Tee up Paper Tigers, Thrice
Authenticity (2022)
Leadership manifests itself in many ways. There are endless flavors of leadership, and leadership is generally tailored to the unique personality of the person leading.
If I had to pick two leadership styles that have inspired me, it'd be that of Kobe and Ted Lasso.
Kobe - leading through a ruthless pursuit of excellence through hard work
Ted Lasso - leadership through optimism and positivity
Two totally different styles.
But the thing that connects them is the extreme version of their leadership style.
Kobe and Ted Lasso are extreme in how they lead.
Authenticity is the centerpiece to how I lead.
I'm keen to pursue an extreme version of authentic, because I feel it's tailored to my unique personality.
I want to show people that --
You can succeed being the truest version of yourself. I want to be the proof in the pudding.
You can show your flaws, that's honest. We are all flawed.
You can be weird, that's cool. Most of us are weirder than we let out.
You can brag, that shows passion. I love it.
I don't need everyone to subscribe to being authentic. It isn't for everyone, but most people I interact with appreciate that about me.
I want to approach authentic with an extreme lean. It's how I can leave my mark. I want that to be my seed of influence. An injection of raw, positive, and refreshing energy into the world. Even with a small sphere of influence, I believe I am making an impact by how I approach it. I feel good about that.
This bridges to how I do my job. My job is about relationships. Authenticity front and center.
I want you to know who I am as a person. That's the source of quality relationships. Internal or external, inside or outside of work, you get me.
I'm emotional. I'm passionate. It works in my favor. It also works to my detriment. I'm good with that.
Let me tell you about my weekend.
What do you do for fun? There's very likely a connection point, let's find it!
Why isn't my shirt on? It's hot out!
I want to be your friend.
We will have more fun working if it's bigger than work. Winning together. As friends.
::
Tee up George Shearing Trio, currently spinning.
A Letter to a Friend (2026)
This is a brain dump on the value of being a cool dude who can shoot the shit -- to a friend who is looking for professional direction. I think a lot of this ties to authenticity. The main line here that guides this --
writing is massively underrated in the world of business. That's a skill you could really lean into. Weirdly, I think that "writing long and thoughtful emails" is maybe the single most relevant thing that I do in my job. It's how I drive relationships internal and external.
I write probably ~5-10 long thoughtful emails (internal + external) every day. It's how I progress relationships. We have a call, I think about it, I write a really nice summary over email. That typically leads to the next conversation, and all the relationships have a long term scope. It's not transactional with the people I work with, or my clients.
External -- I was at Kiva for 5 years and I've been at Wefunder for 7 years (I was at LinkedIn for 15 months). In any conversation I have with people about sales, I describe there being two types of sales. The type of sales I did at LinkedIn was short cycle and transactional. The type of sales I've done with Kiva and Wefudner is long cycle relationship. That to me is how I see the split of sales and business development. The further it is in the business development side of the spectrum, the more important the relationship is to the sale.
Internal -- The other side of that is being a leader in the company. Helping with hiring and onboarding and development and team retreats and one on ones and team meetings. This is a huge part of my job. If there's one common thread it's just like
-- "be a good dude that can shoot the shit"
-- "actually give a shit about others, and take interest in them as humans"
-- "be nice, be encouraging"
If I were to split that first bullet into two. I see those as your two biggest strengths --
1) Good dude -- I believe you to be a very genuine, sincere, and kind person. This is the most important thing (in life).
2) Can shoot the shit. To me, your greatest strength is your gift of gab. You can chop it up with anyone about anything. You're incredibly dynamic in how you communicate and connect with others. You set a very good first impression. People like you and it's easy for people to like you.
How this translates into professional insights and direction --
1) Long term, relationship sales. When making friends with the people you're selling to is key. Having many conversations over an extended period of time. And working with people you want to have many conversations with over an extended period of time. You are the type of person that fits cleanly into the "this is someone I'd enjoy working with over the course of the next year". Keeping an eye out for things that involve a long sales cycle, where personal relationships factor into it. I think you'd be good at that.
You could also reverse that direction and look at an internal corporate job. Let's broadly define it as "office manager". What that really means is someone whose job it is to be friends with everyone and throw holiday parties and organize cornhole tournaments and just help out around the office. Every company has one (or multiple) of those guys. Culture hires are a big part of hiring in the startup world.
2) Short term, vibe sales. I could see that as something like a bartender. Setting a chill vibe from the start of an interaction, shooting the shit, making people feel comfortable, making people laugh. Or maybe something like "luxury sales". When I remodeled my house, the main decision on who to hire was "who do I want to work with over the duration of this project". Or buying a house, the realtor is a homie who I can chop it up with. Or if you're selling box suites to corporate accounts from Levi's stadium. Or selling memberships at a private golf club. Or selling luxury golf vacations. There's probably a million random examples of this.
I think in all these areas, the skill set of "good dude, can shoot the shit, good writer, funny, smart" comes at a luxury.
I think in theory "can shoot the shit" wouldn't be classified as a professional asset. But in practice, "shooting the shit" is a skill set in high demand. You want to work with people you want to be around.