Hi there! Ryan here.

It's been a hot minute since we last posted here, and we're back. 😄 Both Greg and I had to take a few months to dive deep into our respective companies and make sure we were doing some foundational work to make 2024 a good one.

I'd like to share some reflections and updates from my side, particularly in changes I've been making behind the scenes to Second Wave Dive and Chief Design Officer School. Rather than write about it, here's a Loom video about why I needed to pivot, what some of that work entailed, and how those efforts will be a part of Jump Ship! If you prefer a text update, I've included a brief summary below.

Why I needed to put my CEO hat on

Stepping Back to Reflect

The past year has been a period of introspection and strategic shifts for me. After reaching a significant financial milestone with Second Wave Dive, I realized that despite the success, something didn’t quite fit. The majority of my revenue has been through selling intensive, 8-week courses. While the courses went great, the majority of my time and energy was spent trying to sell and market each. I had a thorough application process that involved filling out a form, scheduling a 30-minute Q&A call, and tracking the status of each application manually. For every course, I spoke with 60-80 people. With 3 courses a year, I was having the same discussion with over 200 people a year. This is not how I wanted entrepreneurship to be.


This imbalance led to burnout. The intensive cohort-based courses were very successful but very draining, both in terms of prep work and execution. Despite my success, the sheer energy and operational work it took to run these sessions was exhausting. I found myself lacking the energy I needed to keep filling up the courses, which meant I was not generating the kind of revenue I expected and needed to be bringing in. Running my own company has not meant I've avoided burnout. But, running my own company has provided me the ability to do something about it while continuing to keep the money rolling in.

Time to be the CEO

Realizing the need for something different, I began to rethink my approach. After 4+ years of putting all my energy into being a good teacher and coach, I realized I exceeded all my expectations in those areas. But, I was struggling to put myself in the best position to teach and coach. I needed to get better as the CEO. I had been putting off some key foundational work, but I had to make the decision to reevaluate my offerings and how I marketed them and make it easier for people to buy things from me that I had already created. I needed to update my operations and marketing so that my products were easily accessible and required less direct involvement of me to get the sale.

Making it easier for people to buy from me

In 2023, I decided to separate my work with Design Leaders into a new brand: Chief Design Officer School. For the last three months, I've been defining clear product variations, building sales funnels, and creating a more systematic approach to managing customer interactions. This included categorizing each offering as a distinct product and developing a comprehensive database to track customer engagement. While somewhat nerdy, these efforts have helped me make it easier for clients to understand and purchase my services. And it's working.

Results and Reflections

In the last two months, I’ve managed to reduce the energy I'm putting into each sale and sales are happening. I managed to finally release my second book (Play Up Your Impact) and have a clear understanding of how that book fit into my broader strategy. Over 1500 people have downloaded that book in a week and that's 1500 more people who know what I offer. People are purchasing CDO School from me with less direct involvement from my side. This success has been a relief and a validation of my efforts.

How it becomes part of Jump Ship!

As I look forward, I’m excited to continue sharing what I've learned and my experiences with you. The journey of an entrepreneur, especially as a ‘company of one,’ is filled with unique challenges and opportunities. I hope that by sharing these insights and, frankly, many templates, exercises, and conversations, we can help you navigate your entrepreneurial path with a bit more ease and foresight.

Greg and I don't have all the answers, but we are committed to being in community with you. We want you to feel supported as you explore this avenue, whether or not you eventually start your own company.

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