SYP Success Story: David Gerber


Hi 👋 I’m a husband and father of two teens based 10 miles north of Portland, Maine. Over the past four years, my life has been transformed both personally and professionally as I completed a career pivot and refocused on the vital relationships in my life. SYP played an important role in helping me build a more meaningful life aligned with my values.


25+ years in finance and recently pivoted to a fintech/proptech start-up.

David Gerber

What attracted you to SYP?

I discovered Khe and SYP through an online community called Ness Labs. Khe was hosting a workshop on productivity, which caught my attention as someone obsessed with productivity. I was constantly searching for the next strategy or hack to do more in less time. Khe’s career background and transition resonated with me. I hoped I could learn some neat productivity tips, but I really hoped to extract some larger insights from Khe’s personal journey.

The workshop blew my mind, especially the way described his own battle with the hedonic treadmill, a never-ending quest for “more.” I was hooked. I wanted to learn more about the SYP approach and registered for the next cohort.

Describe your biggest challenge before you took the course.

I worried that the course was meant for 20-somethings looking to build productivity systems for their online businesses. Having turned 50, I worried that I’d be “the old guy” in the room and not really fit in. I also had my doubts that the course would help me. I’d had a history of reading books, taking courses, and buying tools (Shiny New Tools) to learn how to address perceived gaps in my life only to fail in executing the solution. Often I already knew what I needed to do. The story of Tim and Tina has always hit me hard.

What’s the biggest impact of incorporating $10K Work and thinking into your life?

I realized that much of my energy was exhausted on either busy ($10) work avoiding more difficult high leverage ($10k) work. Also, the 5 whys process helped me reveal some deeper influences on my major life decisions. Since I’ve embraced a $10k mindset I’ve become more aware and intentional in deciding who and what gets my best energy.

The atelic versus telic unlock was also huge for me.

Did SYP help you discover new joys?

Yes. Absolutely. I’ve stopped wrestling with the endless quest for “more” and found joy in tiny moments. I’m regularly balancing my commitments from a healthier and more holistic perspective. Sometimes I even go on walks without headphones!

On a more basic level, I’ve become part of a like-minded global community filled with intelligent, professionally accomplished, and fiercely supportive people. I’ve made close friends and regularly rely on this group for their insight and perspective.

How are you better since taking SYP?

I can’t pretend that everything is perfect and that I’ve found internal happiness because of SYP. That said, I’ve become far more aware of unhelpful narratives that influence my actions, desires, and priorities. And that awareness is everything. With insights gained in SYP, I’m living a more satisfying life aligned with the priorities I’ve intentionally chosen.

Before SYP, what was the most frustrating part of your workflow?

Like many in SYP, I had always aimed to do more, to be more. Approval from others fueled a quest to reach an external version of success and often at my expense.

As I now realize, more is an elusive goal that cannot be achieved. And when I inevitably failed at doing everything (and perfectly), I was left feeling empty. This is all to say that my workflow lacked prioritization anchored by informed intention. With thanks to SYP, now it does.

After SYP, can you give us examples of things that are easier for you?

Sure. For one, I can evaluate projects, tasks, and opportunities and often say no to more. Saying yes to everything was a recipe for disaster. It still happens, but within my current workflow, that happens less frequently.

Another is that I now prioritize high-value, high-leverage $10k work. I schedule the time for these important activities that had historically been crowded out by easier $10 tasks. I’ve found that I’ve become less reactive, searching for check-the-box dopamine hits, and more strategic, taking greater ownership of my personal and professional life.

Where can people find you?

Feel free to connect with me on LinkedIn here. I also write a bi-weekly newsletter called Beyond the Cove that explores investing, career transitions, parenting, and other topics that engage me. You can check it out here.

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