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.

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.

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.