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

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.

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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

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

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

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

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.com

Time Stamps:

00:00 - Introduction to Drew Sechrist

00:48 - Drew’s Early Career and Salesforce Journey

01:45 - The Power of a Well-Timed Cold Email

05:48 - Navigating Relationships and Networking at Salesforce

08:50 - Mentorship and Early Sales Lessons

16:14 - Building Community Across Geographies

18:55 - Learning from Mistakes and Iterating

20:18 - The Importance of Feedback in Networking

23:16 - Tools for Building and Maintaining Relationships

27:51 - Final Thoughts on Relationship Building

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.com

Time Stamps:

00:00 Introduction: Why Relationships Matter

02:04 Defining Fulfillment & Purpose at Work

04:54 From Chemical Engineering to Tech

07:58 Learning to Translate Tech for Business

08:33 How Relationships Actually Create Opportunity

10:00 The 14 Rejections That Changed Everything

14:14 Salesforce: From IC to President

16:01 Leaving, Returning, and Seeing Clearly

17:33 Servant Leadership & Helping Others Rise

19:08 Goal Setting That Works (V2ME Framework)

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.com

https://whogotmehere.substack.com

Time Stamps:

00:00 – Meet Whitnie Narcisse: From Teaching 8th Grade Science to Venture Capital

01:00 – Saying Yes Early: Teach for America, Nonlinear Careers, and Learning by Doing

02:45 – The Trivia Night That Quietly Changed Everything

07:00 – Breaking Into Venture Without a Straight Line (or a Perfect Plan)

09:00 – Networking with Agency: Confidence, Bold Outreach, and Assuming Positive Intent

14:00 – Modern Mentorship: Loom Videos, Async Advice, and Protecting Your Time

16:00 – Building Community at First Round: Why Relationships Compound Over Time

18:30 – What Makes a Great Event: Guest Lists, Small Groups, and Intentional Design

20:30 – Rethinking Networking: Game Nights, Poker, and Making Connection Fun

22:30 – The FACE Framework: How to Be Memorable, Human, and Credible

Perfection might get views—but it doesn’t build connection. In this clip, Michael talks about why showing imperfection, struggling in real time, and leaving things unpolished actually removes intimidation and creates trust. It’s the difference between swipeable content and deep connection. When people feel your authenticity, identify with your story, and are genuinely learning alongside you, that’s the real summit of the internet—not follower counts or flashy edits, but meaningful depth with real people.

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.

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