Let's see... There's are several sides to this coin...
Growing up in Brooklyn, my Dad was a HUGE horse racing guy. He'd go at least 4 times a week. So as a little kid, we used to go to Aqueduct & Belmont all the time. Every once in a while he used to have me walk up to where the horses were trotting out and pick one. The first one I got right gave me a rush I have never found anywhere else.
As I got older I started learning how to read the form. As a teen in Florida, me and my Dad used to go to the greyhound track every weekend and bet the horses on simulcast.
Now I don't play the horses nearly as often. I basically bet the triple crown and the Breeder's Cup.
Also, me and my Dad used to play cards a lot. 5 Card Stud was one of the games. In 5th grade during recess I used to play cards with some friends, and eventually we got poker games going during lunch.
When I moved to Florida, I didn't play poker for ages, until the Hold 'Em/online poker boon happened. I went through a lot of money during my freshman year in college playing online poker. I was OK but way too predictable.
However, I'm a reasonably good live player because I can pick up a lot of tells. As I've learned the intricacies of Hold 'Em I like the game. I just don't have the money to really play that often, and poker is sort of like golf in that you have to play consistently to really improve.
My sports betting foray started when my older brother (in his 20s) used to call me (age 11-12) for picks straight up. I was actually pretty good. Since then I kept a book of all my picks/analysis. In high school I started also picking ATS.
In college I started betting sports at the same time as I started playing online poker. I'm much better as I've been a sports fan for many years (I went to college to be a sportscaster) but can be rational and objective at the same time. I used to love parlays, and went to that well often after turning $5 into $205 on an 8 team parlay during the Sweet 16 in the NCAA tournament (the year Morrison
) That was back when Bet365 took American customers.
Over the next few years I started to get a good feel for betting sports and figured out what I was good at and what I'm not good at. I also settled into 2 main books: 5Dimes & Sportsbook.ag, even though now I might add Intertops.eu to the mix as I'm weary that 5Dimes is still a .com domain.
The "light" clicked on my Junior year of college. I've been concentrated on football ever since, dabbling in other crap that, outside of golf, has hurt me.
Now I'm mostly an NFL bettor who will occasionally bet other sports in opportunistic fashion when I spot an error (for instance, the Kemba Walker NBA draft prop; he was never going 5th or before). I understand the runs involved and don't get emotionally wrecked by losses like I used to.
My biggest bets are futures, since these provide great opportunities to exploit public perception (I had the Chiefs winning the AFC West @ +800 & Auburn winning the SEC West at +675 last year). I've learned to cut the dabbling out and focus on what I'm good at.
I still bet small since I don't have a lot of income, but I make concentrated plays and will be aggressive in these plays, which I think is the way to go.
I almost never bet parlays as they are, for the most parts, traps to lose your money in (this applies to teasers too).
Also, the boon of fantasy football has created a wonderful world of player props which, after watching a month of the season, I am pretty good at finding winners (look for ones with good probabilities of going over; never bet unders).
Last year I finally was close to the holy grail of a 65% win rate, which has been my goal for some time. If I had $25K in disposable income, I would go pro.
Throughout my time in this I've learned two very important lessons:
1. If you don't have the ability to say no, you'll never win.
2. If you have a bad string of luck, there's a pot of gold waiting for you eventually.
And there you have it.
BTW, I'm only 23. And I know for a fact picking NFL games was easier when I was 13.
Parity nowadays