A
Aaron Jensen
Musical composer
4
APPEARANCES
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Oct 5, 2026
What Actually Scales: Aaron Jensen on Building, Selling & Scaling Multi-Million-Dollar Companies
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13:01Daniel LycisHOST
How do you actually know when a business is a sell versus a keep and build? What specific emotional or financial signal you listen for?

Aaron JensenGUEST
Yeah, I think it goes back to just understanding the future of where things are headed.

Aaron JensenGUEST
Most of my companies have failed, you know, and that's that's part of that's just part of being an entrepreneur is you're going to have wins, you're going to have losses.
10 MINS LATER
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24:09Daniel LycisHOST
Mr. Aaron, to wrap up our discussion for today, what's a non-negotiable core principle you've carried through every venture from door to door to SaaS or SaaS and now into a building reach well that you bet your next company on?
Aaron Jensen on Building and Selling Companies, Scaling to $20 Million, and Reinventing Insurance | Entrepreneurship 101
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11:11Daniel LycisHOST
Why walk away from a comfortable win to build a modern insurance agency? What did you see in that legacy and sexy industry that the other high level tech entrepreneurs were blind to?

Aaron JensenGUEST
You have to be willing to change what you're doing because the world changes fast.

Aaron JensenGUEST
And my main motivating factor for wanting to sell the company was it was fear of AI and what AI was doing on the horizon.

Aaron JensenGUEST
So we started looking at selling in late 2024. because we could see AI on the horizon.
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15:03speaker_2ADVERTISER
Find yours at T-Mobile.com.
How a Business Pivot Created an 8-Figure Exit | Aaron Jensen
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44:33

Jeremy ShapiroHOST
So tell us about the new model and the unique offer you had to the insurance space and how that varied from what you were doing previously in the real estate space.

Aaron JensenGUEST
yeah and i want to highlight on one other thing here too jeremy that you just kind of touched on is we changed one thing at a time i i think as business owners we fall into the trap of wanting to change and change and completely toss our business model aside and come up with something new but it's so important from a business owner perspective to just change one thing at a time that way you can track effectively if that change is working or it's not And eventually, the biggest change of all, we changed industries.

Aaron JensenGUEST
But yeah, so to your question about our offer and our model, how that changed as we got into insurance, it certainly did.

Aaron JensenGUEST
So we found the ground level of fit with our $2,000 one-time offer in insurance, and we got the thumbs up.

Aaron JensenGUEST
But we wanted to continue to evolve on that and to tweak that offer to make it even better.

Aaron JensenGUEST
So there were a number of things that we did all in mind of trying to escape the hamster wheel.
22 MINS LATER

Jeremy ShapiroHOST
What would you advise or counsel a fellow business owner who's looking at a dying niche but is afraid to pivot?
Midwest Bank President Aaron Jensen
0:41
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0:29speaker_0HOST
For those that haven't had a chance to catch up, you know, break it down for us.

Aaron JensenGUEST
And about three years ago, maybe a little longer, 1870 Holdings changed its designation as a holding company.
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3:50speaker_0HOST
What else is happening at Midwest Bank in 1870s?