Bob Moore: You Never Really Start From Nothing

As a new grad, Bill Macaitis asked a departing colleague at his last-day lunch for the best advice he had. The answer: don’t focus on being employed; focus on being employable. Bill has been acting on it ever since.He taught himself SEO when there were no classes for it. Those skills helped grow Fox Interactive Media into the third-largest web network in the world, and then got him hired at Salesforce, where Marc Benioff wanted to rank number one for “CRM.” He went on to be CMO of Zendesk through its IPO and CMO of Slack during its hypergrowth years. He was also my boss at Salesforce, and he’s the person I’ve called for career advice ever since.This conversation is about the people behind that run: Benioff taking a meeting from a TV screen in a Hawaiian shirt, Mikkel Svane talking him into “beautifully simple,” and Stewart Butterfield judging restaurants by the valet. Bill also talks about the back channels that opened doors he never knew about, and why he always takes the recruiter’s call.Then he gets practical: the two questions he’d ask in any job interview, and what he’d teach himself if he were 25 today. His answer is how to build and govern teams of AI agents, the SEO of this moment.Time stamps:00:00 — Introducing Bill Macaitis01:15 — The advice that shaped his career: Be employable, not employed03:00 — Teaching himself SEO, from Rotten Tomatoes to Fox Interactive Media05:15 — Kendall Collins, Clarence So, and bringing B2C DNA to Salesforce07:45 — Marc Benioff, a Hawaiian shirt, and the “social enterprise” homepage test10:50 — Data over the HiPPO (highest-paid person’s opinion), with George Hu as an ally13:10 — Mikkel Svane and “beautifully simple” at Zendesk15:00 — Back channels: how the people who vouch for you open doors you never see17:20 — Joining Slack early, and why he always takes the recruiter’s call19:30 — Stewart Butterfield’s restaurant test: the brand is every micro-experience21:30 — Hypergrowth at Slack: the week-off DAU bet and protecting culture23:50 — Fair billing, freemium, and a 10-million-person marketing team25:50 — Advising AI companies, and what he saw in Turing’s Jonathan Siddharth28:50 — How to find the right company and make yourself stand out30:30 — The two questions to ask in any interview: growth and NPS31:30 — The next SEO: Building agentic systems and staying employable33:00 — Lightning round: The Lord of the Rings and what “Who Got Me Here” meansWho ese got Bill here:Andrew Braccia, Richard Jalichandra, Bruce Campbell, Colin Fleming, Adam Greco, Maggie Hott, Mark Jung, Michael Lynch, Brad Morris, Jamie Rosenfield, Bill Shaw, Jonathan Siddharth, Kraig Swensrud, AJ Tennant, Lauren VaccarelloThree Important Takeaways#1 Be Employable, Not Just Employed: Teach Yourself the Skill Nobody Has Yet Bill’s first job out of college was at System Software Associates, an early ERP company in Chicago. Whenever someone left, the team took them to a last-day lunch, and Bill, the new guy, would ask the person leaving for their best piece of advice. One of them told him: “Don’t overly focus just on being employed. Focus on being employable.” Bill took it literally. When SEO was new and there were no classes for it, he read every forum and went to every conference he could. That skill helped grow Fox Interactive Media into the third-largest network of sites in the world. It’s also part of why Salesforce brought him in, when Marc Benioff wanted to rank number one for “CRM.”Takeaway: Your job can go away. Your skills can’t. Find the thing nobody in the room knows how to do yet and teach yourself. Bill’s answer for today is learning to build and govern teams of AI agents, the SEO of this moment.#2 The Back Channels Are Always Running: Be Worth Vouching For Bill didn’t know his former IGN CEO, Mark Jung, had told a headhunter “this guy really likes you” until the Zendesk role showed up. When he went to Salesforce, Richard Jalichandra, a former IGN colleague, turned out to be friends with Kendall Collins and vouched for him. Slack came through Accel’s talent team. For years, Bill had taken recruiters’ calls even when he was happy where he was, just to ask, “How can I help you out?” When the right opportunity came up, his name surfaced. Takeaway: Someone is talking about you in a room you’ll never see. Do work people are proud to recommend, take the recruiter’s call when you don’t need it, and help them anyway. Those back channels can define a career.#3 Ask Two Questions Before You Take the Job Bill calls your next job one of the biggest decisions of your life. Yet he’s watched people take one because it pays 15% more or is closer to home. If he could ask only two questions in an interview: What’s your year-over-year revenue growth? What’s your net promoter score? If they don’t know what NPS is, that’s not a good sign. If growth is in the triple digits and NPS is in the 80s or 90s, go for it. “It’s not fun when you work for a company where people hate the product.”Takeaway: Looking for a job is a full-time job. Back-channel the company as hard as they back-channel you, and pick growth and customer love over a bump in pay. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit whogotmehere.substack.com

Bob Moore has sold two software companies and raised more than $100 million for a third. So how did he get here? Like most entrepreneurs, he got his start when someone gave him a chance. For Bob it was a neighbor who owned Tony Luke’s, the Philly cheesesteak shop, and paid a seventh grader a couple hundred bucks to build its website. That turned into a high school web design business. At Princeton he ran three businesses at once, each with very different business models. None became a huge hit, but they forged him into an entrepreneur. Right after college he joined Insight Partners, where he learned what investors look for in software companies and made friendships that have lasted his whole career.Being an entrepreneur can be humbling, and luck plays a bigger role than most people admit. Bob and his co-founder, Jake Stein, quit their jobs to start RJMetrics on a Friday, and Lehman Brothers collapsed the next day. They kept at it and sold RJMetrics to Magento, a real win. Then Looker, the rival that had beaten them in head-to-head deals, sold to Google for $2.6 billion. As Bob puts it, “your $100 million rounding error was greater than the amount that we sold RJMetrics for.”Bob didn’t stop. Each company fed the next. Raising money got easier, and so did finding early customers: Crossbeam’s first three were companies he had already built or worked with. His story shows how relationship capital and the entrepreneurial spirit compound over time, as long as you have grit, stay humble, and keep going.www.whogotmehere.comTime stamps:00:00 — Introducing Bob Moore01:15 — Dial-up modems, AOL, and a house that valued tinkering02:30 — Tony Luke’s: building the coolest cheesesteak website you’ve ever seen03:45 — Skipping a summer at Wawa: his first web design agency04:52 — Princeton and “financial engineering”06:10 — Insight Partners: 100 cold calls a week, one deal a year07:06 — Ryan Hinkle and Deven Parekh09:05 — His class at Insight, and meeting Jake Stein on day one11:30 — College FOMO and Yes Letter12:08— The Moraculator: poker odds and product-market fit14:36 — A.J. Khubani and the As Seen on TV playbook16:14— The Spill Bullet and a spring break in Chinese factories17:30 — The Sharper Image, and why software beat hardware19:12 — Golden handcuffs: deciding to leave Insight21:42 — Quitting on Friday, Lehman collapses on Saturday23:02 — Spinning Stitch out of the Magento deal24:51 — The “Triple Lindy” and Bob’s weekly call with Jake26:10 — Watching a rival sell for $2.6 billion27:15 — When your biggest rival becomes your first partner28:30 — The origin of Crossbeam: a data standoff between partners32:06 — Solving the cold start problem with your network33:00 — $3.5 million on a PowerPoint deck in a week34:04 — Creating the ecosystem-led growth category35:45 — AI, MCP, and agents that need permission to share38:10 — Closing This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit whogotmehere.substack.com

Joe Chernov has two IPOs behind him, three CMO seats on his resume, and a job at Battery Ventures — and none of it started with a business degree. It started with his mother, in ninth grade, asking him whether he was going to be a follower his whole life or just for one more day. In this episode of Who Got Me Here, Joe traces a career built on other people betting on him before the credentials caught up: the PR-firm founder who hired him off a party conversation about books and then handed him a can of WD-40 and had him clean the desks; Brian Kardon, who ghosted him after showing him his future desk and then called back eleven months later to say he’d made a mistake; and Fred Shilmover, who pulled him aside at InsightSquared and said, “you think you don’t belong in the room, but you belong in the room.”The line at the center of the conversation is Joe’s own: “You just wanna be somebody that’s easy to root for.” Around it he tells the story of Hillá Watkins, who opened their very first phone call with “I don’t think we should hire you. You put a ceiling over my head,” and who is now one of his closest friends; of Leslie Bradshaw, the creative partner he describes in Jagger-and-Richards terms; and of the day his wife asked why he spent so much time with people who couldn’t help him — a question that got answered years later, when his career hit a wall and those same people showed up. It’s a conversation about humility as an actual career strategy, about why not knowing turned out to be his advantage, and about the fact that you can’t see around corners, so you may as well be the one who changes first.www.whogotmehere.comTime stamps:00:00 — Introducing Joe Chernov00:40 — Ninth grade, his mother, and Lech Wałęsa02:40 — Door-to-door with a writing sample → the PR firm03:30 — “Clean my desk” — the real interview04:15 — “You just wanna be somebody that’s easy to root for”04:50 — Brian Kardon: a big budget and a long leash06:30 — Fred Shilmover: “You belong in the room”07:40 — Leslie Bradshaw and the Jagger–Richards partnership09:00 — Mike Volpe: holding an idea against a bigger frame10:40 — Hillá Watkins: “You put a ceiling over my head”12:50 — How to break through a wall: you can’t see around corners15:15 — Beginner’s mind, metaphors, and being your own audience17:30 — The social media book, Joe Payne, and the Dreamforce session20:20 — The Hero Grill: creativity applied to friendship21:50 — Ghosted, then called back — putting ego aside23:00 — “Why do you spend time with people who can’t help you?”24:30 — Personal brand and the Leonard Cohen test25:50 — Make your strengths undeniable / the question beneath the question28:20 — Battery Ventures: the fountain of youth is learning30:50 — Lightning round — Joe reacts to his own most-quoted lines This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit whogotmehere.substack.com

Rebecca Agostino is an entrepreneur in the world of education, and she’s on a mission to teach the next generation how to build the relationships and durable skills that power career transitions. She has served with Teach for America, helped scale edtech platforms, and at just 25 years old became the founding principal of Freedom Prep High School in Camden, New Jersey. Today, through her company Prentice, she is tackling a gap almost no one is addressing head-on. Networking is one of the most important skills in modern life, and it isn’t taught in school.In this conversation, Rebecca shares the truth that quietly shapes every career: the best opportunities are almost never found through job boards or career fairs. They come from people — a warm introduction, a follow-up email, a thoughtful question, a hand raised in a room. She walks through how she breaks networking into micro skills for teenagers: how to map the 25 people you already know, how to write the email, how to follow up without nagging, and how to turn a single conversation into a job shadow, a referral, or a mentor.It is a conversation about agency, self-advocacy, and the quiet truth that most of us got our foot in the door because someone gave us a shot. Rebecca’s work is making sure the next generation knows how to ask for that shot — and how to be ready when it comes.www.whogotmehere.comTimestamps:00:00 – Introduction: Why teaching networking matters02:49 – Networking is a skill schools rarely teach05:07 – The childhood lesson that shaped Rebecca’s mindset08:33 – Talent is everywhere, opportunity is not10:05 – The student who changed everything11:51 – Founding a high school at age 2514:28 – The mentor who taught her how to lead17:09 – How networking opened the next chapter of her career19:07 – Why apprenticeships are so powerful21:47 – Rethinking how students access opportunity25:27 – Teaching the hidden language of networking27:26 – Helping students overcome fear and self-doubt30:11 – Why most adults actually want to help34:24 – Rebecca’s advice for young people This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit whogotmehere.substack.com

Frederick Riley grew up in Saginaw, Michigan surrounded by eviction notices, food insecurity, and the constant feeling that something might go wrong at any moment. Yet his story is ultimately one of possibility. Along the way, a remarkable network of people — a determined mother, a pastor, a principal, teachers, mentors, and neighbors — helped shape the path that would eventually lead him to become Executive Director of Weave: The Social Fabric Project at the Aspen Institute.In this deeply personal conversation, Fred reflects on the moment he met his father for the first time at age eleven, the mentors who helped him see a bigger future, and the painful lessons that ultimately strengthened his commitment to community and service.Fred also shares how his work today focuses on identifying and supporting “weavers,” the everyday people quietly rebuilding trust and connection in communities across America.It is a powerful reminder that none of us gets where we are alone. Our lives are shaped by the people who see us, challenge us, and lift us up along the way.www.whogotmehere.comTime Stamps:00:00 – A Defining Moment: Feeling Seen for the First Time02:20 – Growing Up with Instability04:20 – How High Expectations Shape Young Minds07:00 – Finding Role Models When Few Exist09:00 – Identity, Confidence, and Being “The Collar Boys”12:00 – Teachers Who Change Trajectories15:30 – Purpose Through Service: Building Mentorship Programs18:00 – Investing in Youth: Why Developing the Next Generation Matters21:30 – Joining Weave and Building Community Trust23:30 – The “Weavers” of America25:00 – Volunteering vs. Weaving: Building Relationships27:00 – What Thriving Communities Look Like for Young Boys29:00 – Can Strong Communities Be Built at Scale?30:30 – How Relationships Are Built in Everyday Life32:00 – Learning to Be Honest and Kind to Yourself34:30 – The Power of One Person Reaching Out36:00 – Advice to His 12-Year-Old Self37:30 – The Mentors Who Still Shape Him Today38:30 – Networking as Humanity: Treating Everyone with Equal Dignity39:30 – Three Simple Actions to Rebuild Community Today This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit whogotmehere.substack.com

Geoffrey Garrett, Dean of the Marshall School of Business at USC and former Dean of the Wharton School, has spent his career at the center of some of the world’s most respected institutions. But in this conversation, he makes a compelling case that even the most established business schools must evolve quickly to meet the demands of the AI age.From his unlikely journey growing up in Australia to teaching Rhodes Scholars at Oxford to leading at Yale, UCLA, Wharton, and now USC, Geoff reflects on the mentors, pivotal moments, and leadership lessons that shaped him. Yet the heart of this episode is his vision for the future of higher education.What does it mean to prepare students for a world of “vertical” technological change? Should admissions prioritize technical fluency? How do universities balance AI productivity with deep learning and responsible leadership? And what does “AI for X” (applying artificial intelligence across every discipline) mean for the next generation of business leaders?Geoff shares why AI literacy must become an entry condition, why distinctiveness matters more than ever in admissions, and why the real challenge isn’t adopting AI, it’s doing so responsibly.If you care about the future of business education, leadership, or the role universities will play in shaping the AI era, this conversation is for you.www.whogotmehere.comTime Stamps:00:00 – An Unlikely Beginning03:00 – Leadership Is a People Business04:30 – The Pivot from Scholar to Builder07:00 – Breaking Academic Silos10:30 – Why Relationships Still Matter (Especially in a Digital World)13:50 – The Real Power of Business School Networks17:52 – AI Comes To Campus18:50 – Responsible AI and the Hard Questions22:10 – Designing Curriculum at “Vertical” Speed24:30 – Your Bain on ChatGPT28:05 – Admissions In The Age of AI29:40 – Lightning Round This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit whogotmehere.substack.com

What if a single, well-timed email could change the trajectory of your entire career? In this episode of Who Got Me Here, Annie Riley sits down with Drew Sechrist, one of Salesforce’s earliest employees and the founder & CEO of Connect the Dots. Drew shares how a cold email to Marc Benioff landed him a front-row seat on Salesforce’s rise from pre-revenue to over $1B—and how intentional relationship-building made him a top-performing sales leader.Together, they unpack why meaningful networking isn’t about volume, how to stand out when everyone around you is an A-player, and why imposter syndrome is often a signal, not a weakness. This conversation is a masterclass in being curious, being intentional, and building relationships that compound over decades.www.whogotmehere.comTime Stamps:00:00 - Introduction to Drew Sechrist00:48 - Drew’s Early Career and Salesforce Journey01:45 - The Power of a Well-Timed Cold Email05:48 - Navigating Relationships and Networking at Salesforce08:50 - Mentorship and Early Sales Lessons16:14 - Building Community Across Geographies18:55 - Learning from Mistakes and Iterating20:18 - The Importance of Feedback in Networking23:16 - Tools for Building and Maintaining Relationships27:51 - Final Thoughts on Relationship Building This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit whogotmehere.substack.com

In this episode of Who Got Me Here, Sarah Franklin traces her path from chemical engineer to CEO—and makes a compelling case that relationships, not resumes, are what truly shape a career. Through stories of being rejected 14 times, creatively breaking into tech, and rising from individual contributor to President at Salesforce before becoming CEO of Lattice, Sarah shares how self-awareness, gratitude, and intentional networking quietly compound over time. This conversation goes beyond titles and transitions, exploring how clarity of purpose, generosity toward others, and the courage to ask for help can redefine success and unlock opportunities you can’t see looking forward—but only connect looking back.www.whogotmehere.comTime Stamps:00:00 Introduction: Why Relationships Matter02:04 Defining Fulfillment & Purpose at Work04:54 From Chemical Engineering to Tech07:58 Learning to Translate Tech for Business08:33 How Relationships Actually Create Opportunity10:00 The 14 Rejections That Changed Everything14:14 Salesforce: From IC to President16:01 Leaving, Returning, and Seeing Clearly17:33 Servant Leadership & Helping Others Rise19:08 Goal Setting That Works (V2ME Framework) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit whogotmehere.substack.com

Whitnie Narcisse has built her career around a simple but uncommon truth: the strongest companies—and the strongest careers—are built through real relationships. As a longtime operating partner at First Round Capital, she’s been a quiet force behind some of the most trusted founder and operator communities in tech.In this episode, Whitnie traces her non-linear path from Teach for America and nonprofit work into venture capital, sharing how curiosity, bold outreach, and genuine care opened doors she couldn’t have planned for. Along the way, she unpacks the mindset shifts required to navigate career transitions, advocate for yourself, and move forward—even when you don’t fit the traditional mold.We also dive into the how: practical, creative approaches to networking and mentorship that actually work. From async advice and Loom videos to game nights, curated gatherings, and her FACE framework—Facts, Authenticity, Credibility, and Engagement—Whitnie offers a masterclass in building relationships with intention and generosity.This conversation is a reminder that community isn’t built overnight. But when it’s built well, it compounds—and becomes one of the most powerful forces in a career.www.whogotmehere.comhttps://whogotmehere.substack.comTime Stamps:00:00 – Meet Whitnie Narcisse: From Teaching 8th Grade Science to Venture Capital01:00 – Saying Yes Early: Teach for America, Nonlinear Careers, and Learning by Doing02:45 – The Trivia Night That Quietly Changed Everything07:00 – Breaking Into Venture Without a Straight Line (or a Perfect Plan)09:00 – Networking with Agency: Confidence, Bold Outreach, and Assuming Positive Intent14:00 – Modern Mentorship: Loom Videos, Async Advice, and Protecting Your Time16:00 – Building Community at First Round: Why Relationships Compound Over Time18:30 – What Makes a Great Event: Guest Lists, Small Groups, and Intentional Design20:30 – Rethinking Networking: Game Nights, Poker, and Making Connection Fun22:30 – The FACE Framework: How to Be Memorable, Human, and Credible This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit whogotmehere.substack.com

Michael Palmisano didn’t stumble into success—he earned it through years of uncertainty, persistence, and an unwavering belief that the things worth having take time. In this episode of Who Got Me Here, Michael shares how the collapse of the traditional music industry forced him to rethink everything, ultimately leading him to build a global audience by teaching guitar online and breaking down songs.Guided by his mantra—working hard, getting better every day—Michael reveals how showing up authentically, being vulnerable, and embracing imperfection helped him connect with nearly a million subscribers on a deeply human level. From betting his family’s savings on an unproven idea to launching his next entrepreneurial act with Teleport pedals, this is a powerful story about patience, self-trust, and building a life around what matters most.www.whogotmehere.comhttps://whogotmehere.substack.comhttps://www.youtube.com/@whogotmehere-podcast This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit whogotmehere.substack.com