Owner Mode

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.

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.

Ashley Flucas is COO of Summit Ventures and founder of Flucas Ventures, one of the most active venture capital syndicates in the world, with 250+ investments including Databricks, Brex, and Mercury. She is a former capital markets attorney who left law to build all of it.

In this Owner Mode conversation, Ashley traces how she went from Harvard Law and capital markets law to one of the most active syndicates in the country. She came back to Florida in 2018 with no tech network, taught herself by writing small checks into deals she could afford to be wrong about, and treated the reps as the education. Her warning: if you just keep studying, you will get analysis paralysis. Within two years she launched her own first SPV, Andreessen Horowitz invested alongside her, and the New York Times profiled her.

She also breaks down the structure underneath the returns. She runs a barbell, venture for upside on one side, income and real estate for stability and tax treatment on the other. She explains how QSBS works on the venture side, how she chose an operating role that unlocked real estate depreciation, and why she moved her domicile to Florida. Her effective rate now runs in the mid-teens, the result of career design rather than a loophole.

She closes on risk, and her framing is the one to sit with. The bigger regret, in her view, is never taking the swing, as long as you have built the structure to survive the worst case first. This is a specific, candid look at how a high earner builds private-market ownership through action and structure rather than analysis, and why what you keep matters as much as what you make.

Chapters:
00:00 Own assets or get left behind
00:30 Brandon introduces Ashley Flucas
02:00 Duke, Harvard Law, and the box of career paths she thought existed
06:00 The book that reframed everything: The Monk and the Riddle
10:00 Florida, no tech network, and learning by doing
14:00 AngelList and the entry ladder into syndication
18:00 The barbell: venture on one side, real estate and income on the other
24:00 Golden handcuffs, autonomy, and the number that keeps moving
27:00 Tax structure: QSBS, depreciation, and Florida domicile
33:00 How to evaluate a syndicate and pick your first deals
40:00 What she is investing in now: AI infrastructure, aerospace and defense
44:00 The family office north star and the risk math
46:00 Closing: own assets or be left behind

Links:
Foundation: gravywealth.com/foundation
Full transcript: gravywealth.com/podcast/ashley-flucas-playing-chess/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.

Ryan Williams founded Cadre, a $5B+ real estate investment platform, at twenty-five, after stints at Goldman Sachs and Blackstone. He built it to do something those firms never did: put Harvard's endowment, BlackRock, and the Ford Foundation into the same institutional-quality deals as individual investors.

In this Owner Mode conversation, Ryan traces the whole arc. As a Harvard sophomore during the 2008 crisis, he saw a pricing dislocation in Atlanta, pooled money from classmates, and bought a house on New Hope Road for $63,000, making 3x unlevered before he graduated. By his first year at Goldman he owned nearly 1,000 residential units, run on nights and weekends.

What he could not unsee at the institutional shops was that the best private real estate deals reached only a tiny group of investors when the economics could have supported individuals. The gatekeeping was structural, not mathematical. So he built the door.

The principle underneath it all is trust. "Nothing compounds faster than trust. Not capital. Not talent. Not credentials." The first dollars in are trust dollars, and the way to compress that curve is to be the institutional version of yourself before you have institutional reasons to be. Ryan closes with why private markets are structurally less efficient and therefore richer in opportunity, and a three-question framework for allocating to illiquid assets.

Chapters:
02:36:49 Introduction: Goldman TMT, Blackstone real estate PE, founding Cadre at 25
02:41:39 The dorm-room thesis: what would have to be true for this not to work
02:43:55 First deal on New Hope Road: $63K in, 3x unlevered, junior year
02:46:42 Goldman by day, Atlanta real estate by night: nearly 1,000 units
02:59:51 The thing he could not unsee: the best deals reaching a tiny group
03:02:35 Nothing compounds faster than trust: the trust dollars framework
03:13:30 The case for private markets: structurally less efficient, more alpha
03:32:52 How to start: don't start with a deal, start with a thesis

Links:
Foundation: gravywealth.com/foundation
Full transcript: gravywealth.com/podcast/ryan-williams-private-markets-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 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.

Marlon Nichols and Bonita Stewart join the Owner Mode Summit to compare how a VC and an operator evaluate the same early-stage company. Marlon is Managing General Partner at MaC Venture Capital, with over $600M in AUM, 238 portfolio companies, and five IPOs. Bonita is Co-founder and Managing Partner of BAG Ventures and a co-lead of the BAG Collective, a 400+ angel investor community, and was the first Black woman VP at Google.

Marlon explains his second-order effects thesis: rather than investing in AI itself, he invests in what AI breaks and rebuilds downstream, across energy, the physical world, and specific industries. He lays out his four nonnegotiables for any team he backs: someone who understands the technology, a founder who pulls talent, a product person who can ship, and the ability to sell. He has tried to proceed with three of the four, and it never works.

Bonita brings the operator's lens to investing. She sends venture partners to look at a startup's code before BAG writes a check, screening for a real technology moat, and adds strategic resilience as a filter for founders who can absorb a setback and pivot at the right moment.

For high earners entering private markets, both deliver the same message: have a thesis before you write a check, invest in what you understand, and stay away from hype cycles. This is a practical look at how professional investors actually evaluate early-stage companies before any money moves, recorded as the fireside that opened the Summit's $100K pitch competition.

Chapters:
01:01:54 Introductions: Bonita Stewart and Marlon Nichols
01:05:40 Marlon's thesis: from cultural investing to second-order effects
01:11:46 Everything starts with team: Marlon's four nonnegotiables
01:19:14 Table stakes before the conversation: market, competition, unfair advantage
01:23:07 Bonita's AI filter: go under the hood and vet the tech
01:24:01 Strategic resilience: can the founder pivot at the right moment
01:32:24 Advice for high earners deploying their first six figures
01:34:31 Have a thesis before you write a check

Links:
Foundation: gravywealth.com/foundation
Full transcript: gravywealth.com/podcast/marlon-bonita-panel-framework-to-funding/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.

Stacy Brown-Philpot joined Google when it had roughly a thousand employees and was there as it grew to fifty thousand. She went on to run TaskRabbit as COO and then CEO, leading the company through its acquisition by IKEA. And while she was operating, she built a public-company board portfolio that included HP, Nordstrom, StockX, and Noom.

In this Owner Mode conversation, Stacy lays out the exact playbook she ran before any board opportunity existed. She explains the difference between a resume and a board bio, why she seeded her name proactively with directors and recruiters, and why a mentor told her to aim for the biggest public company first. She breaks down how she used HP's published skills matrix to know precisely which gap she could fill, and the advice that shaped her interview: stay in your lane.

She is direct about the cost and the payoff, including the phone interview she stopped when her youngest was crying, certain she had lost the seat, and what the board member told her instead. She also covers portfolio construction, the ten-year commitment reality, and the financial mechanics of public versus private boards.

Stacy is now Founder and Managing Partner of Cherryrock Capital, the first Black woman-founded, multi-hundred-million-dollar venture firm focused on Black and Latine founders. This is a tactical, honest guide to board service as an ownership pathway.

Chapters:
00:00 My baby's crying, I can't finish this interview
00:02 Brandon introduces Stacy and the phase-four bet
00:08 Detroit, Wharton, Goldman, and the road to Google
00:11 "I got lonely": founding the Black Googler Network
00:24 How global operating built her board-candidate profile
00:29 Discovering boards as the level above the C-suite
00:31 The board-entry playbook: bio, seeding the message, the skills matrix
00:40 Aim for a big public company first: the HP opening
00:45 "Stay in your lane": the interview advice from Ken Coleman
00:48 The Zuri call, and what the board member actually said
01:01 Two public boards plus CEO plus two kids: the honest cost
01:21 Phase four: Cherryrock Capital and completing the VC chapter

Links:
Explore the Advise pathway: gravywealth.com/advise
Full transcript: gravywealth.com/podcast/stacy-brown-philpot-building-your-board-portfolio/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.

Arthur Johnson spent his career in senior strategy roles at Goldman Sachs, Cisco, Twilio, and Pure Storage. He also quietly built a 50+ unit rental portfolio across Texas, Indiana, and Wisconsin, and used it to leave corporate at 52. In this Owner Mode conversation, he traces how a tech executive bought his way out one property at a time, without ever quitting his job.

The turning point was a desk at HP at nine at night, far from his family, where he felt like a small cog in a big wheel and decided that was not how he wanted to spend the rest of his career. Instead of a dramatic exit, he built a second engine on nights and weekends. He explains how he scored the top 300 metros to choose his markets, why he set a 15% cash-on-cash floor and walked past anything below it, and how he financed a growing portfolio three different ways as it scaled.

He goes deep on the two moves that made it work alongside a career. The first is operational: an operating system he calls manage the manager, which applied his corporate management skills to his property managers through weekly check-ins, clear performance goals, and a protocol for anything off-plan. The second is the tax strategy that took his federal rate from 35% to as low as 10% using real estate professional status and cost segregation. He is honest about what is conditional, including the household requirement behind the tax piece.

The close is the part most people skip past. Arthur admits he was so deep in his career that he almost lost himself in it, and that the real work was separating his identity from his title before he could build a next chapter that was actually his. This is a clear, specific look at how a high earner builds a parallel path to ownership without quitting first, and how he knew the moment the portfolio could replace the paycheck.

Chapters:
00:12 The nine-at-night moment at HP
00:18 The colleague who used the job as a means to an end
00:20 Set it and forget it: choosing buy-and-hold
00:27 The 15% cash-on-cash buy box
00:34 35% to 10%: the tax strategy and real estate professional status
00:44 Financing a portfolio three ways
00:52 Manage the manager: running 50+ units across three states
01:01 The retirement number: the math and the conversation
01:04 "I almost lost myself in tech", and the path out

Links:
Book Arthur Johnson 1-on-1: gravywealth.com/expert/arthurjohnson
Explore the Build pathway: gravywealth.com/build
Full transcript: gravywealth.com/podcast/arthur-johnson-assets-over-hours/transcript
Owner Mode Memo: gravywealth.com/memo
Owner Mode podcast: gravywealth.com/podcast
DNA Assessment: go.gravywealth.com/DNA
Arthur Johnson: linkedin.com/in/arthurj

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.

Tarrus Richardson grew up on the West Side of Chicago watching his parents buy businesses. He went to Harvard Business School, spent nearly a decade in institutional private equity, and then got fired and ended up near bankrupt by 2010, unable to get a single check written.

In this Owner Mode conversation, Tarrus breaks down how he came back. In 2014 he found a small IT staffing business in Pennsylvania, convinced the founders to sell only 51% and stay on as partners, got them to finance his portion with a seller note, pledged his house, and closed with no cash down. That first deal returned 4x. The third returned 27x.

He explains the ETA asset class, entrepreneurship through acquisition, and why stable cash flow businesses outperform venture-backed startups on a risk-adjusted basis. He breaks down how he raises capital deal by deal across an investor base of 149, roughly half of them accredited investors using 401(k) rollovers to get in, and how to evaluate the people who buy businesses before you back one.

This is a clear look at how a high earner builds a holding company one business at a time, and why the apprenticeship comes before the capital. As Tarrus puts it, he collects businesses.

Chapters:
00:00 "I collect businesses"
00:02 Brandon introduces Tarrus
00:10 West Side Chicago: a family that bought businesses
00:18 The apprenticeship: learning the game before owning anything
00:26 Wall Street, Harvard, and a decade in institutional private equity
00:34 The fall: fired, near-bankrupt, persona non grata
00:42 The comeback deal: 51%, a seller note, and a pledged house
00:54 The returns: 4x, then 15x, then 27x
01:02 How accredited investors back business buyers (401(k) rollovers)
01:08 Why stable cash flow beats startups
01:14 "That's called a job": ownership versus ageism

Links:
Explore the Acquire pathway: gravywealth.com/acquire
Full transcript: gravywealth.com/podcast/tarrus-richardson-overlooked-asset-class/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.

Kahlana Barfield Brown started as a six-dollar-an-hour intern and spent roughly a decade at InStyle, rising to Beauty Director. The job came with access most people never get: front row at the shows, every product on the market sent for free, meetings with the designers. In this Owner Mode conversation, she traces how she turned that access into an asset of her own.

For years the access felt like a perk that belonged to the magazine. When social media arrived and editors were still laughing at bloggers, Barfield Brown saw what the others missed: she already had the access those creators were chasing. She started a personal brand on it while still on payroll, treated her Instagram like her own magazine, and grew her partnerships until she was out-earning her salary on work the magazine's name was not attached to. The fear that almost held her in place was simple, that the relationships would disappear with the title. They did not. The phones rang after she left.

The second act is where the creator becomes a company. She walks through the infrastructure behind it, an agent to negotiate, a manager for strategy, an attorney for protection, and the four sold-out Target collections that gave her the confidence to launch on her own. After Target approached her about another collaboration, a mentor pushed her past it: the next thing you do, you need to own your brand. She did. KBB by Kahlana now sells in Target stores across the country.

The throughline is that the access your seat gives you is yours to build on, and the right time to start never arrives. For anyone who has spent years adding value to a company they do not own, this is a clear map of how to claim what is already theirs.

Chapters:
00:00 Will people answer the phone when I call?
00:09 Brandon introduces Kahlana Barfield Brown
00:14 The six-dollar-an-hour intern who slept on her sister's couch
00:22 Howard, her grandmother, and where the eye came from
00:34 The access nobody else had: shows, products, the designers
00:41 When editors laughed at bloggers, then bloggers sat in front of them
00:52 Treat your Instagram like your own magazine
01:08 The mentor who said: own your brand
01:14 Target and Future Collective: four sold-out collections
01:22 "Don't ever let this job be your identity"
01:30 No time is ever going to feel safe

Links:
Explore the Create pathway: gravywealth.com/create
Full transcript: gravywealth.com/podcast/kahlana-barfield-brown-your-access-is-an-asset/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.

Jewel Burks Solomon built Partpic, a computer vision AI startup, while working full time at Google, and sold it to Amazon in 2016. She is now Managing Partner of Collab Capital, a $125 million venture fund she co-founded.

In this Owner Mode conversation, Jewel breaks down a path to ownership that did not require burning everything down. She explains how she negotiated a role inside Google with no precedent, an entrepreneur-in-residence arrangement she made up with her mentor, that let her run the startup during business hours for three of the four years she spent building it. She funded the prototype with her own savings and won pitch competitions to meet the investors she wanted.

She describes the systematic way she read risk in her early twenties, mapping her downside rather than relying on bravado. She walks through the repositioning that landed the acquisition: stepping back from the public-facing role to push her technical co-lead onstage at the deep learning conference in Boston where Amazon was watching.

She also shares the second act, where 200-plus investor rejections during her own raise became the founding thesis of Collab Capital and her commitment to becoming the investor she never had. Before Collab, she ran Google for Startups in the U.S., deploying more than $45 million to Black and Latino-led businesses.

If you have a company idea and a job you are not ready to leave, this conversation is a concrete map for building on both sides of the table.

Chapters:
00:00 "I hated my job. It was awful."
00:05 Brandon introduces Jewel Burks Solomon
00:14 Family roots: entrepreneurship was all she saw
00:24 Goldman to Google: how Silicon Valley changed the plan
00:36 The entrepreneur-in-residence play: building Partpic on Google's payroll
00:48 Pitch competitions as investor prospecting
00:58 Repositioning the company to land Amazon
01:10 From exit to investor: why Collab Capital exists
01:18 The collaboration gap and closing philosophy

Links:
Explore the Launch pathway: gravywealth.com/launch
Full transcript: gravywealth.com/podcast/jewel-burks-solomon-founder-to-funder/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.