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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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#57
August 20 · 48 min
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
#42
April 23 · 1 hr
His 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
#41
April 16 · 48 min
He 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
#40
April 9 · 50 min
Show 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
#39
April 2 · 51 min
Reputation 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
S1 · E38
March 26 · 48 min
The 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

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