The Generation Hustle Podcast

Episode 69 is with Robbie Crabtree, Founder of Performative Speaking! Robbie is a retired trial lawyer turned Startup Founder Coach turning founders into powerful storytellers. Having started his career in the legal sector, Robbie helped victims get justice for violent felonies, murders, & child abuse cases as a successful trial lawyer. After eight years of competitive storytelling in a courtroom with 102 jury trials, Robbie realized that his storytelling abilities can be used for much more. Since shifting his focus to helping founders in Seed to Series C levels as a strategic advisor & coach, Robbie has helped clients raise over $135M in venture funding, build companies worth billions, and make their vision a reality. We talk to Robbie about his career pivot from lawyer to startup coach. He explains the makings of a great story-teller, how to pickup on cues when people are lying, and the mistakes that founders make with pitch decks. He also details his steps to scaling his influence and how to balance authenticity with growth. This was a great conversation with so many learnings throughout that we hope you enjoy! Robbie Crabtree https://www.robbiecrabtree.com/ Timestamps  1:18 - Background & Career  7:11 - How to Pivot Careers With Your Skills 10:40 - What Makes a Good Story/Story-teller? 13:50 - Social Media “Guru’s” 17:50 - Jeff Bezos’ Story-Telling in front of Congress 19:21 - How to Tell If Someone is Lying 24:00 - Biggest Mistake Founders Make with Pitch-decks 31:00 - Resources to Become a Better Story-teller 33:39 - Robbie’s Approach to Clients 38:27 - How To Scale Your Influence 42:38 - Validation Through Status 45:36 - Authenticity & Growth 48:24 - Failure & Triumph 50:18 - Lightning Round

Episode 68 is with Dennis Xu, Co-Founder of Mem Labs! Mem is the world's first self-organizing workspace that leverages artificial intelligence to equip knowledge workers in the world with the information they need to do their best work. The free app is an early access platform dedicated to pushing users to quickly jot down their thoughts without focusing too heavily on the underlying organization of them. We talk to Dennis about his journey to founding Mem and the inspiration behind it. He details the difference in tech landscapes between Canada and the USA, his experience at Stanford University, and how they secured a $5.6M seed round from Andreessen Horowitz. Dennis also explains important skills for builders in tech as well as what a day in the life of a cofounder looks like.  This was a really insightful conversation that we hope you enjoy! Mem https://get.mem.ai/ Timestamps   1:18 - Dennis’ background   4:44 - Tech in Canada vs. Tech in USA  11:35 - Shift to remote work  16:40 - Experience at Stanford  21:14 - Must have skills to be a builder  25:38 - Hard Skills vs. Intangibles  27:30 - Three types of workers  32:06 - Navigating terminations  37:11 - What is Mem.ai?  51:04 - Day to Day Life of a Co-Founder  54:10 - Securing a Seed Round from Andreessen Horowitz 1:01:07 - Biggest Influences 1:04:02 - Philosophy on Wealth Creation 1:08:39 - Lightning Round

Episode 67 is with Raad Ahmed, Founder & CEO of LawTrades! LawTrades is pioneering a new work model that economically empowers independent legal professionals to monetize their skills, while helping companies build distributed legal teams. General Counsels have access to a highly selective talent network of attorneys, paralegals, compliance, and legal ops, to complement their own legal department and company culture. We talk with Raad about his early music passions and influences to entrepreneurship. He details his journey from first discovering the internet to making 6-figures in online ad revenue while in law school. Raad also details his mission to achieve a utopian work-life balance through LawTrades, and how they successfully raised $6M at an $80M valuation using just a link and without pitching to VCs. This was a great conversation that weaves through career, life, and philosophy that we hope you enjoy! LawTrades https://www.lawtrades.com/ Timestamps 3:05 - Passions & Influences 10:02 - “Passionately curious, but compulsively minimalist.” 18:34 - Challenges of Raising Capital 22:05 - How Justin Khan almost ruined LegalTrades 27:00 - How LegalTrades raised a $6M Series A with their customers 36:11 - VC Funding vs. RUV Funding 43:43 - What is LawTrades & What problem are they solving? 51:34 - Pros & Cons of Legal-Tech Industry 58:34 - Defining & Measuring Success 1:06:00 - Impact of the Founding Team 1:12:38 - Wealth Creation 1:20:36 - How Schooling Needs to Change 1:32:00 - Lightning Round

Episode 66 is with Maika Isogawa, Co-Founder and CEO at Webacy! Webacy helps protect your digital legacy by allowing you to decide what you want to do with your digital life after you die. This includes your social media accounts blockchain-based assets, cryptocurrencies and other assets. Some of this involves deletion or memorialization of accounts, posting final, sequenced content, and transferring crypto or business accounts to your inner circle. Maika is a former professional acrobat and performer for the Cirque Du Soleil brand of shows. She is also a Stanford '20 alumnus with a special concentration in Symbolic Systems, a program which combines the study of Human Computer Interaction, Software Engineering, Linguistics, Philosophy, and more. Maika was most recently a Cybersecurity Engineer for Microsoft, while Maika and Webacy have been recently recognized as a member of the Forbes 30 Under 30 list. We sit down with Maika to discuss her early days with the Cirque du Soleil and how she became an entrepreneur. She details how she battles imposter syndrome, cultural influences in her life, including Anime, and how Webacy is securing digital assets for the world of tomorrow. This was a fun chat that we hope you enjoy! Webacy https://www.webacy.com/ Timestamps  2:30 - Circus Acrobatics at Cirque du Soleil  8:00 - Overcoming Fear & Imposter Syndrome 10:25 - Importance of Hobbies & Side Hustles 13:10 - Influence of Culture 17:00 - Anime Culture 19:50 - Goal Setting for Success 24:40 - Pressure to Succeed 28:18 - Happiness & Success 31:00 - The story behind Webacy 33:14 - Crypto scam that stole from Maika 35:30 - Challenges of Crypto-adoption 38:50 - Defining Company Culture 42:37 - Webacy’s Founding Team 45:37 - Managing Differing Opinions 49:04 - Advice for new entrepreneurs 50:05 - Lightning Round

Episode 65 is with Harsehaj Dhami and Samantha Ouyang, two International Baccalaureate high school students based in Toronto. Harsehaj is an impact driven student working to bridge the healthcare access gap to low income families and those struggling with their mental health. She is currently helping build a health startup based out of San Francisco that has just raised their seed-round. In her personal projects, she’s working on modelling CNN (convolutional neural networks) that uses brain EEG scans to diagnose depression. Samantha is a goal oriented student, passionate about using STEM, design, engineering and innovation to create lasting change in the world. Having started off in competitive programming at an early age, her experiences led her to founding, Superposition Toronto, a non-profit that helps to bridge the gender gap in STEM. Samantha and Harsehaj have both crossed paths in The Knowledge Society - where cohorts of students are encouraged to solve the world’s biggest problems using emerging technologies. They have both previously worked together on a project focussed on removing chemical pollutants from drinking water. We talk to Harsehaj and Samantha about their respective journeys in the tech space, the various differences in education and culture between generations, the influence of asian households, and much more. This was such an insightful conversation that brought to light the various evolutions of education, life, culture, and tech through the years. We hope you enjoy! Timestamps  2:45 - Harsehaj Intro & background  6:45 - Samantha Intro & background 11:25 - Early Lessons from their experiences 18:58 - Cultural Influences of an Asian household 27:14 - How can schools encourage more innovation? 30:30 - Challenges of Women in Tech 37:30 - Social Pressures on Millennials & Gen Z 44:42 - Pros/Cons of Social Media for Gen Z 53:19 - Increasing Cost & Competition in Schooling 1:00:12 - What is the current tech focus for Gen Z? 1:03:39 - Lightning Round

Episode 64 is with Alexandra Nuth, Co-Founder and COO at Control HQ! Control HQ is a financial management tool for freelancers and flexible workers. The freedom and flexibility of self employment is coveted, but not the antiquated process of managing your money, from irregular pay to income taxes. Alexandra built her way up in corporate strategy before teaming up with two colleagues on this venture to become the financial management company for independents. We talk to Alex about her move from corporate to entrepreneurship, the future of flexible work and why ControlHQ is so important in this space, the importance of mentorship, and so much more. This was such an insightful conversation that we hope you enjoy! Control HQ https://www.controlhq.com/ Timestamps 1:43 - Intro & Background 4:56 - Transitioning from Corporate to Entrepreneurship 8:50 - Important Core Values 10:57 - Building Company Culture 15:06 - Importance of Mentorship 21:40 - What is Control HQ? 24:29 - What makes Control HQ different? 28:30 - Importance of Diversity & Inclusion 38:40 - Lightning Round

Episode 63 is with Lloyed Lobo, Co-Founder and President of Boast A.I. Boast A.I helps companies access the billions of dollars available in R&D tax credits and funding to improve insights and grow faster. Their software integrates financial, engineering, and project data to increase the speed, accuracy, and size of eligible tax incentives. In other words, Boast helps you maximize claims and innovate faster while you run your business. Lloyed is an entrepreneur through and through, with a never ending desire to keep moving, building, and hustling. We talk to Lloyed about his journey in tech, how being a refugee of the Gulf War in Kuwait shaped his mentality on life, and the plethora of lessons he’s gathered through his experiences thus far. This was an insightful and candid conversation that you hope you enjoy! Timestamps  2:01 - Background  9:00 - Engineering Uncertainty (for Success) 16:25 - Managing Mental Health 26:43 - Importance of your Network 30:14 - The CAMPER Framework 33:00 - What is Boast A.I? 35:08 - How Boast A.I helps businesses with R&D Credits 38:04 - The Future of Boast A.I 39:51 - Raising $100M from Investors 51:51 - Advice to Founders 53:02 - Lightning Round

Episode 62 is with Brice Scheschuk, Co-Founder of WIND Mobile (now known as Freedom Mobile) and currently the Managing Partner at Globalive Capital. The telecom space is one of the most regulated and red-tape ruled industries to work within, making Wind Mobile’s story an incredible achievement. Brice led the Finance, HR, Procurement and Supply Chain functions of one of the largest new entrant pure play wireless services providers and helped raised approximately $2B in capital to acquire spectrum and operate the WIND network. Now, he manages a $100M investment firm in Globalive focusing on representative private equity, real estate, and venture investments. We talk to Brice about his journey breaking into the Canadian telecom space, the evolution of entrepreneurship through different eras, and impactful skills necessary for anyone looking to achieve success. He also explains the importance of mentorship and how he’s helping the next generation through MindFrame Connect. This was an incredible informative episode that we hope you enjoy! Timestamps 2:20 - Background and Education 5:30 - The Entrepreneurship Journey & Mindset 11:30 - Transferrable Skills through Generations 15:55 - Founding WIND Mobile 23:00 - Advice on Seeking Investors 30:52 - Assessing & Managing Risk in Life 38:25 - What is Anti-Fragility? 47:30 - Decision Making & Regret 56:55 - MindFrame Connect 01:02:50 - Lightning Round

Episode 61 is with Ben Share, Co-Founder and CEO at Dime! Dime helps turn your content into genuine digital collectibles for your followers to buy, sell, trade and collect. While NFTs have the potential to transform the way we create art and use the internet, we still need a system in place that's powerful enough and clear enough for everyone to use. Dime is the first NFT marketplace to not require a crypto wallet, the first to transact purely in $USD, and most importantly, the first marketplace that ordinary people will want to use. We talk to Ben about the utility of NFTs, the Blockchain and Web 3.0. We discuss the future of these technologies and how creators will be significantly impacted by advancements in this space. He details his journey founding Dime and what the internet of tomorrow will look like as the foundations are laid today.  If you’re looking to stay ahead of the next big shift on the internet, this episode is a must! Timestamps 2:15 - Intro to Ben 4:54 - What is Web 3.0? 6:28 - Significance of Blockchain 8:11 - What is an NFT? Why are they important? 15:47 - Importance of Community 19:05 - What is a Rug Pull? 22:10 - NFT Investing: How To 26:44 - What is Dime? 28:37 - How Dime helps purchase NFTs 31:22 - How NFTs and Web 3.0 will help creators 35:12 - Challenges in & Advice for the Web 3.0 and NFT space 39:38 - The Y Combinator Experience 45:54 - Lightning Round

Episode 60 is with Kris Bennatti, Co-Founder, CEO and Lead Developer at Bedrock AI! Bedrock AI are experts and innovators in the adaptation of language models to financial text that facilitate a unique, quantamental approach to reading and understanding SEC filings. In other words, they use underused, unstructured data sources to understand and predict earnings management, accounting problems and outright fraud. We talk to Kris about her journey from accounting as a CPA to founding Bedrock AI. She details the importance of machine learning in the financial markets and how investors and companies alike can benefit from its use. This was an incredibly insightful conversation that we hope you enjoy! Timestamps 2:50 - Career Journey from CPA to Coding 7:40 - Advice to newcomers to Data Science 10:04 - Machine Learning vs. Artificial Intelligence 13:16 - Deep Learning Based Language Models 17:45 - "AI is inherently biased." 22:00 - The Concept of Singularity 24:17 - What is Bedrock AI? 28:59 - Example of how Bedrock AI helps investors 35:28 - The future of Bedrock AI 39:16 - Finding the right Business Partners 41:36 - Challenges of being a Founder 45:20 - Lightning Round