Owner Mode

Gravy Wealth
  • 5.0 (1)
  • Entrepreneurship

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 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, sits down with luminaries like Mellody Hobson, top VC partners like a16z's Chris Lyons, founders who've built businesses from the ground up or through acquisition, and professionals who've built ownership on the side and made the calculated leap. These are the conversations that usually happen behind closed doors, diving into the real pathways and journeys that took them to the other side. If you're ready to shift into Owner Mode, you're in the right place.

  1. 4d ago

    The Fractional Path | Sherika Ekpo

    Sherika Ekpo climbed into the C-suite in human resources, and burnout came with it. Before she left, she started a consulting business on the side and grew it through referrals and conferences, so when a package came, she already had clients. Today she serves as fractional chief HR officer for about three companies at a time. In this Owner Mode conversation she explains how fractional work differs from consulting. A consultant hands over a framework and moves on; a fractional executive sits in the leadership meetings and is responsible for hiring, strategy and the outcome. She also makes the case that the skills matter more than the title for anyone considering this work. She gets specific about the mechanics: pricing from the 55-hour weeks she actually worked, why one client at 20 hours a month could not replace her salary, the anchor client that keeps the revenue steady, putting anything longer than 90 days on a retainer, and asking for board seats and equity when a smaller company cannot pay cash. Her close is about risk and the bridge into entrepreneurship: a household plan built around her husband's steady job, a franchise opened with a ten-year view, and an honest account of how different it felt once the 1099 was all she had. Chapters: 00:00 From the C-suite to burnout, and a business started on the side 03:36 Consultant or fractional executive, and whether you need the title 09:17 Private versus public fractional, and the reputation you lend 12:58 Scoping the work and landing clients through referrals 18:17 Retainers, board seats and asking for equity 20:31 Pricing from the hours you really worked 24:08 Three clients, one anchor, and the air traffic controller 28:23 Risk, a partner's paycheck, and the bridge to ownership Links: Book Sherika Ekpo 1-on-1: gravywealth.com/expert/sherikaekpo Full transcript: gravywealth.com/podcast/sherika-ekpo-fractional-path/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 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.

  2. Nov 2

    The Multiplier | Naithan Jones & Tony Brown

    Naithan Jones is a multi-time founder who spent time as an investor at Andreessen Horowitz and has advised high-growth startups for years. Tony Brown is the co-CEO and co-founder of Breakr, a fintech that has raised $9M, and Naithan has been his advisor since they met in 2015. In this Owner Mode panel they define what an advisor is actually worth. The advice itself, Naithan says, is maybe ten percent of the value. The rest is the questions, because an advisor can never know the business the way the founder does. He has never asked to be an advisor; he has always been asked, because he gave value first. They also get into how to structure advisory equity so it pays for results, the question founders should ask anyone who wants advisory shares, and why a reputation for creating value opens more doors than capital, for advisors and angel investors alike. Tony brings the founder's side: leaving a corporate finance career, the help that changed his trajectory, and the 1,500 committed days that changed his life whether or not the company worked. This is a candid, two-sided look at one of the most misunderstood relationships in building a company. Chapters: 00:00 Meet the investor and the founder he advises 02:45 Leaving Goldman and JPMorgan, and finding a multiplier 06:44 What an advisor delivers: the questions, not the answers 12:22 Structuring advisory equity, and thinking like an angel 19:31 Why access comes down to place, and the nerve to stand out 26:03 Tony's first $250K, and the bet on distribution 34:25 Backing the one thing someone does world class 45:40 Don't advise your friends first, and parting advice Links: Book Naithan Jones 1-on-1: gravywealth.com/expert/naithanjones Full transcript: gravywealth.com/podcast/nait-tony-panel-multiplier/transcript Owner Mode Memo: gravywealth.com/memo Owner Mode podcast: gravywealth.com/podcast DNA Assessment: go.gravywealth.com/DNA 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.

  3. Oct 26

    The Franchise Player | Chequan Lewis

    Chequan Lewis is the CEO of Crunch Fitness. He came to franchising from the law, taking a job as a franchise lawyer with almost no knowledge of franchising, and went on to serve as COO of Pizza Hut and its first Chief Equity Officer. In this Owner Mode conversation, he explains how a high earner should actually pick a franchise. He starts with who franchising suits and who it does not, then the three kinds of risk to weigh: capital, interpersonal and emotional. He covers why you should ask any franchise broker how they get paid, why existing franchisees are the best source of truth on a brand, and the three checks he would run before buying: unit-level economics against the peer group, the brand's growth discipline, and its support for operators. His sharpest warning is that it is very easy to buy yourself a job and not realize it. On a thin-margin unit, paying a manager can leave too little to replace a salary, so he asks whether the franchise needs to be your job before anything else. He closes on the three C's franchisors screen for, capability, capital and commitment, and on why the hands-off franchise is mostly a myth. Chapters: 00:00 One thin-margin unit can buy you a job 00:30 From litigator to franchise lawyer to a P&L at 35 07:34 Chief equity officer, COO, then Crunch Fitness 14:45 Who franchising is for, and the risk underneath it 23:11 Picking a category and sizing your capital 35:26 Brokers, franchisee calls, and three checks to run 44:45 Unit math, hands off, and buying yourself a job 53:07 The three C's and the future of franchising Links: Explore the Acquire pathway: gravywealth.com/acquire Full transcript: gravywealth.com/podcast/chequan-lewis-franchise-player/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 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.

  4. Oct 20

    From Houses to Hotels | Evens Charles

    For years Evens Charles thought the person running a big deal had to fund all of it. He started with a $32,000 row home in West Philadelphia and $1,000 of his own money while earning about $21,000 a year. Today he is the founder of a $350M hotel portfolio of Hilton- and Marriott-branded hotels across 7 states, with a $1.1B development pipeline, run by a team of fewer than ten people. In this Owner Mode conversation he lays out the path from houses to hotels: living on the same budget and putting every sales bonus into real estate, the conference where he met the team for his first hotel, and the SBA loan that financed 80% of that $3 million, 70-room property. He also explains how bigger deals are funded, including the 90/10 structure in which a limited partner provides most of the equity and the sponsor provides a small share and runs the deal, and why a strong brand, through its reservation system, can supply 35 to 40 percent of a hotel's business. He is honest about the risks. Hotels run 24 hours a day, lenders want real net worth and liquidity from a sponsor, and COVID hit hotels harder than any other kind of real estate. This is a grounded look at how a self-funded start became a branded hotel portfolio. Chapters: 00:00 Why hotels are a franchise game most people never see 02:33 A $1,000 row home, a $21K job, and every bonus into real estate 09:02 The book, the conference, and the first hotel deal 18:06 Why hotels run differently, and the guests a brand sends you 24:46 How the deals get funded, from SBA to the 90/10 split 37:15 How to get in now: partners, passive stakes and conferences 42:15 His thesis: premium brands, select service and up-branding 47:09 COVID, leverage and the case for diversifying Links: Full transcript: gravywealth.com/podcast/evens-charles-houses-to-hotels/transcript Owner Mode Memo: gravywealth.com/memo Owner Mode podcast: gravywealth.com/podcast DNA Assessment: go.gravywealth.com/DNA 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.

  5. Oct 19

    From Houses to Hotels | Evens Charles

    Evens Charles started with a $32,000 row home in West Philadelphia and $1,000 of his own money while earning about $21,000 a year. Today he is the founder of a $350M hotel portfolio of Hilton- and Marriott-branded hotels across 7 states, with a $1.1B development pipeline, run by a team of fewer than ten people. In this Owner Mode conversation he lays out the path from houses to hotels: living on the same budget and putting every sales bonus into real estate, the conference where he met the team for his first hotel, and the SBA loan that financed 80% of that $3 million, 70-room property. He also explains how bigger hotel deals are funded, including the 90/10 structure in which a limited partner provides most of the equity and the sponsor provides a small share and runs the deal, and why a major brand's reservation system can supply 35 to 40 percent of a hotel's business. He is honest about the risks. Hotels run 24 hours a day, lenders want real net worth and liquidity from a sponsor, and COVID hit hotels harder than any other kind of real estate. This is a grounded look at how a self-funded start became a branded hotel portfolio. Chapters: 00:00 Why hotels are a franchise game most people never see 02:33 A $1,000 row home, a $21K job, and every bonus into real estate 09:02 The book, the conference, and the first hotel deal 18:06 Why hotels run differently, and the guests a brand sends you 24:46 How the deals get funded, from SBA to the 90/10 split 37:15 How to get in now: partners, passive stakes and conferences 42:15 His thesis: premium brands, select service and up-branding 47:09 COVID, leverage and the case for diversifying Links: Explore the Build pathway: gravywealth.com/build Full transcript: gravywealth.com/podcast/evens-charles-houses-to-hotels/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 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.

  6. Oct 12

    The Hidden Playbook | Will Drewery

    Will Drewery managed about $3.5 billion in equipment spend at Tesla before he left to build his own company. When he founded Diagon, he launched it on a playbook most founders never get told: do not pay full price for anything in year one. In this Owner Mode conversation, Will breaks down the mechanics nobody advertises. Law firms that believe you are headed for venture funding will defer their fees until you raise. VC firms will pay you a contractor wage to incubate an idea through an entrepreneur-in-residence program. Your own bootstrap cash can go in as a promissory note you can recover later instead of money you simply spend. He also walks through how a venture call is actually structured, why he weights a founder's network far above the idea itself, and the tax moves that decide how much of the upside you keep, including the 83(b) election he filed on four million shares for $40 and the QSBS exclusion that can make up to $10 million of gain tax-free. He is clear-eyed about the limits, too. None of the deferrals are free money, and the programs depend on a firm believing you are genuinely venture-track. This is a straight look at how a senior operator launches without burning his savings, and why he thinks the cost of building has never been lower. Chapters: 00:00 A playbook nobody advertises 00:54 Brandon introduces Will Drewery 00:56 From Baghdad to an early seat at Tesla 00:58 Managing $3.5B in spend, and the bonus that woke him up 01:01 The belief: founders should not pay full price in year one 01:03 Getting paid to build: the entrepreneur-in-residence path 01:08 Deferred billing: how firms carry a pre-funded founder 01:10 The promissory note: bootstrap cash you can get back 01:14 How a venture call is actually structured 01:24 83(b) and QSBS: keeping the value you create 01:31 A working MVP in 45 minutes 01:35 The game is rigged, and why now is the moment Links: Book Will Drewery 1-on-1: gravywealth.com/expert/willdrewery Explore the Launch pathway: gravywealth.com/launch Full transcript: gravywealth.com/podcast/will-drewery-hidden-playbook/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 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.

  7. Oct 5

    What Makes Operators Board-Ready | Robin Washington

    Robin Washington sits on the boards of Alphabet and Honeywell and serves as President, COO, and CFO of Salesforce. Her first board seat came before she was even a CFO. In this Owner Mode conversation, she explains the one thing she says makes anyone board ready: being genuinely exceptional at your day job, because the board members and leadership team around you are the ones who notice. She describes writing "join a Fortune 500 public board" into her performance appraisal as a sitting CFO, telling the board members she knew, and how her seats followed, one through a recruiting firm and one from Mark Benioff after years of knowing each other. She also covers what a board member actually does and why great operators can struggle with it, what her first boardroom was like as the only woman in the room, the reputation risk that comes with every seat, and the question she asked Sundar Pichai before joining Alphabet: why do you want me on this board? Chapters: 00:00 The one thing that makes you board ready 00:30 Why a board director stepped in to run the company 07:13 From finance to a first board seat before CFO 14:20 You are not an operator as a board member 16:56 The only woman in her first boardroom 21:00 Getting noticed and putting the goal in writing 29:44 The reputation risk that comes with every seat 33:46 Why do you want me on this board? Links: Explore the Advise pathway: gravywealth.com/advise Full transcript: gravywealth.com/podcast/robin-washington-what-makes-operators-board-ready/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 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.

  8. Sep 28

    The Patient Owner | Mellody Hobson (Ariel Investments)

    Mellody Hobson has been investing for 35 years. She is Co-CEO of Ariel Investments, one of the most respected active-management firms in America, a Board Director at JPMorgan Chase, and former Chair of both Starbucks Corporation and DreamWorks Animation. In this Owner Mode conversation, she makes the case for patience as the real edge in private markets. Asked what high earners get wrong, she leads with the trade-off rather than the upside: private markets cost you liquidity, and you cannot simply change your mind and sell. From there she lays out a clear sequence. Build a diversified public portfolio first. Treat private markets as the add-on, not the anchor. Find a financial adviser who syndicates access. Then accept the illiquidity and hold. She also walks through the Ariel thesis of investing in what is misunderstood, ignored, and under-followed, and applies it to women's sports, which she calls the small caps of sports. She names the access reality without hedging, including her own fund's $5 million minimum. The throughline is the line she keeps returning to: it's the time in the market, not timing the market that leads to long term success. Her closing instruction is the one to keep: if you are going to be an owner, be a patient owner. This is a clear, experienced look at how to enter private markets the right way, from someone who has spent three and a half decades inside the room. Chapters: 00:09:24 Introduction: Mellody Hobson and the Ariel approach 00:13:18 Investing in the misunderstood, ignored, and under-followed 00:13:22 Women's sports as the small caps of sports 00:14:45 The honest access conversation: the $5 million minimum 00:17:54 Democratizing access to long-term wealth 00:22:02 Time in the market, not timing the market 00:23:13 How to enter private markets: an add-on, not an anchor 00:26:15 AI and what stays valuable for knowledge workers 00:29:05 The information diet: four papers and "buy reading glasses" 00:34:35 If you're gonna be an owner, be a patient owner Links: Foundation: gravywealth.com/foundation Full transcript: gravywealth.com/podcast/mellody-hobson-patient-owner/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.

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About

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 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, sits down with luminaries like Mellody Hobson, top VC partners like a16z's Chris Lyons, founders who've built businesses from the ground up or through acquisition, and professionals who've built ownership on the side and made the calculated leap. These are the conversations that usually happen behind closed doors, diving into the real pathways and journeys that took them to the other side. If you're ready to shift into Owner Mode, you're in the right place.

Information

  • Creator
    Gravy Wealth
  • Years Active
    2026
  • Episodes
    25
  • Rating
    Explicit
  • Copyright
    © 2026 Gravy Wealth
  • Show Website
    Owner Mode