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Character: What You Have When You Have Nothing Else – #MisterImpact

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Jason Calacanis’s Top Tips for Angel Investors

In the world of tech investments, Jason Calacanis needs no introduction. Having founded his first company in the dot-com era and making a name for himself as an angel investor in the early days of the industry, the 46-year-old has bagged six unicorns to date, including Uber and Thumbtack, racking up a personal fortune in the ballpark of $125m.

Calacanis has invested in 150 startups total, with plans to double that over the next five years. And as a media junkie, he regularly sits down with the best in the biz to talk shop on his podcast, ‘This Week in Startups’. Last year, he sat down to talk to Thinkruptor, in an interview that was published in our very first issue. Some of the advice Calacanis had to give in that first feature is timeless and invaluable, worth going over again and again.

Here’s the gist of it. The full feature is available in Issue 1 of Thinkruptor magazine, on our app on iTunes and Play Store.

Work out if angel investing is for you

According to Jason Calacanis, to be an angel in early-stage startups you need to have a stomach for risk and only invest the amount of money you can stand to lose – typically 1 to 10% of your net worth.

Join a syndicate to get started

Learn the ropes of investing by joining a syndicate (there are many listed on sites such as AngelList and SeedInvest). You’ll benefit from the experience of your ‘lead angel’, start building your contact list and can get skin in the game for a minimal amount, often as little as $1,000.

Check investments for these characteristics

  • At least two founders (in case one quits);
  • A product or service already in the market;
  • Six months of continuous user growth or revenue;
  • Notable investors;
  • 18 months of runway.

Keep an eye out for ‘wildcards’

“When someone tells me they have a founder they want to introduce me to, but they’re worried because the person is a wildcard, I set that meeting up for the next day,” says Calacanis. “Angel investors are looking for wildcards, because the best founders are typically inflexible and unmanageable, pursuing their dreams at the expense of other people’s feelings.”

Add to the ecosystem

Calacanis recommends systematically building your network. Create a list of your co-investors and reach out to them. Keep them in the loop of any interesting deals that come your way, and ask them to do the same. Before long you’ll have a bulging rolodex.

jason calacanis

Help your founders

Look for ways you can assist the founders you invest in. This might involve helping to publicize their product or service, keeping an eye out for talented potential employees and providing feedback. You might also have more specific skills perhaps in sales or marketing, that you can bring to the table.

Demand monthly investor updates

According to Calacanis, a warning sign that a startup is in trouble is a sudden drop-off in communications. “I’ve gone on an industry-wide crusade to get founders to send monthly updates. That’s primarily because I want to read them, but it’s also because the simple act of reporting on how their business is doing creates a discipline in founders and continues an ongoing dialogue with their investors.” The benefits go both ways too – investors who are kept in the loop are going to feel more inclined to put their hands in their pockets for bridge rounds and further funding.


Good email habits make founders more approachable (and better at networking)

One of the downfalls of having a successful career is that we begin to lose touch with current events and popular culture.

How creative office spaces boost productivity and loyalty

One thing both startups and established international corporations have in common is trying to increase productivity and incite innovation. A major factor in achieving this over the past several years has been figuring out which workspaces work best.

In the next quarterly issue of Thinkruptor Magazine, we’ll be touching on the subject of managing today’s startup staff and product teams and asking a few experts for advice on this. In the meantime, we took a look at how some growing companies are applying creativity in office spaces to be more successful. (more…)

4 Non-US cloud startups to keep an eye on in 2018

The vast majority of startups and established cloud companies that received any significant funding over the last year are, unsurprisingly, based in the US. As expected, Silicon Valley cloud startups are getting the bulk of the attention and cash, although there are a few startups making waves half a world away from California. (more…)

Why entrepreneurs and investors need a dedicated quarterly magazine

When Thinkruptor first launched, we saw it as a monthly magazine for seasoned tech entrepreneurs, executives and investors.

With a motley crew of angel investors, business consultants, and media professionals behind it, we realized there was very little in-depth content aimed specifically at us. Initially, we thought a monthly magazine would do the trick. We were wrong. (more…)

Basic design language that every entrepreneur should know

We’re going to make a bold claim – design and branding have never been more important than in the age of the internet. Understanding design basics and best practices when starting or running a business, in today’s day and age, is just as important as understanding business models or overhead and accounting. (more…)

The one skill every business leader should have

Leadership is something we’ve defined and redefined time and again, over centuries. Various types and sizes of leadership roles often change with the times. Whatever our definition, only a few characteristics and skills remain the backbone of what makes a leader a leader – and one of those skills stands out among the rest. (more…)

In the new February issue of Thinkruptor Magazine

When we set out to create Thinkruptor, a magazine for entrepreneurs and investors that would showcase and foster groundbreaking ideas and change minds, we never assumed how much it would teach us and change our own perspective of the world we live in. And we’ve only published two issues so far.

From here on in, Thinkruptor will be a quarterly magazine, with loads of in-depth white papers, reports, and other goodies to be expected between each issue. But more about that later.

Before we get into exposing our devious plans for 2018, let us run through what we’ve explored and whom we’ve spoken to for our February issue of Thinkruptor Magazine.

The new issue of Thinkruptor Magazine is now available on the App Store and Google Play Store.

A Colorado sit down with venture hero Brad Feld

First, we need to thank Brad Feld once again for bearing with us and gifting us and our readers with a no-holds-barred 12-page interview. Brad took the time to explain the inner workings of venture capital relationships, both from the investor and the founder point of view.

“I don’t think you should ever do a deal with somebody you don’t like, period. When you take money from an investor, they have just become your partner for the long term. If you don’t like your partner or you don’t have a good feeling from them before you do the deal, and you can’t get comfortable with them based on talking to other entrepreneurs, other investors, other people who might know them, why in the world would you want them to be a partner in your company?”

For more insight from Brad’s vast experience, pick up the new issue of the mag and follow what he’s up to on Feld Thoughts.

Reinvent Yourself with James Altucher

Often hailed as a startup guru and chief chronicler of the disruptive economy, James Altucher proved to be as fascinating as he sounds in a one-on-one with our interviewer. Altucher has worked with the likes of the Wu Tang Clan, Time Warner, and possibly everyone in between. In this interview, he talks, quite literally, about flipping the scripts we’re given when we come into this world.

“We’re all given a script when we’re growing up. When I was four years old, my dad said to me, ‘You’re going to go school now.’ I said, ‘Well, I don’t want to. I just like playing.’ And he said, ‘Well, you go to preschool for two years, then kindergarten, Grades 1 through 12, college, graduate school and maybe postgraduate, then you work for 30 or 40 years until you’re grandpa’s age, and then you retire.’ I remember crying.”

The young gun who bootstrapped a 400-employee startup

Experience doesn’t always come with age. More often than not, it follows adventurous spirits and at a much earlier age. Twenty-something Appster founder and CEO Josiah Humphrey is living proof of that. Humphrey talked to us about skipping school to go see a Tony Robbins event, having his entire marketing team walk out of a mid-stage startup, and how his parents reacted when he started his first business venture in his teens and decided that continuing his academic career wasn’t right for him.

“When I dropped out of high school, my parents were very supportive. They saw that I was determined and knew that they wouldn’t be able to change my mind. I’ve always known that I want to follow what I’m interested in. But that has evolved over time and I’m always looking for new challenges.”

If you haven’t already, be sure to sign up for our soon to be released free Thinkruptor weekly digest, to stay up-to-date on industry events and hear what we have coming up in the next weeks and months.

18 Amazing world locations where startup founders can (and should) go on workation

With a growing global remote workforce, busy startup founders and entrepreneurs might be missing a vital piece of the big picture. While the first years of operating a successful startup can be chock full of riveting moments and business travel, it also means plenty of sleepless nights and no vacation time. (more…)