The One Away Show

Derek Coburn has made a lot of decisions in his life. Good ones. Bad ones. But ask him which one changed everything — and the answer comes without hesitation.

Marrying Melanie.

Not a business deal. Not a career pivot. Not a bold financial bet. The person he chose to build his life with. And 17 years, two kids, and a thriving wealth management practice later — he's more convinced than ever that who you marry is the most important decision you'll ever make.

In this episode, Derek gets refreshingly honest about what it actually takes to build a great marriage, a great career, and a great life — at the same time.

We get into:

• Why "happy wife, happy life" is some of the worst advice ever given

• Starting therapy while engaged — and never stopping

• The privilege nobody talks about: waking up next to someone you love

• The Tale of Two Tonys — and why you probably only need to save 1% to retire well

• The $50,000 moment every parent is taking for granted right now

• Why he restructured his entire day around being available when his kids want him

• What it means to be in the "regret minimization business"

• Why he's not selling anything — and why that makes everything he says more worth hearing

If you've ever wondered what it looks like to actually design a life you don't want to escape from — this one's for you.

In February 2020, Willie Litvack had his biggest month ever. Squadup — the self-service ticketing platform he'd spent six years building brick by brick — had just crossed $400K in monthly revenue. The business was profitable. The momentum was real.

Then the phone rang.

Within nine days, revenue went from $400K to zero. Willie had to furlough 17 people on a call with a lawyer billing $700 an hour — a lawyer he couldn't afford. And he had to figure out how to keep the lights on with almost nothing in the bank.

What he did next is a masterclass in leading through chaos.

In this episode, Willie shares:

• How he built Squadup from zero to $5M ARR without VC money — and why that made COVID hit harder

• The emotional reality of letting 17 people go in a single day and what it took to carry that

• Why the CEO's job is to be a shield — and what happens when the shield breaks

• How they used the downtime to rebuild the product and came out stronger on the other side

• The eventual exit and what it actually felt like

• Why he started Press On Ventures — and what "press on" means to him personally

• The three I's framework he uses to evaluate every founder: Integrity, Intensity, Intelligence

• The role his wife Madeline played in making all of it possible

If you've ever had to hold it together when everything was falling apart — this one's for you.

Shiv Gettu didn't find his big idea in a boardroom. He found it in a basement, 45 minutes deep in meditation.

That moment of stillness sparked a decision that would define the next decade of his life — convincing his co-founder Kendrick to quit his job, become a leasing agent for free, and spend nine months learning the real estate industry from the ground up. The hustle earned them their first $500K check. And then COVID wiped it all out.

From burning $100K a month with no travelers and a mountain of leases, Shiv and his team did what most founders can't — they pivoted fast, built an AI leasing agent from scratch, and turned a crisis into the foundation of Zuma.

In this episode, we get into:

• The mentor who meditated, invested, and changed everything

• Why the best company decisions come from silence, not spreadsheets

• How COVID destroyed their business — and forced them to build a better one

• The RV tour: driving across the country with a podcast studio to get close to customers

• Why relationship first, transaction second is the only enterprise sales strategy that works

• Naval's framework for picking the right problem — and why most founders skip this step

• Paul Graham's essay on doing great work and what it actually takes

If you've ever made a leap that looked crazy from the outside but felt completely right on the inside — this one's for you.

Justin Gelinas hated school. Not because he wasn't smart, because the box was too small.

Then a teacher named Laurie took him on a field trip to a design studio in Burlington, Vermont. Tribe Called Quest was playing. There was a half pipe in the basement. Twenty-somethings were designing brand strategy for Burton Snowboards on an open floor plan. And Justin walked out knowing exactly what he wanted to build.

That one field trip set off a lifelong pursuit of the unconventional, from DJing at 13, to building creative technology companies, to now founding TAHO: middleware that's making AI infrastructure faster, cheaper, and more efficient at a moment when the world desperately needs it.

In this episode, we get into:

• Why the cookie cutter school path never fit — and what happened when he found his version of it

• How music and business are more alike than anyone admits

• The role his entrepreneurial mom played in shaping how he saw work

• Building and selling a company right before the AI wave hit

• Why the infrastructure powering AI today was built for a world that no longer exists

• What TAHO is doing to solve the compute crisis — and why data centers running at "full capacity" are actually only at 50%

• His three pillars for every product decision: faster, more affordable, universally adaptable

If you've ever known in your gut that the conventional path wasn't yours — this one will hit.

Rajat Suri was supposed to be a doctor. That was the plan. The Indian dream, as he puts it. And he was on track.

Then he walked into a three-hour lecture by a professor named Larry Smith at the University of Waterloo — and everything changed.

One idea cracked him open: that a single individual could change the sweep of history. Not just help one person at a time, but reshape how millions of people live their daily lives. That realization sent him down a path that led to co-founding Zimride (which became Lyft), building Presto — the AI-powered drive-thru technology used in major restaurant chains — and now Tribe, a group chat platform built to bring back the intimacy of real human connection in the age of AI.

In this episode, Rajat shares:

• The one lecture that redirected his entire life path

• Why he applied to MIT knowing he was going to drop out

• How Drew Houston of Dropbox pushed him toward Silicon Valley

• The problem with WhatsApp, Reddit, Discord, and every other platform — and why Tribe is different

• What it actually takes to build a community that lasts

• Why human conversation skills are going to be the most valuable skills in the AI age

• How he thinks about impact, wealth, and giving it all back

If you've ever felt like you were built for something bigger — this one's for you.

Guest: Rajat Suri, Founder of Tribe & Presto, Co-founder of Lyft

What happens when the world sees a version of you that you haven't fully become yet?

In 2016, Jason Feifer became Editor in Chief of Entrepreneur Magazine. He thought it was just another media job. Then the podcast invitations started coming in — and with them, a realization that would change everything. People expected him to be an authority. And he didn't feel like one.

Instead of shrinking from that gap, he decided to close it.

In this episode, Jason shares the one moment that shifted him from media guy to one of the most recognized voices in entrepreneurship — and the decade-long compounding that followed.

We get into:

• Why the title "Editor in Chief" was actually a forcing function for growth

• The difference between old opportunity and new opportunity — and how to spot the fork

• How he built a personal brand that became more valuable than the job itself

• Why being "just a media guy" was a path to extinction — and what he did about it

• The personal brand stock exchange (yes, we coined that)

• What a slowdown in speaking bookings taught him about necessity and opportunity

• Where he's placing his bets in 2026

If you've ever felt the gap between who you are and who you're expected to be — this one will hit home.

What do a small village in Donegal and a train car in the middle of Siberia have in common? According to Ciara, Executive Producer at Web Summit — everything.

In this episode, Ciara shares her One Away moment: the realization that her love for global community was just a bigger version of what she learned growing up in rural Ireland. From summers crossing Europe in a campervan with her mom, to studying Russian in Moscow, to programming stages for 70,000 people in Lisbon — her life has been one long exercise in finding the common thread between people who seem worlds apart.

We get into:

• Growing up as an "outsider" in a tight-knit Irish village and what it taught her about belonging

• How learning Russian and Spanish unlocked a philosophy, not just a skill

• The art of programming conversations that challenge people without alienating them

• What Web Summit does to create meaningful connection at massive scale

• Why she's most excited about BRICS economies and what the world is getting wrong about China

• The Vancouver event and what makes it unlike anything Web Summit has done before

If you believe we have more in common than we have differences — this one's for you.

🎙️ Guest: Ciara, Executive Producer at Web Summit 📍 Web Summit Vancouver: websummit.com

The One Away Show explores the one moment, person, or decision that changed everything.

On this episode of The One Away Show, we sit down with Andrew Sherman — attorney, educator, and author of 26 books — who has spent nearly four decades advising entrepreneurs with rare empathy, strategic clarity, and calm. Andrew shares the early hardships that shaped him, the first venture that taught him what founders carry, and the inflection point that changed his path: choosing to support entrepreneurs rather than become one. We talk about the long-game mindset, why purpose is something you owe to yourself and the people you love, and how "mutuality" is the foundation of every meaningful relationship. Andrew also reflects on writing his first book at 26, the discipline of consistency, and the moments — like testifying before Congress or helping unlock hidden enterprise value — that reminded him he was on the right road. This is a conversation about perspective, resilience, and the kind of wisdom that only comes from time.

Sometimes a knock on the door isn't literal – it's the moment you realize the life you've built needs to be rethought.

In this episode, Andy Klump shares how nearly two decades in China – from selling Dell computers under intense pressure to helping scale one of the world's largest solar manufacturers – shaped his career, identity, and leadership. He reflects on the moments that tested his resolve, including navigating cultural barriers, building trust across borders, and confronting unexpected scrutiny that signaled the end of a defining chapter.

Andy also walks through founding Clean Energy Associates during the 2008 financial crisis, growing it into a global, values-driven firm, and eventually stepping back to prioritize family, health, and clarity. It's a conversation about resilience, humility, and knowing when it's time to pause – because sometimes the biggest growth comes from reconsidering everything you thought was next.

Some patterns shape us. Others ask to be broken.

In this episode, Angela Wimmer shares the defining moments that helped her understand the difference. Growing up in a home marked by instability, she learned early on how to think for herself – even when it meant standing alone. With the steady influence of her grandparents, she found curiosity, confidence, and the belief that her voice mattered, long before she had the words for it.

Angela opens up about how those early experiences shaped the life she chose to build as an adult: a grounded marriage, intentional parenting, and a career spent helping others find clarity and direction across politics, higher education, and investing. Her story is a powerful reminder that breaking inherited patterns isn't a single decision – it's a series of choices to live differently than what you came from.

If you've ever questioned the narratives you grew up with, or worked to build a life beyond them, this conversation will stay with you.