Inspired by Derek Sivers’ Now page. What’s been happening and top of mind.

~August 2025

Surface Area of Luck

My last update came in December last year, as my parents were winding down their medical practices, my sister just had her baby, I was still working at Retool, unsure I was to do next.

There’s a strange balance in letting life ‘happen’ while trying to dictate the right direction. I was in a bit of job paralysis for many months - anxiously debating options, flexing into conversations for late stage venture recruiting, founding something myself, transitioning into product, taking a break. I was fortunate in timing, as an old coworker (who I wrote a bit for) reached out intro’ing me to Clay. I knew little about Clay at the time, but knew they were doing well with a few friends in my network having moved over.

It came together quickly → I talked to Varun, who intro’ed me to Jess, who had me talk to a few folks across the team. I went through a swift interview process after which I had some choices to make - either join on the Enterprise team, working with a smaller book of higher ARR accounts, or helping to build out the scale motion (supporting the longer tail of SMBs/startups). I thought about it, and contrary to popular choice, decided on scale. In my mind, I believed that I would get broader exposure to companies using Clay, seeing more art of the possible, creating more opportunity to pattern match and write up learnings to shape the product.

Clay’s been a fantastic step in my personal and professional life. In five months, I’ve gone on to my first formal ‘lead’ role (I don’t like the term manager, as I try to be more of player/coach and keep hands dirty) for the scale, team, I’ve made very close allies and partners across the org, and feel like my assumption for why Scale might have been a better fit was duly proven (in our latest GTM celebration, I was avoided ‘Voice of the Customer’ paper plate award. Yes, everyone received a small award, but this is one that means a lot to me and my work.

Clay is ripping, I love my team, and am trying to stay level in my mindset and direction, despite the many challenges that naturally come with growth stage startups.

Two broader takeaways:

• Lean into my strengths, and be myself. Don’t try to be someone else
• Continue to expand my surface area of luck

I know myself. I know I’m not (and never was) the strongest engineer. I know I didn’t get into exclusive APM programs that would create a long standing path in product. But I do know I am sociable, technical enough, love to write, and enjoy working with people and customers. I’m not afraid pushing internally for resources or asking leadership why they made a decision. These are helpful for teams, as long as they come from a place of curiosity and care (and they very much do!).

Re surface area of luck, Clay was the outcome of a confluence of factors - writing for Justin was my entry point to Clay, working at Retool helped to establish credibility, writing online has continued to serve the ‘human’ side of me. Of course, I did have to prove myself in interviews! But, all of these bets improved and expanded my surface area of finding and capitalizing on opportunities. There are arguments against this. Another take could simply be - ‘just be really good at your job and opportunities will find you.’ That is true. But

• I am in roles that are not as well defined (deployed engineering is a newer career, albeit ‘hot’)
• I don’t know what I want to do longer term, so want to continue to showing up online in ways that are not just tied to one specific career path.

kk that’s all. TLDR joined Clay, having fun.

Other

I often commit to more things that I have time for, then fall into a loop of not knowing which to prioritize. That currently also includes starting a podcast. Here was the spec: Operators Corner. If you have thoughts please comment.

i started reading a bit more thanks to a new friend in my life who enjoys reading (and started a book club!) and recc’d two great books (Trevor Noah’s Born a Crime and Tomorrow, Tomorrow, Tomorrow. I decided to buy a reading bean bag chair for the apartment.

My family along with nephew visited NY earlier this month. He didn’t sleep the best we had a fun time exploring neighborhoods and stuffing our faces. Something about Kai I deeply respect - he spends a lot of time busy, usually doing the same action over and over. In this case, we had a case of beers he diligently pulled out one by one (se image below) before then carefully placing each one back in the case. He enjoys clapping (mostly for himself) when he does such valuable work for us.

Pics

I was at a 4th of July celebration when I realized that my (new) iPhone’s images were significantly worse than the photos friends around me were taking. Someone grabbed my phone, made some changes to the preset filters, and since then I have been taking majestically high exposure shots. I am now having trouble taking normal images, but I enjoy 80% of this new standard.