Molly's Game 未删减版:黑帮威胁、FBI突袭与1亿美元赌池……最后仍然赢了
Molly Bloom × Chamath Palihapitiya × Jason Calacanis × David Sacks × David Friedberg
Molly Bloom 靠出售信任、通行权与归属感,打造了一个高风险生意,而不是靠发牌。 23岁那年,她仅一个晚上端酒就拿到4,000美元小费,并接触到名人、金融家、政客和科技领袖;8个月后,她创办自己的牌局,把买入额从10,000美元提高到50,000美元。作为不打牌的人,她看出“这不只是扑克”——真正的产品是社群、故事、逃避现实和幻想。
纽约牌局像一家私人交易所,流动性取决于 Bloom 亲自充当银行。 她清退职业牌手,承诺“全是行动”,让玩家坐在偶像或潜在商业伙伴身边;买入额达到250,000美元,一局桌面上大约有1,000万美元,最终有一名玩家输掉1亿美元。她理想的终局,是9名风格相近的玩家制造戏剧性的短期结果,而在一年时间里,“钱不断易手,庄家最终赢钱”。
资产负债表上最大的风险不是名义净资产,而是交易对手的行为。 Bloom 发现,即便是富人,在亏损触发恐惧和失控感后,也可能变得不理性;她的工作是控制住自己,让对方感到安全,并管理结算。一名嘉宾说,自己曾被一个完全付得起钱的人赖掉250,000美元,只能亲自垫付;Bloom 警告说:“如果有人赖掉牌局欠款,你可能永久性地毁掉这场牌局。”
洛杉矶的控制权争端是早期治理破裂;后来,Bloom 自己的漂移摧毁了这门生意。 Bloom 说,一名未具名的玩家变得痴迷,想做一些让她觉得不对的事——包括主动作弊——还抱怨她赚得太多;他提出让她留下,担任领工资的傀儡。主持人猜测那个人是 Tobey Maguire,Bloom 只说其身份“外界已经有充分猜测”。她拒绝了,并于2008年在纽约重建牌局。后来,贪婪和不断扩大的授信敞口,让她在原则左右一步步做出“细小的决定”,最终在律师反对的情况下,连续6个月非法抽水。
尾部风险同时来自有组织犯罪的胁迫和政府执法。 自称代表、或冒充代表意大利黑手党的人要求分成;随后,一名袭击者把枪塞进 Bloom 嘴里,殴打她、抢劫她、威胁她的家人,并说控制权“已经不再由你决定”;3或4天后,125名与黑帮有关人员被捕的消息传出,这些人也随之消失。之后,FBI 渗透进牌局,民事资产没收掏空了她的账户;重建2年后,17名持枪特工将她逮捕。
当检方提出以金钱和自由换取合作时,Bloom 选择了声誉上的偿付能力,而不是财务上的获救。 南区检方提出,只要她提供涉及亿万富翁、政客和名人的线索,就归还全部财产并暂缓起诉;她大约有48小时考虑,最终拒绝了,理由是:“这是我的错。” 品格证词帮助她免于入狱,但35岁时,她仍是一名背负数百万美元债务的重罪犯。
她的复苏把一本大约只有10人读过的书,变成了一张押注声誉与偿债能力的非对称期权。 Bloom 当时和母亲住在一起、债台高筑,却仍然锲而不舍地追逐 Aaron Sorkin;他的评价是:“我从没见过一个人,运气如此糟糕,却又如此自负。”随后他向她发出了邀约。她还拒绝了一笔六位数或七位数的名人抹黑稿,并说自己终于在“去年夏天”还清了政府的债。
成熟后的风险框架,把勇气、强迫冲动和真正承受不确定性的能力区分开来。 她如今会“挑选自己的战场”,把能够控制自己的竞争者,与那些乘坐“失控的享乐跑步机”驶上“自毁快车”的人区分开来。她的商业经验同样关乎行为:练习完整倾听和艰难共情,因为未经训练的大脑会把不确定性视为“代谢上不可持续的状态”,不断搜寻一个可以抓住的主观真相。
1. Bloom 真正出售的是高信任通行权,而不是扑克
Bloom 的入场纯属偶然:一次受伤终结了她进军美国滑雪队的计划后,她搬到温暖的洛杉矶,在雇主的扑克局里端酒。牌桌上有一线名人、一家大型投行的掌门人、家喻户晓的政客和一名科技界人士;4,000美元小费让她看到了这门生意的经济价值,也看到了“获取信息、资本和权力的通行权”。
在8个月里,她学会扑克的语言,建立联盟,并记录自己会改变什么。她把牌局视为进入原本无法接触的社群的“特洛伊木马”;恰恰因为自己不打牌,她看出真正的产品是归属感和幻想。24岁时,她营造出蒙特卡洛或 James Bond 式的氛围,把买入额从10,000美元提高到50,000美元,并让洛杉矶牌局持续了大约5年。
早期护城河是关系资本。在母亲“诚信、诚信、诚信”的指引下,Bloom 拒绝职业牌手提出的、以直接现金换取参局资格的交易,也避免把有权势的人当成一笔笔交易,并在扑克之外经营关系。她运营时思考的问题不是“你能为我做什么”,而是“我能为你做什么”。
2. 纽约的扩张来自修复信任,同时承受信用风险
洛杉矶的决裂始于一名未具名的玩家变得痴迷,想做一些让 Bloom 觉得不对的事——包括主动作弊——还抱怨 Bloom 赚得太多,随后提出让她留下,担任领工资的傀儡。Bloom 拒绝了;他说玩家更喜欢电影明星的牌局。她只称其身份“外界已经有充分猜测”,主持人则给出了 Tobey Maguire 的名字。一个细节颇能说明问题:一台17,000美元的 Shuffle Master 曾以每次使用200美元的价格借给她,直到她买下一台。
Bloom 于是愤然于2008年搬到纽约,并采访玩家,了解现有牌局的情况。他们抱怨的是信任:牌局组织者有时也会下场,而一个糟糕的晚上可能意味着更高的抽水。她的答案是不抽水、排除职业牌手、提供行动和有价值的近距离社交,并亲自充当银行,结算每一笔输赢。
规模极其惊人:买入额250,000美元,桌面上约有1,000万美元,同时背景里播放着总统的经济讲话。Bloom 说,一名参与者最终输掉了1亿美元。她理想中的牌桌由9名打法和水平相近的玩家组成,在一年时间里制造令人心跳加速的结果,同时让资金不断易手,庄家最终赢钱。
次日结算让承保成为生死问题。Bloom 观察到,即使从净资产看,亏损金额完全不值一提,亏损仍会触发恐惧;如果她也跟着拖欠者陷入恐慌,牌局可能崩盘。她选择控制住自己,安抚并说服玩家。一名嘉宾另行表示,自己曾亲自替一个完全付得起钱的人垫付250,000美元的赖账。Bloom 还说,她的工资名单上有银行员工,因为兰博基尼和租来的圣费尔南多谷房屋,证明不了什么。
3. 外部胁迫暴露了 Bloom 内在漂移的代价
一些来自 Brighton Beach 的玩家通过了 Bloom 的审核,尽管她觉得“有些不对劲”;后来她得知,这些人经营着她所谓的纽约市最大保险诈骗案,并据称与俄罗斯黑帮有关。随后,自称代表、或冒充代表意大利黑手党的人要求从她的牌局分一杯羹。她拒绝了,但他们并没有离开。
一名袭击者闯入她的公寓,把枪塞进她嘴里,殴打她,威胁她在科罗拉多州的家人,并搬空了保险箱:里面有现金、金条,以及她祖母留下的纪念品。Bloom 因恐惧和羞耻没有告诉任何人。沉默了3或4天后,《纽约时报》报道了一起大规模黑帮抓捕行动,共有125人被捕;她此后再也没有听到那些勒索者的消息。
活过这场威胁,并没有让她恢复判断力。Bloom 形容,贪婪通过一个个让她略微偏离价值观的“细小决定”接管了局面:她对放玩家入局变得更加宽松,扩大了自身敞口;在一些实际上押注于坏信用的牌局里,她开始从底池抽钱。尽管律师告诉她不要抽水,她还是这么做了,持续了最后6个月。
联邦探员监听俄罗斯人的电话后,安插了一名线人。一名荷官最终发短信说:“别来这里。FBI 正在找你。” Jason 将民事资产没收解释为:财产不像人一样享有无罪推定,所以可以被全部拿走。重建2年后,洛杉矶新据点刚开5天,17名持枪 FBI 特工逮捕并铐住了她;她身无分文,只剩一天半时间赶往纽约。
4. 承担责任,保住了后来得以变现的声誉
无力负担辩护费用后,Bloom 找到一名她认为正直的律师,并接受认罪协商。她说,南区检察官对俄罗斯人或意大利人并不太感兴趣,他们更想要亿万富翁、政客、名人的线索,以及被偷听到的商业交易。她还明确强调了一点:“我的牌局里没有 Epstein。”
检察官提出,只要她合作,就归还她的钱并给予暂缓起诉。大约48小时后,Bloom 拒绝了:她对法律拥有“近乎完美的信息”,有忠诚的客户,也有很多机会,但她选择亲自承担抽水这项决定。为了逃避自己的选择,把玩家及其家人拖进调查,不是她愿意一辈子背负的事情。
尽管所有人都预计她会入狱,法官考虑了 Bloom 过去的人生,以及教授和滑雪教练写来的品格证明。他判处高额经济处罚,但没有监禁。尽管如此,35岁的她仍背负数百万美元债务,是一名重罪犯,也成了她认为过于简化的通俗小报叙事的主角;她剩下的资产,就是自己的故事。
她的书或许只有10个人读过,但 Bloom 仍不断追逐最优秀的电影人,并通过锲而不舍的联系拿下 Aaron Sorkin。Jason 质疑出版是否等于背叛那些让她走上这条路的人;Bloom 回应说,她只点名那些谈论过参局的人,拒绝了一篇六位数或七位数的名人抹黑稿,并选择了一名愿意在合同中承诺“不毁掉任何人的人生”的编剧。她在去年夏天还清了政府的债。
5. 事后复盘区分了有用的波动与成瘾
Bloom 将自己的风险偏好归因于一个竞争极其激烈的家庭,以及一位教会她不能让恐惧阻挡自己的父亲。如今她不再需要肾上腺素冲击,尤其是在成为母亲之后,但仍然说:“我永远会选择勇气,而不是舒适。”区别在于选择:“我现在会挑选自己的战场。”
她将扑克室里的人分成3类:把毒品、婚姻破裂和“失控的享乐跑步机”结合在一起的自毁型玩家;偏好波动但仍能保持控制的高度竞争者;以及被牌局中的心理博弈、同袍情谊和基于有限信息做出高水平决策所吸引的人。她认为 Tobey Maguire 是最强的名人牌手,Ben Affleck 排名第二,但补充说,Affleck 的表现取决于“他处在人生的哪个阶段”。
Bloom 的销售框架“情感存在感”,从人们对孤立、无价值感和被剥削的恐惧反向推导。她建议,不要带着简历、金句和推销话术进入关系,而要塑造自己的情绪印记:倾听时不要同时构思回答,提出开放式问题,把温暖与真实结合起来,并对那些观点或性格令人难以相处的人练习“艰难共情”。
她对决策的最后一条警告是:人类厌恶不确定性。如果不刻意训练心智,大脑就会把不确定性等同于恐惧,继而“搜寻某种主观真相”,并紧抓住控制感的幻觉。放松地面对不确定性,会带来好奇心、松动先验判断,也会让适应和变化显得有趣,而不再构成威胁。
Hey everybody, the besties are taking Thanksgiving off. But hey, we didn't forget about you. We banked a couple of great content segments while we were in Vegas. First, here's an interview with Molly Bloom. You know, she ran the legendary highstakes game in LA in New York. I was invited to the LA one. We'll get into that. And her story was turned into the feature film and book Molly's Game. We have a great conversation, tons of insider stories, who imploded in her LA game, the best celebrity poker players, getting shaken down by the mob, how she got an Aaron Sorcin meeting, and much, much more. Big thank you to our friends at Oracle for partnering with us on this amazing VIP lunch we did in Vegas at the Venetian. What a great hotel. Also, make sure you head over to our YouTube channel. A YouTube exclusive for the first ever bestie poker freeze out game. Who's going to win? Chbahhat Freebert, me, or some of the world's greatest poker players, Alan Keading and Jason [ __ ] Also, Phil Helmouth. He he wound up there as well somehow. So, happy Thanksgiving. We love you and uh be safe and we'll see you all next week for a regular episode.
Listen, we have a guest.
We do have a guest. She’s an entrepreneur, bestselling author, and one of Fortune magazine’s most powerful women.
I didn’t know that.
Molly Bloom ran the world’s most exclusive poker game. You probably know her from the movie Molly’s Game, which we’ll hear a little bit about today. Molly’s also got an amazing sense of what made her successful, and the journey she’s been through is a really interesting one to learn from. Please join me in welcoming Molly.
Thank you. All right, nice to see you, Molly. What was the origin of the game? We know some of our friends played in it.
Jason, you claimed on our show—let me just read the notes.
The notes?
Yeah, there are notes here. Apparently, we were on the show and Jason said he played in the game all the time.
No, no, no. I was invited to the game.
No, you did not say that. Lisa, please pull the tape, and when you’re ready, just raise your hand and let me know exactly what Jason said. Molly responded on Twitter that you did not play in her game.
Okay, let’s be clear. Molly, did you invite me to the game?
I don’t remember inviting you to the game, but here’s the deal: There were 2 versions of the game. There was the version where I was working for someone who would send me a list.
Got it. And I’m sure that you were probably on that list when I—
Jeffrey Epstein’s list, right? He was young.
Absolutely.
Okay.
But when it was my game—
I just remember the Four Seasons. Was that your game?
Okay, so it was the Four Seasons. I remember you invited me and said, “Tobey’s going to be there, Leo’s going to be there,” whatever, and they’d love to see you. I said, “They would love to see me lose $50,000. There’s no way I’m going to this game,” because I was playing in a 5/10 game.
But you were working for somebody at the Viper Room. The game started, you then took it over, and it very quickly became a big game. Famously, Tobey Maguire, a friend of ours whom we sometimes play poker with, was part of this. Then you decided to move it to New York. Just let everybody know how this all got started for you and when you took over the game.
I was in college, training for the U.S. Ski Team, and had an accident and retired. I kind of didn’t know who I was because sports were my identity. I went to L.A. simply because I wanted to be warm. I’d been cold since I was 2 years old.
I ended up working for this guy. He had a real estate development company, and he said, “Tomorrow night, I need you to serve drinks at my poker game.”
So I showed up to this poker game, and it was A-list celebrities, like you’ve mentioned, but also the head of one of the biggest investment banks, a politician who was a household name, somebody from the tech world. I got to be a fly on the wall in this incredibly compelling room. I was 23 years old, and this was access to information, capital, and power.
At the end of the night, they were tipping me in chips, and someone counted out $4,000 in cash. I was like, “Okay, I don’t know what’s up with this chip-token economy, but I think I might want in.”
Over the next 8 months, I started to learn to speak the language of poker. What I was really focused on was, how do I forge alliances? About 3 months in, I knew I didn’t want to just serve drinks. I knew I wanted to have my own games. This was an incredible opportunity. It really was a Trojan horse—you could use it to infiltrate any subset of society.
I was learning about the world from some of the people who were actively involved in shaping culture. It was a fascinating and interesting time, and it was also very lucrative. I decided to start my own games, and I had 8 months of notes on what I would do differently.
I think because I wasn’t a poker player, there was an advantage. I was able to zoom out and see that this isn’t just about poker. This is about community, storytelling, belonging to something, escapism, and fantasy. I wanted everyone to come into this room and, from the second they walked in, feel like they were in Monaco or in a James Bond movie.
When I started the game 8 months later, I was 24 years old. I didn’t think these people who were rich and famous were going to come, let alone make it their home game. I would say that started the 4.5- to 5-year tenure of the L.A. game.
When we started out, when I was serving drinks, it was a $10,000 buy-in. I raised it to a $50,000 buy-in.
That’s the number I remember. I was like, “Wow, those are high stakes,” because at the time, even in L.A., people were not playing for those stakes. You really elevated the game.
Somehow the mob got involved, and the game moved to New York. Fast-forward through this, because it got pretty dark pretty quickly.
It did. I lost the game in L.A.
How do you lose the game in L.A.?
One of the players, who was making 10 times what he was making in the poker game, became very obsessed with the game. He wanted to talk about it all the time and started wanting to do things that felt wrong.
Like maybe target certain weak players, maybe get some of your tip money—
Like actively cheat the game.
Angle-shoot the game.
Angle-shoot. He was also complaining that I made too much money.
He basically gave me this offer: “I’ll pay you a salary, and you can work for me. You can be the figurehead.”
I really wanted to keep the game. I was making millions of dollars legally. I was paying my taxes. As I had mentioned, it was incredibly exciting and educational. But I didn’t want to work for him.
Right. There’s a power imbalance because this person theoretically might have been famous, and the players might follow him if he boxed you out.
He said, “It turns out they want to play at a movie star’s house.”
They wanted to what?
Play at a movie star’s house.
Got it. Is it well known who that person is?
It’s well speculated.
She never says who.
Who they speculated?
Tobey Maguire.
Uh-huh.
The concept was also that there was this device called a Shuffle Master, which was used in the first iteration. It makes the game go much faster. 3 people—myself, Tobey, and another person—had a Shuffle Master in Los Angeles because you could theoretically buy them from somebody in Vegas, but they weren’t available.
Chamath remembers because he got an early one, and I used to bring mine to Chamath’s game. He’d say, “Hey, can you bring the Shuffle Master?”
He also angle-shot you and wanted you to rent a Shuffle Master.
I’ll never forget going to his house.
No, he was talking about Tobey, not me.
Not you. Not you.
I’ll never forget. He was right about the Shuffle Master.
Renting out a Shuffle Master. I mean, he had a tough couple of years. You said it was a pretty big downdraft.
Shuffle Masters cost $17,000 at the time. Yeah. Um, and he was right that we needed one. Uh, and so he said, “Well, how about we'll use mine? Just come up to my house and get it, right?” So, go to his house and get it. And then I brought it back and he said, “Um, I'm going to need $200 for this.” I'm like, “You're you're kidding, right?” Like, I'm sitting there looking at his mansion, you know, 200 a shot. I mean, and about 5 months in, I'm like, “We need to buy our own shuffle master, right?”
Yeah, they could be obtained. So, Tobey took the game away from you, and you were like, “I’m moving to New York and restarting the game there.”
I was really pissed.
It was 2008.
Yeah, I was like, “I’m going to build the biggest poker game in the world.”
Can you talk a little bit about how you did that, with respect to salesmanship and building confidence to grow that game? You moved to a new city and didn’t know anyone.
How do you convince them, and maybe talk a little bit about what you learned early on about sales and earning people’s trust and how you got that to happen?
Yeah. So what I focused on much earlier, before I eventually realized that if you’re treating the business—if you’re treating the poker game like a business—essentially, what you want is 9 people seated around a table with equal playing styles, equal skill levels, and hopefully you get these heart-pumping results. But at the end of the year, the money changes hands and the house wins.
But before I realized that, what I had was—I was raised by parents who believed in teaching lessons all the time. My dad’s lessons were excellence and discipline and overcoming fear. My mom’s were integrity, integrity, integrity; what can you do for the world? And don’t make people feel like they’re transactions.
That’s the education that I had. I was a really hard worker, and I held myself to a high standard. For instance, when I started running these games, there were a lot of pros who would offer me freerolls—straight cash if they could play—but I knew that would compromise the integrity of the game.
So what I did was, I didn’t take shortcuts. I was trustworthy, I invested in people, and I developed relationships. I was very intentional about not asking them for favors before I walked in, because everyone in the world was asking them for favors. Instead of “What can you do for me?” it was, “What can I do for you?”
Over time, I think people sense that you’re a trustworthy person and that you’re deeply invested in their outcome. I think that was focusing on that relational capital, cultivating that trust, and being a part of someone’s life—doing events, expanding the time that you spend together outside of just poker, and doing events with the whole crew.
That’s what I focused on, and it was so incredibly valuable.
A big part of this culture at the time, unlike, say, some other games where we have a group of friends and it’s a high-trust environment and we settle up yearly, was that the tradition in L.A., at least in the ones I played in, was you settled up the next day. That would be your responsibility, I assume, or one of your runners, to go collect checks and settle with people.
Sometimes people maybe couldn’t settle, and it could get a little bit awkward. So maybe you could tell us about that part of the job that people don’t see, which is, hey, you’ve got to go the next day. Somebody lost $50,000 or $250,000. What was the biggest loss that you had to go collect? What was that like?
A couple things. First of all, what shocked me was that if you looked at the net worth of a lot of these people who were playing, it would indicate that a loss of a couple hundred thousand or even $1 million wasn’t a big deal, right? But that wasn’t the case. I saw crazy behavior.
I always asked myself the question, “What’s underneath this? What’s causing this flipping of the table, screaming at me that you’re never going to pay, whatever?” What I got to was that it’s fear. Even though it doesn’t make logical sense compared to someone’s net worth, losing money, or losing in general, triggers this fear response. You feel out of control.
My job consistently was having enough top-down control to be the one who could then make that person feel safe, because I saw in other games that the game runner was on the hook for the money. This person is saying, “I’m never going to pay you.” Then they’re both in fear, they get into a sparring match, the games end, and things fall apart.
It was really useful for me to be able to emotionally regulate myself, understand what was going on, talk them down from a ledge, and get them to pay, because if somebody stiffs the game, you could break the game permanently.
Well, I’ve been stiffed, and I wrote those checks.
Really? What’s the biggest you got stiffed for?
$250,000.
$250,000. And the person could afford to pay it?
For sure.
And they stiffed you, and then you’ve got to come out of pocket for that and make good.
Yeah.
Yeah. That’s hard.
Yeah, but it teaches you to do a really good job on the vetting.
Yes. I mean, I had bank employees on my payroll, basically, because in L.A. people drive a Lamborghini, they rent a house in the Valley, right?
Yeah. So, Molly, can you just talk about what you talked about earlier with us when we were playing poker or during lunch? Someone said, “What sort of stuff are you into?”
Yeah. And I said, “I’m really into adrenaline stuff, like adrenaline sports.” I’m a competitive skier and so on. But this feels like that sort of high-stakes environment that you put yourself in. Where did that come from? And do you think you selected yourself into this environment because it feels like heli-skiing?
I think, first of all, I come from a really competitive family. One brother went to the Olympics twice and was a world champion in mogul skiing at 16. Then, after the Turin Olympics, he got drafted in the 5th round of the Philadelphia Eagles. He was an Abercrombie model, then he started and sold a tech company at literally the highest valuation, down to the second, I think. And now he’s CEO of the X Games.
My other brother is a Harvard-educated cardiothoracic surgeon at Mass General.
Which one do your parents love most?
Well, they loved them more, but then Kevin Costner played my dad in the movie, so I instantly became the favorite kid.
So they eventually loved you.
Eventually, but it took a lot.
It did. Yeah.
That was part of it. We grew up skiing, and my dad was really insistent that fear was not going to sideline you. From an early age, some kids get grounded for talking back or whatever. We got in trouble for letting fear get in the way.
Something started to happen in those early years where it was this very exciting experience to look at something, be afraid of it, and then do it—like running a big game where people go south for $250,000 and then you decide, hey, I’m going to do it. But that was the behavior you were trained on early on. I think it was a byproduct of looking fear in the face and jumping into it.
Yeah. And that’s a pretty great feeling, right?
Totally, and a bit of pride. You wanted to restart the game, and so you had that pride.
Big-time pride. So take us to the game moving to New York, the mob getting involved, you getting beat up, getting pinched, and this whole thing going sideways.
Okay. So I moved to New York. To your question, I really started interviewing poker players: What was the problem with the current system? There were really well-established games and whatever, and what I found was that there was a problem with trust.
A lot of times, game runners would play in their own games. If they had a bad night, the rake would be higher. I wasn’t taking a rake. Then I realized, okay, well, if I can become the bank for these games and settle, and then provide this experience in which you could sit down next to your hero, or sit next to somebody who’s going to change your life in business, and there are no pros and it’s all action, this is how I’m going to do it.
So I became the bank for these games. The game in New York was a $250,000 buy-in. It was 2008, and I remember the first game: the president was in the background on the television, giving the State of the Union on the economy, and there was $10 million on the table.
These were insane games. They were playing insane variations of poker.
And you love the thrill. You feel the thrill.
I did. Yeah. I mean, this was the game where, ultimately, someone lost $100 million. So, yeah, that definitely made noise.
I told my parents, “Listen,” because they were like, “Please go back to school. Please finish your degree.” I knew what I was doing. I was like, “Okay, but I just have to do this thing real fast.”
So I decided I was going to go as big as I possibly could. Then I started smaller games, and it got out of control. Some of these guys from Brighton Beach started playing. I had them vetted, and their stories checked out, but I knew something was off. It was really off.
They were running the biggest insurance-fraud scheme in New York City history. They had alleged ties to the Russian mob. My only involvement with them was that they played in my poker game.
The next thing that happened was that the Italian mob—or impersonators of the Italian mob—came to me and said, “We want a piece of your game,” and I turned them down. They didn’t just go away. They sent someone to my apartment. This guy broke into my apartment, put a gun in my mouth, and—
Jesus.
He told me that I worked for them and that, if I told anyone—law enforcement or anybody—they had found out where my family lived in Colorado. Then he beat the hell out of me and forced me to take everything out of my safe.
There was money and a gold bar in there for some reason, but also things that my grandmother, whom I was named after, had left for me.
It was just terrifying. I was completely terrified and ashamed of what I was now implicating my family in. I couldn't call anyone.
Wow.
I kept waiting for their call.
Did you think at that moment, “You know what? Okay, done”?
Yeah, but I didn't know if it was an option anymore because they were looking at me as a big earner now. They said, “This is a warning. It's not up to you anymore.”
Wow.
So I didn't know what to do.
Could you confide in anyone?
I didn't tell a single soul.
You didn't tell anyone? You kept that all in?
Yeah. I was in my apartment, and I couldn't go outside because it was very clear I'd been assaulted. I was confused as to why I wasn't hearing from them, because about 3 or 4 days went by and I didn't hear anything. Then I got The New York Times, and on the cover it said, “125 arrested in the biggest mob-related takedown in New York City history.” I never heard from them again.
Wow. Dodging a bullet. My God.
Oh my God. But, yeah, but then—
Oh my gosh. Then the bullet of me came into play, and I started getting out of control. Like I said, integrity was important to me, but over time I was making these little decisions that were just a little left or right of where I stood. Greed and money became everything, and I started doing things that my attorneys told me not to do.
Raking the game.
Yeah. Taking a rake.
Taking a rake. Now, for people who don't know, if you have a home game and you collect tips, it's kind of a gray zone, but generally speaking, people don't have a problem with it legally. But in the casino business, the legal gaming business, they feel that's their business: to take a rake. They went through the proper channels to get a license to do that, and you can't do that at a home game, right? So now you're breaking the law to make extra money.
Sorry, just to be clear, a rake just means when you put money in the pot, they take a little bit of it out, put it on the side, and keep it for themselves. In the casino, they do an hourly rake, right?
Yeah, that's a rake, too.
That's a rake, too.
Yeah. Yeah.
Different. You were taking money out of the pots and keeping it for yourself.
So basically what I was doing was, I had become much more lenient about who I was letting into the game, so my exposure was getting bigger. In some of those games where I was betting on the players and they were bad bets, I started to take a rake. This was during the last 6 months. The feds had put a confidential informant in the game because they were listening to the Russians' phone.
Who tracked that? And then a couple of months later I got a text message from one of the dealers saying, “Don't come here. The FBI is here looking for you.” Finally, I knew it was game over, and I just wanted to go home, even though I'd pushed my family really far away. I just wanted to go home, so I tried to book a plane ticket from JFK to Denver. My credit card got declined, then my next card got declined, and I logged into my bank account and it read 99,999,000.
The Division of Asset Forfeiture had taken everything because your property, unlike your personhood, doesn't have the presumption of innocence—except maybe in Florida. I'm not up on asset forfeiture. Now you're pinched: you get shaken down by the mob, then you get pinched by the feds.
My lawyers called and said, “You know, she can sue us because this is on the civil side, but anything she says will also be counted as a confession.” They said, “Do you want her? Are you pursuing any criminal charges?” They said no, so I could try to get my money back.
I moved in with my mom. I felt really sorry for myself, and it took me about 2 years to put my life back together. Finally, I got this little job in Los Angeles, moved back into this little studio apartment, and thought, “Okay, it's a fresh start.” Five days later, in the middle of the night, 17 FBI agents with machine guns and high-beam flashlights put me in handcuffs and shackles. They put this piece of paper in front of me that said, “The United States of America versus Molly Bloom.”
Wow. Wow. What a year.
I was really running hot.
Yeah. Wow.
A couple of bad beats. I had a day and a half to get to New York City to find an attorney.
And you're broke.
And I didn't have a penny.
Yeah. Wow. How does it all resolve? How does the story resolve?
I found someone honorable and great to represent me. I didn't have money to fight it, so I pled out. The prosecutors wanted a meeting with me. This was the Southern District, and they really wanted me to become a CI. They weren't interested in the Russians or the Italians; they were interested in the billionaires, the politicians, and the celebrities.
Who were there for poker, specifically?
Yeah. Let me be really clear: there was no Epstein in my game.
Right.
So they said—
They wanted you to be a rat against rich people, politicians, and famous people.
Yes.
What did they think you were going to overhear? Murder plots? What were you going to be able to tell them?
Business deals. I could have given them leads for all kinds of stuff.
Yeah. Crime—
For sure.
Was this Preet Bharara, who was running the Southern District? He's also famous for getting rid of online poker.
He's a pretty by-the-books guy, for sure.
Yeah. The Southern District, of all districts, is known for being the most hardcore, politically ambitious, and—
Sure. Right.
So, did you go to jail?
I didn't. They said, “If you're willing to work with us, we'll give you all your money back and we'll give you a deferred prosecution, which will keep you out of prison.” I had about 48 hours to make this call. Where I got to was that this was my fault. I had near-perfect information about the laws. I had all these opportunities, I had loyal clientele, and I found this loophole. I was the one who decided to make this choice.
To turn around and drag these people who had families through this shit, based on my own bad decisions, just didn't feel like something I wanted to live with. So I turned down that offer and waited to get sentenced. We all thought I was going to prison, and I got a judge who was very disappointed in my life choices, but basically said, “You had a life before this.” I had character letters from professors and ski coaches, and I had a lot of people show up for me who had made better decisions than I had made in life. He fined me a lot, but I didn't go to prison.
But then I was 35 years old, millions of dollars in debt, and a convicted felon. The tabloids were telling this really reductive tale. How do you come back from that?
I decided there was a story here, and if I could monetize that, maybe it could address the reputational harm and the financial harm. I mean, I was millions of dollars in debt. So I wrote a book and waited for my life to change. Then I think 10 people read it, and probably 8 of them were related to me.
But it was still my only idea, and I still believed in it in my gut. I made a short list of the most successful filmmakers in Hollywood and thought, “Why not? Why not just go for it?” They needed to be brave because there were also a ton of people, as you can imagine—
Yes.
Even though I'd fallen on the sword legally, and even though I hadn't implicated people in the book, they didn't want exposure, and I get that. Aaron Sorkin wrote A Few Good Men, The Social Network, and Moneyball. He was my favorite writer and also the highest-paid screenwriter at the time, which, if you're gambling—which we always are, right?—is a good bet.
Anyway, getting to him wasn't easy. I finally got to him, and I remember, before I walked in, thinking, “What am I doing? Millions of dollars in debt. My book sold 10 copies. I live with my mom, and this is the highest-paid screenwriter in the world.”
So you got a meeting with him.
I did.
And he had—had you sent him the book, obviously?
It was somebody that I bothered relentlessly.
Right. So, to put the sales hat on again, you were relentlessly pursuing the sale.
Yeah.
You were all over this guy, even though—
Yeah.
—even though you weren't making any money, you just kept going.
Yeah. I had met with other screenwriters, and they were kind of a big deal, and I was like, “No, no, no.” My brother said, “You can't keep passing. You live with your mom.”
What did you say when you got in the room?
I told him my story, and I think my legs were shaking, but I had this game face on. When I was done, he said, “Well, I'll tell you one thing, kid. I've never met someone so down on their luck and so full of themselves.”
Wow. It's a good character study.
Yeah. And then they made an offer.
Yep.
And then they paid, and you used that money to pay down this fine you got?
I did. I just finally finished paying off the government last summer.
Wow. Wow, congratulations. I guess, just to ask you the hard question, which you kind of answered: I was always wondering, how does one make the decision to write this tell-all book, and what was the fallout from that book? I remember in L.A. people talking about the book coming out. Everybody was really scared about it.
You didn't put people's names in it. You specifically chose to—
I put their names in it if they had talked about playing in the games.
Right. So you took some steps there, but you did make a decision, with all these people who put you in business, to basically turn on them and tell their story. There was no nondisclosure agreement; you hadn't made any agreements not to talk about it.
Well, I didn't turn on them. I actually supported them at every turn.
Well, I'm just saying—
I could have gotten a lot of money back and a deferred prosecution.
Okay. Yes, in that case. Yeah.
And then the publishers were willing to pay me 6 or 7 figures for a celebrity hit piece. I was broke, living with my mom. Again, I turned that down. I chose to work with a screenwriter who was absolutely clear and willing to contract that we weren't ruining any lives.
Got it. Great. And just so you know, everybody in the poker games—all the dealers, everybody involved—had to sign nondisclosure agreements.
Probably smart.
Probably smart, yeah. Do you still need to face fear in the face to feel like you're doing what you want to do?
Yeah. I don't have this addiction to that anymore, but I will always choose courage over comfort. I pay a big interior price internally if I don't.
But it's not like this thing where I need that adrenaline hit to make me feel alive. I like it; I pick my spots now. I have a 3.5-year-old daughter, so I knew before I brought a kid into the world I needed to do a lot of work on myself.
You learned a lot about yourself.
I wonder what you could tell us about the nature of the men who are obsessed with playing this game at these stakes—the camaraderie, the competition, and the chaos. What have you learned about the nature of these men?
Well, again, I think there are a couple of different archetypes.
Okay, tell us.
There are the ones who are on a self-destructive bullet train.
So it's not just high-stakes poker, right?
Yeah. It's putting their marriages in bad places in very egregious ways. There's drugs. It's the hedonic treadmill gone crazy.
Got it.
Then there are just the highly competitive people who are very comfortable with volatility—in fact, they prefer volatility and chaos—but still have some semblance of control over themselves. Then I think there are people who play because they love the game, because they like the aspects of it that make it an incredible game. They like the psychology. They like seeing the results of making high-level decisions with very limited information. They like the mental and social thrill of it, the camaraderie and the competitiveness.
Who's the best celebrity poker player in all the years that you saw in these games? Who is the best?
Tobey Maguire.
Yeah. And who is the second-best?
He wants you to say Chamath, but we were going to carve him out because he's not—
Look, I played with Tobey for 20 years. I would have said Tobey, too. I think he's exceptional.
He's a grinder. He's tough.
Yeah, he's tough. He was the only one in the game who was tight. I guess second would be Ben Affleck.
Yeah. Affleck's a good player.
Yeah. He's definitely smart. He definitely knows what he's doing. It depends on where he is in his life.
Yes. Politician-wise, can you say or no?
I haven't named any of the politicians because they haven't been named.
Yeah. Okay. Business people?
Once again, they haven't named themselves, so we'll leave them unnamed.
And, Molly, you were telling us before that you do some kind of speaking work around sales. This is where I'm so interested. What are the things you tell people when you do those events? What is the big takeaway from your experience?
So, a lot of people—there's this small body of science called affective presence. It really focuses on what's going on subconsciously. If you work backward from core human fears—which I think is always a really good thing to do—after dying, being alone, and public speaking, what are people most afraid of? They're afraid of not belonging, not being worthy, people stealing money from them, and so on.
When you start to think about what kind of emotional footprint you're leaving with these people—how can I disarm them and also cultivate trust at the same time?—it takes a level of intentionality. A lot of us walk into a room thinking, "What's my résumé? What are my sound bites? What's my pitch?" instead of thinking, "How can I make this person feel like I'm with them, like this isn't a zero-sum game?"
There are just a couple of things that you can do. Listening is a huge one: listening with full presence, not listening while you're constructing your response, and asking open-ended questions. Go down this road with someone. Have some warmth about you and be affirming, but also be authentic.
And practice hard empathy. Easy empathy is with people you relate to, people who have a similar experience to you. Hard empathy is sitting down and having conversations with people whose views you don't like, whose personalities you don't particularly like, and trying to get to a place where you can understand them.
Yeah.
Making that effort.
Yeah.
Making that effort. It's interesting: humans hate uncertainty. Without an edited brain—and I mean edited by doing that work and meditation, whatever your mind-training tool is—the brain thinks that uncertainty is a metabolically unsustainable state, so it equates uncertainty with fear.
How can you start to give people that sense of certainty? Also, how can you become aware of it in yourself? If you know that you hate uncertainty, what you do is forage for some subjective truth and then cling to it. That's a big handicap.
To start to do the work of relaxing with uncertainty and being more curious, rather than needing to have this illusion of control—there are a lot of things that aren't so obvious or instinctual in the art of impact and connection.
It can also force you to let go of priors, which allows you to adapt and evolve. I mean, being able to adapt, being able to court change, and even reframing it as, "This is exciting" or "This is interesting."
What an incredible life you've had, ladies and gentlemen. Let's thank Molly for joining us. Thank you, Molly. And let's thank also Oracle. Thank you for hosting. Um, and my lord, we're going to have a great weekend. I'm going all in.