Owner Mode

Owner Mode

By Gravy WealthBusinessEntrepreneurship
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Owner Mode episodes

  • First Check: Why First-Timers Win | Charles Hudson

    Charles Hudson has spent nearly 30 years investing in the Bay Area and runs Precursor Ventures, a pre-seed firm with more than 450 investments and over 1,000 founders behind it. In this Owner Mode conversation, he makes a counterintuitive case: the traits that make someone successful inside a corporation are often exactly what gets in the way of building a company from scratch.

    He explains why the corporate high achiever, the master of managing up and working a bureaucracy, often freezes at the formation stage when there is no system to work. He breaks down the founder he calls a naive optimist, the person with no industry experience who builds what insiders said could not be done, and why half of his best companies came from that profile.

    Charles also talks about how he evaluates people over ideas, how AI tools are changing who can build, and why he believes everyone in this job market needs an independence plan: thinking about your skills and abilities as separate from the employer you currently rent them to.

    This is a clear, specific look at what early-stage investors actually look for, and a reframe of who gets to build, for any high earner weighing whether to start something of their own.

    Chapters:
    00:00 A whiteboard and no plan
    02:31 Brandon introduces Charles Hudson
    02:40 The corporate high achiever who freezes at formation
    02:41 The naive optimists: half of his best founders
    02:50 A hundred founder conversations a month
    02:51 The cofounder who left twenty minutes ago
    03:00 Pedigree does not transfer
    03:03 In whose hands do you place your fate?
    03:04 The independence plan

    Links:
    Explore the Launch pathway: gravywealth.com/launch
    Full transcript: gravywealth.com/podcast/charles-hudson-first-check/transcript
    Owner Mode Memo: gravywealth.com/memo
    DNA Assessment: go.gravywealth.com/DNA

    Disclaimer: This content is for educational and informational purposes only and reflects the personal experiences and opinions of the participants. Nothing here is investment, legal, tax, or financial advice, or a recommendation to buy or sell any security. Past results do not guarantee future outcomes. Do your own research and consult your own professional advisors before making any financial decision.

    35 min
  • Investing Beyond the Day Job | Andrew Lindsay (Microsoft)

    Andrew Lindsay is Corporate Vice President, Cloud and AI Platforms Business Development at Microsoft, where he leads partnerships with OpenAI, Anthropic, and xAI. He also sits on the board of Asana and has spent fifteen years building a private portfolio of real estate, fund investments, and direct angel checks, all while holding one of the most demanding corporate roles in the country.

    In this Owner Mode conversation, Andrew breaks down how he deploys personal capital when time is short. He explains the bright-line rule that keeps him from investing where his work intersects, even when founders ask him in directly, and why that constraint actually speeds up the rest of his decisions. When he decides where money goes, he does not lead with returns. He thinks about where he wants to put his time, and treats the two as the same kind of investment.

    He walks through the Bayview real estate story: how he found a Community Reinvestment Act program buried in a decade-old PDF and put 3.5% down in one of the most expensive housing markets in the country, then bought a three-unit building nearby with 5% down. He details the investor of first resort framework, the single question he asks before any private deal, and how he uses AI as a research partner rather than a search engine. He closes on the AI era itself, and his honest read from inside the room that nobody can predict where it goes next.

    This is a clear, specific look at how a senior executive builds private-market ownership without quitting, without conflicts, and without waiting for the perfect moment. If you have capital sitting idle because the next move feels too complex, this conversation is a practical starting point.

    Chapters:
    00:01 Introduction: a busy executive and family man building a private portfolio
    08:50 Capital goes where time goes: the investment philosophy
    10:01 The bright-line rule: no investing where your work intersects
    13:24 Portfolio construction: the public-to-private split
    15:59 Bayview: the 3.5% down program and the three-unit building
    25:57 AI as a research partner for financing
    29:44 How the portfolio pays for itself today
    38:23 "Investor of first resort": deal access and evaluation
    47:14 The tandem-jump analogy and the biggest mistake he made
    51:26 Inside the room: nobody knows where AI goes next

    Links:
    Foundation: gravywealth.com/foundation
    Full transcript: gravywealth.com/podcast/andrew-lindsay-investing-beyond-day-job/transcript
    Owner Mode Memo: gravywealth.com/memo
    Owner Mode podcast: gravywealth.com/podcast
    DNA Assessment: go.gravywealth.com/DNA

    Disclaimer: This content is for educational and informational purposes only and reflects the personal experiences and opinions of the participants. Nothing here is investment, legal, tax, or financial advice, or a solicitation to buy or sell any security. Investing in private securities involves significant risk, including possible loss of principal, and past performance does not guarantee future results. Do your own research and consult your own professional advisors before making any investment decision.

    57 min
  • Profit from the Podium: A Side Income on Stage | Lexi B.
    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.
    1 hr 4 min
  • The Other Side: 3 Deals. 3 CEOs. No Filter. | Mitch Harris, Mario Antwine, Rahman "Rock" Irvin
    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.
    1 hr 6 min
  • The Long Game: How Squire Hit $750M | Dave Salvant and Songe LaRon
    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.
    58 min
  • The Billion-Dollar Business Model | Samir Goel
    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.
    40 min
  • Turn What You Know Into What You Own | Arlan Hamilton
    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.
    49 min
  • From the Room to the Cap Table | Chris Lyons (a16z)
    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.
    47 min
  • Welcome to Owner Mode

    Two kinds of people on this planet: earners and owners.

    Owner Mode is the series for high-earning professionals who've built real careers and income, only to discover they may be climbing the wrong mountain.

    Host Brandon William Jones, founder and CEO of Gravy Wealth, convenes luminaries like Mellody Hobson, top VC partners like a16z's Chris Lyons, and people building ownership on the side or all in, for the conversations that usually happen behind closed doors.

    Follow now and don't miss an episode.

    3 min

About Owner Mode

From the publisher's feed

There are two kinds of people on this planet: earners and owners. And it all starts with an identity shift. That's where Owner Mode comes in.

Owner Mode is the series for high-earning…