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.

⏰ Timecodes ⏰

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