Howdy 👋
Not every million-dollar business starts with a shiny revolutionary app or big funding round.
Sometimes it starts in the unsexy places—where most people don’t think to look.
Meet Tim Stoddart.
Tim's got your not-so-typical entrepreneur story, going from carpenter to blogger to agency owner to investor. Along the way, he built a portfolio of “boring” businesses—think service businesses, directories, media sites, and agencies. Together, they bring in a combined $6M+ a year.
This week, we’re kicking off a two-part series on boring businesses (next week: how a dad with a day job grew a side hustle into $27K MRR).
In the next 6 minutes, you’ll learn:
Why cash flow is everything
Why directories are the ultimate flywheel
Boring business ideas to steal today
Let’s dive in.
Show me the money
Tim’s mantra: cash flow = options.
Instead of raising funding or chasing an ambitious SaaS build first, he sold client services that paid from Day 1. That initial $2K/month retainer gave him stability to build.
Over time, his profits funded new plays: an addiction recovery platform (Sober Nation), a lead-gen/SEO agency in behavioral health, Copyblogger (a content marketing site he later acquired), and Digital Commerce (an ecom-focused SEO agency). Check out Tim’s portfolio (as of 2024) here.
“If you don't have cash, then you only have one option: be at the mercy of whoever it is providing you with the cash. That's why I've really stuck with service-based businesses.”
Start this week:
Package one skill as a monthly service. Tim turned basic lead generation into $2K/month recurring revenue. No need to be perfect. You’re looking for immediate cash flow so you can afford to take risks and say no to bad opportunities.
Dominate one specific industry. Tim focused exclusively on addiction/behavioral health marketing until everyone knew him as the recovery marketing guy. This laser focus makes you the obvious choice when opportunities come up in that space.
Publish your learnings daily. Tim's daily blogging about recovery and marketing built his entire network and client base. Really good documentation becomes your marketing, your credibility, and your thought leadership all at once.
Directory’s cut
Tim stacked his cashflow with “boring” businesses.
But what’s his favorite boring business model? Directories.
Here’s why: the marketing is the product.
Each new listing makes the site more valuable, which attracts more listings, which drives more revenue. That’s how his first site, Sober Nation, grew into one of the biggest recovery directories online for folks struggling with addiction. It ended up funding everything that came after.
Directories work because…
Network effects are baked in: Every new business you add is a potential customer, and it’s also fresh content that makes your directory more valuable to Google. More listings = better SEO = more traffic = even more businesses wanting in.
They’re local + scalable: You can start in a single city, then expand (e.g., “DenverRoofers.com,” listing only roofing companies in Denver). Once you dominate one niche in one city, you can expand to other categories or cities with the same playbook.
Low cost to seed: You can launch by offering free listings to build trust and fill out the site. Once traffic builds, upsell premium spots, featured profiles, or ads, turning what started as free into recurring revenue.
Think of your product in terms of a flywheel. Does each new customer make it easier to attract the next one? If not, how can you build that into your process? That’s your unlock.
Oh, and one more thing from Tim:
“Make it till midnight.”
Entrepreneurship feels waaay less overwhelming when you just focus on stacking today’s wins. Enough of those, and you could just end up with a multi-million-dollar portfolio… built from unexpected places.
👉 Check out the full interview with Tim here.
The Boring Business Bureau
Let’s talk boring business ideas. This (very entertaining) X thread and this Reddit thread are goldmines for inspiration.
Some of our favorites:
Self-storage. People love having way too much stuff. Rent out a concrete cube, charge monthly, repeat forever.
Pest control. Nobody likes bugs, so everybody pays to get rid of them.
Cleaning services. Dust and grime always keep coming. Wash, rinse, repeat.
Vending machines. Feed them Snickers and Doritos, and they’ll feed you cash.
One man’s trash just became your recurring revenue.
What’s the most boring thing you’re most excited to build?
Reply and let us know. You could just be featured in Part 2. 👀
❤️ & 🌮,
The AppSumo Team
P.S. Next week in Part 2: a solopreneur who grew a link-in-bio tool to $27K MRR.