Who Got Me Here

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 Moore 01:15 — Dial-up modems, AOL, and a house that valued tinkering 02:30 — Tony Luke’s: building the coolest cheesesteak website you’ve ever seen 03:45 — Skipping a summer at Wawa: his first web design agency 04:52 — Princeton and “financial engineering” 06:10 — Insight Partners: 100 cold calls a week, one deal a year 07:06 — Ryan Hinkle and Deven Parekh 09:05 — His class at Insight, and meeting Jake Stein on day one 11:30 — College FOMO and Yes Letter 12:08— The Moraculator: poker odds and product-market fit 14:36 — A.J. Khubani and the As Seen on TV playbook 16:14— The Spill Bullet and a spring break in Chinese factories 17:30 — The Sharper Image, and why software beat hardware 19:12 — Golden handcuffs: deciding to leave Insight 21:42 — Quitting on Friday, Lehman collapses on Saturday 23:02 — Spinning Stitch out of the Magento deal 24:51 — The “Triple Lindy” and Bob’s weekly call with Jake 26:10 — Watching a rival sell for $2.6 billion 27:15 — When your biggest rival becomes your first partner 28:30 — The origin of Crossbeam: a data standoff between partners 32:06 — Solving the cold start problem with your network 33:00 — $3.5 million on a PowerPoint deck in a week 34:04 — Creating the ecosystem-led growth category 35:45 — AI, MCP, and agents that need permission to share 38:10 — 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.com Time stamps: 00:00 — Introducing Joe Chernov 00:40 — Ninth grade, his mother, and Lech Wałęsa 02:40 — Door-to-door with a writing sample → the PR firm 03:30 — “Clean my desk” — the real interview 04:15 — “You just wanna be somebody that’s easy to root for” 04:50 — Brian Kardon: a big budget and a long leash 06:30 — Fred Shilmover: “You belong in the room” 07:40 — Leslie Bradshaw and the Jagger–Richards partnership 09:00 — Mike Volpe: holding an idea against a bigger frame 10:40 — Hillá Watkins: “You put a ceiling over my head” 12:50 — How to break through a wall: you can’t see around corners 15:15 — Beginner’s mind, metaphors, and being your own audience 17:30 — The social media book, Joe Payne, and the Dreamforce session 20:20 — The Hero Grill: creativity applied to friendship 21:50 — Ghosted, then called back — putting ego aside 23:00 — “Why do you spend time with people who can’t help you?” 24:30 — Personal brand and the Leonard Cohen test 25:50 — Make your strengths undeniable / the question beneath the question 28:20 — Battery Ventures: the fountain of youth is learning 30:50 — 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.com Timestamps: 00:00 – Introduction: Why teaching networking matters 02:49 – Networking is a skill schools rarely teach 05:07 – The childhood lesson that shaped Rebecca’s mindset 08:33 – Talent is everywhere, opportunity is not 10:05 – The student who changed everything 11:51 – Founding a high school at age 25 14:28 – The mentor who taught her how to lead 17:09 – How networking opened the next chapter of her career 19:07 – Why apprenticeships are so powerful 21:47 – Rethinking how students access opportunity 25:27 – Teaching the hidden language of networking 27:26 – Helping students overcome fear and self-doubt 30:11 – Why most adults actually want to help 34:24 – 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.com Time Stamps: 00:00 – A Defining Moment: Feeling Seen for the First Time 02:20 – Growing Up with Instability 04:20 – How High Expectations Shape Young Minds 07:00 – Finding Role Models When Few Exist 09:00 – Identity, Confidence, and Being “The Collar Boys” 12:00 – Teachers Who Change Trajectories 15:30 – Purpose Through Service: Building Mentorship Programs 18:00 – Investing in Youth: Why Developing the Next Generation Matters 21:30 – Joining Weave and Building Community Trust 23:30 – The “Weavers” of America 25:00 – Volunteering vs. Weaving: Building Relationships 27:00 – What Thriving Communities Look Like for Young Boys 29:00 – Can Strong Communities Be Built at Scale? 30:30 – How Relationships Are Built in Everyday Life 32:00 – Learning to Be Honest and Kind to Yourself 34:30 – The Power of One Person Reaching Out 36:00 – Advice to His 12-Year-Old Self 37:30 – The Mentors Who Still Shape Him Today 38:30 – Networking as Humanity: Treating Everyone with Equal Dignity 39:30 – 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.com Time Stamps: 00:00 – An Unlikely Beginning 03:00 – Leadership Is a People Business 04:30 – The Pivot from Scholar to Builder 07:00 – Breaking Academic Silos 10:30 – Why Relationships Still Matter (Especially in a Digital World) 13:50 – The Real Power of Business School Networks 17:52 – AI Comes To Campus 18:50 – Responsible AI and the Hard Questions 22:10 – Designing Curriculum at “Vertical” Speed 24:30 – Your Bain on ChatGPT 28:05 – Admissions In The Age of AI 29:40 – 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