Bullshit – Jason Calacanis Angel University

It’s difficult to make money in Angel Investing. Most Angels lose money. For people who want to spend money to learn how to lose money, there is Jason Calacanis Angel University. Because if you’re willing to flush cash down a toilet, why not flush some of that cash down the Jason Calacanis Angel University toilet.

Wait just one cotton-picking minute Glenbo, you Cranky old fart… who the fudge is Jason Calacanis and what is a cotton-picking minute?

That’s two questions so I’ll answer them separately.

  1. Jason Calacanis – Calacanis is the Kardashians of Angel Investing. He’s the Honey Boo Boo of startups. He’s the Snooky of Silicon Valley Shore. He’s what Paul Singh aspires to become when he grows up.  He’s Famous for being Famous. He’s famous for being the wrong person in the right place at the right time. Historically Calacanis was an early startup blogger, basically the author of a 2006 version of a DCInno-ish tech rag. He sold it to AOL when AOL was stroking checks to buy anything startup-eee. He soon left AOL and started blogging, podcasting, producing events, angel investing and selling picks, shovels, and blue jeans to the gold rush gold miners of the Startup Gold Rush (see post: Startup Land of the Blind).
  2. Cotton-Picking Minute (CPM) – CPM is an ancient term used by cave persons that use to be referred to as cavemen until the political correctness movement killed the caveman. Cotton-Picking Minute is often associated with the terms, “What in Tarnation,” and “Jumping Jehoshaphat.”

On April 19, 2019, Jason is bringing his traveling Jason Calacanis Angel University Medicine Show to town. A show that charges $500 to teach people who have money, how to not have money. (UPDATE: Jason invited me to the event. I attended and subsequently, put my tail between my legs in this post.)

Angel investing is more often a game that results in losing than winning. Few people make money and few mortals continue making angel investments for extended time periods. As an example, none of the people who I invested with back in 2009, including me are making new angel investments. We’ve all decided there are better ways to lose money. Like investing in boats and buying liquid Pez dispensers. Most of us have also stopped hitting ourselves in the head with a hammer because we found that there were better ways to cure headaches. Most of us have continued breathing because we like living.

This con, I mean this Jason Calacanis Angel University proposes to scam suckers into “investing” $500 to learn how to lose money (send me $10 and I’ll give you the secret to losing $490 less than Jason’s program and you can do my program in your underwear in the privacy of your own home). According to the announcement:

“Come join us during our Spring tour in Great Falls (near DC) for a half-day workshop + brunch for individuals interested in becoming professional angel investors. We’ll focus on five key topics: sourcing deals, evaluating startups, negotiating deals, portfolio and bankroll management, and post-deal efforts. “

Oxymoron alert! Professional Angel Investor? WTF Jason? Can we add Professional Angel Investor to the list of great oxymorons like Jumbo Shrimp, Military Intelligence?

Hey Jason, Angel Investors are not Angel Investors, they are Angel Tax Deduction Generators, they are Angel Philanthropist and please Professional? Angel investing is not a profession it is a hobby, it is a vice, it is grounds for divorce but it sure as shit isn’t a profession.

Let’s go over on the five things you will learn:

  1. Sourcing Deals – Call up the guys at Kleiner Perkins and ask them if they would like you to partner on any of their deals with you. Be sure to tell them that you want to write a check for $2,500.
  2. Evaluating Startups – Do a google search on the founder like this.
  3. Negotiating Deals – Right, because your tiny investment is going to affect the standard terms of the deal. Try it! See if the founder has a sense of humor.
  4. Portfolio and Bankroll Management – Don’t put your eggs in one basket and be sure to leave cash for follow-on investments. Blah Blah Blah Blah
  5. Post Deal Efforts – When your spouse and your mom asks, how is that investment in Chalant Health going… don’t say, “I just found out I was cheated,” say, “progressing well, I’m expecting it to be the next Theranos. Then send them this article.

Jason Calacanis is to startup investing what Dr. Phil is to Psychiatry. He’s to angel investing what, Carlton Sheets is to real estate investing. What will you learn in a four-hour seminar that will help you beat New Enterprise Associates while sourcing, negotiating and financing deals? It takes decades to learn how to underperform the market… you can’t learn that in 4 hours. You won’t even pick up the skills to invest like master investor… Adam Besvinick of  Anchorage Capital in four hours.

During the gold rush, only a few gold miners got rich. The consistent financial winners were the pick and shovel manufacturers. The Levi’s Jeans founder got rich. The sellers of equipment and dreams got rich. The dreamers… they typically suffered. Calacanis is selling treasure maps to dreamers. Unfortunately, X doesn’t mark the spot on those maps.

Still interested in the Jason Calacanis Angel University? Maybe you should dig a little more.

  • Calacanis claims to be worth over $100 million, yet he’s charging poor schnooks $500 per seat on how to lose money. He sells sponsorships to his events for $25,000 and $15,000. In other words, he’s nickel-and-diming his way to being worth $600.43 over $100 million.
  • Other red flags, from a New York Times article, “Most folks think I’m lucky, some say I’m a complete fraud, and a handful think I’m a brilliant hype man, and I don’t agree with any of them — I agree with all of them.” Me too… I think this is a brilliant scam by a lucky scam artist.
  • According to an AlleyWatch article, he’s quoted thusly, “I worked as a waiter and a bar back, but I knew how to fix computers. I was running scams on the side,” he shrugged nonchalantly. “Selling Word Perfect for $20.” Congratulations, Jason, has come a long way. He’s upped his game to scamming “Professional” Angel Investors, $500 per seat. A big jump from his $20 Word Perfect Scam.

Here’s the thing guys, angel schlimazels like you and me don’t get access to great deals! Great deals go to the professionals. Great deals go to the Jason Calacanises. If you want to invest profitably in startups than give your money to Randy Domolky at Private Access Network, or John Backus at PROOF or Bobby Ocampo of Blueprint Equity (see post).

I’m not implying that Jason is a bad guy. I’m just saying that spending $500 to learn how to lose money is a waste of time and money. You can listen to his podcasts or read his blog. Save your $500. You’re going to need it for Caps Playoff Tickets.

Update April 11, 2019: Be sure to link to the web version of this post to see the spirited comments. Jason Calacanis participates and demonstrates his strong ego, sense of personal security and the guy has a sense of humor. Kudos to him. He also engaged in twitter, see below.