What Bombing a Comedy Routine has taught me about Business

This is the tale of three new comics.

The Champ, The Boxer and the Bomber.

The rest of the field of fourteen had experience ranging from one to three years.

The place was packed.

120 people.

I met the Champ along with the Boxer before the show.

The Boxer was about 6ft3, about 30, full of courage, Dutch courage as he smacked a bourbon and coke.

The Champ was slightly bigger build than me, Irish, 33 like me; but had lived in Oz for 15 years.

He was a little more nervous than I was.

The work I do on myself every day has led me to believe I can control my state with my breathing.

As well as observation to laugh at my ridiculous self-talk (have you ever done that? — we’re silly us humans) so I don’t get that ‘shit-scared’ feeling before going up on stage anymore.

Not to say I don’t get a little nervous.

The bloke running the night took us through a few of the rules and gave us newbs a little bit of advice.

You have 5mins. No more, otherwise, you will be penalised.

You will also be marked down for racism, rape jokes, unnecessarily usages of the words starting with C.

Like Crypto — you’ll get that joke if you’ve ever seen me speak about my business…

And if you do get it and it’s not funny, maybe that’s why I’m the Bomber.

Or maybe you’re just a bunch of Cryptos.

We’ve still got about 15 mins to showtime and the Boxer has already told us that he knows how these things go down.

He’d been to a bunch of live events and parties…

I didn’t quite know how that really related to what we were doing but, except that it was live.

He proceeded to tell us the key to success was getting the right amount of booze in.

Now normally that’s my jam to talk about, but this guy had already had a few too many and wouldn’t have been in the mood to discuss optimal tipsy for standup comedy.

In fairness, I knew F-All about it.

The one thing I do know is that Anna, the first new coach of the 101 Tokens Lifestyle, is a comedian and teaches improv in Melbourne.

She refuses to drink now before a gig, given it puts her off her game.

Speaking at length about this was enough for me to flag it.

And there we are, 20mins to kickoff when the Boxer comes over to me and the Champ with a shot of Tequila.

“C’mon lads, this will have you ready to nail it.”

We politely decline.

I do outright, as Tequila Tuesdays aren’t my jam anymore.

But the Champ says he’ll have it with him after.

The Boxer is a bit bewildered, but downs his and walks off.


The thing about this competition is that there are some fresh AF comedians, like the three in this story.

So in the warming up of the crowd, the seasoned comedian MC ensures that he reminds all those in attendance of that.

‘This could be the moment you see a world-famous comedian do his or her first gig.


This could be the moment you watch someone’s hopes and dreams smash into a million pieces…’

That’s me paraphrasing.

He was a funny dude and I refuse to direct quote.

Perhaps that’s me picking up the pieces…

Just kidding,

I’ve already done that and it occurred as soon as I walked off.

Hang on!

Is this me meta-fucking the narrative again?

The MC intros the first lady up on stage.

She has some funny material.

She’s fairly overweight and it’s mainly self-deprecating jokes. But I guess most comedy is.

They say it’s super important for the person before you to be decent.

It’s like your warm-up.

Sorry guy behind me.

She is applauded off as her 5 mins is up.

The MC does a good job to whip up her performance to make it better than it was and then he intros me.

Now, one thing that’s pretty awesome is this…

If you get up and do a RAW comedy show (the Australia wide competition I entered)

At the very least you get an intro over a loudspeaker to a bunch of half-pissed people under bright lights and they all cheer.

Not a bad feeling.

And that’s where it ended.

Among the 100s of lessons. Here are three things I learnt from bombing spectacularly on stage.

1) Always invite your audience into the story.

I started off with a theatrical entrance and it didn’t land.

When a seasoned comedian told me some advice after my bit, it suddenly hit me that most comedians grab the mic and say ‘how are ya?’ and along the lines of ‘Can I tell you a story?’ AKA inviting people in and asking permission to get vulnerable.

The irony is that I usually do that with my audience when I’m telling this story in a work context. BTW for those interested in the story it’s an adapted version of this one


2) Stick to course:

After my first two jokes didn’t hit the mark, I started pre-empted that the others wouldn’t, so I started editing on the fly.

Speaking with my entrepreneur / mentor buddy Murray the next morning, he said that he uses the analogy of the comedian for new people running a business, or Startup for the purists.

He says ‘being on stage is like the most intense feedback loop you can receive.

Like a startup you are iterating on the fly. It takes a special skill to nail it.’

And like many a startup idea that I’ve destroyed, I was hacking, redirecting and cutting things way too fast.

I gotta give it to my brain that it was able to do this though.

But it kind of destroyed my map and my rhythm went completely out the window.

Not sure how I’ll go next time, because it felt automatic, but at least I’m aware of it now.

3) Practice in front of people.

Now at this point you’re probably thinking — ‘you fucking idiot.’

But, technically I had practiced.

Just not for a while and definitely not in the right context….

About three years ago in a room of comedians in Newcastle I got great feedback on the routine.

But it wasn’t the same thing. ‘Sitting’ with 8 people around a table who were there to help me, is different to ‘the loneliest place on earth’ behind a mic on stage.

And I’d done parts of this story almost 10 times on stages at business conferences and pitches. I’d got laughs too. But the difference is that people at those events weren’t there ‘to laugh’ — and a giggle was just a bonus.

When people have paid money ‘to laugh’, it’s a whole new board game.


Longest 5mins of my life and at the end I thanked the crowd for being there as it was my first gig.


Finally, I’d engaged them and they gave me a round of applause, which was nice.

I think even half-drunk people can feel a mix of sorry and admiration for someone who gets up to do that.

As I walked back through the crowd some people actually complimented me and the MC gave me kudos too.

I think if anyone in the world knows how that feels, it’d be a comedian who’s been in the game for a long time.

One of my favourite comedians Jim Jefferies, says it’s like an apprenticeship. ‘You’re shit for 4 years, cop all the shit, and then you get good.’

When I interviewed comedian Mitch Garling on my podcast he gave me some rad insights too.

Perhaps I should’ve listened back before I went on stage…

So how ‘bout the others.

A few comedians later the Boxer is announced to come up on stage.

And… one of the other things we were briefed on was to make sure you’re waiting by the stage for your call.

He’s at the bar getting two drinks when he’s announced.

There’s confusion as he doesn’t hear it the first time.

Then he does.

Yells out “sorry” and makes his way to the stage through the crowd.

Again, paying customers, having to wait for someone buying two drinks for themself…

He finally makes it up there and puts one down.

He starts well.

Super confident and gets a cheer when he says he’s going to talk about ‘drugs.’

(Noted for next time)

But that’s where it ends.

He’s so pissed that his confidence, which I’m taking an educated guess — as someone who used to get super pissed to find my confidence — that his nervousness outweighed the Bomber and the Champs combines.

The crowd are off it and he starts to get heckled.

Now, I received one ‘boo’ and even though I couldn’t see the guy who did it, I assume a mate of his gave him a nudge to say not cool. Because it was cut short and didn’t happen again.

Thanks invisible guy.

But because the Boxer fed the crowd back and not in a creative way, it all went pear-shaped.

He came off and had words with several people in the crowd.

At the intermission, a bloke beckoned him to go outside and they had a slanging match across the back of the arena as the Boxer bought more drinks.

I never did see him again and I’m not sure if he did thow any punches. But he certainly shaped up with his words.

What I learnt from the Boxer:

1)Don’t get too pissed before anything

2)If you’re going to heckle the hecklers have something decent to say
And the big one…

3)Just because you’re nervous, don’t assume everyone else has the same coping mechanism.

You may set them up for a worse fall than the one you’re about to take and that makes you a Mega-Crypto.

And that leaves the Champ…

He actually did have a gin and tonic before his set.

I wonder now whether that could have been a good option.

But like I said, I wasn’t really nervous.

I was just shit.

Props to the champ, he got up and beat a field of many decent comedians.

His accent along with his rhythm, vulnerability, likeability and invite into a wound of his that he found the lighter side of was a recipe for success.

He’s just a funny Crypto.

The three things I learnt from the Champ:

1) Be humble. Don’t expect laughs, let them come to you by being good.
2) Feel out the audience with jabs, before you go for the knockout. He set them up well.
3) Mark your territory. He did it early with setting the scene. Once he got the laugh there he knew he had resonance and the rest is history.

It’s interesting the feeling I had the next day.

That was that no presentation or even comedy gig will ever be as bad as that again.

It’s a bit of an unwarranted invincible feeling that I assume you would get from bringing the house down.

I’ve said to friends that had I been slightly better, I’d probably have hung up the gloves.

But because it was so bad, I’m going to go again.

And with the same passion, I’ve got for my bizness to succeed.

Even if it takes a 10-year apprenticeship.

Experiments in Vice Optimisation, Regenerative Business Building, Flow States and other random radness.

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