The Podcast

Lexi B. is a big tech executive who built a public speaking business that brings in up to 70% of her corporate salary, without ever leaving the job. In this Owner Mode conversation, she breaks down exactly how she did it, and why the outside brand made her stronger inside the company rather than a flight risk. She traces the business back to a single $600 check for speaking to a group of HBCU students visiting Silicon Valley, and her reaction of "for what?" From there she explains how she reinvested every early dollar into the infrastructure of a real business: a lawyer, a contract, a website, headshots, a speaker kit. She goes deep on the pricing model that changed how she valued her time, after a mentor taught her to charge for the full body of work behind a keynote rather than the ninety minutes on stage. The Warsaw story is the proof. A $300 out-of-pocket trip to a conference that could not cover her fee came back at roughly fifteen times her rate and produced ten booked international engagements by January 2020. Two months later live events collapsed, and because her contracts carried real cancellation terms, 2020 became her biggest financial year as a speaker. She also explains the discipline that kept it from being a hobby, never speaking until her fee has cleared, why she keeps her speaking work and her day job deliberately separate, and why she says the most powerful place to be at any conference is backstage, with the people who book the speakers. If you have a skill inside your job that someone outside your company would pay to hear you explain, this conversation is a concrete map for building it into a second income while keeping the first. Chapters: 00:00 Cold open: a unique story versus a Disney story 02:50 Origin: from St. Louis to the Bay, and an accidental tech career 08:20 The first $600 check: "for what?" 16:00 Going pro: lawyer, contract, website, headshots, speaker kit 26:00 Pricing your worth: "the bag's just always expensive" 34:00 The Warsaw play: $300 in, speaker fee times 15 out 43:00 Job security as a byproduct: inbound offers and the manager jokes 50:00 LinkedIn as billboard marketing between engagements Links: Book Lexi B. 1-on-1: gravywealth.com/expert/lexibutler Explore the Create pathway: gravywealth.com/create Full transcript: gravywealth.com/podcast/lexi-b-profit-from-podium/transcript Owner Mode Memo: gravywealth.com/memo Owner Mode podcast: gravywealth.com/podcast DNA Assessment: go.gravywealth.com/DNA The Owner Mode podcast is for educational purposes only and is not investment advice. References to specific investments are illustrative and not recommendations. Investment opportunities through Gravy Capital are offered only to accredited investors. See full disclosures in the description.

Three corporate executives left high-paying careers, ran multi-year acquisition searches, and now run the companies they bought. Mitch Harris, Mario Antwine, and Rock Irvin sit down for an unfiltered account of what the acquisition path actually looks like. The trigger for Mario was a Fortune 500 CFO telling him his exact career track to his face. He went on to self-fund a contact center business with a top line north of $50 million, and ran year one through roughly a thousand employees and no days off, with the mental load — not the hours — as the hardest part. Mitch came out of Meta, searched 20 months, and describes his first months as CEO as grimy, with about seventy-five percent of his time going to administrative work. Rock got roughly seven thousand no's during his solo search and built a system to batch the rejection to a single day. All three agreed on the core lesson: the financing solves once you find the deal, and finding the deal is the hard part. They also agreed that staying put stopped feeling like the safe option. Rock put the ceiling plainly — keep doing what you are doing and you will never be paid in line with the value you generate — and framed it as a structure, not a personal failing. This conversation covers deal size and the danger of buying a job, spouse and partner alignment, search discipline, financing a larger deal, the unglamorous first hundred days, and the resilience the path requires. If you have wondered what the other side of an acquisition actually feels like, this is the honest version. Chapters: 00:00 Cold open: a Fortune 500 CFO names the ceiling 00:15 Brandon introduces the panel and why it exists 02:30 Mario's background and why he chose acquisition 05:00 Rock's background and how the risk math changed 08:00 Mitch's background: the compensation ceiling and the why 11:30 Why acquisition: control, ceiling, legacy 15:30 Deal size, financing, and not buying a job 20:00 Partner alignment before the search starts 24:00 Search discipline: Rock's Monday pain system 30:00 Mitch's buy box and the shift to mitigation thinking 34:00 Mario on financing a $50M+ deal 38:00 Diligence: the sim is lipstick on a pig 44:00 The first hundred days: Mitch's unglamorous CEO reality 50:00 Year one with 1,000 employees: Mario's mental load 54:00 Resilience, almost quitting, and what day one felt like Links: Book Mitch Harris 1-on-1: gravywealth.com/expert/mitchharris Book Mario Antwine 1-on-1: gravywealth.com/expert/marioantwine Explore the Acquire pathway: gravywealth.com/acquire Full transcript: gravywealth.com/podcast/mitch-mario-rock-panel-other-side/transcript Owner Mode Memo: gravywealth.com/memo Owner Mode Podcast: gravywealth.com/podcast DNA Assessment: go.gravywealth.com/DNA The Owner Mode podcast is for educational purposes only and is not investment advice. References to specific investments are illustrative and not recommendations. Investment opportunities through Gravy Capital are offered only to accredited investors. See full disclosures in the description.

Dave Salvant left JPMorgan. Songe LaRon left a Yale Law partner track at Skadden Arps. Neither could code. Together they built Squire, the barbershop technology platform, to a $750 million valuation. In this Owner Mode conversation, the two co-founders walk through the long game. They explain the two different frameworks that got them to leave stable, high-status careers: Songe's asymmetry of risk reward, where the downside was survivable and the upside limitless, and Dave's golden handcuffs argument, where the cost of staying compounds until leaving becomes impossible. They describe finding the idea by sneaking into empty Columbia classrooms on weekends, how two non-technical founders recruited a technical team, and the brutal fundraising stretch where three Y Combinator applications and sixty Series A meetings produced a single term sheet while the company nearly ran out of money. They also share the filter that kept Squire alive through more than a decade of building: putting the customer first. By the end of 2019, three and a half years after launch, a Series B with a secondary made both founders liquid millionaires. If you have framed staying put as the safe choice, this conversation is a clear case for running the actual math on the downside first. Chapters: 00:00 Cold open: the biggest risk is not taking the risk 00:03 Songe: Yale Law, Skadden Arps, and the unfulfillment 00:07 Dave: JPMorgan, Harlem ventures, and the generational-wealth filter 00:12 Golden handcuffs and going all in 00:17 Asymmetry of risk reward: the lawyer's calculation 00:20 Sneaking into Columbia: whiteboarding on weekends 00:34 Non-technical founders and selling the CTO first 00:38 Investors who Googled the market 00:52 Three and a half years to liquid millionaires 00:59 Untethering time from money Links: Explore the Launch pathway: gravywealth.com/launch Full transcript: gravywealth.com/podcast/squire-panel-long-game/transcript Owner Mode Memo: gravywealth.com/memo Owner Mode podcast: gravywealth.com/podcast DNA Assessment: go.gravywealth.com/DNA The Owner Mode podcast is for educational purposes only and is not investment advice. References to specific investments are illustrative and not recommendations. Investment opportunities through Gravy Capital are offered only to accredited investors. See full disclosures in the description.

Samir Goel ran a $500M business unit at LinkedIn while building Esusu on nights and weekends. Esusu is now a $1.2 billion fintech that turns rent payments into credit for 12 million renters across all 50 states. In this Owner Mode conversation, Samir breaks down the full arc. He explains the insight at the core of the company, that rent is the most consistent monthly payment in tens of millions of households and had never been used to build credit, and how Esusu routes that data to the three major credit bureaus for 45 million credit-invisible Americans. He walks through the three pivots it took to find the business model, and the unlock of selling to landlords instead of renters so revenue comes from the party with the budget. He describes the two and a half years building the company while at LinkedIn and the 18-month bootstrap that followed, with $100K in credit card debt and a closet in Harlem. He also shares the framing that kept the company disciplined: venture capital is a mortgage, an obligation to pay back, not a reward. Esusu now counts Blackstone, Fannie Mae, and Freddie Mac as clients and has helped unlock $30 billion in mortgages. If you have a company idea and a job you are not ready to leave, this is a clear map for building without a safety net. Chapters: 00:00 Cold open: I don't know you like that 01:00 Brandon introduces Samir Goel 03:00 Two immigrant families and the mission behind Esusu 11:00 Piggyback on existing trust: the B2B2C model 13:00 Rent, the most underwritable data point we never used 15:00 The 18-month bootstrap: $100K debt and the Harry Potter closet 22:00 Enterprise sales the hard way: Related Companies and Blackstone 27:00 Get your major right: the LinkedIn side hustle protocol 33:00 The co-CEO model and disagree and commit Links: Explore the Launch pathway: gravywealth.com/launch Full transcript: gravywealth.com/podcast/samir-goel-billion-dollar-business-model/transcript Owner Mode Memo: gravywealth.com/memo Owner Mode podcast: gravywealth.com/podcast DNA Assessment: go.gravywealth.com/DNA The Owner Mode podcast is for educational purposes only and is not investment advice. References to specific investments are illustrative and not recommendations. Investment opportunities through Gravy Capital are offered only to accredited investors. See full disclosures in the description.

Arlan Hamilton was homeless until September 2015, the year she started building Backstage Capital. She had no money and no connections, just a Twitter account and a plan to become the first call any underestimated founder made when they started a company. In this Owner Mode conversation, she traces how she turned a point of view into real leverage. She built the fund in public, tweeting the journey of raising it before she had raised a dollar, at a time when people who cared about her warned that a venture capitalist could not be that loud. She kept going, and the largest funds in the world now run that same build-in-public play as their model. That visibility is what brought the proof points within reach. Mark Cuban invested $6 million because, in his words, she was in rooms he would never be in. A relationship with Sam Altman that began in 2014, while she was still homeless, became a direct Backstage investment in OpenAI made within weeks of her asking. At 45 she stepped back from running the fund and stayed its largest stakeholder. The second act is where the brand becomes the product. She walks through the AI tool stack behind a single sales page that has earned more than $100,000 since October, the free challenge with ten thousand people inside it, and the dashboards she built herself. Her argument is that this AI moment is the meritocracy the tech industry has promised for decades, and that the advantage belongs to whoever starts learning the tools first. This is a clear look at how a personal brand becomes the asset that access, deals, and income all run on, built by someone who started with none of the usual advantages. If you have been waiting for permission to build your platform, Arlan's answer is to start now, in public, before you feel ready. Chapters: 00:00 Cold open: one day, everybody will know my name 00:05 Brandon introduces Arlan Hamilton 00:09 Origin: the daycare shuttle and the line she could not explain 00:13 Homeless until 2015, and tweeting the journey of raising a fund 00:16 "I'm not famous, but I can make myself known" 00:21 Mark Cuban's $6M and "you're in rooms I'll never be in" 00:25 Sam Altman, and how Backstage got onto OpenAI's cap table 00:29 Willingness to fail in public 00:32 A decade on one brand, then stepping back as largest stakeholder 00:46 YouTube: 150K subscribers from a laptop Links: Explore the Create pathway: gravywealth.com/create Full transcript: gravywealth.com/podcast/arlan-hamilton-turn-what-you-know-into-what-you-own/transcript Owner Mode Memo: gravywealth.com/memo Owner Mode podcast: gravywealth.com/podcast DNA Assessment: go.gravywealth.com/DNA The Owner Mode podcast is for educational purposes only and is not investment advice. References to specific investments are illustrative and not recommendations. Investment opportunities through Gravy Capital are offered only to accredited investors. See full disclosures in the description.

Chris Lyons has spent over fifteen years inside Andreessen Horowitz watching who actually gets access to private markets, and his answer is not the one most people expect. He founded a16z's Cultural Leadership Fund, the vehicle that brought cultural leaders like Nas, Kevin Durant, and Jada Pinkett Smith into early equity in companies like Coinbase, Airbnb, and Instagram before they went public, and he later launched the firm's first $400M Seed Fund. In this Owner Mode conversation, Chris opens with a blunt premise: private markets are private for a reason, and pretending otherwise helps no one. He is honest about the gate. The Cultural Leadership Fund sits at the $5M+ investment tier, and the structures around the big funds exist to keep smaller checks out. From there he reframes the real barrier to the next wave as information rather than net worth. The turning point is the endorsement-to-equity gap. He uses DJ Khaled going viral on Snapchat and helping build a multibillion-dollar business while sitting nowhere on the cap table, the exact gap the Cultural Leadership Fund was built to close. He then reads what comes next: AI removing the technical co-founder wall, and crypto rebuilding the rails of ownership underneath the consumer layer. The throughline is that ownership starts before the investment. Own your taste, your network, your point of view, and your time, and the cap table follows your conviction. For anyone who has spent years consuming the companies that made other people wealthy, this is a clear map of how the access question is changing. Chapters: 00:07:39 Introduction: Chris Lyons and his path from Atlanta music to a16z 00:13:00 The network philosophy: pick-up-the-phone relationships 00:20:05 Private markets 101: why they're private and what it means 00:23:56 The Cultural Leadership Fund: shared genius 00:31:07 Endorsement vs. equity: why consumers were left off the cap table 00:42:48 Crypto as ownership layer: Web1 read, Web2 write, Web3 own 00:47:14 AI removes the technical barrier 00:53:29 Ownership as identity: taste, network, point of view, time Links: gravywealth.com/foundation gravywealth.com/memo gravywealth.com/podcast go.gravywealth.com/DNA The Owner Mode podcast is for educational purposes only and is not investment advice. References to specific investments are illustrative and not recommendations. Investment opportunities through Gravy Capital are offered only to accredited investors.