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