A few months back Danielle and I were at a happy hour with colleagues from work. Danielle and I had both recently joined the company through acquisition, and were just getting to know the engineers. One of the more introverted engineers struck up a conversation with Danielle. After chatting for quite a while, he said to her, “I should probably let you go talk to other people; I must be boring you.” She was taken aback, because the conversation had been fascinating to her. She said, “oh no, it’s actually really nice to talk to you, as I wasn’t really looking forward to the superficial conversations you usually get at an event like this. It’s a gift when an introvert shines their lighthouse on you.”
When she relayed the conversation, the thought of an introvert’s attention being akin to a lighthouse struck me. As an introvert myself, I kind of take it for granted that any conversation worth having is one worth focusing all my attention on. I sometimes forget that a lot of conversation for people is a bit like skipping a rock across water.

Since hearing the metaphor, I’ve made a point of having more conversations that go deeper. I am only realizing this year that’s sometimes a unique gift for the person you’re with.
My friend Andy and I were catching up on conversation dynamics, and started realizing you can think of each friendship having a sort of depth chart. Is this the kind of friend where you’re stuck at the surface and maybe only able to go a few feet deep. Or is this a friend where you regularly dive deep into what he calls the well of life. If you want to really run with the idea, you can think of depth in all kinds of dimensions. How philosophical a conversation is might be one dimension. How emotional or vulnerable it is are other alternatives.
Taking a more active role in steering relationships into interesting waters has been a fun adventure this year. I feel like I’m still just scratching the surface of what’s possible.
From the Operators
In Revenue Financing + Traditional Equity as the Future of Startup Funding, David Cummings of Atlanta Tech Village laments that there is “too much money is chasing too few high quality deals,” and proposes a model called revenue financing as a potential solution. While I think that’s a very valid option for many entrepreneurs, there’s a deep flaw in thinking only so many unicorns will start in a year. It’s at least conceivable that there are more great founders than ever, and more markets for them to enter than at any point in history.
From the Investors
Jason Lemkin of SaaStr illustrates why management teams that want to IPO someday have to get good at budget discipline in Zoom Had a Burn Rate Budget. So Should You.
It’s fairly common knowledge that negative net churn is a huge driver in SaaS businesses, Sammy Abdullah of Blossom Street Ventures explains the equivalent in ecommerce.
Jeffrey Carter of West Loop Ventures couches accounting as essentially a backward looking lens on a business, and draws the interesting parallel that really news media is not so different than accounting. I think it’s actually worse, and too much news intake is a sure fire way to over optimize fear circuits in your brain.