Executives Unplugged

Teams don't swirl because they disagree, they swirl because nobody is empowered to end the debate and move.

Mahesh Guruswamy runs product, engineering, and customer support at Kajabi as a single-threaded leader, a model he picked up at Amazon and carried through Smartsheet and Kickstarter. His case is simple: when two peers share a decision and neither one can break the tie, the whole org waits for them to agree. We get into how he keeps genuine challenge in the room without giving anyone veto power, why he runs a business review every Wednesday, and exactly which decisions he keeps versus delegates. We also cover what it takes to get from your current model to an AI-native model when the change touches people's jobs and nobody volunteers to give up their turf.

CHAPTERS

00:00 Intro

01:03 The case for a single-threaded leader

05:12 Healthy tension without veto power

06:53 The Wednesday business review

09:17 Turning meetings into context for AI

10:37 Recording everything by default

12:30 Change management when it touches people's jobs

14:18 How to tell if your exec team is too slow

16:27 Business leaders, not functional leaders

19:01 Anger, fear, and the decisions they cause

19:49 Underwriting risk instead of pushing it down

22:22 One-way doors and two-way doors

23:37 The readme that names who decides what

24:44 Calm but oddly ambitious

27:31 Weasel words

30:11 Pairing authority with accountability

32:34 Who owns pricing

35:39 One data layer for the whole exec team

37:39 Hiring outside the bubble

40:46 Wrap

MAHESH GURUSWAMY

https://www.linkedin.com/in/maheshguruswamy/

https://www.thesensiblemanager.com

https://www.amazon.com/How-Deliver-Bad-News-Away/dp/B0D7FHTTNN

KEITH COWING

https://linkedin.com/in/keithcowing

https://keithcowing.com

EXECUTIVES UNPLUGGED

https://execs.tv

The hardest part of an AI transformation has nothing to do with the tech. It's breaking the human silos and learning to manage your agents like employees.

Akshit Kandi has mentored over 100 startups and built agents inside Salesforce's Agentforce platform. Now, as CEO of SkySync, he helps companies deploy and manage AI agents. In this episode he walks through the four moves that separate the teams getting real returns from the 90% stuck experimenting. Along the way he unpacks a client that grew new business 300% with a single marketing agent, why fear drives the worst decisions in a transformation, and how to measure ROI with a master dashboard.

00:00 Intro: Akshit Kandi and SkySync

00:48 Why 90% of AI projects are stuck in a pilot

02:22 Manage AI agents like employees

03:45 Inside a 300% growth story

06:55 Why change management is the real bottleneck

09:30 Offense vs. defense: the exec mindset

12:26 The tech decisions behind a true 360° view

15:12 Governance before you scale: CISOs, GDPR, data residency

21:03 Codifying workflows and keeping humans in the loop

23:50 Where to start: internal agents first

26:52 Mining meeting transcripts and existing systems

29:42 ROI dashboards: token measuring, not maxing

30:13 Why Akshit’s building in NYC

Follow Akshit on LinkedIn: https://www.linkedin.com/in/akandi6/

SkySync: https://www.skysync.nyc/

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

Join Keith's Inner Circle: https://execs.tv

Subscribe to Executives Unplugged:

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

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

I've spent the last year building AI agents and working with CEOs doing the same. Most of what I built, I threw out. Here are the 10 rules that survived.

I've been building agents across my coaching practice, content production, and business operations — and the biggest lesson is that the hard part isn't the AI. It's codifying what actually matters in your work and organizing it so agents can use it. In this episode, I break down 10 rules for building agents that are genuinely useful — from structuring your data and building context that compounds, to choosing the right model for the right job, mixing deterministic software with LLMs, and managing agents the way you'd manage a high-performing team. No hype, no theory — just what I've learned from doing it every day. If you've been curious about agents but haven't started yet, this is your playbook.

Chapters

00:00 Introduction

00:44 Rule 1: Put All Your Data in One Place

02:00 Rule 2: Build Context That Compounds

03:28 Rule 3: Design for Rapidly Swapping Models

05:03 Rule 4: Use the Right Model for the Right Problem

06:55 Rule 5: Mix Deterministic Software with LLMs

08:21 Rule 6: Orchestrate Based on Frequency and Value

10:44 Rule 7: Keep Agents Narrowly Focused

12:04 Rule 8: Get Ready to Iterate

12:52 Rule 9: Managing Agents Is a New Skill

15:00 Rule 10: Half of What You Build Is Disposable

17:11 Your Next Steps: Just Start Building

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

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

Subscribe

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

Three top executive recruiters and Foursquare founder Dennis Crowley reveal why the candidate with the perfect resume is usually the wrong hire — and how to find the right one.

Most CEO-CPO relationships fail within the first 18 months and a lot of that pain starts with how the hire was made in the first place.

In this episode, I sat down with three of the best executive recruiters in the business — Chris Running, Jodi Jefferson, and Michael Cullen — plus Dennis Crowley, founder of Foursquare and Hopscotch Labs, to unpack the biggest mistakes founders and CEOs make when hiring their first VP of Product or CPO at Series A through Series C companies.

We cover: why many searches derail, the logo trap that seduces hiring managers into picking the wrong candidate, why you should look for trajectory over altitude, the management answer that's a complete red flag, how AI fluency is reshaping what "great" looks like in a product leader, and what it actually takes to close top talent in a market that's shifting fast.

Whether you're a founder about to make this hire or a product leader evaluating your next opportunity, this episode gives you the playbook from both sides of the table.

Chapters

01:13 Start With Why

03:10 Avoid Logo Trap

04:28 Real Search Example

07:50 Trajectory Not Altitude

08:48 Assess Judgment & Speed

10:52 Culture Fit Walkthrough

12:28 Management In Details

13:59 AI Native Leaders

17:15 Hiring With Conviction

19:23 Candidate Due Diligence

20:48 Align Expectations

23:19 Close The Candidate

25:13 The Market Shift

26:14 Five Takeaways

Find the guests on LinkedIn:

Jodi Jefferson: https://www.linkedin.com/in/jodijefferson/

Michael Cullen: https://www.linkedin.com/in/cullenmm/

Chris Running: https://www.linkedin.com/in/chris-running-a94a8025/

Dennis Crowley: https://www.linkedin.com/in/dpstyles/

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