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Boldness is the courage to get free and be free. That means internally getting free from your ego and from anything that keeps you smaller. Adam Gilad has excavated boldness in conversation, presentation and lifestyle choices. He’s been a dating, relationship, lifestyle, and business coach and teacher for fourteen years. He says you’ve got to be bold. You’ve got to pivot, pay attention, and constantly learn because the whole business has utterly changed. The pace of learning in life requires boldness. That means boldly facing down your habits, mindset, what’s keeping you small, and boldly acting on your will as long as you’re not hurting people. As a prolific author, speaker, screenwriter, film producer, mentor and coach, Adam has a huge heart, wisdom, and passion about leading people into living the bold life. He talks about his experience, his vulnerable upbringing in his past, and how he’s gone from a man who felt closed down after an epic change around the year 2002.

151: The Bold Life with Adam Gilad

This is The Bold Life with Adam Gilad. I’m very excited to have him on the show. He’s a guy who has been in my orbit for years. We were like two cats walking around the jungle, checking each other out. He talks about his experience, his vulnerable upbringing in his past and how he’s gone from a man who felt closed down after an epic change around the year 2000 to the man he is today. He’s one of those with a lot of energy in New York-type speakers. He brings a lot of wisdom. If you like more shows, please visit Visit us on iTunes, Stitcher, your favorite podcast app. Like us, subscribe, and leave us some comments and give us some stars. We’d be so grateful.

Adam and I had dinner years ago and then reconnected. I was very happy to participate in his second Bold Man Summit, which is available for pre-sale. We had a great conversation there. I thought it would be amazing to bring my brilliant friend to the show. Welcome to the show.

I’m happy to be here, Robert.

How would you define living a bold life?

I did a lot of things in my life. I was in the music business, Wall Street and the academe. I was a TV writer and producer for many years. My career got decimated quickly when reality TV came in. I was writing and producing movies for television and cable. I found reality TV stupid. I even proposed a show called Tits, Tits, Tits to VH1 and they loved it. They said, “Really?” and I said, “Not really.” I said, “I quit.” I walked out and I said to my agent, “I quit, I can’t do this.” I started writing. I got divorced around then at the same time my career fell apart. When I finally got it together to think about dating again because I’d been married a long time, I had two little kids. I discovered online dating, which was great for me because I taught writing at Stanford. I was a film writer. I worked in comedy and writing. It was easier for me back then when people wrote online. At least they had profiles that said more than DTF. I always joked that if Shakespeare had a sonnet, I had the online profile.

I had fun because I had two kids. I didn’t go out and had never been to a bar. I got married so young. I didn’t know anything about being a single guy out there. I experimented with language and ended up writing books for men and women. It was about how to write the language that the other gender feels. I found that men had no idea how to write and communicate with women and women had no idea how to communicate with men. I had a huge background in language, communication and semiotics. I did an analysis of what wakes up the other gender. In my studies, I came across a book called 59 Seconds. It was authored by a professor named Richard Wiseman in England who’s funny as hell. He collected a bunch of university studies on how to change your state or someone else’s state in under a minute. Moreover, a bunch of studies around what made men attractive to women shows, conclusively, the number one thing that attracts women to men initially is his boldness. An act of courage or some calculated risk or helping a woman in a moment of danger.

TL 152 | The Bold Life

The Bold Life: The number one thing that attracts women to men initially is his boldness.

More than kindness and those other things that we like to talk about, that act of boldness is what wakes women up. I excavated boldness in conversation, presentation and lifestyle choices. In my workshops, I would get men to wake up to what does it mean to be a bold person? What does it mean to state your will cleanly? Before #MeToo, I was saying, “If you want to kiss a woman, say I would like to kiss you and see what she says. If she says, no, then don’t. If she doesn’t say anything, closes her eyes, leans her head back, okay. If she says, yes, then great.” Don’t hide, don’t use the word unhidden. It started with this idea of what does it have to take a risk into looking at your whole life. Seeing how in our economy, because everything is shaped by the economy socially, you’ve got to be bold. You’ve got to pivot, pay attention and constantly learn.

I’ve been a dating relationship, lifestyle, business, coach and teacher for fourteen years. The whole business has utterly changed. The pace of learning in life requires boldness. That means boldly facing down your habits, mindset, what’s keeping you small and boldly acting on your will as long as you’re not hurting people. That’s the second half of boldness. Boldness is the courage to state your will. Also the opening line of my forthcoming book on boldness, “Boldness is the courage to get free and be free.” That means internally getting free from your ego and from anything that keeps you small or mean or contracted. That’s a general introduction to how I look at boldness. Boldness is the courage to state your will and to act on it and it’s the courage to be free.

Our work is so aligned, it’s obvious on many different levels. My wording of the same exact thing you’re talking about is, “Being authentic, telling the truth, and stop lying.” Withholding is lying. It’s all about how to cross that chasm from thought to connect with another person. To be bold is difficult. Let’s bring this pragmatic here. There’s a guy who hasn’t done any work yet, has so much desire inside of them and he doesn’t even know what it means to be bold. How would you guide him in feeling competent?

I would have him come to my Awakening Weekends. There’s so much information in the world that it gets lost. How many times have you signed up for a webinar and didn’t show up? There’s too much information floating around, and people need hardcore experience. I do these awakening weekends, These are three-day deep dives into three aspects of life. The first day we look at what our thought patterns are and challenge them, “Is this something I’m thinking just because I’ve been thinking it a long time? Is this a strategy I made up in high school or when I was a little kid, so I could feel safe?” Even though safety is a total illusion.

Really looking at our life choices and our belief systems. I don’t like to use the word belief, it’s an operational thought. It’s something I’m operating on at the moment. Louis C.K. did a great job of pulling that apart. He goes, “We all have our little beliefs. These are my beliefs. They are mine. I don’t act on them, but they’re mine. I feel better because I have beliefs.” The first day we look at our belief systems and really challenge those. The second day, we look at awakening boldness in our own relationships with women. We go through a lot of practices around that. We bring in brilliant women to work with the men.

On the third day, we look at bold leadership. It doesn’t mean you have to run a company. One of the things I railed against back was when the game came out. The idea was that you have to be an alpha man. Not everyone’s an alpha man. Most women don’t want an alpha man because these men are usually too busy to be intimate, warm, sweet and kind. I created this notion called being Spiritually alpha, meaning you’re alpha over your life. If you draw a three-foot circle around yourself, be the king of your life within there. You make the decision on what happens within that circle. That’s all you need to be. It’s not about status or ruling over other men. The third day we look at a bold leadership of your own life and grabbing the captain’s wheel of your life. There are practices with other men and practices with women I bring in to shift consciousness. Those are the three areas that I’ve discovered, that have been the most helpful to get guys to wake up and start that shift.

That concept of the state change from 59 seconds, what I’m hearing and what I believe, is that it’s in all of us to use our language to be kings, to love, self-validate, self-habit and self-empowerment. There are so many garbage or packaging or plastic bubbles on top of us. That bubble wrap feels like it wraps us from having that. In the workshop, it’s a state change. It’s a change in beliefs and mindset.

I want to be careful here because Tony Robbins is all about state change. He does great work. There’s that famous video where a woman brought up, “What about when we’re victims?” He couldn’t hear because he is so against victim mentality, which is fine, I’m all about that. He was not in the state of being a victim to anybody because he’s a giant. He couldn’t hear her. Tony Robbins does great work and creates state change. They have a change of state, but they don’t have a state change of stage, which is what I’m interested in. It’s a beautiful distinction I learned from David Deida. He was my business partner for two years. He was a great teacher.

Find nuance truth amid the noise. Click To Tweet

A change of stage means you shift your life. It’s easy to get on a weekend and change something, but I’m interested in changing your stage of life. He has those three stages, but I’m interested in freedom. He’s more interested in when he talks about stages, massive and feminine polarity. I’m interested in freedom and liberating ourselves from the things that we’ve created to make ourselves feel safe. That may have worked when we were three years old, seven years old, teenagers, in our 20s or 30s. As we go through life, we need to stop and reexamine, “This doesn’t make sense anymore. Is this true for me?” I don’t want to get people excited, I want them to make actual life shifts. At the end of every unit of my workshops, there is a commitment setting stage where we set commitments. Then we have accountability and all that stuff to make sure that it becomes a habit.

You’ve been plugged in seriously for eighteen years. I know you’re connected to men and #MeToo. You have a great forum on Facebook, it’s called #MenMeetMeToo. You’re obviously witnessing, caring, feeling and noticing what’s happening. How would you describe the last ten months since the Weinstein effect?

I’m afraid that it is discouraging in some ways. As you’ll see in that forum and everywhere, the nuanced and intelligent discussion gets immediately tribalized. As a former academic, it’s everything against what I’m trained to do, which is to find nuanced truth amid the noise. Everyone hones in on the extreme voices. There were women who’d say, “Toxic masculinity, men are toxic.” Suddenly men will go, “Screw that. I don’t want this. This is garbage. I’m not a toxic person. I’ve made mistakes, but I’m not toxic.” Women and men will say, “I was taken advantage. My friend lost everything in divorced. This law and that law.” No one’s listening. They’ll be immediately tribalizing into your bad, I’m good, which is a waste of time. That’s what happened in the last ten months. The long arc of history, something very important happened. The reason I created that group, for personal reasons, because it’s such an important issue to me.

I have a particular tenderness for the feminine. My own personal life going back to childhood, my sister who died and my mother, but also the scripts that I’ve made. I’ve never assaulted anyone. I’ve never been in a position of power, fortunately. I had never worked for anybody. When I was a graduate teacher at Stanford and I had office hours, I taught poetry to freshman girls. My door was always open. I never wanted anything untoward. That was the only chance I ever had to sexually harass anybody. In the long arc of history, I consider #MeToo to be the equivalent of 1964 the I Have a Dream speech, that period of Civil Rights for African-Americans. It’s an enormous cultural, sociological, human wakeup call once it sinks in.

Now, that we’ve spent the last 40 years curing racism, that’s not an issue anymore. We get to think about this. It’s not going to be overnight, but there’s a large arc of history where men are waking up to, “There are acceptable ways of behavior.” What that acceptable way is not clear yet. As masculine assertiveness is sexy, masculine aggression is not sexy. That’s cultural and that’s a question. Men will probably affirm this. One guy can say something to a woman and she finds him attractive and she won’t be offended. Another guy who she doesn’t find it attractive can say it and she will be incredibly offended. That happens.

I do want to note a wonderful distinction. Kamala Devi was on my podcast called F Normal!. She made a great distinction, which I’ve been quoting nonstop. She goes, “There’s a difference between calling out people for bad behavior and calling forth people for bad behavior.” Harvey Weinstein, Donald Trump, and Bill Clinton need to be called out, that’s aggression. Les Moonves, which is sad by the way, has been amazing and he’s been horrible to women. I’ve been reading the stories. These people need to be called out for abuse of power. Then there’s calling forth generally good men who haven’t done horrible things. Maybe they said a thing, made a joke or pushed a little too hard after a couple of drinks. Who needs to be called forth? My belief is that most men in our world are ready to be called forth into a higher state of consciousness in their relationships with women. It’s more constructive to have that nuance. Some guys need to be called out and kicked out. Most men, I’d like to believe, need to be called forth into their goodness and greatness. Those are some of the large trends.

A lot of it comes down to education. It’s the consent conversation and safe sex. In my opinion, before, it was something you had to do. Sexual harassment in the office or all these forms you filled out that you never read or signed. Even at school, there wasn’t like a lot of weight to the conversation about consent. I saw it in college and I didn’t do anything. I saw just the epic lack of information. My favorite thing about #MeToo, first and foremost, is bringing it to the forefront so we can start to have dialogues. I do also see that chasm because I see men trying to protect themselves, “I’m not one of those people. I’m not one of those guys.” We all have those tendencies inside of us to do it. We’ve all experienced and seen it, so why not just have a dialogue around it to stop the shame even for the conversation about it.

It’s out in the public domain, which is good. There’s going to be a long time of confusion. Without being biologically essentialist, Jordan Peterson falls into this sometimes, we’re not destined to follow our biology. It’s part of it. We will be biologically-driven, especially when we’re young. Kingsley Amis, the great British novelist, said that when he hit his 50s, he woke up and felt like he’d been chained to a maniac for 35 years, his libido. It’s a question of calling forth men into their goodness rather than calling them out, “One mistake and you’re dead. You’re gone.” It’s going to be a process of learning conversation, forgiveness, relearning. It’s the only way to go.

TL 152 | The Bold Life

The Bold Life: A change of stage means you shift your life. It’s easy to get on a weekend and change something, but I’m interested in changing your stage of life.

You install the new carpet, you’ve got the bad chemicals in the carpet. It’s got to off-gas for six months before it’s healthy to sleep there. It’s the same thing, it’s going to take decades and decades for minority groups and the people who have been abused. They need time and space. There’s this feeling of men who want to say, “Get over it. Forgive me.” I don’t think it’s going to be that. I do think there’s a process of acknowledging, being aware of it and going forth from that spot.

Forgiveness is an interesting thing. We both come from a Jewish background. The Great Day of Atonement, Yom Kippur, you state what you’ve done publicly. Before you can get forgiven, you have to go back and make up for any damage that you’ve caused. In the traditional Jewish world, that’s real. When I was living in Israel in one Yom Kippur, there was a young guy who showed up with my beautiful Raleigh road bike that was stolen. They become religious in the interim. This guy shows up with my bike and I was so happy. You go back and you apologize. You go back and make up for what you can and seek atonement and forgiveness and you do your very best. That’s got to be the process. You can’t just say, “I’m sorry, leave me alone.” You say, “I screwed up and here’s my commitment.” I’ve done that my own personal life because I screwed up a good relationship. When I met the woman who’s currently in my life, the first night I was with her I said, “I want you to know something. I screwed up my last relationship. This is what I did. I’m 100% committed to never doing that again.” It’s become part of my identity. That’s what has to happen socially and generally.

You’re running your fourth book, 21 Gateways into Boldness. Is that the title?

Yes, I’m working on the big fancy title up top. There are 21 practices, I call them gateways because I’m not a big fan of laws. There are gateways and openings there. I’m a very practical person. I don’t feel like a book will have all the answers. Answers come with creating systems in your life and accountability. There are gateways that open you up to living freer.

Before unHIDDEN was formed, it was Extraordinary Practices for Modern Living. It went to unHIDDEN. What are your top three or four gateways that people can take to living a bolder life?

One is this deep notion of identity, there’s nothing called You. You’re a verb, not a noun. That’s one of the big reframes. Once you understand that you are a consciousness that’s unfolding. Who I am two seconds ago is not who I am now. There’s tremendous freedom there to recreate your life from the ground up at any point in your life. Too many people are very sloppy with language. We use the word I, but what is I? I did a PhD course at Berkeley on this subject and I couldn’t even wrap my mind around the questions that kept getting brought up.

To simplify the notion for me is to see yourself as a verb. I am unfolding all the time. I’m not a human being, I’m a human becoming. When we use this language, we open something. Something clicks in our brain and allows us the freedom to start reconstructing how we want to be perceived and how we perceive ourselves. That’s one of the grand structures that I like to suggest. It helps free people to take a bold action because you’re not trapped by this old notion of what I was. It’s hard work shaking off all wiring. It’s not a philosophy thing, it’s a neurosculpting thing. It’s neurobiological. How do you create new pathways to create habitual action that isn’t dictated by the pathway you’ve created from your past I? It’s a practical walking path once you understand that you’re a verb.

The other big thing for me, that bespeaks my nature, is this notion of skilled play. I almost did my dissertation on the play as an identity. Homo Sapien Sapien is a man who thinks about thinking. Who came up with that definition? Philosophers, scientists, and university people. We are thinkers, but there are other traditions about what we are. There’s a famous work called Homo Faber. We’re the man the maker and Faber as in Fabrication. We define ourselves by what we make. There’s another tradition called Homo Ludens. Ludens is the same root as ludicrous or ludic muscles used in smiling. We’re playful creatures.

If you watch kids, they’re as playful as they are thinking. I happen to love this notion of play as a way to frame human activity. It’s liberating to me because it opens up the possibility. There is a wonderful book called Finite and Infinite by James Carse. It changed my life. For people who may not have read it, there are two types of games. There are games where the rules served to create a winner and a loser such as a basketball, baseball, football, politics, the way it’s constructed now. There’s a game where the rules are constructed to ensure the playing of the game.

Operate on what inspires your greatness. Click To Tweet

The goal of the infinite game is to continue to play, the goal of the finite game is to win or lose.

What is an infinite game? Love, intimacy, self-growth, understanding, awareness, all the things that matter in life. I’m looking at relationship and intimacy skills, not as work. Everyone says marriage is work, relationships are work. It’s hard, but it doesn’t mean it’s work. It’s actually skilled play. Lebron James didn’t become great without learning skills. If you want to be great at relationships, you’ve got to learn skills. There are skills to learn as you will know that increased intimacy, communication, trust, and all those things. I like to look at relationships specifically and life in general as skilled play rather than work. It makes me happier to have that frame. It also wakes up a more creative part of our brains. Suddenly, relationships in life don’t become a burden, but it becomes an open arena to go play in. You wake up and play better the next day. There is no work burden if you failed or won. It’s a great frame for life.

TL 152 | The Bold Life

Finite and Infinite Games

One of the parts of the Finite and Infinite Games is that infinite games are composed of finite games. Finite games don’t include the infinite games. To use that basketball analogy, Michael Jordan was the best ever, in my opinion, because he learned from his losses in a finite game. People look at the relationship as a win or lose, in a very commerce-based success. They don’t look at it from the whole virtue of the whole infinite game. That breakup was hard and as painful but look at the whole man you’ve become from that breakup. Owning the mistakes you made and the things you didn’t do, so you could come to your new or current relationship and say, “I screwed up the last one. Let’s not do that this time.” That is mastery to me. The infinite game is how he, she or they learned from their losses.

There’s a great passage in Zen Hoops by Phil Jackson when he was tapped to coach Michael Jordan and the Bulls back in the ‘90s. Phil wasn’t a super well-known coach at that point. He was a little scared. He showed up in Chicago and Michael Jordan came in like the king of the world and said, “Tell me what to do, Coach. I’m coachable.” A smile spread on Phil Jackson’s face and he goes, “This is why this guy is a champ.” We all screw up, we’re always learning. It’s fun having adult sons now and having relationship discussions. We’re all going out with their mom who’s coming into town. We’ve been divorced eighteen years. I remember in the kitchen once, we were arguing, and we were in our early 30s. She goes, “That’s how I feel.” I was so heated, I’m like, “Yes, but your feelings are irrational.” When we looked at each other and I go, “You win this one.” When you look back at how unaware we were earlier, you have to laugh a little and treat it as play. Keep playing the game.

You did one before, The Bold Man Summit. What was your favorite part about it? Your new one is coming out, give us some details.

Let me explain why I do these summits. The last one is called the Inspired Man Summit. I had a rough year. I had a very painful breakup which I instigated through my own bad choices early on. I did a lot of surf-thinking by literally going off to Hawaii and sitting on a beach for a month. I was looking at the waves, doing some therapy and thinking, “Do I need to do a reset my own life?” I’ve always been driven by what inspires me. I started thinking about the people in my life who inspire me. I decided to create a summit where I picked about 30 of the most inspiring men I knew. My idea was I wanted men to be able to find their teacher. Who really inspires you? People will click with different people.

I interviewed the most inspiring men in business, men’s work, and philanthropy. It was a great experience. People found their teacher and it helped get the word out from a lot of great teachers. This one is the Bold Man Summit. This is men who have taken bold action in their lives. You’re one of them. They have taken a bold leadership position or have made big changes in their lives that weren’t necessarily easy but paid off in big ways or didn’t. They took real bold steps. Men, particularly, and women can listen. I’m having some women speak this time, Julian, who I think you’ve had on your show, who I adore. Women who understand bold masculinity for men to get inspired to take bold action on their highest goals or most noble goals. The things that called them forward.

Boldness is the courage to be free. Click To Tweet

That’s at and there’s an early signup page. We go live on September 9 to 17, 2018. If you miss it, you can buy those interviews later. Each interview is designed to give inspiration for men to figure out how to take bold action in their lives. It isn’t just like, “You’re a wussy, you’re not taking bold action.” There are pathways in our brain that we’ve trained ourselves to follow for decades. It’s not that you’re weak or you’re not a real man or anything like that. There are actual shifts that need to be made to take bold actions and build the systems that support that bold direction. Every teacher in that summit offers a different angle to take bold action and install those in your life.

What would be the thing that you want people to remember you by? If you could impact the world, what would be that one thing?

As the years change, I change. I’m a verb. I’ve been teaching for a long time. When I teach, sometimes I’ll start with a story or sentence that I won’t remember. People in the audience know all my personal stories, the stories about my kids, the adventures I had, and how I became who I am. They know them better than me. The sentence that’s driving my life is, “Boldness has the courage to be free.” It’s a rich sentence because what’s boldness and what’s free, internally and externally.

We both grew up in suburban New York. Where I grew up, we used to call it Rock and Roll County. We called it that ironically. I bolted as soon as I could at sixteen because the suburban world with high school football teams was not for me. I know there was a bigger and more exciting world. I started traveling young. I wrote a novel when I was 23 called Lawrence of Suburbia. It was about, “I’ve got to get out of here and create an epic life.” It changes as I go, but freedom has always been on the thing that’s driven me on. On a deep level, there a hedonistic aspect of it that’s true for my personality type. I’m a lover of pleasure whether it’s great literature, wine, natural landscapes, or art. I delight in the beauty of the world in a visceral way which led me to be a writer.

Act on what makes you fascinated, happy, creative, and playful again in the world. If you don't, then what are we here for? Click To Tweet

The other part of it was experiencing death very early in my life. My sister died and I have never taken life for granted. I’ve never thought about, “I’m going to go get a job, work for 40 years, play golf in Florida and die,” which was the motto that you and I both grew up with. “Life is a bold adventure or it’s nothing,” said Helen Keller. Boldness and freedom are the things that have driven me and to really lock into what inspires me. In all my work, I encourage people to operate on what inspires your greatness. Act on what inspires and opens up your heart and makes your soul sing and soar. Act on what makes you fascinated, happy, creative and playful again in the world. If you don’t, then what are we here for? Boldness is the courage to get to live free so that you can live inspired. Those are the ideas that I’m operating on now.

Thank you so much for coming on the show. It was a great conversation. I could feel your passion and inspiration. I’m excited to be part of your summit. It’s an absolute pleasure to have you.

Thank you. It’s great talking to you.

Thank you so much for joining us for Tuff Love. The show will be on iTunes and Stitcher. You can find more episodes at Thank you so much, Adam, for your energy, passion, vulnerability and realness. Thank you for the work you do in the world. Boldness is the courage to be free. That is an awesome tagline for all of us to live. It is the ethos of Tuff Love. Be true, be free, ask for what you want and be deliberate. Learn to be free because I think that’s what we all truly want. Thank you so much for reading. Have a great day.

Resources mentioned:

About Adam Gilad

TL 152 | The Bold LifeAn itinerant veteran of Indian ashrams, Nepali and American Buddhist monasteries, Peruvian jungle medicine journeys and advanced Jewish study in the heart of Old Jerusalem, Adam Gilad leads his clients and students into conjuring a robust life of boldness, inspiration and freedom. A Stanford Humanities Center Graduate Research Fellow, Adam has long worked as a dating and communication expert, writer, Emmy-nominated Executive Producer, entrepreneur, father, thinker and spiritual adventurer. His journeys have carried him to stints on Wall Street, in Hollywood and to the creative consultancies for companies such as BMW Design, General Foods and Ogilvy Worldwide. His wicked, but wise sense of humor was showcased as the co-owner and host of National Lampoon Radio. He has explored themes of courage, justice and service in his award-winning work in television, live storytelling, university teaching and private coaching. Gilad brings together a unique mix of global wisdom traditions, advanced education and usable practices that has attracted a following of over 50,000. He has authored countless audio trainings and written several books, specializing in learning the “language” of the other gender, cultivating a dance of the sexes rather than a battle, the play of sexual polarity and fearlessness in self-awareness, self-evolution, compassion and forgiveness. He is the host and creator of the Inspired Man Summit, The Bold Man Summit, The Bold Life Awakening Weekend and The Smart Daters Academy. He is the father of two grown sons, who have taught him more than all the above, combined.

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