First Podcast

Listen here

2 weeks ago, I went on my first podcast which was a bit nerve-wracking. Initially, it was planned to be a 45 minute episode. However, I recommended the hosts do a 15-minute episode that’s easy to listen to and has the potential of serving as a biographical snapshot of my life at this point and how it might make sense to have ben on again to see how things have changed. Especially for people not famous for something yet. 

I hope you give it a listen but also I look forward to listening to this again in a few years. 

Show notes:


2020 Opendoor Layoffs

Yesterday was such a painful day. Opendoor, where I worked for three years, had to lay-off more than 35% of their workforce. Even though I left a few months ago, the pain felt very real. To try and help, I started a spreadsheet for the folks who were impacted to find their next home faster. If you're hiring, I'd highly recommend reaching out to folks on that list - Opendoor was a talent magnet and they had easily the best people I've worked with. You can tell because that spreadsheet has morphed into so much more - people offering each other resources, answering questions, and providing support. Grateful to be a part of such a strong community.

2020 W15: Exploring something new, Tool(s) du jour, and interesting links

Moving some posts from Wordpress to Substack

COVID-19’s impact has changed so much. There’s millions of people or the 10’s of thousands of small businesses across the world who’s trajectories are now changed forever – mostly negatively. I remain hopeful that this will make us stronger in the long-run even though it’ll come at a tremendous cost. 

Exploring, differently 

While the above is true, I also don’t want to only think and talk about COVID-19. Since the middle-of-March it’s taken up almost all of my brain space but in a non-constructive way. 

My plan for 2020 was to explore new places, meet people who’ve lived very different lives, and learning about business that don’t depend on being at the forefront of technology adoption. This year was suppose to be an opportunity for me to explore where I wanted to live, take a lot of pictures, and nail down which kind of businesses would give me the most energy. With travel now out of the window and no forseeable path towards freedom of movement worldwide, I’ve decided to start exploring working on some new things to work much ahead than planned. Over the next 6-9 months, with a few others, I’m hoping to put together initial version of products that could become very exciting. 

The first idea on the agenda is bringing message boards into the future and how we work today (think Google Groups re-imagined). If you’re interested in collaborating in any way: expressing your frustrations with google groups in your org, giving feedback, wanting to build together, etc. please do reach out: 

P.S If anyone wants to pair on Figma with a complete noob, I’m available. 

Tool(s) du jour

I tweeted a few weeks ago about how status on twitter drives a lot of productivity app adoption in its earliest days. Your latest to float to the top is: Roam Research,, Pitch, and Linear.

While turnover of tools for something better, in general, has been true since the spear days, but I’m surprised at how quickly things are moving in some parts of the stack of personal productivity. This has me pretty excited tbh both as a user and as an investor very interested in tools that make how we work. 

One thing though to think about is that while it’s been easier than ever to build new tools, the bar for customer experience (design) and feature parity remain higher than every. This often means that what we’re seeing getting distribution now has taken about 2-3 years at least to build if not more. 

One implication of this to me: While NYT wrote about the “fat startup” being relevant for full-stack startups when talking about Opendoor, I think its going to become more of an option for productivity software as well. A few data points of companies building for a few years + raising $10mm pre-launch: Coda, Superhuman, Pitch

Interesting links

Experimenting w/ Organizing My Time

Reflections on a "free for all system"

Over the last three months I decided to experiment with a different productivity system as I am now accountable only to myself: a free for all system.

No longer did I set time to work on certain things, schedule calls more than a week in advance, or even plan for specific goals. My intention was to wake up and roughly let my intuition guide the coming day / week. I got rid of mostly using my favorite task tool. Outside of one project that I am collaborating on with one person - there's been no structure.

  • Outcome: The experienced has been mixed (as with almost anything). Though I'd like to think that the experiment would have had a better chance if I hadn't gone in thinking it'd be the utopian way of existence.

  • Positives: The lack of structure gave way to flexibility and newfound serendipity. Some highlights include going on impromptu roadtrips, more phone calls with friends and family, getting started on a new project when it felt right and also making a new investment. Some days, I finished a book / tv show end to end in a single sitting (which I've probably not done since college). All things that I feel so happy about.

  • Challenges: However, it also made me feel directionless personally. I felt like a buoy floating in the ocean: enjoying the sunny days, but also getting beaten up by the storms as they came by. Many days flew by without anything getting done, gaps altogether. I also felt more FOMO, funnily enough, because I could now second guess how you spent any time, all-the-time. This lead to some internal strife.

I am glad I tried this. I now know more about what works and doesn't work for me as I think about organizing my time and life.

I need some structure where I know how I am spending time doing what bucket of things towards which goals, However, I want to enable more of that serendipity as well. To accommodate this, my rough plan is to go back towards the my rigorous approach I had to my calendar but to have one weekday and and one weekend day unplanned and free, always.

Have you experimented with anything new in your own productivity system recently?

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