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Grow Your Network: Daryl Fairweather Is An Intentional Investor
HOW and WHY to connect with Daryl
Matt Zeigler
April 18, 2025
For years, I've been connecting with interesting people and documenting insights that might help my clients and myself. What was once private is now (mostly) public.
People often ask: "How do you know all these people?" and "How do you connect these (re: random) ideas?" The answer is simple: consistent relationship cultivation and thoughtful note taking. My north star is trusting my instincts, my maps are the constellations in these reflections.
Find my Personal Archive on CultishCreative.com, watch me build a better Personal Network on the Cultish Creative YouTube channel, and follow me on social media (LinkedIn and X).
This approach has helped dozens of clients strengthen their networks and unlock new opportunities. You can:
Steal these ideas directly
Create your own combination that works for you
I can't promise you'll learn from me, but you'll definitely learn something with me. Let's go. Count it off: 1-2-3-4…
Do you know Daryl Fairweather? Chief Economist at Redfin, MIT and University of Chicago graduate, behavioral economics expert, and author of "Hate the Game: Economic Cheat Codes for Life, Love and Work"?
If not, allow me to introduce you. Daryl has been analyzing the housing market and economic behavior patterns for years, bringing a unique perspective that combines rigorous data analysis with real-world insights. I wanted to connect with her because she embodies something I value deeply: being thoughtful about systems and finding ways to navigate them that benefit everyone (EVERYONE. Just like Beyonce’s fanbase. Yeah, I said it).
Our conversation is LIVE now on the Epsilon Theory YouTube channel (and this Cultish Creative Playlist). Listen and you'll also get an extra revealing peek into how she thinks about everything from economics to career evolution to understanding the hidden games in everyday life.
In the meantime, I wanted to pull 3 key lessons from my time with Daryl to share with you (and drop into my Personal Archive).
Read on and you'll find a quote with a lesson and a reflection you can Take to work with you, Bring home with you, and Leave behind with your legacy.
WORK: Understanding the Game Makes You Better at It
"Games can be unfair, but if you know the ways in which they're unfair, then you can still win."
Key Concept: Recognizing the systems and "games" you're playing in - whether at work, in relationships, or society at large - lets you operate with more confidence and effectiveness. Being aware of the rules (written and unwritten) gives you power to navigate even imperfect systems.
Personal Archive Note-To-Self: I see the game of business development everywhere now. When friends/business owners/consulting clients struggle to get results from social media, I'm reminded of what Daryl would likely say: it's not about blindly following rules but understanding the underlying structures. I've noticed my most successful creator people don't just post content, they reverse engineer their thoughts from their actual closing conversations.
They ask, "What made my last three clients sign?" (if that’s their goal), and then they create content addressing those exact action points. It’s game theory in action! Similarly, when I transitioned from a big firm to an indie firm in the finance industry, understanding basics like the unstated rules of client retention (how personal relationships matter way more than firm brands) gave me the confidence to make my move. Daryl's framework helps me see these patterns with clients across industries, especially as it relates to content and marketing.
Work question for you: What "game" are you currently playing at work where understanding the unstated rules might help you advance or find more satisfaction?
LIFE: Your Outside Options Determine Your Inside Options
"How good your outside options are is largely what determines how good your inside options are. I was able to get a good job offer from [a major tech company] in part because I already had a job to rely on."
Key Concept: Your negotiating position in any situation - career, relationships, purchases - is strengthened by having viable alternatives. The best time to explore new opportunities is when you're already in a good position, not when you're desperate.
Personal Archive Note-To-Self: When I was getting ready to leave the corporate world for an independent firm (with all the flexibilities to do stuff like these interviews, posts, and consulting engagements I wanted), I took my sweet old time.
I had to complete an internal transaction at my firm that took years. I had to keep my profile down by having an anonymous Personal Archive (that wasn’t a conflict with my job, but also wasn’t part of my job so I only stood to annoy people who would think I was wasting my time). I had to know I didn’t have to leave except for the precise reasons I wanted to leave and so I put all my energy on solving for those details. That’s how and why I ended up at Sunpointe.
Like with Daryl (and even though it was a negotiation (mostly with myself), I had to start by locking down all the inside options that mattered before I could map them externally to where I wanted to land.
Life Question For You: In what area of your life are you negotiating from a position of weakness because you haven't developed strong enough alternatives? What's one step you could take to strengthen your "outside options"?
LEGACY: Sometimes You Don't Need to Act on Every Impulse
"Sometimes you don't need to act on every impulse."
Key Concept: Strategic restraint - knowing when to hold back, when to wait, when to observe - can be as powerful as decisive action. Building a sustainable legacy requires discernment about which opportunities and impulses to pursue.
Personal Archive Note-To-Self: If you had a time machine, would you tell this to yourself? To ease off on every single crazy impulse? I would. As my wife regularly reminds me, "You can't do it all. You can do a lot of it, or you can choose to do none of it. But, you can never do all of it."
I don't like the advice, but I accept it. The strategic restraint of what to say no to, when, and why is massive. In our conversation, Daryl talked about her grandma Norma - the first Black woman architect licensed in New York, involved in the Tokyo embassy and LAX Terminal 1 (and so much more) - and her passing down wisdom that shaped generations.
That legacy of selective ambition didn't happen by chasing every opportunity, it came from choosing the right ones. In my own family, my grandparents approach to life and work gave my parents room to put their own spin on things, and since they’ve all been a major part of my life, I’m making my own version up now. Over time, they all taught me this - that our impulses matter less than our intentions. It’s more often our restraints that shape what others will remember.
Legacy question for you: What impulse are you feeling right now that might benefit from strategic restraint rather than immediate action?
BEFORE YOU GO: Be sure to…
Check out her NEW book "Hate the Game" - and
Take a moment to reflect on all these ideas!
You have a Personal Network and a Personal Archive just waiting for you to build them up stronger. Look at your work, look at your life, and look at your legacy - and then, start small in each category. Today it's one person and one reflection. Tomorrow? Who knows what connections you'll create.
Last thing: Don't forget to click reply/here and tell me who you're adding to your network and why! Plus, if you already have your own Personal Archive too, let me know, I'm creating a database.