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Best Story Wins - Podcast

Best Story Wins

Welcome to “Best Story Wins,” a podcast for marketing and branding professionals looking to unlock their growth potential. Hosted by Column Five—a B2B marketing agency that specializes in brand and content marketing for SaaS companies—each episode features insightful conversations with industry leaders who are winning customers’ hearts and minds by building world-class brands. 

Tune in to hear expert insights, hard-won lessons, and key strategies to take your own marketing efforts to the next level.

Entrepreneurship Business Careers Marketing
Update frequency
every 9 days
Average duration
43 minutes
Episodes
93
Years Active
2023 - 2025
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How to Turn Customers Into Your Loudest Advocates

How to Turn Customers Into Your Loudest Advocates

With everyone talking about AI, it’s easy to feel like your brand has to shout just to be heard. But sounding like everyone else isn’t the answer, it’s a missed opportunity to connect in a meaningful…
00:45:10  |   Thu 04 Sep 2025
The Marketer’s Guide to Modern Storytelling

The Marketer’s Guide to Modern Storytelling

Maybe it’s not a content problem. Maybe it’s a clarity problem.

With AI-generated posts flooding every channel and SEO playbooks changing by the week, B2B marketers are creating more content than ever…
00:42:46  |   Thu 28 Aug 2025
Building a Brand Like a TV Show

Building a Brand Like a TV Show

Everyone’s chasing AI—but what if the real magic in B2B is a rap video, a meme, and two actors with a camera?

While most brands stick to safe, polished playbooks, Chris Cunningham is building ClickUp’…
00:43:25  |   Thu 21 Aug 2025
From Forgettable to Unstoppable Brand Moves

From Forgettable to Unstoppable Brand Moves

Let’s be real: most B2B brands are stuck on repeat. Same buzzwords, same bland websites, same tired playbooks. And in a sea of sameness, nobody stands out. So how do you make people actually care?

In …
00:54:34  |   Thu 14 Aug 2025
Building Trust in a Noisy World

Building Trust in a Noisy World

We’re creating more content than ever—but at what cost to meaning and connection?

In this episode, Kelly Phillips—VP of Brand Marketing at Faire, and former brand leader at Airbnb, YouTube, and Google…
00:29:13  |   Thu 07 Aug 2025
Why B2B Buyers Crave Cool, Too

Why B2B Buyers Crave Cool, Too

If your brand doesn’t spark a feeling, it’s already forgettable. In a world where every product looks the same, the only thing that truly sells is vibe.

B2B marketing is broken. Everyone’s selling the…
00:50:43  |   Thu 31 Jul 2025
The Quiet Revolution Behind B2B Brand Wins

The Quiet Revolution Behind B2B Brand Wins

Too often, B2B brands chase clicks that don’t lead to real results. The fix? It’s not more ad spend—it’s aligning your systems and strategy.

In this episode, Deanna Adams, Senior Director of Integrate…
00:41:51  |   Thu 24 Jul 2025
Meet the Architect of Docusign’s Bold Rebrand

Meet the Architect of Docusign’s Bold Rebrand

Great brands don’t just evolve—they outgrow their origin stories.

Docusign made the signature famous. Now it’s on a mission to make agreements iconic—and that meant blowing up the brand as the world k…
00:49:32  |   Thu 17 Jul 2025
The Anti-Playbook for Modern Brand Builders

The Anti-Playbook for Modern Brand Builders

If your brand feels more like a dusty whitepaper than a bold statement, you're doing it wrong.

In this episode, we sit down with Emily Anne Epstein, the content lead behind Sigma’s rapid rise. Emily u…
00:24:26  |   Thu 10 Jul 2025
The Unscalable Stuff That Scales

The Unscalable Stuff That Scales

Tech is moving fast. But trust? That’s still built the old-fashioned way.
As AI reshapes how we work, connect, and build, the brands that will win aren’t the ones shouting the loudest—they’re the ones…
00:39:09  |   Thu 03 Jul 2025
Why Trust Is the New Brand Currency

Why Trust Is the New Brand Currency

While many fintechs are focused on surface-level features, Ethan Bloch is building an ambitious, AI-powered financial product from the ground up. 

In this episode, Ethan, Founder of Digit and now Hiro…
00:42:05  |   Thu 26 Jun 2025
Becoming Marketing’s Big Sister

Becoming Marketing’s Big Sister

It’s a tough time to be a marketer. Teams are lean, expectations are high, and AI is everywhere—but automation can only take you so far if your brand voice gets lost in the shuffle. So how do you kee…
00:47:24  |   Thu 19 Jun 2025
Your Brand Doesn’t Need a Makeover

Your Brand Doesn’t Need a Makeover

Brand teams are obsessed with differentiation, but what if distinctiveness is the real power move? And while you're chasing loyalty, your competitors are winning with reach.

In this episode, Matt Mayn…
00:44:50  |   Thu 12 Jun 2025
Why Most GTM Plans Don’t Work

Why Most GTM Plans Don’t Work

Many go-to-market strategies sound good on paper but fall apart in practice. The issue isn’t the lack of talent, but rather the misalignment, timing, or wrong assumptions they’re founded on.

In this e…
00:39:07  |   Thu 05 Jun 2025
Why Most Agencies Are Failing Modern Marketing Teams

Why Most Agencies Are Failing Modern Marketing Teams

The old agency model is broken, and smart brands aren’t waiting around to fix it. Instead, they’re building lean, strategic ecosystems where storytelling, rather than scale, is the engine that propel…
00:37:19  |   Thu 29 May 2025
Marketing’s Next Revolution Is Human First

Marketing’s Next Revolution Is Human First

The brands that move first on human connection build an edge no algorithm can touch. The question is: Will you move fast enough to matter?

In this episode, Allison Stadd of Shipt lays out why brands t…
00:34:22  |   Thu 22 May 2025
Why Most B2B Strategies Are Built on a Broken System

Why Most B2B Strategies Are Built on a Broken System

Most B2B marketers are stuck proving short-term wins. Not because it drives the best results, but because it’s the only story the numbers can tell. Could this be why long-term growth, brand equity, a…
00:40:00  |   Thu 15 May 2025
Can CMOs Take Back Control of Growth?

Can CMOs Take Back Control of Growth?

Marketing leaders are under more pressure than ever, and many are stuck playing defense. With budgets tightening and short-term wins taking priority, how can CMOs reclaim their seat at the table and …
00:41:54  |   Thu 08 May 2025
Trust Is the New Growth Hack w/ Chase Howell

Trust Is the New Growth Hack w/ Chase Howell

Marketers are pumping out more content than ever, yet consumers somehow trust it less than their own data. Impressions are meaningless if you’re not driving impact. 

In this episode, Chase Howell, VP …
00:37:21  |   Thu 01 May 2025
How to Build a Billion-Dollar Story w/Ben Parr

How to Build a Billion-Dollar Story w/Ben Parr

Today, anyone can build an AI product on a weekend. To stand out in the market, you must rely on your story. 

In this episode, we are joined by Ben Parr, co-founder of Octane AI and Theory Forge Ventu…
00:53:03  |   Thu 24 Apr 2025
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