Sorta Bossy

Sorta Bossy Podcast
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85% of leaders never get trained. If you became a manager, team lead, or founder without anyone actually teaching you how to delegate, fire someone, or hold people accountable—this show is for you. We're tearing up the old leadership playbook and figuring out what actually works. Hosted by Adrienne Dorison

  1. 5d ago

    Put the Phone Away and Go Say Hi

    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 areWhat event hosts owe their attendees, and where your own responsibility startsThe one small commitment that makes you look approachable between sessionsTreating rejection like practice, and why most groups will welcome you inEmily’s first event as a team member, and why the pressure to bring something back to work made her raise her hand every timeWhy Emily has no fear hosting a panel but freezes walking up to a groupEasy openers: a compliment, someone’s book, a good question from the last session, the speaker’s talk, the catered foodDeciding before you go what you want out of the tripWhy in-person connection is the golden ticket right nowSubmit 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?

  2. Oct 20

    You Need To Get Out Of Office

    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 newWhy 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 businessWhy the most valuable conversations at any event happen in the in-between momentsThe post-conference whiplash that leaves teams scramblingThe honest downside: it is summer camp foodWhy camp is women-only this time, and how to get founder spots first through the Bunk ListGet 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

  3. Oct 13

    Your Operator Deserves Better Than You

    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 setFounders put money into their own coaching, masterminds, and peer groups, and usually nothing into their number 2The cutoff: why Adrienne wouldn't run the room with fewer than 15 people when 35 were promisedSending the refund email, and the response from operators that changed what happened nextHow the free Operators Only Slack community got 15 applications on day 1The system everyone on the team follows except the founderWhy Adrienne would rather be embarrassed than run an event she couldn't deliver onSend 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

  4. Oct 6

    Who Decides What's Professional Anyway?

    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 reactionThe rule Adrienne uses for interviews, sales pitches, investor meetings, and keynotes: don't let anything distract from your goal in that roomWhere so many professionalism rules come from, and why Emily thinks Gen Z deserves some slackA 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 meetingsWhy a sip of water can help you in an interview, and why Emily would turn down the free coffeeThe 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

  5. Sep 29

    Selling the Thing You Swore You Never Would w/ Steve Guberman

    Most founders think they have two options: Keep grindingShut 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 yearsWhat an acquihire is, and why a burnt out founder often wants to become your employeeWhy hiring a salesperson almost never works under seven figures, and what to buy insteadThe difference between an entrepreneur and an accidental business owner, and how to tell which one you areThe RFP his six person agency never should have won, and the year that followedNine pitch meetings, three offers, and the sale he almost never madeWhy he begs founders not to shut it down, even when the exit is not life changing moneyMerger versus acquisition in plain language, plus how a seller keeps equity for a second biteWhy 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

  6. Sep 22

    Seven Signs You Built a Job, Not a Business

    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 valuableSign one: you still approve everything, even after hiring expensive help to stop doing thatSign two: clients are buying access to you specifically, not a system that delivers without youSign three: you can't disappear for four weeks without still checking your phoneSign four: revenue slows the moment you stop personally sellingSign five: your team can execute, but can't own outcomes or make decisionsSign six: you understand how everything works, but the company doesn'tSign seven: a buyer removing you would break the businessWhy 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

  7. Sep 15

    You Can Be Mad, You Can't Be Mean

    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 teamWhy "people can be right without having the same answer as you" is harder to practice than it soundsThe Target Halloween costume and the Good Good Callaway golf ad, and what both reveal about who gets left out of the roomA nine year old email complaint about an all white, women presenting team, and why it still applies todayAdrienne's litmus test for a homogenous mastermind photo: did you notice before you posted it, or only afterThe S-Curve framework from Whitney Johnson, and why a reinvention period puts even experienced leaders back at the bottom of itWhy Adrienne says she can't hold a high standard until she's done the re-evaluation firstRestraint as a leadership skill, and why most leaders have none of itThe 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

  8. Sep 8

    My 50s Are for Freedom with Dr. Darnyelle

    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 onWhy she made the call in Bali on her 50th birthday and what the first 30 days back looked likeHow she released her team and still honored every client contract through June 30The oxygen mask problem: choosing yourself over the households depending on your payrollWhy she believes most people hitting a ceiling do not have a strategy problem, they have a capacity problemThe year she hit seven figures, the work did not change. She did.What the Inc. 5000 actually costs, and why she stopped paying for itWhy your body will make you spend a $250,000 month back down to what feels safeThe eight weeks home, six weeks away schedule and the three-day workweek she plans to keepRewriting 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

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85% of leaders never get trained. If you became a manager, team lead, or founder without anyone actually teaching you how to delegate, fire someone, or hold people accountable—this show is for you. We're tearing up the old leadership playbook and figuring out what actually works. Hosted by Adrienne Dorison

Information

  • Creator
    Sorta Bossy Podcast
  • Years Active
    2026
  • Episodes
    38
  • Rating
    Explicit
  • Copyright
    © 2026 Sorta Bossy Podcast