The Exit Whisperer

KK Hart shares her unconventional path from corporate life to building and acquiring multiple businesses with no debt and no outside capital. This episode explores cash flow, wealth building, family, acquisitions, and what happens when a founder stops waiting for an exit to create freedom.   This episode is sponsored by Wealthrive.  Wealthrive helps business owners keep more of what they earn thro...

Kaitlyn Carlson from Theory Planning Partners joins Carrie Kerpen for a powerful conversation about money, values, and preparing for the exit of your dreams. From surviving toxic power dynamics in wealth management to building a financial planning firm rooted in honesty and advocacy, Kaitlyn breaks down what founders should be thinking about long before they sell.   This episode is sponsored by Th...

Gesche Haas joins  The Exit Whisperer  just before selling  Dreamers & Doers , the women entrepreneur community she built over 12 years. She shares how she grew it without outside funding, why the right buyer mattered, how SBA financing helped shape the deal, and what founders should consider when an exit becomes personal.   This episode is sponsored by  The Whisper Group , helping women found...

Marina Khidekel joins Carrie Kerpen just days after selling Hugimals to Relatable. She shares how she built a design-forward weighted plush brand from the ground up, bootstrapped it to seven figures, chose control over outside funding, and navigated the reality of selling her company while stepping into a new role with the buyer. This episode is sponsored by The Whisper Group , helping women found...

Sherrell Dorsey joins Carrie Kerpen to share her journey of transforming a newsletter into a data-driven media company that highlights Black innovation, underrepresented founders, and the business stories that traditional media overlooked. This episode explores founder burnout, media entrepreneurship, data as a business asset, market timing, team leadership, and the emotional complexity of selling...

Becca Berg, co-founder of Dubsado, shares how a chaotic moment in her photography business became the spark for building one of the most beloved systems for service providers. Carrie and Becca talk about client experience, scaling with your spouse, the sacrifices behind fast growth, and what it really takes to build a business that feels both beautiful and functional.   This episode is sponsored b...

Alex Schinasi, founder of Hulken, joins Carrie Kerpen to unpack the real entrepreneurial journey behind raising venture capital, pivoting under pressure, selling companies, and building again. From Ivy to Hulken, Alex shares why billion-dollar valuations do not always mean founder freedom, how pivots create momentum, and what it means to be truly “acquired, not retired.” This episode is sponsored...

Carrie Kerpen kicks off Season 7 of The Exit Whisperer with a raw behind-the-scenes look at building The Whisper Group after selling her first company.  From crossing the seven-figure mark to managing cash flow, Carrie opens up about what it really feels like to start again, scale again, and build another business after an exit. This season is supported by  Dubsado ,  Theory Planning Partners ,  W...

In the first live recording of The Exit Whisperer at Luminary, Suneera Madhani shares how she turned a rejected idea into one of Florida’s biggest startup success stories. At 25, she pitched a subscription-based payment processing model to her employer. They passed—so she quit, moved back home, teamed up with her brother, and built Stax from scratch. Suneera breaks down what it really took to scal...

Natalie built a wildly recognizable beauty brand, raised $13 million, got it into major retail, and still came away with the same uncomfortable realization a lot of founders quietly have: the number in the headline and the money you actually feel are not the same thing. This isn’t a Cinderella story. It’s what happens when a smart founder tells the truth about money, control, and what an exit actu...

In this episode of The Exit Whisperer, Carrie sits down with Andrea Johnston, founder of Pure Communications, to unpack what most founders never say out loud: sometimes the business is thriving, the numbers are strong, the offers are real, and you still know it’s time to sell. They get into building with intention, why niche agencies scale faster than scattered ones, what private equity actually w...

In this episode of The Exit Whisperer, Carrie sits down with Lana Powers (founder of Powers PR) to unpack a truth most founders ignore until it’s too late: success can still be the wrong path if it’s killing you to sustain it. They get into rebuilding a company just to make it sellable, why hitting a peak can be more dangerous than failing, and how founders confuse “being needed” with “being healt...

In this episode of The Exit Whisperer, Carrie sits down with Caren Sinclair — a serial founder, operator, and dealmaker who has sold multiple businesses and is honest enough to say the quiet part out loud. Caren breaks down what founders rarely admit in public, how early investor pressure can push you into deals you wouldn’t choose in a stronger position, why equity-only exits often sound better t...

Rachel Sklar built the most powerful women-in-tech network before “women’s communities” were trendy. In this episode of The Exit Whisperer , Carrie Kerpen sits down with Rachel, founder of The Li.st, to unpack the kind of exit founders never brag about — because it’s not a flashy SaaS story. They get into the messy parts people skip: charging for community (hello, “pay to be her friend” headlines)...

Kristine Tokonow bootstrapped her way into major retailers and global brands, survived COVID, supply chain chaos, labor shortages, pregnancy, and a year that pushed her to the edge. She knew she was burned out in 2021 — but she didn’t sell then. Instead, she rebuilt, stabilized, and intentionally positioned the company to be worth walking away from. In this episode of The Exit Whisperer , Carrie s...

Selling your company isn’t always a flex. Sometimes the bravest exit is walking away. If you’re “fine” but your body is screaming, this episode is for you. In this episode of The Exit Whisperer, Carrie sits down with Roslyn McLarty, co-founder of The GIST, who left a fast-growing, funded company when burnout stopped being a vibe and started being a warning sign. We get into the unsexy truth founde...

Meghan built exactly the kind of business founders are told to want: flexible, profitable, and “lifestyle-friendly.” Then her 10-year-old assumed she’d be working at hockey practice — and she realized the business had quietly taken more than it ever gave back. In this episode of The Exit Whisperer , Carrie sits down with Meghan Block, founder of Wicked Good Mom Media to unpack how a single local d...

Most acquisitions fail because founders obsess over the price — not the people. Monica Kocher built and exited two companies by doing the opposite. In this episode, Carrie sits down with Monica, a rare founder who bootstrapped and sold twice — once through a strategic partnership that became an acquisition, and once through an advisory relationship that turned into a buyer. This is a masterclass i...

In this episode of The Exit Whisperer, Carrie sits down with Amanda Goetz, founder of House of Wise and author of Toxic Grit, to unpack one of the most dangerous deal structures founders don’t talk about: the equity sale with no cash. Amanda shares the full, unfiltered story of selling her fast-growing brand in an equity deal that looked “perfect” on paper — and how it quietly turned into a nightm...

Your “dream exit” is probably a math problem you haven’t done yet. Gigi Lee Chang built Plum Organics to a reported nine-figure exit to Campbell Soup Company — then tells the part founders don’t talk about: dilution, losing control, and why the headline is rarely what hits your bank account. In this episode, Carrie Kerpen sits down with Gigi Lee Chang to unpack the real trade: raising money to go...

The first offer was three times too low — and Stacy Stahl almost walked away. Instead, she did something most founders never do, and it changed the entire deal. In this episode, Carrie sits down with Stacy Stahl (founder of How He Asked — yes, the “Gossip Girl of proposals” — acquired by The Knot) to break down the part founders don’t post: the lowball, the power move, and the moment you realize y...

Kendra Bracken Ferguson built companies that invented the creator economy before Instagram and TikTok — and she tells the part founders unusually hide: when the shiny acquisition stops working, the earn-out math gets ugly, and you have to choose between protecting your title or protecting your team… We get into trust as a system (including her very controversial co-founder test), buying a company...

In this solo episode, Carrie pulls back the curtain on what it actually takes to build an exit strategy for women founders—from choosing the right co-founder to expanding into brokerage without chasing growth for growth’s sake. She explains why so many women struggle with confidence during the exit process and how mindset, timing, and preparation directly impact business valuation. You’ll also hea...

In this episode, Nicole opens up about the hardest year of her life, balancing motherhood, money, and a messy business breakup, and how she found the strength to start over and build something entirely her own. 2:02 Nicole’s Journey Into Wealth Management   5:37 Transitioning Into An Independent Advisory Firm   6:27 Stepping Fully Into The Independent World   7:34 Building A Niche Focused On Profe...

In this episode, Molly Nutt shares how she pulled off two very different exits, what she learned about selling potential vs. profit, and how to protect your relationships when business gets personal. If you’ve ever wondered how founders actually navigate the messy, emotional side of selling, this is the one to listen to.    2:34 Starting The CEO Society   4:44 Creating A Friendship Clause In A Bus...