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Aaron Jensen

Musical composer

Oct 5, 2026

13:01
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?
13:11
Yeah, I think it goes back to just understanding the future of where things are headed.
13:21
I've certainly started a lot of companies that haven't worked out.
13:25
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.
13:34
And I've certainly had many, many losses.
13:38
But it takes those losses.
13:40
It takes those those learning experiences in order to build up to the wins.

10 MINS LATER

24:09
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?
11:11
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?
11:28
Yeah, I think as an entrepreneur, you have to be willing to pivot.
11:32
You have to be willing to change what you're doing because the world changes fast.
11:39
The world changes very, very fast.
11:41
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.
11:55
So we started looking at selling in late 2024. because we could see AI on the horizon.
12:04
It was coming for our business.
speaker_2ADVERTISER
15:03
Find yours at T-Mobile.com.
21:16
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.
21:24
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.
21:54
But yeah, so to your question about our offer and our model, how that changed as we got into insurance, it certainly did.
22:02
So we found the ground level of fit with our $2,000 one-time offer in insurance, and we got the thumbs up.
22:12
That worked, and we were super happy.
22:14
But we wanted to continue to evolve on that and to tweak that offer to make it even better.
22:20
So there were a number of things that we did all in mind of trying to escape the hamster wheel.

22 MINS LATER

44:33
What would you advise or counsel a fellow business owner who's looking at a dying niche but is afraid to pivot?
speaker_0HOST
0:29
For those that haven't had a chance to catch up, you know, break it down for us.
0:33
Sure.
0:34
We'll go back a little bit.
0:35
So 1870 Holdings is the holding company that owns Midwest Bank.
0:41
And about three years ago, maybe a little longer, 1870 Holdings changed its designation as a holding company.
0:48
from a bank holding company to a financial services holding company.
0:53
And what that allows 1870s to do is to own financial related businesses.
speaker_0HOST
3:50
What else is happening at Midwest Bank in 1870s?

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