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Playing With Networking (Weekly Recap August 30, 2025)

Playing With Networking (Weekly Recap August 30, 2025)

When Authenticity Costs Everything (And Why It's Still Worth It)

Matt Zeigler
August 30, 2025

Let's connect some dots from this week's notes...

This week was all about the courage to be authentic when it costs you everything - and why that's exactly when it matters most. From The Roots losing friends by calling out hip-hop's performative culture to Alchemist ditching the major label game for $20 PayPal payments, we explored what happens when you choose principles over popularity. Jenny Wood chased a stranger off a subway train into marriage, Preston Cherry pumps himself up every morning despite appearing naturally confident, and Bukowski reminded us that art happens in the balance between living and dying - even on Tuesdays.

Before we dive in, a quick reminder about newsletter preferences: You can adjust your subscription to receive just these weekly recaps instead of daily posts, or vice versa. Just hit reply and let me know your preference - I want to make sure you're getting exactly what helps you build your network and archive your insights.

Bukowski On What Art Is

Every day you live a little and die a little - art happens in the balance. Even on Tuesdays when nothing feels artful, Bukowski reminds us that creativity emerges from the excess in either direction. It's what you do with the net-living versus the net-dying that matters. For a guy with "Don't Try" on his tombstone, his insight is pure poetry: if you live a little more than you die, you'll continue creating pretty fair stuff. Life is exhausting - we've all got work, home, endless responsibilities without respite. But if you're exhausted, you're probably dying more than living, and you can do something about it. Doesn't have to be big, just has to capture some part of that living excess. Every post, every creative act, is an attempt to tip the balance toward the living side.

Quote from the Personal Archive - as Bukowski described the creative process

"Art is a day by day game of living and dying and if you live a little more than you die you are going to continue to create some pretty fair stuff, but if you die a little more than you live, you know the answer."

Sunday Music: What They Do Vs. What You Do (Questlove, The Roots, And Frustrating Missteps)

Sometimes standing for something means standing alone, and The Roots learned this the hard way. Their 1996 video "What They Do" was brilliant satire - calling out rap video clichés with sarcastic subtitles like "rented for the day" over mansion shots. But satire has consequences. The video devastated Biggie, a huge Roots fan, and when they later backed Jay-Z on MTV Unplugged, Nas called them hypocrites on Hot 97. They found themselves on a lonely island - too authentic for the mainstream, too successful for the underground. Yet "What They Do" became their first Top 40 hit precisely because their critique was true. Like Hugh Hendry calling out "champagne socialists" during the European debt crisis, being right early often looks wrong until it doesn't. Careers that last decades require getting comfortable with occasionally standing alone with your values.

Quote from the Personal Archive - as The Roots discovered about authentic stances

"This is the tension every creative faces: the urge to call out inauthentic BS versus the reality that you still exist in the same ecosystem. Sometimes standing for something means standing alone. Sometimes your principles put you in contradictory positions. And it's going to S-U-C-K."

Alchemist And The Death Of Mass Market Thinking

After 25 years chasing bigger features and budgets, Alchemist was burning out until he discovered Trent Reznor's formula: CWF + RTB = Success (Connect With Fans + Reason To Buy). Watching $20 PayPal payments roll in for a self-released instrumental album blew his mind. Instead of the traditional cycle of write-record-send-wait-maybe-get-paid, this was immediate. One day finished, next day in fans' hands, money in the bank account. The revelation wasn't about reaching everyone - it was about being irreplaceable to someone. Like running a microbrewery versus a mainstream operation, you can be local, have limited releases, and still be the most special thing for people who actually care. Success becomes project-based, defined by who has what connection with you and what unique reason you've given them to buy. Marketing is sales at scale, but you get to define what scale means success.

Quote from the Personal Archive - as Alchemist realized about true connection

"Our fan base is small but they love what we do... You can be local, have limited releases, and even without distribution - be the most special thing for the people who actually care."

The Art Of Ethical Ego-Feeding: Jenny Wood And Dr. Preston Cherry On JUST PRESS RECORD

Everyone has an ego that needs feeding - that's not controversial, that's human nature. What's controversial is learning to work with it instead of pretending it doesn't exist. When Preston Cherry quoted MLK about how everyone has an ego and it's about how you feed it for the greater good, it reframed everything. Manipulation, like ego, has been unfairly maligned - its Latin roots simply mean "skillful handling." Jenny Wood showed this in practice by rewriting a Google sales email, flipping from "I had so much fun training your team" to "Your team was amazing to partner with. You are clearly passionate about serving your customers." Same goal, different approach - the flipped version feeds the client's ego while achieving business objectives. When you skillfully handle situations so someone's ego gets fed while you achieve your goals, you're practicing ethical influence. It's about mutual value creation, expanding the pie rather than dividing it.

Quote from the Personal Archive - as Jenny described ethical influence

"Your ability to win friends and allies is all about mutual benefit. So figure out what someone else wants and go get it for them, and then you both win. You're expanding the pie, you're not re-dividing the pie."

Grow Your Network: Dr. Preston Cherry Is A Psychology-Powered Wealth Builder

Dr. Preston Cherry combines behavioral finance with practical wealth-building, bringing the psychology behind every financial decision into focus. Despite appearing naturally confident, he revealed that he has to pump himself up every morning with self-coaching because he doesn't want to hear the "no." Even the most confident-appearing professionals work at confidence daily - the difference is the commitment to showing up regardless of how they feel. His "emotional HSA" (Honest Self Audit) framework recognizes that we can't improve what we won't acknowledge. The mirror doesn't lie, and neither should we when examining our patterns and behaviors. But perhaps his most powerful insight came from comparing careers to Michael Jackson's journey - even legends spent years in "session work" at Motown, learning and developing their craft before commanding the stage. Every unglamorous role in your career is building the foundation for your eventual breakthrough.

Quote from the Personal Archive - as Preston explained about preparation for greatness

"Most people work for somebody... sometimes you're not building somebody else's dream. You're doing that session work to build your dream... Michael Jackson was in the basement, you know, Motown... that man was 22 years old. So he had all this session work to hone in on the craft and then you can go be great."

Grow Your Network: Jenny Wood Is A Wild Courage Catalyst

Jenny Wood chased a stranger off a subway train and turned it into an 11-year marriage - that's the kind of wild courage that changes everything. As a former Google executive turned entrepreneur, she helps people push through the three fears that hold us back: failure, uncertainty, and judgment by others. Her FLIP framework (Fun, Learning, Impact, Personal) gives you a systematic way to evaluate career changes - real growth happens when you have butterflies, when there are emails in your inbox you don't know how to answer yet. But her most powerful insight is about embracing your weirdness as your superpower. In a world of 8 billion people where everyone's trying to fit in, the competitive advantage goes to those who lean into what makes them different. Your weird isn't a bug - it's the feature that sets you apart. And her WINN framework (What I Need Now) forces brutal honesty about what you actually need at this stage of life, not what you thought you needed five years ago.

Quote from the Personal Archive - as Jenny explained about standing out

"Within your so-called weirdness, quote + unquote, lie your greatest strengths. So hone every ounce of weird you've got... in today's modern world of 8 billion interconnected people, where people are trying to make a buck or upsell a customer or get promoted, the world is too big and competitive for anything but audacious to make a dent."

Personal Archive Prompts

WHAT STANCE ARE YOU TAKING that might cost you relationships but defines your values?

Who are your true fans (not just followers) and what unique reason are you giving them to invest in your work?

How are you balancing net-living versus net-dying in your daily creative practice?

WHAT ASPECT OF YOUR "WEIRDNESS" have you been hiding that could actually be your greatest competitive advantage?

Which ego needs feeding in your next important conversation, and how could you expand the pie for everyone involved?

What daily self-coaching routine could prepare you mentally for the challenges that come with pursuing authentic goals?

HOW IS YOUR CURRENT "SESSION WORK" preparing you for the breakthrough you're building toward?

As always, I did my part, now it's your turn to write some reflections in your own Personal Archive.

(then, be sure to let me know where you're keeping it, I'm in search of the others too)

ps. Claude helped me organize and synthesize these thoughts from the week's posts. If you are curious how I use AI, read this post: Did AI Do That: Personal Rules