TBM 339: Update and Clarifications

I've been getting a lot of questions about Dotwork, my relationship with the company, and how it relates to my newsletter. In the spirit of full transparency, here are the details. If you’ve ever wondered why and how I write this newsletter, you might find this interesting. It might also be interesting to people juggling full-time work and writing.

Money and Content

First, this newsletter is independent of my employer (Dotwork). I choose what to write here, and Dotwork does not pay me to write here. That’s why I’m here on a Sunday morning writing this post.

By this point, I have written this newsletter while working for three different employers. I am especially careful to draw clear boundaries between what happens at work and what I write about.

I do not have newsletter sponsors. I am an angel investor in three companies: TheyDo, DoubleLoop, and Enterpret. If ever I link to these companies, I disclose that relationship. My full-time jobs have each involved some form of stock compensation, so technically I am an investor in those companies as well.

Last year, I started running paid workshops on Maven and used this newsletter to spread the word. This was a huge step for me. Until then, I had never really "monetized" my reach or network. I’ll be doing more of those soon. I also started offering a paid subscription option to TBM in response to people asking how they could support my writing. Currently, 0.2% of subscribers currently pay.

What is Dotwork?

Let me take a moment to describe Dotwork. The reason I am describing the product is so that long-time readers can see how I’ve been talking about these themes for a long time now. This is not a pitch—figuring that out is on my to-do list. Apologies to the team for just winging this.

I am a full-time employee at Dotwork. The company is based in Austin, Texas. It is not an agency. I am not a founder. I receive stock compensation in addition to a salary.

Dotwork is a tool for strategy development and deployment, goaling, portfolio management, supporting planning and review cycles, managing capital allocation, high-level roadmaps, etc. I don't think there is a good category name—in product operations, we just call this stuff "the tools."

My current role is head of product, but at ten people, roles don't matter. It is full-on, and that is what I love about startups. I don't know if “stealth" is the right word, but we're focusing on really nailing the product with a handful of design and launch partners.

Our basic view of the world is:

1. Front-line teams should use the best tools for the job and configure those tools to fit how they need to work. An organization of a non-trivial size has teams tackling very different" "shapes" of work. Over time, these tools tend to get polluted by trying to customize them to do too many "jobs" for management and leadership, and they inevitably become franken-tools that do nothing particularly well. Let front-line teams use the best collaboration tools and make them their own!

2. Assuming we want companies to embrace #1, it is best to use another product to solve the problems I mentioned above (strategy development, etc.). That's what Dotwork is uniquely designed to do. It is better to use multiple best-in-class tools than single meh-all-in-one tools, provided they can be linked and mapped.

3. While common building blocks make up any operating system, companies should be able to customize tools like Dotwork to match exactly how they want to work. This extends to what they name things, what they choose to omit, the information architecture, etc. Too many companies get worked by tools instead of making tools work for them. And when conditions change, they should be able to change their tooling to match that!

I'm enjoying working there. Hopefully that background helps—I’ve been talking about many of these themes for a long time.

My Commitment

I don't wake up each Sunday and say, "How am I going to promote Dotwork?" But I often wake up on Sunday with my head filled with stuff I've learned that week and that I am eager to share with you. This is what I've always done.

One of the reasons I took the job was that it lets me spend the better part of every week nerding out with product leaders about how they work. The level of detail is on another level because the day job involves basically converting ways of working to an actual product.

Win/win. I did the same thing while at Amplitude. While at Toast, my focus was on one company, but I still picked things up.

As with Amplitude, sometimes I might invite people to a webinar or class if I think it might be of interest to TBM readers. However, I will always be transparent about what happens to your email when you sign up. I'll do the same with any research efforts or calls for research participants.

Finally

For almost 10 years now, I have been working, writing, and sharing on Medium, Twitter (now deleted), Cutle, fish, LinkedIn, this newsletter, the new YouTube channel, etc.

All for free.

Most of the time while juggling a full-time job, family, life, etc.

While I admire "full-time creators" who start businesses around that, I've never done that. I like to write. My "plan" has always been to embrace the idea that karma comes around. If you put valuable stuff out there, eventually, good things will come back. You can't predict how, but it will happen. This has proven to be true so far!

Thanks for reading.