Rob Walling

> Are all startups at my age generally side hustles that become profitable enough to quit my day job?

Maybe yes. But that's only the first step.

40yo here, married, 3 kids (5yo, 3yo, 1yo), and a mortgage. I am more in the risk-averse side.

I was a CIO ('I' as in 'investment') in a family office. In 2019 I started building a document processing service (eg merge, encrypt PDFs) as a side hustle. It grew slowly and steadly, until, in May 2022 I got enough recurring revenue to ask my employer to reduce my load to half-time, taking a paycheck cut.

In the other half of the day, I am working in a more ambitious idea. I expect that at the time I am ready to launch, the income from my document processing service will be near 100% of my full-time FO paycheck, so I am taking very little financial risk.

Two resources that would have helped me a lot when I was having the same questions as you are:

- Rob Walling's "Stair Step Method"
https://robwalling.com/2015/03/26/the-stair-step-method-of-bootstrapping/

- Dan Hulton's "Evaluating Modest SaaS Business Ideas"
https://greaterdanorequalto.com/evaluating-modest-saas-business-ideas/

"The new business road test" - John Mullins "Will it fly" - Pat Flynn

"Start marketing" - Rob Walling (https://robwalling.com/assets/ebook.pdf) I recommend the article on "Why Startup Founders Should Stop Reading Business Books" ;)

https://youtu.be/19WpIbBhxJU

(don't know where I got this...)

Ideas are worth nothing unless executed. They are just a multiplier. Execution is worth millions.

Explanation: AWFUL IDEA -1 WEAK IDEA 1 SO-SO IDEA 5 GOOD IDEA 10 GREAT IDEA 15 BRILLIANT IDEA 20 NO EXECUTION $1 WEAK EXECUTION $1000 SO-SO EXECUTION $10,000 GOOD EXECUTION $100,000 GREAT EXECUTION $1,000,000 BRILLIANT EXECUTION $10,000,000 To make a business, you need to multiply the two.

The most brilliant idea, with no execution, is worth $20.

The most brilliant idea takes great execution to be worth $20,000,000.

That’s why I don’t want to hear people’s ideas.

I’m not interested until I see their execution.

Building an online course[1] has been one of the easiest ways to make money in my personal experience. Other things I've tried building: SaaS, Trades business, Freelancing business.

I've made over $8k since I launched last month and it's been a great stepping stone into other ideas. The main problem I see going forward is getting consistent traffic. Building the course was the "easy" part and now I'm focusing hard on SEO to keep consistent traffic going to my page. Long term I think I can make $100-$300 a day with it.

I floundered trying to build SaaS and other types of business for years before making some money online. Selling a one time purchase can be a game changer for those looking to go independent. Look at the stairstep approach[2] for reasons why this works so well.

Overall, if you invest a few days and put something out there, I think an online course can be a great way to build some income.

[1] https://www.vim.so
[2] https://robwalling.com/2015/03/26/the-stairstep-approach-to-bootstrapping/

Somewhat related, I know of people who buy smaller companies on MicroAcquire or elsewhere, typically for some small 4 or 5 figure USD sum, then they simply monetize it with ad spend and paywalling certain features. They generate 10x revenue then they sell it again for another 5-10x multiple, rinse and repeat.

For example, Rob Walling, cofounder of Drip, MicroConf and now TinySeed, did this:

https://robwalling.com/2015/12/02/what-i-learned-buying-growing-and-selling-my-startup/

https://vimeo.com/70901901

Now instead of buying the company, you can simply do the same for free via repackaging the open source project.

If you have design or product mindset, then the idea of spending a few weeks to launch products make sense.

One good reference is the "stair step" approach. You can make something that a few people will pay $50-$100/month for. Maybe like a theme or a designed landing page. Then you can ramp up to make something that does $100-$250/month. Once you have those two, then aim for something that brings in $300-$600 month.

If the 1000-1500 range seems daunting, then aim for an intentionally low, but consistent amount, then repeat.

Link: https://robwalling.com/2015/03/26/the-stairstep-approach-to-bootstrapping/

Big fan of Rob and his work, for those unfamiliar with him he's one of the founders of MicroConf, half of the "Startups for the Rest of Us" podcast and built and then sold Drip (an Email Service).

Whether or not you're seeking to build your own microsaas or you're going full VC funding I feel pretty strongly that you'll see the time spent reading his book as worthwhile.

Here's a direct link to it (it's not gated on his site, so this seems fine to share)

https://robwalling.com/assets/ebook.pdf