Owner Mode

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 see02:33 A $1,000 row home, a $21K job, and every bonus into real estate09:02 The book, the conference, and the first hotel deal18:06 Why hotels run differently, and the guests a brand sends you24:46 How the deals get funded, from SBA to the 90/10 split37:15 How to get in now: partners, passive stakes and conferences42:15 His thesis: premium brands, select service and up-branding47:09 COVID, leverage and the case for diversifyingLinks:Full transcript: gravywealth.com/podcast/evens-charles-houses-to-hotels/transcriptOwner Mode Memo: gravywealth.com/memoOwner Mode podcast: gravywealth.com/podcastDNA Assessment: go.gravywealth.com/DNAThis 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.

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 see02:33 A $1,000 row home, a $21K job, and every bonus into real estate09:02 The book, the conference, and the first hotel deal18:06 Why hotels run differently, and the guests a brand sends you24:46 How the deals get funded, from SBA to the 90/10 split37:15 How to get in now: partners, passive stakes and conferences42:15 His thesis: premium brands, select service and up-branding47:09 COVID, leverage and the case for diversifyingLinks:Explore the Build pathway: gravywealth.com/buildFull transcript: gravywealth.com/podcast/evens-charles-houses-to-hotels/transcriptOwner Mode Memo: gravywealth.com/memoOwner Mode podcast: gravywealth.com/podcastDNA Assessment: go.gravywealth.com/DNADisclaimer: 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.

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 advertises00:54 Brandon introduces Will Drewery00:56 From Baghdad to an early seat at Tesla00:58 Managing $3.5B in spend, and the bonus that woke him up01:01 The belief: founders should not pay full price in year one01:03 Getting paid to build: the entrepreneur-in-residence path01:08 Deferred billing: how firms carry a pre-funded founder01:10 The promissory note: bootstrap cash you can get back01:14 How a venture call is actually structured01:24 83(b) and QSBS: keeping the value you create01:31 A working MVP in 45 minutes01:35 The game is rigged, and why now is the momentLinks:Book Will Drewery 1-on-1: gravywealth.com/expert/willdreweryExplore the Launch pathway: gravywealth.com/launchFull transcript: gravywealth.com/podcast/will-drewery-hidden-playbook/transcriptOwner Mode Memo: gravywealth.com/memoOwner Mode podcast: gravywealth.com/podcastDNA Assessment: go.gravywealth.com/DNADisclaimer: 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.

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 ready00:30 Why a board director stepped in to run the company07:13 From finance to a first board seat before CFO14:20 You are not an operator as a board member16:56 The only woman in her first boardroom21:00 Getting noticed and putting the goal in writing29:44 The reputation risk that comes with every seat33:46 Why do you want me on this board?Links:Explore the Advise pathway: gravywealth.com/adviseFull transcript: gravywealth.com/podcast/robin-washington-what-makes-operators-board-ready/transcriptOwner Mode Memo: gravywealth.com/memoOwner Mode podcast: gravywealth.com/podcastDNA Assessment: go.gravywealth.com/DNADisclaimer: 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.

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 approach00:13:18 Investing in the misunderstood, ignored, and under-followed00:13:22 Women's sports as the small caps of sports00:14:45 The honest access conversation: the $5 million minimum00:17:54 Democratizing access to long-term wealth00:22:02 Time in the market, not timing the market00:23:13 How to enter private markets: an add-on, not an anchor00:26:15 AI and what stays valuable for knowledge workers00:29:05 The information diet: four papers and "buy reading glasses"00:34:35 If you're gonna be an owner, be a patient ownerLinks:Foundation: gravywealth.com/foundationFull transcript: gravywealth.com/podcast/mellody-hobson-patient-owner/transcriptOwner Mode Memo: gravywealth.com/memoOwner Mode podcast: gravywealth.com/podcastDNA Assessment: go.gravywealth.com/DNADisclaimer: 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.