You can pack the bags, take the flight, check into the hotel, and still end up sitting on the beach answering Slack. Most founders call that freedom because it happened somewhere new... but working in a new location does not equal freedom.

Adrienne spent this Tuesday on the golf course and spent this week getting a biopsy she almost put off. Both of those are the same story.

This solo episode kicks off a run of episodes built around one question: can your business actually run without you?

What she covers:

• Why "I can work from anywhere in the world" is a sentence worth hearing yourself say out loud
• Two out of office moments from Adrienne's week: a Tuesday tee time, and the doctor's appointment she came close to pushing off again
• Location freedom is about where your body is. Mental freedom is about whether the business is still running in the back of your head while you're there
• The client who asked whether he was still allowed to think about his business during his four week unplugged, and the answer he got
• Why the big ideas only show up once the day to day noise clears out
• The client who worked from the labor and delivery room and told herself it counted as freedom
• Why remote work got optimized so well that your body can be anywhere while you stay completely trapped
• Where to start: a free diagnostic that scores owner dependency across six categories
  

Take the free out of office diagnostic: level11leaders.com/exit

⏱️ Time Chapters
00:00 The beach, the Slack, the lie
04:05 The appointment she almost skipped
08:58 Location freedom is not freedom
13:10 You optimized for the wrong one
17:15 Find out where your business needs you

Emily showed up with a list of questions and Adrienne had no idea what was coming. What followed was one of the more honest conversations they've had on the show.

In this episode, Emily puts Adrienne in the hot seat for a rapid fire Q&A. No prep, no filter, and some answers that surprised even the person giving them.

What they cover:

• The best advice Adrienne ever got and then ignored for years, and why she's finally living it this year
• How this has genuinely been one of the harder financial years in the business, and what the monthly conversations between Adrienne and Emily actually sound like
• The leadership mistake Adrienne had never said out loud until now: stepping back so far it became abdication, and what it cost the team
• What Emily told Adrienne at the end of last year that changed how they work together
• A belief about hard work and success that Adrienne has completely reversed after years of watching other people build differently
• What Adrienne's team does better than her (almost everything, and she says so)
• Why rest still feels wrong when you're in a build phase, and the reframe that matters anyway
• The difference between needing a vacation and needing spaciousness, and why no-call weeks might be more valuable than either
  

Submit your own Dear Bossy question: sortabossypodcast.com

⏱️ Time Chapters
00:01 Sunkissed, frizzy hair, and heat waves in Canada
06:27 Emily has rapid fire questions and Adrienne knows nothing
08:16 Best advice ever gotten and completely ignored
10:39 The hardest conversations this year
12:32 Every month ends in a hype session
14:11 What the team does better than Adrienne
16:03 The leadership mistake Adrienne never admitted
18:55 What Emily told Adrienne that almost made her quit
22:08 A belief about hard work she's completely changed her mind on
24:03 The hat maker and Alex Hormozi in Kentucky
26:21 What does rest actually look like for you
28:50 You don't need the big picture ideas until you have the space for them
30:32 You don't have to earn rest

Middle management is the loneliest role in any organization.

In this Dear Bossy episode, Adrienne and Emily respond to a listener who manages a tight-knit team of three, does all the invisible work of protecting them from above, advocates for their growth, and still ends up feeling like she's not really part of the group.

It's a more common feeling than most managers will admit.

What they cover:

• Why your team bonding without you is actually a sign you're doing something right, even when it doesn't feel that way
• The invisible work of middle management: shielding your team from pressure, advocating behind the scenes, handling problems before they land on anyone else's desk
• Why the middle is often the loneliest layer of any organization, and why that is by design, not failure
• The difference between needing community and needing your team to provide it
• Emily's honest take on being the only person in the middle and what she did to navigate it
• How to ask your organization for development, mentorship, or coaching and why your leadership is already spending money on exactly that
• Practical ways to close the connection gap: therapy, peer networks, lunch and learns, industry events, and what happens when you just introduce yourself to the person next to you
• A teaser for something Adrienne and Emily are building specifically for operators and middle managers who need their own community

Submit your own Dear Bossy question: sortabossypodcast.com

⏱️ Time Chapters
00:01 Periscope, Clubhouse, and the graveyard of dead platforms
04:15 Summer House, audiobooks, and brains with nothing left in them

09:55 The listener question: am I being unreasonable for feeling left out of my own team?

13:05 Your team bonding without you is actually the dream

14:01 The invisible work nobody sees and nobody thanks you for

15:07 Emily's take: the middle is the loneliest layer

17:54 Middle management is the most burned out role in any org

20:13 Ask for the development your leadership is already investing in themselves

22:07 Lunch and learns, industry events, and a little like dating

24:07 Stay tuned, something's coming for operators and middle managers

Most personality frameworks collect dust after the first quiz.
Lisa Cumes & Mario Teran use the Enneagram as an operating system for their business, their team, and every hard conversation they have to have.

Mario and Lisa are a married couple who work together and coach other couples in business on how to build real alignment, not just a functioning working relationship.

What they've figured out applies whether you're running a company with your spouse or just trying to lead people better.

What they cover:

• Why alignment between partners, not hustle, is what actually makes a business run well
• The ARC framework as the foundation of any high-functioning partnership, personal or professional
• How to use the Enneagram as a shared language with a business partner, your team, and even clients you've never asked to take a personality test
• Why understanding yourself has to come before you can effectively lead, communicate with, or support anyone else
• What happens when couples in business put the revenue goals first and the relationship second, and why that order always backfires
• The walk and talk habit: a structured daily check-in that keeps small frustrations from becoming big blowups, and how to make it work with a packed schedule
• How to parent, lead a team, and manage client relationships using the same framework without ever asking someone their number
• The 30-day walk and talk challenge and where to find it
  

Connect with Mario and Lisa and download their FREE 30 Questions for your next Walk & Talk PDF Guide: marioandlisa.com

You can also grab their free enneagram guide here.

Or connect with them on Instagram!

⏱️ Time Chapters
00:00 Introducing Mario and Lisa
04:15 What a real power couple actually looks like
05:54 Radical responsibility: you are not responsible for each other's happiness
07:01 Awareness and the Enneagram: how Mario found himself in a framework
11:44 Adrienne's Enneagram origin story and Ryan Levesque's team Slack
14:03 Understanding yourself first, then your partner
17:11 When two whole people leverage their differences together
21:27 You don't have to do it twice to get it right
25:32 Stop waiting for the business to be better before investing in the relationship
27:28 The walk and talk habit and why it works
31:36 If you can't walk 30 minutes with your partner, you have a bigger problem
36:09 Borrow 30 minutes from social media
37:30 Using the Enneagram with your kids
41:40 Where to find Mario and Lisa and the 30-day challenge

A Reddit submission that must be discussed!

The writer's manager sent them a passive-aggressive link to "Let Me GPT That For You" instead of answering a simple question on a call they were already on.

The employee left and didn't come back the next day. Adrienne and Emily have opinions.

In this Dear Bossy episode, Adrienne and Emily dig into a viral-feeling workplace situation that splits people into two camps fast.

Was the employee out of line for asking something they could have Googled?
Or is the manager the bigger problem?

Turns out the answer is kinda both... but not equally.

What they cover:

• The "Let Me GPT That For You" link, what it actually does, and why sending it is an act of deliberate humiliation not a productivity tip
• Why Adrienne says you're both the asshole, but the manager is the bigger one by a lot
• The difference between communicating an expectation and publicly embarrassing someone into learning it
• What the manager should have said instead, and how long it would have actually taken
• Why leaving people feeling like they have to walk on eggshells is one of the worst things a leader can do to a team
• The outsourcing critical thinking problem: when it's fair to expect employees to Google things and when it isn't
• Emily's case for bringing back public shaming (and Adrienne's Game of Thrones reference to back it up)
• How to vent first, then distill it into an actual boundary or expectation

Submit your own Dear Bossy question: sortabossypodcast.com

⏱️ Time Chapters
00:01 Happy Tuesday and the female tax of getting camera-ready
04:15 Today's Dear Bossy situation
08:51 You're both the asshole, but not equally
12:00 The 10 leadership failures vs. the one employee growth area
14:08 Emily cannot fathom treating another human this way 16:21 Bring back shame, bring back Google
20:31 What good leadership actually looks like here
22:07 Vent first, then distill it into a real expectation

Adrienne just got back from New York Tech Week, where she spoke to a room of female founders about something most of them had never thought about before. She's not done talking about it.

In this solo episode, Adrienne breaks down the four categories of exits, why 24 different versions of an exit exist, and why most female founders are only picturing one of them.

She makes the case that building without an exit plan is not ambition. It's a liability in the making.

What she covers:

• What Adrienne spoke about at New York Tech Week and why the conversation is one we are not having nearly early enough
• The four exit categories: scale, sell, step away, and secession planning, and what falls under each one
• Why an exit does not have to mean a sale, and why thinking it does is keeping founders stuck
• How long each exit path actually takes to prepare for, from 18 months to a decade
• The insurance plan framework: if you step out tomorrow, does everything disappear with you?
• The dentist and the dog food website, and what happens when a seven-figure business is worth nothing to the person left behind
• Why the operational work is the same no matter which exit you choose
• The free Out of Office training and what Adrienne is covering live

Free training: level11leaders.com/OOO

⏱️ Time Chapters
00:01 Solo episode and New York City recap
04:42 What exit actually means, and the 24 versions most founders don't know about
09:23 How long each path takes and why you need to start now
13:59 The best time to plant a tree was 20 years ago
16:16 The dentist, the dog food website, and the wife who couldn't inherit any of it
18:39 Why we are not having this conversation enough and what Adrienne wants to do about it

Most leaders believe they have built an open, safe, equitable team. The team usually disagrees. The gap between those two things is where this whole conversation lives.

Trudi Lebron has spent 20 years as an equity practitioner, starting in education and youth development before making a deliberate move in 2017 to bring this work into the coaching and online business world.

Adrienne worked with her in back in 2020, and they have been crossing paths ever since. This time they sit down to talk about what equity actually means inside a company, and why so much of it comes down to power and how you use it.

What they cover:

• Why "we're not creating oxygen" became a guiding principle, and how it changes the energy a whole team runs on

• Why equity is so much bigger than race, and how it shows up in onboarding, work hours, and the structure people actually need to succeed

• The real reason most leaders stay quiet: not kindness, just fear of getting it wrong

• Why letting things slide is an abdication of responsibility, not good-boss behavior

• The difference between wanting to lead and wanting to be in charge

• Why power is neutral, and what owning it actually unlocks instead of avoiding it

• The restraint problem: what you steal from your team every time you jump in

• How middle managers become the dam, and what happens to the whole team when it breaks

• The psychological safety test: if no one pushes back, assume they do not feel safe

Trudi Lebron, MS, is a highly skilled executive coach and facilitator with over 20 years of experience helping public and private institutions, entrepreneurs, solopreneurs, and founders build equitable businesses, workplaces, and learning environments. She is the founder of The Institute for Equity-Centered Coaching, the author of The Antiracist Business Book (Row House Publishing, 2022), and a PhD candidate in Social Psychology.

Find Trudi at trudilebron.com, on her weekly email Working Hypothesis, and on her podcast, where Adrienne appears in the episode "I Had To Shed This Skin."

Time Chapters

00:00 How Adrienne and Trudi met

02:00 Why Trudi chose equity work

03:50 Equity is bigger than race

04:50 Equity meets capitalism

07:40 Never becoming the boss you hated

09:20 We're not creating oxygen

11:05 You can't teach people how to be free

12:45 Onboarding for how someone actually works

15:05 Equity serves the business too

17:25 Doing nothing for fear of getting it wrong

20:30 The expectation you never actually set

22:45 The power dynamic you don't want to admit

24:50 Power is neutral

27:00 Authority is given, not taken

29:00 Restraint as a leadership skill

30:40 Why you really jump in

32:40 Middle managers as the dam

40:05 Speaking up needs safety

41:50 How to know it's not safe

43:25 Where to find Trudi

44:50 The AI conversation they saved for next time

Women own 40% of all businesses in the United States and represent just over 1% of business exits.

Adrienne has thoughts about that, and she's not holding back.

In this solo episode, Adrienne makes the case that if your business can't run without you, it's not actually a business. It's a job with lipstick.

She walks through why female founders in particular get stuck in owner dependency, what it costs them, and what it actually looks like to start building a real exit.

What she covers:

• The difference between a business that's an asset and one that's a liability hiding in plain sight
• Why women represent 40% of business owners but just 1% of exits, and what that gap is actually telling us
• The identity trap: why stepping back feels like a betrayal, and why that feeling is keeping you stuck
• At least six different definitions of "exit" that have nothing to do with selling your business
• How removing owner dependency can two to three times the value of your business
• The dog food website story: a retired dentist, millions of monthly views, and a wife who couldn't inherit any of it
• Small business owners take an average of five days off per year, and 67% check in with work every day they're supposedly on vacation
• The 90-day test: if you had to step away from your business tomorrow, would it survive?
• The free Out of Office training and what Adrienne is covering there
  

Free training: level11leaders.com/OOO

⏱️ Time Chapters
00:00 Solo episode and kindergarten graduation chaos
04:10 Is your business an asset or a job with lipstick
08:30 The dog food website story
13:00 Women own 40% of businesses but represent 1% of exits
17:30 Why women exit unplanned and for less money
22:00 The identity trap and why stepping away feels like betrayal
27:30 Six versions of what an exit could actually look like
33:00 Owner dependency is costing you two to three times your valuation
37:00 The 90-day test
40:00 Out of Office free training and close