About Charles Reynolds
I’ve spent my career at the intersection of sports business, leadership, and entrepreneurship—working inside fast-moving organizations, advising teams and founders, and learning firsthand how pressure, ambition, and uncertainty shape decisions.
Over time, my work has evolved beyond titles or industries. What consistently shows up is this: people don’t struggle because they lack talent or drive—they struggle because they lose clarity about what matters, where they’re headed or results they're after, or how to move forward without burning themselves out.
That’s where I focus my work.
I help leaders, founders, and high-performing individuals think clearly, align their actions with their values, and make better decisions when the path isn’t obvious. Sometimes that looks like strategic advisory. Sometimes it’s coaching. Often, it’s simply creating the space and structure for honest reflection and momentum.
Travel has played a quiet but important role in shaping how I see the world. Experiencing different cultures, systems, and ways of living has reinforced my belief that growth—personal or professional—comes from perspective as much as performance. That belief shows up in my work, my writing, and how I engage with others.
I care deeply about transparency, holistic sustainability, and lifelong learning. I’m drawn to questions around purpose, leadership under pressure, ethical and personal growth, and what it means to build something meaningful without losing yourself in the process.
This site is a home for my thinking—across leadership, business, life, and direction—and a place to connect with people navigating similar questions.
If you’re building, leading, or re-orienting or just exploring, I’m here to help.
Artificial Intelligence is one of the biggest polarizing topics. Artists hate it, business people or those needing quick spelling or research help may appreciate it more. I have this discussion a lot. There is a ton of recognizable slop and sloppy information provided by LLMs. I, like many of those leading A.I. firms are hoping for governing regulation as “the singularity” where machine intelligence surpasses human cognitive abilities is debatably here.
Over 10 years ago, I jumped into bringing automated, connected technology solutions (project management with some CRM components) to the largely still 80’s-like business environment of sports and entertainment. I saw firsthand how pulling people reliance out of disparate systems and streamlining work created next-level results – notable business lifts (ie, more sales), better service, more time for above-and-beyond ROI-driving activities and 47% average time savings (which skewed up to 70-80%+ for your system power players). I pitched the effect – but did so in a spreadsheet (a key collaborative productivity killer known for high error rates and organizational drag).
In the push toward modern efficiency, standard advice usually splits into two extremes: either buy another point solution to solve every minor friction point, or promise that fully autonomous systems will magically run your enterprise overnight.
Neither extreme reflects reality from my experience.
Technology doesn’t replace elite strategic judgment, customer intuition, or go-to-market execution—it simply frees up the bandwidth needed to apply them. When highly skilled leaders spend 15 to 20 hours a week acting as manual data bridges between CRMs, custom spreadsheets, and communication tools while trying to fight an influx of emails pouring through, the real loss isn’t just software spend. It is velocity, strategic focus, and personal time coupled with stress, angst and a feeling of constantly being caught behind the 8-ball.
1. Where Enterprise Velocity Actually Breaks Down
Operational drag rarely stems from a single massive failure. It is the cumulative impact of micro-friction:
Manual Data Syncs: Re-keying customer information, deal updates, or partner leads across disjointed systems. Hard-coding with manual imports hurts.
Context-Switching Overhead: Spending critical mental energy managing manual notifications and status tracking instead of closing deals, refining GTM strategy or working on the ideal build-out and “wish list.”
Response Loops: Allowing inbound leads or operational inquiries to sit for hours in a queue when the pipeline demands immediate execution, or multiple days or weeks to stand something up, train and mandate and police the team causes friction.
Automation and agentic workflows are not magic remedies; they are structural architecture. When applied to repetitive, rules-based tasks, event-driven middleware eliminates data entry errors and speeds up response times from hours to under 60 seconds. This setup keeps your team firmly where they belong: in the loop as the strategic decision-makers.
2. Measuring Your Operational Drag (Introducing Calculator V1)
To help leaders quantify this hidden operational tax, we built the TNTC Operational ROI Calculator (V1).
Instead of vague promises, V1 provides a clear, data-backed diagnostic of your team’s current operational friction:
Total Estimated Annual Waste: The hard cost of manual data re-entry and administrative overhead across your team.
Recoverable Monthly Savings: What your bottom line looks like when routine workflows are automated.
Capacity Gain: The exact number of annual working hours freed up for high-impact GTM execution, strategic growth, and life balance outside of work (*hint; which can be deployed to help discover purpose, pursue hobbies, be more present with family and friends – all things Finding Your True North and beyond).
Note: V1 focuses on core team capacity and manual task friction. As we continue building, future iterations will introduce dedicated modules for complex partner ecosystems, multi-stage RevOps pipelines, and custom agentic workflows.
3. What Comes Next
After benchmarking your current friction, the goal isn’t to rebuild your entire tech stack overnight. It’s about identifying the 20% of manual handoffs that cause 80% of your operational drag.
Once you submit your diagnostic, you’ll receive a detailed breakdown of your numbers alongside our Operational Architecture Teardown Guide to help you map out immediate, practical improvements and an invitation for a free assessment call.
Early on in my sponsorship management software days, I worked with a Coastal Plain League upstart group turning heads: the Gastonia Grizzlies and the Savannah Bananas, owned and run by an innovative husband-and-wife duo who pushed all the chips to the middle of the table early on in Jesse and Emily Cole. Our software work didn’t last too long because they made an aggressive, counterintuitive move: cutting out traditional sponsorship clutter to focus 100% on fan experience.
Boy, did that bet pay off. Fast forward about nine years, and what started as a bold risk has become a global phenomenon. Jesse and his team took inspiration from the Harlem Globetrotters and Bill Veeck’s promotional genius, blew up the minor league model, and built their own touring league. Today, they sell out 60,000-seat stadiums across the country, command massive secondary-market ticket demand, and draw fans into four-hour pre-parties.
At True North Team Consulting (TNTC), this is the precise ethos we preach: finding your True North, rediscovering your core purpose, taking massive chances, and putting fun first. When you stop playing by legacy rules that breed dead air, quiet compliance, or lukewarm engagement, the results don’t just improve—they skyrocket.
Standing in a packed stadium watching a pitcher throw a strike with a college logo (U of U locally) carved into his chest hair after quite the walk-out ceremony—flanked by a full band, hype-announcers, a hip-hop dance squad, superhero cameos, players jumping into the stands with the Pharty the Party Animals’ mascot and everyone else high-fiving kids throughout the game played in its own league with its own rules even—you realize how universal this need for genuine engagement is. Music clips run continuously swapping every 15 seconds. Former Major Leaguers forgo the “bigs” to step back onto the diamond just to feel that constant spark. Every half-inning offers a fresh reason to celebrate, and the team’s Bananas Foster initiative actively gives back by honoring foster families.
This experience hits at the exact heart of what we at Apres Leisure call the Third Place—that sacred space outside of work and home where we get the fulfillment that drives us in the other places. Whether you are out in the woods, on the lake, or standing in a electric stadium, these spaces allow us to disconnect from screens and remember who we actually are when we’re truly enjoying life. We also commemore the Legends made in the process – and every one of these cast members proved to be a legend to the fans partaking throughout the 7-8 hour hour timeframe for some of the crowd, many of which who came out each night here.
It’s also why this mindset aligns so deeply with the mission of Apres Leisure (visit “The Vault” here). Leisure isn’t passive sitting around; it’s the sense of fulfillment when purpose, legends, epic entertainment, relaxation and community impact strike all at once.
When you align your organization with its True North—stripping away friction and putting real human connection, energy, and joy at the center—you don’t just host an event or run a business. You convert passive observers into passionate followers, create unforgettable moments, and build something that truly stands out.
As an executive GTM operator and AI architect, navigating today’s automated applicant tracking systems has been a humbling paradox. The month of May just ended, but the conversation around mental health shouldn’t. This is a transparent look at macro economic trends, curveballs, the power of human compound interest, and why I am launching Apres Leisure today to fight the noise.
Everyone has so much going on, which makes it hard to sit down and “smell the flowers” as they say. It’s hard to keep up with the trends in greater society when it feels like your life is increasingly chaotic and you’re looking over your shoulder.
The month of May just ended, which is Mental Health Awareness Month. Safe to say, it gets less publicity than say October, which is Breast Cancer Awareness Month for example. Cancer hits so many with physical pain – not to mention the anguish that comes with it for families, literally of all shapes and sizes. Mental health, however, has always been stigmatized, cloaked and hidden. We are taught to put on a smile and deal with it, but to quietly suffer and not air out that kind of laundry. Back when, someone who goes to therapy was long considered “crazy” dismissively.
I’ll shine some light on the numbers. Spoiler alert: if you look at the trends across sources, mental health has been consistently getting worse and more costly no matter how you slice it (these charts were from studies done in December of 2023).
Also, not too surprising news is that the younger your generation, the more mental health issues you are facing as a general trend. Two-and-a-half years ago, 73% of people cited having a mental health issue in the past year.
A lot has changed since that time.
And for the record, it’s okay to not be okay.
Fair disclosures: I am married to a front-line social worker and crisis worker. Every single day, she and her peers navigate the compounding numbers of our unhoused communities, veterans, and individuals left short on answers and hope and have turned to suicidal plays. Witnessing their selflessness is a daily masterclass in empathy. They are the quiet, essential infrastructure holding our communities together, operating in a system that often feels like it has running out of human solutions.
Many of the youth today were taught that the path to success is paved through education (of which job-placement rates don’t support largely thanks to unbridled advanced in technology). Most probably haven’t heard of the artist Tupac, who was gone too soon. Tupac was an activist with SO many famous quotes, interviews and statements that remain relevant 30 years later, like the one below, “They got money for wars, but can’t feed the poor.”
To use a baseball analogy, I feel like I’ve had to face not only every curveball life could throw over the past few years, but every Paul Skenes “splinker,” slider, curve and heater (shout out to my Pirates, first sign of competitive life in ages). I absolutely know the feeling of being in that clear, growing majority.
As an executive operator who builds high-velocity GTM engines and complex AI data workflows, it has been a humbling paradox to sit on the other side of the screen. I know firsthand what it’s like to spend hours-upon-hours job hunting, matching keywords and navigating automated applicant tracking systems only to hit immediate auto-denials. It forces an honest calibration of what matters. It also makes me realize that while I am actively hunting for my next senior GTM, marketing, or strategic operations leadership mandate, the goal isn’t just to find a title—it’s to align with a team that values human clarity as much as velocity.
I am a believer in the power of compound interest.
I know that if I can lock in my alter ego mindset, escape in the mountains, get some ski laps and laughs in with friends, or spend some time with animals or in nature, that gives me some temporary reprieve. Meditation, deep breathing, down-time and escaping screens all helps – just ask the experts…to a point…
Even when I’m down, I try to count my blessings and remember that someone else has it worse. I’ve always tried to make someone’s day putting a smile on their face – be it asking my grocery baggers about the latest in their life and thanking them or being nice to the customer service people on the phone that deal with a lot of upset people.
The photo above at the top is from my time gig-working at a local music festival, trying to make people’s day with a quirky greeting at the gate with my man Julius. Julius spends time handwriting cards and gives them to random people for encouragement: mine was “You deserve all the wonderful things life has to offer. Share the love.”
This exact friction is why I am officially launching an all-terrain lifestyle project today called Apres Leisure. The brand was born out of a profound need for those special ‘Third Places’—the quiet mountain ridges, the ski laps with lifelong friends, the local brewpubs, or a festival gate with Julius—where we step away from the digital noise, find temporary reprieve, and transform to our legendary forms. We believe our apparel and gear can serve as physical artifacts to trigger the mindset needed to persevere. To anchor this mission with action, a portion of all proceeds throughout the month of June will be directly donated to frontline mental health initiatives.
Money isn’t everything. It won’t solve the world’s issues, but I believe that if we can make the effort to take the time to connect with people, following up and showing someone that you are thinking of them, creates traction and goodwill is infectious.
May is over, but that doesn’t mean the movement and momentum has to end here.
Be kind, divert some energy to someone else in the community and if they take the notion and do the same, that can start a movement, and could well become a trend in itself.
I didn’t just launch a lifestyle brand; I built an Agentic GTM Framework. In Part 1 of the Apres Leisure build, I reveal how I moved from ‘Generative Noob’ to ‘Agentic Architect,’ scaling a 0-FTE brand from concept to launch in under 90 days. If you’re ready to move beyond ‘using AI’ and start running an AI workforce, the signal starts here.
How the principles of Finding Your True North fueled a 90-day, 0-FTE brand launch for Apres Leisure (P1).
I. The Call: Incorporating the Philosophy of Finding Your True North
Every successful venture starts with a clear signal. In my book, Finding Your True North, I explore the necessity of aligning internal purpose with external execution. While continuing to search for my great next career fit, I took on a challenging consulting project. Launching Apres Leisure was the ultimate “stress test” for these themes. I had to move from a self-described “Generative Noob” (using AI for ideas and copy, probably the average use case) to an Agentic GTM Architect (using AI for execution), ensuring that the brand’s “True North”—the transition into the Modern Myth—was never lost in the automation.
II. The Struggle: Addressing Laundry List of Challenges
Moving from speaking about and pitching connected technology to implementing it firsthand (read: front-to-back-of-house) requires some real strategist-to-operator-level commitment. In addition to time management, here are a few of the top hurdles faced in the process:
Education Rabbit hole – transitioning from generative to agentic via certifications, video tutorials, prompt education, social platform feedback, tons of trial-and-error.
Resources – versed in The Lean Startup methodology, I played a very key role in standing up and scaling a bootstrapped company, new category, etc. Finding free ways to grow vs. using the magic bullets is a job in itself. Vendor choices can be extensive.
Feedback – driving advisor and peer opinions, pressure-testing, doing the research to build out the strategy + LOTS of generative AI prompts.
Uniqueness – pressure-testing the category, building out the brand accordingly with comps and differentiating factors in mind.
Dedication – going from non-technical to self-taught “vibe coding” Agentic GTM technical skills isn’t for the faint of heart. If you hit a wall 1000 times, you have to make sure to get up 1,001. When the Make.com scenario failed for the 10th time, I leaned on the ‘Navigating the Fog’ chapter of Finding Your True North to recalibrate the logic.
III. The Solution: O-FTE with an Agentic Workforce
To maintain a 0-FTE overhead, I originally deployed seven agentic workflows tied to key roles, which evolved. These weren’t just prompts; they were digital employees executing the “True North” strategy:
To launch with 0 FTE, along with a few key exec roles, I architected multiple ancillary agentic roles within the “Apres Brain” to handle the heavy lifting of a traditional GTM team. Here are a few of them:
The Lore Master (Brand & Philosophy)
Function: Synthesizes the core principles from Finding Your True North into the brand’s narrative.
Output: Developed the “Apres Access” Legend Ledger loyalty framework and the “Modern Myth” identity of the LeisureVerse, catering to those who want to take that feeling from the special/sacred “Third Place” with them.
The GTM Strategist (Market & Finance)
Function: Conducts competitive analysis and financial modeling.
Output: Engineered a pricing strategy that secures a prescribed margin while maintaining “leisure-class” accessibility.
The Automation Architect (Logic & Handshakes)
Function: Bridges the gap between disparate SaaS tools.
Output: Built the Legend_Ledger_Entry scenario in Make.com to automate data flow between Shopify and the Ledger.
The Product Designer (Iterative Creation)
Function: Translates lore into physical aesthetics using generative design tools.
Output: Rapidly prototyped and synced 67 unique products initially for V1.
The Logistics Lead (Operations & Flow)
Function: Manages the complex logic of print-on-demand fulfillment and shipping tiers.
Output: Structured the Standard Signal Shipping hierarchy with automated free-shipping thresholds at $80+.
The Wordsmith (Conversion Copy)
Function: Generates high-fidelity product descriptions and marketing assets.
Output: Created the conversion-focused copy for the Apres Leisure Store and the automated communication triggers for new customers.
The Efficiency Auditor (Overhead Control)
Function: Monitors the “Team of One” tech stack to ensure 0-FTE sustainability.
Output: Optimized the modular API strategy to prevent “tool bloat” and ensure the business remains bootstrapped and profitable.
IV. The outcomes: Streamlining Ops & Results
By streamlining operations through this agentic stack and getting more refined in the approach, I saved easily $250k+ in traditional CAC and OpEx while increasing velocity to reach launch week in under 90 days. The product is a scalable, lore-driven brand with a community-first loyalty protocol that gives back in multiple ways.
A key part of agentic strategy is connecting APIs amongst services.
As for the results, stay tuned for Part 2.
Building the Future: I am currently seeking my next high-impact role as a Full-Time Employee and/or Growth Consultant. If you want to move your organization from “using AI” to “running an Agentic Workforce” with 0-to-1 velocity, let’s connect.
Join the Cycle
1. Equip Yourself: Become part of the Founding 100, explore the First Cycle of gear and lore at Apres Leisure, enter the LeisureVerse and act on the Signal for gear at The Shop.
2. Read the Playbook: To understand the methodology behind the Forge, grab your copy of Finding Your True North on Amazon and make sure to leave a review if you find it helpful. It is the guide for any leader looking to find their signal in the noise of this complex generative age.
Michigan basketball just changed the game, rewrote history and won the school’s first title in 37 years. It’s a story of pain and resilience applicable for me and us all.
Yaxel Lendeborg, who didn’t have the grades for college back when, celebrates Shocking the World after the Finals win.
The Michigan Wolverines just wrapped up one of, if not the most dominant college basketball seasons in history, cutting the nets down in Indianapolis after beating the UConn Huskies in the Final 4, 69-63.
Despite a historically dominant regular season, Michigan lost it’s third game of the year, to a motivated Purdue game in the Big Ten Tournament Finals. Duke and Arizona became the hot, popular picks as champions.
Michigan took that loss to heart and went on a mission as the only team to score 90+ for 5 straight in the NCAA Tournament.
However, the UConn Huskies were hungry for a third title in four years. UConn hadn’t lost a final. That kind of experience is invaluable in crunch time, which was evident by all the close games they won in the tourney.
UConn had it’s way slowing down Michigan and muddying up the Final. No team had ever scored under 70, shot under 40%, shot under 15% on 15+ threes, gotten outrebounded and won.
0-50. Until Michigan did it last night, bringing it home despite the star player’s injury. Statistically, this Michigan team finished the season as the #2 team ALL-TIME in KenPom’s offensive and defensive efficiency ratings with an argument for most dominant – period(.)
______________________________
Personally reflecting: as a kid growing up, I loved playing basketball. I put in the work shoveling the driveway at night by myself in the cold dark winters of Michigan to get shots in. I went against the grain to the enemy Duke’s basketball camp twice around the 2001 championship, when Carlos Booker got stacked ((by the way, if you missed it: his sons were the tourney darlings going in to March Madness, featured on a commercial every break, leaving the tourney as the only #1 seed up 15 points at halftime out of 135 to blow the lead and lose. Cayden (the “other” twin) inexplicably turned the ball over before the 10 seconds ran out, as UConn’s Braylon Mullins hit a 35 footer in a finish no one will forget to advance to the Final 4)).
It’s crazy to think that at Michigan while I was there, we had former Duke star Tommy Amaker coaching a team with a bunch of notable talent that we’d see nearby walking around on campus. The team played well 3 of those 4 years but there were still ongoing sanctions in place for much of that stretch from the Ed Martin era sanctions tied to illegal gambling money and gifts going to players as loans, etc., which tainted 13 years of history, most famously the Fab Five team that lost to UNC in the Final because of the end-of-game timeout Chris Webber called that the team didn’t have.
I didn’t make it to Crisler for one game in college. Volleyball, hockey, baseball, women’s field hockey, softball, men’s and women’s soccer and each football game but not 1 for men’s basketball. The pulse was that low…
Then John Beilein arrived and restored hope, grit and spirit to the program. Everybody started showing back up.
I was there with my old roommates, classmates friends (and then some) in Atlanta at the 2013 Final 4, our first trip back since back when. A controversial Trey Burke block was called a foul and Louisville finished us off (although had to vacate the Championship for Pitino-era scandals of its own).
Celebrating a 2013 Final 4 semifinal win at the Georgia Dome in Atlanta over Syracuse.
We made it back to the ‘ship in 2018, but Villanova, who had the experience of winning it two years previous, took us down 79-62 to cut the nets.
Fab Fiver Juwan Howard took over coaching after Beilein went to try his hand at the Cleveland Cavaliers of the NBA, which didn’t last. Howard started hot and advanced to an Elite 8 in 2021, but he lost his cool on court and his teams faded to the lifeless 8-24 last place finish in 2024 and was shown the door.
Name Image and Likeness (NIL) became legal, players could now get paid and Howard cited not being able to keep up with the resources Michigan offered.
Star frontcourt player Tarris Reed transferred to UConn. Glue-guys Will Tschetter and Nimari Burnett stuck around, along with Jace Howard (Juwan’s son).
In came Dusty May, a former Indiana student manager under Bobby Knight, who made his way up the assistant ranks before getting a shot to lead at Florida Atlantic, leading the 9 seeded underdogs to an unheard of Final 4 and near championship appearance.
Michigan committed to upping resources available and with Champion’s Circle help behind the scenes (Michigan’s official Collective group, a small scrappy group of hard working folks I’ve gotten to know), May and staff mobilized quickly.
Michigan quickly fielded one of the quickest turnaround stories in history. But “we are all a bunch of outcasts” he said after finally smiling and cutting the net down back in Indy near where it started, bringing home Michigan’s first hoops championship since 1989. It’s true. Pretty much every guy had been counted out at some point, suffering anguish, lack of confidence and defeat.
May studied what the OKC Thunder did to go from doormat to dominant champ, stockpiling the right young guys. He met each player where they were at personality-wise and just asked them to be coachable and gritty. The team gelled, adjusted unlike any others at the half, went wild when walk-ons got stats at the end of historic blowouts. They just re-wrote the book on success in the NIL era, where fragmentation, the open transfer portal and dollars make continuity a challenge for everyone.
The “Fab 5” sat together on TNT’s altcast near courtside during the vaunted semifinal matchup against a dominant Arizona team that it dominated. They laughed, joked and carried on like it was 1993 all over again when they were going against the grain and changing the game, despite all the haters and doubters. 5 star combo guard Brandon McCoy committed to the Wolverines at halftime while talking the Fab 5 notably – what a moment.
Glen Rice held the “Shock the World” sign up when Michigan team last won in Seattle. Last night, 37 years worth of redemption songs came to fruition. But it’s not just the Fab 5 and ’26 champs that got redemption from the Martin scandals, it was everyone. All the players, the students, the parents, the fans – way too many to list.
Beyond that, it’s a story of hope when it feels like there isn’t much.
No one believes in you.
Your passive aggressive team thinks they can soullessly send you packing despite your loyal contributions. You got that email that you’re out, most recent casualty to a coding agent. Your elected officials have left you hanging, prioritizing themselves. Your family, partner or your health fails you. Whatever the (fill in the blank) reasons may be, it all feels hopeless. Why keep trying when the well is dry and it’s futile??
They don’t see or care that you’ve done the work, made the sacrifices and kept getting off the ground, pulling yourself up and back in motion.
“Those who stay will be champions.”
This is a story for you.
You can beat all the odds, reinvent yourself and become a champ in your own right too.
Go “Shock the World.”
Celebrating the redemption story and 2026 Championship win with SLC Spirit Group friends and members.
Times are tough. Cue your Alter Ego to help you battle through life’s challenges!
Sometimes it just feels like life is headed to hell in handbasket.
I recently published my first book to help others like me chart a course to purpose, if they could use guidance redirecting without instilling radical change (check it out if you haven’t yet!).
Finding Your True North: A Calm Path to Purpose Without Burning Your Life Down. Designed to help people find purpose with built-in exercises.
It’s okay to not be okay. Recently, for me it’s all felt like it’s coming to a head. Personally and holistically it’s been one thing after the next. Externally, it feels like the rails are off and the train is speeding down the tracks to inevitable peril…
“Jolts” involving A.I. disruption, job losses, the Iran war, consumer goods prices, health, policies, debts, extreme weather, etc. are a few hot buttons that feel like they are forcing radical change. I would venture to guess that I am not alone feeling this way.
It’s almost like we haven’t had a “normal” year without daily shocks since 2019 pre-pandemic.
People need to develop coping mechanisms to help them get through life’s challenges. I’ve personally found helpful include: meditation / deep breathing, relaxing in the sauna or hot tub, experiencing nature, exploring somewhere new, exercise, blocking out the news and social media, focusing on projects and hobbies, therapy, journaling, gardening, talking with people (especially spending time in person), playing with kids and pets, escapism via sports, music, podcasts, shows or movies.
Immersion into reading is another favorite ticket away. I picked up The Alter Ego Effect and wanted to recommend it to you.
The author Todd Herman, trained by top mental health coaches and mentors, helps his clientele channel their most resonating character to transform into when duty calls. By going to a totem or artifact to flip on the switch, cueing your alter ego, you can take on the world and come out of it heroically.
Simple example, Sam grew up feeling underestimated on his smarts often breezed over in conversations, work, etc. He’s noticed in movies that those with glasses are often thought of us wise and respected for focus and intelligence. Even though his vision is perfect, Sam throws on his totem/artifact fake lenses to cue the “Professor,” and his mentality and then results change. He’s getting the respect and attention that he’s always yearned for and he feels like he has a new lease on life.
Whatever that symbolism equates to for you, it has to mean something special, motivating and compelling. Think superheroes, a specific animal or truly anything that innately sticks out as transformative difference-maker in your mind. You can keep it a secret too – don’t feel like you need to let others in on your alter ego.
There is a lot we cannot control in life. Normally we would choose to go into character for those traditional “moments of impact” – the big meeting, game, speech or challenge.
If those normal coping activities aren’t getting it done for you when anxious feelings pop up outside of your typical “moments of impact,” maybe it’s time to beam the Bat Signal!?
Mark Cuban and Chris Klomp sparring on drug transparency issues
I didn’t leave last week’s Silicon Slopes with a tidy list of takeaways. I left with tension. And that mattered more.
Because when you’re building anything meaningful — a company, a career, a body of work — creation has a real cost. If there’s no friction, nothing new emerges. That idea threaded through nearly every conversation, keynote, and side hallway exchange I had over the week.
This wasn’t a conference about hype. It was about reckoning.
Tension Is the Point
One of the most grounding moments came during a deep‑breathing and reflection session led by Eric Espinosa of DeepLife. The prompt was simple and uncomfortable: What have you been carrying that’s holding you back — and are you ready to let it go?
I gave myself 48 hours after the conference to sit with that question. No productivity theater. No pretending I could out‑optimize it.
Just honesty.
Super hard in practice but that set the tone for everything else.
The Resume Is Dead. Values Aren’t.
We talked a lot about resumes — not as documents, but as signals.
Not titles. Not credentials.
Values. Behavior. Decision patterns.
The people who stood out weren’t optimizing for the next role. They were acting like the CEO of their own career — clear on what they stand for, how they work, and what kind of problems they’re willing to own. Author and LinkedIn editor Lorraine Lee spoke to this movement.
That framing is transformative. Especially now.
AI Isn’t Taking Jobs — It’s Exposing Them
There was no sugarcoating the AI conversation.
We’re in a 3–10× acceleration cycle for software change. Horizontally, there’s almost no defensibility anymore. Vertically — chips, semiconductors, infrastructure — everything is being reconstituted. The stock market collectively plummeted this week as a result of AI investments among FAANG companies and software was put on notice – if AI isn’t driving it forward.
A few things landed hard:
Salesforce was one of many stocks to slide this week but Salesforce Ventures’ Rob Keith detailed that its Agentforce augmentation service is already producing over $1 trillion and there’s more happened behind the scenes on the AI front.
Founders are becoming more technical again — not because they want to, but because learning velocity is the product.
Individual contributors who can think, build, and iterate are outpacing managers of process.
Product management as a standalone role is shrinking.
Customer success is becoming AI‑native.
CRM key functions are quickly being reinvented
Workforces will be half human, half agents — sooner than most companies are ready for. Right now you can build an agent-workforce to fill roles across the typical role spectrum for a cost fraction.
Humanoid robots in 5 years will be 95% there physically emulating movements.
“This year feels like the GPT‑3 moment — but for everything” (Ethan Choi, Khosla Ventures).
Here’s the quiet truth that kept resurfacing: the more technical the world becomes, the more human the winners are.
Teaching your team how to talk about their work matters.
Storytelling isn’t fluff — it’s trust‑building.
Transparency plus aligned self‑interest is credibility.
Sales isn’t manipulation. It’s clarity.
You don’t get to opt out of selling — your ideas, your vision, or yourself.
And authenticity isn’t aesthetic. It’s operational.
Doing Well by Doing Good Isn’t Optional Anymore
Some of the most powerful conversations centered on healthcare, transparency, and human suffering. Mark Cuban of Costplusdrugs.com battled Chris Klomp, Director of Medicare on this principle and stage.
65% of people live with a chronic condition.
Healthcare remains the #1 cause of bankruptcy.
Pricing opacity is morally offensive and brought on by big insurance.
And yet — we now have the tools to fix parts of this system in days, not decades.
Not because it’s profitable.
Because it’s necessary.
Help human suffering. Help one another. Do well by doing good.
That wasn’t a slogan. It was a challenge.
So Where I Landed
Silicon Slopes didn’t make me more certain.
It made me more clear.
Clear that:
Speed matters, but direction matters more.
Specialists will struggle. Integrators will thrive.
Learning velocity beats pedigree.
Building things — and selling them — is still the path.
The future belongs to people who can learn, connect, and serve. There were so many great vendors and individuals represented who were trying to live that Silicon Slopes motto. Highlighting one in Keep the Adventure Alive for those battling arthritis.
And clear that the work ahead isn’t about chasing trends.
It’s about choosing problems worth solving — and having the courage to stay with the tension long enough for something real to emerge.
If any of this resonates — if you’re building, re‑building, or re‑thinking where you’re headed — I’m always open to thoughtful conversations. Not pitches. Not noise.
Our Southeast Asian travels continued, this time to Singapore then the Philippines. We got to experience manmade and natural wonders and cuisine, learning a lot about the cultures in the process.
Calabawan Falls
After the safari of a lifetime visiting Borneo’s unique species’, we shipped off from Sandakan to Singapore via Malaysia Air, connecting first in Kuala Lumpur (the only connection while in Southeast Asia for us). We quickly spent the last of our Ringgits on a bottle of wine and some duty-free candy and in just over an hour in the air, we were in the fascinating island city-state of Singapore.
Changi Airport is the top-rated airport in the world. It’s expansive, has so many designer stores, gardens, aquariums and fountains (including Jewel Changi with a waterfall) and entertainment. Asian airports have shown how efficient travel can be, not to mention the amenities.
Knowing Singapore is one of the most expensive places in the world, we went budget on accommodations. We ended up at Hotel Fuji in Geylang, once a thriving red-light district (Singapore’s stance on sex workers, like its stance on most in the non-super-wealthy demographic, is SUPER exploitative to say the least). We got a cuisine recommendation from our Uber driver, who speaks excellent English like most in Singapore. It was a seafood market lit up like a mini Vegas and the menu featured all kinds of interesting novelties. Frog leg porridge was a suggested favorite here. Crab is a top specialty of the Singapore dining scene, which has many curated, immersive, multi-course elaborate experiences. I ended up trying the grilled frogs legs and crispy short-ribs (I enjoyed the latter more, but fried makes everything taste better). The area was walkable but every we went into a bar, many of which had karaoke vibes, as the underground gambling dens and beauty shop discreet sex workers were pretty strictly getting squashed out (and it felt like they were still . Lots of funny looks and not so welcoming vibes.
Singapore is one of the most meticulously clean, landscaped and managed places you’ll find in the world. It is also known for the strictest laws to keep the place clean in all the ways it perceives it can. We had a mad scramble to finish our gum before arriving and learned a lot about the hundreds of laws from the local drivers (many of which are doing it was a second job because it’s so expensive to live there, the locals have subsidized shoebox houses and shop in nearby Malaysia). Not only is chewing and spitting out gum a crime that can lead to caning, but so jaywalking, staying out drinking past 10pm with 3+ people, being naked in your house, and so many more things. Most laws are designed to keep the locals in line without wavering, catering to the rich finance moguls, visitors and expats. Cameras are everywhere, and you can get arrested typically 4-6 hours after a violation and sent to prison. It felt very dystopian (remember reading The Giver?).
We set out to experience Singapore’s top sites, including Chinatown, Gardens by the Sea and Singapore Botanic Gardens. We saw another ornate temple requiring shoes off and conservative dress to enter. Just outside on the market street in Chinatown, we tried the famous Singapore Sling cocktail (all the Brits will point you to Raffles Hotel for the very expensive original). We meandered, watched some chess with an audience and looked through the vendor goodies. The Botanic Gardens was this magnificently catered park curated with so many different species and garden zones with science labs cloning species in the middle of it all. We met a few pretty birds and nice big monitors and skink lizards while enjoying the beautiful curated surroundings.
The Gardens by the Bay was a paid attraction with electric towers lined with plants, and we paid to take in two top attractions: Cloud Forest and Flower Dome. Flower Dome was an indoor garden with plant species from all over the world organized in different zones made to feel like you were globe-trotting.
Cloud Forest was another indoor garden and jungle Jurassic Park animatronic immersive experience. These domed areas with clear glass provided views of the harbor and a lot of lessons about the various featured species. We especially enjoyed this experience, loving dinosaurs, the movies and nature like we do.
We capped it off in the largest skewered meat market imaginable and trying to catch a light show on the harbor (later realizing it was only at the ship in the sky-looking Marina Bay Sands Singapore hotel). They tried to charge $90 for 2 cocktails at this rooftop bar, luckily I talked them down a bit on that!
36 hours after arriving, we were happy to be taking off on Singapore Air (another amazing regional airline) for our last big leg. Just about four hours later we made it to Cebu in the Philippines. The Philippines are home to 7,641 islands, and only about 2,000 of which are inhabited. This reefy, volcanic splash of paradise hit me when flying in as I watched the islands stack up.
My grandfather fought in the 503rd/101st Airborne Infantry, the only regiment in the Pacific for World War II. My cousin’s husband (also on my dad’s side) Stephen Greene was a helicopter pilot in Vietnam in the same regiment and recently shared his newsletters about the stories.
“Grandpa” shared very little to my dad or us about those days, although famously would not eat monkey again and hated rice. We were told he was shot in the butt and that he won a Purple Heart and Silver Star and later learned he had some notable machismo adventures while based in Australia (ie. nighttime non-sanctioned jumps, fights with the Marines). I read about the battles he fighted in Leyte, nextdoor to Cebu, Mindano and Corregidor. Corregidor sits in Manilla Bay (near the Japanese taken Manila base), is known as “the Rock” and hosted one of the most infamous battles in American war history based on being the most difficult technical landing of a parachute troop drop historically, the casualty rates and multi-day siege that took place.
Connecting with my grandfather’s story resonated as we dropped into Cebu City the main city in the Central Visayas (3.4 million inhabitants span the 167 islands included in this central Philippine zone known for the greatest biodiversity, hence our visit). We were warned about civil wars ongoing in Mindanao and heard that Manila is very dirty and overpopulated, so they were avoided.
We stayed in Lapu-Lapu City nearby at the Blue Maribago Beach Resort, 15 minutes from the airport where a local opportunistic man picked us up in place of a Grab, ended up paying him in cash (a bit more than the going rate to help with his family mentioned as he was very nice, opportunistic and accommodating).
It didn’t take long before the Philippine spirit shined through via most of the people we met. Our room was upgraded to beachside by the staff, all of which would smile, put hand on heart and say good morning, afternoon or evening when walking by. The villa overlooked the sandbar island and lagoon beach in front of us. The room was spectacular and spacious, we were a within a short walk from hammocks, this amazing exotic seafood buffet and restaurant, another with a bar on the water, and beach-themed lagoon pools. There was live music, a thrilling fire-dancing show and beach service to the canopies. Food specialties were noodles or rice as a base, steamed veggies, all types of seafood, served all kinds of different ways, fried chicken and crispy pork dishes, along with different tropical fruits and veggies.
Our 3am departure and full-day tour was both of our top highlight of the entire trip. A driver brought us hours away to the southwest coast of the island to Oslob. We geared up and got herded out to the water, where the locals were attracting whale sharks with treats, the largest species of shark (harmless spotted filter-feeders). Soon, we were in the water getting brushed by these massive gentle giants (the rules were no sunscreen as it negatively affects them and don’t touch). While many were juveniles, the sheer beauty and magnificence of these ~25 foot wonders was incredible first-hand underwater, and I was lucky to capture our moments together on my GoPro.
Calabawan Falls awaited us, a jungle paradise and hike into a series of waterfalls. Rain closed another epic set of falls for flooding, and made the hike slippery – luckily we had the most attentive, happy, strong, agile barefooted young 5 foot tall local guide and photographer. The cliff diving and abseiling down waterfalls was incredible, as was the sheer beauty of the dense jungle surroundings. We capped it off with a fresh, hot meal on the coast, seeing the ruins from the latest cyclone two years removed.
We had a self-care day to make the missus happy, featuring facials, mani-pedis and a new hair-styling – all at less than the cost of one premium service here. We got to wander around locally, amidst the locals and their markets out of their houses, little stores, rickshaws, basketball courts and motobikes and scooters (2nd world feel to the place). The locals talked of the government corruption, which left road construction projects constant, slow and under-resourced. Our last night brought a wicked tropical thunderstorm, which was quite an experience.
I grabbed a Philippino-pained long ukulele to think back to my days looking at the sky-blue water and green island foliage of the islands. Sadly, soon after we got back, Cebu got hit by a 6.9 earthquake and cyclones, killing over 70 with massive impact on the locals. This volcanic hotbed can’t rest from tectonic movements.
Overall, this was the most inexpensive place we visited (felt it to be ~20% what we’re used to paying financially). The people were also the most happy, genuine, friendly, service-oriented wonderful folks. We would highly encourage others to visit, support the people and see what it’s all about. We will be back and our minds stay relaxed picturing the Filipino landscapes and mindset when in a peaceful state.
After a Taipei night for stop-over, we were riding the jet stream winds on a 10 (down from 14) hour flight back stateside to Seattle, asked a few Customs questions about my guitar (not a gun) and were officially back stateside. Back to the wild ride of emotions, big box stores and Americana, and still thinking about prospects of living and traveling around these wonders of Southeast Asia.
This blog reflects on the wonders of Malaysia, sleeping giant, Muslim mecca with thick jungles, temples and 20% of the world’s species. It details our adventures exploring these wonders and getting to know the creatures.
After about 52 hours in Taiwan, we caught a midnight five hour Air Asia flight across the South China Sea to Kuala Lumpur, Malaysia. Like Taiwan, Malaysia is an energy, resource-rich hotbed for wildlife that is affordable and another expat favorite for so many reasons.
AirAsia is on the economy side, but it was comfortable enough and who’s site and app were notably easy to use, even with flight changes. Uber isn’t currently in Malaysia, but there’s a few others that are similar, Grab being one I latched onto for rides for this trip. I learned the hard way from a driver that you have to match baggages with ride option and once I upgraded, it was a long hour+ drive to the central commercial zone of KL.
We got to our “hotel” and were greeting by armed guards in stand out front that gruffly let us through when we showed authorization of staying at The Manor KLCC. We went up a floor to a small hotel check-in place, realizing this place was more like executive residences than a true hotel. We paid a fee to check-in early and luckily could collapse in our unit, which felt like a luxury 1B condo overlooking the expansively growing skyline of KL, including Merkeda Tower (2nd tallest building in the world) and Petronas Towers (largest dual-connected towers in the world).
After a few hours of sleep, I set out to get a few essentials including an outlet converter as Malaysia has a different plug than ours unlike Taiwan. Malaysia is a highly Muslim country, which is evident by all the birkas on the flight, middle-eastern / conservatives appearances walking around, and the dichotomy of old world and all this new, modern construction and high fashion was fascinating.
Downtown KL has a ton of shopping and malls and the nearest grocery store was about a 25 minute hike away, past other executive residences. I hit a food court in the mall and was lost trying to figure out breakfast options, went with what looked like the most similar and found myself trying to figure out what I got handed a hot water heater for boiling eggs with my toast and sandwich. I was able to finally figure out how to get a few staples, electric plug converter included to save the day. We learned that Malaysian food is like an Indian / Thai / Middle-Eastern collaboration, often quite spicy and there are markets dispersed for it around town. We tiptoed around it with some Thai and shwarma-like middle-eastern options.
The WOW moment downtown came at our rooftop pool – a stunning, relaxing experience to take in the sights all around.
After a day of adjusting, where we ordered in, our tour adventures continued starting with a visit to the legendary Batu Caves. We met our first Asian monkeys, who were very socialized and used to the many tourists, often opportunistically stealing bags for food jackpots and waters. We walked past the golden Lord Murugan Statue and up the stairs, where Alli was shift-grabbed by a monkey while trying to take a selfie. At the bottom and into the caves were these picturesque, colorful holy temples. Breathtaking to take it in and we had to grab a few souvenir gifts.
We stopped at a hand-painted shirt factory en route up north an hour and a half into the dense jungle for an epic elephant sanctuary visit. When offered the chance to bathe and feed young elephants as part of a private tour, we took it and didn’t regret getting soaked for the experience. Gandah, the only sanctuary-born elephant of the 40 in residence was a sweetheart. All of the gentle giants were there for injury or infringement on town areas and relocated for protection. We got to pet, feed and get to know about 8 elephants, who were eager for treats.
Off we left to fly out from there from the western peninsula to the island of Borneo, home to Brunei, Indonesia and Malaysian territory. At the KL airport, we had to pay to upgrade bag coverage past the tiny allowance. The domestic flight terminal was tight and cramped and I felt bad for the quiet, unassuming line of 15 short Muslim girls who got jumped by many others to get through the gate. Between there and the pool, where they could dip feet in only, the gender disparity gap seemed pretty wide and unfair, but not my place to judge.
We arrived in Sandakan in the state of Sabah on the northeast corner of Malaysian Borneo, caught some quick winks and were picked up for our all-included tour to experience the heart of where 20% of the world’s species reside. First stop nearby was the Orangutan Conservation & Rehabilitation Center. Orangutans are down in numbers to just over 100k and live on two islands, here and Sumatra. In this swampy, sticky jungle, organutans are fed and the sick cared for. They are free to go and the food is not what they’d consider top shelf, and they often have to fight off the local macaque clans to get it, which was fascinating to watch, along with the mom with baby and other cute, flexible, swinging relatives.
Nextdoor was a Sun Bear Conservatory, another fascinating animal nearing endangerment, who are secretive without much known about them. These guys are the smallest and most vulnerable of the bear species. We saw these little around 8 of these brown-faced critters munching on vegetation shared happily, including sitting up knawing on carrots. We saw a resource fight between two, which featured high-pitched squeals and screams and some chasing that felt more akin to badgers than bears.
From there, we drove to Sim Sim Jetty, a Chinese coastal neighborhood in the community, which featured some large Amazon pet fish and all kinds of beautiful potted plants lining this dock. Off we went staring at the mountains that fed into this coastal community with a scenic mountain island and speedboat ride sending us ripping our way an hour and a half into rivers with thick mangroves and trees lining the shore. En route, we spotted a large ~13 foot saltwater croc sunning on shore (the first I have seen!).
Our first river lodge (Kinabitu ?) had a lot of character, cozy cabins with AC and a fan, which helped in the sticky humidity. I appreciated getting to walk the labeled boardwalks trying to spot creatures, including at night with a headlamp, seeing tree frogs, spiders a lantern bug and more. At dawn and near dusk, we set out on our skiff to seek out wildlife near the shore at peak times to catch there. Our guide Lat knew so much about the species and both he and the driver were able to spot animals while moving fast, while also coordinating with other tour guides. The government protects the area with the help of tourist taxes, and it shows as the animals show little worry about nearby gawkers.
We quickly spotted Borneo-specific harems of Proboscis Monkeys, featuring an alpha and the mates and offspring. The pot-belied males feature the giant, long floppy noses and despite their figure, can launch themselves from tree to tree. The females have smaller, pointy noses. Reading Ancestor’s Tale, it details the divergence of humans down the line of primates and the Probiscus are a nearer relative not far off from the split from orangutans ~13 million years ago. Easy to see the resemblance, really started at you and sat there picking and eating leaves and you could confuse with people without too much imagination. We enjoyed watching babies doing acrobatics and bachelor groups as well.
Easy to enjoy the beauty of the river and sunsets, river inlets and quiet lakes off the main river and at dusk, the fireflies lighting up around a few trees and calls of the wild all around.
The lodge offered great fresh-cooked delicious meals featuring steamed veggies, rice, noodles, fish, shrimp, fried wontons, and delicious local fruits and tasty deserts. There was a special night that we all wore the native Sarongs and enjoyed a meal with local women old and young playing soothing music with their instruments.
At this point, we were seeing a number of sub-species of Horned Bills, one of the few species that picks and stays with a partner for life. We saw a pair of grey langurs, one grooming the other. In a palm tree at the second lodge, a staffer pointed to a flying lemur that was probably nearly 4 feet long, waiting for the chance to soar when night fell. We were seeing so many macaques that they were becoming pedestrian. At the second lodge, they gave us sticks to beat them off as they are known to go after bags for food. Alli stayed in the pool when everyone else went to lunch and the pack jumped right in, partying like it was spring break – hilarious!
On the reptile front, there was an emerald green pit viper sitting in the same spot daily near the kitchen with a lump of a catch from recently, fascinating to see it sitting in the bush like a stick a few feet away. We saw numerous skinks and geckos and were lucky enough to watch another nearly 10 foot croc from close before he spooked, snapped and leapt in the water.
What really made this incredible experience all the more special was that on the way back, the 1st lodge reported an orgunutan visiting, and we were able to zip back and watch him in the canopy near our breakfast spot the previous day. Part of the group instead followed a pygmy elephant, who came to the riverbank. As we waived at the staff sending us off and zipped past the floating bottles with fish flying off the wake, looking at the islands of the coast, we just smiled having experienced a truly incredible part of the world. I hope gets the protection it needs to stay that way.
Taiwan is not what you may think. This place is an incredible infusion of old ways and progressive living, lined with national parks, vibrant night markets and more.
Delta’s flights, which we connected in Seattle with a manageable layover with 3 separate Skyclub visits en route. I was lucky enough to be sitting behind a Michigan grad from Ann Arbor flying to China with his folks and we split the $40 internet fee to watch UM / OU (even though they announced that internet wasn’t available for the flight, this feed came through with regular manual refreshes).
Once we finally figured out our Arrival Cards and how to get out of the airport, we were eager to get to our hotel, the Miramar Gardens Taipei for some rest and adjustment to the 13 hour time difference. Luckily, Uber served Taiwan and we had about an hour ride to get to the Zhongshang District in the heart of the city. We found this to be a very nice, comfortable, convenient choice and cool neighborhood to explore. Highlight was the “Japanese Style” spa (read: had to sign-off on being naked to utilize the hot and cold tubs, steam & sauna rooms, etc. It was a very relaxing and soothing experience. The outdoor pool area with lounges was also very relaxing and appreciated, as was the bidet with all kinds of settings (we got quite used to having these regularly).
Taiwan is known for having a leading amount of convenience stores and the trip to my nearby 7-11 turned out interestingly. We brought a lot of snacks but I wanted to supplement a few meal with finds from there and what I got was not what I expected upon picking. Instead of cheese, I got an egg product another weird protein product that was like tofu, beef gizzards, sparkling wine in a can with bobas (they also invented Boba/Bubble Tea), crab flavored corn nut like and other chip-like things.
Another local staple is beef noodles and I tried it nearby and enjoyed the pho-like dish (although wasn’t willing to wait outside this famous noodle house and found another I could get served quickly). The Liaoning Street Market was a short walk away and fun to walk the streets seeing what the locals were dishing out and feeding folks. Visiting the night markets is a must in Taipei as they’re buzzing with energy and interesting vendor finds. We also checked out Raoshe, which was much bigger and more action-packed. Nextdoor was a fabulous 300 year old temple with a ton of intricate special details in the design.
We opted for a few photos out front and not the ride up what was the world’s tallest building in Taipei 101. Notably, Taipei despite being a top population dense city also felt green and sustainable with lots of parks.
The biggest highlights came via our private Viator custom tour, of which we had the best, most engaging guide in “Nicolas” (after Cage, who along with other Hollywood movie stars taught him his great English)., who left a career in business for the flexibility and change of pace in providing special tours. Despite his Lakers hat (sensitive subject with me historically), Nicolas connected well with both of us – he loved his baseball (following Taiwanese stars especially), the NBA and playing badminton regularly.
He taught us a lot about the culture while taking us to the Houtong “Cat Village”, an old coal mining town turned tourist attraction with community cats and related local ties. He also took us to Yangmingshan National Park, a mountainous volcanic forest with geysers and hot springs that fed right down into the north side of Taipei. One hot spring pool had a small temple to honor the ghosts of residents with no families. Volcano Island appeared off the rocky north shores of the island. We saw a big Formosan Rock (or Taiwanese) Macaque on a fence near the road, several skinks and an egret. For $34, we had an upscale 90 minute private spa soak room with a hot and cold tub piping mineral water.
Taiwan has a number of other national parks including Turtle Island, named after it’s appearance of a partially submerged turtle. It’s temperate semi-tropical climate make it a very comfortable place and its easy to see how why it’s a surging place for expats.
Lions are a key symbol for Taiwan, known for warding off spirits, being brave and courageous and lucky. We had good luck exploring this special place and think you would too.
