Happy Saturday!
I typically open this newsletter with a photo of a sunrise or beautiful landscape as a palette cleanser. Something to reset your brain and invite you to take a breath before engaging with a few new ideas as you move through your inbox.
The featured photo on this one in particular is special to me. It’s a photo of a gorgeous setting centered on a bridge on the lower Deschutes River here in Oregon. I take a three day guided fly fishing trip every year with eight friends. There’s no cell service, we fish all day, and we enjoy hours of companionship and conversation.
So it’s an original photo this week, which I hope to share more of going forward. I have a big catalogue of iPhone photography of landscapes and natural beauty that my wife has encouraged me to share more of. (Thanks as always for the encouragement, love, since I know you’re reading.)
On Remembering Who’s In Charge and Making Clear Requests
My friend and former colleague, Nathan Barry (CEO at ConvertKit), was in town a couple of weeks ago. While he was here we had a long dinner to reflect on our five years of working together to build ConvertKit to $30M in annual revenue and 75 teammates. The next morning we recorded a podcast conversation with our takeaways.
(We recorded it as a crossover episode, so it will come out in the Good Work feed in a few weeks.)
There was one thing in particular that overlapped with a coaching session I had this week with a founder. It’s related to this question: Who’s in charge?
In our conversation, Nathan joked that his coach will sometimes ask him a question: “If you were in charge, what would you do in this situation?”
You get it right? Nathan is in charge. His company is privately held. He is the majority owner and CEO. There is no decision-making board. He is in charge. But there are times at which he feels like he is subject to the needs, desires, or decisions of the people on his team.
Another example of this is when you hire a contractor or agency to support your business and team. For example, I work with a production agency for my podcast. Let’s say in addition to producing the show, the agency were responsible for landing sponsors for the show (this is not true for me).
The agency comes to me and says:
“Hey, here’s our revenue target for your show. We think we’re going to need four sponsors for every show with a pre-roll, mid-roll, and post-roll read on each episode (that’s 12 ad reads per episode). Oh, and the sponsors you want aren’t available so we’ll just have to take who we can get.“
In this hypothetical example, here’s what I might have asked for from the agency:
- Two sponsors per episode
- 65% of the agency’s target revenue
- More revenue per sponsor
- Targeted sponsors aligned to my values
The way many founders react to this is as if the agency is in charge. So you as founder, say “Ok” and then immediately start feeling the stress and dissatisfaction of that “Ok.” (You could imagine a similarly frustrating situation where one or more employees is substituted for the agency and a different set of asks.)
Why the stress? Because you’ve accepted terms that are misaligned to your vision and values.
What is there to be done?
“That doesn’t work for me. Here is what I need from you.”
And then you reiterate your requirements. YOU hired THEM. They are not your boss. You are their client (or boss in the case of employees). In the absence of clear, strong requirements, people will fill the gap with what works for them.
You don’t have to settle for what works for them. You are the founder. You are in charge.
What makes this work is when you ask yourself: “What’s my next best option?” In this example, your options might be:
- Do sponsor outreach myself and prove that it’s possible to meet my own requirements
- Hire another agency to handle sponsors
- Make an internal hire to manage the podcast
So you know you have options, which means you can confidently push back and reassert the requirements. Here’s what that might look like:
“Thanks for the note. This doesn’t work for me. Here are the requirements we agreed to when we began our work together:
- Two sponsors per episode
- $5,000 per sponsor
- From this list (link) or companies adjacent to this list subject to my approval
I understand this is a clear, but strict set of requirements. I’m happy to give you 60 days to ramp up to this. If by [60 days from now] we can’t meet these requirements, I will plan to end our relationship and take over sponsor outreach myself or find a partner who can make it happen.
Grateful for you and I appreciate how much hard work has already gone into our partnership. Now let’s find some great partners together!
Let me know if you have any questions.“
They have three options in response:
- Accept your terms
- Attempt to renegotiate
- Fire you as a client
And you have full agency because you know you’ll be ok no matter what they decide.
You’re in charge. Don’t forget it!
Question: In what scenarios are you feeling like a subject or victim, but you’re actually in charge?
How Matt Mullenweg Became the Person Capable of Leading WordPress to Power Half of the Internet
Matt Mullenweg has built one of the most consequential technology companies of the last decade. As founder and CEO of Automattic, he’s helped WordPress grow to power almost half of the internet and grown the company into a portfolio of high impact products (Day One, Pocket Casts, WooCommerce, Text.com).
There were two segments I especially enjoyed during our conversation. The first was on Jazz and how it has influenced the way Matt thinks and leads. He’s a saxophonist and we got into a deep dive on the background structure of Jazz performance + the improvisation that makes it interesting and fun for both performer and audience. I learned something about music AND leadership.
The second segment appeared as if it was going to be a nerdy deep dive on web languages and why PHP powers WordPress despite its disdain from many developers. Instead, we used the decision to build on PHP as a jumping off point for how seemingly small decisions as a leader can has massive downstream impacts on strategy and growth.
Here’s that 10-minute clip, which you can watch on YouTube:
Question: What seemingly small decisions are you currently facing that could have big long-term implications for your business?
Notice the Inner Response to Your Business (and Personal) Relationships
I recently read a memoir called Becoming Myself by an 85-year-old psychotherapist named Irvin D. Yalom.
In it, he shared many gems I took away to apply to my own work with founders, but more than anything I found his story inspiring at the whole life scale. He has written multiple popular books, published groundbreaking studies in his field, and worked with thousands of individuals to help them overcome challenges. All of this while remaining married to his beloved wife, a fellow author who recently passed away.
This quote on client work struck me as true far beyond its specific context:
Even now, after half a century of practice, I generally look forward to each new session, whether individual or group, with anticipation about what new developments will transpire. If that feeling is absent, if I approach a session with little anticipation, I imagine the patient may be experiencing a similar feeling and make an effort to confront and alter that.
– Irvin D. Yalom, Becoming Myself
Question: Which relationship(s) are you dreading or resisting right now? Which clients, customers, teammates, friends, or family are draining you? What needs to change?
Four Tweets to Move You Forward
1. Are you relating or handling?
2. Tell Your People You Love Them
3. What’s the story here?
4. There’s Always Time for Beauty
Have an awesome weekend. Do something that brings you joy. Love on someone you care deeply for. Create beauty. Deepen your connections. Read a good book. Be yourself.
Much love and respect,