To Grit with Grace: The Podcast

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I hate podcasts — so my marketing coordinator challenged me to launch one. In the process, I realized that what I hated wasn’t the form, it was the rambling, un-curated nature of the chat shows that many view as the definition of “podcast.”

In pared-down, curated episodes, “To Grit with Grace” shares the stories of adversity and perseverance — grit and grace — that have defined and shaped my guests’ lives. Each episode serves as a jolt of inspiration for professionals negotiating this chaotic world. Please join our journey.


Season 2: The Entrepreneur Sessions

Episode 5 — David Edwards

The financial crisis wreaked havoc on David Edwards’s company…and life. As he watched his firm’s assets shrink by 50%, his endocrine system flew into disarray, and he wondered whether he was cut out for this job, this industry, this world.

But through grit, determination, and a ceaseless will to evolve, David rebuilt his firm, one client at a time. By transitioning from investment management to holistic financial planning, David grew his firm’s assets to $500M in the following decade.

David’s intelligence, wit, and resilience are just a few of the qualities I love about him. I’m so glad to have captured his story in the most recent episode of “To Grit, with Grace: The Entrepreneur Sessions.”

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Episode 4 — René Syler

René Syler co-anchored the CBS Morning Show from 2002-2006. Having started out as a local news anchor in Reno, NV, her ascent to the network level was meteoric. So, when she lost the job amid a network shakeup, it was that much harder to take.

René’s story is one of high highs, low lows, setbacks, and transformations. A Black woman, René long faced pressure to conform to conventional beauty standards, which lifted when she transitioned out of network life. Now a one-woman, full-service production company, René’s broadcast life continues — only now, it’s in a way that lets her be her natural self.

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Episode 3 — Erin Ardleigh

Erin came to New York City at 18 years old with only grit and determination to fall back on. Needing to pay for food, housing, school — and fast — Erin learned how to hustle. That hustle would pay off in 2014 when, after a year of traveling the world, Erin started down the entrepreneurial road, one beset by challenges internal and external.

Erin's company, Dynama Insurance, is more successful today than ever. Her story is a must-listen for young entrepreneurs — especially women — hoping to make their mark on the world.

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Episode 2 — Michael O’Brien

In 2011, a freak cycling accident nearly killed Michael O’Brien. Doctors were bearish on Michael’s chances to resume normal function — but Michael felt otherwise.

Michael’s radical injury prompted a radical shift in perspective. It took numerous surgeries to get his body bike-ready; it took deep emotional labor, including a redefinition of his values, to resume life with peace of mind. And when those values didn’t fit with his corporate job (Michael was a VP at a global pharmaceutical company), it meant striking out on his own.

Now a successful entrepreneur twice over, Michael’s story illuminates the full spectrum of the entrepreneurial mindset: from chaos and self-doubt to self-belief and growth.

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Episode 1 — Lisa Weldon

Aged out of her career and reeling from her husband’s financial infidelities, Lisa Weldon found herself 58 years old and in need of a new start. While all of us take recovery one step at a time, Lisa took it one step further, walking every neighborhood in New York City, and building an online following around her blogs and photographs. Simultaneously re-educating herself on modern advertising mechanics, she rejuvenated her career, growing her digital marketing company, Lisa Weldon, Inc.

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Season 1

Episode 9 — Julie Davitz: Impact in Action

Julie Davitz literally grew up in a barn, believing that the best thing in life would be to marry — and marry rich. In spite of her spunk, her tenacity, her independence, Julie took the safe road.

But looks, as we know, are often deceiving. The “safe road” can be anything but. 

In this month’s episode of “To Grit with Grace,” you’ll hear how Julie went from a Cinderella life, to an absolute wreckage, to what sounds to me like sheer hell. But it was hitting bottom that brought her where she is today, running global impact investing company Plus Media Solutions.

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Episode 8 — Lynn Thomas: Permission to Live

There’s no guidebook for grief. It’s an internal battle. People on the outside can provide support, but the real work happens on the inside. It’s hard enough when a relative dies at a ripe old age. But when someone we love is taken from us prematurely, and in the worst possible way, the difficulty multiplies.

Lynn Thomas, this month’s “To Grit with Grace” guest, lived through the unimaginable. Just as she was starting her business and a new romantic relationship, homicide took her sister. As you would imagine — if you can imagine such a thing — this pushed Lynn to the edge of mental stability.

Fortunately, she came from strong Greek immigrant stock, with parents who lifted themselves out of the ghetto, walked away from the mob, and found another way. She learned from them to keep going, even when you’re not where you want to be.

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Episode 7 — Rachelle Fender: Unstoppable

In 2008, the financial crisis brought Rachelle Fender’s career to a halt. But she’d seen devastation before, and she realized that this time, the worst news could actually be the best news — with the right mindset, and with courage. Rachelle found her life’s purpose working with the humanitarian organization appropriately named Unstoppable.

In my early days as a wealth advisor, I believed, like so many people, that more was more. That somehow, a number in a bank account would make my clients happy, and my job was to help them amass the most money possible. 

I learned quickly that nothing could be further from the truth. I redefined my job to help my clients find purpose and passion: to have enough, and to find a way — as Rachelle did — to do what they were meant to do.

I hope that, in listening to her story, you will be inspired, and you will realize that when your devastation comes, with the right attitude, you too can use it as a springboard to find your own “more.”

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Episode 6 — Justin Breen: No Excuses

Justin Breen, founder of BrEpic, was thrust into entrepreneurship when his career came to a halt. A Chicago journalist, he was told one day that his salary was being cut in half for no particular reason. Over the course of the next several months, he reached out to 5,000 people. The day after he got his fifth client, he resigned, and BrEpic was off to the races.

Justin works with the top .1% of people in the world. He describes himself as barely human, and he has boiled down successful entrepreneurship to four key elements. Listen to this month’s episode of “To Grit with Grace” to find out what they are.

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Episode 5 — Lowman Family: No Success Like Failure

Dustin Lowman wasn’t always my marketing manager. In 2015, he moved to Nashville, Tennessee to turn his passion for songwriting into a career. But things didn’t go completely as planned for the 22-year-old. Struggling in an industry town, Dustin faced trials of confidence and identity he never thought he’d face.

But his parents were behind him every step of the way. In a first for the show, this episode features Dustin, his mom, Diane, and his dad, Donald. Diane and Donald divorced well over a decade ago, but they are united in love for their sons. Their support should be a model for every parental pair whose children dream big.

Songs in this episode:

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Episode 4 — Curt Cronin: Saving the Space for Grace

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When we think about war stories, we tend to think in terms of Saving Private Ryan — heroism in the heat of battle, the willingness to face down death for the sake of our fellow soldiers.

My guest this month, Curt Cronin, calls that “valorous courage.” Curt served as a Navy Seal in both Iraq and Afghanistan. Through some trying times, when the U.S. was conducting combat operations in unfamiliar terrain and against an unfamiliar enemy, Curt realized that “infinitesimal courage” — the courage to have tough conversations — was much more valuable. In Curt’s case, that meant telling his commanding officer what he really thought about his orders, unsure of the outcome, not once, but three times.

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Episode 3 — Leslie Montanile: True Love, Lust, and Lies

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Who do you trust? The older we get, the more is at stake, and the harder trust is to come by. This month's guest, divorce lawyer and newly minted author Leslie Montanile, was burned by one kind of trust: that which she invested in her business partner, Jeff.

Who do you trust? 

The older we get, the more is at stake, and the harder trust is to come by. My guest this month on “To Grit with Grace,” divorce lawyer and newly minted author Leslie Montanile, was burned by one kind of trust: that which she invested in her business partner Jeff. But she was saved by another kind of trust: that which she invested in her husband, Joe.

Leslie just published her memoir, “The Cult of the Black Card: A Divorce Lawyer’s Tale of True Love, Lust, and Lies.” I read it, and I’m pleased to say that I, the Russian judge, loved it. Find it on Amazon, or wherever else you buy your books.

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Episode 2 — Bruce DeBoskey: The Two Sides of the Human Coin

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Bruce DeBoskey was a bearded, camera-toting 21-year-old when he first came face to face with inhumanity. It happened in a remote part of Turkey. Bruce faced a choice that day that would change the course of his life.

Bruce DeBoskey was a bearded, camera-toting 21-year-old when he first came face to face with inhumanity. It happened in a remote part of Turkey. Bruce faced a choice that day that would change the course of his life.

In the second episode of “To Grit with Grace,” hear Bruce discuss how that fateful brush with inhumanity ignited a lifelong devotion to loving humanity — the two sides, he says, of the human coin.

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Episode 1 — Randy Kaufman: Trifecta of Suck

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In the inaugural episode of "To Grit with Grace," host Randy Kaufman tells the story of surviving her "Trifecta of Suck" - the '08 financial crisis, breast cancer, and divorce.

The ’08 financial crisis kicked off what I like to call my “Trifecta of Suck.” Followed closely by a breast cancer diagnosis and a divorce, the 10-year period starting in 2008 was a trial. Survival was made possible only by the support of my friends, and an insistence on grit — a trait I learned from my father.

In episode 1 of my podcast, “To Grit with Grace,” I tell the story of how my charmed life turned harrowing, and how I was able to navigate my darkest days. I invite you to listen, to subscribe, and to support me in my new, scary endeavor. I’ve said it before, I’ll say it again: Podcasting is way out of my comfort zone — but, of course, that means it’s where I need to be.

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