How to skip the line

 I’m embarrassed to admit I waited in line at a nightclub for 9 hours.

And I never got in. When I was 18, there was a club everyone wanted to go to. I got there nice and early when they opened. It was a chilly night. I wore a massive puffer jacket. Honestly, it was cruel to make people wait outside in the Antarctic conditions.

But people like me were suckers.

We had to be seen at this nightclub to inflate our fragile egos. I went with two of my friends. At the start of the night, we thought it was a given we’d get in. The wait was long. After 2 hours, we got to the front of the line. We were pumped.

Then the doorman Jason said “Sorry, guys, without a guest list, there’s going to be a bit of a wait.” We didn’t mind. We would wait. Every hour after that, I’d check with Jason about the wait. He kept telling me “Not long now buddy.”

At 6AM the nightclub closed. We were still outside waiting to get in.

Jason said “Sorry, guys, maybe next time.” I crossed the road and just stood there. I saw Jason and the security guards laughing. I assumed they were laughing at us.

I was pissed. I felt betrayed.

The two friends I was with thought I overreacted. A few weeks later, we weren’t friends anymore. I never quite got over what Jason did to us. It was cruel. He had no intention of ever letting us into the club. It was a game.

The 9 hours we waited in line to get in taught me a lot. I saw one guy give a $50 note to the security guard and go from the back of the line straight in. I saw hot girls walk to the front of the line and be let straight in.

We were in the general admission line. On the other side was the guest list. Those people didn’t wait. And right at the front was a VIP entrance. They didn’t line up or talk to anyone at all. They went straight in.

The next day I realized this is how life works. There are three entrances to every opportunity and most people choose the general admission line.

The story doesn’t end there.

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About a year later, I found out that my dad had met the nightclub’s owner. My dad introduced us. The owner said, “Timbo, if you ever want to come to my club for free, let me know.”

So I did. The next weekend I went with the owner to his nightclub. I saw Jason. His whole vibe changed. He looked surprised. It didn’t end there. I ended up working for the owner. That meant I could use the staff entrance.

I could walk into the club whenever I wanted and do whatever I wanted. Jason saw. He watched. Then it went even further. I became a DJ at that nightclub.

Jason now saw me walking in with bags of vinyl records and a small crew. He saw me get handed stacks of drink cards for free alcohol.

On my birthday the owner threw a party for me. All my friends and I drank for free. Jason saw that too. Then one night, someone handed Jason one of my demo CDs of a mix I’d done. He walked up to me later that night and said “Man, that mix you did is one of the best DJ sets I’ve ever heard.”

He was blown away.

I never forgot what happened at that nightclub. It taught me you can settle for the general admission line in life, or you can find a way to skip the line altogether.

Stay the hell away from the front door

The front door for any opportunity is where you ask for permission.

“Please, sir, can I come in tonight?” The crazy thing is most people choose the front door. They choose the traditional path. They get told what to do.

Right now what makes me emotional is seeing so many people being laid off, then applying for jobs on websites or LinkedIn. It’s sad because they use AI to write their resume, and then the employer uses AI to read their resume and screen them out.

Humans are removed from the process.

And so many job ads are fake. They’re posted for compliance reasons, to test the market, or to build a pipeline of people for a possible future opportunity.

If you apply for a job and ask for permission, you either get ghosted, put through endless interviews, or low-balled on the job offer because everyone is getting laid off.

The front door sucks.

Same with dating. If you go through the front door and end up on some dating app, you’ll be put in touch with predators, people looking for free or paid s*x, and blatantly rude people who treat you like a doormat they wipe their dog sh*t filled feet on.

Starting a business is another area where the front door sucks. You go it alone through trial and error. You ask the bank for a loan to buy a business. Or you buy a McDonald’s franchise where they dictate the rules and take a huge chunk of revenue.

Either way, you’re asking for permission and being treated badly.

If someone stands in between you and your freedom, it’s a trap. And that’s every front door in existence.

You’ve got to be bold as hell to skip the line

Skipping the line sounds simple. Like anyone can do it.

I disagree. To skip the line you have to reject everything you’ve ever been taught. You have to reject what 99% of society does. But most of all, skipping the line is deeply psychological.

When you decide to skip the line you’re becoming a rebel. You’re being bold, courageous, and dangerous. When Freddy McBasic finds out what you’re doing, you’ve got to be strong enough to ignore him when he tries to talk you out of it.

But most people don’t act boldly. In fact, they don’t act at all. They just sit there in fear for most of their life and fantasize about what they could do without doing anything.

That’s your opportunity.

The high-profile job that didn’t exist

Early in my finance career, I was stuck in a call center. I couldn’t break out.

One afternoon a manager asked our team if one of us could process the paperwork for a small startup. No one wanted extra unpaid work. I said yes.

I’d never heard of the company. They were called Braintree, founded by the “don’t die” guy Bryan Johnson.

I did their paperwork as fast as I could. And I emailed them every day to keep them up to date. I didn’t think much of it. But they thought I was a hero. They told everyone at the bank I worked at how much of an asset I was to the company.

Eventually, I got a secondment to work with this manager directly. He taught me everything he knew. At the end of the secondment, he promised me a job. But there wasn’t one. I waited a year. Then the manager came back to me with an open position. It was at least 3x more senior than my current role.

He told me I already had the gig but to pretend I didn’t. I did fake interviews and acted humble. Then I got the job.

It was a dream job. Everyone wanted it because it dealt with Silicon Valley tech companies. Guys with decades of experience applied. Guys with better tech backgrounds and who drove $400K cars applied. None of them got it.

Somehow, underqualified, overlooked, stupid old me got the job.

And the people who missed out were pissed.

They complained. But no one cared. Every day after that I had a target on my back. They did everything they could to make my career a living hell. It didn’t work.

I got a dream job I was stupidly underqualified for because I went through the back door. I did admin work with no reward to prove competence. I showed I was high agency. Around this time, Braintree sold to PayPal for ~$800M. I now had a giant client backing me. Speaking up for me. Telling my employer they must promote me. And big companies always listen to big customers.

The challenge with skipping the line is you must be delusional.

There’s no roadmap or guarantee. You must do what isn’t rational or scalable. You must do things with no clear reward. And you do those things because you understand the rules of the skipping-the-line game:

• Do hard work

• Act high agency

• Be humble as f*ck

• Build relationships instead of create transactions

People always told me I was talented or lucky, and that’s why I got the job. What they didn’t know was I learned how to skip lines because I waited 9 hours to get into a nightclub when I was 18.

The worst startup in history skipped the line and became a unicorn

In 2008, everyone laughed at Brian.

He’d pitched his startup to 20+ investors. They’d all said no. He was selling novelty Obama O’s cereal to pay his bills. If there was a line, Brian wasn’t at the back. No. He was banned from the line for being an incompetent fool.

Brian had the crazy idea of pitching his startup to John Doerr at Kleiner Perkins. John was seen as a mythical god of the tech world. People kissed his butt and licked his feet because of his early investments in Google and Amazon.

To get on his calendar, you had to be referred by a tier-one investor or founder and wait months. Even then, there was no guarantee. Brian had no chance. He was Kramer from Seinfeld dressed in a clown suit asking Buckingham Palace if he could stay with them for a year and share a toilet with the King.

Brian had a screw loose.

He didn’t bother with front doors. Wasn’t his style. He preferred a more backdoor approach. Giggity giggity.

Brian found out John Doerr was heading to a conference. He used the last of his savings to fly there. While everyone was networking and slamming business cards in each other’s faces, like desperate sheep looking for a root, Brian went on a stakeout.

He watched John’s every move.

After John spoke all the sheep descended on him. He was swamped with beggars, freebie-seekers, and “Can you sign my google t-shirt?” Poor guy. I’m sure he could cry tears into $100 bills from his multi-billion-dollar fortune, though.

After everyone tried the front door and failed, Brian descended into the dark and gloomy car park. He found the speaker’s VIP exit. He stood there like a creep. He watched. He waited. He smoked a cigarette.

Then John exited the building. He was all alone and headed for his ride home. Brian knew it was go time. He appeared out of the darkness. Instead of asking for permission by saying “Excuse me kind sir, can I pitch you my startup if you have a minute,” he just went straight to value.

He explained his startup’s core value in 30 seconds.

Brian said they were going to unlock the surplus capacity of millions of spare bedrooms around the world. He chose that instead of talking about challenging hotels or running a marketplace which sounded generic and obvious.

John was surprised by Brian. He didn’t expect the pitch in the car park. Brian’s appearance, financial position, KPIs, or pitch deck didn’t matter. What John saw was a high agency individual and he instantly got him a meeting for the following day.

Brian’s startup is now known as Airbnb.

Now, that was a nice story. Beautiful hero’s journey ending. Heck, you could turn that into an animated Disney movie and call it Cinderella. Glad you liked the show. Please leave your tips at the door. Now let’s go for drinks.

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Wait… hang on a f*cking second. The story doesn’t end there.

Brian did have the meeting with John. But John was a prick and didn’t invest in Brian’s startup. He thought the idea was too weird and creepy.

The idea strangers were going to sleep in your spare bedroom tucked nicely into your bed with freshly washed sheets was wild. Creepy even. And god forbid those strangers did the dirty in your bed and left white stains on your Eight Sleep mattress. Yuck.

Too weird for John. So he passed.

But something odd happened. When all the other VCs and investors found out about Brian’s meeting with John, he went from being the homeless guy no one wanted to go near to an Instagram super model in a Victoria-Not-So-Secret g-string, baby. Jackpot.

The takeaway here is when you attempt to skip the line, it doesn’t guarantee you’ll get what you want the first time. But it does mean you’re now in the main game. People take you seriously. You can make things happen.

Brian eventually applied to well-known accelerator Y-Combinator. Silicon Valley royalty Paul Graham didn’t let them in right away. He, too, hated the idea of strangers sleeping in people’s beds. But when Brian told him how he sold $40 boxes of Obama O’s cereal to keep the company afloat, Paul nearly pissed his pants.

Brian stunk of high agency. And it’s so rare, Paul let him into Y-Combinator even though the idea was stupid. Because you never want to underestimate a high agency person who skips the line for a living.

High-agency moves don’t eliminate failure—they just eliminate the wasted time spent waiting in line to find out.

Alright, here’s how the heck to do this in reality without all the hype and Lambos

There are some general principles I’ve learned being a serial skipper of the line (mostly because I hate kissing ass and sucking off gatekeepers).

First, assume if you’re resourceful enough, you can always find a way to skip the line. If you don’t believe this and you’re not completely delusional, skipping the line won’t work, and you may end up in the homeless shelter line by accident.

You and I are not the first to skip the line. We won’t be the last. History is full of the greats who secretly skipped the line. If only we knew. You know the tech bro Tim Ferriss? He has that best-selling book “The 4-Hour Workweek.” The hero story is that it was a great book and he went from nobody to somebody.

Not quite.

Tim’s advisor the whole way through the book process was Jack Canfield. If you don’t know Jack, well, he wrote Chicken Soup for the Soul – one of the best-selling books in history. So with Jack by his side, it was unlikely Tim wasn’t going to smash it.

But that part of the story is left out. It ruins the mythical nature of it.

The point here is Tim found a way to skip the line. He somehow got one of the greatest authors in history to back his book project when he was a nobody.

We don’t know how, but we at least know it wasn’t privilege or a rich family because Tim had neither. So somehow Tim Ferriss was resourceful enough and got to skip the line. This shouldn’t be a surprise.

In other areas of his life, Tim is famous for being resourceful. In his first job, he famously figured out a way to reach CEOs after hours while everyone was calling them during business hours.

The second way to skip the line is to share your ideas online.

People don’t buy products or services. They buy ideas and the people behind those ideas. Social media is one of the best ways to make that happen. I recommend you write every day on one big social media platform. Share stories. Share ideas. Don’t freaking paywall anything. Focus on being helpful.

The third way to skip the line is with non-needy networking. This is where you make it a habit to proactively connect with people without asking them for anything or saying “Can I pick your brain?” like an absolute moron.

You do it by leaving thoughtful comments on people’s social media posts for a while. Then after a few months you reach out via the DMs and start a conversation. Because they’ve likely seen your comments by now, they’ll reply.

Now you have a new connection. Someone you can build a relationship with. Do this enough times and you end up with a powerful network. That network can help you meet hard-to-meet people, and see opportunities others don’t.

When someone is looking for a co-founder, they don’t put up a job ad. No. They go to their network. That’s how I found my co-founder. He was referred to me.

The best opportunities with the highest leverage, most status, and biggest paydays aren’t public. Read that again. So if you’re waiting around for opportunities or hoping one will find you, you’re wasting your time. Skip the line and start doing non-needy networking tonight.

The last way to skip the line is the hardest of them all – it can’t be faked. It’s to have proof of work. It’s to rack up hundreds of hours actually taking action, reaching goals, and gaining experience in a field. Along the way there will be stories that happen.

This is powerful for skipping the line because when you can show you’ve done things, and you can share interesting stories about it, people pay attention. They see you’re real. You’re secretly given the label of a practitioner. This is how you stay away from the front door and avoid asking for permission.

It’s what I did. I wrote every day online for 12 years so that my proof-of-work was undeniable. So that the outcome of my success would be inevitable. It’s simple to understand but hard to pull off.

Theorists say, “I think I can do it… give me a go.” Practitioners say, “I’ve done it before, and here’s what I did.” Nobody gives a f*ck about your potential. They only care what you’ve already done. That’s the fastest way to skip the line.

Go skip the line

You now know the principles.

Go try them for yourself. Watch opportunities flow in your direction. Be humble when they do. Show others how to skip the line too. The journey won’t be easy, but the failures and rejection will become the best kind of nostalgia later on.

The market right now is tough, no matter if you’re an entrepreneur or an employee. This is the cheat code. This isn’t hope, it’s a strategy you can implement.

Stop going through the front door. Use the back door, VIP entrance, or go really crazy and use the staff door. You’ll be amazed at what happens when you do.