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Sorta Bossy

Sorta Bossy

Written by: 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

2026 Sorta Bossy Podcast
Careers Economics Personal Success
Episodes
  • Your Operator Deserves Better Than You
    Oct 13 2026

    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

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    29 mins
  • Who Decides What's Professional Anyway?
    Oct 6 2026

    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



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    28 mins
  • Selling the Thing You Swore You Never Would w/ Steve Guberman
    Sep 29 2026

    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

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    46 mins
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