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3 Lessons Learned from My First Startup Investment

3 Lessons Learned from My First Startup Investment

In 2011, I made a major investment in a startup company for the first time ever. The company is called Help Scout—they make web-based help desk software that makes customer service a breeze for any business.

Ever since I invested, countless people have come to me with questions about startup investing. They think it’s simple—you find a great idea and throw money at it until there’s a huge IPO that makes you filthy rich. Right? Isn’t that how it works?

Nothing could be further from the truth. If you want to invest in a startup, here are the three key bits of information you need to know:

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1. You’re not actually investing in a startup.

You’re investing in people. When the time came for Help Scout to start seeking angel investors, the three guys behind it were so cool that they wouldn’t even ask me to invest. Why? Because I’d actually been investing in them since they were in college.

Prior to forming their own company, they had all worked with me as interns, and then as professionals when they branched out and created a web design firm. Over this period, I took an active interest in their growth as entrepreneurs and young men. By the time they were ready to launch the company, they thought I’d already done my part.

When I finally heard they were looking for investors, I asked to see the presentation they were showing to potential candidates out of curiosity. I read it and was sold. “Can I invest in this?” I asked them.

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“Robert,” they said, “this is very risky. There’s absolutely no guarantee you’ll see your money again.”

“Listen, I’m not investing in the business. In fact, I’m still not sure I even understand what you’re doing!” I explained. “But I believe in you guys. I always have. And I’ll believe in you forever.”

With that, they had another investor.

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2. The startup’s concept doesn’t have to make sense to you.

To this day, I do not fully understand Help Scout. I just don’t have a techy brain, and I’m aware that ideas in that field don’t always make sense to me. But I also never thought a hot dog on a stick would sell so well.

The point is to not get so wrapped up in an idea that you think is amazing, because amazing ideas don’t execute themselves. Even amazing ideas will fail unless you have a team of extraordinary individuals putting in 15-hour days week in and week out.

The first time I attended a TechStars event (which is the startup accelerator that gave Help Scout its start), just about every company that did their pitch wowed me. By the end of the day, I was ready to write checks to ALL of them.

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“What’d you think of this one, and what about that one! Weren’t those ideas amazing?” I said to some of the more experienced investors. I was stunned when, immediately, they dismissed them. “Those people will never be able to pull it off,” they said. Don’t focus on the extraordinary ideas. Focus on the extraordinary people, even when you don’t fully grasp what they’re pitching.

3. Don’t do it if you need the money.

This is one of the first things TechStars will tell potential investors. If you are investing your last $10,000, they do NOT want your money. If you are investing with the hope that you’re going to get a huge payday, go elsewhere.

I didn’t invest in Help Scout to make money. In my mind, that’s nothing but a bonus if it happens one day. I’m investing in the guys. When I wrote the check, the money, as far as I was concerned, became gone forever.

If you’re not comfortable with never receiving a dime in return, investing in a startup is not for you. Period.

If you’re interested in investing in a startup, the main thing to learn is to find the best group of innovators and hard workers that you possibly can. Look beyond the idea and assess the people who are going to be putting in the hours. Look for people who, more than anything, you want to see succeed beyond their wildest dreams. Don’t invest in the company. Invest in the hearts and minds of those behind it.

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Published on September 17, 2018

How Being Smart With Your Money Leads to Financial Success

How Being Smart With Your Money Leads to Financial Success

Achieving financial success is not something that just happens. Maybe if you win the lottery or something, but for the average person like you or me, it comes from a series of small steps you take over a long period of time.

With each step, you form a new smart money habit. And with each smart money habit, you build towards financial independence.

So what sort of habits can you form to get on that path? Let’s take a look at smart money habits you can start today to get you closer to a financially independent future.

1. Avoid being “penny wise but pound foolish”

It’s tempting to try saving a couple cents here and there when buying small items. However, that’s not where the real money is saved. You’re putting in extra effort for something that doesn’t move the needle.

You get the most bang when you’re able to cut down on your bigger bills. For example, finding a lower interest rate for your mortgage could save you $50+ per month. And cutting your transportation bill by purchasing a cheaper car or taking public transportation can provide large gains as well.

So, look at your recurring expenses such as housing, transportation, and insurance, and see where there’s wiggle room. It’s a much better use of your time than trying to pinch pennies here and there on smaller purchases.

2. When you want something big, wait

Impulsivity can get you in trouble in most aspects of life. Finances are no different.

It’s human nature to see something and want it right then and there. It starts as a kid in the checkout line at the grocery store, and it continues on through adulthood.

We get an idea in our head of something we want, and it’s hard not to go out and get it right then.

A good example is wanting a new car. Perhaps you’ve had your car for several years. It’s crossed the 100k mile mark. Maybe maintenance is due, and you’re annoyed that you need to replace the timing belt or purchase new tires.

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So, you get the itch.

You start digging around online, and you realize you could trade in your current car for something newer and more exciting… all for a few hundred bucks a month. Then you get obsessed.

Here’s where you have to take a step back.

Your newfound obsession is clouding your judgement. Rather than giving into the impulse, wait it out.

Set a timeframe for yourself. Maybe you come back to the decision three months down the road. See if the obsession lasts.

It might, but often, a funny thing happens. Often, you forget about it. And often, you find that the new car wasn’t a need at all.

The impulse faded. And you just saved yourself a ton of money.

3. Live smaller than you can afford

You finally get that big raise. And you want to celebrate – and why not?

You’ve been looking forward to this forever. And after all, it was all due to your hard work.

That’s fine, splurge a little. However, make it a one-time deal and be done.

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Don’t get caught in the trap that just because you’re now making more money, you should spend more.

Too often, people get more money and feel like they that gives them the means to buy a bigger house, a bigger car… you know the drill. Resist.

The fact is that living smaller than what you can afford is one of the fastest ways to build savings.

But if you constantly upgrade as you begin to make more, then you’ll never get ahead. You’ll just build up more debt along the way and have just as little wiggle room as before.

4. Practice smart grocery shopping

Food… it’s one of the biggest portions of any budget. And if you’re not careful, it can be one of the biggest drains on your wallet.

But luckily, there are a few things you can do to ensure that you stay smart with your money when buying groceries.

Create a grocery budget

Set a strict weekly grocery budget. When you know how much you can spend on groceries, you can then plan your weekly menu around it.

Once you know what all you need, you can go shopping and keep a running tally as you shop to ensure you’re on track.

I tend to do this in my head, rounding for each item. However, writing it down as you go would probably work best for most people.

Make a list… and never deviate

Never go to the grocery store without a list. If you go to the store with a ballpark idea in mind, you don’t have a true ide of what you need.

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You’re not well-researched. You don’t know what the sales are. As a result, you’re going to make decisions on the fly.

These impulse decisions will lead to overspending, which will derail your grocery budget.

Eat before going grocery shopping

It’s also important to eat prior to going to the grocery store. Hunger is a powerful force.

If you’re shopping on an empty stomach, everything is going to look good. In particular, you may find a lot of ready-made, processed snacks will look enticing.

After all, you’re hungry now and that food is easily available. So subconsciously, you may lean towards those items.

Unfortunately, not only are those items typically less healthy, but they’re likely more expensive. You pay for convenience.

However, when you eat prior to shopping, then you’ll shop with a clear mind. Your hunger won’t cloud your judgement, influencing you to make poor decisions like a cartoon devil resting on your shoulder whispering in your ear.

This makes it much easier to stick to your grocery plan.

5. Cancel your gym membership

Now that you’re all set on your food, it’s time to get smart about managing your budget in terms of physical fitness. And let’s begin by avoiding the gym. The gym bill, that is.

The average gym membership costs around $60 per month. That’s $720 a year.

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Yet, two out of three gym memberships go unused. That means two-thirds of people who have a gym membership are literally giving away almost a thousand bucks a year. It’s crazy!

I recommend seeking an alternative. One good alternative is to look into fitness streaming services.

Streaming services allow you to stream hundreds of workouts like Insanity and p90x, right in your own home for around $10-20 a month. That’s $40-50 less a month than the average gym membership.

Of course, then there’s the free option. The internet is full of free workouts that you can do on your own with minimal or no equipment.

For example, there’s the Couch to 5K program, that I personally used a decade ago to ease myself from couch potato to running my first 5K race. If I could do it, anyone could.

Then there are free resources like reddit that have limitless information on workouts. The Fitness subreddit has done all the research for you, populating workout tips and detailed workout routines for anyone to use in their wiki.

There are several routines that require no equipment. And you can join in on the subreddit to become part of the community, making it easier for those seeking comraderie and encouragement in their fitness goals. All for free.

It’s baby steps… And baby steps can start now!

I’ve never met anyone that can’t stand to be a bit smarter with their money. And on the flip side, anyone can get smarter with their money. But remember, it doesn’t happen all at once.

Begin by fighting your impulses. Prepare for the week and be smart at the store. And cut monthly expenses like gym memberships that are overpriced and you probably aren’t getting your money’s worth out of anyway.

The devil is in the details. And the details can change your lifestyle and prep you for a financially independent future.

Featured photo credit: Unsplash via unsplash.com

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