The Exit Whisperer

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 by Dubsado. Dubsado helps service-based business owners streamline proposals, contracts, invoices, payments, and client workflows all in one place. Visit www.dubsado.com and use code WHISPER for 30% off.2:47 - How Dubsado Got Started7:00 - Working with Your Spouse7:39 - The Blessings & Challenges of Building a Business with Your Spouse13:48 - Bootstrapping a Tech Business19:13 - Planning for Exit23:14 - Navigating the AI & Tech Landscape24:37 - Burnout & Year Nine

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, Wealthrive, and The Luckey Capital Group — partners helping founders streamline their businesses, plan their wealth, protect more of what they earn, and access capital when they need it.0:49 - Building The Whisper Group1:37 - Crossing the 7-Figure Milestone4:17 - The Whisper Group & Advisor Model4:51 - Renaming the Community: Acquired Not Retired6:43 - Podcast Updates & Why She Added Sponsors8:58 - Sponsor #1: Wealthrive 10:21 - Sponsor #2: Theory Planning Partners12:07 - Sponsor #3: Dubsado14:00 - Life on the Road & Speaking Tour16:02 - On Conviction & Pushing Through Hard Days

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 actually feels like after the applause stops.01:09 Meet Natalie Mackey02:44 The Pivot That Changed Everything05:15 Why Beauty Breaks E-Commerce Rules07:25 The Product That Took Off Overnight08:09 Fundraising Is Timing, Not Talent13:06 The Decision to Sell Instead18:22 The Truth About “Winning” an Exit19:07 Why the Second Time Feels Different20:38 AI Is Giving New Founders an Edge21:30 Losing the “Founder” Identity24:45 The Pressure to Do It Again26:33 Why You Just Have to Start28:00 Money, Risk, and Never Feeling Safe30:18 The Traits That Actually Matter

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 healthy.” Lana also opens up about the aftermath of selling, the second-guessing, the “what if I kept going,” and redefining success beyond revenue, status, or control.00:56 Meet Lana Powers02:57 Hitting Rock Bottom As A Founder03:57 Starting Powers PR From Scratch05:17 Growing Slowly Into Real Momentum06:15 Scaling While Pregnant With Twins10:53 The Reality Of Running A PR Agency14:58 Burnout In The Wellness Industry15:54 Rebuilding The Business The Right Way17:10 The Client That Changed Everything18:50 Learning To Detach As A Leader19:37 When Your Body Starts Breaking Down22:35 How She Chose The Right Buyer23:58 Life After Selling The Business27:00 What Success Looks Like Now

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), why “perfect-fit” acquisitions die when you wait too long, what happens when the buyer’s lawyer kills the vibe, and why sometimes the smartest deal is the one that lets you sleep at night — even if it’s not the biggest number.02:25 Meet Rachel Sklar: The Original Community Builder03:05 Building The Li.st Before “Women’s Networks” Were Cool06:09 Protecting Trust While Scaling09:34 The Controversy23:10 The Lessons Nobody Tells You32:23 The “Perfect CEO” Idea (And The Plot Twist)32:41 Startup Institute33:01 What The Li.st Could’ve Become35:12 Pregnancy Changes The Timeline36:30 COVID-19 Proves The Li.st’s Real Value37:46 Handing Over The House You Built52:30 Rachel’s Next Chapter After The Exit58:54 What She’d Do Differently Now

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 founders don’t post: the eye twitch, the dread, the “take a long weekend” advice that solves nothing, and the moment you realize it’s not just hard — it’s misaligned. Roslyn breaks down what burnout actually is (a chronically activated nervous system), how to tell “push through” from “get out,” and why chasing outcomes (revenue, valuation, the headline) is the fastest route to losing yourself.02:19 Meet Roslyn McLarty04:18 Building The GIST From Scratch05:08 Why Fundraising Was an Uphill Battle07:24 Role Misalignment: The Silent Burnout Trigger12:41 Hitting Burnout — And Finally Stopping19:56 The Inner Critic That Won’t Shut Up20:16 How Burnout Warps Business Decisions21:22 The Emotional Whiplash of Leaving Your Company22:19 Processing Grief, Relief, and Identity Loss24:25 Finding Alignment After the Exit26:16 Rebuilding Without Burning Out Again29:50 How to Recognize and Regulate Burnout33:44 What Every Founder Needs to Hear

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 in what most founders get wrong: thinking exits are transactions, not long-term relationships. Monica breaks down why partnering before you sell can be the difference between a smooth exit and a cultural disaster, and why letting a potential acquirer see your company up close is not weakness, it’s leverage.01:00 Meet Monica Kocher02:15 First Exit: Building And Selling Gugu Chew04:08 How The Acquisition Came Together07:15 Looking Back On The Gugu Chew Exit08:56 Second Company: The Smart Gift Idea11:04 Partnering With 1-800-FLOWERS13:16 Why Advisory Boards Matter More Than You Think13:57 Aligning Vision With Advisors Early14:47 How COVID Changed Corporate Gifting Forever15:15 Scaling Fast Without Losing Control16:08 Inside The Acquisition Process16:44 When Advisors Become Acquirers20:34 Advice For Women Building Toward An Exit23:43 Final Takeaways + How To Find Monica

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 Chang04:17 The Idea Behind Plum Organics07:26 Early Challenges Building The Brand10:39 The Pouch That Changed The Category22:07 The Shift To Plum As The Core Brand22:55 Looking Back On The Decision25:01 When Gigi Lost Control Of The Company25:48 How Investors Actually Think28:15 Selling Plum Organics To Campbell’s29:20 Life After The Acquisition30:32 Entrepreneur Vs Small Business Owner41:18 What Gigi Is Building Now

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, Dealmaker02:22 The Thanksgiving Idea That Sparked Digital Brand Architects04:03 How DBA Helped Invent The Creator Economy Before Instagram07:04 Knowing When To Walk Away—And Start Over08:10 Why “Trust” Became The Non-Negotiable Business Principle14:20 Inside The CAA Acquisition18:36 When The Deal Looks Good—But The Reality Doesn’t20:52 The Moment Everything Had To Change21:20 Redefining Failure: Pivots, Pressure, And Perspective22:41 Journaling, Self-Awareness, And Founder Survival Tools24:32 Rebuilding With Intention: The Real BrainTrust Vision25:12 From Agency To Studio To Fund26:39 Corporate Partnerships, Power Dynamics, And Hard Truths29:57 New Ventures, New Partners, And Building With Exit In Mind35:39 From Hustle To Harmony: Success, Sleep, And The Next Chapter

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 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

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

What do you do when you raise venture money… and then realize it’s not the right path? For Elle Hempen, co-founder of The Atlas, the answer was bold: sell just one year later. In this episode, we talk about how a Google spreadsheet turned into a tech company, why she decided to skip the long VC grind, and how she negotiated an exit during the chaos of COVID. From pitching at Y Combinator while 8 months pregnant to getting a cold email from the exact company she dreamed of selling to, Elle’s story is packed with twists, hard choices, and the kind of honesty you rarely hear in startup land. 2:11 Why Valuing Early-Stage Tech Companies Is So Critical 5:00 Building the Atlas Platform From a Real-World Problem 6:34 Launching the First Version Back in 2016 9:06 Creating a Strong, Scalable Data Infrastructure 10:54 Deciding It Was Time to Fundraise for Growth 12:29 Applying to Y Combinator to Fuel Expansion 15:06 Fundraising in the Middle of a Market Crash 17:01 Finding the Right Strategic Investor 20:41 Soul-Searching to Determine the Company’s Direction 23:12 Valuing the Business Based on Future Potential 25:47 Celebrating a Rare and Remarkable Tech Achievement 29:02 Reflecting on Five Years of Building and Learning 30:40 Exploring What’s Next After the Exit 32:23 The Unique Energy of Being an Entrepreneur 34:40 Is an MBA Worth It for Founders? 36:57 Aligning Education With Real Business Needs