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Can We Not? Business Is Hard Enough.

Can We Not? Business Is Hard Enough.

Written by: Samantha C. Prestidge
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Can We Not? Business Is Hard Enough. A Podcasts for Working Founders (previously Strategies, Solutions, and Sanity). Running a business is hard enough. The advice you've been given shouldn't make it harder. Can We Not? is the podcast for founder-led businesses that are done overcomplicating the work. No eight-figure frameworks. No systems that require a full-time project manager to maintain. Just the real, behind-the-scenes decisions that shape how a business actually runs. I'm Sam Prestidge, founder of Auxo Business Services, and I work with visionary doers, the people who want to stay in the work but want that effort to actually build something instead of just keeping up. We talk about delegation, operations, team support, and the unsexy stuff that makes the difference between a business that grows and one that just stays busy. If you're running a small team, or no team at all, and you're tired of chasing strategies that sound smart but don't fit how you work, you're in the right place. Let's uncomplicate this thing.2025 Economics Leadership Management Management & Leadership
Episodes
  • 40. Can We Not People-Please Our Way Through a Growing Business? | Conference Growth with Megan Shapiro
    Apr 7 2026


    Growing community, conference, or business without losing your original vision — and your sanity — can be a picasso painting that easily gets distorted.


    Host Samantha C. Prestidge chats with Megan Shapiro, construction attorney and founder of the Converge Construction Summit, about strategic community growth, what sustainable business building actually looks like, and how to stop people-pleasing your way into something you didn't mean to create.


    Megan grew Converge from 13 people in Savannah to 55 in Chicago — and her most important work wasn't any of that growth. It was the months she spent figuring out why her best-reviewed event left her completely drained.


    In this episode:


    • How to grow a community or event without losing what made it work
    • Why strategic growth beats fast growth — and how to tell the difference
    • What people-pleasing in business actually costs you, even when things look successful
    • How to hear what your audience wants and identify what they actually need
    • Why sustainable business growth requires knowing your vision before you scale it
    • What months of business coaching, therapy, and a mastermind finally unlocked that a successful event couldn't

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    50 mins
  • 39. Can We Not Be the Reason Our Assistant Fails? Three Crucial Calls for Clarity
    Mar 31 2026

    You’ve hired an assistant before. It didn’t stick. And if you’re honest, you’re not totally sure why.


    Host Samantha C. Prestidge of Auxo Business Services breaks down the three areas of clarity founders need to have in place before they bring on an assistant — and why skipping them is almost always what tanks the working relationship.


    This solo episode gets into why even strong assistants fail when founders aren’t ready, the difference between delegating tasks and delegating outcomes, and the Map It → Keep It → Delegate It framework Sam uses with her own clients.



    Topic Bullets

    • Why building SOPs before you hire is the wrong starting point — and what to do instead

    • The “cart before the horse” pattern that ends most assistant relationships early

    • What “how you want to play in your business” actually means — and why founders who skip it become micromanagers

    • How to write a value statement that ties your assistant’s work to real business outcomes, not just your to-do list

    • When “I can’t grow because I’m at capacity” is actually a clarity problem, not a bandwidth one

    • The Map It, Keep It, Delegate It framework
    • Book a delegation strategy session: auxosvs.com/strategy




    Timestamps

    • 00:00 Hidden Expectations
      00:21 Podcast Mission
      01:49 Delegation Failures
      03:31 Skip The SOP Trap
      04:52 Three Clarity Areas
      05:08 Map What Youre Building
      07:18 Keep Your Founder Role
      09:13 Delegate Outcomes Not Tasks
      11:49 Map Keep Delegate Framework
      12:27 Book A Strategy Session


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    13 mins
  • 38. Can We Not Keep Marketing to Everyone and Serving No One? | Finding the Right Operations Partner with Ashley Connell
    Mar 24 2026

    Hiring operations help for your small business is harder than it should be — and most founders are looking at the wrong things when they do it.

    Ashley Connell, CEO of Prowess Project, has spent seven years matching small business owners with operations partners. She's learned that the skills on a resume tell you almost nothing about whether someone can actually run your business alongside you.

    In this episode:

    • Why hiring for tech stack and job titles fails service-based business owners
    • How to find the right operations partner for your small business
    • The four-step framework Ashley's ops partners use from day one
    • Why delegating outcomes doesn't work — and what to communicate instead
    • How to know if you need an operations partner or if your processes need fixing first
    • What a two-week time study reveals that no hiring process can

    00:00 The Need for Management

    00:41 Welcome to Can We Not

    01:41 Meet Ashley Connell

    02:22 What is an Ops Partner

    04:46 Meeting Leah

    05:42 Flexible and Fulfilling Careers

    06:59 The 97 Percent Statistic

    07:38 The Matching Algorithm

    10:47 Proven Results and Success Stories

    13:14 Overcomplicating the Journey

    15:38 Niching Down to Accounting Firms

    17:22 Testing and Experimentation

    19:22 Naming the Ops Partner

    21:20 Experimentation With Intent

    22:35 Accountability and Feedback

    26:06 Four Step Delivery Method

    29:03 Setting Clear Expectations

    32:24 Behaviors Over Outcomes

    34:28 Practical AI Integration

    36:29 Time Study to Simplify

    38:40 Closing Thoughts

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    39 mins
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