Breaking the Barrier

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.

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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/

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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

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David Mount sits down with Nick Madden to break down what Silicon Valley gets right when it is working at its best, and what any founder can take from it. David, founder of G2 Venture Partners, spent 10 years at Kleiner Perkins before his team spun out to invest where technology meets industry and energy.

He explains his mentor John Doerr's line between missionary and mercenary founders, why venture is a repeat game, the old investor's line that only desperate people buy from startups and how G2 spends dozens of customer calls finding out why, the test of a mediocre salesperson hitting quota, and why founders should raise the right amount of capital rather than all they can.

The personal stakes come in his late 20s and early 30s: a fourth child, a minivan, and LP meetings to raise a fund. When starting G2 with four young kids became too much, mentors told him to take some time at the beginning of the day and pray; for 10 to 15 years that morning practice has been how he gets back to the order: loved by God, then husband, then dad, then work.

For Catholic business owners who wonder whether faith fits in a boardroom, his answer to whether being Catholic in Silicon Valley is a challenge is 'No, like full stop, no.' Build something people are desperate for, sell it by solving their problem, and keep the order straight.

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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/

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Chapters

0:00 It was too much: a fourth kid and a fund to raise

1:10 From Bellarmine to Kleiner Perkins to G2

3:41 What Silicon Valley gets right

5:22 Missionary vs. mercenary founders

7:57 The repeat game

17:33 What investors look for in founders

20:24 Why only desperate people buy from startups

31:24 Capital, labor, and autonomous forklifts

42:21 Nonprofit or company? Selling as solving a problem

50:06 Recency bias and the scoreboard

53:51 Loved by God, then husband, dad, work

1:01:47 Rapid fire and finding faith in the Valley

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About the guestDavid Mount is the founder of G2 Venture Partners, a growth-stage venture firm investing where technology meets industry and energy. He grew up in San Jose, went to the Jesuit high school Bellarmine, and spent 10 years at Kleiner Perkins before his team spun out to form G2. He and his wife have four kids.

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Ben Davis sits down with Nick Madden to break down how a 24-year-old with three years of experience walked away from the number-two seat at a fast-growing insurer, signed an SBA loan two weeks before Lehman Brothers collapsed, and opened a luxury barbershop club on the day of his son's second open-heart surgery.

Ben built The Gents Place with his wife into a national membership-based barber and business club through franchising, and along the way learned the hard lessons of brick-and-mortar: the root beer run that made a raving fan, why he pulled the phones out of every location, what three units prove that one never can, and why the systems have to be the best manager.The turning point was not a number. Eighteen months in, churning stylists who wanted 32-hour weeks, Ben stepped back and admitted the business was not working because he was not.

With a change of heart, the business now exists, in his words, to make as much money as it possibly can so that it can then serve. That means 65,000 meals to homeless veterans, 12,000 pieces of professional clothing, and an annual suit drive at Fort Hood's Soldier Recovery Unit. For Catholic business owners wondering whether ambition and service can share a building, this episode is the case study: love your people, build the system, and let the profit fund the mission. And his son Pierce, multiple open-heart surgeries later, has now made a college basketball team.

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Breaking the Barrier's Founding Sponsor: US Digital Partners

US 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

====

Chapters

0:00 That's not smart: a $2,000-an-hour warning

0:41 Welcome and who Ben Davis is

3:18 Goosehead, a sick son, and an SBA loan two weeks before Lehman

11:36 The hardened heart: churning a team for 18 months

18:57 Raving fans and the root beer run

23:24 Direct, compassionate communication and the Wednesday 9am call

35:38 Leave better than you came in

39:39 The home for ambitious gentlemen

47:39 Pierce: open-heart surgeries to college basketball

52:02 A faith journey and the truth behind the self-help

58:14 Pulling the phones, franchising, and three units

1:08:01 Make money so you can serve, then rapid fire

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About the guest

Ben Davis is the co-founder of The Gents Place, a national membership-based barber and business club he started in 2008 with his wife and grew through franchising. He built Gents TV, has invested in several other businesses, and hosts a podcast of his own; through The Gents Place his community has served more than 65,000 meals to homeless veterans and donated more than 12,000 pieces of professional clothing.

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Breaking the Barrier's Founding Sponsor: US Digital Partners

US 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

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Bahigh Acuna sits down with Nick Madden to break down the part of a business most founders overlook: the go-to-market. Bahigh was Spotify's first man on the ground in Mexico when music streaming sounded like a scam ($9 a month for millions of songs, from a startup in Sweden), and he walks through how trust actually gets built: knocking 20 doors with zero users until Coca-Cola became the launch partner, giving up Spotify green for red and white to get it, and the launch-day translation blunder that went viral and taught him you cannot use a US agency to launch in Latin America. From there the toolkit widens: Amazon's empty chair and writing the press release first, Ancestry's DNA product flipping the customer, and why the hardest customer is the one worth cracking.

Bahigh bet on streaming when his parents questioned the move and his friends called it a tiny startup that couldn't win, then, as Spotify's 'first man on the ground' in Mexico, helped deliver what he calls 'the biggest, most successful launch in Spotify's history' by earning trust through a Coca-Cola launch partnership (compromising on the brand color to get it) and a real cultural layer. He carried those playbooks through Ancestry and Amazon and now deploys them into other companies (market development, the US Hispanic segment, partnership architecture, AI) while preparing to teach at the University of Dallas so students graduate 'with an asset, with a revenue generating company.' The faith through-line resolves the same way: his Catholic faith 'is in my OS,' lived through high integrity rather than flag-waving, anchored by prayer before he opens his eyes and surrender to the Holy Spirit at night. For Catholic business owners, that is the whole episode: earn trust before you ask for anything, keep the customer in the room, and let integrity do the talking before your faith does.

Chapters

0:00 Zero users, the biggest fish, and the fourth leg

2:36 When $9 a month sounded like a scam

8:57 Day one at Spotify and the launch-day blunder1

6:16 Knock 20 doors: how Coca-Cola said yes

24:51 The empty chair: know your customer

30:08 Write the press release first

35:08 Trust, the Holy Spirit, and his mother's rule

41:47 Being Catholic in big tech: integrity first

44:44 What he's building now, and the US Hispanic market

55:40 IQ becomes a commodity: creativity, taste, community

1:04:37 Faith as the operating system, AI, and UD

1:10:28 Habits, rapid fire, and focus over energy

About the guest

Bahigh Acuna is a tech entrepreneur and go-to-market strategist who spent time building Spotify (first man on the ground in Mexico), Ancestry (the DNA product launch) and Amazon (corporate business development). He now helps companies with market development, the US Hispanic segment, strategic partnership architecture and AI, and is a University of Dallas alum preparing to teach entrepreneurship there. He and his wife have four kids under six.

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Breaking the Barrier is Sponsored by US Digital Partners (founding sponsor). Find out how US Digital Partners helps chip away at your goals by delivering a customized roadmap of marketing tactics and methodically at www.usdigitalpartners.com

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ABOUT

Phil Berry sits down with Nick Madden to break down how a distributorship doing $400,000 a year, bought on a cashed 401(k), became a health company running near $100 million. Berry spent his first five years in survival mode, juggling payables and coaching his kids in the afternoons, before winning the biggest account in his company's history — 50 clinic sites, roughly six times his annual revenue, landing all at once. Forty-five days later the client was acquired, he went to Milwaukee to re-sell it in his best suit, nailed the presentation, and lost it anyway. That left $750,000 of inventory on his shelves and a staff he had to lay off.

He stopped surviving deal to deal and started moving with intention — naming the self-funded employer market, bootstrapping a mail-order pharmacy, and coming to hold the company as something he stewards rather than owns. Northwind has since grown 40X in seven years to roughly $100 million in revenue, serving about 200,000 people. Along the way Berry lays out why American healthcare costs keep climbing while people get less healthy, why nobody in a $5 trillion industry is paid for the outcome everyone claims to want, what he tells his team about using AI without outsourcing their own thinking, and the 4:30 AM holy hour that orders the rest of it.

Chapters

0:00  $750,000 on the Shelves

0:53  Meet Phil Berry

3:06  Sales, Branch Offices, and a Restless Start

15:38  Telemedicine, Leverage, and Buying a Business

23:28  Five Years of Survival, and What the Family Felt

36:03  The Biggest Account He Ever Won, and Lost

42:44  Moving With Intention

48:21  Not Yours to Own: Becoming a Steward

58:54  Why Nobody Is Paid to Make You Healthier

1:16:47  AI, Agency, and Human Flourishing

1:38:48  The Holy Hour and the 4:30 AM Routine

1:48:22  Rapid Fire and the Closing Word

About the guest

Phil Berry is the founder and CEO of Northwind Health, which helps companies with self-funded health plans control costs by producing health in their members and reducing waste in plan design.

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Episode description

Raul Hernandez Ochoa sits down with Nick Madden to break down what AI actually changes for a business owner. Raul — founder & CEO of Do Good Work, who's helped generate $50M+ in revenue and overseen $25M+ in ad spend across teams in 12+ time zones — argues the real prize isn't cutting costs. It's 'net-new value': taking a client past 'finished,' and building a locally-owned AI 'harness' on your own IP so you point your best hours at the problems only judgment can solve. Along the way: the three stages (automation, augmentation, net-new value), why leaders can't delegate AI, the 80/30 buy-in gap between executives and the frontline, and the one thing no machine can ever do.

The turnaround: Raul now runs a custom, locally-owned AI 'harness' built on his own IP with nine points of human flourishing coded in as hard rules -- compressing 20-plus hours of client work into one to three hours and pouring the freed time into the net-new value and human relationships only people can create. For Catholic business owners, that's the whole point: AI as a tool to serve the person, not replace them -- 'the economy is just humans helping humans.'

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Breaking the Barrier's Founding Sponsor: US Digital Partners

US 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

====

Chapters

0:00  20 hours of work, done in one

0:44  Meet Raul Hernandez Ochoa

3:12  From broke to bootstrapped

12:48  Define 'growth' before you chase it

18:17  The visionary trap & owning your AI moment

25:20  Automation, augmentation, net-new value

34:22  Real examples: experience, donors, outbound calls

44:15  Own your data, models, and harness

46:12  Nine points of human flourishing

53:15  The one thing AI can never do

1:04:51  Rule of life & keystone habits

1:12:25  Rapid fire + a word for the founder in the grind

About the guest

Raul Hernandez Ochoa is the founder & CEO of Do Good Work (dogoodwork.io), where he helps founders scale operations, build healthy cultures, and deploy AI without losing the human person. As stated in the episode intro, he has helped generate over $50 million in revenue and overseen more than $25 million in ad spend across global teams in 12+ time zones.

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Breaking the Barrier is Sponsored by US Digital Partners (founding sponsor). Find out how US Digital Partners helps chip away at your goals by delivering a customized roadmap of marketing tactics and methodically at www.usdigitalpartners.com

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Episode description

Christopher Check, president of Catholic Answers, sits down with Nick Madden to break down what it means to run a mission like a business — and why faith and work were never two separate fields. A former US Marine Corps artillery officer and nearly two-decade media leader, Check has helped grow the largest lay-run Catholic apologetics apostolate to its best year ever, and he talks candidly about measuring excellence by transformed lives, the stewardship owed to a widow's-mite donor, why authentic persuasion aims to win a soul and not an argument, what AI is quietly costing the craft of writing, and how leaders are formed by visible example and local, incarnate community.

Check's answer isn't a hack but a discipline: refuse to let the bottom line compromise the mission, form virtue in the daily craft, lead by visible example, and build for families and local places — all ordered to one secret he names, to let all your actions be done out of love of Jesus Christ. For Catholic entrepreneurs building companies and families at the same time, it reframes the barrier between Sunday and Monday as no barrier at all: the church is the gridiron, and business is mission.

Chapters

0:00  Welcome to Breaking the Barrier

0:50  Meet Christopher Check & Catholic Answers

6:00  Business is mission — there's no neutral ground

10:27  Running a mission: nonprofit vs. for-profit

20:38  Stewardship and the widow's mite

22:45  Apologetics: win a soul, not an argument

30:52  Media, atomization, and real Main Street

36:43  AI and the art of writing

48:49  Leadership by example

54:35  Why local enterprise matters

67:01  A rule of life

71:19  Rapid fire, time, and the secret of life

About the guest

Christopher Check is the president of Catholic Answers, the largest lay-run Catholic apologetics apostolate. A former US Marine Corps artillery officer, he spent nearly two decades in media before leading the apostolate.

Resources mentioned

• Catholic Answers — catholic.com

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Joe Pomeranke sits down with Nick Madden to break down how you build a business worth a billion dollars — and then give it back to the people who built it. Over nearly two decades at Arco, Joe helped grow a design-build firm from roughly $100M to $1B+, compounding at more than 50% a year for eleven years, on one conviction: in a service business, people are your only asset. He walks through what an ESOP actually is, why he'd tell associates to bet on themselves instead of a 401k, the real difference between leadership and management, the discipline of 'managing by absence,' and why he now believes AI calls for hope, not fear.After nearly two decades building Arco from roughly a $100M into a $1B+ design-build business (growing ~50%+ for eleven years), Joe led its transition to employee ownership through an ESOP — returning the company's value to its associates (the 'thousand people millionaires,' with modeled retirement benefits about three times that). He has since moved into a season of philanthropy, investing in and mentoring entrepreneurs, having discovered in his early 40s that the real reward is joy — creating happiness in others — which he calls living heaven on earth. For Catholic founders and CEOs, it's a rare, practical look at building enterprises that serve the people inside them — and staying grounded while the tools and the money move fast.Chapters0:00 Welcome, and introducing Joe1:56 Arco, and why people are the only asset5:33 Failing fast, and the mentors who shaped him7:55 The ESOP: giving the company back to its people9:19 What an employee-owned company actually is13:50 Leadership vs. management17:02 Managing by absence19:12 The leader as steward22:00 AI, the Church, and hope over fear26:36 Patience, impatience, and love31:38 Happiness vs. joy34:55 Rapid fire and closing encouragementAbout the guestJoe Pomeranke spent nearly two decades at Arco, a national design-build company, helping grow it into a billion-dollar business before transitioning it to employee ownership. He now mentors and invests in entrepreneurs and works in philanthropy.=========Follow Breaking the Barrier and subscribe wherever you get your podcasts. Learn more at sentventures.com/breaking-the-barrier.=========► JOIN THE MOVEMENT: #BESENTLearn More - https://www.sentventures.com?utm_source=youtube&utm_medium=podcast_show_notes&utm_campaign=btb-podcast&utm_content=evergreen-learnmoreJoin us for SENT Summit 2026 in Denver, CO - https://www.sentventures.com/sentsummit2026?utm_source=youtube&utm_medium=podcast_show_notes&utm_campaign=summit-2026&utm_content=evergreen-summit______________________► SUBSCRIBE TO BREAKING THE BARRIERiTunes - https://podcasts.apple.com/us/podcast/breaking-the-barrier/id1886035329Spotify - https://open.spotify.com/show/1k5gtLQcde9ihmOjpVhYnD/?utm_source=youtube&utm_medium=podcast_show_notes&utm_campaign=btb-podcast&utm_content=evergreen-spotify______________________► FOLLOW SENT VENTUREShttps://www.linkedin.com/company/sententrepreneurshttps://www.facebook.com/sentventureshttps://www.instagram.com/sentventureshttps://x.com/SentVentures

Rob Hays sits down with Nick Madden to break down what it takes to lead when everything is on fire. Rob took over as CEO of the publicly traded Ashford Hospitality Trust in April 2020 — and within a weekend furloughed 93% of nearly 13,000 associates, ran 700-room hotels with three people, watched revenue fall almost 100% in two months, and defaulted on $4.5B of mortgages across roughly 130 hotels. His father's response: "welcome to your abyss." What he did next is the point: Rob kept the company out of bankruptcy, worked his way through the debt, and led it for five more years before stepping away on his own terms — proof that the principles in this conversation actually hold up under fire.

For Catholic business owners, Rob gets practical: the daily-to-quarterly planning cadence that kept him sane, why "all you can control are your inputs," the quality of attention as a near-virtue, unreasonable hospitality as a real edge, hiring the person instead of the need, and the founder filter he built to decide who to back. He closes on the line that reframes everything — "your priorities are how you spend your time" — and the freedom of seeing the four walls of your office as the material of your sanctity.

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Scott Weeman sits down with Nick Madden to break down the addictions that quietly come with ambition — pride, control, and money — and the honesty it takes to name them. Scott is the Executive Director of Catholic in Recovery, the national nonprofit he built over the last decade around a combination of the 12 steps and the sacraments. He explains why “no one enters recovery on a winning streak,” how the first three steps come down to “I can’t, God can, I oughta let him,” and the red flags that signal a disordered relationship with money — like hiding things from your spouse or your shareholders.

It’s an honest conversation about the solo-hero trap, the limits of doing it all yourself, and why community — not control — is what keeps a founder whole. For Catholic business owners trying to lead without splitting their faith from their work, Scott offers a picture of the undivided life: bring your whole self, surrender what you can’t manage, and build something that outlasts you.

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Scott Weeman's book: "Twelve-Steps-Sacraments-Catholic-Recovery" - https://tinyurl.com/12steps-sacraments

Catholic Recover - https://catholicinrecovery.com/

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