Return on Reputation

Justin Obey

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

Here's what I've learned building companies and helping founders scale: The game has changed. You don't need a bigger ad budget - you need a better media strategy.

This show is about how founders are building authority and leverage in 2026:

Podcasting that generates real clients, not just downloads
AI tools that actually save you time instead of creating busy work
Social media that builds relationships, not just follower counts
Founder-led branding that positions you as the obvious choice

I've built a 7-figure company, I run marketing for multiple 7 and 8-figure brands, and now I help B2B founders build the media engines that let them stop chasing and start attracting.

If you're ready to play a different game, let's go.

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#62
Thursday · 41 min· Video
The LinkedIn System for Execs Who Have No Time to Post | Jeffrey Zhao, Ordinal | EP.30
When Jeffrey Zhao was running Slope, a design and marketing agency, his team did organic social for B2B companies. They tried every tool out there. None of them fit. Sprout, Hootsuite and Sprinklr were built years ago for consumer brands, back when social meant brand awareness and not much else. B2B needed something different: execs posting, employees engaging, approvals moving fast, and a way to tie all of it back to pipeline. So Jeffrey built it. That’s Ordinal, and he was the customer before he was the vendor. I brought Jeffrey on because I use Ordinal every day (this isn’t a paid episode, I promise) and because he can see who posts and who goes quiet across a huge number of B2B companies. That view makes the pattern hard to ignore. Company page reach has dropped more than 60% in the last two years. Meanwhile, the companies winning on LinkedIn have execs and employees posting every week. People buy from people. The hard part is making that consistent when your CEO is stuck in board meetings. We got into why exec teams stop posting (usually they just get busy), why “I have nothing interesting to say” is almost never true, and how one social manager can now run content for 20 execs plus an employee program, a job that used to take 10 people. Jeffrey also shared how Clay grew its LinkedIn from 8,000 followers to over 120,000 with a one-person social team, and why writing the post is only about 10% of the work. What you’ll learn Why B2B social covers the whole funnel, from brand awareness down to closing deals The three reasons exec teams go quiet on LinkedIn, and the one role that keeps them posting 3 to 5 times a week Why LinkedIn feels “cringe” to people who don’t use it (and what they’re missing) How to find 3 to 5 posts’ worth of ideas a week in your call recordings, Slack threads and Notion docs The CFO who headlines finance conferences for thousands of people and still thought he had nothing to say How posting on LinkedIn can raise your cold email response rates, even when nobody engages with the post Why your LinkedIn posts work as built-in social proof in the middle of a long deal cycle The two-second profile fixes that 90% of companies skip, even though prospects are one click away from booking a demo How Clay scaled to 15 to 20 execs posting every week with a tiny team Where AI helps, where it turns into slop, and why hiring a human still gets most teams better results today Rapid fire: the most underrated post format, whether there’s a best time to post, the LinkedIn habit Jeffrey would ban, and if you should keep or kill your company page TIMESTAMPS 00:00 Intro: LinkedIn for B2B Growth 00:08 How LinkedIn Builds Business 00:47 From Agency to SaaS: Slope to Ordinal 04:01 Why B2B Social Media Is Different 05:08 Executive and Employee Advocacy 08:01 AI in Social Media Management 10:11 Why Executives Stop Posting on LinkedIn 14:31 No Time and Nothing to Say? Fix It 20:05 Personal Profiles vs Company Pages 21:50 Authentic LinkedIn Posts That Work 22:23 How Thought Leadership Drives Pipeline 23:53 LinkedIn Posts as Social Proof in Sales 24:52 LinkedIn DMs and Profile Optimization 27:11 Clay’s LinkedIn Growth Case Study 29:21 Executive LinkedIn Posting Strategy 32:18 AI Writing vs Human Content 36:01 Content Approvals in Slack 36:40 Rapid Fire: LinkedIn Tips 38:51 What Reputation Means + Wrap Up GUEST Jeffrey Zhao, Co-founder of Ordinal. Ordinal: https://www.tryordinal.com/ LinkedIn: https://www.linkedin.com/in/zhaojeffrey/ HOST Justin Obey, founder of Obey Creative. We help B2B founders turn cold outbound into warm conversations through a podcast-driven content engine. One episode per week. Your prospects know and trust you before your sales team ever picks up the phone. First episode live in 30 days. LinkedIn: https://www.linkedin.com/in/justinobey/ Website: https://obeycreative.com/ SHOW Return on Reputation explores how founders and business leaders turn expertise into trust, authority, relationships and business growth. Subscribe to Return on Reputation for more conversations about personal branding, leadership and building a business people trust.
#61
October 8 · 41 min· Video
The Hidden Cost of Being Invisible | Aman Devgan, Menufy | EP.29
A great restaurant can lose a customer before that person ever tastes the food. Aman Devgan, President and General Manager of Menufy by HungerRush, joins me to talk restaurant marketing, online reputation and the cost of being invisible. In Menufy's survey of 1,000 U.S. consumers, 59% said they'd decided not to order from a restaurant because they couldn't find basic information online. Among Gen Z, it was 71%. Wrong hours. An outdated menu. Customers who leave without ever telling the owner why. We talk about how independent restaurants can take back their customer relationships from third-party delivery apps, make direct online ordering easier, and turn Google reviews into more business. Aman shares customer stories, explains how Menufy is testing AI-powered personalized marketing, and breaks down his approach to building teams that outlast the leader. Then we get into something more personal. Aman has built a reputation with boards, business partners and teams, but he's been reluctant to share it publicly. His reason will sound familiar to a lot of experienced founders and executives: making decisions with incomplete information is part of the job. Being wrong in public feels different. We talk about personal branding without performing, sharing what you've learned, and treating social media as a way to help people. WHAT YOU'LL LEARN Why restaurants lose customers before they ever place an order How direct ordering helps owners regain control of their guest relationships Why Google reviews and an accurate Google Business Profile matter to restaurant growth How Menufy is testing AI to make restaurant marketing more personal Why accountability, honest feedback and daily behavior shape company culture The leadership lesson Aman never forgot: everyone has a gift Why experienced executives hesitate to build a public personal brand How to create useful content without pretending to have every answer TIMESTAMPS 00:00 Meet Aman Devgan of Menufy 02:36 Why Restaurants Lose Customers Before They Order 06:50 Rising Prices and Restaurant Profitability 08:36 Menufy, HungerRush and Taking Over a Founder-Led Business 12:36 Leadership, Accountability and Company Culture 16:07 The Leadership Lesson Aman Never Forgot 17:49 Direct Ordering and Independent Restaurant Stories 20:24 What Menufy's Marketing Platform Does 23:05 AI and Personalized Restaurant Marketing 24:50 Taking Back Control of Customer Relationships 26:04 Google Reviews, Reputation and Direct Orders 28:01 Why Experienced Executives Stay Invisible 31:45 Personal Branding Without Performing 35:06 What Aman Would Share Publicly 36:55 Rapid Fire: Google Listings, Leadership and Restaurant Tech 38:35 What Reputation Means to Aman 39:25 Where to Find Aman and Menufy GUEST Aman Devgan, President and General Manager of Menufy by HungerRush. Menufy: https://restaurant.menufy.com/ LinkedIn: https://www.linkedin.com/in/amandevgan/ HOST Justin Obey, founder of Obey Creative. We help B2B founders turn cold outbound into warm conversations through a podcast-driven content engine. One episode per week. Your prospects know and trust you before your sales team ever picks up the phone. First episode live in 30 days. LinkedIn: https://www.linkedin.com/in/justinobey/ Website: https://obeycreative.com/ SHOW Return on Reputation explores how founders and business leaders turn expertise into trust, authority, relationships and business growth. Subscribe to Return on Reputation for more conversations about personal branding, leadership and building a business people trust.
#60
October 1 · 47 min· Video
Brands Don't Build Authority. People Do. | Matt Crane, MGMT Boston | EP.28
When Matt Crane moved back to Boston after a decade in the San Francisco startup scene, he kept asking everyone one question: "What are the five best startups in Boston?" Nobody could name five. So he started a newsletter as a side project. Almost four years later, MGMT Boston is one of the fastest-growing local media companies for venture-backed startups, with a newsletter, a newsfeed, a podcast, a short-form video series and a lot of in-person events. It still has one full-time employee. Him. I brought Matt on, live at Startup Boston Week, because he's the face of a company he insists is a business, not a personal brand. He never wanted to be on video. He did it anyway, in person, and that's when everything started moving faster. By the end of this conversation, we landed on something more useful than "build your personal brand": people trust people, and the fastest way to earn that trust is to put someone else in the spotlight. We also got into how he runs a media company with one full-time person and about half a dozen contractors. His plan is to "agentify" everything operational and put every human hour into the one thing AI can't fake: showing up in person. He's picky about who he partners with, too. He'd rather wait for the best startups to come to him than fill a slot with the wrong company, because the companies he highlights are the brand. And he's honest about what it cost to get here, including two slow Augusts when he wasn't sure MGMT would ever become a real company. What you'll learn Why Matt chose to compete hyperlocal, digital and in person all at once, after learning in ad tech how brutal the "darkest oceans" of competition can be The moment he realized a media company without video doesn't work, and why he calls it an expansion instead of a pivot Why he thinks you have to put your own face on it first if your reputation is on the line, instead of hiring reporters to do it for you What Bill Gates, Microsoft and Lenny's Newsletter taught him about why people outpace brands on the internet Why he calls personal branding "the worst branding ever," and what the best creators do instead How a one-person media company uses AI to publish a funding story in about 45 seconds, and where he refuses to let AI do the work His advice for anyone uncomfortable on camera, including the harsh YouTube Shorts comment he couldn't argue with (it hurt, and he deleted it) The "sign it in blood" commitment he thinks every creator needs, and why debating whether to post on Tuesday or Wednesday means you've already lost The hardest part of growing past the early stage: saying no to good opportunities so you can chase the great ones The two Augusts when he wasn't sure MGMT had enough momentum to become a real company, and why he has no plan B TIMESTAMPS: 00:00 Matt Crane's Founder Story 01:31 From Finance to Startups and Back to Boston 04:39 How MGMT Boston Started 08:47 Hyperlocal Media and IRL Events 10:19 From Newsletter to Video Content 12:37 Why Founders Should Be the Face of the Brand 19:07 Covering Venture-Backed Startups 21:57 What Makes a Great Founder 24:46 Scaling Content Without Losing Quality 26:09 Saying No to Good Opportunities 28:40 AI-First Company: AI vs Human Content 32:21 Getting Comfortable on Camera and Staying Authentic 37:03 Startup Partnerships and Ecosystem 39:31 Expanding to Life Sciences 40:17 Business vs Personal Brand 41:36 Rapid Fire: Boston Startup Scene and No Plan B 45:47 Where to Find MGMT Boston Guest: Matt Crane, Founder of MGMT Boston https://mgmtboston.com/ https://www.linkedin.com/in/matthewhcrane/ Host: Justin Obey, founder of Obey Creative. Obey Creative helps B2B founders who are invisible in their market solve a zero inbound pipeline by delivering a podcast-driven content engine from one conversation per week. First episode live within 30 days. https://www.linkedin.com/in/justinobey/ https://obeycreative.com/ Show: Return on Reputation. Reputation drives everything. Without trust, building a strong business is close to impossible. The companies that lean hardest into the personal brands of their founders and their people will outperform the ones that don't.
#59
September 24 · 39 min· Video
Build Your Network Before You Need It | John Hill (LinkedIn, Techstars, Whop) | EP.27
John Hill hasn't applied for a job in 25 years. His reputation keeps opening the door. Recorded live on stage at Startup Boston Week, John (VP of Story at Whop) walks through a career built on relationships. A sports journalist handed a website in 1997. The Michigan State alumni director helping people find work in the 2009 recession. The face of LinkedIn's higher education push. A decade building the Techstars global network. And now Whop, where anyone can start a business with AI. The most useful part for founders is his system. He takes 20 actions on his network every weekday, about 15 to 20 minutes a day, and it adds up to roughly 5,000 moments of help a year. He also explains why mapping the 100 people who can change your company's path matters more than your go-to-market plan. In this episode: Why founders now have to build two brands, their own and the company's How to build your network before you need it Why entrepreneurship is a skill you can learn "Investors need you. You don't need investors." His dad's story, from Savin Hill to Wharton, and a business card from a stranger at Penn Station Why trust and community become the real assets in the AI era Why he bought Cazenovia College Chapters: 00:00 Live at Startup Boston Week 00:26 From sports journalist to accidental founder 01:51 "Bless your heart": building alone in 1997 03:15 Jump off the cliff, build the plane 05:02 Techstars and the give-first network 06:32 Getting a job vs. being the job 09:31 Recruited by LinkedIn 11:32 "I haven't applied for a job in 25 years" 12:49 Build your brand and your company's brand 13:15 Map the top 100 people for your startup 14:00 20 network actions a day 15:22 64,000 investable startups vs. 8 billion people 16:28 Why he joined Whop 17:55 LinkedIn found you a job. Whop is the job. 19:03 Broken for corporate 19:53 Entrepreneurship is a skill 22:42 His dad's story: Savin Hill to Wharton 25:57 The stranger with golf clubs at Penn Station 29:21 Always the dumbest person in the room 30:10 Reputation, network and trust in the AI era 31:34 Rapid fire 32:35 Investors need you 33:10 Best founder stories: SendGrid and a 19-year-old on Whop 34:43 What reputation means to John 36:18 He bought a college 37:41 Keep dreaming big Connect with John Hill LinkedIn: https://www.linkedin.com/in/msuaajohn/ Whop: https://whop.com Return on Reputation is hosted by Justin Obey, founder of Obey Creative. Conversations with founders about the reputation that builds companies. Obey Creative: https://obeycreative.com #ReturnOnReputation #StartupBostonWeek #PersonalBrand
#58
September 3 · 46 min· Video
Personal Branding Now Beats the Company LinkedIn Page | Marie Burke Brown | EP.26
Marie Burke Brown spent the first stretch of her career inside enterprise giants like NetApp and VMware, building programs for products she didn't build and didn't choose. Then she did something most marketers don't: she jumped on purpose into a company with 22 people, then one with 30, because she wanted to be in the room before there was a room. Six months into her current role as VP of Marketing at Kibo, with nobody having sat in that seat before her, she did a full brand refresh before she had a single dashboard to prove it worked. I brought Marie on because I wanted to argue out the brand-vs-growth debate that never dies in B2B marketing. She's spent her whole career inside that tension, obsessing over positioning and narrative one minute, then getting asked by a board member to prove pipeline impact the next. Where we landed by the end of this conversation is more useful than either side of the argument: brand isn't the opposite of growth, it's the thing that makes growth cheaper, and there's a very specific, almost accidental reason her last product launch (backpacks, of all things) outperformed everything else at the booth. What you'll learn Why she ran a full brand refresh in her first few months at Kibo, before building a single reporting dashboard, and the one comment from a stranger at a trade show booth that told her it worked The "find and replace the company name" test she uses to catch AI-written messaging that could belong to any competitor Why she refuses to let AI create her positioning, only refine it, and what gets lost the moment you do it the other way around The three levels of technical depth she prepares for every persona, and why finance, not engineering, decides whether a message survives the board room Her actual content process: keyword clustering by product pillar (Snowflake, Databricks, FinOps) instead of just publishing whatever's trending Why she thinks the LinkedIn algorithm has quietly made an individual's personal brand worth more than the company page, and the one rule she uses to get an entire engineering team posting without sounding scripted The swag decision she almost didn't make that ended up on more than half the floor at a major industry conference Why "never burn a bridge" isn't a cliché to her, it's literally how she got both of her last two jobs, without ever applying to either TIMESTAMPS: 00:00 Meet Marie Burke Brown 00:48 Series A Marketing Reality 04:50 Solo Marketing Team 07:24 Career Path To FinOps 09:34 Working With The Board 12:34 Brand Vs Pipeline 15:15 Kibo's Brand Refresh 17:29 Kibo's Agentic AI 18:57 Marketing Tech To Buyers 22:19 Messaging By Audience 24:27 SEO Content Pillars 26:07 AI And Messaging Risks 28:01 Building Company Evangelists 28:56 Networking Built Her Career 32:40 Executives As Public Faces 34:21 Authentic LinkedIn Branding 42:46 Rapid Fire Questions 45:24 Where To Follow Marie Guest: Marie Brown, VP of Marketing at Keebo. https://keebo.ai/ Find her on LinkedIn. https://www.linkedin.com/in/marieburke/ Host: Justin Obey, founder of Obey Creative. Obey Creative builds personal brands and communities for founder-led companies through brand strategy, video-first social media, content creation, and podcasting. https://www.linkedin.com/in/justinobey/ Show: Return on Reputation. Reputation drives everything. Without trust, building a strong business is close to impossible. The companies that lean hardest into the personal brands of their founders and their people will outperform the ones that don't.
#57
August 20 · 48 min· Video
Invisible CEOs Lose Millions in Deals and Talent | Katie Radel | EP.25
Katie Radel grew up above a funeral home. Third generation family business. I love stories like that because it explains a lot about why she never questioned whether entrepreneurship was even on the table for her. She spent the next several years in the corporate world (banking, healthcare, finance) before she got close to 40, had just had her son, and realized the version of herself showing up to that job every day wasn't the healthiest one. Six months before the pandemic hit, she quit and started Ripple Consulting Group. I brought Katie on because I wanted to argue this out loud, the whole earned, owned, and paid media thing. She lives in earned media (PR, pitching journalists, getting executives quoted). I live in owned media (building the content and community side). Neither of us thinks the other one wins by itself. Where we landed by the end of this conversation is way more interesting than the debate, honestly. There's an actual number on what it costs a company when its executives stay invisible, and AI just made earned media matter more, not less. What you'll learn Why 84% of AI citations trace back to earned media, and why that means PR isn't optional anymore if you care how AI talks about you The stat Katie leads with in every pitch meeting: visible executives carry an 80% higher average share price than the ones who stay invisible How to tell if a founder saying "I don't have time for this" actually means that, or means they don't want to be the one taking the risk The one question I stole from Katie that gets someone to their actual zone of genius, because asking "what's your expertise" gets you nothing useful The most overrated PR tactic there is: sending a press release out on the wire with zero strategy behind it The one line to fix on your LinkedIn headline today (hint: it's not your job title) Why even the executives with the most credentials still deal with imposter syndrome, and how Katie gets them talking before she ever shows them a talking point Why video is winning right now. In a feed full of AI slop, showing up live and unscripted is the one thing that's hard to fake Why reframing "personal brand" as "service media" turns the fear of self promotion into the reason you actually post TIMESTAMPS 00:00 Meet Katie Radel 00:48 Her Midlife Career Pivot 03:43 First Business and Hospital PR 05:41 Why She Leaped Again at 40 06:46 Funeral Home Entrepreneur Roots 08:34 Earned vs Owned vs Paid Media 10:36 When to Start Your PR Push 12:49 Finding Your Point of View 14:59 Prepping Executives for Press 15:53 Fear and Imposter Syndrome 17:58 Why Earned Media Builds Trust 20:20 AI Is Fueling PR's Rise 21:09 PR Strategy Before Tactics 23:26 Why Executive Brands Win 25:22 Building Camera Confidence 25:57 The Earned Owned Paid Mix 27:01 Finding Your Zone of Genius 29:23 Video in the Trust Economy 31:49 Coaching Camera Shy Executives 34:35 The Cost of Invisibility 38:28 The Real Time Commitment 40:45 Visibility Without the Humblebrag 43:26 Rapid Fire Questions Guest: Katie Radel, founder of Ripple Consulting Group, executive visibility and PR strategist. Find her on LinkedIn. https://www.linkedin.com/in/katieradel/ Host: Justin Obey, founder of Obey Creative. Obey Creative builds personal brands and communities for founder-led companies through brand strategy, video-first social media, content creation, and podcasting. https://www.linkedin.com/in/justinobey/ Show: Return on Reputation. Reputation drives everything. Without trust, building a strong business is close to impossible. The companies that lean hardest into the personal brands of their founders and their people will outperform the ones that don't.
#56
August 13 · 1 hr 9 min· Video
Why an Audience Is the Best Asset a Founder Can Own | Vincent Pierri | EP.24
Vincent Pierri spent years writing a new forty-five-minute talk every week for a room of three hundred people. No teleprompter. No rehearsal. Cross four or five hundred people, he says, and loyalty stops being the reason anyone shows up. They come back only if the message actually gives them something. That weekly pressure to never repeat himself built the exact skill he sells today. After leaving the pulpit, Vincent started out coaching SaaS executives on their conference talks, and by accident discovered that his rough, unpolished infographics were going viral while his videos went nowhere. Today he has around 34,500 LinkedIn followers and helps founders and executives turn their expertise into content people actually save. In this episode, Vincent and Justin Obey argue video versus infographics, agree that neither one wins on its own, and land on the thing underneath both formats: without a content strategy, the format doesn't matter. What you'll learn Why 99% of CEO keynotes are boring, and the ten-bullet fix that would make you sound like the best communicator in the room How to find your true top of funnel by testing which format your audience actually rewards, instead of copying whoever is loudest What AI can and can't create for you, and why AI is best at making content about AI itself The 3% save-rate rule, and what LinkedIn is really telling you in the first hour after you post Why you should stop chasing impressions and start raising your rates instead How one infographic about airline loyalty programs became a consultant's biggest source of pipeline for an entire year The mind-map method for finding topics nobody else is covering, demonstrated live on the show Why the fear of giving away your "secret sauce" is actually the strongest signal your content will work Vincent's pick for the most overrated piece of personal-brand advice, and what to do instead Chapters 00:00 The AI website that looked exactly like a stranger's 01:36 Preaching to three hundred people every Sunday 02:27 Why the big church pastor job is the hardest communication job there is 04:15 The framework that meant he never had to memorize 08:50 What almost every CEO gets wrong on stage 10:36 Why a speaking coach became the infographics guy 14:03 The $500 offer that sold a hundred seats 15:02 What actually drove the demand 17:46 Are designers finished? No, the opposite 18:53 What AI cannot tell you about your own content 21:47 The argument: video or infographics 22:43 Find your top of funnel first 28:33 Saturation decides your format 29:10 The airline loyalty infographic that built a pipeline 31:22 GIFs, stills, and the end of the animation wave 38:36 The 3% save rate rule 40:11 The one thing that never goes out of style 43:26 Stop blaming the algorithm 44:41 Live mind map: how to find what to post 52:51 Go deeper until nobody else is there 55:09 What if I give away the farm 58:33 Why he posted every salary he has ever made 01:02:16 Rapid fire 01:06:29 What reputation means to Vince Pierri Guest: Vince Pierri, LinkedIn content strategist and custom infographic designer, former pastor. Find him on LinkedIn. https://www.linkedin.com/in/vincent-angelo-coach/ Host: Justin Obey, founder of Obey Creative. Obey Creative builds personal brands and communities for founder-led companies through brand strategy, video-first social media, content creation, and podcasting. https://www.linkedin.com/in/justinobey/ Show: Return on Reputation. Reputation drives everything. Without trust, building a strong business is close to impossible. The companies that lean hardest into the personal brands of their founders and their people will outperform the ones that don't. Mentioned in this episode: LinkedIn, Lovable, Canva, Notion, HubSpot, Salesforce, Microsoft, Alex Hormozi, Kevin O'Leary, Grant Cardone.
#55
August 7 · 55 min· Video
20,000 Followers. 437 Episodes. Zero Cold Pitches.
Keith Cline joined LinkedIn on December 8, 2003. He's member number 55,829. Twenty-three years later he has 20,000 followers, and almost nothing he's posted is about him. He's interviewed the CEO of Klaviyo, the co-founder of Android, and roughly 435 other founders. He built VentureFizz, the front door to Boston tech, out of a Blogger page during a recession because his recruiting business had dried up and he was bored. He hired a developer off Craigslist. Day one, a guy at Novell paid $50 to post a job, and Keith couldn't believe it was real. Then something happened that he never planned for. Once people knew he ran VentureFizz, the introductions came to him. Investors started referring founders directly. He stopped competing for search work entirely. The side project turned out to be the best business development of his career — and he built the whole thing by promoting everybody except himself. Justin and Keith get into what reputation looks like when it's built by accumulation instead of by campaign. Why VentureFizz ran eight years as a side hustle and what kept it alive when the revenue didn't justify it. The New York expansion that taught him what he isn't. What separates a real employer brand from a careers page, from a guy who's sold employer branding for seventeen years. And the question at the center of the show: if you've been on LinkedIn for 23 years and have 20,000 followers, are you behind, or is the scoreboard wrong? If you've been telling yourself you'll start posting once you have something worth saying, this one is the argument for starting anyway. WHAT YOU'LL LEARN ▸ What "building in public" looked like in 2003, before it was a phrase or a strategy ▸ Why being early to a platform matters less than you'd think in the words of someone who was ▸ How a Blogger page of copy-pasted press releases became a regional tech ecosystem's front door ▸ Why the first $50 mattered more than the money ▸ How a side project became a business development engine that ended competitive bidding ▸ Why Keith promotes everyone but himself, and what seventeen years of that has returned ▸ The difference between reputation and reach, and why founders keep confusing the two ▸ Why the New York expansion failed, and what it taught him about localized audiences ▸ What separates a real employer brand from a careers page, with HubSpot as the case study ▸ How answer engine optimization is rewriting employer branding as job seekers research in ChatGPT ▸ What 437 founder interviews taught him about preparation as a form of respect ▸ The one thing Keith says he's failing at and it's the thing this show is about CHAPTERS 00:00 Intro 01:32 437 episodes and the consistency problem 04:10 LinkedIn member #55,829 05:19 What LinkedIn actually was in 2003 08:22 "You beat me, I'm 11,263,435" 09:43 Why his feed is about everyone but him 13:09 Boston's momentum shift 18:24 From recruiting in '98 to founding Dissero 20:49 2009: the recession side project 21:48 What version one actually looked like 24:19 The first $50 job post 30:25 Eight years as a side hustle 31:56 What kept it going when nothing was working 34:25 The New York expansion that didn't work 39:48 Quality over quantity: 20,000 connections 42:00 Employer brand vs. a careers page 43:57 How job seekers search now 45:42 Who's doing it best: WHOOP 47:32 What 437 interviews teach you 52:04 Rapid fire 54:30 Where to find Keith CONNECT WITH KEITH VentureFizz: https://venturefizz.com The VentureFizz Podcast: https://venturefizz.com/podcast LinkedIn: https://linkedin.com/in/keithcline CONNECT WITH JUSTIN Obey Creative: https://obeycreative.com LinkedIn: https://www.linkedin.com/in/justinobey FREE RESOURCES ▸ The Authority Brief: https://get.obeycreative.com/newsletter If this one landed, leave a rating. It's genuinely how new founders find the show. #PersonalBranding #FounderLedMarketing #BostonTech #BuildingInPublic #LinkedInStrategy #EmployerBranding #Podcasting #StartupFounders
#54
July 16 · 38 min· Video
Why Companies Fail at Customer Engagement | Appcues CEO Ryan Barry | EP.22
SHOW DESCRIPTION 📩 Join the Friday Briefing (free newsletter): https://get.obeycreative.com/newsletter 🎙️ Free Podcast Planner GPT: https://get.obeycreative.com/podcastplanner Every company insists they're customer-obsessed. Almost none of them can point to proof beyond a slide that says so. Ryan Barry has built two companies around closing that gap. As CEO of Appcues and former CEO of Zappi, he's spent his career sitting between customers and the leadership teams trying to serve them, and he's watched most of those teams mistake activity for connection. What he's found is both simple and uncomfortable: most B2B companies aren't losing customers because of price or product. They're losing them because nobody inside the company is actually listening and the ones who still trust last-click data over what customers plainly tell them. In this episode of Return on Reputation, I had the chance to talk with Ryan Barry to dig into why brand and reputation, not lead generation, are the real long-term growth engine, and why the way you treat people still beats any technology advantage. What you'll learn in this episode: Why most companies fail at customer engagement, and what actually earns trust instead How Ryan builds credibility fast walking into a company he didn't found, without leaning on "how it worked at my last company" What self-stated attribution is, and why it beats last-click marketing data every time The real reason B2B has spent years chasing MQLs while B2C has quietly figured out brand Why SDRs are the most overrated growth tactic in SaaS right now The moment Ryan realized technology is no longer a moat, and what is The one belief every company gets dead wrong about its customers What Appcues is building right now to close the loop between customer insight and action If you're a B2B leader betting everything on the next channel or tactic while your actual customers quietly decide whether to stick around, this episode is your reset. Follow Return on Reputation on YouTube, Spotify, and Apple Podcasts so you don't miss an episode. TIMESTAMPS: 00:00 Welcome & Meeting That Stuck 01:04 Why That Run Club Meeting Mattered 03:06 Doing for the Kids Payoff 03:44 Zappi to Appcues Journey 07:59 Why Customer Engagement Fails 11:06 Trust as a New CEO 15:00 How Ryan Got the Appcues Job 17:49 Books, Podcasts & Brand Building 20:43 Authenticity Over Scripted Marketing 21:36 Personal Brand Shows Up in Person 22:05 Consumer Insights Meet AI 23:41 LLMs and Attribution Shift 25:57 Emotion Is the Real Moat 27:38 Brand Beats Demand Gen 31:13 AI Hype vs Real Differentiation 32:59 Curiosity as a Career Skill 34:35 Rapid Fire Round 36:23 Appcues' Recommendation Loop 37:21 Where to Find Ryan Barry 37:30 Closing Thoughts & Baseball Life
#53
July 9 · 51 min· Video
Answer Engine Optimization (AEO): How to Boost Your AI Search Visibility | Ep. 21
Subscribe to the weekly Authority Brief: https://get.obeycreative.com/newsletter The search landscape is undergoing a massive shift. While most businesses still focus on traditional Google rankings, your next customer is likely asking ChatGPT, Gemini, or Claude who to trust. This new era of AI search demands a proactive approach to AI-driven reputation marketing to ensure your business is the one being recommended. In this episode of Return on Reputation, I’m joined by Tim Harvey, founder of FlyDragon. We dive into the world of Answer Engine Optimization (AEO) and how businesses can strengthen their "digital entity" to secure AI recommendations. If you aren't visible to AI, you're invisible to the future of discovery. Tim spent seven years helping top-producing real estate agents win online through websites, Google, PPC, Google Business Profile, Facebook Ads, and reviews. Then he noticed something that changed the whole playbook. AI tools were no longer just sending people back to Google. They were recommending actual names. We talk about what happens when ChatGPT, Gemini, Claude, Perplexity, and Google AI Overviews become part of how people choose a real estate agent, advisor, contractor, agency, or software company. Tim explains why AI should be treated as a marketing channel now, not later, and why FlyDragon’s research found that 91% of real estate agents are invisible to AI Search. We also get into your “digital entity,” the public footprint AI uses to understand who you are, what you do, who you help, and whether you’re credible. Your website matters. But so do reviews, listicles, directories, press releases, podcasts, Reddit threads, YouTube, LinkedIn, and third-party mentions. Because AI looks for corroboration. It wants to see if the story you tell about yourself shows up anywhere else. And if it doesn’t, there’s a good chance it recommends someone else. In this episode, we cover: Why AI Search is becoming a real marketing channel How ChatGPT is changing customer research What it means to be invisible to AI Search Why 91% of real estate agents are not showing up in AI answers How AI decides which businesses to trust Why reviews, listicles, press releases, and Reddit matter How to audit your AI presence like a customer would Why reputation is becoming machine-readable Keywords: Tim Harvey, FlyDragon, Return on Reputation, AI Search, AI visibility, Answer Engine Optimization, AEO, GEO, AI SEO, ChatGPT recommendations, Google AI Overviews, real estate marketing, digital reputation, reputation marketing, SEO, local SEO, AI marketing, founder visibility, listicles, reviews, press releases, digital entity, AI referrals TIMESTAMPS: 00:00 Introductions 00:31 From Curator to FlyDragon 02:25 AI Visibility Explained 04:58 Why People Trust AI 10:05 The 91 Percent Invisible Stat 12:34 AI Search Traffic and Overviews 16:21 Digital Entity and Data Sources 18:44 Auditing Your AI Presence 23:27 How AI Chooses Who to Trust 25:35 Listicles and Omnipresence 26:52 Diversify Reviews Everywhere 27:57 Top AI Visibility Factors 28:47 Reverse Engineer Citations 30:08 Pages vs Blogs Strategy 31:58 Audit Profiles Like SEO 33:38 Zero Click Leads Explained 35:33 Websites For AI Eyeballs 38:52 Press Releases Pay To Play 41:12 Flexible Playbook Reddit Seeding 43:34 Ethics And Gaming The System 45:06 Rapid Fire And Wrap Up
#52
July 2 · 47 min· Video
Why Trusted Brands Always Win the Downturn | Chris Farris, Boost Promotions | Ep. 20
Most founders think branded merch is a waste of money. Chris Farris has spent 20-plus years proving the opposite. In this episode of Return on Reputation, host Justin Obey and Chris Farris, founder of Boost Promotions, break down how branded merchandise becomes physical proof of a company's reputation, why trusted brands rise while commodities get cut in a downturn, and how a $100 gift can open the door to a million-dollar deal. This one is for founders who already believe personal brand and reputation are real assets, and want to know where physical brand experience fits alongside content and personal branding. What you'll learn: Why "free stuff" fails and what gives merch intention instead The real size of the branded merchandise industry and why nobody talks about it How trusted brands like Coca-Cola and Procter and Gamble win when the economy turns The gift-based demand gen math: spending $100 to close a million-dollar deal Why the unboxing "Christmas morning" moment is what people actually remember How merch acts as physical authority on top of the awareness your content builds Where founders waste the most money on branded merch, and how to stop Chapters: 00:00 Intro and Chris's path from the Mets to Boost Promotions 02:06 Is branded merch a waste of money? 04:07 How big the merch industry really is 06:06 Giving merch intention (not car-wash rags) 08:45 Beyond acquisition: recruiting, retention, impulse 10:50 What brand means today 12:56 Where companies waste money 16:14 Quality vs. brand name, staying on trend 19:45 Should founders only wear their own merch? 21:38 The process: swag closets, pop-up shops, custom products 27:00 Gift giving and demand gen: $100 to a $1M deal 30:02 The unboxing experience that gets remembered 31:25 Measuring brand and surviving the downturn 34:47 Trust is everything 36:13 Can merch build authority? Physical authority 37:36 Rapid fire 41:46 Where to find Chris and Boost Promotions
#51
June 26 · 52 min· Video
Why Your LinkedIn Profile Is the New Landing Page | Michael Kurson, FirstTouch | Ep. 19
Can you build a B2B pipeline on LinkedIn with no ad spend, no cold calls, and no cold emails? Michael Kurson did exactly that, and he tracked every step. Michael is the co-founder of FirstTouch, a platform that turns LinkedIn into a measurable go-to-market channel by attributing every comment, connection, and DM back to HubSpot. Before tech he sold something harder to move: hard seltzer, one three-hour liquor-store tasting at a time. He joins Justin Obey on Return on Reputation to explain why trust is the real product now, why the people are the brand, and how to earn attention on social before a buyer ever needs you. This conversation is for founders, sales leaders, and marketers who believe what we believe: people buy from people they know, like, and trust, and the companies that lean into the personal brands of their founders and their team will outperform the ones hiding behind a logo. What you'll learn: Why "digital eye contact" in the comments beats cold outreach every time The exact commenting routine that tripled his connection-accept rate (from ~20% to 60%+) Why your profile is the new landing page, and the website is not where buyers live anymore How AI search (AEO) is changing discovery, and the best question to ask in a first call Why AI-generated comments quietly damage your reputation How the people, not the logo, became the brand (Lovable, Clay, Whisperflow) Questions answered in this episode: How do you build trust on LinkedIn without being salesy? What is the highest-ROI activity on LinkedIn for a busy founder? Is cold calling and cold email dead in 2026? How do you make LinkedIn drive measurable pipeline? What does reputation actually mean for a B2B company today? Chapters 0:00 Cold open 0:25 From hard seltzer to software: what selling drinks taught him about trust 4:30 The trust gap in the age of AI 7:45 Micro-conversations and "digital eye contact" in the comments 11:30 Talk less, win more: the 49% talk-rate rule 14:00 Why almost nobody comments (and why that's the opening) 16:00 What FirstTouch does: making LinkedIn measurable 20:30 The anatomy of a comment that works 25:00 Your profile is the new landing page 27:30 Social as the new battleground, and AEO 33:30 Human-in-the-loop vs automation 38:00 67% attribution: when the light bulb goes on 42:30 The people are the brand (Lovable, Clay, Whisperflow) 46:45 If a busy founder had 8 minutes a day 48:45 "LinkedIn is cringe" and the perfect-post trap 49:40 If you're not on social, you disappear 51:25 Rapid fire 53:55 What reputation means
#50
June 19 · 40 min· Video
Why Human Authenticity Is the New Competitive Advantage | Ep. 18 with Jon Dick
📩 Subscribe to our newsletter the Authority Brief: https://get.obeycreative.com/newsletter 🎙️ Free Podcast Planner GPT: https://get.obeycreative.com/podcastplanner Most companies are trying to figure out what AI is going to change. Jon Dick thinks the better question is what AI won’t change. In this episode of Return on Reputation, Justin Obey talks with Jon Dick, Chief Customer Officer at HubSpot about inbound marketing, AI, personal brand, Answer Engine Optimization, and why human authenticity may become one of the strongest advantages a company can build. Jon has spent years inside HubSpot, a company that helped define inbound marketing and the idea of giving value before asking for anything back. Free content. Free tools. Useful education. The kind of work that compounds slowly, then suddenly looks obvious. But AI is changing the rules. Content is easier to make now. Code is easier to ship. Answers are easier to generate. Which sounds great, until every company starts sounding the same. Jon argues that the brands that break through will be the ones with a real point of view. Not louder content. Not more content. Better thinking. Clear opinions. Real people behind the message. We talk about why being opinionated matters, why “AI for AI’s sake” usually misses the point, and how companies can use AI to speed up human ideas without losing the voice that made those ideas worth sharing in the first place. Jon also explains how HubSpot is thinking about agentic customer platforms, what AEO means for the future of search, and why the old marketing funnel feels less useful than it used to. The buyer journey is messier now. More indirect. Harder to track. Maybe that’s uncomfortable for marketers who want clean attribution. But it’s also closer to how people actually buy. We also get into thought leadership, LinkedIn, community, customer trust, and one very old-school tactic that may be working better than ever: picking up the phone. In this episode we cover: Why human authenticity matters more in the AI era How AI is changing inbound marketing and go-to-market strategy Why brands need stronger opinions to stand out The difference between AI output and real business outcomes What “add value before you extract value” means at HubSpot How Jon thinks about AI agents and customer context Why Answer Engine Optimization matters for modern search Why the traditional funnel no longer explains how people buy How leaders can build trust through public, honest engagement Why generic AI content makes real human voice more valuable How AI can help with content without replacing the person behind it Why attribution is getting harder, and why that might be okay What marketers should understand about community and social proof Why picking up the phone still works Keywords: Jon Dick, HubSpot, Return on Reputation, AI marketing, inbound marketing, human authenticity, Answer Engine Optimization, AEO, go-to-market strategy, thought leadership, personal brand, AI agents, customer platform, B2B marketing, brand reputation, content strategy, LinkedIn marketing, reputation marketing
#49
June 12 · 57 min· Video
How to Turn a Founder’s Vision Into a Message That Sells | Shannon Curran | Ep. 17
📩 Subscribe to our newsletter the Authority Brief: https://get.obeycreative.com/newsletter 🎙️ Free Podcast Planner GPT: https://get.obeycreative.com/podcastplanner Most early-stage founders think they have a marketing problem. But sometimes the real problem is simpler: the founder can sell the vision in a conversation, but the company cannot explain it clearly anywhere else. In this episode of Return on Reputation, my guest is Shannon Curran, founder of SSC Consulting, a fractional CMO and go-to-market advisor helping early-stage B2B SaaS companies turn founder insight into clear positioning, stronger messaging, and a more repeatable path to growth. Shannon has spent her career in marketing, tech, venture capital, and executive advisory roles. After working as a VP of Marketing and advising portfolio companies from the VC side, she started SSC Consulting in 2024 after returning from maternity leave, looking at her five-month-old son, and realizing it might be time to bet on herself. We talk about what happens when a founder has the charisma, conviction, and clarity to close deals, but that same energy gets trapped in one-on-one calls, investor meetings, or internal conversations. Shannon breaks down how she helps founders extract their point of view, sharpen their positioning, align their teams, and build a go-to-market message that actually helps the company sell, grow, and stand out. We also talk about what it’s really like to start a consulting business, how founder brand is different from actual go-to-market strategy, and why so many B2B startups struggle to make their message more specific. In this episode we cover: Why founder charisma often does not translate into clear company messaging How to turn a founder’s point of view into a repeatable go-to-market strategy Why early-stage B2B SaaS companies struggle with positioning The difference between founder brand and just posting on LinkedIn How Shannon interviews founders, teams, investors, and customers to build better messaging Why recently onboarded customers are often the best source of positioning insight How scarcity mindset leads founders to say yes to the wrong customers Why narrowing your message can actually help you grow faster What B2B buyers are really looking for in 2026 How personal brand, LinkedIn, and podcasting support reputation and inbound growth Keywords: founder messaging, B2B SaaS marketing, go-to-market strategy, founder brand, positioning strategy, fractional CMO, B2B marketing, LinkedIn personal brand, early-stage SaaS, Return on Reputation podcast
#48
June 9 · 49 min· Video
What Investors Actually Look For Before They Ever Take Your Pitch with David Brown | Ep 16
📩 Subscribe to our newsletter the Authority Brief: https://get.obeycreative.com/newsletter 🎙️ Free Podcast Planner GPT: https://get.obeycreative.com/podcastplanner David Brown has seen thousands of pitches. He funds very few of them. Not because the ideas are bad. Because the founders haven't done the work of being known, trusted, or differentiated before they walk into the room. David is the founder of Impellent Ventures, a pre-seed and seed stage fund backing founders in underserved ecosystems across upstate New York and the Rust Belt. Before that, he built TUGG, Technology Underwriting Greater Good, into one of Boston's most influential startup communities, putting 14,000 people a year through events and millions of dollars into early-stage companies. He's spent his career betting on founders before anyone else does. And he has a clear point of view on what separates those who make it from those who don't. In this episode of Return on Reputation, we cover: — Why 90% of pitches get ignored and what actually gets an investor's attention — The three things David looks for in a founder above everything else — Why the VC relationship lasts longer than most American marriages — What personal brand gets wrong and what it looks like when it's done right — How to get warm introductions in a world where cold outreach is dying — The one habit David says most founders and investors forget about — What reputation really means after twenty years of betting on people This one is for the founders who are building something real and wondering why the right people haven't found them yet. Chapters: 00:00 Introduction 02:10 TUGG and the Boston startup era 06:35 Why David moved back to Rochester and started Impellent 11:05 The Impellent thesis: supercharging startups in underserved markets 17:13 What investors actually evaluate in a founder 23:00 The VC relationship is longer than a marriage 25:19 Personal brand vs. vanity brand — where founders get it wrong 29:00 AI in the pitch process and portfolio companies 40:35 How founders should build authority to get in front of investors 43:30 The biggest mistake founders make 45:15 Rapid fire 48:05 What reputation means today Subscribe to Return on Reputation on YouTube, Apple Podcasts, and Spotify. Ready to close your Authority Gap? Visit OBEYCreative.com
#47
May 28 · 54 min· Video
Why Clear Positioning Is the #1 Driver of B2B Business Growth | Anthony Pierri | Ep. 15
📩 Join the Friday Briefing (free newsletter): https://get.obeycreative.com/newsletter 🎙️ Free Podcast Planner GPT: https://get.obeycreative.com/podcastplanner Every B2B company says they have a positioning strategy. Almost none of them can explain what they actually do in one sentence. Anthony Pierri has seen this up close, hundreds of times. As co-founder of Fletch PMM, he's spent the last three years sitting with founders and leadership teams, staring at homepages that say everything and mean nothing. Not the pitch deck. Not the brand guidelines. The actual words a stranger reads when they land on your site and decide in seconds whether you're worth their time. What he's found is both simple and uncomfortable: most B2B companies aren't struggling because of their product. They're struggling because nobody, including their own team, can agree on who they're really for. In this episode of Return on Reputation, I had the chance to talk with Anthony Pierri to dig into why clear positioning is the #1 driver of B2B growth and why the homepage is the most underrated alignment tool in any company's arsenal. What you'll learn in this episode: Why your homepage isn't a marketing asset. It's a forcing function for internal alignment The difference between firmographic ICPs and Jobs-to-be-Done segmentation, and why one of them actually works The real reason B2B companies end up with 20 use cases and no clear message The trucking software company that was weeks away from dying until one positioning bet changed everything Why sharing everything you know publicly doesn't cost you clients. It brings them in The two content principles Anthony uses to build authority on LinkedIn: the spiky opinion and the super specific how Why the champion in a B2B deal is almost never who you think it is What Stripe, Calendly, and Vanta can teach any startup about winning a market If you're a B2B founder who's invisible outside your inner circle, great at what you do but unknown everywhere else, this episode is your roadmap. Follow Return on Reputation on YouTube, Spotify, and Apple Podcasts so you don't miss an episode. TIMESTAMPS: 00:00 Meet Anthony Pierri of Fletch PMM 00:50 From Pastor to Product Marketer 03:04 What a Failed Sales Role Taught Him 04:59 How His First LinkedIn Post Went Viral 08:18 Your Homepage Is a Positioning Tool, Not a Marketing Asset 10:33 The Trucking Company That Almost Died 12:37 Why Niching Down Is Not About Firmographics 16:18 The Risk of Public Teardowns 18:11 Why B2B Websites Get Vague 23:04 How to Prioritize Your Homepage 25:49 Why Changing Market Perception Takes Time 27:09 Building a 90% Inbound Business With No Outbound 27:18 How LinkedIn Became His #1 Inbound Channel 29:25 Why Sharing Everything Publicly Wins More Clients 31:27 Will AI Kill the Case for Public Content 34:21 Why the Champion Is Never the C-Suite 38:23 The Authority Gap Every B2B Founder Has 44:37 How to Build Organic Distribution as a Founder 47:36 The Two Content Principles Behind Every B2B Thought Leader 49:49 Rapid Fire and Wrap
#46
May 21 · 52 min· Video
Why Waiting to Build Your Personal Brand Is Costing You Millions | Alexandra Crabb | Ep. 14
📩 Join the Friday Briefing (free newsletter): https://get.obeycreative.com/newsletter 🎙️ Free Podcast Planner GPT: https://get.obeycreative.com/podcastplanner Alexandra Crabb just became the owner of a 28-year-old PR agency. She didn't start it. She grew it from the inside over 14 years — joined as VP when the team was five people, helped build it to ten, and six weeks ago acquired Castor Communications from its founder, Kimberly Lancaster. Now she's thinking about something most founders never stop to consider: legacy. What does she want to leave behind? And how does she protect the reputation that was already there when she walked in? That question runs through everything in this episode. Alex has spent her entire career making founders visible — getting them in front of the right journalists, the right audiences, the right rooms. And she has a clear, honest take on where founders waste money, where they miss the window, and why the ones who wait until they "need" PR are already behind. In this episode of Return on Reputation, we cover: — What PR actually does for a B2B founder — and what it absolutely cannot do — Why founders who wait to build their personal brand make their own lives harder — The real cost of staying invisible while someone louder takes your market — How AI is reshaping discoverability and why earned media now carries more weight than ever — The owned, earned, and paid flywheel and how to think about the right ratios — Why your whole team needs to be visible, not just the founder — What "building in public" actually looks like when you're still figuring it out — The AEO vs. GEO debate and why the fundamentals still win This one is for the founder who's heads down building and hasn't looked up to ask who knows they exist yet. Chapters: 00:00 Introduction 00:44 Alex acquires Castor Communications — the intrapreneurship story 04:45 The weight of ownership — legacy, pressure, and not screwing it up 05:35 AI and the future of discoverability — how Castor is adapting 11:10 The Wild West of social media and why LinkedIn still wins for B2B 13:45 What PR actually does for a B2B founder — and what founders get wrong 16:00 It's not magic: why PR doesn't work as an on/off switch 18:05 When a startup is NOT ready for PR 20:25 Building your personal brand before you need it — and what waiting costs 25:10 The loudest person in the room problem 27:00 Media training, story development, and the living pitch book 33:00 AEO, GEO, and the shift in how people find you 38:35 Why owned + earned + paid all work together 43:00 The whole team needs to be visible — not just the founder 49:05 AEO — the one thing every founder needs to understand right now 51:05 Rapid fire 57:10 What reputation means to Alex today — and why she's thinking about legacy Subscribe to Return on Reputation on YouTube, Apple Podcasts, and Spotify. Ready to close your Authority Gap? Visit OBEYCreative.com
#45
May 14 · 48 min· Video
AI Won't Replace You — But This Skill Gap Will | Mamoon Chowdry | Ep. 13
📩 Join the Friday Briefing (free newsletter): https://get.obeycreative.com/newsletter 🎙️ Free Podcast Planner GPT: https://get.obeycreative.com/podcastplanner ⬇️ Download the Authority Blueprint: https://get.obeycreative.com/mediaengineblueprint 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
#44
May 8 · 40 min· Video
Why 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?
#43
April 30 · 53 min· Video
He 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

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