Owner Mode

About Owner Mode

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.

Publisher

Gravy Wealth

Category

business

Language

en

Explicit

Yes

First episode

7 Jun 2026

Latest episode

26 Oct 2026

Latest episodes

22 episodes in the feed.

1. 

   26 Oct 2026

   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.

2. 

   19 Oct 2026

   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.

3. 

   12 Oct 2026

   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.

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