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The Entrepreneur Sessions: 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.

Podcast, Featured PostsRandy KaufmanApril 12, 2022entrepreneur, business, perseverance, womenComment

Grit with Guests: Growing Wings

Grit with Guests: Growing Wings

In the early 20th century, experiments on parasites revealed that when rose bushes infested with them died, the parasites, previously wingless, would grow wings. Once their source of food was dead, a metamorphosis took place, and they grew wings to help them avoid starvation and support them in finding a new source of food.

Family Matters, Growth, Grit with GuestsMindy StrichMarch 21, 2022grit, grace, wings, change Comment

The Entrepreneur Sessions: 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.

PodcastRandy KaufmanMarch 7, 2022podcast, entrepreneur, grit, grace, perseveranceComment

False Gods: “Magical Trusts Will Teach My Children Well”

False Gods: “Magical Trusts Will Teach My Children Well”

As a wealth advisor, I often have conversations with parents concerned about spoiling their children. “I just don’t want my kid to turn into Paris Hilton,” they tell me, using “Hilton” as a byword for all that can go wrong with a privileged upbringing. Their children are often either adolescents or young adults, displaying some Hilton-esque warning signs.

Family Matters, False GodsRandy KaufmanFebruary 19, 2022grit, grace, children, moneyComment

The Entrepreneur Sessions: 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.

Podcast, Featured PostsRandy KaufmanFebruary 7, 2022podcast, entrepreneur, pivot, mid-career, reinventionComment

Great Escapes — or, Why I Sail

Great Escapes — or, Why I Sail

In the depths of winter, with lakes frozen and boats shrink-wrapped, I ask myself why I love to sail. My attempt to answer that question follows. Spoiler alert — it’s not about the warm weather, and it’s not about sailing’s similarities to the high seas of investing.

The Examined LifeRandy KaufmanJanuary 28, 2022sailing, adventure, grit, grace Comment

Grit with Guests: The Louvre or Not?

Grit with Guests: The Louvre or Not?

Excuse me, but I’m going to be a bit sacrilegious for a moment. I’m walking the 1st Arrondissement in Paris today, the neighborhood that houses the Louvre, the grand sentinel of the world’s art treasures.

But I doubt I’ll even step foot in it. I have great respect for the works of art and the masters who created it, but quite honestly, I’m bored by most of it. I’d much rather see what’s outside its walls, the graffiti around this City of Lights.

Grit with Guests, Featured PostsLisa WeldonDecember 20, 2021louvre, art, museum, graffiti, street artComment

Randy's Recs: Top 10 Books of 2021

Randy's Recs: Top 10 Books of 2021

As has become a holiday tradition, I’ve compiled my top 10 books of 2021. They cover a wide spectrum — novels, graphic novels, pandemic nonfiction, rock star memoir — and they all shimmer with one (or more) of my four G’s: Grit, Grace, Growth, and Gratitude. As my gift to you, here are 10 books that, if you need a good read, won’t let you down. As always, I welcome dialogue — what would be on your top 10 list?

Reading LessonsRandy KaufmanDecember 13, 2021Comment

That's A(nother) Wrap! Writing My Way Through 2021

That's A(nother) Wrap! Writing My Way Through 2021

As America started its painful process of breaking up with its tyrannical commander-in-Cheeto, I experienced my own little breakup. A global pandemic ravished the world, and I left corporate America. I was tired of not being able to say what I wanted, when I wanted, how I wanted. I loved my work, and I loved my clients, but after 40 years in corporate environments, it was time to spread my wings — and to raise my voice.

Featured Posts, Reading LessonsRandy KaufmanNovember 29, 2021Writing, 2021, articles, processing, politicsComment

That's a Wrap: Looking Back on Season 1 of "To Grit, with Grace"

That's a Wrap: Looking Back on Season 1 of "To Grit, with Grace"

In just nine episodes, we spanned much territory: Navy Seal operations in Iraq, backpacking in Turkey, folk singing in Nashville, financial crisis all across the country, and more. We talked to people who grew up with nothing and people who grew up with everything. In short, we talked to humanity — the many ways it can manifest, the common lessons that make our days enjoyable.

Podcast, Featured PostsRandy KaufmanNovember 8, 2021podcast, retrospective, grit, perseverance, storytellingComment

Grit with Guests: Charity “Grand Bargain” Strained by Religious Nonprofit Tax Exemption

Grit with Guests: Charity “Grand Bargain” Strained by Religious Nonprofit Tax Exemption

We all pay more for the essential services provided by local, state and federal governments because tax revenue is lost by the special tax treatment afforded religious nonprofits. It’s time to ask some very important and difficult questions.

Give Smart, Grit with Guests, Featured PostsBruce DeBoskeyOctober 25, 2021charity, religion, exemption, tax, revenue, philanthropyComment

Comfortably Numb: The Lost Art of Doing Nothing

Comfortably Numb: The Lost Art of Doing Nothing

To live in the modern world is to be addicted to activity. Lost in the torrent is a state of being as healthy as working out: Doing Nothing.

Mind Games, Featured PostsRandy KaufmanOctober 12, 2021sloth, doing nothing, activity, screen, screen time Comment

To Grit with Grace, Episode 9 — Julie Davitz: Impact in Action

To Grit with Grace, 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.

Featured Posts, PodcastRandy KaufmanOctober 4, 2021impact, podcast, divorce, transformationComment

Randy's Rant — You Do You

Randy's Rant — You Do You

I’ve had it with judgement — people judging others; people judging me. What happened earlier this month in Texas appalled me, and reminded me of many instances of judgment I’ve suffered over the decades. Often, they were thoughtless judgements, thrown out negligently, stinging like barbs.

Randy's Rants, Featured PostsRandy KaufmanSeptember 27, 2021judgment, abortion, texas, law, rant, grit, graceComment

To Grit with Grace, Episode 8 — Lynn Thomas: Permission to Live

To Grit with Grace, 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.

Podcast, Featured PostsRandy KaufmanSeptember 13, 2021podcast, murder, resilience, grief, compassion Comments

From the South of France to the Hudson Valley: Why I Read, and Why I Write

From the South of France to the Hudson Valley: Why I Read, and Why I Write

A lot of money-oriented people don’t see the point in writing. A lot of corporate communications are filled with typos, dry language, and other missed opportunities to generate meaning. I went away from the literary arts for a long time, focusing on my career. But I came back when I desperately needed answers. I’m never leaving again.

Featured Posts, Reading Lessons, The Examined LifeRandy KaufmanSeptember 10, 2021literature, meaning, reflection, valueComment

Grit with Guests — Dustin Lowman: On Year One

Lessons learned from 12 months and 383,628 words of freelance writing: 1. People are Knowable; 2. Technicalities are Learnable; 3. Language is Essential.

Featured Posts, Grit with GuestsDustin LowmanAugust 20, 2021writing, freelance, anniversary, data, lessonsComment

To Grit with Grace, Episode 7 — Rachelle Fender: Unstoppable

To Grit with Grace, 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.

Podcast, Featured PostsRandy KaufmanAugust 2, 2021podcast, philanthropy, humanitarian, perseveranceComment

False Gods — Givin' on a Prayer II: The Myth of “Easy” Family Philanthropy

False Gods — Givin' on a Prayer II: The Myth of “Easy” Family Philanthropy

Is family philanthropy a false god? In my opinion, no — it’s just hard. When it comes to ambitious goals, I believe hard is good, and easy is bad. It’s a good thing, too, as researchers have found that the most durable, profound pleasure comes from activities that require effort.

Give Smart, Featured Posts, False GodsRandy KaufmanJuly 30, 2021family, philanthropy, givingComment

To Grit with Grace, Episode 6 — Justin Breen: No Excuses

To Grit with Grace, Episode 6 — Justin Breen: No Excuses

Justin Breen, founder of BrEpic, was born with a story. He found out he had what it took 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 5000 people. The day after he got his fifth client, he resigned, and his company was off to the races.

Podcast, Featured PostsRandy KaufmanJuly 13, 2021podcast, entrepreneur, justin breen, brepic, storyComment