What if AI made you more present, not more addicted?

Dennis Crowley (founder of Foursquare) shares field-tested lessons from 20+ years building in NYC, why he prefers NYC to SF, and the thesis behind Hopscotch Labs and Beebot: ambient, context-aware experiences designed to push you into the real world instead of into a feed. We also get tactical: notebooks, hiring, early-stage chaos, and how to stay in the game when you feel burned out.

(00:00) Intro — A founder’s field notes from NYC

(03:05) Why writing things down changes your brain

(09:10) “You fall to the level of your systems”

(14:45) From Dodgeball → Foursquare → Hopscotch Labs

(19:35) BeeBot — proactive, wearable AI and why it’s hard

(27:15) Hiring for uncertainty: side projects, skill, and resilience

(34:30) NYC tech evolution — capital, talent, and density

(41:10) How to battle burnout

Follow Dennis Crowley on LinkedIn: https://www.linkedin.com/in/dpstyles/

Follow Dennis Crowley on Substack: https://teendrama.substack.com/

Hopscotch Labs: https://hopscotchlabs.co/

BeeBot: https://dens.medium.com/say-hello-to-dj-beebot-592cdc1f1704

Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing

Join the Executives Unplugged Inner Circle for free coaching via email: https://execs.tv

Subscribe to the show:

YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM

Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN

Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

Over half of startup executive hires fail in the first 18 months and many in the first 30 days.

Executive hiring is a high-stakes gamble. One bad fit doesn't just cost money; it can derail your entire momentum and kill team morale. Yet, most companies are still playing a game of mutual selling that incentivizes flaunting and filtering over honesty and results.

Meghan Oliver decided to stop playing that game.

After stepping off the corporate hamster wheel to build her own business, she found a way to bypass the interview dance entirely. She joined a Series A healthcare company as a fractional product leader. No elongated interview process, just real problems to solve on day one.

What started as a 90-day experiment ended with Meghan rewriting the company’s product and operations playbook and stepping in as full-time COO.

In this episode, Meghan reveals her framework for how to wildly reduce the risk of a mis-hire and either close your next great executive or land your next great gig.

Chapter Markers:

00:00 — Why traditional executive hiring often fails

01:00 — Meghan’s path: burnout, sabbatical, and discovering fractional

03:20 — Starting fractional at RightMove Health as CPO

04:20 — Finding clarity in context, not just function

07:20 — What makes a fractional executive role actually work

10:50 — Evolving from fractional CPO to full-time COO

13:20 — Why combining product and ops cuts coordination tax

15:00 — The power of a 90-day “try before you buy”

15:40 — Navigating health insurance and benefits as fractional

18:40 — How the role shift felt seamless for the team

20:40 — Building conviction and quieting self-doubt

22:40 — Advice for CEOs and executives on fractional hires

26:20 — What’s happening at RightMove Health (and open roles)

Follow Meghan Oliver: https://www.linkedin.com/in/meghan-oliver/

Shoutouts

RightMove Health: https://rightmovehealth.com

Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing

Join the Executives Unplugged Inner Circle: https://execs.tv

Subscribe to the show

YouTube: https://www.youtube.com/@execsunplugged Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

Matt Blumberg reveals why he bans slides, forces independent directors to audition for a seat, and uses AI to simulate Steve Jobs in the boardroom.

For many founders, the board meeting is a dreaded time sink full of status updates and glazed eyes. In this episode Matt Blumberg, the CEO of Markup AI and author of Startup Boards, breaks down how to turn your board meetings into your ultimate strategy session. Matt shares the story of a "perfect" board candidate who failed a live audition, the "Rule of Ones" that will lead to an effective board composition, and why he strictly forbids slides during meetings.

He also reveals a new experiment: using AI agents to simulate a "Fantasy Board" meeting with personalities like Steve Jobs and Warren Buffett to stress-test decisions before the real directors show up.

Executives will come away with a playbook to stop reporting and start using their board to build the business.

00:00 — The No Slides Rule

02:04 — Turning the eye roll into strategy

03:20 — The Audition: Making directors do the work

06:58 — How to reference check your VCs

08:59 — The "Rule of Ones" for board composition

13:25 — Stop writing 50-page board decks

17:24 — Specific rules for better conversations

20:58 — Inside the Markup AI pivot

23:05 — The "Fantasy Board": Simulating Steve Jobs with AI

26:19 — How to fire a board member

28:17 — Why every CEO should sit on another board

Follow Matt on LinkedIn: https://www.linkedin.com/in/mattblumberg/

Shoutouts

Startup Boards: https://www.amazon.com/Startup-Boards-Building-Effective-Directors/dp/111985928X

Markup AI: https://markup.ai

Fred Wilson: https://avc.xyz

Mike Collins: https://www.linkedin.com/in/mike-collins-362100/

Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing

Join the Executives Unplugged inner circle: https://kc.coach

Subscribe to the show:

YouTube — https://www.youtube.com/@kcowing

Spotify — https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts — https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

Too many offsites miss the powerful opportunity to align a leadership team. Here’s how to make yours the exception.

In this episode, Kelly Dwyer, executive coach and facilitator, breaks down what separates transformational offsites from frustrating ones. She’s helped leadership teams at venture and PE-backed companies turn tense conversations into breakthroughs and knows exactly how to keep the “elephant in the room” from derailing trust.

Kelly and host Keith Cowing unpack a tactical playbook: how to prep the right way, design the space for honesty, navigate conflict, and make sure the alignment lasts.

Leaders will walk away knowing how to run an offsite that doesn’t just check a box, but changes how their team thinks, decides, and leads.

00:00 — Why offsites fail (and how to fix them)
02:10 — How prep work sets the tone
05:00 — The value of “having a sleep” between days
07:40 — The CEO’s role: set vision, not the agenda
10:50 — Creating meeting agreements that drive honesty
16:20 — The facilitator’s job: manage time and truth
18:50 — Handling conflict when the “fight” breaks out
22:30 — Tools for structure: parking lots, sticky notes, and timers
25:40 — Decision-making without consensus traps
28:20 — The “Fist to Five” tool for real alignment
30:20 — Ensuring follow-through and lasting impact
33:30 — Why offsites are the most powerful (and risky) meetings you’ll ever run

Follow Kelly Dwyer on LinkedIn: https://www.linkedin.com/in/kellydwyer/
Visit Kelly’s Website: https://kellydwyer.co
Listen to Kelly’s Podcast: https://www.lifefromwithin.com/

Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing
Subscribe to Keith’s free coaching via email: https://kc.coach/

Subscribe to the show:
YouTube: https://www.youtube.com/@kcowing
Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN
Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

A startup founder joins a 10,000-person company to build AI from scratch and learns how to move fast without losing trust.

Moving fast inside a big company can feel impossible. You’re hired to shake things up - but if you move too quickly, you lose people. This episode dives into that tension. Atlassian’s Head of AI, Nisha Iyer, shares what happens when a startup founder joins a 10,000-person company and tries to build new AI products from the inside. She unpacks learning to slow down, earning trust, and building momentum the right way - without giving up the spark that made you effective in the first place.

Executives and operators will relate to the tension between urgency and patience - and take away ideas for leading change without burning out your team or losing trust.

• 00:00 — Moving fast meets resistance
• 04:00 — “Learn the business”: slowing down to speed up
• 09:00 — The big swing that fell flat — and the lesson in humility
• 17:00 — Piloting change and earning trust one team at a time
• 22:00 — Turning internal wins into customer-facing AI
• 26:00 — Balancing empathy, momentum, and trust
• 31:00 — Reducing fear, sparking excitement: leading through change
• 36:00 — What’s next: voice tech, connection, and being more human

Shoutouts:
The First 90 Days — https://www.amazon.com/First-90-Days-Strategies-Expanded/dp/1422188612
Atlassian — https://www.atlassian.com
Rovo — https://www.atlassian.com/software/rovo

Follow Nisha Iyer: https://www.linkedin.com/in/nisha-ranjani-iyer/

Follow Keith Cowing: https://linkedin.com/in/keithcowing
Subscribe to Keith’s free coaching via email: https://kc.coach

Subscribe to the show:
YouTube — https://www.youtube.com/@kcowing
Spotify — https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN
Apple Podcasts — https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

If you want 5x growth, you need more than a great product. In this episode, Recoup co-founder Siwat Siengsanaoh breaks down how trade shows, advisory boards, and fast feedback loops turned ginger-forward beverages into a national Target launch. You’ll learn how to build an advisory bench, get massive distribution, expand margins, and use polarizing positioning to earn raving fans.

(00:00) Intro — From trade shows to Target shelves

(03:20) Lean teams, volunteers, and winning Pitch Slam

(06:48) Building an advisory board that moves margins

(13:16) Polarization as a brand strategy: the ginger edge

(16:33) Customer feedback and fast iteration

(25:45) Rethinking risk: small bets, tight feedback loops

Drink recoup: https://www.recoupwellness.com/

Follow Siwat Siengsanaoh on LinkedIn: https://www.linkedin.com/in/siwatsiengsanaoh/

Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing

Join the Executives Unplugged Community and get free office hours: https://kc.coach/executives-unplugged

Subscribe to the show:

YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM

Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN

Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

Feeling like your calendar is running your life? In this episode of Executives Unplugged, executive coach Keith Cowing shares a battle-tested playbook to flip the script. Learn how to audit your schedule, spot energy-drainers, and make small but powerful changes that double your strategic time without burning out.

You’ll discover:

How to run a calendar audit step by step

The “two truths and two pies” exercise

Simple psychological tricks to protect your focus

Why just a 10% shift can double your momentum

Subscribe for more playbooks to lead with clarity and momentum.

Chapters:
(00:00) Intro — Is your calendar running your life?
(00:51) The Tetris analogy: when meetings feel like blocks falling
(02:20) Step 1 — Calendar audit explained
(04:06) Step 2 — Analyzing results: the two pies and two truths
(07:53) Step 3 — Making changes and mindset shifts
(09:04) Protecting your focus like it’s a meeting with the CEO
(11:11) Setting boundaries and saying no with confidence
(12:48) Closing thoughts — audit, analyze, shift

Follow Keith Cowing:
Follow on LinkedIn: https://linkedin.com/in/keithcowing  
Join the Executives Unplugged community for free coaching via email: https://kc.coach

Subscribe to the show:
YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM
Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN
Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

Your org chart is obsolete. It's time to move from silos to studios. The old model of large, hyper-specialized teams is now a liability. If you're looking to leverage AI to innovate faster than the competition, this episode offers a playbook. 

Product leader Nate Gosselin introduces a new model inspired not by corporate frameworks, but by hip-hop producers. He breaks down the concept of the "Product Producer" and the shift from rigid, siloed teams to small, nimble "studios" powered by AI. This conversation provides a tactical guide for leaders to rethink their org design, tackle technical debt, and build the multidisciplinary teams needed for the future. 

In this episode, you’ll learn: 

(01:31) What is a "Product Producer"? 

(05:12) The Skills to Hire For: AI Literacy and Multidisciplinary Talent 

(11:09) Managing AI Like a Team of Highly Capable Interns 

(13:30) Where to Start: Low-Risk, High-Impact AI Projects 

(16:33) How to Use AI to Tackle Your Scariest Tech Debt 

(20:49) The New Org Model: Shifting from Assembly Lines to Creative Studios (31:53) Your First Step: A Practical Guide to Implementing AI in Your Workflows (39:08) The Personal Transformation for Leaders: From Specialist to Builder

Follow Keith Cowing: 

LinkedIn: https://linkedin.com/in/keithcowing 

Subscribe to free coaching via email: https://kc.coach

Subscribe to the show: 

YouTube: https://www.youtube.com/@kcowing 

Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN 

Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

Follow Nate Gosselin: 

LinkedIn: https://www.linkedin.com/in/nate-gosselin 

Website: https://www.heynate.me/

The pressure on leaders to deliver rapid, transformative change has never been higher. But how do you move fast without leaving your people behind?

In this episode, host Keith Cowing sits down with Perry Steinberg, a seasoned Chief Product Officer with deep experience leading through high-stakes transitions at both public companies and fast-paced private equity-backed firms. Perry unpacks his core leadership philosophy for navigating this exact challenge, revealing how to maintain cohesion and drive results simultaneously.

In this conversation, you will learn:

• The Art of Cadence and Commitment: The methods Perry uses to build trust and alignment, even when making difficult decisions.
• Leading the 'Mindset Shift': Discover techniques to guide an organization through a fundamental change in thinking and strategy.
• From Chaos to Cohesion: Hear how Perry unified disparate teams and roadmaps post-acquisition to create a single, focused vision.
• Staying Relevant in the AI Era: Understand why past playbooks are obsolete and what skills are critical for leadership in a world of constant technological disruption.

This episode is for any leader tasked with steering their organization through uncertainty.

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Access free, email-based coaching for executives. Join the conversation at https://kc.coach.

What do you do when a leader tells you, "You have integrity. That's rare in this profession"? For my guest Natasha Jaffe, it was the signal she needed to leave.

In this episode of Executives Unplugged, I talk with Natasha, an experienced engineering leader and coach who has guided teams at both Fortune 100 companies and startups through multi-billion dollar acquisitions.

We have a raw and honest conversation about the critical mistake leaders make when they chase productivity gains but accidentally "squash the magic" that makes their teams special. Natasha shares a powerful playbook for leading through disruptive changes—like reorgs or the push for AI—by protecting your team's "flow state" and listening to your own moral compass.

This episode is a masterclass in leading with empathy and principle, offering practical advice on how to navigate immense change without losing your team, or yourself, in the process.

Guest:

• Natasha Jaffe: Experienced Engineering Leader and Coach.
• Find Natasha's writing at her blog: Nuts and Bolts on Substack

In this episode, we discuss:

• (1:13) What is "Flow State"? Natasha explains why long, uninterrupted blocks of time are the source of an engineer's most creative and deep work.
• (2:11) How Leaders Destroy Flow: Forcing teams to prioritize the "important" over the "interesting" for too long erodes curiosity and squashes the magic.
• (3:40) The Human Reaction to AI: Why engineering teams often react to top-down AI mandates with trepidation, seeing it as "dystopian" and a threat to their craft.
• (4:35) Fear Kills Innovation: When your team is afraid, they won't engage in the productive risk-taking required to innovate.
• (5:11) A Case Study in Leading a Reorg: How Natasha turned a messy, demoralizing situation into a success by bringing the team into the decision-making process, listening to their fears, and even choosing a team mascot.
• (8:33) The Real Path to Moving Faster: Stop telling your engineers to "run harder." Instead, reduce toil and remove friction to "widen the mouth of the funnel."
• (9:16) The Collapsing Talent Stack: Are we moving away from hyper-specialists and back toward multi-skilled teams who can move with lightning speed?
• (12:49) The Bell Curve of Team Size: The trade-off between having more minds on a problem and the rapid degradation of velocity and quality when "too many cooks are in the kitchen."
• (15:01) Your Moral Compass: Why you can't leave your values at home and how the biggest career regrets come from not listening to your gut.
• (16:35) "They Said the Quiet Part Out Loud": The powerful story of how a single comment about integrity was the signal Natasha needed to make a pivotal career change.
• (18:41) Key Questions to Ask Yourself: How to get clarity when your job is in conflict with your values, and how to know when it's time to explore a change.
• (22:08) On Burnout and Recovery: Natasha shares her personal journey of recovering from massive burnout and rediscovering creativity.