In early 2017, I was shown an opportunity to invest in a US$6.5m simple agreement for a future equity (SAFE) note issued by BuildDirect.com Technologies Inc., a $1bn Canadian e–commerce company. 

All of business’ facets looked solid 

My client had made previous investments in the company and had a strong conviction in the team, the company, the market and this “new marketplace” opportunity. The company sells heavy construction supplies, such as tiles and granite, to contractors and home-improvement enthusiasts. 

Confidence builds when following ‘the smart money’ 

BuildDirect claimed to have developed an intelligent system to pre–position products in hubs around the country to cut the costs and time of delivery.  We were also confident because we were supposedly following “the smart money” – a major Canadian pension fund and other Silicon Valley venture capital firms were also investing. 

Many factors point to a ‘sound’ investment 

We were excited about the model; its artificial intelligence (AI) platform and the business opportunity and history of the company, which was 16 years old and had been grossing more than C$150m (US$120m) a year in revenues. We also had clients that used the company’s services.  We made the investment, which was around US$650,000. Within a few months we were notified that, as expected, our debt had been converted to equity. 

Ten months later, we learned that the CEO had been fired/asked to resign. He was the architect of the whole “marketplace” idea. Weeks later, we learned that the company had entered into receivership. It appears now to be a total loss. 

Even good ideas can lead to a premature fall 

Established companies can fail swiftly and dramatically. This company developed a very clever online marketplace, however they were utterly unable to execute it and ended up angering and losing their existing and long-standing vendors. 

Andrew’s takeaways – Avoid these errors to become a better investor 

Don’t blindly follow the smart money 

Just because big fund managers are buying into a company does not mean that those fund managers are right. They could just as much be wrong. Don’t take any comfort that you are investing with the “smart money”, meaning the professional investors. They are often under career pressures and other pressures that can lead them to bad decisions. If you want to invest, take the time to build your style and plan, and then follow it. An individual has considerable advantages compared to the pros. 

Have an exit plan 

No matter how good the investment is, no matter how experienced the others who you are investing in are, and no matter how much research you have done, always have an exit plan. Investing involves too much uncertainty; having an exit plan allows you to pre-plan what you will do when things go wrong. 

Mistakes in this story 

1. Failed to do their own research 

2. Failed to properly assess and manage risk 

• Assumed past performance would continue 
• Bought an illiquid investment 
• Lacked influence over management 

3. Driven by emotion or flawed thinking 

• Let emotions drive their investment decisions 
• Were driven by FOMO 

5. Failed to monitor their investment 

• Failed to review investment strategy regularly 

6. Invested in a start-up company 

• Invested in a start–up that lacked various sources of funds 

The post How Poor Execution Turns a Great Idea into the Worst Investment appeared first on My Worst Investment Ever.

Throwing good money after bad was an exercise in sunk cost and saving face

And the reason it was a bad investment was that after I started investing, I got into a cycle of giving them more money when they were desperate. And, it ended up being an exercise in sunk cost and the social difficulty of saying “no”, an exercise that ended up being quite expensive.

Andrew’s takeaways – Avoid these mistakes to become a better investor

Fundamental questions to ask about a start-up before investing in it

To avoid the above story when you look at investing in a start-up, I suggest you put it through the following test. But, don’t do it alone! Because you will be overly optimistic, I suggest that you test it with your most skeptical friend, oh, and write it down. If you get a “No” answer as you move through these questions just drop the whole idea (I learned this from my own losing start-up investments!) Question 1: Do you trust the person/people running the start-up? 2. Is the idea good? 3. Can this team execute the idea?

Ensure there is more than one funding resource behind a start-up

It is too easy for a start-up to rely on the original person who brought money to the deal. Sometimes the money source thinks that they can hold a larger share of the business if they don’t bring in other investors. But this thinking can lead to the trap of being the sole supplier of capital. Before you put money in a start-up, work with the founders to identify the next sources of funds. Then require the management team to pitch to these sources, go with them, see how it goes, then use that information to determine if you will invest.

Mistakes in this story

1. Failed to do their own research

• Failed to do their own research

6. Invested in a start-up company

• Invested in a start-up that lacked various sources of funds

Learn about the six ways you will lose your money and how to avoid them here.

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