3270 6:33 Weekend Workshop

Weekend Workshop: From Rock Bottom to Business Empire

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: a British woman goes from living in a shelter to running a million-dollar business.

6:33

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Episode 3270

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This transcript was generated from the episode audio and may contain minor errors.

[Music]

What if being a teenage mother living in a homeless shelter could actually become the foundation for a multi-million dollar business? That is exactly what Naomi Dunford from the UK accomplished when she transformed her desperate circumstances into the motivation for creating itty biz. Welcome back to Side Hustle School. My name is Chris Guillebeau, your host. This is a segment known as Weekend Workshop.

We're gonna title this one from Rock Bottom to Business Empire. The segment is all about helping you learn the key steps to a new hustle, one step, or concept per week. It includes activities, examples, and more. We're using the book, Side Hustle, from idea to income in 27 days, which is available wherever books are sold. And for the first half of the year, we went through the 27 steps in the book.

Now in the second half, we're looking at more detailed case studies so you can hear and understand how people apply the framework. So I'd like to give you these little inspirational stories as we do and give you some practical steps, maybe some grounding for your first or your next side hustle idea. So let's talk about Naomi. Naomi's actually a friend of mine. I haven't talked to her many, many years, but long ago I used to know her.

She was one of the original bloggers in the cohort that I kind of came up with, 2008, 2009, '10, et cetera. And her story, as I noted, actually began in a homeless shelter. She was a teenage mom, a high school dropout, facing a future with seemingly no viable options. So the statistics were stacked against her, but Naomi had hidden advantages. Her dad had built several businesses, her mom worked in marketing, and her grandfather had been in advertising.

So she had this kind of DNA business thinking, even if her circumstances suggested otherwise. And so after she stabilized her housing situation, she made a big decision. Instead of seeking traditional employment, she started Itty Biz with the tagline, marketing for businesses without marketing departments. Pretty good tagline, very memorable. I also liked the branding Itty Biz, I-T-T-Y.

And the service was pretty simple. A one hour brainstorming sessions priced at $250. That was it. You're gonna have a one hour session priced at $250. Small business owners would discuss their marketing challenges and receive specific actionable feedback on immediate improvements.

So what made these sessions worth $250, especially like from a young person who didn't have a background with a lot of education? Well, Naomi could quickly diagnose marketing problems and suggest immediate solutions that business owners could go and implement basically the same day. So clients left with concrete steps they could take that same day or week to improve their results. And the sessions solved a real problem because small business owners had problems, they needed marketing help, but they couldn't afford expensive consultants. Her approach, Naomi's approach, provided legit helpful guidance at an accessible price point.

So that was the pitch. That was the idea behind Itty Biz. Let's take a quick break. When we return, what were the results, the outcome, and how might you apply this idea or this concept or this model to an idea of your own? [Music]

As Itty Biz grew, Naomi developed a distinctive no-nonsense approach.

She used kind of course language. She was very informal. She kind of broke a lot of business rules and norms that basically turned into an authentic communication style attracting clients tired of polished but unhelpful business advice. And her core message was really like, the goal of business is profit, not popularity. Like, I don't care about how beautiful your website is.

I don't care about how many social media followers you have. If you were trying to run a business, you need to think about profit. And she kind of focused her offerings and her guidance around that. So from these brainstorming sessions, Naomi then expanded into products, courses, and referrals, each offering built on credibility established through her consulting work. And in a short number of years, I think it was two or three years, Itty Biz reached nearly $200,000 annually and then crossed the million dollar threshold.

I don't think it was a million dollars in a year, but it was multiple hundreds of thousands of dollars in a year that added up. And her teaching focused on business fundamentals where she would evaluate each activity against one question, does this directly contribute to making money? If not, she would suggest you eliminate or minimize it. So this is very helpful, especially to small business owners who are kind of torn in lots of different directions and they're getting all this advice and they see all these videos, creators who are on dozens of platforms trying all this stuff. And basically she's like, does this contribute to making money?

If so, maybe we'll keep it. If not, eliminate or minimize it. So she had a transformative experience of her own from homeless single mother to successful entrepreneur, gave her credibility. And before long, she had lots of testimonials that she could then leverage as she built more products, courses and so on. So what about you?

I think this kind of approach of taking the lessons you have gained through struggle, really kind of honing it in a specific way, not offering just generic advice, but getting really specific about something, I think it works for anyone with practical expertise who can communicate clearly and focus on client results. The key is packaging that knowledge into immediately actionable advice instead of abstract concepts. And it's always helpful as a coach or a consultant or anybody giving guidance to just constantly ask yourself, what do people do with this? Like what, you know, if you've given them a talk or an inspirational message or, you know, again, a general concept, that's not nearly as helpful if it's helpful at all as saying, go and do this. Like here's a thing you can go and do.

So think about that today. What is the thing you can teach people to go and do? And as always, it's better to have a simple idea. You can start right away than a brilliant idea that never launches. IttyBiz.com is still up and running.

It's now run by a cat. Well, it's run by a persona, somebody who uses the persona of a cat, but they're still taking clients. And then Naomi herself has moved on. She is now at XXNaomi.com. That's like LoveNaomi, XXNaomi.com.

SighHustleSchool.com for every single episode we've ever had, 3,270 of them in fact, all completely free. Download, stream as you like. New episodes drop wherever you get your podcasts. Thanks for tuning in today. My name is Chris Guillebeau.

This is "Side Hustle School." [Music]

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