In The Pocket with Alisha Esmail

Alisha Esmail
  • 5.0 (1)
  • Entrepreneurship
  • Weekly

In The Pocket is for founders who want to build something meaningful without losing themselves in the process. Hosted by Alisha Esmail, founder of Latch AI and creator of the Five Tanks Framework. From building an award-winning coffee brand to running an AI company, Alisha covers what it actually takes to grow a business while keeping your energy, your relationships, and your sanity intact. Business performance meets personal performance. No fluff. No guru energy. Just real conversations about retention, AI, founder life, and what it looks like to stay in the pocket.

Episodes

  1. Oct 21

    Shaun Clark, Co-Founder of HighLevel | Bootstrapping, Churn, and What AI Can’t Replace

    “Just because there’s a cool tool doesn’t mean you have to use it. Just expect the right people to use it and give you the benefits.” Shaun Clark is a college dropout who spent 12 years building the world’s largest answering service, a $30 million operation serving 5,000 small businesses, before he ever touched the thing he is now known for. That thing is HighLevel, the all-in-one platform tens of thousands of agencies run their entire business on, quietly powering the operations of millions of small businesses underneath them. He and his co-founder bootstrapped it, took almost no outside money to run it, and still own and run it today. At their scale, that is close to unheard of. This conversation is a masterclass in building something real without losing yourself in the noise. What we get into: The 12 years answering missed calls that taught him speed to lead is everythingWhy he never raised money to run the business, and the founders he watched get thrown out of their own companies for doing the oppositeThe failures the highlight reel skips: a mobile app, Service Pro Max, and a HighLevel 1.0 that was almost dead on arrivalThe agency partner who worked two years for free before they handed him a third of the company, and the lesson that came with it: give firstWhy local agencies have almost no churn and the industry “ninjas” churn through the roofHow HighLevel uses AI by following customers instead of chasing toolsThe tree-cutting analogy every founder drowning in AI needs to hearWhat he would do with unlimited resources and no chance of failureChapters: 00:00 What it means to be in the pocket01:23 Meet Shaun Clark, co-founder of HighLevel01:36 Twelve years building the world’s largest answering service04:47 The best advice his mom ever gave him06:21 Why they never raised money to run the business08:06 Revenue over raising, and staying in the driver’s seat10:11 From version one to HighLevel: the failures nobody sees15:10 The lead-nurture aha moment that changed everything17:14 Give first: the partner who worked for free18:47 Community over paid ads, and knowing your weaknesses22:55 What separates agencies that retain clients from the ones that churn26:47 AI: following customers instead of chasing tools30:45 Buy versus build, and the trap of vibe coding31:33 The tree-cutting analogy: decide what business you are actually in36:08 Unlimited resources, no failure: what would he do37:26 Where to find Shaun and HighLevel About Shaun Clark: Shaun is the co-founder of HighLevel, the all-in-one platform thousands of agencies and small businesses run on. Before HighLevel he built the world’s largest answering service and founded Invoice Sherpa. About the show: In The Pocket is a show about building something meaningful without losing yourself in the process. Hosted by Alisha Esmail. Follow so you never miss an episode.

  2. Aug 25

    Why Satisfied Customers Aren't Loyal, and How to Build Superfans, Brittany Hodak

    Brittany Hodak built fandom for some of the biggest names on the planet, Taylor Swift, Dolly Parton, KISS, then took everything she learned about superfans and turned it into a system any business can use. She scaled her company to eight figures, walked into Shark Tank and left with offers from four of the five sharks, and wrote the book on it: Creating Superfans. In this episode, Brittany and Alisha get into why retention is a lagging indicator (and why a renewal isn't the win you think it is), the simplest way to find out where your growth actually comes from, and why "satisfied" is the most dangerous place a business can be. Brittany shares the "how did you hear about us" loop that turns one client into many, why apathy (not competition) is the real villain, and her hot take on AI in customer experience: done well it feels like a trusted friend, done wrong it feels like a creepy stalker. Then the harder half. Brittany pours everything into helping other people feel seen. Alisha asks how she keeps her own tanks full. Her honest answer on burnout, the physical tank she fights to protect while flying 125 times a year, and what she'd do with unlimited resources (hint: it involves space) make this a conversation about building something people love without losing yourself in the process. Guest: Brittany Hodak, author of Creating Superfansbrittanyhodak.com | Creating Superfans podcast Host: Alisha Esmail, founder of Latch AI and creator of the Five Tanks Frameworkalishaesmail.com | yourlatch.com

  3. Aug 15

    How to Build a Multi-Million Dollar Company Without Losing Yourself, Kelly Jedele

    Kelly Jedele built a multi-million dollar company with a mop and a phone. She started Let Kelly as a single mom in Austin, cleaning houses herself, and grew it into one of the most trusted home management companies in the city, hundreds of clients and dozens of employees over 17 years. But building the successful thing, the thing that looks great from the outside, taught her something nobody warns you about: you can have it all and still feel completely disconnected from yourself. In this episode of In The Pocket, Kelly and Alisha get into: 00:00 IntroWhy consistency, not complexity, is what actually keeps customers, and why "the magic is when you get bored"What running a business inside people's homes taught her about trust and loyaltyHow communicating fast when something breaks turns a mistake into a loyal client"Focus means no": why her no list is longer than her yes listGlass balls vs rubber balls, and the one she dropped on purposeGetting fired, rebuilding, and learning that when she bets on herself she always winsThe harder half: success without alignment, the childhood loss that shaped her worthiness, and the work behind healing itThe tanks she still fights to keep full, and what lights her up most now A conversation about building something that matters without losing yourself in the process. CONNECT WITH KELLYLet Kelly (home management): letkelly.com | @letkellyCoaching & speaking: kellyjedele.com | @kellyjedele CONNECT WITH ALISHAWebsite: alishaesmail.comLatch AI: yourlatch.comInstagram: @alisha.esmail In The Pocket is the show about what it actually takes to build something meaningful without losing yourself in the process. New episodes regularly. If something hit, share it with a founder who needs to hear it.

  4. Aug 15

    Why Hiring (and Keeping) Great People Starts With You, Robert Syfert

    Robert Syfert spent a decade building software companies, scaled a team past 120 people, and had a successful exit. Instead of taking the break most people would, he started over in a completely new category. Today he's co-founder and CEO of Hero Hire, an AI recruiting engine that replaces traditional recruiters with autonomous agents searching more than 800 million profiles around the clock. In this episode, Robert and Alisha get into: Why hiring feels hard for founders, and the fear underneath itThe "Wizard of Oz" model: how to run a business on AI agents and where the human line actually isWhy accountability without clarity is the root of almost every retention problem, in hiring and in clientsWhat a bad hire or bad-fit client really costs (six figures plus lost momentum)The early signals in the first 30 days that a placement won't stickWhether AI agents will replace humans, and which industries change firstThe physical tank Robert has fought his whole life, the childhood triggers beneath it, and the habits and nervous-system work that keep him steady while building a company and moving his family across the continentA conversation about building something big without losing yourself, and the people, in the process. Connect with RobertHero Hire: herohire.aiRobert is on all major platforms under his own name Connect with AlishaWebsite: alishaesmail.comLatch AI: yourlatch.comInstagram: @alisha.esmail In The Pocket is the show about what it actually takes to build something meaningful without losing yourself in the process. If something hit, share it with a founder who needs to hear it.

  5. Jul 6

    EP 03: Silent Churn - Your Best Client Left and You Didn't Notice

    I was at the dinner table with my family when the email came in. Our biggest client, 50% larger than any other account we had, in four words: "Going a different direction." I had no idea it was coming. And that email is the reason this show exists. This is a solo episode, and it's the most honest one I've recorded. I take you back to the moment I lost our largest client at Road Coffee, the brand I built into the largest in the province, and I walk through every signal I missed. Not as a junior account manager who dropped the ball. As the founder who was in the room and still didn't see it coming. Here's what I've learned since. Silence isn't satisfaction. It's the exit ramp. The decision to leave doesn't happen when the email lands. It happens weeks earlier, in signals most founders are never taught to read. In this episode: Why rising orders can hide a client who's already gone. The 30-day drift window and the exact signals that show up inside it. Why quiet clients are the ones to watch, not the loud ones. The retention math most founders ignore while chasing new leads. The manual health-scoring system I built that tripled our retention. And how every one of your Five Tanks drains when your biggest client walks. If you're a founder who assumes no news is good news, this one's for you. Go check on your quietest client. Not with a pitch. With a real question. In The Pocket with Alisha Esmail. Build the business. Keep yourself.

  6. Jun 11

    From Clinic Floor to Coaching Chair, Karen Elliott on Building a $4M Practice and Walking Away

    Karen Elliott built a one-woman physiotherapy practice into a 35-person, $4M multi-disciplinary clinic. Then she sold it. Not because it was failing. Because she realized she had become the bottleneck in the thing she built. In this episode, Karen talks about what it actually felt like to let go of something she poured 20 years into, why she went right back into the clinic world as a coach instead of walking away, and what she sees clinic owners getting wrong when it comes to keeping their best patients and their best people. Karen is the founder of Lead With Purpose and is known as the Queen of Difficult Conversations. She now coaches clinic owners and business leaders across North America on team alignment, operations, and stepping into the visionary role without burning out. We get into: The moment she knew the way she was running things couldn't scaleWhat selling your business actually feels like (not the highlight reel version)Why most clinic owners are hemorrhaging patients without realizing itThe conversations leaders avoid that cost them their best team membersHer Five Tanks check-inFind Karen: toleadwithpurpose.com | @bykarenelliott on Instagram

  7. Jun 1

    EP 01: The Five Tanks: Why Winning Founders Still Feel Like They're Losing

    You can be winning on every measurable metric and still feel completely empty. That's not a motivation problem. That's a tank problem. In this first episode of In The Pocket, Alisha Esmail introduces the Five Tanks Framework, a system she built after years of burning out while building Road Coffee Co into an award-winning national brand. The Five Tanks are Emotional, Mental, Spiritual, Relational, and Physical. When they're full, you're in the pocket. When they're low, you make decisions you'll regret, relationships quietly fall apart, and you win things you can't feel. This episode covers: What it actually looks like when each tank is empty (real stories, not theory)Why balance is a myth and harmony is the goalThe one-minute tank check that tells you exactly where your next hour should goWhy you cannot separate the founder from the businessBy the end of this episode, you'll have rated your five tanks and know which one needs your attention today. Take a minute right now. Rate each tank 1 to 10. Whichever is lowest, give it one hour today. That's how you stay in the pocket.

  • 7 Episodes

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About

In The Pocket is for founders who want to build something meaningful without losing themselves in the process. Hosted by Alisha Esmail, founder of Latch AI and creator of the Five Tanks Framework. From building an award-winning coffee brand to running an AI company, Alisha covers what it actually takes to grow a business while keeping your energy, your relationships, and your sanity intact. Business performance meets personal performance. No fluff. No guru energy. Just real conversations about retention, AI, founder life, and what it looks like to stay in the pocket.

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