239: The Importance of Being Bold in Business, With Real Estate Mogul Dottie Herman

239: The Importance of Being Bold in Business, With Real Estate Mogul Dottie Herman

You don’t become the richest self-made woman in American real estate by playing it safe. Dottie Herman has proved time and time again that bold moves pay off. In the 1980s, in a maneuver that solidified her path to the top in real estate, Herman flew to California and convinced Merrill Lynch to hire her to help the company expand into the real estate market. In 1990, when Prudential decided to sell its regional holdings, Herman then persuaded the company to lend her $9 million to purchase its own Long Island real estate offices. And in 2003, Herman expanded her empire into New York City with the nearly $72 million purchase of the most prominent Manhattan real estate company, Douglas Elliman (again convincing Prudential to finance the deal). “If you don't ask, you don't know,” Herman says. “And the worst that can ever happen is someone says no.” Key Takeaways How Dottie Herman got into real estate Her bold move that convinced Prudential to lend her money to purchase one of its own companies How she weathered a recession while running her business The story behind acquiring Douglas Elliman, a prestigious real estate company in Manhattan Why she wanted to expand her real estate empire into New York City Her thoughts on branding How she maintains a good working relationship with her employees What she hopes to do next

Jaksot(583)

628: (Solo) The Content Playbook I Wish I Had When I Started

628: (Solo) The Content Playbook I Wish I Had When I Started

If you’re staring at an empty Instagram feed, TikTok account, or LinkedIn page thinking, “What the hell do I even post?”, this episode is for you. Every early-stage founder hits this wall — and most s...

3 Helmi 10min

627: How Lia Georgantis Built an Iconic Aussie Fashion Brand in Just 5 Years

627: How Lia Georgantis Built an Iconic Aussie Fashion Brand in Just 5 Years

Lia Georgantis took over a multi-brand fashion boutique with no business experience, lost most of her suppliers overnight, then rebuilt it into one of Australia’s most recognisable fashion brands by...

29 Tammi 56min

626: (Solo) Work Life Balance Is an Illusion. Here’s What Works Instead

626: (Solo) Work Life Balance Is an Illusion. Here’s What Works Instead

Most founders won’t say this out loud… work-life balance doesn’t really exist. At least not in the early years. I didn’t want balance — I was obsessed. I worked until 5 a.m., skipped sleep, skipped ho...

27 Tammi 10min

625: From $70M in Debt to $1B Amazon Deal in 45 Days | Jamie Siminoff

625: From $70M in Debt to $1B Amazon Deal in 45 Days | Jamie Siminoff

One billion dollars. That’s what today’s guest built — after being rejected on Shark Tank, nearly going bankrupt multiple times, and spending millions before making a single sale. In this video, Jam...

22 Tammi 53min

624: (Solo) How to Create More Than You Consume (Without Burning Out)

624: (Solo) How to Create More Than You Consume (Without Burning Out)

Most founders drown in content — YouTube, TikTok, newsletters, podcasts — but they rarely create anything themselves. And here’s the problem: consumption doesn’t build businesses; creation does. In...

20 Tammi 9min

623: $500K in Debt, 5 Maxed Credit Cards — How Jordan Harper Built an 8-Figure Brand in Year One

623: $500K in Debt, 5 Maxed Credit Cards — How Jordan Harper Built an 8-Figure Brand in Year One

Jordan Harper built an eight-figure skincare brand in its first year by maxing out five credit cards while already $500,000 in debt — and never raised a single dollar from investors. In this inter...

15 Tammi 53min

622: (Solo) The Truth About Founder-Led Content in 2026

622: (Solo) The Truth About Founder-Led Content in 2026

Founder-led branding isn’t dead — but it is evolving fast. Showing your face and posting “day in the life” content is no longer enough to stand out. The bar has risen, audiences have matured, and what...

13 Tammi 8min

621: We Bet $200K on Bras Before Making a Single Sale — Sold 400,000 in 2 Years | Nala

621: We Bet $200K on Bras Before Making a Single Sale — Sold 400,000 in 2 Years | Nala

Nala was built by two founders with no fashion background who invested $200,000 before making a single sale and went on to sell over 400,000 pieces in just two years. In this interview, Chloe and ...

8 Tammi 49min

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