Letter to Josh Doody: On Building a Luxury Business and Learning the Business and the Craft

Hi Josh,

I originally started writing this as an email reply to your email newsletter. But I’ve been enjoying writing public letters lately, so I thought: why not make this one public too.

I also want to share your 2025 Year in Review with a few friends who are building coaching and education businesses, and a public letter felt like a good way to do that.

First: thank you for sharing so openly and thoughtfully about your journey. I run a DWY business, helping skilled immigrants land jobs in Germany, and I’m in Year 2 of your 10-year arc so far. Getting to learn from your lived experience is such a gift.

Your reflections on shifting toward a luxury model especially caught my attention.

You mentioned two possible book ideas, and you asked for reactions… So here’s mine.

The luxury business book is the more interesting idea for sure, but it’s also complicated.

I run a DWY business. Part of me feels like I “can’t” go luxury for two reasons:

1. I’ve never personally held a role more senior than a first-line manager, so I question whether I can even help someone land more senior roles, such as Director- or VP-level roles (my version of ‘luxury’).
2. Like you, I love helping people build skills and capability, not just delivering outcomes. I sometimes worry that going luxury could pull me toward building a business that makes money, but isn’t one I’m proud of.

So your transition raised a few questions that I’d love your perspective on:

1. What made you choose the luxury path instead of going the other direction, i.e. low-cost, high-volume info products?
2. How did you learn how to negotiate packages far larger than what you’d personally negotiated?
3. How did you balance learning the craft with building the business?

As an early-stage founder, I often feel like I’m learning two hard things at once:

• how to build a real business, and
• how to get meaningfully better at helping my clients succeed.

Anyway: thank you again for writing such a candid and generous review. I found it very helpful both from a business and personal perspective.

Best,
Chiara