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Over the Wall with Rob LoCascio

by Rob LoCascio

Rob LoCascio invented webchat for companies. He founded a billion dollar company and has been on the entrepreneurial journey for 25 years. Along the way, Rob had to take risks and make mistakes; his journey to success was not a clear path. In this show, Rob shares his journey, invites industry titans to discuss their biggest mistakes and lessons learned, and helps real entrepreneurs work through challenges big and small.

Copyright: Rob LoCascio

Episodes

EP31: Mario Andretti

45m · Published 09 Dec 11:00

Despite facing immense challenges, Mario Andretti has become one of the most successful drivers in racing history. In this episode, we discover how his lifelong experience in this dangerous and exhilarating competitive sport started and what it took for him to succeed. From a young age, Mario and his twin brother Aldo dreamed of becoming racecar drivers. Despite the multitude of adversities, Mario became a world-class competitive driver who is now a family man and philanthropist aiming to teach the next generations about discipline and the value of resilience.

Tune into the episode to learn the story behind Mario’s success and how he became a legend!

Key Highlights:

[01:30 - 05:35] Formula One Legend, Mario Andretti, shares his life advice and why determination and decision were key to his success in a highly challenging field.

[05:50 - 07:50] Mario Andretti tells the story of how he became a race car driver and the role that faith and family support played in allowing him to overcome struggles.

[15:45 - 20:30] A disciplined mind keeps a race car driver alive, and a positive thought keeps him motivated and focused. Family is also a key factor in success.

[23:48 - 25:20] F1 looks like an individual effort, but it’s all about teamwork, which is required to keep a complex machine running.

[26:10 - 27:15] Which is more important for racing competitions, the car or the driver?

[32:28 - 34:30] You can never take things for granted as a race car driver, because any race could be your last.

[34:40 - 35:45] There can’t be one individual victory that defines you because each victory has something special, and they all build up into a career.

[40:09 - 45:10] Inspiration to succeed doesn’t come just from individual ambition but from your family’s support and the drive to help others.

Tweetable Quotes:

“Nothing that’s worthwhile to pursue in life will be a bed of roses. There’ll always be challenges. If you waste your time dwelling on your mistakes or blaming others, you’ll end up losing yourself.” -Mario Andretti

“One of the keys to my success was learning that it is bigger than just me. There is a whole team behind. These are people who have families and dreams. To win meant to show them that their work was worth it.” -Mario Andretti

“The car and the driver are inherently intertwined. A car cannot make up for what the driver lacks, and vice versa, no matter how good either one of them is.” -Mario Andretti

“One of the key aspects for you to succeed as a driver is to always include your team. Make them proud to be there and make them feel like they’re an important part of why you’re there.” -Mario Andretti

Don’t forget to visit Mario Andretti’s website to learn more about him and his career:

https://www.marioandretti.com/career-highlights

Enjoying the podcast? For more content, find me all over social:

Instagram: https://www.instagram.com/roblocascio

Twitter: https://twitter.com/RobLoCascio

LinkedIn: https://www.linkedin.com/in/rlocascio

EP30: OZ Pearlman

49m · Published 17 Nov 11:00

Get ready to be amazed! Magic is truly something that continues to capture the imaginations of humans. Today, Oz Pearlman is here to reveal that even though magic is in the mind, harnessing it can lead to something unique! Oz is a mentalist born in Israel (1982) before moving to America at 3. He was captivated by magic from a young age and started earning a profit from it at just 14 years old. He has since been featured on America's Got Talent and Jimmy Fallon. In this episode, we learn about his career journey and how he became successful in such a niche area. We dive into the importance of mastering the mind and how it can be used to take risks and succeed by overcoming failure.

Jump right into the show and learn how mastering the mind can help you do the impossible!

Key Highlights:

[00:00 - 06:47] How Oz was bit by the magic bug and hustled to make a living with it.

[06:48 - 10:50] Exploring humans’ innate intrigue with magic and the mind.

[10:51 - 18:46] Put in the 10,000 hours. How to harness the mind to grow beyond the point of failure.

[18:47 - 24:56] Human evolution is very telling. Survival traits passed down through humanity make it easier to read each other.

[24:57 - 31:20] Mental practices that build rapport and connections with people.

[31:21 - 39:01] Strong and creative minds stay ahead of the curve mentally and physically.

[39:02 - 43:03] Your drive to overcome difficulties will determine your success.

[43:04 - 49:32] (Oz performs a mental trick) How to set goals and exceed your expectations.

Quotes:

"Once I started doing well, I always wanted to give back. I've instilled that in my kids, but I think that if I had grown up where I didn't have that drive, I would've been lazier because I couldn't afford to be lazy." - Oz Pearlman

"[Magic] allowed me to get a lot of opportunities that I don't think I would've gotten otherwise because of the way you build rapport with people.” - Oz Pearlman

“It’s hardwired in our DNA to keep growing… Magic is amazing because it’s something that always stays ahead of what you know.” - Oz Pearlman

“There are certain things you have a gift for that I would call a talent, that’s innate, and you can develop it.” - Oz Pearlman

“It’s not physical; it’s mental. If someone had a gun to your kid’s head and said go run 50 miles right now to save their life, you would do it…! You can do it. You can dig deep and access those reserves.” - Oz Pearlman

“A lot of the best things come out of something difficult, traumatic; they create scarcity.” - Oz Pearlman

“Take on big things that you don’t know if you can do because otherwise, you’ll never push yourself on to the next level.” - Oz Pearlman

Want more from Oz? Check out https://www.ozpearlman.com/  and stay amazed.

Enjoying the podcast? For more content, find me all over social:

Instagram: https://www.instagram.com/roblocascio

Twitter: https://twitter.com/RobLoCascio

LinkedIn: https://www.linkedin.com/in/rlocascio

EP29: Julie Wainwright

59m · Published 21 Oct 10:00

You hear all the time that your past shapes your future, but it’s the execution that truly matters. Julie Wainwright is a fantastic individual. She's the founder of The RealReal, and a dot-commer, like me. In this episode, we get to hear about her childhood, the challenges Julie faced in her past, and how they’ve shaped her as a CEO and business owner. We’ll also dive into some real talk about how Covid affected her business and the people in it, as well as the adventures she went on in her early career that shaped the skills she would need later.

Tune in and learn how to turn your past challenges into future success.

Key Highlights:

[00:07 - 07:59] How Julie created a more sustainable fashion industry and how Covid presented significant challenges to her business.

[08:00 - 14:27] A lesson in crisis management—how Julie dealt with the Covid chaos.

[14:28 - 19:39] How to keep yourself physically and mentally strong without running yourself down.

[19:40 - 30:41] Julie reveals her background and how your past can prep you for your future.

[30:42 - 36:15] Find out how a corporate job at Clorox helped hone and shape Julie’s writing, networking, and execution skills for when she would go off and build a business of her own.

[36:16 - 44:22] Knowing when to walk away from something you created to start building a legacy.

[44:23 - 50:15] Same thing, different way: Leaders need to find a way to transform their businesses, not keep it the same way.

[50:16 - 1:00:55] Sexism and discrimination against women in the workforce are still a reality, with challenges that people need to recognize.

Quotes:

“It was that whole idea of, ‘you're smart, you can figure it out,’ [that] was already in me from a very early age by both parents—and then I HAD to figure it out.” - Julie Wainwright

“I don't know if there's a higher hand. I think you can connect to something bigger than you, and if you listen, I think you can get comfort in that.” - Julie Wainwright

“I don’t have a victim bone in my body… I wake up, and I'm like, ‘this is gonna be a good day.’ That's my first thought.” - Julie Wainwright

“This is really important for entrepreneurs: doing nothing is always much worse than doing something.” - Julie Wainwright

“It’s been an honor for me to be able to run the company and see this idea come to life in a way that transcends what one person could do.” - Julie Wainwright

“Recognize that the world that men maneuver in is not the same as the world women do.” - Julie Wainwright

Be sure to connect with Julie Wainwright.

Enjoying the podcast? For more content, find me all over social:

Instagram: https://www.instagram.com/roblocascio

Twitter: https://twitter.com/RobLoCascio

LinkedIn: https://www.linkedin.com/in/rlocascio

EP28: Joey Krug

37m · Published 16 Sep 10:00

These days, you can hardly talk about investing without cryptocurrency and decentralized finance entering the conversation in some capacity. Joey Krug, CIO of Pantera Capital, one of the largest asset managers in crypto, is here to shed some light on navigating this evolving asset class. We discuss how product and market analysis help them make decisions when investing in crypto, the relationship to traditional finance, dangers to consider when investing, and current events happening in crypto.

Dive in and learn how to mitigate risk and find opportunities in a very volatile market.

Key Highlights:

[00:00 - 06:23] Joey Krug and an Intro to the Defi Market: Alive, well, and not so different from traditional finance.

[06:23 - 12:38] What is a Maker DAO, and how do you participate in it?

[12:40 - 19:04] Joey talks about how he mitigates risk as a CIO managing highly volatile assets and sentiments surrounding DeFi right now.

[19:04 - 25:42] The most significant lessons Joey learned in DeFi trading: Being too aggressive, taking risk off too soon, and missing out on-chain analytics.

[25:42 - 31:49] The relationship between crypto and traditional finance and how knowing it can help you navigate the market.

[31:49 - 37:18] The cultural shifts within crypto have played a major role in what it is today and why it correlated with tech.  Culture is also essential when it comes to building a business.

Quotes:

"I think DeFi has drastically changed the way finance works.” - Joey Krug

"The biggest mistakes I've made when it comes to trading are basically in two categories.: One is taking risk off too soon, and the other is not taking risk off soon enough." - Joey Krug

“Twenty years from now, banks will compete on the UI layer, like what the experience is like for the user and all the stuff under the hood.” - Joey Krug

“What I hate in a culture is people who complain about a bunch of problems… What you should do is solve it for yourself, and if you can’t, service it to the person who can.” - Joey Krug

Be sure to follow Joey Krug.

Enjoying the podcast? For more content, find me all over social:

Instagram: https://www.instagram.com/roblocascio

Twitter: https://twitter.com/RobLoCascio

LinkedIn: https://www.linkedin.com/in/rlocascio

EP27: Anthony Scaramucci

46m · Published 22 Jul 11:00

The markets had been brutal, given the fluctuating conditions, pressing political issues, and fiascos all around. How do we navigate through this when it comes to business and investments? In this episode, Rob and Anthony advise listeners to be patient, size appropriately, and ignore the market drama. The risk involved with cryptocurrency investment requires the participation only of the brave and patient. With this, listen in as Anthony provides his insights into what’s ahead in the technology sector.

Key Highlights:

[02:04 - 05:39] - The key is to choose realism over philosophy when navigating the market. Have a plan and be more patient when things go wrong.

[06:20 - 08:40] - Be wary of confusing brains with a bull market. Understand the risk involved and be cautious of the cash flow.

[17:08  - 19:00] - When the business comes crashing down, the greatest bull market run in your life can happen. Don’t pretend that you know everything.

[21:31  - 23:14] - Cryptography requires adaptation and faith. This game is not for the impatient and fearful.

[26:38 - 27:58] - The administration is making a mistake by being indifferent to the stock market and failing to understand the harmony between Main Street and Wall Street.

[28:45  - 30:22] - Reclaiming America’s former glory requires strong-willed political leadership.

[37:02  - 39:05] - Anthony shares how he entered politics during the Trump administration, got blasted, and moved forward.

Tweetable Quotes:

"In the beginning, I was super frightened Rob, I made all of the classic bad decisions, overreacting to my emotions, and all the fear… And so you could be philosophical about that. Or you can be realistic, I'm going to choose realism over philosophy." - Anthony Scaramucci

"You're in a situation right now where a lot of really good things are happening, but current market sentiment is very negative… But if you're not patient, you can't be in this market.” - Anthony Scaramucci

“If you're not failing a little, you're not really living, you're not pushing yourself to where you can go.” - Anthony Scaramucci

“You don't wallow and you don't play the victim, you know? And you go forward.” - Anthony Scaramucci

Enjoying the podcast? For more content, find me all over social:

Instagram: https://www.instagram.com/roblocascio

Twitter: https://twitter.com/RobLoCascio

LinkedIn: https://www.linkedin.com/in/rlocascio

EP26: Charles Hoskinson

52m · Published 24 Jun 11:00

How do we picture a financially free world? In our current status, does identity privacy truly exist? In this episode, Rob and Charles tackle challenging the status quo with the Web 3 systems. Listen closely as they discuss its implications on inclusivity, governance, and identity under this ecosystem and how Cardano aims to solve the pressing issues of the design areas to make this feasible.

Key Highlights:

[03:08 - 05:32] - The bitcoin movement proved that it is here to stay. It is an industry to be taken seriously.

[09:59 - 11:55] - The winners of the online world are centralized companies. Web 3.0 focuses on undoing this by enforcing decentralization and a token-based economy through blockchain.

[16:59  - 18:57] - In the blockchain system exists transparent logic, which allows control over data transmission and availability.

[21:17  - 23:45] - Cryptography now focuses on new capabilities and building on the next generation of identity.

[39:23 - 30:10] - Cardano came about from solving three design areas - scalability, interoperability, and governance.

[40:54  - 42:59] - Facebook or Google should not decide your identity, but in Web 2.0, the vast majority of utility about you is heavily controlled by third-party actors.

Tweetable Quotes:

"It [decentralizaton] is really been a game of how do you make it better, faster, cheaper? It's also a game of how do you make it more accessible? And also a game of how do you make it secure, because the problem is, the bigger these things get, the larger their attack surfaces are. And there's no accountable party for when they fail." - Charles Hoskinson

"One of the big design areas that we have to figure out as an industry is how do we build protocols where the bottom up can maintain the systems, upgrade the systems and keep them competitive, and create reliability and security as if there was a centralized custodian, but no one's in charge?” - Charles Hoskinson

“We shouldn't live in a world anymore in a world that has overwhelming data and digitization to say, ‘Trust us.’ ” - Charles Hoskinson

Enjoying the podcast? For more content, find me all over social:

Instagram: https://www.instagram.com/roblocascio

Twitter: https://twitter.com/RobLoCascio

LinkedIn: https://www.linkedin.com/in/rlocascio

EP25: Jeremy Allaire

55m · Published 10 May 16:16

In this episode, Rob tells a story about how he began using one of Jeremy’s first products, Allaire Forums, and how it eventually led to the creation of Live Person. Rob and Jeremy also discuss how they got into the Internet in the early days, before the Web. They discuss the development of Bitcoin as a reaction to the financial crisis and a way to decentralize power. Additionally, they explain how the internet has evolved into an organism, birthing new platforms and technologies in response to data sovereignty, privacy, and security threats.

Key Highlights:

[04:05 - 04:47] - The open nature of the Internet enables anyone to communicate and connect with others around the world.

[07:33 - 11:43] - Web2 excitement was about democratizing access and enabling openness and communication for everyone.

[11:44  - 12:41] - The birth of Bitcoin and the vision for Web3 came from a need for humans to progress.

[24:29  - 26:32] - DAOs (Distributed Autonomous Organizations) could produce more value than even some of the world's biggest companies within the next few years.

[39:23 - 45:36] - The purpose of USDC is to provide a digital alternative to fiat currency backed by real assets.

[50:23  - 50:59] - Interpol's head of financial crimes research says that 98% of money laundering is in the banking system and goes undetected.

Tweetable Quotes:

"As entrepreneur, you're constantly being told why you're wrong." - Jeremy Allaire.

"The US Treasury Department's top priority in this space is not how do we go launch a digital dollar. It's how do we put in place a regulatory framework around large-scale dollar stable coin issuers like Circle” - Jeremy Allaire

Enjoying the podcast? For more content, find me all over social:

Instagram: https://www.instagram.com/roblocascio

Twitter: https://twitter.com/RobLoCascio

LinkedIn: https://www.linkedin.com/in/rlocascio

BONUS: Greatest Hits 2021

1h 1m · Published 27 Dec 18:28

What a year it's been here at Over The Wall. I've been fortunate to interview incredible guests, from an astronaut to a chef to a neuroanatomist...I could go on. In the spirit of that, I wanted to present you to you some of my absolute favorite moments from the year in this special edition episode. It was incredibly hard to pick, but in this greatest hits mashup, you'll hear from: Ryan Serhant, Edward Norton, Anthony Di Iorio, Suze Orman, Deepak Chopra, Melissa Bernstein, Marc Randolph, Reshma Saujani, Lisa Bilyeu, Tim Storey, and Kara Goldin. All incredible minds I was lucky to speak with.

I look forward to many more riveting conversations in the future and hope you enjoy this special episode to cap off the year.

I'd love to know who you think I should be speaking with in the New Year. Who is inspiring you? Who is pushing themselves and being upfront about the mental game it takes to be an entrepreneur? I'd love to have them on. Let me know. You can find me all over social:
Instagram: https://www.instagram.com/roblocascio
Twitter: https://twitter.com/RobLoCascio
LinkedIn: https://www.linkedin.com/in/rlocascio

EP24: Michael Clinton

47m · Published 15 Dec 20:27

This week's guest is a man who has made an enormous impact on the world of culture, media, fashion and beyond. Michael Clinton has served as executive vice president at not only Condé Nast but also their direct competitor Hearst. He was the publisher that grew GQ to be the iconic publication it is today. Not only that, he is a prolific photographer, writer and world traveler. His story will push you beyond your comfort levels.

For more content about entrepreneurship, founding a company, raising funds, or to just ask me a question, you can find me all over social:
Instagram: https://www.instagram.com/roblocascio
Twitter: https://twitter.com/RobLoCascio
LinkedIn: https://www.linkedin.com/in/rlocascio

EP23: Michael Chernow

55m · Published 29 Nov 19:43

On this episode of Over The Wall, I interviewed renowned restaurateur Michael Chernow. You may know Michael as the founder of the immensely successful Meatball Shop, or his seafood spot Seamore's. We talk about all of that in this episode, but also dig deeper into his past, how it affected who he is today, his strict morning routines and workout regimens and the mental capacity it takes to make it all happen.

I know you're going to love this one.

For more content about entrepreneurship, founding a company, raising funds, or to just ask me a question, you can find me all over social:
Instagram: https://www.instagram.com/roblocascio
Twitter: https://twitter.com/RobLoCascio
LinkedIn: https://www.linkedin.com/in/rlocascio

Over the Wall with Rob LoCascio has 40 episodes in total of non- explicit content. Total playtime is 30:19:34. The language of the podcast is English. This podcast has been added on August 30th 2022. It might contain more episodes than the ones shown here. It was last updated on April 5th, 2024 10:17.

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