Can We Not? Business Is Hard Enough.

Can We Not? Business Is Hard Enough.

By Samantha C. PrestidgeBusinessEntrepreneurshipManagement
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Can We Not? Business Is Hard Enough. episodes

  • Can We Not Make It Scalable Before We Make It Sellable?


    Garrett Jestice has a framework for service businesses that is painfully simple: Discovery → Focus → Expansion.


    The problem is that a lot of founders skip the first two and head straight for expansion.


    New offer. New funnel. New hire. New marketing channel. New tech stack. More content. More networking.


    And sometimes the real issue is that the business still has not proven what people actually want to buy.


    In this episode, Garrett and I talk about how to find offer-market fit, why passive marketing takes longer than most founders want to admit, how to know when you are actually ready to scale, and why throwing more money at agencies, salespeople, or marketing rarely fixes a clarity problem.


    We also get into the less polished side of growth: working too much, hitting the fractional ceiling, getting distracted by vanity metrics, and building a business that gives you freedom of time instead of just more revenue.


    Garrett also shares a client story about spending more than $100K on marketing without getting results, and what actually had to change before growth started working.


    In this episode, we cover:


    • Garrett’s Discovery → Focus → Expansion framework
    • what offer-market fit actually means for a service business
    • why founders jump into scaling too early
    • active vs. passive marketing
    • why networking does not automatically equal business development
    • intro offers and when free work can actually make sense
    • the fractional ceiling and the limits of selling your time
    • why viral content and revenue are not the same thing
    • what founders should own before blaming a salesperson, agency, VA, or contractor
    • building a business around proof instead of assumptions


    One line worth remembering:
    Your business does not always need another offer. Sometimes it needs you to pay attention to what people are already trying to buy.

    50 min
  • Can We Not Call “Feast or Famine” a Marketing Problem?


    Joe Daniels thinks a lot of solo business owners are trying to solve the wrong problem.


    When business slows down, the instinct is usually to blame marketing.


    But if you had a "feast" before the famine, your marketing clearly worked at some point. The bigger question is why it stopped.


    In this episode of Can We Not?, Joe and Sam dig into the operational side of running a solo service business, including the parts founders often ignore because they'd rather focus on the work they're actually good at.


    Joe shares how his experience as the first employee at a marketing agency showed him the feast-and-famine problem firsthand, why he eventually realized he'd built a business he enjoyed talking about more than actually running, and the quarterly review that led him to change direction.


    They also get into:


    • Why founders need both a visionary hat and an operator hat
    • Joe's Direction, Demand, and Delivery framework
    • Why feast and famine can be an operations problem rather than a marketing problem
    • How Joe used the Odyssey Plan to rethink his own business
    • Why "I don't have time" is often really "I didn't make time"
    • Making uncomfortable business-development work small enough to actually do
    • Designing an offer around the business and life you want
    • Joe's Do, Delegate, Die approach to simplifying work
    • Why telling prospects they're not a good fit sometimes makes them want to hire you even more


    If you're good at your actual work but occasionally wonder when exactly you became responsible for running an entire company around it, this conversation is for you.

    47 min
  • Can We Not Pretend You Need Perfect SOPs Before You Delegate? Behind the scenes with Sam & Sonia


    What happens when your five-month onboarding plan suddenly becomes three months, your processes are outdated, you decide to launch an entirely new internal app, and then you leave the country for 10 days?


    Apparently, you onboard an operations manager.


    In this behind-the-scenes episode, Sam is joined by Auxo Operations Manager Sonia Narvaez to break down what actually happened during Sonia’s onboarding. And no, it did not involve handing her a beautiful binder of perfectly documented SOPs.


    They talk about the original plan, why it blew up, what they did instead, and how Sonia went from helping with a project to running point on the business while Sam was mostly offline.


    More importantly, they dig into why founders often focus on the wrong things when preparing to delegate. Documentation can help, but it cannot replace clarity, communication, trust, and giving someone enough context to understand how the business actually works.


    In this episode:


    • Why Sam originally planned five months to onboard an Operations Manager
    • What happened when that plan suddenly got cut almost in half
    • Why outdated or nonexistent SOPs didn't derail the onboarding
    • The communication cadence Sam and Sonia used during the first few months
    • Why overcommunicating with a new team member is usually better than trying not to “bother” them
    • How they handled trust, access, permissions, and decision-making
    • The pre-vacation “everything in my brain” roll-up that helped Sonia take over
    • What Sonia ended up handling while Sam was away for 10 days
    • Why knowing the desired outcome matters more than prescribing exactly how someone gets there
    • How healthy disagreement helped them build a stronger working relationship
    • The difference between hiring someone to complete tasks and bringing someone into the business as a real team member


    If you've been telling yourself you'll hire an assistant, VA, or operations person after you get all your processes cleaned up, this episode may ruin that excuse.

    44 min
  • Can We Not List Twenty Services On Our Website? | Doing Two Things Really Well with Emily Court

    If your website lists ten services and clients still can't tell you what you actually do, that's not a marketing problem. That's a menu problem.


    Host Samantha C. Prestidge chats with Emily Court, a website copywriter turned designer and LinkedIn strategist who helps founders and solopreneurs get their websites and LinkedIn presence to actually reflect the level they're working at.

    They get into why cutting from twelve services down to two made Emily more credible, not less, what happened in the two weeks after a single LinkedIn post from a 100K-follower creator sent her more leads than she could handle, and the exact discovery-call question that makes her turn a client down.

    • Why listing twelve services on your website convinces nobody you're an expert in any of them

    • What actually happened in the two weeks after one LinkedIn post went semi-viral: 40+ leads, $5,500 in confirmed business

    • The "testing energy" red flag on a discovery call that makes Emily walk away from a client before the work even starts

    • Why "buy one small thing from me first" out-converts a hard sell every time

    • How Emily built referral relationships without ever calling it networking

    • The pivot from full-time writer to designer, and the project that nearly broke her before it made her business

    41 min
  • Can We Not Pretend Perfectionism Is Helping? | Goal Setting and Knowing Your Limits with Andrea Lowe

    You're setting goals you're scared to miss and grinding through tasks you're bad at because asking for help still feels like failure. Sound familiar?


    Host Samantha C. Prestidge chats with Dr. Andrea Lowe, nonprofit consultant and founder of Social Impact Studio Consulting, who helps organizations expand their impact through strategic planning, program development, and community-centered leadership.


    Andrea went from 15 years in government and public health to running her own consulting firm — and hit the exact wall that most solo founders hit: trying to do everything herself, including the stuff she was genuinely terrible at. What changed wasn't a system. It was admitting she needed one.


    In this episode:

    • Why the A+ student mindset actively works against you when you're running a business

    • The difference between a strategic plan and an implementation plan — and why having one without the other is why nothing gets done

    • How to set goals that are ambitious without becoming the standard you quietly beat yourself up for missing

    • What collaboration over competition actually looks like in a saturated consulting market

    • The moment Andrea realized doing it all herself wasn't discipline — it was a problem

    42 min
  • Can We Not Buy Another Coaching Program? | The 3 Answers You Need Before Your Next Hire, Software, or Program


    Founders wasting money on the wrong coach, the wrong software, or the wrong hire almost always skipped one thing first: three basic questions about their own business. 


    Samantha C. Prestidge is back after a few months off content, sharing the exact three questions she asks clients before any hire, subscription, or program.


    She breaks down why more complexity usually feels more sophisticated but isn't — and why that instinct quietly drains profit and momentum.

    • Why hiring a coach doesn't fix a business that hasn't answered its own basic questions
    • The cooking-competition note that applies directly to your business: "learn to edit yourself"
    • The three questions to ask before any hire, software signup, or coaching program
    • How wrong services and wrong clients both trace back to skipped foundational clarity
    • Why a vision statement isn't the same thing as knowing what you're building toward


    00:00 Podcast Returns

    00:04 Move Abroad Update

    01:17 Why Business Gets Hard

    01:58 Meet Sam And Auxo

    02:58 Simplicity Wins

    04:15 Restraint Like Chefs

    05:11 Costly Overcomplication

    08:07 Three Clarity Questions

    08:24 Define Your Horizon

    10:16 Choose What To Sell

    11:34 Design Delivery Style

    13:32 Wrap Up And Next

    15 min
  • 40. Can We Not People-Please Our Way Through a Growing Business? | Conference Growth with Megan Shapiro


    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

    51 min
  • 39. Can We Not Be the Reason Our Assistant Fails? Three Crucial Calls for Clarity

    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


    14 min
  • 38. Can We Not Keep Marketing to Everyone and Serving No One? | Finding the Right Operations Partner with Ashley Connell

    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

    39 min
  • 37. Can We Not Sell Like We're Trying to Win an Argument?


    Most sales training teaches you to push harder when a prospect hesitates. Aleasha Bahr teaches you to get curious instead — and the results are hard to argue with.


    Host Samantha C. Prestidge chats with Aleasha Bahr, author of Black Sheep Sales and founder of a sales coaching practice that helps service business owners build strategies designed around how they actually think and communicate — not a pushy script that never fit them in the first place.



    They dig into what it looks like to simplify your message down to outcomes people actually want (hint: it's not your list of deliverables), why defining your anti-audience is as important as defining your ICP, and how knowing when to walk away from a sale is the thing that actually brings clients chasing you.


    LINKS

    • Aleasha Bahr on LinkedIn 
    • Black Sheep Sales book
    • Aleasha's website
    • Catch more episodes: canwenotpodcast.com
    • Apply to be a guest
    • Have Sam as a guest on your podcast: [email protected]


    40 min

About Can We Not? Business Is Hard Enough.

From the publisher's feed

Can We Not? Business Is Hard Enough. A Podcasts for Working Founders (previously Strategies, Solutions, and Sanity).