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Pooja and Stef grill Gurdeep about the lengths he'd go to for his “Dream Girl,” plus it turns out kids don't need much to be happy ...AND... can you do better than us in our Famous 5's quiz?
Pooja tries to sell the gang on spirulina, plus Gurdeep takes the temperature of Leafs Nation ...AND... if you say ‘please' and ‘thank you' to AI, here's why you should stop.
Stef finally buys a ‘grounding mat' and has her review, plus Gurdeep's nephew does something surprising ...AND... Pooja pines for Gurdeep to lose $1,000.
When you fly, do you prefer to sit WITH or APART from your partner? Plus, Gurdeep has group chat anxiety ...AND... Pooja sways Paul on a surprising issue.
Gurdeep tries to explain his ASMR, plus Pooja shares the follies of abbreviating your texts ...AND... we go back in time to re-live our FIRST email address.
Do you ever wonder what your pets get up to when you're not home, plus Gurdeep shares his irrational Playoff superstition ...AND... Pooja tells you why spreadsheets could save your relationship.
Did you know dogs have their own love language, plus Gurdeep reveals his Playoff Survival Kit ...AND... Pooja experiments with a new tactic to bring her closer to her husband.
The gang investigate the widely accepted “5 second rule,” plus Gurdeep stresses about tax season ...AND... Pooja discovers a helpful analogy to help you through tough times.
Gurdeep goes to a Coffee Party for the first time, plus P&G make you feel better about your bad boss ...AND... Pooja wonders if she's TOO affectionate with her kids!
Stef (tries) to explain “Grounding Sheets” to P&G – but they're skeptical, plus Gurdeep finally caves on reality TV ...AND... did you hug your siblings as a kid?
Pooja commits an egregious marital act and we let YOU be the judge, plus Gurdeep explains TLDR ...AND... are receding hairlines sexy now?!
A divorce lawyer has a scorching hot take on WHY women are choosing to get divorced – and it's not why you think. Plus, Pooja plays quizmaster as Gurdeep puts up $1,000 of his own money in Can't Beat Gurdeep.
Gurdeep's phone dies at a very inopportune time, plus the gang share their favourite things to do in a storm ...AND... Pooja explains Adult Tantrum Parties.
Pooja explains Brain Flossing, plus you won't believe what a pilot did at 30,000 feet ...AND... Gurdeep reveals how he got that childhood scar.
Pooja has an awkward moment at a kids birthday party, plus we learn why women are like spaghetti and men are like waffles ...AND... Gurdeep has an “oh my gosh” story!
You won't believe what Gurdeep gets pulled over for on his way to work, plus Pooja digs into Gurdeep's past ...AND... the gang give away Jays tickets in a peculiar way.
Gurdeep's mom is staying at his condo and he's got some concerns, plus Pooja takes a “judgement-free” look at people who still have their Christmas lights on ...AND... Stef tests P&G's memory.
Gurdeep shares a family dilemma about university, plus P&G play Finish The Lyrics to mark the start of Spring, and, err… it doesn't go well.
Pooja discovers a new app but Gurdeep is skeptical, plus the gang talk awkward moments at work ...AND... Gurdeep plays quizmaster in a ridiculous game.
Gurdeep finally gets invited to Pooja's place but quickly regrets it, plus the gang celebrates pi day by crushing a bizarro wheel ...AND... what did you learn about your kids during March Break?
Pooja and Gurdeep discuss their sleep hygiene habits in partnership with Estee Lauder Advanced Night Repair Serum.
Pooja shares a viral story about an alleged pilot and a beautiful woman, plus Gurdeep's feeling guilty after skipping a friend's party ...AND... What's Buggin' Stef about March Break?
Gurdeep celebrates his favourite day of the year (it's better than Christmas!), plus Pooja explains meeting hangovers ...AND... we welcome you into the shower to share your thoughts!
Gurdeep's priorities come into question after he loses his wallet, plus Pooja's left March Break til the last minute ...AND... the gang 'Make It Canadian'.
Gurdeep goes to a WWE match and he's got some observations, plus Pooja's back to work after a trying week at home with the kids ...AND... the gang celebrates your hyperbolic reactions.
P&G discuss the ‘Great Cousins Decline,' plus Pooja's looking for advice after her daughter gets picked on at school ...AND... Gurdeep sees something peculiar on his drive home.
P&G decide it's time to rebrand “The Midlife Crisis,” plus Pooja's got Fitbit problems ...AND... Gurdeep shares something you DIDN'T wanna know about your birthday!
The Gang share the weird things they used to collect as kids, plus Gurdeep takes a dig at Pooja on Be Quiet Day ...AND... Pooja shares an embarrassing auto-correct fail.
In the wake of Canada's massive win, we ask you about the happiest moment of your life, plus Stef 'flaunts' her linguistic skills ...AND... Gurdeep shares his biggest insecurity.
Gurdeep gets a rather egregious parking ticket, plus Pooja waxes poetic on eyelashes ...AND... the gang throws out the highest stakes bet of all time!
We hate to be the ones to tell you: your parents have a favourite child ...AND... Pooja tells Gurdeep about the coolest new party in town; it's NOT what you think.
In a looooove themed episode, Pooja and Gurdeep share a V-Day Rule of Life, plus rank the most romantic date spots in the GTA ...AND... YOU share the worst Valentines gifts you've ever received.
P&G remember a classic 2000s commercial that's getting a second life online ...AND... Pooja snoops into Gurdeep's internet browser history!
Pooja explains the art of time blocking, plus Gurdeep wonders about the national anthem getting booed ...AND... Stef is facing a dinner dilemma!
Do men secretly love romance novels more than women? Plus, Gurdeep comes in hot with an embarrassing admission he's never told anyone ...AND... can you name anything that isn't better pickled?!
Pooja and Gurdeep respond to a “saucy” listener query in Dear P&G, plus Stef provides the lamest excuse to avoid making dinner ...AND... is it time to re-think middle child syndrome?
Pooja interrogates her daughter after Ballpit-Gate, plus Gurdeep comes to a humbling and painful realization about aging ...AND... the gang play a round of “I Love You, But…”
Sia does something at a kids birthday party that stops Pooja in her tracks, plus Gurdeep's cough has him laughing like a lifelong smoker ...AND... the gang rank the Top-3 most irritating office behaviours.
Gurdeep is having a MORNING, plus Pooja's workouts are hitting a new level of lazy ...AND... the gang asks: What are the uniquely weird things your pet does?
Have you ever sent an email and IMMEDIATELY regretted it? Plus, Gurdeep tell us why he can't handle spice like he used to ...AND... Pooja gets curious when her sister leaves behind a magical bottle at her place!
In this episode of the Fail Faster Podcast, Gurdeep Singh, a seasoned solution architect at Chubb with over 25 years in the technology sector, shares his fascinating journey from dismantling radios in his childhood to tackling large-scale modernization projects in financial services. Gurdeep discusses the complexities of legacy system transformation, navigating organizational resistance, and the power of aligning business and technology for impactful change. He also shares his insights on leveraging AI responsibly, building strong data foundations, and fostering collaboration across all levels of an organization. Packed with lessons learned from career-defining challenges and forward-looking strategies, this episode is a must-listen for anyone aiming to modernize systems while keeping people at the heart of innovation.
Is something wrong with Pooja's fitbit or with Pooja herself? Plus, Gurdeep's convinced his algorithms are conspiring against him ...AND... P&G play Would You Rather.
Gurdeep returns from vacay ...AND... tells us what he learned, and Pooja found WHAT in a co-workers desk?!
Gurdeep tosses a bag of something that he's held on to for way too long, plus we'll find out what's bugging Pooja ...AND... Stef brought WHAT to Show & Tell in elementary school?
The uber-safe Pooja shares a rare story of youthful defiance, plus you won't believe what Coffee The Pooch does to Gurdeep ...AND... Pooja re-writes Gurdeep's dating profile.
Gurdeep gets jealous after learning something about Pooja and Stef, plus the gang shares a single word to sum up 2024 ...AND... you tell us the best advice you've ever come across.
You've heard of gentle parenting, but are you familiar with gentle partnering? Gurdeep shares an embarrassing social interaction he caused and Pooja reveals the colour of the year!
Pooja and Gurdeep share the 2024 moments that had them laughing, crying and had the phone and text line ablaze! What were your favs? (let us know in the comments)
Pooja and Gurdeep open up their DMs and answer your questions, including “What are your holiday traditions?”, “Why is Gurdeep Single” and “Did you guys ever have a crush on each other?”
In this episode, Dave is joined by Gurdeep Dhillon, CMO of Contentstack. Gurdeep has built an impressive career leading marketing at some of the biggest names in enterprise software, from SAP to Adobe, Marketo to Zoura. Now at Content Stack, he's challenging conventional B2B marketing wisdom in rethinking how enterprise companies should approach demand generation and brand building. In this conversation, Dave and Gurdeep dive deep into why marketing is ultimately a game of memory and reputation, not just lead generation.Dave and Gurdeep cover:The role of Demand Gen in 2025 (and what's changed)Why Brand and Reputation should be prioritized over Lead GenerationProven strategies to create urgency and close sales deals in enterprise marketsA glimpse into ContentStack's team structure and how they plan for growthTimestamps(00:00) - - Intro to Gurdeep (07:17) - - Brand and Audience Marketing (08:29) - - How the Role of Demand Gen is Changing (12:39) - - Brand and Reputation > Lead Generation (17:29) - - How Contentstack is Doing Demand Gen (20:07) - - How to Create Urgency to Win Sales Deals (21:48) - - Making a Good Offer in B2B Marketing (23:04) - - Why Being Bold and Taking Risks is Important in Marketing (29:29) - - Selling Your Vision to Leadership (32:10) - - How Contentstack Has Over 10,000 Global ICP Accounts (36:53) - - Team Structure at Contentstack (41:51) - - Running Marketing and Operating a High-Performing Team (44:07) - - Setting Effective Annual Plans (46:22) - - AI's Role in Marketing (49:56) - - Closing Thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***This episode of the Exit Five podcast is brought to you by our friends at Revenue Hero. It's 2024, your buyer has probably moved on to an alternative after a few minutes of not hearing from you, let alone 29 hours.What those companies need is automated scheduling for qualified leads.And that's where RevenueHero comes in. Their platform is the fastest way for qualified leads to schedule a meeting with your sales team. Plus they have the most sophisticated matching algorithm so all your leads get booked with the right rep whether they are a new account or already a customer. Check them out at revenuehero.io/exitfive.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more