Sorta Bossy

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 ...

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 podca...

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...

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 le...

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. Sh...

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 th...

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 princip...

A business that is working is usually boring. Same offer, same model, same delivery, quietly making money. Which is exactly when founders start looking for a reason to blow it up.

Adrienne calls this an epidemic in the small business space. This episode picks up two threads from earlier conversations, the Be Bored and Rich episode and Adrienne's interview with Denise Duffield-Thomas, and goes deeper on why boredom is so expensiv...

Surprise! Most teams don't go over capacity on purpose. It happens slowly, and then one day that's just your culture.

Worse, by the time someone says out loud that they can't take on one more thing, they've been carrying it for months.

Adrienne has spent the last few months in conversations with business owners who are all hitting the same wall. In this episode, she walks Emily through what a maxed-out team actually cost...

Denise Duffield-Thomas recorded 32 podcast episodes in three days. Then she booked ballet class instead of finding more work to do. Then she felt guilty about it,

Denise is the money mentor behind Money Bootcamp, a program she has now run for 14 years and taught to over 10,000 students. She wrote Get Rich, Lucky Bitch and Chill and Prosper.

She and Adrienne have known each other a long time, so this conversation goe...

Everyone online is selling the same thing.
More sales, more revenue, hit the next milestone.
It makes a clean ad and an enticing screenshot.

It is also pointing you at the wrong metric entirely.

This solo episode is the actual math on what a business is worth.

What Adrienne covers:

• Why revenue advice is so popular.
• The due diligence tip. If someone's only case study is themselves, buyer beware. Doing it and teaching som...

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 ...

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 li...

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 bondi...

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 ...

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 fas...

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...

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 ...

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 w...