this is an excellent starting point for a discussion about risk, safety and spectacular failure

and actually this is also a fun starting point to tell you about my foray into becoming a rock concert gig promoter https://twitter.com/RealtimeAI/status/1214188329190789125

when I was a teenager, I discovered that sterile Singapore actually had a delightful local music scene – sweaty, earnest, vulnerable, intimate. I knew immediately that I wanted to be a part of it, so I learned to play (terribly), and sought out bandmates to play with

once you get involved in something, of course, then you become an insider, & you start to develop an insider's point of view. and while I loved music and musicians, I learned that that many gigs in SG in the 2000s were *terribly* organized by people who preyed on naive new bands

the playbook:

1. book a venue

2. seek out new young bands made up of teenagers

3. tell them that, to play, they have to sell ~20 tickets at ~$10-20 each

4. barely bother doing any promotion, don't care if the bands suck

5. book ~10-20 bands like this

OMG BLAST FROM THE PAST

I wrote this... 13 years ago??

this is what I was doing instead of my homework, and I would 100% do it all over again

damn, I have always tried my fucking hardest to go above and beyond to fight against shitty equilibriums to make good things happen.

anyway! our first gig was a great success! we booked a small-ish venue, called several other mid-tier bands that we liked and admired, charged a fair price, publicized it. I believe about 100 people turned up. I think I pocketed like $300 for it, which was amazing to 17yo Visa

Now, the SMART thing to do would have been to save that money for a rainy day fund for the budding organization. But we were 17 year old rockstars, so... We spent it all on cigarettes and alcohol

And then we had one particular show – I don't remember how it happened, but it was the debut show of a new band made up of well-known musicians from other bands, and so we found ourselves organizing a gig with much more popular bands that we normally worked with. It was amazing

I think there were like... 300 people in there? my friends helped with the tix. we were 1 amp short at the venue, and one of the musicians brought his personal amp from home. it was a phenomenal night. and it all happened began with me wanting to organize better gigs

"Visa, ok, that's all sweet and everything but what does this have to do with ~spectacular failure~?"

We got cocky.

We had gotten a string of moderate successes, and even a spectacular success. Everything we touch turns to gold!

So we decided to organize our biggest gig ever.

We would wander around Singapore looking for live music venues, and ask to talk to "management" about booking the venue for an event. We'd wear suits because we thought it made us look older and more professional Y'know, I think it worked. They took us seriously. We made $$

I can't remember the details, but we found ourselves asking: what's the biggest, bestest venue we can afford? And we learned about Top 5 Disco – a large bar in Orchard Towers, that, IIRC, used to be a cinema(?). An amazing lighting setup. Amazing sound systems. I wanted it.

It was an interesting experience going to TOP 5 and talking to the boss (who was an elder lady who had definitely Seen Some Shit). I remember there were pole dancers and everything. I felt pretty nervous. But we psyched each other up and boldly made our proposal/request.

the venue cost $1,500/night to book. Easily 3x more than we usually paid for a smaller venue

We paid the bands $500, and gave them guestlists so their friends could attend (we even bought them dinner lol)

we hadn't checked the calendar: we unwittingly picked Father's Day

we had gotten complacent and pretty much assumed that the show would go well, since every show we had done before had gone well. on retrospect we didn't do enough marketing

we over-estimated how much marketing each of the bands would do themselves

and finally – I don't know how much this was a variable influencing attendance, but it felt so thematic/poetic – it rained heavily that day

In the end, I think barely 50 people were in attendance, mostly guests.

We lost something like $1,700. At 17, this was devastating

We'd never even discussed what we would do if we lost money. Every one of our shows had been profitable before, but this one show's loss I think cancelled out all of them. I was already depressed to begin with (broke up with S a month earlier, grades were shit) & this worsened it

catching up with CPL to revisit his part of the story. he's succinct as always

but with the gift of hindsight – $1,800, split between three people? about US$444 each? that was actually an *incredibly* small price to pay for this lesson!

when I started selling t-shirts years later, I was rigorous about making sure we never spent $ without first getting $$$

if we had saved say about 60-70% of our profits (meaning we pay ourselves, idk, $50/show, and put the rest "in the bank"), we would've been able to take the hit of the "big loss" without having to go near-hungry for months afterwards

this whole experience taught me so, so much

on retrospect we should have been much more rigorous about what we were doing, we should have paid close attention to the money. we should have checked the date. we should've realized that 3x cost means selling 3x tix. we should've been hustling to collect cash for each ticket

still, the risk *was* contained to $2,000. and this whole experiment was a phenomenal learning experience. we desperately wanted more out of life than just going to school, and we got it. the skills we learned serve all of us very well in our professional lives

in the bigger scheme of things, I truly believe that it would've been riskier to keep our heads down and merely do as we were told.

taking small-to-medium risks outside of the narrow track we were on was what allowed us to flourish as people, creatively, socially, etc

what does it even mean to "not take risks"? I think to most people it means staying on the well-lit paths, doing what other people are doing.

I also think that we live in a time of great upheaval, and everything that is "safe" and "stable" can suddenly become not-so overnight

What do you do if the company you work for goes under? What do you do if your job gets automated? What do you do if you have to become a refugee tomorrow? What if you had to start over from scratch?

What appears robust can be a lot more fragile than it seems

I do NOT, btw, advocate "quit your job and chase your passion!" I spent 5+ years working full-time while I was writing hundreds of thousands of words on the side. I saved up over a year's worth of runway when I was looking for consulting gigs that I was fairly confident I'd get

https://twitter.com/ryanmyfoo/status/1223230079930531841?s=21 https://twitter.com/ryan_rilke/status/1223230079930531841