Some of the most successful people you know still feel like they have no idea what they’re doing.
Head Trash is Kyle Lacy’s show about the voice in your head that questions whether you belong. Kyle sits down with founders, creatives, operators, and leaders who look like they’ve made it to get honest about what building something costs you mentally and what they do when that voice starts trying to screw things up.
This show is a Revenue Diaries Joint, bringing the same raw, unfiltered conversations to the noise inside your head.
Imposter Syndrome, Eating Disorders, and Professional Ghosting with Caitlin Allen
Caitlin Allen (https://www.linkedin.com/in/caitlinrallen/) is SVP of Marketing at Simbe (https://www.simberobotics.com/), 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/ (https://www.linkedin.com/in/caitlinrallen/)
Learn more about Simbe: https://www.simberobotics.com/ (https://www.simberobotics.com/)
Connect with me: https://www.linkedin.com/in/kylelacy/ (https://www.linkedin.com/in/kylelacy/)
Subscribe to Revenue Diaries: https://www.therevenuediaries.com/subscribe (https://www.therevenuediaries.com/subscribe)
Produced in partnership with Share Your Genius: https://shareyourgenius.com/ (https://shareyourgenius.com/)
29 Oct 2026
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/ (https://www.linkedin.com/in/kylelacy/)
Subscribe to Revenue Diaries: https://www.therevenuediaries.com/subscribe (https://www.therevenuediaries.com/subscribe)
Produced in partnership with Share Your Genius: https://shareyourgenius.com/ (https://shareyourgenius.com/)
21 Oct 2026
He Built His Own Sales Company to Get Into Tech with Mark Kosoglow | Carrying Fire
Mark Kosoglow (https://www.linkedin.com/in/mkosoglow/) 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 (https://www.docebo.com/), he helped scale sales at Outreach (https://www.linkedin.com/company/outreach-saas/) 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/ (https://www.linkedin.com/in/kylelacy/)
Subscribe to Revenue Diaries: https://www.therevenuediaries.com/subscribe (https://www.therevenuediaries.com/subscribe)
Find Mark Kosoglow on LinkedIn: https://www.linkedin.com/in/mkosoglow/ (https://www.linkedin.com/in/mkosoglow/)
Check out Docebo: https://www.docebo.com/ (https://www.docebo.com/)
Produced in partnership with Share Your Genius: https://shareyourgenius.com/ (https://shareyourgenius.com/)
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