Sorta Bossy

A listener went to their first conference alone. They wanted to meet people. They left without starting a single conversation, and now they wish they had.

Emily says she could have written this Dear Bossy herself. She and Adrienne talk about why almost everyone in that hallway feels the same way, and what to do differently next time.

What they cover:

• Why the people on their laptops between sessions are just as nervous as you are
• What event hosts owe their attendees, and where your own responsibility starts
• The one small commitment that makes you look approachable between sessions
• Treating rejection like practice, and why most groups will welcome you in
• Emily’s first event as a team member, and why the pressure to bring something back to work made her raise her hand every time
• Why Emily has no fear hosting a panel but freezes walking up to a group
• Easy openers: a compliment, someone’s book, a good question from the last session, the speaker’s talk, the catered food
• Deciding before you go what you want out of the trip
• Why in-person connection is the golden ticket right now

Submit your Dear Bossy question here.
Get on the Bunk List for Camp OOO here.

⏱️ Time Chapters
00:00 Welcome and the big meanie story
04:35 Dear Bossy: alone at your first conference
09:15 Put the phone away
14:25 Easy icebreakers for introverts
18:40 Why did you even go?

Camp took a year off. The campers were not thrilled.

But the break gave Adrienne and Emily time to rebuild it from the ground up, and now it is back with a new name and a clear reason to exist.

In this episode, Adrienne and Emily announce Camp Out of Office, a women-only camp for female founders and team leads, happening in Nashville in September 2027. They get into why the best ideas never show up in your session notes, and why stepping away is the fastest way to find out what breaks.

What they cover:

• How a camp job Adrienne once hated taught her the difference between a hard job and the discomfort of being new
• Why events are booming again, and why people are waiting longer than ever to commit (via events expert Julius Solaris)
• Camp as a test run: unplug for a few days and see what actually breaks in the business
• Why the most valuable conversations at any event happen in the in-between moments
• The post-conference whiplash that leaves teams scrambling
• The honest downside: it is summer camp food
• Why camp is women-only this time, and how to get founder spots first through the Bunk List

Get on the Bunk List for first access to founder spots: imgoingtocamp.com

Interested in sponsoring camp? Reach out to Adrienne on Instagram.

Time Chapters
00:00 Summer camp, then and now
06:50 The golden era of events
11:05 Camp Out of Office is back
16:55 The best ideas happen in between
21:35 The Bunk List, founder spots, and Nashville
26:30 The worst part of camp: the food
30:50 Sponsors, and why camp is just for the girlies

Adrienne and Darrell Vesterfelt spent a year and a half trying to get operators into one room together. This fall they finally planned the event. 9 people committed, and they had to cancel it.

Adrienne and Emily walk through the whole decision, from setting the cutoff to sending the refund email, and what happened when the operators who signed up asked to stay connected anyway.

What they cover:

• Why the operator role sits in isolation, with no peers above them, no peers below them, and a founder with a completely different skill set
• Founders put money into their own coaching, masterminds, and peer groups, and usually nothing into their number 2
• The cutoff: why Adrienne wouldn't run the room with fewer than 15 people when 35 were promised
• Sending the refund email, and the response from operators that changed what happened next
• How the free Operators Only Slack community got 15 applications on day 1
• The system everyone on the team follows except the founder
• Why Adrienne would rather be embarrassed than run an event she couldn't deliver on

Send this to your operator: joinoperatorsonly.com

Time Chapters
00:00 Disney princesses and starter marriages
07:40 We cancelled our event
11:50 Why the room didn't fill
16:05 The email nobody wants to send
20:55 15 applications on day 1
27:20 Integrity over embarrassment

An interviewer went online and said they passed on a candidate for bringing an iced coffee to the interview. The internet split in half. Adrienne's gut said absolutely not, and then she had to figure out why.

Adrienne and Emily get into #icedcoffeegate26 and the professionalism rules most of us picked up without ever deciding we believed them.

What they cover:

• Why Adrienne would still tell you to skip the iced coffee, and how her reason changed once she questioned her first reaction
• The rule Adrienne uses for interviews, sales pitches, investor meetings, and keynotes: don't let anything distract from your goal in that room
• Where so many professionalism rules come from, and why Emily thinks Gen Z deserves some slack
• A rapid fire round on baseball hats, AirPods, phones on the table, eating on Zoom, cameras off, shorts at the office, lowercase emails, and swearing in client meetings
• Why a sip of water can help you in an interview, and why Emily would turn down the free coffee
• The question to ask about any rule in your business: is this what I believe, or something I adopted without thinking about it?

Connect with Adrienne on Instagram

Time Chapters
00:00 Welcome and the early release Monday mystery
04:05 Iced coffee gate 2026
09:25 The real problem is the distraction
14:05 Who made these rules anyway?
18:40* Rapid fire: professional or who cares?
22:50* Water, free coffee, and the double-double
27:00 Question the rules you inherited

Most founders think they have two options:

1. Keep grinding
2. Shut it down and go get a job.

Steve Guberman was one week from taking a corporate offer when his brother stopped him. After spending a decade building his own agency, Steve made an acquisition with no money in the bank, sold the business after the worst year of his life, and now advises agency founders on mergers, acquisitions, and exits.

He hosts the Agency Bytes podcast and has coached more than 100 agencies. In this episode he and Adrienne open up the part of business ownership that usually happens behind closed doors.

What they cover:

• How Steve acquired a competitor's book of business with zero cash, using a commission structure paid out over two years
• What an acquihire is, and why a burnt out founder often wants to become your employee
• Why hiring a salesperson almost never works under seven figures, and what to buy instead
• The difference between an entrepreneur and an accidental business owner, and how to tell which one you are
• The RFP his six person agency never should have won, and the year that followed
• Nine pitch meetings, three offers, and the sale he almost never made
• Why he begs founders not to shut it down, even when the exit is not life changing money
• Merger versus acquisition in plain language, plus how a seller keeps equity for a second bite
• Why 25% growth is a good year, and one deal can add 40%

Connect with Steve:

Steve Guberman is the founder of Agency Outsight, where he helps agency owners build the business of their dreams—with clarity, purpose, and profit. A former agency founder who successfully exited his own firm, Steve now guides creative, marketing, and digital leaders through growth, positioning, and the complex decisions that come with scaling or selling an agency. Drawing on his experience as both a coach and M&A advisor, he helps owners understand what truly drives long-term value—financially and personally. As host of the Agency Bytes podcast, Steve shares real stories and lessons from top agency leaders to help others grow with intention.

Steve on LinkedIn: https://www.linkedin.com/in/agencycoach/

Agency M&A Liftoff, Dallas, November 4 to 6: https://liftoffconference.com/

Free agency resources: https://www.agencyoutsight.com/merge

Podcast: Agency Bytes

⏱️ Time Chapters

00:00 Meet Steve Guberman
01:08 Founder optionality
04:41 The acquisition he made with no money
06:35 What an acquihire actually is
07:15 Why hiring a salesperson rarely works
08:12 Accidental business owner or entrepreneur
11:55 Do it again, and again, and again
12:55 The one third rule
13:25 Don't build the department, buy it
16:45 Does your house need to be in order first
17:40 The consolidation happening right now
19:45 The RFP they never should have won
20:55 The year everything came apart
22:05 I'm going to run this thing until I die
22:35 Get a job or sell it
23:05 Nine pitches, three offers
24:30 Offering the business to his team
25:20 The folder on Eric's desktop
26:05 A three year succession plan in action
27:55 The dentist and the dog food website
30:20 Three years of clean books
31:25 What a well run business is actually worth
34:05 Why these deals happen behind closed doors
35:10 Merger versus acquisition, explained
36:25 The second bite
42:20 25% growth versus one deal
43:20 Lift Off in Dallas
45:50 Where to find Steve

Adrienne has a warning for anyone chasing seven figures: revenue isn't the same thing as an asset.

In this episode, she walks through the seven signs that you've actually built yourself a very well paying job, and Emily pushes back on more than a few of them.

The two dig into what separates a business that can survive without its owner from one that's just a job with better margins, and why most people don't act on it until the pain gets too big to ignore.

What they cover:

• Why revenue is a marketing tool, not proof you've built something valuable
• Sign one: you still approve everything, even after hiring expensive help to stop doing that
• Sign two: clients are buying access to you specifically, not a system that delivers without you
• Sign three: you can't disappear for four weeks without still checking your phone
• Sign four: revenue slows the moment you stop personally selling
• Sign five: your team can execute, but can't own outcomes or make decisions
• Sign six: you understand how everything works, but the company doesn't
• Sign seven: a buyer removing you would break the business
• Why most people don't do the foundational work until a health scare or life event forces their hand

Time Chapters
00:03 Welcome and the seven signs framework
01:31 Revenue vs. building a real asset
04:06 Sign one: you still approve everything
05:05 Sign two: clients buy access to you
07:58 Sign three: you can't disappear for four weeks
08:39 Sign four: revenue slows when you stop selling
09:54 Sign five: your team executes but can't own outcomes
10:49 Sign six: you know how everything works, but the company doesn't
11:58 Sign seven: a buyer removing you would break the business
14:44 What these signs actually mean, and why most people wait until it hurts

Most leaders think restraint is a weakness. Adrienne thinks it might be the most underused skill in the room. In this episode, Emily flips the format and interviews Adrienne

They dig into what actually happens when leaders can't let go, why diversity of thought keeps getting confused with diversity of identity, and what high care, high standards looks like on the days you don't want to lead at all.

What they cover:

• The leadership myth Adrienne won't call a myth: leaders jumping in to save, answer, and be seen as helpful, and what it stunts on the team
• Why "people can be right without having the same answer as you" is harder to practice than it sounds
• The Target Halloween costume and the Good Good Callaway golf ad, and what both reveal about who gets left out of the room
• A nine year old email complaint about an all white, women presenting team, and why it still applies today
• Adrienne's litmus test for a homogenous mastermind photo: did you notice before you posted it, or only after
• The S-Curve framework from Whitney Johnson, and why a reinvention period puts even experienced leaders back at the bottom of it
• Why Adrienne says she can't hold a high standard until she's done the re-evaluation first
• Restraint as a leadership skill, and why most leaders have none of it
• The rapid fire close: Adrienne's real answer on the leadership trait she's still working on, and a very honest tangent about arguing with Claude
  

Time Chapters
00:01 Welcome, banter, and a blow dryer that almost caught fire
03:39 Emily flips the format and starts asking the questions (estimate,
04:20 What leadership myth is actually hurting people
08:19 The Target costume and the Good Good Callaway ad
14:36 The nine year old email about an all white team
18:19 High care, high standards on the bad days
19:01 The S-Curve, and why reinvention resets everyone
25:17 Why Adrienne won't hold a high standard before the re-evaluation
28:09 Rapid fire: the trait she's still working on
30:43 The Claude tangent: AI, connection, and arguing with a chatbot

Most people who build a multiple seven-figure company spend the rest of their career defending it. Dr. Darnyelle dismantled hers on purpose.
Ten full-time employees gone.
A $42,000 mastermind sunset.
A gap year with no launch and no revenue push.

Dr. Darnyelle is an award-winning CEO, speaker, consultant and strategist whose work has been featured in Inc., Forbes, Essence, SUCCESS, Black Enterprise and O magazines. She is a best-selling author with 8 books to her credit, and the founder of Incredible One Enterprises. She has helped 85 CEOs create their first or next seven figures.

In this episode she walks Adrienne through what it actually took to unwind the company she spent 20 years building, and why turning 50 made the decision non-negotiable.

What they cover:

• The math nobody talks about: a $100,000 monthly overhead meant she had to produce $1.2 million a year just to turn the lights on
• Why she made the call in Bali on her 50th birthday and what the first 30 days back looked like
• How she released her team and still honored every client contract through June 30
• The oxygen mask problem: choosing yourself over the households depending on your payroll
• Why she believes most people hitting a ceiling do not have a strategy problem, they have a capacity problem
• The year she hit seven figures, the work did not change. She did.
• What the Inc. 5000 actually costs, and why she stopped paying for it
• Why your body will make you spend a $250,000 month back down to what feels safe
• The eight weeks home, six weeks away schedule and the three-day workweek she plans to keep
• Rewriting her estate plan so the money funds her life now instead of a rainy day she will not be here for
  

Connect with Dr Darnyelle:
incredibleoneenterprises.com/sanctuary
movetomillionsquiz.com
The Move to Millions Podcast
Grab her book, Move to Millions

00:00 Meet Dr. Darnyelle

01:00 Who she be

03:35 The business pastor

06:20 On downloads and channeled work

08:05 The version of entrepreneurship we do not talk about

08:40 Turning 50 and starting the recalibration

11:00 Retiring the seven-figure company

12:20 The decision she made in Bali

12:55 Secure your own mask first

16:20 How she unwound it without breaking her word

18:25 Sanctuary Core and the new Sanctuary Scale

21:05 Why you run a beta before you go to market

23:35 Strategy does not transform businesses

25:00 The invisible work nobody wants to do

25:50 The nothing to prove season

26:40 What the Inc. 5000 really costs

29:40 Camera crews and content theater

33:15 Rewriting the estate plan to live now

35:45 The metric she cares less about

37:45 Seven-figure businesses that are really zero-figure businesses

41:00 Why your body rejects money

43:15 The metric she cares about now

45:00 Best use of money and best use of time

48:35 Obedience over the easy $100,000

53:25 What is the worst that could happen

56:50 Where to find Dr. Darnyelle

Adrienne has spent about 12 years working in operations with founders. The systems, the team, getting things out of the owner's head and onto paper. And she still keeps running into the same thing: every piece is in place, and the founder is still the bottleneck.

The hire is made. The process is written. And they're still doing it all themselves.

Adrienne is joined by Makhosi Nejeser, who advises founders who've built the business, hit the numbers, and noticed that winning doesn't feel the way it used to. Drawing on eight years advising founders and full initiation into a Southern African tradition rooted in advising leaders through transitions of power, she founded The House of Sovereign Legacy, where she hosts monthly House Briefings and the Architects of Sovereignty podcast.

What they cover:

• Why the bottleneck is almost always you, and why that is the hardest bottleneck to solve
• Why "no one else can do this as well as me" is never true, and the two reasons it falls apart
• The WWJD problem: teams running every decision through what the founder would do instead of what the business would do
• 91% of women-owned businesses have zero employees, and the survival programming underneath that number
• Doing the work versus designing the work, and why designing feels terrible because the gratification is delayed by years
• Restraint as the most undervalued leadership skill, and the question that replaces micromanaging: is it wrong, or is it just different?
• Le Pause, borrowed from French parenting, and what happens when you stop rushing in
• 76% of founders regret selling, and the three-year identity crisis behind that number
• The exit math: a business dependent on you sells for two to three times, one that runs without you sells for four to five
  

Take the diagnostic Adrienne mentions at the end: level11leaders.com/exit

Find Makhosi at theroyalshaman.com, and she's @theroyalshaman on Instagram.

⏱️ Time Chapters
00:01 two podcasts, one conversation
05:19 the ceiling systems can't break
10:08 no one else can do this as well as me
14:44 when nothing changes, look inward
25:38 digging the hole vs the rubik's cube
30:56 restraint is the skill nobody teaches
35:04 most businesses get built from survival
44:44 le pause
49:29 ask, don't answer
55:44 delegation starts with five pound weights
01:00:23 the trigger point doc
01:04:53 the five whys for identity
01:09:23 76% of founders regret the sale
01:14:18 you are not invincible
01:19:56 the founder's reckoning

Most founders say they hate the chaos.
Most founders also create it.

When everything gets labeled urgent, the label stops meaning anything.

Adrienne and Emily get into why urgency becomes a founder's default setting and what it's actually protecting. Often it's a need to be needed.

What they cover:

• Why "when everything is urgent, nothing is urgent" is a culture problem, not a workflow problem
• The guiding principle Adrienne built her company on: we're not creating oxygen
• The paper mill job where everyone acted like the building would collapse without them
• The 11pm website outage Adrienne told her team to go to sleep on
• Why people who demand urgency also tend to have zero tolerance for mistakes
• The 10/80/10 trap: when the founder can't do the first 10%, nobody can do the other 80%
• Emily on demoralizing the exact kind of person you said you wanted to hire
• The stat behind why so many women-owned businesses never build a team
• How entrepreneurs slowly morph into the bad leaders they left
• Where to actually start: name your guiding principles before someone else's urgency sets your pace
  

Listen at level11leaders.com/podcast
Connect with us on Instagram

⏱️ Time Chapters
00:01 Welcome, matching hair, and summer admin
07:26 Founders use urgency to stay important
11:24 The night the website went down
15:35 Tight deadlines vs. manufactured urgency
19:46 You're demoralizing the person you hired
24:00 How entrepreneurs become what they left
28:09 Define the vibe before someone else does