Sorta Bossy

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: Wh...

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...

Most founders think they have two options: Keep grinding 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. H...

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 p...

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...

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 Enterpris...

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...

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...

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 deep...

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 maxe...

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 th...

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. Do...

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 kick...

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...

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: W...

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...

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 i...

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 wi...

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...

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 c...

Most leaders think they're choosing between two options when it comes to feedback: be vague or just redo it yourself. Adrienne and Emily have a third take. In this Dear Bossy episode, Adrienne and Emily tackle a listener question about how to give feedback that actually sticks. They get into the difference between lazy and specific feedback, what it really means to delegate well, and why "make it...

Some decisions don't feel like decisions. They feel more like a slow accumulation of clarity that finally gets too heavy to ignore. Adrienne has been moving toward something for years. This is the episode where she names it out loud. Adrienne and Emily sit down for a get-to-know-the-boss conversation that turns into much more than business. They unpack what it actually looks like to trust your gut...

When you're trying to move a business forward and the people closest to you won't budge, it is one of the hardest leadership situations there is. Especially when those people are a partner, a co-founder, or a family member. A listener asked: how do you implement real organizational change when the people around you are resistant, including someone in your family? Adrienne and Emily have been on bo...

Resentment in business does not usually arrive all at once. It builds. And by the time most people name it, it has already started spreading to the team, the clients, and the work itself. Emily has worked alongside Adrienne for almost 10 years. She has watched the seasons shift. She has always had questions. In this episode, she finally asks them out loud. What they cover: Whether Adrienne has act...

You don't actually need to hire three people. You probably need to stop thinking in extremes first. This week, a listener asked the question, "I need an EA, an ops person, and someone for client delivery -- but I only have the budget for one. Who do I hire first?" The answer is not who. It's what. And it's probably sooner and smaller than you think. Adrienne and Emily break down how to actually ma...