Why Loaning Money to Friends is Always a Bad Idea

Young man with glasses reviewing bills

Fifteen years ago, I learned this lesson the hard way.  A relative of mine hit difficult times in their finances and asked me for a $10,000 loan. You might be familiar with loaning money to friends. They hit hard times–job layoff,  financially damaging relationship, overspending on luxury goods and trips they couldn’t afford. So, why…

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Could You Have Created a “Dirty Cap Table”?

Oh, I know. When you started the business, you took investments from friends and family in small amounts just to get you started. Of course, that worked at the time. But… Enter the need for larger investments When you seek professional investors, whether organized angels or venture capitalists, one of the early questions you are asked…

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8 Smart Tips to Soliciting Friends and Family Funding

It’s great to start with a big dream as you contemplate a new business, but finding the money you need takes more than dreaming. As an advisor to young entrepreneurs, I find that many are a bit naïve about how the investment process really works. For example, I just read an otherwise impressive business plan…

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The Right Way to Get Funding from Family and Friends

Most entrepreneurs I know are so passionate about their new idea that they are surprised when family and friends don’t line up to invest in their new venture. Yet they tend to ignore this problem, and move on quickly to professional investors. They don’t realize that most Angel investors and venture capitalists will also decline…

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The Pros and Cons of Starting a Business with Friends

I first met Jonathan Wasserstrum, one of my best friends and now a co-founder of TheSquareFoot and our company’s CEO, nearly two decades ago. We became friends almost immediately after meeting in high school, and we’ve been buddies ever since. A few years later, when I went to college at UT, I met Justin Lee,…

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Entrepreneurs Need More Relationships and Fewer Friends

Successful entrepreneurs understand the difference between a good business relationship with more people and having more friends. In fact, the focus on social networking platforms, starting with Facebook, has destroyed the meaning of the word friend and even changed it from a noun to a verb. It’s now common to have hundreds or thousands of…

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Should You Go Into Business with Your Friends?

Either you’ve thought about it or you know someone who has: going into business with a good friend seems like a wonderful idea. Why wouldn’t it be? You already trust them, you know their habits, and you can communicate and aspire to the same goals. It does seem like the perfect mix, but there are…

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10 Ways for Entrepreneurs to Meet Cash Flow Peaks

The “valley of death” is a common term in the startup world, referring to the difficulty of covering the negative cash flow in the early stages of a startup, before their new product or service is bringing in revenue from real customers. I often get asked about the real alternatives to bridge this valley, and…

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