Can Claude Help Me Start a Business?

Is it cliché to say, “In this new AI world”? But in this new AI world, the internet is bursting with content on how to use AI to make money in a million different ways. The question is: how does this actually work in practice?

In parallel, I was looking to build a “side hustle” — and a possible transition to a retirement occupation — and thought, “Of course AI can help with this!” So I asked Claude for a top-20 list of low-startup-cost business ideas.

One of the suggestions was bookkeeping. I’d done some intro bookkeeping when I started my career, and I once planned to do a six-year CGA program before ending up in Information Technology instead. I love personal finance, and I have a rocking setup with YNAB (You Need a Budget) for my own money. So the suggestion was intriguing. For a person with a dozen harebrained schemes always emerging in his brain, bookkeeping actually seemed like a doable one.

So I set to work planning my new enterprise with Claude.

Claude’s almost-superpower (among other things) is that the answer is always “yes — and here’s a plan.” Claude helped me build out a systematic process to get me to my goal: not quite a traditional business plan, but more of a detailed, phased process. With that blueprint in hand, I set to work.

Without going into detail on every step, I’ve been following the plan, and I think I’m about 90% of the way to launch. I’m certified on QuickBooks, I’ve got a website, I’ve registered the business, and PST and GST numbers are on the way. Step by step, I’m getting everything done. Claude even helped me build “trial” companies to practice my QuickBooks skills on, and I’m almost ready to start soliciting clients.

That’s going to be the ultimate proof point. Setting up a business is the fun part. Acquiring customers, doing the work, and sending out that first invoice is the real proof — and I’m not quite there yet.

My intent here is to show some of the journey and be transparent about what’s working and what challenges I hit along the way. So far, AI (Claude) has been an excellent tool to get me started and focused, and I’m excited to post further updates as “Watermark Bookkeeping” gets officially launched!