The Exit Whisperer

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 faster… and watching the cap table quietly decide what you “walk away with.” We talk about the pouch pivot that changed the category, the behind-the-scenes reality of board power, and the uncomfortable truth that “entrepreneur” became a status badge — not a job description.

02:52 Meet Gigi Lee Chang

04:17 The Idea Behind Plum Organics

07:26 Early Challenges Building The Brand1

0:39 The Pouch That Changed The Category

22:07 The Shift To Plum As The Core Brand

22:55 Looking Back On The Decision

25:01 When Gigi Lost Control Of The Company

25:48 How Investors Actually Think

28:15 Selling Plum Organics To Campbell’s

29:20 Life After The Acquisition

30:32 Entrepreneur Vs Small Business Owner

41:18 What Gigi Is Building Now

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 your business is only worth what you’re willing to sell it for.

01:09 Meet Stacy Stahl

02:37 The Idea That Started How He Asked

03:34 Going Viral Before “Going Viral” Was A Thing

05:32 How The Knot Came Into The Picture

09:38 The Lowball Offer, The Counter, And The Power Shift

16:04 Why She Started Her Second Company Anyway

20:06 When The Easy Path Disappears

20:45 Jumping From Digital To Product — On Purpose

22:57 Building A Business During COVID

23:49 The Pivot That Changed Everything

24:57 Breaking Into The Promotional Products World

26:59 Running A Business Without Burning Out

29:31 Why Simple, Profitable Businesses Win

32:01 Building Success And Bringing Others With Her

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 back, building BrainTrust into a studio + fund backing Black beauty & wellness founders, and why corporate partners suddenly got nervous about “Black founder” the second it became inconvenient.

01:36 Meet Kendra Bracken Ferguson: Builder, Operator, Dealmaker
02:22 The Thanksgiving Idea That Sparked Digital Brand Architects
04:03 How DBA Helped Invent The Creator Economy Before Instagram
07:04 Knowing When To Walk Away—And Start Over
08:10 Why “Trust” Became The Non-Negotiable Business Principle
14:20 Inside The CAA Acquisition
18:36 When The Deal Looks Good—But The Reality Doesn’t
20:52 The Moment Everything Had To Change
21:20 Redefining Failure: Pivots, Pressure, And Perspective
22:41 Journaling, Self-Awareness, And Founder Survival Tools
24:32 Rebuilding With Intention: The Real BrainTrust Vision
25:12 From Agency To Studio To Fund
26:39 Corporate Partnerships, Power Dynamics, And Hard Truths
29:57 New Ventures, New Partners, And Building With Exit In Mind
35:39 From Hustle To Harmony: Success, Sleep, And The Next Chapter

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 hear how the Whisper Group is evolving—from advisory to brokerage—and why selectivity is a competitive advantage when helping women navigate how to sell a company. If you’re building with an exit in mind or questioning whether you’re truly prepared for selling a business, this conversation will reshape how you think about female entrepreneurship and women founders exits.

00:00 Season 6 begins: why this chapter is different

00:43 The rise of women-owned businesses and the movement behind it

01:28 A major announcement: bringing on a co-founder

01:56 What actually matters when choosing the right co-founder

03:06 New upgrades, merch, and what’s evolving this season

03:23 Why we’re prioritizing in-person podcast conversations

03:43 Expanding into brokerage — with intention and restraint

05:12 The hidden cost of growth: expenses and pressure

05:41 Letting go of scarcity thinking while scaling

06:56 Why I’m genuinely excited about what’s ahead

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.

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.

In this raw and unfiltered interview, Sharmin Ali shares how a chance encounter on a flight changed her life forever. From joining a startup that became a unicorn to surviving a cardiac arrest at 32, she reveals what founders never talk about: burnout, bad investor deals, and the price of ambition.

Angela Pointon opens up about what it’s really like to buy out your partners, take on debt, and bet on yourself when everything’s on the line. From the hardest conversations to the relief of letting go, this episode is about courage, burnout, and knowing when to walk away—on your own terms.

Ever felt stuck running a business you no longer love—but you’re scared to let go? Meet Laura Roos, who sold her company without a broker, while pregnant, and turned the proceeds into her next seven-figure startup. This episode is messy, honest, and full of real talk about what it actually takes to walk away.

What happens when the person running your company with you ends up buying it from you? Carey Linderman shares how she went from senior care to creating an entirely new category: the postpartum doula. And how she built a business that supported moms when no one else did, and why she ultimately decided to sell her company to her own #2.