Return on Reputation

By Justin ObeyBusiness Marketing

Return on Reputation episodes

May 14AI Won't Replace You — But This Skill Gap Will | Mamoon Chowdry | Ep. 13
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Every company says they're using AI. Almost none of them can prove it's working.
Mamoon Chowdry has a front-row seat to that gap. As Director of AI Transformation at GE Healthcare — a company with more FDA-cleared AI medical devices than any other on earth — he spends his days sitting with engineering teams, watching what actually happens when AI lands inside a large organization. Not the announcement. Not the dashboard. The ground truth.
What he's found is both reassuring and urgent: AI isn't coming for your expertise. It's coming for the generic version of it. The people who thrive aren't the ones who use the best tool. They're the ones who bring irreplaceable judgment to whatever tool they use.
In this episode of Return on Reputation, Justin sits down with his neighbor and friend Mamoon Chowdry for one of the most practical and honest conversations about AI and your career you'll find anywhere.
What you'll learn in this episode:
Why 30% of AI success is in the technology and 70% is in the human layer — and what that means for every person using AI at work
The two-question test you can run on your team tomorrow: are you using AI, and can you prove it's working?
The "two jobs" framework: the difference between execution and judgment — and why judgment is the skill of the next 20 years
The engineer story that changed how Mamoon thinks about AI: a woman working with temperature sensor data in maternal infant care who said "I finally feel like I can operate at the level I should have been operating at all along"
Why AI without your expertise produces what Mamoon calls "plausible mediocrity" — and what that means for your career
The two groups inside every company right now — and why both of them are quietly embarrassed about AI
What an agentic operating system actually is and how Mamoon uses one to research, think, and grow as a person — not just a professional
Why learning in public on LinkedIn changed the trajectory of his career — and the direct link between that and trust, reputation, and influence
If you've been wondering whether AI is going to replace you — this episode answers the question honestly, practically, and with real stories from the inside of one of the world's largest healthcare companies.
Follow Return on Reputation on YouTube, Spotify, and Apple Podcasts so you don't miss an episode.
HASHTAGS: #AI #CareerGrowth #ArtificialIntelligence #FutureOfWork #PersonalBrand #AIAtWork #Leadership #GEHealthcare #EnterpriseAI #ReturnOnReputation
TIMESTAMPS:
00:05 Who Is Mamoon Chowdry
03:00 The 30/70 Rule: Why AI Success Is Mostly Human
08:35 The Gap Between What Companies Think AI Will Do and What Actually Happens
11:00 The C-Suite Workshop — Every Hand Up, Then Every Hand Down
16:15 The Engineer Story — Temperature Sensors, Premature Babies, and One Hour
19:05 Execution vs. Judgment — The Two Jobs Every Knowledge Worker Has
23:30 Will AI Replace You? The Honest Answer
25:55 "This Is Why You Are Irreplaceable"
29:25 Tools, Agents, and the Agentic Operating System
32:30 The Research Agent That Works While He Sleeps
39:05 Has Learning in Public Changed His Career?
40:50 The Permission Slip — Two Groups in Every Company, Both Embarrassed
45:33 Rapid Fire
48:18 How to Start From Scratch If You're Feeling Behind
49 min
May 08Why Some Founders Get Backed and Others Don't | Suneel Gupta | Ep. 12
What do you do when the New York Times labels you the face of failure — and your face is literally the first result when someone Googles the word? If you're Suneel Gupta, you use the article as your calling card, spend the next few years interviewing hundreds of the world's most successful people, and write the book that answers the question everyone's afraid to ask: why do some people get backed and others don't?

In this episode of Return on Reputation, Justin sits down with Suneel Gupta — bestselling author of Backable and Everyday Dharma, Harvard faculty member, and founding CEO of RISE (named App of the Year by Apple and later acquired by Amazon) — for a conversation about conviction, reputation, and what it actually takes to get people to take a chance on you.

This one goes deep. Suneel reveals why confidence is the wrong thing to optimize for, why AI makes conviction more valuable than ever, and what the most successful founders he's ever interviewed all have in common. Plus — an exclusive first look at his upcoming third book.

What you'll learn in this episode:
Why the most backable people aren't charismatic — they have conviction, and there's a difference
How to incubate an idea before you pitch it — and why sharing too early is a health hazard for your business
The parking lot moment that changed how Suneel pitched Rise forever — and raised millions
Why AI-generated content is killing reputations, not just building them
The 55/5 principle Suneel uses to sustain energy and performance across a busy career
What Everyday Dharma taught him about the gap between outer success and inner fulfillment
What reputation actually means when you strip away the LinkedIn version of yourself
If you're a founder who's been grinding in private, unsure if you're ready to step forward — this episode is your permission slip.

Follow Return on Reputation on YouTube, Spotify, and Apple Podcasts so you don't miss an episode.

Hashtags: #PersonalBranding #Entrepreneurship #FounderStory #Backable #SuneelGupta #B2BMarketing #AuthorInterview #StartupLife #ConvictionOverCharisma #ReputationBuilding
Timestamps:
00:00 Cold Open
01:10 Who Is Suneel Gupta — The Non-LinkedIn Version
02:40 Storytelling as Dharma
05:15 The Conviction vs. Confidence Shift
08:40 Why New Ideas Need Incubation
10:00 Stop Building Decks — Build Belief First
13:00 The Parking Lot Moment That Changed the Pitch
14:55 Why Your Energy Matters More Than Your Words
17:10 AI Scripts vs. Real Conviction
17:30 The Relationship Between Backable and Everyday Dharma
20:00 Finding Your Gift — The Meaning vs. Purpose of Life
21:00 The 55/5 Principle for Sustained Energy
25:00 What Being Backable Means for Invisible Founders Today
26:10 Why Suneel Doesn't Love Social Media — And What Actually Works
29:10 Outer Success vs. Inner Fulfillment
32:15 Rapid Fire
32:33 Courage Follows Action — His Mother's Ford Story
34:00 The Most Underrated Thing About Conviction
35:05 Twitter 2009 vs. LinkedIn 2026
35:45 The One Thing Successful People Have in Common
36:00 EXCLUSIVE: Suneel's Third Book Revealed — "The Game of Now"
38:05 What Does Reputation Mean to You Today?
41 min
April 30He Owned the Personal Branding Category Before Anyone Else Did | Dan Schawbel | Ep. 11
In 2007, a kid from Bentley University Googled "personal branding" after a boring corporate training class and decided to own the entire category. Today, Dan Schawbel has 170,000+ LinkedIn followers, a newsletter reaching 380,000 professionals, three bestselling books, and a research firm that has interviewed 3.18 million people across 26 countries for companies like Oracle, Deloitte, UKG, and Upwork. He's interviewed Warren Buffett, Natalie Portman, Matthew McConaughey, and Hulk Hogan.

He also built all of it through relentless outreach, zero fear of rejection, and a commitment to starting small and compounding over 20 years.

In this episode of Return on Reputation, Justin sits down with his Bentley classmate and personal branding pioneer Dan Schawbel for a conversation about what it actually takes to build lasting authority and why the window to do it is closing faster than most founders realize.

What you'll learn in this episode:
How Dan went from a corporate training class he hated to owning seven of the top ten search results for "personal branding"
Why visibility creates opportunities — and how one Fast Company article turned him from a nobody at EMC into the person who wrote his own job description
What 3.18 million research interviews and nearly 100 studies have taught him about what companies and employees actually want
Why personal branding is 5,000 times more important today than it was two years ago — and why that number is only going in one direction
The AI productivity paradox: 96% of executives say AI is boosting productivity. Most employees say it's adding to their workload.
Why 60% of LinkedIn content is already AI-generated and what that means for anyone trying to build real authority
What happens when you hire Dan Schawbel — and why your personal brand is actually Authority Capital
If you've been waiting to build your personal brand, this episode makes clear there's no more time to wait.

Follow Return on Reputation on YouTube, Spotify, and Apple Podcasts.

Hashtags: #PersonalBranding #DanSchawbel #FounderStory #AuthorityBuilding #LinkedInGrowth #B2BMarketing #ThoughtLeadership #AIWorkplace #ContentStrategy #ReturnOnReputation

Timestamps:
00:11 Personal Branding Origins & Social Media Early Days
03:57 Standing Out at EMC & Tom Peters Breakthrough
08:29 Blogging, Networking & PR Visibility
12:27 Books, Going Solo & Rejection Mindset
22:44 Quality, Delegation & Posting Strategy in the AI Era
28:31 Research as a Brand Moat & Turning Studies into Campaigns
34:07 Headline Crafting & Demand Driven Topics
36:44 AI, Job Security & Personal Brand Urgency
41:33 Workplace Shift Post COVID & Authority Capital
46:04 Rapid Fire & Start Small Philosophy 50:32 Where to Find Dan
54 min
April 23His Brand Made Him Famous, But It Almost Destroyed Him | Thomas Edwards Jr. | Ep.10
Thomas Edwards Jr. built one of the most recognizable personal brands of his generation. He was the real-life Hitch. Wall Street Journal. CNN. Steve Harvey. Tamron Hall. ABC Nightline. MTV. Axe. Maxim. Over 400 media appearances. He helped 400 people find love and get married. By every external measure, he was winning.
He was also slowly disappearing.
In this episode of Return on Reputation, Justin sits down with Thomas Edwards Jr. — founder of The Professional Wingman, coach, and author of the forthcoming book The One Up Effect — for one of the most honest conversations the show has ever had. Thomas unpacks what happens when you fuse your personal identity with a brand so completely that you lose the line between the two, how the validation addiction took hold, and how getting sober in 2019 became the win that didn't look like one.
This one hits different. It's not just a founder story — it's a warning and a blueprint at the same time.
What you'll learn in this episode:
Why being the face of your brand is not the same as having a personal brand — and why the difference matters enormously
How Thomas went from sleeping on the floor next to Gary Vaynerchuk at South by Southwest to launching one of the most media-covered personal brands of the 2010s
The moment a Wall Street Journal article made him the second most-read story of the week — right behind the Obamacare proposal
What it costs when you build a brand that's bigger than the person behind it
Why he cut video games out of his life for a decade — and what that one decision reveals about identity and authenticity
How the One Up Effect framework helps service-based business owners grow revenue without destroying their families or themselves in the process
Why your massive L will ultimately lead to your greatest win
If you're a founder who's ever felt like your brand was a cage — or worried it might become one — this episode is required listening.
Follow Return on Reputation on YouTube, Spotify, and Apple Podcasts so you don't miss an episode.
Hashtags: #PersonalBranding #FounderStory #Entrepreneurship #Authenticity #B2BMarketing #MentalHealth #SobrietyStory #BrandBuilding #TheOneUpEffect #ReturnOnReputation
Timestamps:
00:32 Boston Twitter Scene & Gary V Meetup
05:03 SXSW: How Wingman Was Born
09:40 Authenticity Over Algorithms
11:58 Wall Street Journal Breakthrough
13:38 Brand Identity Trap & Media Wins
21:30 Losing Purpose, Burnout & Identity Collapse
25:09 Standing Out in the AI Era
27:01 Letting Wingman Die & Launching The One-Up Effect
33:38 Coaching Service Businesses
36:42 The 12 Streams Fulfillment Framework
39:40 Design Your Own Game & The Super Mario Metaphor
43:47 Play Drives Innovation & Business Creativity
47:50 Client Growth & The Party Referral Strategy
48:43 How To Know If Your Brand Is A Mask
49:46 From Invisible To Known: Building a Personal Brand Today
53:50 Gary V In One Word & Biggest Loss To Biggest Win
1 hr 1 min
April 16He Killed His Drink Brand After 10 Years — Then Built a Golf Empire | Jon Mason | Ep.9
What does it really take to kill your own brand — and rebuild it into something better? In this episode of Return on Reputation, host Justin Obey sits down with Jon Mason, founder of Swing Juice, for a raw and honest founder story about entrepreneurship, brand building, and the pivot that changed everything.

Jon spent nearly a decade building Swing Juice as an all-natural hydration and energy drink inspired by his love of golf — bootstrapped from his own bank account, cases loaded into his trunk, doors knocked on one at a time. In 2014, he made one of the hardest calls any founder can make: shut it down. He kept the name, threw out the product, and bet everything on a new idea — cool golf graphic tees for people who love golf, hip hop, tacos, and life outside the country club. Today, Swing Juice is a legitimate golf apparel brand with a team of eight, partnerships with the USGA and the MLBPA, and over 77,000 social followers.

What you'll learn in this episode:
How Jon turned a phrase overheard at a 6:30 AM tee time into a trademarked brand — the same night
Why killing the beverage business after 10 years was the right call, and how he knew it
How he created a new category in golf apparel by building products around what he personally loved
Why founders are afraid to put their face in front of their brand — and what finally convinced Jon to step out from behind the curtain
Why going viral is a trap, and what consistency actually looks like on social over the long haul

If you're a founder who's ever considered pivoting, struggled to let go of control, or wondered when to start building your personal brand alongside your business — this episode is for you.
Follow Return on Reputation wherever you listen to podcasts so you don't miss an episode.
Hashtags
#Entrepreneurship #PersonalBranding #FounderStory #B2BMarketing #GolfLifestyle #StartupJourney #BrandBuilding #PivotStory #SmallBusiness #ContentMarketing

TIMESTAMPS:
02:49 The Swing Juice Name Spark
05:12 Building The First Beverage
07:35 Personal Brand Before Social
11:10 The 2014 Pivot Decision
13:09 Creating Golf Graphic Tees
17:27 First Shirt Sold Online
19:48 From Solo Hustle To Team
23:24 No Blueprint for Growth
24:01 Hiring and Letting Go
05:02 Community as a Catalyst
25:27 Bootstrapping and Obsession
26:39 Brand vs Personal Social
29:00 Founder Face and Fear
32:48 Building Personal Brand Today
35:06 AI Tools and Human Touch
38:02 Landing Major Partnerships
39:49 Five Year Vision Ahead
40:58 Rapid Fire Golf and Brands
45:40 Consistency Beats Viral
49 min
April 09Show Up or Get Outspent | Programmatic Advertising, Personal Brand, and How B2B Deals Actually Close | Jessica Chase | Ep.8
Most founders chase the next ad format, the next platform, the next growth hack. But what if the thing that was actually closing deals was just you, posting honestly on LinkedIn every week, even when it felt cringe?

In this episode of Return on Reputation, my guest is Jessica Chase, Co-Founder of getabovethefold.com , a programmatic advertising agency helping brands scale beyond Google Ads into streaming TV, podcasts, audio platforms, and beyond.

Jessica is one of those founders who figured out early that reputation is the real growth channel. She did not land clients by outspending competitors or running a perfect funnel. She built 19,000 followers on LinkedIn by posting authentically, sometimes uncomfortably, once a week for an entire year. And the deals followed.

With over 20 years in marketing, Jessica started at 1-800-CONTACTS at 18, moved through international agencies, and eventually asked herself a question most marketers are afraid to ask: why am I making other people millions of dollars instead of myself?

In this episode we cover:
What programmatic advertising actually is and how it differs from Google Ads
When founders should start investing in programmatic vs other ad formats
How geo-fencing corporate offices and events can accelerate a B2B sales cycle
Why last-click attribution is killing your marketing strategy
How to build a personal brand on LinkedIn without feeling like you are performing
Why posting when it feels cringe is actually the most powerful thing a founder can do

Keywords: programmatic advertising, personal brand for founders, B2B marketing strategy, LinkedIn personal branding, Google Ads vs programmatic, ABM strategy, founder marketing, Return on Reputation podcast

About Jessica Chase Co-Founder of getabovethefold.com , a programmatic advertising agency helping brands scale beyond Google Ads. 20+ years in marketing, former client and agency side, now building one of the few agencies fully specialized in programmatic advertising. https://www.linkedin.com/in/programmaticmarketing/

About Return on Reputation: Return on Reputation is the show for founder-led brands done flying under the radar. Host Justin Obey, founder of Obey Creative, sits down with experts, founders, and dealmakers to unpack how personal brand, trust, and authority compound into real business leverage. New episodes every week.

Connect with Justin Obey: LinkedIn: https://www.linkedin.com/in/justinobey YouTube: https://www.youtube.com/@JustinObey Website: https://obeycreative.com

TIMESTAMPS:

01:26 What Get Above the Fold Does
02:28 Founder Mindset and Self Care
04:06 Meditation and Hypnotherapy
09:18 Why She Started the Agency
12:37 Programmatic Advertising Explained
14:24 When to Use Programmatic
18:13 ABM and Event Targeting
21:52 Connected TV and Ad Formats
24:14 Building Trust in a Technical Industry
27:15 Why Clicks Are Not the Whole Story
29:29 Personal Branding on LinkedIn
33:39 Why Founders Should Be the Face
35:50 Posting Through Fear and Haters
41:41 How Failure Builds Confidence
42:57 Rapid Fire and Wrap Up
51 min
April 02Reputation Raised This $10.5M Fund: The Visible Hands Fund Model | Justin Kang | Ep.7
What does it actually take to raise a venture fund when no one would have hired you to run one? And how do you build the kind of reputation that convinces 80 people to bet their money on you before you have ever written a single check?

I sat down with Justin Kang, Co-Founder and Managing Partner of Visible Hands, a pre-seed venture capital fund investing in underrepresented founders across Boston, New York, and the American South.I wanted to get him on the show because his story is one of the clearest examples I have ever seen of reputation functioning as actual currency.

Justin did not come up through Goldman Sachs or get recruited out of Stanford. He spent his twenties moving between politics, nonprofits, and civic organizations, building relationships without a master plan. Then in 2020, he and two co-founders launched a pre-seed fund from scratch with no institutional track record and no traditional pedigree. Just 15 years of trust, built one relationship at a time. Today, Visible Hands has made more than 100 investments, closed a first fund at 10.5 million dollars with 80 limited partners, and generates 3 million dollars annually through partnerships with cities, family offices, and foundations.

This conversation changed how I think about deal flow, founder evaluation, and what it really means to build authority before you need it.

What you will learn in this episode:
Why micro venture capital funds statistically outperform large funds, and the business model problem that stops almost everyone from running one
How Visible Hands generates 3 million dollars a year through city and foundation partnerships, giving a micro fund the resources of a much larger operation
The three-part founder evaluation framework Justin uses before there is a product to judge: inspired insights, meaningful skill sets, and resource magnetism
Why nine out of ten pre-seed companies pivot from their original idea, and what Justin actually bets on instead
The three capital gaps blocking underrepresented founders: financial capital, social capital, and inspiration capital
Why the best founders build businesses so that investors chase them, and how that changes everything about how you should approach a raise
How Justin raised 10.5 million dollars without a traditional VC background, and what that proves about reputation as a substitutable form of credentialing
What founders should be doing right now, a full year before they are ready to raise, to build the authority capital that makes investors pay attention

If you are a founder who thinks you do not fit the profile, or you are sitting on an idea waiting until everything is perfect before putting yourself out there, this episode is a direct answer to that hesitation. Reputation is not built on where you went to school. It is built on who showed up for you when you asked, and that only happens if you spent years showing up for them first.

About Justin Kang Co-Founder and Managing Partner, Visible Hands. Former VP of Economic Growth at the Greater Boston Chamber of Commerce and early employee at MassChallenge. https://www.linkedin.com/in/justinjkang/

Timestamps:
0:00 — Justin Kang's non-traditional path to venture capital
4:30 — Why Visible Hands started in Summer 2020
8:00 — The "Visible Hands" name: a riff on Adam Smith's invisible hand
10:45 — How ecosystem-building generates deal flow AND $3M in annual revenue
15:30 — Pre-seed diligence: what Visible Hands looks for in a founder
21:00 — Resource magnetism, inspired insights, and why management consultants get a flag
26:00 — The danger of raising too much money too fast
31:00 — AI's impact on founder team size and check size
34:00 — How founder reputation plays into follow-on rounds from seed to Series A
38:30 — Financial capital, social capital, and inspiration capital: the three barriers to underrepresented founders
44:00 — How to build authority capital before you're ready to raise
49:00 — Rapid fire: warm vs. cold outreach, best book, and why LinkedIn wins
52:00 — Closing thoughts on entrepreneurship as privilege

Connect with Justin Kang: Website:https://www.visiblehands.vc/ LinkedIn: https://www.linkedin.com/in/justinkang

Connect with Justin Obey: LinkedIn: https://www.linkedin.com/in/justinobey YouTube: https://www.youtube.com/@JustinObey Website: https://obeycreative.com
52 min
March 26The Laws of Brand Storytelling: How to Build a Personal Brand That Compounds | Jessica Gioglio
How do you build a personal brand that compounds over time? What does it actually take to go from invisible to authoritative, and what are the laws of brand storytelling that make it all work?
Justin Obey sits down with Jessica Gioglio — bestselling author, keynote speaker, and founder of With Savvy Media & Marketing — to answer exactly that. Jess co-authored The Laws of Brand Storytelling and The Power of Visual Storytelling, has led award-winning marketing and PR programs for Dunkin' Donuts, TripAdvisor, and Sprinklr, and has spent two decades helping companies and founders tell the stories that actually move the needle.
This conversation is personal. Jess helped Justin get his first press hits — including coverage in the Boston Globe — when he was building Social Boston Sports from scratch. Fast forward nearly 20 years, and she's one of the most credible voices in brand storytelling. This episode is about what compounded.
They cover the Macro/Micro storytelling framework, why neutral brands are invisible brands, the CTFD Index Jess created at Dunkin', why AI is exposing weak strategy rather than replacing storytellers, and the exact playbook for founders who want to start building their personal brand today.
What you'll learn in this episode:
Why reputation compounds — and why most founders start too late
The Macro vs. Micro stories framework from The Laws of Brand Storytelling
Why brand pages are losing to personal brands on LinkedIn
How to build an authenticity playbook so your brand never crosses the wrong line
The CTFD Index — a crisis communications framework from inside Dunkin' Donuts
Why AI is exposing weak strategy, not replacing great storytellers
The human-AI-human sandwich approach to content creation
The one platform, one format, and one habit every founder needs to start today
Chapters:
00:00 — Introduction & Welcome
01:14 — The Comcast Sleeping Tech Story That Started It All
03:10 — The Savvy Bostonian Blog & Building a Personal Brand Before It Had a Name
05:14 — Was It Hard to Walk Away from Corporate? The Leap to With Savvy
07:00 — Using Side Projects as a Test Bed for Your Marketing Skillset
09:40 — Personal Brand as the New Career Security
12:00 — When Should a Founder Build a Personal Brand vs. Go Faceless?
13:05 — The Macro vs. Micro Stories Framework Explained
15:07 — The Dunkin' Pay-It-Forward Story (and What It Teaches About Brand Storytelling)
18:25 — Employee Advocacy: Why Employees Outperform Brand Pages
21:10 — Are Brand Pages Dead? The Shift to Founder and Executive Voices
23:00 — The Rise of B2B Influencers and Why It's Harder Than B2C
25:00 — The Laws of Brand Storytelling: Core Thesis Breakdown
28:48 — Why Neutral Brands Are Invisible Brands (The Switzerland Problem)
31:50 — The Neuroscience of Storytelling and Why Stories Beat Data
33:05 — How to Take a Brand Stand Without Crossing the Line
36:00 — The CTFD Index: Jess's Crisis Communications Framework from Dunkin'
37:50 — AI and Brand Storytelling: What Founders Need to Know Right Now
38:30 — What the CEO of Google DeepMind Told Jess About AI and Storytellers
42:25 — The Human-AI-Human Sandwich (Justin's Framework, Jess Approves)
43:45 — Why Companies Confuse a Growth Problem with a Branding Problem
46:35 — Rapid Fire Round
Connect with Jessica Gioglio: Website: https://jessicagioglio.com LinkedIn: https://www.linkedin.com/in/jessicagioglio Newsletter (The Marketer's Storybook): Available on LinkedIn and Substack The Laws of Brand Storytelling — available on Amazon The Power of Visual Storytelling — available on Amazon
Connect with Justin Obey: LinkedIn: https://www.linkedin.com/in/justinobey YouTube: https://www.youtube.com/@JustinObey Website: https://obeycreative.com
About Return on Reputation: Return on Reputation is the show for founder-led brands done flying under the radar. Host Justin Obey, founder of Obey Creative, sits down with experts, founders, and dealmakers to unpack how personal brand, trust, and authority compound into real business leverage. New episodes every week.
#PersonalBranding #BrandStorytelling #FounderBrand #ReturnOnReputation #JessicaGioglio #ContentMarketing #B2BMarketing #TheLawsOfBrandStorytelling #FounderVisibility #LinkedInMarketing #PodcastMarketing #OBEYCreative
49 min
March 19What Investors Actually Look For in Founders - Andrew Nash on Reputation, Risk & Building Again | Ep. 5
What separates founders who scale from the ones who stall? Andrew Nash has spent 40 years finding out.

Serial founder, investor, and entrepreneur Andrew J. Nash has built and exited companies acquired by Apple, eBay, Deloitte, and Chowly. After selling Targetable in 2024, he moved back to Australia ready to step back - and then AI pulled him right back into the arena.

Now he's building again: launching Austral Impact to strengthen the Australian startup ecosystem, developing Kemu (a vendor-agnostic AI orchestration platform), teaching as an Enterprise Professor at the University of Melbourne, and hosting his own podcast, Big Bets and Bad Calls.

In this conversation, Justin and Andrew get honest about what a 40-year career of exits actually comes down to — and it's not the technology. It's the trust.

What we cover:
Why Andrew left retirement to build again — and what he saw in AI that others missed
What Kemu is and why vendor-agnostic AI orchestration matters
How Austral Impact is filling a critical gap in the Australian startup ecosystem
What Andrew looks for in a founding team before writing a check
Whether personal brand and reputation actually influence investment decisions
The case for founder-led brands in B2B
Big bets he's proud of — and bad calls he'll put on the record

If you're a founder, investor, or operator building something that's meant to last — this one's for you.

Episode Chapters:
00:00 — Introduction & How Justin and Andrew Met
01:00 — Andrew's 60-Second Career Pitch (The Forrest Gump Version)
03:00 — Why AI Pulled Him Out of Retirement
05:15 — Learn, Earn, Return: The Framework Behind Everything Andrew Does
08:00 — Austral Impact: Closing the Gap in the Australian Startup Ecosystem
09:30 — Why He Started Big Bets and Bad Calls (And What the Name Really Means)
20:30 — Kemu Deep Dive: Building the AI Orchestration Platform of the Future
34:00 — We're Only 1-2% Into the AI Revolution
40:30 — Is Reputation the Real Throughline Behind Andrew's Exits?
43:00 — Jockey Over Horse: How Andrew Evaluates Founders Before Investing
47:00 — Founder-Led Brand: Vanity Play or Business Necessity?
49:00 — The #1 Role of a Founder and What to Look for in a Team
52:00 — The Biggest Bet of His Life (Moving to the US in the 90s)
53:00 — Risk, Resilience, and Running Hard at It

Connect with Andrew Nash: 🔗 LinkedIn: linkedin.com/in/andrewjnash 🎙️ Big Bets and Bad Calls: [URL] 🌐 Austral Impact: [URL] 🤖 Kemu: [URL]
Return on Reputation is hosted by Justin Obey, founder of OBEY Creative. New episodes every week at the intersection of reputation, visibility, and business growth.
🔗 LinkedIn: [URL] 🌐 OBEY Creative: [URL] 📩 The Authority Brief: [URL]

#PersonalBrand #FounderStory #Entrepreneurship #ReturnOnReputation #AndrewNash #AIStartups #FounderLedBrand #B2BMarketing #StartupPodcast #Reputation
55 min
March 12Ep. 4 | Burned at Age 8, Told He’d Never Compete Again — Now a Top 1% IRONMAN Athlete | Shay Eskew | Return on Reputation
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How do you pick yourself up when your life changes forever in just three minutes? And more importantly, how do you transform your scars—both physical and emotional—into the foundation of an unbreakable reputation that inspires thousands? This episode is a deep dive into the heart of true resilience and the "competitor" identity.

I’m Justin Obey, and on Return on Reputation, we talk to leaders who understand that character isn’t built when things are easy; it’s forged when you decide not to quit during your darkest hours.

My guest today is Shay Eskew. Shay’s story is, quite simply, a miracle of willpower. At eight years old, a horrific accident left him with burns over 65% of his body and a medical prognosis that said he’d never compete in sports again.

Today, Shay is not only a highly successful sales executive and author, but a world-ranked Ironman triathlete in the top 1%. He has turned what many would see as a tragedy into his greatest asset: a personal brand built on radical authenticity and a refusal to be a victim.
Shay breaks down why being "memorable" is far more powerful than being perfect, and how pain, when embraced with gratitude, becomes the fuel for a life without limits.

What we unpack in this conversation:
Competitor vs. Finisher: Why Shay refuses to just "get through" a task and how the mentality of going all-in separates exceptional leaders from the average.
The Vulnerability Advantage: How sharing your rawest failures—from grueling surgeries to forgetting your family’s passports—builds a level of trust with clients that traditional marketing can’t touch.
Choose Your Hard: The powerful philosophy of understanding that life will be difficult regardless, so you might as well choose the "hard" that leads to growth and discipline.
Reputation in the Boardroom: Shay’s secret to walking into a room and being the person everyone remembers, using his unique story to break through the noise and close multi-million dollar deals.
The Legacy of Grit: How to balance the ambition of an Ironman with being the father and husband your family deserves, ensuring that success at the top isn't a lonely finish line.

If you’re a founder going through a season of loss, or if you feel like your "scars" are holding you back, Shay is here to remind you that you are uniquely adapted to handle adversity.

Because at the end of the day, your reputation isn’t about what happened to you—it’s about who you chose to become because of it. Greatness isn't given; it’s earned in the fire.

About Shay Eskew:

Shay Eskew is a world-ranked Ironman triathlete, a highly successful sales executive, and a burn survivor who has turned unimaginable adversity into a blueprint for peak performance. After an accident at age eight left him with burns over 65% of his body and 40+ surgeries to follow, Shay defied medical odds to become a top 1% Ironman competitor and a sought-after motivational speaker.

With a career built on the mantra that "anything worth doing is worth overdoing," Shay has mastered the art of Authentic Resilience. He leverages his unique story to build deep trust in the boardroom, proving that vulnerability and grit are a leader's most valuable assets. He is the author of the bestseller What the Fire Ignited, where he teaches others how to stop being victims of their circumstances and start being competitors in their lives.

About Return on Reputation:

Return on Reputation is the show for founder-led brands that are done flying under the radar. Every episode, host Justin Obey, founder of Obey Creative, sits down with experts, founders, and dealmakers to unpack how personal brand, trust, and authority compound into real business leverage. We talk strategy over shortcuts, substance over viral moments, and real frameworks for turning your reputation into revenue.

Connect with Shay Eskew:
Website: https://www.shayeskew.com/
LinkedIn: https://www.linkedin.com/in/shayeskew/
Instagram: @mr_shay_sq

Connect with Justin Obey:
LinkedIn: https://www.linkedin.com/in/justinobey/
YouTube: https://www.youtube.com/@JustinObey

CHAPTERS:

01:15 Choose Your Hard
03:11 The Burn Accident
05:47 Surgeries And Identity
09:11 Gratitude And Defiance
12:31 Never Quit Mindset
17:23 Triathlon Disaster Day
22:56 Daily Routine And Prayer
24:42 Family First Priorities
27:29 All In Competitor
29:01 All In Training Mindset
30:55 Bear Trapping Adventures
33:00 Athlete Identity In Business
34:20 Be Memorable In Sales
36:26 Authentic LinkedIn Branding
38:52 Vulnerability Builds Trust
41:45 Epic Passport Failure Story
45:02 Book Lessons From Hardship
48:48 Luck Faith And Timing
50:34 Write The Damn Book
53:58 Reputation And Identity
55:42 Seek Discomfort Oggi
57:35 Where To Find Shay
1 hr

About Return on Reputation

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I'm Justin Obey, and this is Return on Reputation.

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