Hello.

Well, here it is, the first edition of Revenue Diaries. I debated starting with “Dear Diary” but thought it was too on the nose. 

So, let’s start with thank you. Thanks for subscribing and agreeing to share a small part of your Sunday evening with me (or Monday if you are hanging on the other side of the world, hey Simon).

And a reminder… this newsletter is a snapshot of my week…, including what I’m reading, experiencing, and learning. The content will vary from marketing to parenthood, exercise to history, and everything between. 

It just depends on what’s in my head. And my head is an interesting place, I think. :)

Kyle

On Sharing Before Ready & Board Meetings

I had the opportunity to work for Max Yoder at Lessonly, one of the more level-headed, empathic, and human-centric CEOs I’ve ever had the pleasure of working and building with.

Max wrote a book called Do Better Work, where he shares lessons learned while building Lessonly. It is required reading for me once or even twice a year. 

One of the chapters in the book is called Share Before Ready and is one of the more important values I’ve reused multiple times throughout the years… especially when I’m preparing for a board meeting or working on a meaty, cross-functional project.

What does it mean to share before ready?

Do you want gold? I know I do. Unfortunately, when I decide to power through and silo my work, or deliver a polished, finished product without feedback…I deliver bullshit. 

This hasn’t been more true than when I started at Jellyfish and prepared for my first board meetings. Long story short, I was delivering shit, not gold. 

And the reason? I wasn’t sharing before ready. 

Thanks to Andrew Lau, my boss, and co-founder of Jellyfish, who has implemented our version of share before ready, called red teaming, where part of the executive team plays the role of a board member, asking hard questions and poking holes in your story. 

My first couple of board deck red teams were brutal. I felt like a failure until I realized they were just another version of share before ready.

I now welcome the red team. 

Enough of the shit, let’s get to the gold. I’ve adapted a section from Max’s book to give you six steps to work toward your own red team and sharing before ready.

6 Steps to Share Before Ready

• Step 1: Outline Your Ideas: Take 30-45 minutes to create an outline or a rough draft of your section's story. What are you trying to say? What point are you trying to get across? I usually do this in a Google Doc with initial themes and talk tracks.

• Step 2: Get Feedback: Get initial feedback from your CEO or manager, mainly about your direction and approach. From Max: Find people who will benefit from your project’s success, respect you enough to challenge your ideas, and have time to help. 

  • Note: This should be the outline, not a slide deck or rough draft of the actual presentation.

• Step 3: Build First Draft: Use the feedback to create the skeleton of the presentation. For me, this is the marketing section in the board deck. This should include the main points and supporting data. 

• Step 4: Red Team First Draft: Bring your CEO or manager back into the fold with additional peers. My first draft red team is usually with our sales leader, CEO, and another co-founder. Ask the team to challenge your assertions and data analysis.

• Step 5: Build Second Draft: Use the feedback from your first red team (great job) to create the first proper draft of your board meeting section. This will include charts and be more of a “final draft.”  

• Step 5: Red Team Second Draft: Introduce a fresh set of eyes to the second red team by bringing additional peers. For me, that’s our CFO or Head of Product, including the three from the first red team.

  • Note: It’s okay to have one-off meetings with additional people. I often set up a 30-minute meeting with our CFO to review my section. It doesn’t have to be a massive red-team event. 

• Step 6: Rinse and Repeat: Continue red teaming and adjusting until you feel prepared for the board meeting or the project has reached its final version. 

On Board Meetings (Part 2)

Speaking of board meetings, I love to learn more about structures and outlines from peers and how they present their ideas in board meetings. So, here’s my initial outline, which then builds into a slide deck:

• Quarter Highlights - What major wins can we celebrate? What about challenges? 

• Pipeline & Conversion (Source & Segment) - What did we create, and how well did it convert?

• Marketing Scorecard: What channels/sources delivered pipeline and how efficiently? 

• Competitive: How competitive are our deals (open & closed) and what are we doing about it? This section also includes loss reasons. 

• Next Quarter Plans: This is an optional slide. It could be covered throughout.

On Pushing Forward

Sharing before ready (and red teaming) can be exhausting. The most important thing to remember is not to give up, no matter what.

I recently read an excerpt about continuously pushing forward and not giving up, attributed to Brian Halligan, Hubspot’s co-founder.

Referencing Duke’s Mike Krzyzewski (google him): 

The thing that drove him crazy was when someone would miss a shot on offense and then compound it by making a dumb play right after on defense by taking a stupid risk to make up for the missed shot. You could hear him on the sideline yelling (imploring) after every missed shot “Next play.. Next play.” I used this method several times following unforced errors, including my own, to try to get the company to put the past in the past. I think it mostly worked. Thanks, Coach K. 

There will be many occasions when you want to take a stupid risk following a mistake or error. Don’t do it. Remember to breathe and reset; there will always be the next play.

On Weekly Winning

I have a love/hate relationship with Twitter (formerly known as X in my head). I hate the content algorithm, but love the random nuggets I receive from people like Dr. Julie Gurner and Sahil Bloom. Here’s one I implemented this week: 

On What I’m Reading

Elon Musk by Walter Isaacson (read all of Walter’s books)

Love or hate him, you can’t argue his influence on technology and the world. The book dives into all the complexities of what makes Elon, Elon.

Isaacson describes Elon’s tendency to enter a mental state he calls “demon mode,” where he becomes laser-focused and obsessive on a goal, often at the expense of personal relationships or social niceties.

While I’ll never condone extreme focus that tears people down or destroys relationships, focus is necessary when driving change or building a company or idea.

In a world of fingertip dopamine, we could all use the reminder to focus more on what matters.