The Exit Whisperer

#74 - Lana Powers (Powers PR)

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 Powers
02:57 Hitting Rock Bottom As A Founder
03:57 Starting Powers PR From Scratch
05:17 Growing Slowly Into Real Momentum
06:15 Scaling While Pregnant With Twins
10:53 The Reality Of Running A PR Agency
14:58 Burnout In The Wellness Industry
15:54 Rebuilding The Business The Right Way
17:10 The Client That Changed Everything
18:50 Learning To Detach As A Leader
19:37 When Your Body Starts Breaking Down
22:35 How She Chose The Right Buyer
23:58 Life After Selling The Business
27:00 What Success Looks Like Now

#73 - Caren Sinclair-Kay (DoodleDeals)

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 Safety
06:01 Why Most Founders Make Bad Bets
07:54 The 2-Year Exit That Wasn’t What It Seemed
16:05 The Truth About “No Cash” Exits
20:43 Starting Again After Selling Too Soon
24:01 Why Salary Can Save Your Startup
24:36 The Partnership That Changed Everything
26:08 Raising Money Without Losing Control
26:55 Why Big Funding Can Kill Discipline
29:10 When Competition Turns Into Survival
32:24 The Lesson Most Founders Learn Too Late
33:41 How To Actually Pick A Co-Founder
36:08 The Mindset That Makes You Unbreakable

#72 - Rachel Sklar (TheLi.st)

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 Builder
03:05 Building The Li.st Before “Women’s Networks” Were Cool
06:09 Protecting Trust While Scaling
09:34 The Controversy
23:10 The Lessons Nobody Tells You
32:23 The “Perfect CEO” Idea (And The Plot Twist)
32:41 Startup Institute33:01 What The Li.st Could’ve Become
35:12 Pregnancy Changes The Timeline
36:30 COVID-19 Proves The Li.st’s Real Value
37:46 Handing Over The House You Built
52:30 Rachel’s Next Chapter After The Exit
58:54 What She’d Do Differently Now

#71 - Kristine Tonkonow (The Konery)

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 Tokonow
01:17 The Idea That Didn’t Exist Yet
02:19 From Side Hustle to Real Business
04:03 Scaling, Scrappiness, and Early Growing Pains
10:19 When COVID Hit the Business
11:21 Burnout, Pregnancy, and Pressure
13:30 Knowing It Was Time to Sell
14:15 Rebuilding Energy Before an Exit
15:27 Why 2021 Nearly Broke Everything
16:53 The Advisor Who Changed the Outcome
18:57 The Emotional Reality of Selling
20:04 The Day After It Was No Longer Hers
21:39 Letting Go and Walking Away
23:16 What Comes After the Exit

#70 - Roslyn McLarty (The GIST)

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 McLarty
04:18 Building The GIST From Scratch
05:08 Why Fundraising Was an Uphill Battle
07:24 Role Misalignment: The Silent Burnout Trigger
12:41 Hitting Burnout — And Finally Stopping
19:56 The Inner Critic That Won’t Shut Up
20:16 How Burnout Warps Business Decisions
21:22 The Emotional Whiplash of Leaving Your Company
22:19 Processing Grief, Relief, and Identity Loss
24:25 Finding Alignment After the Exit
26:16 Rebuilding Without Burning Out Again
29:50 How to Recognize and Regulate Burnout
33:44 What Every Founder Needs to Hear

#69 - Meghan Block (Wicked Good Mom Media)

Meghan built exactly the kind of business founders are told to want: flexible, profitable, and “lifestyle-friendly.” Then her 10-year-old assumed she’d be working at hockey practice — and she realized the business had quietly taken more than it ever gave back.
 
In this episode of The Exit Whisperer, Carrie sits down with Meghan Block, founder of Wicked Good Mom Media to unpack how a single local domain turned into a multi-market media company — and why scaling it further would’ve required giving up the one thing she wasn’t willing to lose: presence with her kids.
 
01:31 Meet Meghan Block: From Domain To Media Company
03:06 Building Wicked Good Mom Media
05:45 Scaling A Hyperlocal Business
10:06 The “Summer Of Mama” Reset
12:08 The Moment She Decided To Sell
12:59 Getting The Business Exit-Ready
15:01 Why Private Equity Wasn’t The Answer
15:27 Defining The Right Buyer
16:03 Protecting Financial Security After The Sale
16:17 Why She Refused A Long-Term Earnout
16:57 Finding The Buyer By Accident
18:15 When Family Becomes The Real KPI
21:35 The Boundary That Changed Everything
27:35 What’s Next After The Exit

#68 - Monika Kochhar (SmartGift)

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 andsold 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 Kocher
02:15 First Exit: Building And Selling Gugu Chew
04:08 How The Acquisition Came Together
07:15 Looking Back On The Gugu Chew Exit
08:56 Second Company: The Smart Gift Idea
11:04 Partnering With 1-800-FLOWERS
13:16 Why Advisory Boards Matter More Than You Think
13:57 Aligning Vision With Advisors Early
14:47 How COVID Changed Corporate Gifting Forever
15:15 Scaling Fast Without Losing Control
16:08 Inside The Acquisition Process
16:44 When Advisors Become Acquirers
20:34 Advice For Women Building Toward An Exit
23:43 Final Takeaways + How To Find Monica

#67 - Amanda Goetz (House of Wise)

In this episode of The Exit Whisperer, Carrie sits down with Amanda Goetz, founder of House of Wise and author of Toxic Grit, to unpack one of the most dangerous deal structures founders don’t talk about: the equity sale with no cash.
 
Amanda shares the full, unfiltered story of selling her fast-growing brand in an equity deal that looked “perfect” on paper — and how it quietly turned into a nightmare. We get into the emotional state founders are in when they sell, the paperwork everyone assumes gets handled, and the brutal reality of what happens when it doesn’t.
 
00:47 Meet Amanda Goetz
02:13 The Rise Of House Of Wise
02:42 Challenges In Fundraising
04:30 The Equity Deal (No Cash, High Risk)
04:43 When The Deal Started To Go Wrong
07:15 The Personal And Financial Fallout
10:28 Lessons Learned And Hard Advice
12:46 Decisions Made Under Pressure
13:39 Letting Go: Identity, Trauma, And Loss
14:38 When New Management Took Over
15:57 Starting Over: 2025 And Beyond
16:19 Finding New Roles And Creative Energy
16:57 From Newsletter To Book Deal
20:25 What “Toxic Grit” Really Means
23:17 The 10 Characters That Shape A Life

#66 - Gigi Lee Chang (Plum Organics)

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

#65 - Stacy Tasman Stahl (How He Asked)

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