Revenue Diaries

Kyle Lacy

Revenue Diaries is a podcast and videocast hosted by Kyle Lacy, offering a raw and unfiltered look into the personal lives of the country's top revenue leaders. They discuss everything but work—no topic is off-limits, and there are no wrong questions or answers. The twist? They never see the questions in advance.

  1. 3d ago

    Imposter Syndrome, Eating Disorders, and Professional Ghosting with Caitlin Allen

    Caitlin Allen is SVP of Marketing at Simbe, and we get into the imposter syndrome that still shows up for her, like walking on stage first to accept an award or sitting down for a livestreamed interview. She also opens up about 27 years with an eating disorder and the journal entry that finally cracked it open. She asked herself why she thought something was wrong with her, and the answer came back: “The only reason you believe something’s wrong with you is because that’s what you keep telling yourself.” Jump into the conversation: (00:00) Why do I think something’s wrong with me? (01:36) Ghosting a coffee invite out of imposter syndrome (03:43) What head trash means and how it shows up (05:48) Talking to yourself like a friend (09:04) Making peace with the voice in your head (10:54) Recovering from a 27-year eating disorder (15:12) Handling nerves before a live interview (18:08) Confidence comes from repetition Connect with Cailtin Allen: https://www.linkedin.com/in/caitlinrallen/ Learn more about Simbe: https://www.simberobotics.com/ Connect with me: https://www.linkedin.com/in/kylelacy/  Subscribe to Revenue Diaries: https://www.therevenuediaries.com/subscribe  Produced in partnership with Share Your Genius: https://shareyourgenius.com/

    Imposter Syndrome, Eating Disorders, and Professional Ghosting with Caitlin Allen

  2. Trailer

    What’s Your Head Trash?

    Some of the most successful people you know still feel like they have no idea what they’re doing. Head Trash is my new show about the part of success people rarely talk about: the voice in your head that questions whether you belong, whether you’re good enough, and whether everyone will eventually figure you out. I’ve spent years talking with founders, creatives, operators, and leaders who have built companies, raised millions, and created things people love. From the outside, they look like they’ve made it. Behind the scenes, they’re often dealing with the same doubts and mental noise as everyone else. On Head Trash, we’re going to look at what building something actually costs you mentally and what people do when that internal voice starts trying to screw things up. Some conversations get heavy. Some are funny. All of them are honest. Connect with me: https://www.linkedin.com/in/kylelacy/  Subscribe to Revenue Diaries: https://www.therevenuediaries.com/subscribe  Produced in partnership with Share Your Genius: https://shareyourgenius.com/

    What’s Your Head Trash?

  3. Oct 21

    He Built His Own Sales Company to Get Into Tech with Mark Kosoglow | Carrying Fire

    Mark Kosoglow didn’t wait to get hired into tech. He built his own sales team and pitched his way in. Before he was Chief Revenue Officer at Docebo, he helped scale sales at Outreach from zero to roughly $250 million. Long before any of that, he was selling paper planners and cookie dough fundraisers to schools in small-town Pennsylvania, three and a half hours from Philadelphia. Practically a lifetime away from Silicon Valley. This episode is part of the Carrying Fire series, where I sit down with leaders and innovators to explore how they use continuous learning to navigate massive change and come out stronger on the other side.  Jump into the action: (00:00) Intro (01:29) Meet Mark Kosoglow (04:20) The college notes business and the recruiter who found him  (06:49) His first sales leadership job and the layoff that never had a plan (09:21) The startup podcasts he listened to on the road for years (11:15) Incorporating Mercenary Sales out of pure desperation (17:43) Bench Coach: the app that got him a mention in the New York Times (19:19) Selling Outreach out of his son's gymnastics parking lot (21:23) Manny Medina, the raise nobody saw coming, and asking to be VP of Sales (25:24) The cabin in Pennsylvania and the existential crisis (26:30) Pamela Matson's three things that define an executive (30:33) What was missing at his last job (33:21) Why Mark thinks AI isn't the differentiator Connect with Kyle Lacy: https://www.linkedin.com/in/kylelacy/ Subscribe to Revenue Diaries: https://www.therevenuediaries.com/subscribe Find Mark Kosoglow on LinkedIn: https://www.linkedin.com/in/mkosoglow/ Check out Docebo: https://www.docebo.com/ Produced in partnership with Share Your Genius: https://shareyourgenius.com/

    He Built His Own Sales Company to Get Into Tech with Mark Kosoglow | Carrying Fire

  4. Sep 16

    Two Layoffs, Two Kids, One New House: How To Keep Moving with Anthony Casazza | Carrying Fire

    What do you do when the rug gets pulled out twice? Anthony Casazza knows. He's a senior business analyst at Delta Defense and the Chief Sales and Strategy Officer for Shank It Golf. He's also someone who survived back-to-back layoffs, both while navigating new fatherhood, a new home, and a job market that wasn't cooperating. Anthony and Kyle dig into what it really costs to be laid off twice in short succession, what Anthony learned about remote work and invisible value, and the "fixer identity" that was quietly draining him. Plus: the spiral staircase theory of career growth that Anthony's president shared with him on an eight by ten sheet of paper. This episode is part of the Carrying Fire series, where I sit down with leaders and innovators to explore how they use continuous learning to navigate massive change and come out stronger on the other side.  Jump into the action: (00:00) Intro (01:11) Meet Anthony Casazza (02:27) New baby, new move, first time unemployed against his will (04:39) What the doubt actually feels like and what to do about it (06:27) Upskilling into project management (07:52) The high school connection that changed everything (09:30) Another layoff while at the PGA Expo  (11:11) What the VP of product told him he couldn't quantify (13:08) Shank It Golf: keeping a side hustle alive through career chaos (19:20) The fixer identity and what it cost him (22:54) How to rebuild a value set from the ground up (25:08) How Anthony asked his company president to mentor him (32:08) Advice to past Anthony: the spiral staircase theory of growth Connect with Kyle Lacy: https://www.linkedin.com/in/kylelacy/  Subscribe to Revenue Diaries: https://www.therevenuediaries.com/subscribe  Find Anthony Casazza on LinkedIn: https://www.linkedin.com/in/anthonycasazza/ Check out Delta Defense LLC: https://www.deltadefense.com/  Check out Shank It Golf: https://shankitgolf.com/ Produced in partnership with Share Your Genius: https://shareyourgenius.com/

    Two Layoffs, Two Kids, One New House: How To Keep Moving with Anthony Casazza | Carrying Fire

  5. Aug 19

    The Guy Who Dropped Coffee From His Ceiling on a Zoom Call with James Miller | Carrying Fire

    What happens when a radio host, church historian, and enablement leader walk into a Zoom room with a pulley system delivering his coffee from the ceiling? You get James Miller, Senior Manager of Agent Enablement at Zillow and one of the most genuinely curious people Kyle has ever put a mic in front of. James makes the case that your competitive advantage in the AI era isn't your tech stack or your productivity tools. It's the breadth of what you've let into your brain. The inputs. The weird books. The DnD sessions that didn't work out. He also has some things to say about what AI can and can't do, and why the humans who are most replaceable are the ones who only consume what their job title tells them to.This episode is part of the Carrying Fire series, where I sit down with leaders and innovators to explore how they use continuous learning to navigate massive change and come out stronger on the other side.  Jump into the action: (00:00) Intro (00:38) Meet James Miller and the AI magic show explanation (04:21) Why communication theory is the ultimate degree (08:14) What tools cost us when we stop thinking (11:26) Deletion and a historical perspective on fear (12:33) Why reading without interruption is the new gym (14:25) What it actually means to be a polymath (18:36) The pulley system, the Lumiere Brothers, and remote stagecraft (23:26) Taste as the last human advantage AI can’t replicate (26:36) Change is constant, make peace with being included in it (31:54) Freeing your team from the work they hate (36:13) Advice to church-history Jimmy from today’s Jimmy (39:25) The summer camp fun department Connect with Kyle Lacy: https://www.linkedin.com/in/kylelacy/  Subscribe to Revenue Diaries: https://www.therevenuediaries.com/subscribe  Find James Miller on LinkedIn: https://www.linkedin.com/in/j4messmiller/ Check out Zillow: https://www.zillow.com/ Produced in partnership with Share Your Genius: https://shareyourgenius.com/

    The Guy Who Dropped Coffee From His Ceiling on a Zoom Call with James Miller | Carrying Fire

  6. Jul 22

    You're Never Going to Feel Ready. Change Anyway with Richard Banfield & Devon McDonald | Carrying Fire

    What does a former design agency CEO who lost his wife, his business, and his identity have in common with a high-achieving VC investor whose body was keeping score long before her brain caught up?  Richard Banfield and Devon Warwick McDonald, co-founders of Second Harvest, bring the design thinking principles of MVP and experimentation to one of the most overlooked challenges in professional life: the midlife pivot. They make the case that the same logic that validates a product idea (small experiment, get evidence, build from there) is exactly what works when the thing you're testing is your own second chapter. This episode is part of the Carrying Fire series, where I sit down with leaders and innovators to explore how they use continuous learning to navigate massive change and come out stronger on the other side.  Jump into the action: (00:00) Intro (00:35) Introducing Second Harvest and how it started  (01:57) About OpenView, loss, and pandemic clarity  (06:01) How misalignment shows up in your relationships  (10:48) Why some people see misalignment and still don't act  (11:50) The mantra that changes everything  (17:00) The thin slice experiment: an MVP for your personal life  (19:08) Why your LinkedIn profile is the number one obstacle to change  (23:36) The disease of turning every passion into a business  (26:34) How success is built on dysfunction  (32:31) There's no generic solution and that's the whole point (36:27) Three things only humans can do that machines can't replicate  (41:45) The relationships you have while you're changing are the most important ones  (44:36) The loneliness nobody talks about at the C-suite level Connect with Kyle Lacy: https://www.linkedin.com/in/kylelacy/ Subscribe to Revenue Diaries: https://www.therevenuediaries.com/subscribe Connect with Richard Banfield: https://www.linkedin.com/in/richardbanfield/Connect with Devon Warwick McDonald: https://www.linkedin.com/in/devonemcdonald/ Check out Second Harvest: https://secondharvest.co Produced in partnership with Share Your Genius: https://shareyourgenius.com/

    You're Never Going to Feel Ready. Change Anyway with Richard Banfield & Devon McDonald | Carrying Fire

  7. Trailer

    Introducing the Carrying Fire Series

    In a world where change happens faster than most people can keep up, how do you stay ahead? The answer isn’t just about being smart or lucky. It’s about learning. Conversations that delve into the journeys of leaders, operators, and innovators who embraced learning to stay relevant in the face of massive change. In a world where technology, remote work, and evolving team structures are rewriting the rules of work, this series explores how adapting and learning rather than standing still has become the key to survival. Hosted by Kyle Lacy, each episode in this series features authentic conversations with people who have navigated disruptive shifts and emerged stronger. The show highlights the power of continuous learning, whether that means upskilling, rethinking team dynamics, or tackling personal challenges. It's about real stories, real people, and how they leveraged learning to thrive in an ever-evolving work landscape. Forget about predicting the future or following trends.  Carrying Fire is about staying in the game and finding ways to win amidst change. Listen in for insightful discussions with those who've confronted change head-on and emerged as survivors because the future is for learners. Subscribe and get inspired to keep adapting, evolving, and staying relevant in this fast-changing world.

    Introducing the Carrying Fire Series

  8. 10/22/2025

    Episode 17: Parenting, Purpose, and the Drive to Do More with Brendan Hufford

    Success doesn’t come from chasing comfort, it comes from confronting yourself and choosing to grow anyway. In this episode, I sit down with Brendan Hufford, former principal turned content strategist and founder of Growth Sprints. Brendan opens up about the lessons that shaped him, from growing up in a single-parent household and learning the value of drive, to finding balance between ambition, family, and self-awareness. They talk about the discipline that comes from martial arts and CrossFit, the humility of parenting four boys, and how sobriety forced Brendan to face life with clarity and intention. Brendan shares what it means to trade rage for resilience, how writing became therapy, and why strength: physical, emotional, and creative, is only meaningful when it’s used to care for others. Timestamps: (00:00) Intro (01:25) Brendan's background in education (02:33) From principal to content strategist (08:47) Brendan's MMA and Jiu-Jitsu journey (14:26) Balancing ambition and family life (23:59) The chaos of raising boys (24:46) Parenting challenges and reflections (27:44) Teaching and learning psychology (29:21) The world of online marketing (31:42) The power of writing and journaling (37:05) Rapid fire questions Connect with my guest: Brendan Hufford on LinkedIn: https://www.linkedin.com/in/brendanhufford/ Explore Growth Sprints: https://growthsprints.co/ Connect with me: Kyle Lacy on LinkedIn: https://www.linkedin.com/in/kylelacy/ Explore Docebo: https://www.docebo.com/ Produced by our partner, Share Your Genius: https://shareyourgenius.com/?utm_source=shownotes&utm_medium=pod&utm_campaign=rev-diaries

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About

Revenue Diaries is a podcast and videocast hosted by Kyle Lacy, offering a raw and unfiltered look into the personal lives of the country's top revenue leaders. They discuss everything but work—no topic is off-limits, and there are no wrong questions or answers. The twist? They never see the questions in advance.

Information

  • Creator
    Kyle Lacy
  • Years Active
    2025 - 2026
  • Episodes
    25
  • Rating
    Explicit
  • Copyright
    © Kyle Lacy
  • Show Website
    Revenue Diaries