Informed by Tension

Phu has been inspiring me lately with his aggressive book per week reading schedule, zero-complaint desire to push his body to the limit exercising, and self-imposed sales quota for his company. He's been waking up before me to meditate and work. He goes to sleep after me too.

I haven't had a roommate since college. It's been interesting. Yesterday Phu and I had a discussion about explore-exploit tradeoffs when getting to know people. Whether its via sales calls or organic intros, I argued, you want to broadly ask people open-ended questions about themselves which value their humanity and express gratitude and curiosity, opening a door to serendipity during the conversation.

His point of view differed. He felt it's better to directly go after people in alignment with his goals. If folks are not clearly aligned, then attempting to maintain any relationship is a waste of time. He gave the example of cutting off his friendships in Vietnam cold turkey to migrate to America, which required his full focus.

Our discussions often end with him accepting my views and learning from the extra experience I possess. But this time was different. His point of view was so strong, it forced me to ask why I felt the way I did. We discovered that I have a unique fixation on people, to the point where it even gets in my way sometimes. The tradeoffs I make getting to know people are not necessarily the right priorities for him.

The student often becomes the teacher, if your strong opinions are loosely held. But in my experience, one must deliberately hold space for difficult conversations in order to truly learn and forge a new path forward.

I crystallized this idea with Austin, who founded Shuffle Dating then recruited me as his cofounder. We had multiple serious disagreements—first about equity and voting rights, then with our third cofounder, again regarding voting deadlock, the extent to which we'd invest in team development and potentially date coaching lines of business, who should be CEO, minor details around my departure, etc.

We always had a healthy respect for each other and treated disagreements as opportunities to discuss ideas, rather than personal attacks. We had a pattern of me calling him to surface an idea or concern, him being skeptical and me being frustrated, then us talking again some days later. In the second or third conversation, he'd articulate the underlying principle behind my idea and take the concept even further to its logical conclusion. After we hammered out a game plan, I'd feel much better but still frustrated that Austin didn't understand sooner.

He'd point out how things were not super clear at the outset, and our conversation was both necessary and productive. He'd thank me for being transparent and giving him candid feedback. He called it "tension moving us forward."

We came to see our serious discussions as vehicles for sense-making when the business required us to reevaluate our underlying assumptions. We had to sort through what was personal friction versus business necessity. Thankfully, we were always able to navigate this while being respectful, playful, and on the same team.

But our differences where often rooted in our personalities. After working together very closely for over 2 years, through ups and downs, we found out a lot about ourselves. Austin discovered his niche being hands-on to innovate products. I discovered my obsession with cultivating humans and lack of interest in particular products.

When I started working on Shuffle, I had tons of leverage to name my terms. I was already mid-level in my career and almost doing Austin a favor by joining. But I saw immense potential in the idea and him. He likewise saw potential in me, and probably felt he was doing me a favor by giving away a huge chunk of the business. We were both close to fully formed as operators in our later 20s.

Given all that, it's easy to imagine letting ourselves stay the same throughout our collaboration. We might have not chosen to reflect and introspect when butting heads. We still might have made over a million dollars in revenue together. Perhaps we'd pat ourselves on the back a bit more than we do...

Even though our development was nuanced, I'm grateful we both found ways to evolve by bouncing off each other. My intuition is that this difficult shift from 95% to 97% quality will prove an order of magnitude more valuable than the business's financial outcomes.

Over the past year, transitioning from Shuffle to to our next ventures, Austin and I each up-leveled our ambitions. Our taste for success and how we navigate our journey as founders has become notably more refined. Because we understand ourselves more deeply, we can also interface with each other with more clarity and don't need to speak as much going forward. We have developed deeper levels of mutual trust and understanding.

Sadly, we're journeying solo and no longer cofounding together, at least for a while. But I'm glad Phu is stepping into his own. He's beginning to push me to think hard about myself at times. I think this is one sign of a great partnership.

Who have you butted heads with lately? And how does this tension shape your path forward?