My Top 3 Ways to Get Started Making Money Outside of Corporate

You already know my core belief. The real path for most escapees is monetizing your corporate experience. That's the long game and it's the right game.

But sometimes you need to generate cash now. Build some confidence. Prove to yourself the money can come from somewhere other than a corporate paycheck.

Last week I signed two UGC deals. Didn't use my audience. Didn't post about either one until they were done. They were just looking for real users with real stories and BTW they pay real money.

I have been going down rabbit holes of how to make money outside of corporate. As long time followers know I have figured out how to monetize my corporate experience over 10 different ways but now I am exploring ways to generate income with or without corporate experience.

Most escapee gurus tells you to chase the one big anchor client, the dream fractional gig, the perfect offer and a long time client. Don’t get me wrong fractional is a great cornerstone revenue stream but there are quicker ways to revenue that anyone can do.

The folks I see actually building a life-first future do the opposite. They start small. They get reps. They learn what selling, scoping, and delivering on your own actually feels like. The bigger deals show up later almost always because the smaller ones taught them how to hit.

Here are three revenue streams to consider:

Brands need creators. Creators in the millennial, GenX, and boomer demographic are in short supply.

That's the whole game. You don't need a following. You need to look like the customer the brand is trying to reach. If a 50-year-old brand wants to sell to 50-year-olds, a 25-year-old creator isn't the answer. You are.

The math is friendly. Most deals run $300-$500 per video. A couple of hours of work. One deal a week puts you at $1,500-$2,000 a month with almost no overhead.

That's not your full corporate salary. It's not supposed to be. It's the first dollars that aren't tied to a W-2. And that first non-corporate paycheck changes how you think about everything else.

I had Megan on the podcast a while back and she walked through exactly how to land your first few deals. Episode is still relevant. [Listen here.]

She's also coming back on the show for an updated take, so keep an eye out.

Worth saying: this isn't a long-term identity. It's a fast first base hit. Sign a deal, deliver a video, get paid, build confidence. Then keep going.

This is the one I'm watching people quietly crush.

Pick one problem you can solve. Package it. Sell it the same way every time. Same scope, same price, same deliverable. That's a productized service.

The hardest part is the picking. Most people try to keep all 25 years of corporate experience on the table — which means they end up selling nothing because nobody knows what to buy.

Get specific. What's the question your former colleagues keep DMing you about? What problem do you solve in your sleep? That's the offer.

I broke down a real example of this in a LinkedIn post recently [Post Here] . A car financing service that turned one-off consulting work into a packaged offer the founder doesn't have to deliver every time. [Read it here.] The principles apply to almost any senior corporate skill set.

The math on this one beats UGC. $1,000 per engagement is realistic for most experienced operators. Land a few per month and you've meaningfully changed your income picture.

This is also the on-ramp to fractional work. Most fractional clients first hire you for a small productized engagement, see your work, then ask for more. The repeatable service is how fractional finds you. Not the other way around.

There's a gap forming in the market and almost nobody is filling it.

Every Fortune 500 has consultants advising them on AI. The 32 million small businesses in this country mostly have nobody. They know AI matters. They have no idea where to start. They don't need someone to fine-tune a model. They need someone to walk into their business, look at how the work actually gets done, and tell them what to automate first.

That someone is you.

Not because you're an AI engineer. Because you spent 25 years watching companies operate. You know which meetings shouldn't exist. You know which reports nobody reads. You know where the friction lives. AI gives you the tools to remove most of it. The pattern recognition is the asset. The tools are the commodity.

The starting move is simple. Pick three small businesses in your backyard. Offer a free workflow audit. Show up, listen, point at three things AI could fix this week.

One of those three calls turns into a paid engagement more often than you'd think. Pricing in this lane is healthy with quarterly retainers in the $2K to $5K range for ongoing advisory.

I'm building this out right now and there is a window of opportunity for the next 18-24 months to get out in front of this. The window is wide open right now and I don't expect that to last.

Three options. Don't start all three.

The trap with a piece like this is reading it, getting fired up, trying to start everything at once, and finishing the week with nothing done. Pick one. The one you can start this Saturday morning.

UGC — if you want fast first dollars and being on camera doesn't scare you.

Repeatable service — if there's an obvious offer already hiding in your inbox.

AI advisory — if you have small business relationships ready to mine.

Pick the one that fits where your leverage already lives. Spend 30 days running it. Don't pivot. Don't add a second option. Just hit some singles. The bigger swings show up on their own once you've put in the reps.

You don't need to escape corporate to start. You need to start to make escape possible.

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If you want to run these alongside other folks doing the same thing, that's what The Escapee Collective is for. GenXers building a life-first future, trading notes on what's working, keeping each other moving.

$20/month. First month is $1 — come in, look around, see if it's your room.

[JOIN THE COLLECTIVE ]

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I moved the Corporate Escapee podcast over to beehiiv. Current episodes and the full archive are all in the same place as this newsletter. Subscribe once, get everything.

One worth queuing up if this issue hit:

Jess Cole and the Savannah Bananas — what every escapee can learn about building a brand people actually want to be part of. One of my favorite conversations of the year. [Listen here.]

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P.S. If you're already running one of these, hit reply. Tell me which one and what's working. I read everything that comes back — and the best moves I end up sharing publicly? They came from you first.