I have two distinct lives. One in the trenches of low-budget film and television, the other in professional gambling. Because of the feast-or-famine nature of show business I need a reliable income... gambling. So here you will read about both worlds. Enjoy!

Thursday, August 25, 2022

Gambling With an Edge - Bob Hamman

 Our guest this week is legendary bridge player Bob Hamman.  Bob also runs a company called SCA that basically insures large unlikely events.  One example would be the Pepsi promotion where someone could win a billion dollars.

We welcome your questions - send them to us at, or you can find me at @RWM21 on Twitter or
Click to listen - Alt click to download

Show Notes

[00:00]  Introduction bridge player and businessman, Bob Hamman
[00:30]  Bob's background in bridge
[01:43]  The Italian Blue Team
[03:42]  Bobby Wolff
[04:16]  What other games did Bob play?
[05:27]  Playing in major tournaments with various partners
[06:54]  Maintaining skill and alertness at an advanced age
[08:15]  Getting paid to play as a partner
[09:10]  The Dallas Aces
[12:09]  Does Bob still study bridge, review hands?
[12:43]  Online bridge, cheating
[18:24]  SCA, a company that insures unique promotions
[21:00]  Lance Armstrong promotion
[22:54]  Founding SCA
[24:14]  The Promise
[25:47]  Memorable contract negotiations
[28:26]  Kelly criterion
[29:24]  Pepsi $1B promotion
[30:58]  Illegal and/or immoral promotions
[31:45]  The most unusual thing that SCA has insured
[35:36]  Fraudulent winners
[40:06]  Do SCA representatives attend events?
[43:45]  Does SCA help to develop promotions?
[45:45]  Bridge as a game of skill, variance in games and promotions
[51:25]  Contacting SCA
[52:04]  Recommended:  The Sicilian Ristorante, Patrick Veitch on YouTube

Sponsored Links:

Guest Links:

The Sicilian Ristorante -
Patrick Veitch on YouTube -

Thursday, August 18, 2022

Gambling With an Edge - guest Shane Sigsbee

 Our guest this week is Shane Sigsbee.  Shane started a company called "I am a Whale" that backed professional poker players, and then moved into sports arbitrage, and getting down for other pros.

We welcome your questions - send them to us at, or you can find me at @RWM21 on Twitter or
Click to listen - Alt click to download

Show Notes

[00:00]  Introduction of sports better Shane Sigsbee
[00:30]  Shane's background in golf
[01:20]  Betting on golf
[01:56]  Does being a skilled golfer help Shane handicap golf?
[03:07]  Betting on golf
[05:19]  Billy Walters
[06:45]  Transitioning from financing to gambling, backing poker players
[11:47]  Pricing staking deals,
[16:01]  Finding winning players, backing low stakes
[17:28]  Getting stiffed by winning players
[20:10]  Player contracts
[21:55]  Transitioning into sports, moving to Las Vegas
[25:40]  Getting action down without getting limited
[31:10]  Arbitrage, line manipulation, off-shore outs
[33:56]  Betting for clients, beards
[34:47]  Client characteristics
[36:29]  What sports does Shane bet on?
[37:37]  Company size and structure
[38:23]  Super Bowl props
[39:31]  In-game and half-time bets
[40:29]  Buying real estate, Airbnb
[45:01]  Diversification, real estate business
[51:21]  Networking
[52:17]  Bet Bash

Sponsored Links:

Guest Links:

Thursday, August 11, 2022

Gambling With an Edge - mail bag 8/11/2022

 No guest this week as we answer questions from our mail bag. 

 We welcome your questions - send them to us at, or you can find me at @RWM21 on Twitter or

click to listen - alt click to download

Show Notes

[00:00]  Introduction

[00:30]  Bill Benter's published material

[02:02]  Risk of ruin for 8/5 and 8/6 Jack or Better

[03:47]  Getting flat-bet at a Strip casino

[05:06]  Intermittent fasting

[17:00]  Getting cut off from comps at a small locals casino

[19:39]  Backed off aggressively for counting at a Native American casino

[22:26]  Relationship between net worth and bankroll

[26:55]  Gambling advice, blackjack on Vice




[33:05]  Average daily theoretical calculations across properties

[34:18]  Dating tips for a single professional gambler

[37:11]  Speed of shuffling on video poker games

[38:20]  Paying off markers with a credit card

[40:05]  Video poker training software, Win Poker

[41:43]  Does a property care about the use of video poker strategy cards

[43:01]  Calculating the edge on a video poker loss rebate

[49:11]  Video poker progressives

[50:57]  Recommended:  The Bear on Hulu, Official Secrets on Netflix

Sponsored Links:

Sites Referenced:

Vice episode

Bill Benter's 1994 paper:

Bloomberg article:


"The Bear"

"Official Secrets"

Thursday, August 4, 2022

Our guest this week is tax expert Russell Fox on to talk about tax stuff for gamblers.  He provided updates for the latest edition of Tax Help For Gamblers

We welcome your questions - send them to us at, or you can find me at @RWM21 on Twitter or

Click to listen. Alt click to download

Show Notes

[00:00]  Introduction of Russel Fox from Clayton Tax Services

[00:37]  Tax implications of sports betting in different states

[03:14]  Splitting a large DFS jackpot

[04:17]  Reporting recreational horse player income

[07:40]  Shared sports betting at online sites

[08:47]  FBAR

[11:13]  Crypto and FBAR

[12:15]  RV expenses

[14:46]  Paypal reporting transactions, 1099-K

[17:08]  Group slot pulls

[20:03]  W-2 G from a Native American casino

[23:23]  Gambling partnerships

[25:22]  Cherokee North Carolina winnings




[29:21]  Withholding SSN on W-2 G

[31:40]  Tax liability for WSOP Main Event

[34:54]  Deducting gambling losses

[36:29]  Filing as a professional for part of the year

[37:15]  S-corp for professional gamblers

[42:12]  Frequently overlooked tax deductions

[43:15]  Constructive receipt

[45:00]  Taxes and beard accounts

[49:56]  Recommended:  Blood and Treasure by Bob Drury and Tom Clavin, Something Missing by Matthew Dicks, For Good and Evil by Charles Adams

Sponsored Links:

Guest Links:

Tax Help For Gamblers -


Blood and Treasure by Bob Drury and Tom Clavin -

Something Missing by Matthew Dicks -

For Good and Evil by Charles Adams -