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Every two weeks, I share my writing on investing, career transitions, meaningful work, parenting, living intentionally, and other topics that engage me.

I'm still trying to figure stuff out.

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Let's Work Together

You may have read my recent essay, “Problem Solving,” which describes how I’m approaching what comes next for me professionally. Since then, and inspired by valuable conversations with key thinking partners, I’ve expanded my search to include fractional and full-time roles that leverage my skills and experience.

If you think there’s someone I should meet, I welcome an introduction.

For more, see the updated "How We Can Work Together" section at the bottom of this email.

Evolving Play

For many, the cooler, drier September air prompts memories of “back to school.” For me, it’s a bit different. This time of year always stirs memories of my days as a young goalkeeper on the soccer field.

Recently, I’ve rekindled that connection to a sport that has taught me so much over the years.

As a goalkeeper, I spent most of the game watching and shouting to teammates, always staying ready for those high-stakes moments when the game came my way.

While no longer playing, I’m still watching the game. And increasingly, my teenage son is sitting next to me.

Though he quit playing years ago, we've bonded over precise passes, creative runs, and big saves. His love for ‘the beautiful game’ has grown alongside mine.

I think it’s safe to say we’ve both become legitimate fans of Real Madrid. I know. It’s a bit of a bandwagon move. And for the record, we also plan to support Hearts of Pine SC when Portland’s professional soccer team kicks off its maiden season next spring.

Soccer has always held a special place in my heart. And now, later in life, the game has offered a pathway of connection to my son and still teaches life lessons regularly.

As we progressed from youth leagues to high school, the game got faster and more skilled. With maturity, we learned to think more carefully about timing, ball movement, and positioning. Eventually, I found myself leveraging experience over brute force. I relied more on angles, timing, and positioning than acrobatics.

As my playing days wound down, my relationship with soccer evolved. No longer on the field, I found myself drawn to the game in a different capacity. I began tuning into professional matches, at first casually, then with increasing interest. What started as a way to stay connected to the sport I loved soon became a fascinating study of strategy and skill at the highest level.

The professional matches I watch today barely resemble the sport I played as a kid.

I'm fascinated by how players create and exploit space. A run without receiving the ball can open crucial opportunities. Often, it’s not direct actions but unrelated efforts that create space for fresh opportunities.

This same concept applies to career development.

Like a midfielder creating passing lanes, staying active in my network often leads to unexpected opportunities. Likewise, standing flat-footed yields nothing, whether on the field or in one's career. It's about purposeful movement, engagement, and always remaining open-minded.

Recently, through dozens of conversations, I’m beginning to find more clarity in my next phase. An idea that wasn't on my radar before now feels almost obvious.

The journey from goalkeeper to spectator, from a reactive to a reflective professional at work, has been marked by dynamic movement - both on the field and off. Just as the game has evolved over the years, so too has my own approach to navigating life's challenges.

I'm struck by how the lessons I learned in goal continue to resonate. The importance of anticipating the play, of positioning myself to react quickly and decisively.

Because that's the thing about soccer, and about life - the most impactful moments often come not from the flashy, direct plays, but from the subtle, indirect movements that create space for something new to emerge. A run without the ball, a pass that opens up a lane, a shift in positioning that throws the defense off balance.

These are the kinds of actions that can change the entire complexion of the game.

In contemplating my next chapter, I draw on that same spirit of purposeful movement. Rather than waiting for the perfect opportunity, I'm proactively networking, exploring new avenues, and staying open-minded.

Hopefully, my son and I will continue to enjoy these matches together. For now, he’s focused on the sport. But I hope that over time, he, too, will appreciate that the lessons of the field—anticipation, positioning, and patience—apply just as much off the field.

Other Stuff

The Less-Efficient Market Hypothesis Here's a controversial paper making the rounds by well-known investor Cliff Asness, founder of hedge fund AQR. Asness argues, counterintuitively, that markets have become less efficient in pricing stocks over the past 30 years, leading to challenges for rational investing strategies. The conclusion suggests valuations have become more disconnected from reality, making traditional value investing approaches more risky, which should warrant higher expected returns. Here's the full abstract if reading academic finance papers isn't your thing.

​Read the research paper (40 mins)

Matthew Dicks: How to Tell a Story so That Everyone Listens This latest podcast from The Knowledge Project resonated on two levels. First, it's a masterclass on storytelling strategy and tactics. Second, you'll be treated to several stories used as examples that well exceed the cost of admission (well, it's free, but still). I replayed "The Spoon of Power" (from 6 mins) for my wife and kids, and it only gets better each time. Dicks is the author of Storyworthy, his first book that brilliantly weaves memorable stories with tactical lessons to help tell better stories.

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​Listen to the podcast (2 hrs)

No Regrets Jonathan Clements, author of the Humble Dollar blog and newsletter, has been writing some profound reflections on personal finance since disclosing his terminal diagnosis. His candidness about grappling with mortality challenges conventional views on retirement, emphasizing the importance of living fully regardless of life's uncertainties.

​Read the article (4 mins)

And a Farewell Photo...

How We Can Work Together

Hi, I’m ​David​. This newsletter is a passion project that helps me stay connected with thoughtful people like you.

I spent 25 years in institutional equities as an analyst, portfolio manager, and salesperson. In 2022, I joined Circa, a seed-stage rent payment startup, as COO. I left Circa in 2024 as part of our successful exit to ​Stake​, a larger private company in the proptech space. Also, since 2019, through ​Cove Investments​, I've been an active multifamily real estate investor for myself and on behalf of others.

Here are three ways we can work together:

1. The Right Full-Time Role: I’m exploring full-time roles working with great people where I can leverage my skills and experience in 1) managing relationships and processes, 2) evaluating, distilling, and communicating complex opportunities in simple terms, and 3) building teams and developing staff. This could be in the broader investment world, but it might also be in a new industry altogether.
2. Fractional Engagements: I’m also available for limited projects and fractional work. If you’re an emerging asset manager, investment advisor, or family office looking for additional resources to help with business operations and management, process optimization, or evaluating new opportunities, let’s discuss how I can help you focus more of your energy on your critical drivers: performance and clients.
3. Cove Investments: I focus on smaller properties in the DC Metro, a massive niche most investors overlook. Investment opportunities offered through Cove are only available to accredited investors in my network.

To learn more about any of the above, click to schedule a one-on-one call to see if we're a good fit.