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Running a Small Airbnb Business: Balancing Strategy, Competition, and Staying Afloat
Running a small Airbnb business is not as simple as handing over a set of keys and watching the bookings roll in. It is a constant balancing act—pricing strategies, keeping up with fierce competition, and managing the unpredictable nature of guest demand. Right now, I am operating two studio units in the city and two…
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Could My Home Insurance Disappear Too?
It is a late-summer afternoon, and I am visiting my cousin’s house in Milwaukee. Over coffee, he shares an unsettling story: his home insurance company dropped their coverage. The reason? A minor incident at his home led to a claim, and while it seemed small, the insurance company decided not to renew his policy. At…
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Five Years In: Are We Still a Startup—or Something More?
Another month has passed, and our business will be entering its fifth year next month. At this point, I often wonder—does it still count as a startup? The label feels both accurate and inadequate. We have grown and stabilized in ways I never thought possible, yet there is a lingering feeling that we are still…
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Is It Time for a New Car? Weighing the Pros and Cons
Lately, the thought of buying a new car has been on my mind more than usual. My 2016 compact car, while reliable and fully paid off, is beginning to show its age. It still gets me where I need to go, but little reminders of wear and tear are creeping in. The air conditioning fan…
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When Money Mixes with Friendship: How to Handle Loans Between Friends and Family
Money is never just about money. When it crosses the invisible line into friendships or family relationships, it carries the weight of trust, expectation, and sometimes, unspoken tension. I have been on both sides of the equation—borrowing and lending. In either position, the emotional toll can be heavier than the financial one. If you have…
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Protecting Digital Assets: Why Your Estate Plan Needs an Upgrade
The world is becoming increasingly digital, and so are our assets. From cryptocurrencies to social media accounts and online businesses, these digital holdings carry real value. Yet, many estate plans overlook them entirely. As I delve deeper into understanding the nuances of digital assets, I realize how crucial it is to ensure they are protected…
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Keeping the Peace: Why Family Trusts Matter
Turning 40 this year has me thinking more seriously about the future. My siblings and I are not married, and while our lives feel independent, we share a unique bond through something else—our family’s real estate. Our parents, though separated, have accumulated a significant number of properties over the years. Some of these are already…