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

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 Professional Athletes
8:10 Supporting Exonerees With Their Financial Needs
10:50 Considering Leaving The Firm For Personal Reasons
12:33 Learning To Parent A Special Needs Child
14:00 Concerns Over A Partner’s Financial Decisions
17:40 Realizing It Was Time To Leave The Partnership
18:40 Embracing Full Independence In Her Business
20:00 Clients Rallying Behind Her During The Transition
21:40 Negotiating Exit Terms With Her Business Partner
24:28 Selling A Portion Of The Business
25:07 Acquiring Additional Wealth Management Firms
27:54 Lessons Learned From Business Partnerships
29:50 The Importance Of Strong Financial Planning

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 Business Deal
5:38 How Acorn Grew During The CEO Society Era
6:24 Launching Oak’s Email Studio
8:14 Splitting Brands To Stay Focused
10:40 The Unexpected Offer To Buy Oaks
11:20 Why Agencies Want To Acquire Email Agencies
12:01 Trusting Your Gut During Negotiations
12:44 The Challenge Of Untangling Finances
15:30 Evaluating The True Value Of A New Brand
16:45 Wrestling With Seller’s Remorse
17:38 Selling Potential Versus Selling Historical Data
19:12 Transitioning Into Life After The Sale
20:25 Launching A Mentorship Program
22:36 Advice For Women Building Their Businesses
24:00 Why The Right Hire Changes Everything
27:03 Details On The Growth Season Mentorship Program

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.

2:10 Choosing To Stop Chasing A Career At Google
6:25 An Unexpected Job Offer Mid-Flight
8:14 Learning The Basics Of Venture Capital
10:05 Building Powerful Relationships In Pharma
11:49 Closing Her First Million-Dollar Pilot Deal
14:32 Launching Her YouTube Channel Back In 2014
17:00 Why Timing And Vision Matter In Startup Success
18:52 The Power Of Emotion In Marketing
21:49 Facing Cardiac Arrest Again At Age 32
24:14 Realizing Health Must Come First
27:10 Why You Should “Date” Your Investor
30:10 Learning To Let Go So The Business Can Grow
32:44 What She Learned From Acquiring A Company
34:41 Launching A Foundation To Support Entrepreneurs
37:43 Honest Reflections On The Entrepreneurial Journey
40:02 Key Advice For Aspiring Entrepreneurs
42:04 Why Every Founder Needs A Therapist

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.

2:32 How 11Outof11 was born from freelancing burnout
4:42 Leaving the commute and daycare guilt to go all-in on freelance
7:13 Designing an agency with a future sale in mind
9:50 The hardest step — deciding to buy out her partners
13:06 Third-party valuation, bank loans, and emotional fallout
15:32 Relief, confidence, and revenue skyrocketing post-buyout
18:51 Why she chose to sell just one year later
22:23 Choosing the right buyer and securing a 90-day transition
24:45 No regrets and closing the deal during her son’s graduation week
27:04 Fractional CMO life, building a mountain home, and family time
30:18 Learning to slow down after witnessing friends survive cancer
32:00 Why Angela’s real-world exit story matters

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.



5:48 Why Selling the Business Felt Like a Dream Come True
8:01 How the Company Grew Rapidly During the Pandemic
9:59 Knowing It Was the Right Time to Sell
11:30 Shifting Her Focus Into a New Business Venture
14:10 Her Deep Obsession With Cannabis Dosing
16:11 Making the Final Decision to Sell
19:02 The First Meeting With a Business Broker
21:19 The Game-Changing Email From a Potential Buyer
22:57 The Hidden Challenges of Planning an Exit
26:04 Why You Always Need Multiple Interested Buyers
27:53 Mastering the Art of Negotiating Deal Terms
30:22 Renegotiating Terms Even After the Deal Is Struck
32:54 How She Created Predictability in Her Payments
34:32 The Current Success of Mary and Jane
37:25 The Hard Realities of Growing a Business