been passed on to the owner, and all I can do is wait.

On October 31st, at a halloween house party, I see a new email on my phone, and I have to eagerly open it right away:
"He has agreed to sell, congratulations!"

I remember immediately sharing the good news with my newest friend, who was sort of unaware of the long context behind it all, but very happy for me in my elated state. We were at a house party and left shortly afterwards when others started doing coke – not our scene. After a long night partying, he bought me dinner at what must have been 2 am or so, in a middle-eastern restaurant that seemed to be serving food all night. The whole night was a sort of bizarre London experience I wouldn't have had in my hometown of Cork. We celebrated our new friendship, and the new .com, which would surely be the beginning of great things.

AWESOUND.COM – I love it.

After just over two years as a Business Analyst in McKinsey, I had my "offer to return" in hand. This means I am promoted to "Associate", provided I first go and do something else for 1-2 years.

After the two-year grad program, most Business Analysts get that "offer to return." Most go on to:

• Do an MBA
• Work for the government for a while
• Work for a NGO
• Work for some Big Co.
• Do a startup
  …then come back to McKinsey as an Associate. Or never come back.

I was only interested in one of two things:

• Create my own startup.
• Apply to join Stripe.

After weighing up a few different startup ideas, and drafting but never sending an email about applying to Stripe, I decided to pursue the audio idea I had in mind. Perhaps the all-promising landing pages had convinced me the rest would be easy from here!

On my last day, as is the McKinsey tradition, I sent a "goodbye email".
My email had the subject line: "Thank you for inspiring me. Today I am leaving to create an audio startup"

It's official, now.

My smartest friend had told me about jQuery and Django some years prior. I realise now that "some years prior" is a big deal when choosing a tech stack – new frameworks advance quickly.

Well, I googled jQuery and Django, and it was easy to create a site and put it on the internet! I was rather delighted with myself. It even had a database and all. So we were ready to rock!

I cannot stress how arbitrary that first decision was, to use Django and jQuery. I spent approximately zero minutes weighing up different tech stacks. I had dabbled in python before, so Django seemed like a decent first thing to try. And it worked. So years followed, slowly developing a powerful app in Django, with full-page reloads for the most part – without any decision up front about what tech stack might make sense.

There's a saying in Irish, "Tús maith, leath na hoibre", which means "A good start is half the work". I guess I was in no mood for theoretical pros/cons of tech, I didn't care at all about the underlying tech and knew the listeners wouldn't either. I also felt EVERYTHING I do is just temporary and will be re-built really soon, so I only cared about getting SOMETHING online, to get feedback on different ideas, as soon as possible.

I had a whoooole bunch ideas around audio – in particular the social elements of sharing and discovery – and I made a landing page, with some mockups of what I had in mind.

The best .com I had at the time was awedify.com. I see the Wayback Machine didn't crawl my site in 2014 (probably because nobody knew about it), but there is a record of it a few months later, when it was still online on the new .com:
https://web.archive.org/web/20150328132259/https://awesound.com/demo/quote

My obsession initially was from the listener side: sharing quotes, saving bookmarks, discovering what podcasts your friends are subscribed to, and in particular: blurring the line between a formal "podcast" and a casual "voicemail". Ideally, blurring the line between having to choose to "listen live" or "listen to a pre-recorded podcast".
Obviously a pre-recorded podcast can be listened to at 1.5x speed, and live cannot… but I liked the idea of a single "feed" with a mixture of audio for your ears only (e.g., a voicemail from a friend, or an article you'd saved read out by text-to-speech generator) mixed in with "broadcast" audio like live radio (which you can of course pause if you need to) and podcasts (totally pre-recorded).

If it's 12:05, I should be able to turn on a show that started 5 minutes ago, listen at 1.5x speed until I catch up with "real-time", and continue listening live.
If I get out of my car, I should be able to pause the live radio, and resume where I left off when I get back into my car.
[This is how live videos on YouTube work: you can join a live broadcast late, and rewind, and play at 2x speed until you catch up with live. You can pause as you need.]
Having to decide "Do I want to listen to this live, or do I want to wait for the podcast to be available" seemed so antiquated.

I had probably 100 ideas at this time. I didn't fully appreciate that that coming up with ideas is easy; building is hard.

I noted some of the ideas on the landing page, stuck a "beta" sticker on it so it would be obvious you ain't seen nothin' yet, and invited folks to leave an email (or email for info?). Come to think of it, I think I didn't even have a proper email capture form set up.

The website was probably seen by nobody, and I'm not even sure why I started by building out landing pages… I may have been the only one to see the website, but if I was the target audience, the website worked: it was enough to convince me that I was onto something, and I should quit my job and make this a reality.