The Corporate Couch: Work Stories I Only Tell My Friends

George Brooks (bio below) built Crema almost by accident.

Then, 18 years later, he did something that may have been even harder:

He left it for two months.

Completely.

No email. No checking the pipeline. No “just one quick question” from the founder.

And when George returned from his sabbatical, the company was doing just fine.

Actually, better than fine.

That created a much bigger question:

If the company can thrive without you, who should you be when you come back?

George’s path to entrepreneurship was hardly textbook. He left college, taught himself design, worked a job he hated to support his wife through nursing school, and eventually started freelancing largely because he needed to stay close to his premature daughter, who spent the first seven months of her life in the hospital.

Then came one of my favorite startup stories.

A potential client asked George to propose a redesign of a massive healthcare website. He did some back-of-the-napkin math, slid a proposal across the table for $400,000, and they said yes.

George’s reaction was basically:

Excellent.

Followed immediately by:

Well, shit. Now I actually have to do this.

That project helped turn freelancing into Crema and eventually a company that grew to around 60 people.

George and I talk about building a culture where people can do the best work of their lives, why great leaders should destroy bottlenecks instead of becoming one, how sabbaticals can expose weaknesses in an organization, and why being great at reacting to everything may not actually mean you’re leading effectively.

We also get into AI, human-centered technology, curiosity, “humble confidence,” sleep, rest, and George’s wonderfully counterintuitive advice for young professionals:

Ignorance can be a superpower.

Ask dumb questions.

Because terrible work eventually becomes better work.

This is a conversation about entrepreneurship, culture, leadership, family, rest, reinvention, and the strange moment when a founder realizes one of the greatest signs of success may be that everything doesn’t fall apart when he leaves.

About George: George Brooks is driven by bringing together creative and innovative teams to do the best work of their lives, especially in the era of AI. As CEO of Crema, he stands by the idea that he's in the business of people. His passion for people has led to the sought-after environment inside Crema. 

Crema has served brands like Adidas and H&R Block, top global consultancies, global private equity firms, and cybersecurity providers from around the world.   Currently, George is the co-host and facilitator of the People of Product podcast. He's often found having a cup of coffee with other business leaders who are trying to navigate and adapt in an ever-changing world. 

Steve Jorgenson (see bio below) has had an interesting career.

Law school. An MBA. Government contracts. Staffing and recruiting. Entrepreneurship. Hockey. Rugby. Remote work around the world.

And more than a few bosses who provided excellent examples of how not to lead.

In this conversation, Jeff talks with Steve about growing up outside Chicago, being a spectacularly unenthusiastic high school student, eventually earning both a JD and MBA, and navigating a career filled with difficult managers, big responsibilities, entrepreneurial swings, and a few hard-earned lessons.

Steve shares what it was like managing a $200 million government contract in his twenties, building trust with an employee who initially wanted nothing to do with him, and repeatedly finding himself in workplaces where truth-telling and new ideas were not always welcomed.

He also talks about launching his first company, learning some painful lessons when business partners betrayed his trust, and why those experiences helped shape his newest venture, Poach Prevent, a company designed to help businesses protect themselves from having recruiting partners poach the very employees they are being paid to help hire.

Along the way, Steve explains why the best boss of his career earned his trust by giving him room to do his job, why managers should be resources rather than roadblocks, and why great leaders give credit away instead of hoarding it like leftover Halloween candy.

This is a conversation about bad bosses, good leadership, entrepreneurship, trust, resilience, remote work, career reinvention, and what happens when you finally realize work does not have to feel miserable.

And yes, we also cover rugby in Ireland, hockey dreams, hip replacement at 35, working abroad with your spouse for months at a time, dog summer camp, signing a contract with the NHL, and canceling a $600 wing-walking adventure because apparently standing on top of an airplane without doing barrel rolls was not exciting enough.

About Steve: Steve Jorgenson is the founder of Poach Prevent, a first-of-its-kind compliance auditing tool designed to bring more transparency to non-solicit agreements between external recruiters and their clients. He is also the Global Director of Legal Operations and Data Privacy Officer at The Planet Group, with deep experience across recruiting, staffing, contracts, compliance, and entrepreneurship.

Diankha Linear’s career (see bio below) did not exactly begin with a polished five-year plan.

It started with a red hope chest, a flight from Seattle to Washington, D.C., and the discovery that she had forgotten to apply for housing and complete the FAFSA.

So naturally, she joined the Army.

In this episode, Jeff talks with Diankha about a remarkable career that moved from humble beginnings in West Seattle to military service, airborne school, law school at the University of Pennsylvania, big law, in-house leadership, tech startups, the C-suite, CEO roles, and major board leadership.

Diankha shares how school became her haven, why fairness and justice pulled her toward the law, and how the Army transformed from “temporary college funding plan” into one of the most important chapters of her life.

She also talks about becoming a JAG officer, learning logistics and leadership, making the jump from lawyer to operator, and discovering that she did not just want to advise decision-makers. She wanted to be in the room where the decisions were made.

Jeff and Diankha also dig into Nordstrom’s culture, Convoy’s startup intensity, board leadership, risk in the age of AI and cybersecurity, and her newest venture, Tribute, a purpose-driven elder care concept with what she calls “Golden Girls energy.”

This is a conversation about reinvention, ambition, service, leadership, curiosity, judgment, resilience, and what happens when someone refuses to stay in just one lane.

And yes, we also cover driving ranges, physics rabbit holes, Audible badges, blackberry soup, Kmart fishing poles, Thurgood Marshall, LinkedIn Easy Apply, the Nordstrom employee discount, and why leading people with appreciation and respect is not optional unless you enjoy being quietly sabotaged.

About Diankha: Diankha Linear is a senior executive, operator, and board director with more than 25 years of experience leading across highly regulated technology, logistics, retail, and healthcare organizations. She currently serves on the Board of Directors and as Risk Committee Chair for Lumen Technologies, Board Chair for Swedish Health Services, and Chairperson of Seattle Hospitality Group.​ 

Milford “Beags” Beagle (bio below) has spent his life getting over hurdles.

Sometimes literally.

Before he became a senior U.S. Army leader with a 35-year career, Beags was a kid from small-town South Carolina who admired his truck-driving father, played in the woods, broke his mom’s chairs practicing hurdle technique, and became a state champion hurdler.

That combination of blue-collar grit, athletic discipline, and comfort with hard things eventually led him into the Army, where he discovered a new kind of team.

In this episode, Jeff talks with Beags about what it means to wear “the cloth of our nation,” how his military career shaped his leadership philosophy, and why the transition from military service to the private sector is not about leaving leadership behind. It is about translating it.

Beags shares stories from his first days as a young platoon leader, when he was suddenly responsible for more than 30 soldiers before he was even old enough to legally drink. He also reflects on leading at scale, including the challenge of influencing thousands of people across multiple layers of an organization.

The conversation also covers his powerful Fort Jackson story, where Beags commanded the same post where his great-grandfather trained during World War I, exactly 100 years later. It is a remarkable full-circle moment about history, progress, service, and legacy.

Jeff and Beags also talk about truth tellers, the danger of leaders getting trapped in a “cone of silence,” why feedback is the breakfast of champions, and why great leaders should be data-informed, not data-driven.

This is a conversation about service, humility, uncertainty, leadership, reinvention, and why the best leaders keep moving even when the map runs out.

And yes, we also cover 18-wheelers, “steel and sex appeal,” broken living room chairs, getting voted off the island and finding your way back, “how to handle me” documents, climate as the front door to culture, and why you lead people but manage systems and processes.

About Beags: Milford H. “Beags” Beagle Jr. is a retired U.S. Army Lieutenant General, leadership advisor, and organizational strategist with more than 35 years of experience leading transformation inside some of the nation’s largest and most complex institutions.​ 

As the former Commanding General of the U.S. Army Combined Arms Center and Fort Leavenworth, Beags led the Army’s professional military education, leader development, doctrine, and training integration enterprise, influencing more than 200,000 learners annually and modernization efforts impacting more than 1.5 million personnel worldwide.

DJ DiDonna (see bio below) believes time off can change your life.

Not “check your email from a beach chair” time off.

Real time off.

In this conversation, Jeff talks with DJ about his new book, Big Time Off: The Transformative Power of Sabbaticals and How to Take One, and why sabbaticals can be far more than an extended vacation.

DJ’s own sabbatical came after building what looked like a dream career. He co-founded a mission-driven company, lived and worked around the world, and was doing meaningful work that helped expand access to credit in emerging markets. From the outside, it looked like success. From the inside, he was burned out.

So DJ stepped away. He walked a 900-mile pilgrimage in Japan, spent time caring for his mother, helped family and friends, wrote postcards, picked up music again, and started to understand what it means to feel human again.

Jeff and DJ talk about functional workaholism, why vacations are not the same as sabbaticals, how work becomes identity, why people often wait for a crisis before taking real time off, and how companies could use sabbaticals as a serious tool for retention, creativity, leadership development, and human sustainability.

This is a conversation about burnout, ambition, identity, family, creativity, rest, and the radical idea that maybe we were not designed to be productivity appliances with LinkedIn profiles.

And yes, we also cover Notre Dame, karaoke theory, A-ha’s “Take On Me,” Angie's List, Japan, ukulele songwriting, Pebble Beach, and why your retirement bucket list might deserve a few items moved closer to today.

About DJ: DJ DiDonna is a senior lecturer of business administration at Harvard Business School, where he teaches MBA courses on entrepreneurship and building meaningful professional and personal lives. He has spent his career translating social science research into real-world tools for positive change.​ In 2019, DiDonna founded The Sabbatical Project to define, explore, and research the role of sabbaticals in modern life. He has helped organizations around the world—from nonprofits to Fortune 50 companies—design and implement sabbatical policies.

His work has been featured in The Atlantic, Harvard Business Review, Time, Fast Company, The Wall Street Journal, and The New York Times.

Jessica Grossmeier (see bio below) has spent more than 25 years helping organizations understand what it really takes for people to thrive at work.

And no, it is not just a fitness challenge, a meditation app, and a sad banana in the break room.

In this episode, Jeff talks with Jessica about workplace well-being, burnout, human-centered organizations, and the deeper role that meaning, connection, purpose, and spirituality play in how people experience their work.

Jessica grew up in Chippewa Falls, Wisconsin, home of Leinenkugel’s beer, competitive diving, lots of reading, and, apparently, the possibility of a beer-and-mustard tour across Wisconsin. Her early love of movement, health, and learning eventually led her into corporate wellness, where her first job placed her inside the UAW Ford Twin Cities Assembly Plant.

That experience taught her an important lesson: never assume you know someone’s full story just because of their job title, uniform, shift, or rough edges.

From there, Jessica built a career as a practitioner, researcher, author, advisor, and speaker. But after years of studying workplace well-being, she experienced burnout herself and realized something important: burnout is not just an individual problem. It is often a system problem.

Jessica also shares the story of her 2021 sabbatical, the restlessness that led her to take it, and how that year helped her explore workplace spirituality: the practices that help people connect more deeply to themselves, to others, and to something bigger than themselves.

This is a conversation about burnout, purpose, leadership, sabbaticals, faith, joy spotting, human-centered work, and why how you do your job matters just as much as what you do.

And yes, we also cover introverted speakers, Stephen King in fifth grade, The Godfather, springboard diving, water aerobics, Polish-free Wisconsin beer tourism, corporate layoffs, and why “your colleagues think you’re prickly” may be one of the more useful performance reviews a high achiever can receive.

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About Jessica: Jessica Grossmeier, PhD, MPH is an organizational strategist, researcher, and author of two books on workplace well-being and human thriving. For more than 30 years she has studied what drives sustainable human performance — and helped organizations demonstrate the value of investing in the conditions that make it possible. She helps leaders identify those conditions and design them into new ways of working, for the benefit of people and the organization. She is a Senior Fellow at the Health

Dr. Matthew Naylor (see bio below) grew up in Melbourne, Australia, making billy carts from rubber factory wheels and learning early lessons about independence, possibility, and the common good.

Today, he is the President and CEO of the National WWI Museum and Memorial, one of Kansas City’s most iconic institutions and, in Matthew’s words, “Kansas City’s front porch.”

In this episode, Jeff talks with Matthew about his Australian childhood, his father’s World War II service, his own early experience as an exchange student in the United States, and the leadership journey that eventually brought him to Kansas City.

Matthew shares powerful stories about purpose, stewardship, servant leadership, and why the Museum and Memorial is much more than a place to remember the past. It is a gathering place, a civic symbol, and a beacon for democracy.

They also talk about Matthew’s deeply moving connection to Holocaust survivor Sonia Warshawski, the leadership lesson that changed how he thinks about reality versus the preferred future, and why he believes even straight mowing lines and picking up tiny pieces of trash matter when you are caring for sacred ground.

This conversation comes during the Museum and Memorial’s centennial year, leading up to the Sept. 21 Centennial Gala at the Kauffman Center for the Performing Arts and the debut of "Liberty’s Beacon", a lighting and video installation designed to illuminate the Memorial in a way Kansas City has never seen before.

This is a conversation about leadership, memory, democracy, service, storytelling, and what it means to steward something bigger than yourself.

And yes, we also cover Australian go-karts, tattoos in World War I, free speech on the lawn, Kansas City’s best view, and why a CEO should never be too important to pick up a piece of paper.

About Matt: Dr. Matthew Naylor is the President and CEO of the National WWI Museum and Memorial in Kansas City, Missouri. Since beginning his tenure in 2013, Matthew has helped lead the Museum and Memorial through a period of extraordinary growth, including record-setting attendance, philanthropy, educational engagement, community events, digital learning, and national visibility.​ 

Under his leadership, the Museum and Memorial has continued to expand its role as one of Kansas City’s most meaningful gathering places, hosting major civic events, championship parades, the 2023 NFL Draft, and the city’s annual Independence Day celebration.​ Matthew brings more than 30 years of nonprofit leadership experience and has been recognized as Nonprofit PRO’s “Executive of the Year,” one of Ingram’s “50 Missourians You Should Know,” and a recipient of the Native Sons and Daughters of Kansas City’s “Outstanding Kansas Citizen Award.”

Britney Valas (see bio below) has lived enough chapters for three memoirs, two Netflix docuseries, and possibly one CrossFit workout no one should attempt without medical supervision.

In this episode, Jeff talks with Britney about resilience, reinvention, faith, family, leadership, and what happens when life hands you the business-owner version of a flaming casserole.

Britney’s path started with a seven-year plan she created as a teenager to become a pharmaceutical sales rep. She worked at Kmart, became a certified pharmacy technician at 17, graduated early, thrived at Enterprise, and eventually landed the job she had been chasing at Bristol Myers Squibb. Then she realized the dream job did not deliver the fulfillment she expected.

From there, her story moves through stay-at-home motherhood, homeschooling five kids, triathlons, restaurant ownership, COVID, divorce, franchise chaos, bankruptcy, rebuilding, and the creation of S​h​aw Enterprises, Empower ​Y​ou, and her                  T​RIGGERZ program.

This is a conversation about falling apart, getting back up, finding purpose in every role, and turning hard-earned lessons into tools that help other people heal, grow, and lead.

And yes, we also cover CrossFit, five kids, margaritas to-go, beetles crawling out of restaurant tables, a nonprofit grant, juvenile detention work, and why sometimes the worst season of your life becomes the raw material for your next calling.

About Britney: Britney Valas is the Founder and President of Empower You, Inc. and the creator of the TRIGGERZ® Transformation System, a practical framework that turns emotional storms into structured pathways for nervous system regulation, emotional healing, and neural pathway growth. As founder of Shaw Enterprises, she leads a transformation consulting firm that serves companies and organizations with fractional strategic leadership and corporate wellness solutions, carrying the same tools from youth and adults in crisis to leaders in the boardroom.

Shari Noonan (see bio below) has built a career by stepping into complexity and figuring out how to move it forward.

In this episode, Jeff talks with Shari, CEO and co-founder of Rialto Markets, about a career that started with summers at Lake of the Ozarks, waiting tables, reading through the local library, and becoming an accounting major partly out of spite after a professor suggested she switch to communications. Naturally, she stuck with accounting. Spite, apparently, can be a surprisingly effective academic advisor.

Shari’s path took her from KPMG to consulting, from the early days of electronic trading to Goldman Sachs, Deutsche Bank, and eventually into the startup world with Rialto Markets. Along the way, she worked through major shifts in capital markets, post-merger integration, corporate complexity, thousands of systems, regulatory challenges, fundraising, litigation, and the identity shift that comes with leaving a big-company platform behind.

We talk about:

• Growing up in Kansas City and spending summers at Lake of the Ozarks

This is a conversation about reinvention, resilience, market disruption, trusting your gut, and learning how to move through chaos without dragging a steamer trunk full of old corporate identity behind you.

And yes, we also cover random Polish landladies, TV taxes, microfiche misery, eight bosses, 2,500 systems, dine-and-dash trauma, and why sometimes the worst job you ever had is useful because at least you can check it off the list.

About Shari: Shari Noonan is the Co-Founder and CEO of Rialto Markets, a FINRA-registered broker-dealer and SEC-registered Alternative Trading System built to bring institutional-grade infrastructure to private capital markets.

With more than 25 years of experience at Goldman Sachs, Deutsche Bank, and Instinet, Shari helped shape the electronification of public equity markets. Today, she is applying that same innovation mindset to private markets, helping expand access to capital through regulated platforms for primary issuance, secondary trading, transfer agency, and digital securities.

Under Shari’s leadership, Rialto has become a pioneer in the tokenization of real-world assets, including music royalties, film rights, and community-owned enterprises. She is also a leading voice on how passionate communities, from fanbases to alumni networks, can become powerful new capital formation channels.

Shari holds a B.S. in Accounting from Marquette University and an M.B.A. from Columbia Business School. She has received multiple industry honors, including the Marquette University College of Business Administration Entrepreneurial Award and the Markets Media Choice Instinet Positive Change Visionary Award.

Anna Redmond’s story starts with a mountain lion in her yard.

Seriously.

Before Jeff and Anna (bio below) get into entrepreneurship, physical security, challenge coins, blockchain, Harvard, venture capital, and leadership, Anna explains how a mountain lion turned her neighborhood into a national news story and trapped her family in the house for hours. Not your typical podcast warm-up.

Anna is the Founder and CEO of Braav, a physical security company trusted by organizations nationwide. She also built AllCoin, a free platform helping military, law enforcement, and first-responder communities digitize, verify, and preserve their challenge coin collections on the blockchain.

Born in Kiev, Ukraine, when it was still part of the Soviet Union, Anna moved to the United States as a child. That early family leap shaped her comfort with risk, curiosity, and building her own path.

In this conversation, Anna shares how she went from Harvard to venture capital, from finance to entrepreneurship, and eventually into private security after realizing many organizations are responsible for keeping people safe without having true security expertise in the room.

We also talk about the history and meaning of challenge coins, why the stories behind them matter, and how AllCoin is helping preserve those stories for veterans, first responders, families, and future generations.

This is a conversation about risk, reinvention, service, security, storytelling, and building something because you cannot stop thinking, “There has to be a better way.”

And yes, we also cover juggling, lemonade stand inflation, bringing food to meetings, presidential coins, Navy SEAL coins, and a mountain lion that clearly did not care about Anna’s calendar.

About Anna: Anna Redmond is the Founder and CEO of Braav, a physical security company trusted by organizations nationwide. A Harvard AB/AM and former venture capitalist at Rustic Canyon Partners, Anna has been featured in Forbes, Security Journal Americas, US News & World Report, and TechNewsWorld. She also built AllCoin, a free platform where military, law enforcement, and first responder communities can digitize, verify, and preserve their challenge coin collections on the blockchain.