The Bottom Fell Out. How They Stayed: Laid Everyone Off, 700 Rooms on 3 Staff, Sold for $300M

Ten founders and business leaders sit down with Nick Madden to break down what it actually takes to start and grow a business, back to back, in one episode: Flip Howard, Rob Kaczmark, Joe Pomerenke, Raul Hernandez Ochoa, Jeremy Aranda, Bob Hogan, Tim Lyons, Phil Berry, Rob Hays and Jeff Schiefelbein. These are the moments that don't make the headlines: a first business that should have been a dry cleaner on the corner, a sales career that started by failing miserably and ended in a billion-dollar business, a $7 million raise that nobody took seriously, the rule for doing business with your dad and brothers, and why the people who make it are the ones who decide failing is not an option. Then the hard ones. Phil Berry won an account that turned out to be six times his revenue, hired off the street for 60 days, and lost it at day 45 with $750,000 of inventory on his shelves. In March 2020 the public hotel company where Rob Hays was an executive furloughed 93% of almost 13,000 associates in a weekend; a month later the board made him CEO. Jeff Schiefelbein's energy company went from doing okay to losing about a million dollars a day. Phil Berry negotiated an exit, laid everybody off and realized 'we're still here'; Rob Hays kept the hotel company out of bankruptcy and ran it through five years; Jeff Schiefelbein's energy company was saved and sold three years later for $300 million. The thread, in the words Rob's father gave him: every business person needs to stare into the abyss at least once to figure out what they're made of. For Catholic business owners, that is what grit, perseverance and faith look like when the numbers go the wrong way. ==== Breaking the Barrier's Founding Sponsor: US Digital PartnersUS Digital Partners provides full-service digital marketing support rooted in Catholic values. Need help navigating marketing strategy, lead generation, or even AI search visibility? ⁠ Start here: https://www.usdigitalpartners.com/ ==== Chapters 0:00 Intro: ten founders, back to back 1:17 Flip Howard: just don't suck 6:51 Rob Kaczmark: scale the unscalable 9:33 Joe Pomerenke: fail fast, $100M to $1B 12:04 Raul Hernandez Ochoa: define growth first 18:28 Jeremy Aranda: doing business with family 20:19 Bob Hogan: $7 million was the wrong number 24:15 Tim Lyons: effectiveness before efficiency 27:07 Phil Berry: six times the revenue, gone in 45 days 34:07 Rob Hays: April 2020 and the call to Dad 40:49 Jeff Schiefelbein: saving a company losing about a million a day 42:48 Outro ______________________ Connect Subscribe to Breaking the Barrier and download the Leader Guide for this episode to use with your leadership team or small group. Evergreen footer — paste verbatim into every YouTube description ___________________ ► JOIN THE MOVEMENT: #BESENT Learn More - https://www.sentventures.com?utm_sour... Join us for SENT Summit 2026 in Denver, CO - https://www.sentventures.com/sentsumm... ______________________ ► SUBSCRIBE TO BREAKING THE BARRIER iTunes - https://podcasts.apple.com/us/podcast... Spotify - https://open.spotify.com/show/1k5gtLQ... ______________________ ► FOLLOW SENT VENTURES   / sententrepreneurs     / sentventures     / sentventures   https://x.com/SentVentures