Why does growth start to feel heavier the harder you work — even when the revenue is real and the team has grown?

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In this episode of the Delegated Task Podcast, host Jesse Hoss sits down with Chris Buckingham, founder of Solve CXO, to dig into one of the most common and painful stages of business ownership: the messy middle. Chris spent over a decade running an IT company in the Fargo-Moorhead area — learning hard lessons about taxes, trust, delegation, and what it actually takes to build something worth selling. After exiting that company and stepping back into the world of business operations, he now works side-by-side with founders and executives who are strong at their craft but buried in decisions, broken processes, and a business that still runs entirely through them.

Together, Jesse and Chris unpack why being the expert in your business can quietly become the biggest thing holding it back, what it actually means to delegate authority instead of just tasks, and how the owners who get stuck the longest are often the ones working the hardest. Chris shares how he used fractional leadership, scorecards, and intentional systems to unlock his own team — and how he now helps other owner-operators do the same.

This episode also gets into the difference between a lifestyle business and a scalable one, why documenting your processes is the boring work that actually sets you free, and what it looks like to identify the single biggest constraint inside your business and build a plan to remove it.

If you are a Fargo-area business owner who feels like everything still runs through you, this episode was made for you.

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Action Item: Figure Out What You Should Stop Doing

Most business owners do not stall because they are lazy. They stall because they are doing too many things that should not be on their plate at all. This week, try this:

- Write down every task you handled in the last seven days — even the small stuff

- Mark anything that someone else could have done with the right tools, training, or trust

- Pick the one task you hate the most or that drains you the fastest — that is your first delegation target

- Set a 30-day deadline to get it off your plate, whether that means hiring a VA, bringing on a contractor, or handing it to someone already on your team

You do not have to delegate everything at once. Start with one hour a week. Once you get comfortable with one thing off your plate, the next one gets easier. The goal is not to do less — it is to do the right things.

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Connect with Chris Buckingham:

Website: https://solvecxo.com

LinkedIn: https://www.linkedin.com/in/chrisbuckingham

Business Breakthrough Program: https://solvecxo.com

Connect with Jesse:

Website: https://delegatedtask.com

LinkedIn: https://www.linkedin.com/in/jesse-hoss-✅-635b61276/

Email: info@delegatedtask.com

Thank you for listening to the show, your support means so much!

-Jesse Hoss

What does it actually take to go from a rental property to running multiple businesses — and survive the startup phase along the way?

In this episode of the Delegated Task Podcast, host Jesse Hoss sits down with Fargo-based entrepreneur Jacob Henderson to explore the raw, unfiltered reality of building businesses from the ground up. Jacob went from a corner office in Colorado — feeling completely alone despite the mountain views — to becoming a multi-business owner in Fargo, running the Fargo Flooring Store, Dakota Stone and Tile, and a growing portfolio of real estate ventures.

Together, they unpack what it really looks like to start something from scratch, why real estate is such a common entry point for first-time entrepreneurs, and how Jacob turned those early property investments into the foundation for everything else he has built. Jacob shares the honest truth about the stress of taking on investors' money, the danger of not watching where every dollar goes, and why saying "no" to the wrong business is one of the hardest — and most important — things a startup can learn to do.

This episode also digs into the difference between pivoting and flailing, how to detach from the day-to-day and actually lead your business, and why accountability — not blame — is the thing that finally unlocks growth. Jacob's perspective on relationships, community, and the long game will resonate with anyone who has ever wondered if they are doing enough or moving fast enough.

If you are a Fargo-area business owner in the startup phase, or just thinking about taking that first leap, this episode is for you.

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Action Item: Start Tracking Your Time This Week

One of the most eye-opening things you can do as a business owner is figure out where your time is actually going. Most people dramatically underestimate how long things take — and that makes it almost impossible to price correctly, delegate effectively, or figure out what is worth doing at all.

Here is how to get started in under five minutes:

1. Download Clockify — it is free and available on your phone and desktop

2. Create a project for each major area of your business (sales, operations, client work, admin, etc.)

3. Start a timer every time you switch tasks — or log it manually at the end of the day

4. At the end of the week, review your report and ask: was the time I spent on each project actually worth it?

Once you know what your time is worth — even if you just pick a number like $100 an hour as a starting point — you will start making completely different decisions about what to do yourself and what to hand off.

It will not feel natural at first. Do it anyway. The data will surprise you.

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Connect with Jacob Henderson:

1. Fargo Flooring Store: https://www.fargoflooringstore.com

2. Dakota Stone and Tile: https://www.dakotastonetile.com

3. Store Location: 405 Main Avenue, West Fargo (behind Sandy's Donuts)

4. Jacob’s LinkedIn: https://www.linkedin.com/in/jacob-jake-henderson-440b6459/

Connect with Jesse:

1. Website: https://delegatedtask.com

2. LinkedIn: https://www.linkedin.com/in/jesse-hoss-✅-635b61276/

3. Email: info@delegatedtask.com

Thank you for listening to the show, your support means so much!

-Jesse Hoss

Why does video content matter — and what does it actually take to use it effectively as a business owner?

In this episode of the Delegated Task Podcast, host Jesse Hoss sits down with Fargo-based video and photo producer Andrew Stone to explore why video is one of the most powerful tools a business can invest in — and why so many businesses are either misusing it or avoiding it altogether.

Together, they discuss what the creative process really looks like when working with a professional content partner, why handing a camera to a burnt-out team member rarely works, and how to know if your business is actually ready to invest in video marketing. Andrew breaks down the key differences between hiring a professional and trying to handle it in-house — covering everything from expertise and gear to storytelling, editing, and managing expectations.

This episode also explores the delegation mindset, how Andrew structures his week as a solo operator, and why video is only one piece of a larger marketing puzzle. Listeners will walk away with a clearer picture of what strategic video content marketing looks like — and whether they're ready to pursue it.

If you're a Fargo-area business owner wondering whether video is worth the investment, this episode is for you.

Action Item: Turn On 4K Video on Your iPhone

One simple action you can take right after listening to this episode is to upgrade the video quality already in your pocket.

Here's how to do it in under 60 seconds:

1. Open your iPhone Settings
2. Scroll down and tap Camera
3. Tap Record Video
4. Select 4K at 30 fps (or higher)

That's it. Your phone has been recording in standard HD by default — but with one setting change, every video you shoot from here on out will be significantly higher quality. Whether you're capturing a behind-the-scenes moment, a quick testimonial, or a product shot, this small tweak makes a real difference without spending a dollar.

It won't replace a professional shoot, but it's a simple, immediate way to level up the content you're already creating.

Connect with Andrew Stone:

1. LinkedIn: https://www.linkedin.com/in/andrew-stone-867b79196/
2. Facebook: https://www.facebook.com/astonephoto111
3. Instagram: https://www.instagram.com/anstone111/
4. Website: https://andrewstonephoto.com

Connect with Jesse:

1. Website: https://delegatedtask.com
2. LinkedIn: https://www.linkedin.com/in/jesse-hoss-✅-635b61276/
3. Email: info@delegatedtask.com

Thank you for listening to the show, your support means so much!

-Jesse Hoss