Plunge into Prosperity

Episode 50 is a milestone! — Dr. Haley Medved Kendrick has spent her entire career unlocking capital for the founders everyone else overlooks. She's Senior Managing Director of Investment Accelerators at gener8tor — a platform that's worked with more than 2,000 startups that have gone on to raise billions — and a Principal of the gener8tor Alabama Fund, which she and her partner raised with a cap...

Caroline Ramos didn't leave corporate America. Corporate America left her. After fifteen years in marketing — an industry she describes as roughly 90 percent men, where she was frequently the only woman at the conference table — she was let go during COVID. As she puts it, the universe burned her boats. Six years later, the company she built from two Art Deco studios in Miami Beach is one of the t...

The wealth is coming. The performance is proven. And the allocation is still broken. By 2030, women in the United States are projected to control $34 trillion in investable assets. When you widen the lens to the Great Wealth Transfer — more than $100 trillion moving across generations in the coming years — women are positioned to inherit the majority. And yet women-led startups still receive rough...

98 percent of investment dollars in this country flow to 14 percent of the population. Breen Sullivan (Featured in Forbes & Harvard Business School Speaker) decided to take a hammer to that ceiling. In Episode 53, host Brandi Kolosky (Founder & GP of Sacral Capital, Sacral Fund I, & Sacral Sisters) sits down with Breen Sullivan — Founder & CEO of The Fourth Effect , the fastest-gro...

Vasanta Pundarika spent eighteen years as a healthcare investment banker. She started at Shattuck Hammond Partners, moved through Morgan Keegan and Raymond James, and co-founded the Healthcare Investment Banking Group at Matrix Capital Markets Group, advising on M&A, debt, and equity transactions from startups to multi-billion dollar companies. Then she quit and built Lotuspring — an advisory...

Melinda Powelson is the CEO of Match Engine — a platform business born out of one of the earliest lead-generation companies on the internet, and one that is now reinventing itself in real time. What started as a Denver recycling company founded by her father just after the first Earth Day has grown into a matching platform connecting customers and service providers across North America — spanning...

The fastest-growing cash-flow strategy in residential real estate isn't a flip. It isn't a short-term rental. It's renting the same house by the room — and while most people argued about whether co-living was a trend, Clara Arroyave was quietly building it into an asset class. In this episode of Plunge Into Prosperity, Clara — Founder and CEO of Coliving Cashflow — sits down with Brandi Kolosky to...

We spend most of this show with the founders and the builders. This episode, we sat down with an allocator — one of the people on the other side of the capital table, the person who decides where the money actually goes. Russ Lazaruk is a Portfolio Manager and Managing Director at NCP Digital Family Office, a multi-family office out of Victoria, British Columbia built on a genuinely different prem...

Reena Gupta is a serial technology founder who built her first company, Avankia, in 2002 — bootstrapped, no outside capital, right after the birth of her first child. She then built TargetRecruit, the first applicant tracking system for staffing companies inside the Salesforce ecosystem. She was incubated by Salesforce itself, and she exited it. She is now the Founder and CEO of Wisdocity — an AI...

She was married nineteen years. When she left, she took twelve boxes, bought an air mattress, and had to almost beg a stranger to believe in her enough to sign a lease — because her credit was a mess. Lana Hailemariam is the CEO and sole owner of StandUP, a leadership development company serving community-serving organizations from the American Red Cross down to the local nonprofits nobody outside...

Dr. Ashley Narain was working over 70 hours a week across two chiropractic practices when COVID shut down New York City. Instead of dreading the closure, she felt something she didn't expect: relief. That moment of clarity became the catalyst for Sinar Treatments, a luxury physical wellness practice in Midtown Manhattan where chiropractic, pain management, aesthetics, and acupuncture all exist und...

What happens when the person building AI for family office decision- making has also lived through three generations of family business, a second divorce, a solo move to London on her own visa, and twenty-six years inside Fortune 4 corporate innovation? You get Stacy Kehren Idema. In Episode 30 of Plunge Into Prosperity, host Brandi Kolosky sits down with Stacy — CEO and Founder of Equati and foun...

What happens when a large-scale IT project management executive becomes psychic, heals herself from seven years of mystery illness, and then builds a streaming television network from scratch with an all-female development team? You get Ellen Mahloy — CEO of Ethereal Networks, named TV Streaming CEO of the Year 2024 by CEO Monthly, and one of the most unconventional founders in media today. In thi...

It started as a tap on the shoulder. It ended as a sledgehammer. That's how Andrea De La Cerda describes the years-long arc that took her from 25-plus years on the agency side of advertising and marketing — building campaigns for brands like Honda, Nestlé, Pacific Life, and Wolfgang Puck — to packing up her life and her two dogs on February 5, 2026, and driving from Los Angeles to Salt Lake City t...

You Never Really Escape the Fear — You Change Your Relationship to It. That's the framing Tessa Santarpia, Founder and CEO of Santaia, brings into this conversation — and once you hear it, you can't unhear it. In Episode 27 of Plunge Into Prosperity, host Brandi Kolosky sits down with Tessa Santarpia, a Columbia MHA-trained healthcare operator turned founder, to talk about how our earliest money w...

What happens when you lose your marriage, your entire team, and every identity you ever built around other people — all in the same season? In this episode of Plunge Into Prosperity, Brandi Kolosky sits down with Jodi Koch — Founder and CEO of Elizabeth Erin Designs, creator of the Designing in 5D process, and host of her own podcast by the same name — for one of the most deeply personal conversat...

Brandi Kolosky sits down with Seth Levine — co-founder of Foundry ($4B AUM), partner at Quantum Advantage Capital, co-founder of Pledge 1%, and co-author of the national bestseller Capital Evolution. In this episode, Seth opens up the playbook on 20 years of venture capital — why Foundry was designed to close, what it means that 60%+ of VC dollars are concentrated in a handful of firms, and why th...

Elena Bondareva stood at a Moscow intersection at thirteen years old and watched a country collapse. Her college-professor parents were bartering on street corners. Everything she knew about value, security, and prosperity had just been stripped away. That moment became the seed for a career that has now spanned more than two decades, twenty ventures, and six countries. In this episode of Plunge I...

She started a company three months pregnant. Everyone thought she was insane. Now Maryann Chen, Founder and CEO of Kaasai, is about to close a contract worth £143 million over five years — and she did it without traditional venture capital. In this episode of Plunge Into Prosperity, Brandi Kolosky sits down with Maryann to unpack how her AI platform is automating data collection and management for...

She scaled LinkedIn's EMEA customer success operation from 35 million to 75 million in ARR. She built ESPN Digital's EMEA business from zero to 15 million in revenue. She worked inside LinkedIn, ESPN, Disney, Udemy, and the BBC. And then, after 20 years of building other people's visions, Kristin Nichols Isaac chose to plunge. In January 2025, Kristin co-founded Strudel AI — a Madison-based AI sta...

This is Sacral Sisters on the Record, Episode 4 — conversations with the women who are already inside the mission. Shannan Spann is a real estate expert & owner of Blue Elite Realty, wealth-building strategist, and founder of the Women's Wealth Building Network (WWBN) — a community platform dedicated to helping women build generational wealth through real estate, financial literacy, and the ki...

3 Turnarounds. $5.2M to $20M. The Money Mindset Nobody Teaches | Dr. Pamela Maraldo What if the secret to building wealth had nothing to do with finance — and everything to do with energy? Dr. Pamela Maraldo has led three major organizations through complete financial turnarounds. She ran Planned Parenthood Federation of America at the height of clinic violence, serving five million Americans a ye...

10 percent of board seats. 5 percent of media interviews. 2 percent of venture capital. This is the math against women in leadership. And it's not accidental. In Episode 19 of Plunge Into Prosperity, Brandi Kolosky sits down with Linda Fisk — Chairwoman, CEO & Founder of LeadHERship Global, President of CurvUp, and a U.S. Senator for the World Business Angels Investment Forum — to talk about w...

Angel Latterell took the plunge with 16 other women in the first round of the Sacral Sisters SPV. She is the founder of Latterell Law, a dual-state estate planning practice serving families in Washington and Florida. She is also a PMP, a Certified Scrum Master, a published poet, an Instructor of Project Management at the University of Washington, and a Certified Guide and Healer in the Lineage of...

She grew a dance fitness brand to over 300K YouTube subscribers and 2.4 million annual video views — with zero paid acquisition. Not one dollar in ads. All organic search, all content strategy, compounded over years. In this episode of Plunge Into Prosperity, Brandi Kolosky sits down with Charlene DiPaola, Founder and CEO of Hip Shake Fitness, to unpack how she went from managing million-dollar pa...