If I could start over: Investing & career advice for millennials

You’re all fucking doomed.

Well, not exactly. Actually, millennials are in a decent position to do well with themselves if they understand a few rules that us Generation Xers and the Boomers before us had no idea about.

It’s said that you shoudn’t trust anyone who was born before 1965 for life advice. I sneak in by a few years so shut up and pay attention while I get all sage on your asses. These are my gospel rules to live by and they’re proper worth remembering because I’m awesome.

  1. When you buy a Big Gulp at the 7/11, filling 1/3 of your cup with Slurpee ice acts as a great way to keep it ice cold in the summer. The clerks don’t care about this because the prices are about the same and those guys are paid nothing and hate everything about their lives. Fill your pants with the hot dog ketchup, they don’t give a shit.
  2. Your parents will always tell you the safest option is best. This is because they always took the safe option. It’s also why they hate their lives. Ignore this advice. Take risks.
  3. You will never succeed by sending out job applications, no matter how many you put out there. Take any shitty job going and be prepared to work overtime for free, offer excellent ideas aimed at making your workplace more money, find ways to make your boss look smarter than you, excel all the time in every area, and happily be paid crap while doing it. This will pay off.
  4. When you’ve taken care of #3, tell your boss you need a promotion or a pay-rise or you’re gone. Repeat every six months. When that conversation moves from “Yeah, okay, no problem,” to “welllll,” get a new job and don’t look back.
  5. You must not think of yourself as an employee. You’re a contractor. You’re a business. Employees wait for a pay rise to be given to them. Contractors tell their client what they charge. If you’re doing #3, this will not be a problem. If I’m not getting a pay rise or promotion every six months, I’m taking my roadshow elsewhere.
  6. Every single paycheque, peel off $100, any way you can manage it, and sit on it until you have an even thousand. Then pick a stock and buy it. Buy shares in things you use, that are in new industries that are starting to mature. Don’t buy anything that costs more than $1 per share, or that society has a hate on for, or that hurts people. Chicks dig it when you say, “Oh, I own shares in the company,” and you’re not talking about Monsanto.
  7. If that investment drops 20% but you still use the thing they create and sell, ignore the drop and buy more. Markets are dumb and they’re dominated by old men who don’t know anything beyond the last quarterly results. If you know fashion, buy fashion stocks. If you know tech, buy tech stocks. Those old men will catch up eventually.
  8. If that investment doubles, take out your original stake and reinvest it in something else while letting the leftover profits ride.
  9. If the market takes a big drop, buy the things that dropped most, if they dropped for no good reason.
  10. Never believe a CEO that was running a different company six months ago, and another six months before that. It takes a lot to lose a CEO, so a spotty track record is a bad bad sign.
  11. When you see a stock under 10c driving up, but can find no reason for it to be doing so, someone is backing up the truck. News is coming. Buy into the silence and sell when that news hits.
  12. Buy based on management reputation. Balance sheets are an inaccurate gauge of future success. Past success is a much better metric.
  13. Growing marijuana is farming. Nobody ever got rich buying farm stocks. If there’s no value add or differentiator, steer clear.
  14. Buying a stock that is being promoted hard is not a dumb move. Being the last one still holding it when the promotion ends, is.
  15. Buy private equity. Yes, I know you’re not a millionaire, but you don’t need to be. People who called Twitter when it was brand new and offered to invest 10K with them got share certificates that, today, are worth tens of millions. Startups bleed for funding, and they’ll take your pennies if you offer – and they haven’t yet got 50 investors.
  16. If you frequent a cafe and it’s getting crazy and the whole neighbourhood loves it, talk to the owner and ask if he’s looking for investors. 5k will open a door, and you’re a partner in something getting big. Sure, you might not be able to sell when you want to, but let it ride, children. Some day, someone will want your stake and pay a premium for it.
  17. Dividends: Understand what they are and who pays them. It’s an old school concept these days, when every company is in a ‘growth phase’, but dividend cheques are a nice thing to receive every few months.
  18. Get your credit report and understand it. If you don’t understand it, take it to your bank and ask them to explain it. You’ll be shocked how many dumb issues that aren’t your fault are killing your credit score.
  19. If you’re sharing an apartment, put the bills in your name. Most people don’t because they don’t want to be stuck with a bad bill, but the other side is, regular payment makes your credit score look great.
  20. Open credit cards, use them when needed, pay them off before the end of the month, and then lock them in a box never to be used again. A handful of credit cards at or near zero is a good look on a credit report.
  21. If you need cash for a short period, go to a bank to get it. A four month loan, again, looks great on credit if you paid it all promptly.
  22. Go onto Linkedin and find every company you’d love to work for, then find the person at each of those companies who would probably be your boss if you did work there (not the HR person but your actual manager), and then connect with them. Lie about it. Say you’ve done business together before. Most people will just okay any connection and not ask questions. Once you’ve got a few hundred potential employers on your list out there, start posting articles to the site that position you as a ‘thought leader’ on a topic. Then put out a piece that says you’ve decided it’s time to look for new opportunities and will be taking lunch meetings all next week. It’s cocky, but it works.
  23. Don’t send out resumes. Use a tool like Prezi or Squarespace to turn your resume into something interesting that will be passed around.
  24. If you wait for a job to be advertised, it’s already gone.
  25. If it’s 2AM and you’re in a bar on Granville St in Vancouver, you’re half as good looking as you think you are.
  26. No good business deal was ever sealed at a strip club.
  27. No bad business deal was ever sealed at a strip club.
  28. You will never own Canadian real estate. The sooner you get that into your head, the easier you’ll sleep. That industry is no longer accepting local offers.
  29. Find a good rental and paint it up nice so the rent you’re paying feels like a good deal and NEVER TELL YOUR LANDLORD THAT YOU MADE IT NICE. No tenant ever got kicked out for painting an apartment for free. Unless you’re the sort of dumb ass that wants a black bedroom.
  30. Buying a cheap used car is a false economy because one dropped clutch doubles the cost of the vehicle. Lease if you’re doing short trips, buy last year’s model (second hand) if you’re driving a lot. Or use a car co-op. Car payments top out at around 5% if your credit is crap and go down to 0% if it isn’t. A new car is not as expensive as you think, and not having to repair it for five years helps cover that cost.
  31. Do not bike to work. It makes you ‘that guy.’ Like telling a date you’re vegan, or that you ‘live the straightedge lifestyle.’
  32. Tattoos are no longer objectionable work wear, but limit the flaming death skulls and prison tats. The moment you add a teardrop to your face, your income tops out at the contents of an old lady’s purse.
  33. Own a suit. Wear it when you feel like you probably don’t need to. Being overdressed never, ever, ever hurts you.
  34. Don’t invest in Google, Apple or Microsoft. Because you’re not that asshole.
  35. Whatever conventional wisdom tells you is the right path, that’s the wrong path. Conventional wisdom is a fast track to the middle, and nobody is happy or rich in the middle. Find profitable niches on the edges. Find the good things the market has ignored. Invest in companies that had bad news and are oversold. Invest in ‘turnarounds’. Get out just after everyone else gets in.
  36. Want to start a business? Use other people’s money. If you can’t get anyone else to give you their money, work on your presentation and concept.
  37. Go harder than the other guy.
  38. Start earlier than the other guy.
  39. Finish later than the other guy.
  40. Understand the other guy thinks you’re a dick because you’re making him look bad and is just waiting for his chance to take you down.
  41. Have a Plan B.
  42. Your Plan B is terrible. Get a better Plan B.
  43. Make your parents admit they were wrong.
  44. When you think that person is the one you should marry, give it another six months. I’ll save each of you about $400,000 over the course of your life if you remember this one.
  45. Beauty departs, unless it’s found within. But a sense of humour just gets better.
  46. Never hire staff with Obsessive Compulsive Disorder. Yes, they’ll complete every task quickly and efficiently and they’ll be at work right on time, but then they’ll spend two hours fucking with the light switch.
  47. If someone tells you a coal company is a great investment opportunity, punch that person right in the junk. Lots. I’ll hold them down.
  48. Nobody who ever borrows money from you intends to pay it back. Nobody. Get collateral.
  49. Don’t throw out anything that someone might pay for at a garage sale or on Craigslist. Which is pretty much everything.
  50. Haggle on every purchase over $100. Ask for a cash discount. Ask for a ‘nice guy’ discount. Tell them you’ll get it from somewhere else. Walk out if necessary. They’ll cave.
  51. Never pay a traffic ticket. Always go to court. Half the time, the cop doesn’t show and you win. If they show, ask when their equipment was last calibrated. If they say it was calibrated recently, ask to see the log books, which they won’t have with them. You will always win.
  52. If someone rips you off, don’t threaten to sue. Just go public and shame them. Tough to do business with a bad BBB rep.
  53. The only advertising that is worth the money is late night TV advertising and Facebook ads (pay per click). Nothing else works.
  54. The amount of egg profiles following a Twitter account is in direct correlation to the untrustworthiness of that individual.
  55. Find a business that is on its last legs and take it over for pennies. It’ll probably fail. But if it doesn’t, and you can turn it around with your wily smarts, you just scored. I got myself a half share in a magazine this way, that was a roaring success three months later and I sold for a nice profit.
  56. Always check the bed bug registry.
  57. Never work for someone you don’t like.
  58. Never like your boss too much. Hussy.
  59. Don’t buy medical insurance when you’re young. Figure out the cost, then put that much money into a savings account, or stocks. When you get sick, a decade down the line, you’ll have money to cover it. And if you don’t get sick, you just got a down payment on a home. Assuming homes are a thing by then.
  60. Always tell the server or bartender to ‘surprise’ you when ordering drinks. When they ask ‘what do you like’, say “I’m not making this easy for you. Be awesome.” You will be shocked how much awesomeness springs forth.
  61. If you do #60 and they give you the most expensive drink in the place, take it out of their tip.
  62. Always tip 20%. This is an investment. It comes back.
  63. Send thank you notes to colleagues.
  64. Share glory.
  65. Grow your own.
Disclaimer: ALWAYS DO YOUR OWN RESEARCH and consult with a licensed investment professional before making an investment. This communication should not be used as a basis for making any investment.

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