The Exit Whisperer

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

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 than they feel, and how financial stress doesn’t just hurt your business… it distorts your judgment. They also get into choosing the right co-founder, raising from the right people, and why safety (not comfort) is the real prerequisite for smart entrepreneurship.03:31 The Moment She Walked Away From Safety06:01 Why Most Founders Make Bad Bets07:54 The 2-Year Exit That Wasn’t What It Seemed16:05 The Truth About “No Cash” Exits20:43 Starting Again After Selling Too Soon24:01 Why Salary Can Save Your Startup24:36 The Partnership That Changed Everything26:08 Raising Money Without Losing Control26:55 Why Big Funding Can Kill Discipline29:10 When Competition Turns Into Survival32:24 The Lesson Most Founders Learn Too Late33:41 How To Actually Pick A Co-Founder36:08 The Mindset That Makes You Unbreakable

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

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 sits down with Kristine, founder of The Conery, just days after selling the company she spent 12 years building from scratch. What started as a simple question — why are ice cream cones still terrible? — turned into a bootstrapped manufacturing business supplying major brands, theme parks, and retailers.00:50 Meet Kristine Tokonow01:17 The Idea That Didn’t Exist Yet02:19 From Side Hustle to Real Business04:03 Scaling, Scrappiness, and Early Growing Pains10:19 When COVID Hit the Business11:21 Burnout, Pregnancy, and Pressure13:30 Knowing It Was Time to Sell14:15 Rebuilding Energy Before an Exit15:27 Why 2021 Nearly Broke Everything16:53 The Advisor Who Changed the Outcome18:57 The Emotional Reality of Selling20:04 The Day After It Was No Longer Hers21:39 Letting Go and Walking Away23:16 What Comes After the Exit

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