Small wins

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In an early morning chat from Las Vegas, I was talking with Mr. Waldow about gambling – specifically, blackjack, and how I approach the table. My methodology is fairly simple: I set an amount I’m willing to play with, be it $5 or$ 100. When I step up to the tables, that’s exactly the amount I intend to play with and I will keep it in play as long as I can. When I win, I take the winnings and put them in my pocket, never to see the light of day again. The original bet, whatever size it is, remains in play.

At the end of the session – which admittedly doesn’t last very long, on average about 6 minutes – I walk away. Win or lose, once the original gamble is done, I walk away. If I’ve won $10 or$ 300, I still walk.

DJ had an interesting take on this:

“Well, that’s why you never win big. You have to play big to win big.”

That’s perhaps true in a system which is fair; casino gambling systems are inherently unfair, and designed to be as unfair as permitted by law. The only way you ever win – big or small – is to garner the favor of luck long enough to win something, and then walk away while you’re still ahead.

It’s absolutely true that I never win big at blackjack, ever. I never lose big, either. In fact, I rarely lose at all (I recommend Darwin Ortiz’s book Casino Gambling for the Clueless (amazon link)
for solid basic blackjack strategy). In the last 6 times I’ve addressed a blackjack table, I’ve walked away with a net profit between $5 and$ 70.

Do you have to play big to win big? In a negative expected value game, if you play big, you win big and lose big, but lose big more often. If you have limited resources – and don’t we all – you will be wiped out by gambler’s ruin. If you play with discipline and accept small wins, all those small wins add up to some tidy profits, tidy big wins.

This is one of the greatest flaws in thinking by humankind, and it pervades every aspect of leisure and business. I’ve lost count of how many people and companies that have completely abandoned solid, working systems in favor of a “play big” bet on things like collateralized debt obligations or social media. Folks spend and squander limited resources to “play big” only to find out that their previous system which accrued small wins was far more reliable.

Consider carefully before you decide to play big. Sometimes it works out.

Other times…

Play to win by being just as accepting of small wins as big wins.

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Comments

19 responses to “Small wins”

June 28, 2010

LynetteRadio

I'd rather bet small 100x than bet big 1x – maybe that's why I'm a sucker for taking on smaller clients.

Reply
June 28, 2010

PJ Mullen

Singles, walks and reaching base on error is how you set up grand slams. Small steps are as, if not more, important than the big ones.

Reply
June 28, 2010

Kristina

I am writing this comment from the Trump Las Vegas Hotel. I bet the Donald would 100% disagree about small wins. He has bet big his entire life, been bankrupt, and now is running a multi-billion dollar enterprise.

-Kristina (@djwaldow's wife)

Reply
June 28, 2010

Christopher S. Penn

Donald's a really, really interesting guy. That said, you know who kicks his butt? Warren Buffett, who goes for small wins, uses the small wins to pay for the big ones, but never, ever forgets the small ones – they're the fuel for experimentation.

Reply
June 28, 2010

Kristina

I am writing this comment from the Trump Las Vegas Hotel. I bet the Donald would 100% disagree about small wins. He has bet big his entire life, been bankrupt, and now is running a multi-billion dollar enterprise.

-Kristina (@djwaldow’s wife)

Reply
June 28, 2010

LynetteRadio

I'd rather bet small 100x than bet big 1x – maybe that's why I'm a sucker for taking on smaller clients.

Reply
June 28, 2010

PJ Mullen

Singles, walks and reaching base on error is how you set up grand slams. Small steps are as, if not more, important than the big ones.

Reply
June 28, 2010

Christopher S. Penn

Donald's a really, really interesting guy. That said, you know who kicks his butt? Warren Buffett, who goes for small wins, uses the small wins to pay for the big ones, but never, ever forgets the small ones – they're the fuel for experimentation.

Reply
June 29, 2010

DJ Waldow

CP: So I'm pretty sure that was Kristina's first comment on a blog EVER. Love it. I think she had a point, but clearly “the Donald” is an exception.

DJ Waldow
@djwaldow

Reply
June 29, 2010

DJ Waldow

Mr. Penn:

Clearly you make several good points. Hard to argue with this one, “The only way you ever win – big or small – is to garner the favor of luck long enough to win something, and then walk away while you’re still ahead.” Of course luck plays a huge factor. Also, they continue to build casinos in Vegas, so … yeah. The house must be winning – big and often.

However, what I meant by the statement, “you have to play big to win big” is simply this. Yeah, you can continue to bet small and garner small victories. You can add up all of those small wins over your lifetime and they (may) add up to a “big” win.

BUT

It is very difficult to start with $5 and continue to bet$ 5 per hand and win big. That's all. I think it's all about taking a few risks here and there. That being said, I have the discipline to only take $100 out of the ATM. Therefore, I can only lose$ 100. I go into the evening fully expecting to lose $100. It's the price I pay to have a few “free” cocktails and have some fun. Clearly more$ than an evening at the movies of WoW, but, it's a choice.

Now, let's say I start with some (small) $5 bets and in 20 minutes, double my pot to$ 200. I take that $100 profit, jam it in my pocket and play with the house's$ from that point forward. Every so often, I take some of the winnings and stuff them back in my pocket. BUT – if I want to have the opportunity to win big, I have to bet some big piles. Right?

I think this applies to business too. Make smart, calculated bets. Every so often, it's okay to take a bigger risk … for the bigger payoff. BUT you better know the consequences should the bet not pay off.

I think that's all. Writing this 1/2 a cup of coffee in. That's my excuse for it being all over the place.

DJ Waldow
@djwaldow

Reply
June 29, 2010

Whitney Hoffman

This is interesting to me- I also agree with making calculated risks. Convincing my husband to let me sink $1K into Apple stock felt like a big risk to him, a calculated risk to me, and it paid off. Other stock choices (and the stock market is alot like Vegas) have not been big winners; others, like monthly investments in market basket mutual funds work by dollar cost averaging, increasing your “bet” slowly over time, and benefiting or losing in the aggregate.

Consider also the folks who do what I would call “Carribean style” investing. Each week, each person puts $5 into the fund. At set periods, each person gets to withdraw the whole amount of the fund. So 25 people doing this would get a turn, once a year, to have$ 250 dollars all at once. For people that have a problem saving up a bulk payment for an appliance get their turn to get all the money and feel relatively rich, in a way they might not otherwise have the discipline to save that much by putting away $5 each day. If you get an “early” turn, you feel even better, because you get more money sooner than you could have saved it on your own. But this is all about community, turn taking, and sharing at its heart, and that what works as an investment club for many people with very little accumulated cash.

Money is a tool, as are all your other tangible and intangible assets. You can decide to risk principal, or just interest; you have to be able to judge and make informed decisions to win long term.
The only problem with the “win” analogy is that it implies someone else has to lose; good investing means enriching yourself without necessarily harming anyone else in return.

Reply
June 29, 2010

DJ Waldow

CP: So I'm pretty sure that was Kristina's first comment on a blog EVER. Love it. I think she had a point, but clearly “the Donald” is an exception.

DJ Waldow
@djwaldow

Reply
June 29, 2010

DJ Waldow

CP: So I'm pretty sure that was Kristina's first comment on a blog EVER. Love it. I think she had a point, but clearly “the Donald” is an exception.

DJ Waldow
@djwaldow

Reply
June 29, 2010

DJ Waldow

Mr. Penn:

Clearly you make several good points. Hard to argue with this one, “The only way you ever win – big or small – is to garner the favor of luck long enough to win something, and then walk away while you’re still ahead.” Of course luck plays a huge factor. Also, they continue to build casinos in Vegas, so … yeah. The house must be winning – big and often.

However, what I meant by the statement, “you have to play big to win big” is simply this. Yeah, you can continue to bet small and garner small victories. You can add up all of those small wins over your lifetime and they (may) add up to a “big” win.

BUT

It is very difficult to start with $5 and continue to bet$ 5 per hand and win big. That's all. I think it's all about taking a few risks here and there. That being said, I have the discipline to only take $100 out of the ATM. Therefore, I can only lose$ 100. I go into the evening fully expecting to lose $100. It's the price I pay to have a few “free” cocktails and have some fun. Clearly more$ than an evening at the movies of WoW, but, it's a choice.

Now, let's say I start with some (small) $5 bets and in 20 minutes, double my pot to$ 200. I take that $100 profit, jam it in my pocket and play with the house's$ from that point forward. Every so often, I take some of the winnings and stuff them back in my pocket. BUT – if I want to have the opportunity to win big, I have to bet some big piles. Right?

I think this applies to business too. Make smart, calculated bets. Every so often, it's okay to take a bigger risk … for the bigger payoff. BUT you better know the consequences should the bet not pay off.

I think that's all. Writing this 1/2 a cup of coffee in. That's my excuse for it being all over the place.

DJ Waldow
@djwaldow

Reply
June 29, 2010

DJ Waldow

Mr. Penn:

Clearly you make several good points. Hard to argue with this one, “The only way you ever win – big or small – is to garner the favor of luck long enough to win something, and then walk away while you’re still ahead.” Of course luck plays a huge factor. Also, they continue to build casinos in Vegas, so … yeah. The house must be winning – big and often.

However, what I meant by the statement, “you have to play big to win big” is simply this. Yeah, you can continue to bet small and garner small victories. You can add up all of those small wins over your lifetime and they (may) add up to a “big” win.

BUT

It is very difficult to start with $5 and continue to bet$ 5 per hand and win big. That's all. I think it's all about taking a few risks here and there. That being said, I have the discipline to only take $100 out of the ATM. Therefore, I can only lose$ 100. I go into the evening fully expecting to lose $100. It's the price I pay to have a few “free” cocktails and have some fun. Clearly more$ than an evening at the movies of WoW, but, it's a choice.

Now, let's say I start with some (small) $5 bets and in 20 minutes, double my pot to$ 200. I take that $100 profit, jam it in my pocket and play with the house's$ from that point forward. Every so often, I take some of the winnings and stuff them back in my pocket. BUT – if I want to have the opportunity to win big, I have to bet some big piles. Right?

I think this applies to business too. Make smart, calculated bets. Every so often, it's okay to take a bigger risk … for the bigger payoff. BUT you better know the consequences should the bet not pay off.

I think that's all. Writing this 1/2 a cup of coffee in. That's my excuse for it being all over the place.

DJ Waldow
@djwaldow

Reply
June 29, 2010

Dave Folkens

I think the different approaches both have validity when you're talking about gambling approaches. I know some folks that have applied the bet big/win big strategy and done quite well but I also think that steady progress works if your intent is not to get rich but perhaps enjoy a night out.

In the case of business application, I tend to again value a blended strategy that actually can parallel playing at the tables. I really like the Warren Buffet reference below as in a business setting you can't always risk everything because you'll burn bridges, run out of cash, and risk the careers of your employees. However, I think the strategy that positions you well for growth is taking care of your business and get those little wins. Build up a stack of chips (so to speak) and stick with your approach that works. Then, when you're having one of those days when fortune smiles on you and things are coming together (again, in business or gambling) you'll have the resources to take your shot. The key is having the sense to know when you're ready to make that leap and take your chances on the big move.

There will inherently be risk anytime you take a chance but if you know what your goals are and where you want to go, I think you can position yourself patiently until you see the time to make that big bet.

-Dave
@dfolkens

Reply
June 29, 2010

Dave Folkens

I think the different approaches both have validity when you're talking about gambling approaches. I know some folks that have applied the bet big/win big strategy and done quite well but I also think that steady progress works if your intent is not to get rich but perhaps enjoy a night out.

In the case of business application, I tend to again value a blended strategy that actually can parallel playing at the tables. I really like the Warren Buffet reference below as in a business setting you can't always risk everything because you'll burn bridges, run out of cash, and risk the careers of your employees. However, I think the strategy that positions you well for growth is taking care of your business and get those little wins. Build up a stack of chips (so to speak) and stick with your approach that works. Then, when you're having one of those days when fortune smiles on you and things are coming together (again, in business or gambling) you'll have the resources to take your shot. The key is having the sense to know when you're ready to make that leap and take your chances on the big move.

There will inherently be risk anytime you take a chance but if you know what your goals are and where you want to go, I think you can position yourself patiently until you see the time to make that big bet.

-Dave
@dfolkens

Reply
June 29, 2010

Whitney Hoffman

This is interesting to me- I also agree with making calculated risks. Convincing my husband to let me sink $1K into Apple stock felt like a big risk to him, a calculated risk to me, and it paid off. Other stock choices (and the stock market is alot like Vegas) have not been big winners; others, like monthly investments in market basket mutual funds work by dollar cost averaging, increasing your “bet” slowly over time, and benefiting or losing in the aggregate.

Consider also the folks who do what I would call “Carribean style” investing. Each week, each person puts $5 into the fund. At set periods, each person gets to withdraw the whole amount of the fund. So 25 people doing this would get a turn, once a year, to have$ 250 dollars all at once. For people that have a problem saving up a bulk payment for an appliance get their turn to get all the money and feel relatively rich, in a way they might not otherwise have the discipline to save that much by putting away $5 each day. If you get an “early” turn, you feel even better, because you get more money sooner than you could have saved it on your own. But this is all about community, turn taking, and sharing at its heart, and that what works as an investment club for many people with very little accumulated cash.

Money is a tool, as are all your other tangible and intangible assets. You can decide to risk principal, or just interest; you have to be able to judge and make informed decisions to win long term.
The only problem with the “win” analogy is that it implies someone else has to lose; good investing means enriching yourself without necessarily harming anyone else in return.

Reply
June 29, 2010

Whitney Hoffman

This is interesting to me- I also agree with making calculated risks. Convincing my husband to let me sink $1K into Apple stock felt like a big risk to him, a calculated risk to me, and it paid off. Other stock choices (and the stock market is alot like Vegas) have not been big winners; others, like monthly investments in market basket mutual funds work by dollar cost averaging, increasing your “bet” slowly over time, and benefiting or losing in the aggregate.

Consider also the folks who do what I would call “Carribean style” investing. Each week, each person puts $5 into the fund. At set periods, each person gets to withdraw the whole amount of the fund. So 25 people doing this would get a turn, once a year, to have$ 250 dollars all at once. For people that have a problem saving up a bulk payment for an appliance get their turn to get all the money and feel relatively rich, in a way they might not otherwise have the discipline to save that much by putting away $5 each day. If you get an “early” turn, you feel even better, because you get more money sooner than you could have saved it on your own. But this is all about community, turn taking, and sharing at its heart, and that what works as an investment club for many people with very little accumulated cash.

Money is a tool, as are all your other tangible and intangible assets. You can decide to risk principal, or just interest; you have to be able to judge and make informed decisions to win long term.
The only problem with the “win” analogy is that it implies someone else has to lose; good investing means enriching yourself without necessarily harming anyone else in return.

Reply