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Learn how to tackle a life with multiple jobs and projects. Hear Molly Ford Beck, a member of the side hustle generation, interview guests who are climbing the ladder of corporate success and managing an entrepreneurial venture on top of their day jobs. If you have a side hustle, want to start a side hustle, or just want to hear some good advice, this is the podcast for you.
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In this podcast episode, we sit down with Brendon Redlinger VP of Marketing at Chili Piper. Brendan shares insights from his early career, moving from sales to marketing, and delves into the nuances of being a fractional leader. We cover the importance of understanding one's path to tech, embracing growth hacking, and the value of fractional leader…
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Have you ever considered what keeps customers coming back for more? Megan Yen, VP of Customer Success and Activation at Ramp, joins us to unravel the secrets behind building a thriving customer success department. With her extensive background transitioning from management consulting to the tech world, Megan brings a unique perspective on fostering…
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In this episode, our guest is Christina from NewView Capital, where she shares her journey into the world of tech and venture capital, moving from investment banking to major roles at Google and Atomico before joining NewView. Christina discusses her experiences living and working in various cities worldwide and offers insights into the cultural nu…
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This episode features CJ Gustafson, the CFO of PartsTech and founder of the popular finance blog Mostly Metrics. He started his career in PE eventually wanting a bigger challenge, helping him land a role at a startup. Now as CFO, he describes the day to day and what it means to be the right hand person to the CEO. In this episode, we cover topics s…
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Casey Woo is a seasoned multi-stage operator and 7x CFO with over two decades of experience in business operations and finance from investment banking on Wall Street to Silicon Valley tech start-ups. Casey now leads 700+ CFOs, COOs, and Biz Ops company builders as the co-founder of Operators Guild, a community for professionals in strategic finance…
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This podcast features an interview with Charlie, Head of Marketing at Finch. Charlie shares his background growing up in the Bay area and being exposed to technology from a young age. He reflects on the challenges of entering the tech industry in 2010 and compares it to the current landscape. In this episode, we discuss how the marketing leader has…
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We sat down with Grace Ge, Principal at Menlo Ventures. Growing up in a small town in Texas, she was inspired by her father's involvement in robotics and tech, eventually catapulting her into a career in VC. In this episode, she shares her thoughts on the flaws of the current partnership model in VC firms and how VC remains largely a solo sport. Gr…
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In this episode, we dive into the fascinating journey of Pratyush Buddiga, a former professional poker player turned senior associate at SUSA Ventures. Pratyush shares his experiences of being ranked second in the world in professional poker, the highs and lows of his career, and how he transitioned into the world of tech and venture capital. We al…
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Zain, a principal at Ridge Ventures, talks about his journey into the tech industry and his transition to becoming a venture capitalist. He discusses the opportunities and challenges in the industry, including the impact of big tech companies. We delve into the crucial skills required for successful investors in venture capital, emphasizing the sig…
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On the 100th episode of the Generation Hustle podcast, Andrew shares his perspective on the pressures and misconceptions surrounding entrepreneurship. He warns against the obsession with big numbers and external validation, which can lead to a skewed perception of what it takes to succeed in business. Andrew also reflects on his own upbringing and …
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In this fascinating episode, I had the pleasure of talking with Carla Matheson, a true trailblazer in the world of finance and a visionary leader. Carla shares her journey from working as a nanny for an entrepreneurial family to becoming the CFO of Tiny Capital and the impact of technology on the finance function. We discuss how her early experienc…
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How did Geoff Charles, VP of Product at Ramp, go from a background in consulting and finance to revolutionizing the world of product management in tech? In this fascinating conversation, we discuss the evolution of product roles, the importance of collaboration, and prioritizing value creation. We dive deep into Geoff's role at Ramp, the critical a…
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Lucy Guo shares her personal journey from a young hustler to co-founding Scale AI and Passes, emphasizing the importance of confidence and persistence in entrepreneurship. The episode also delves into co-founder dynamics, pivots, customer acquisition, and AI's impact on the economy. We also deep dive into Lucy's personal thoughts on how success imp…
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Episode 96 is with Kyle Harrison, General Partner at Contrary! In this episode, you will learn Contrary's investment approach, how storytelling drives the world, how to achieve investor-founder fit, and a particular trend amongst tech unicorns that Kyle refers to as “Thinning the Herd”. He also details the downstream impact of the current tech layo…
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Episode 95 is with Brian Hollins, Founder & Managing Partner at Collide Capital! In this episode, you will learn best practises on building meaningful relationships while networking, the importance of representation, the highs and lows of raising funds, and how to set yourself up for success out of school. Brian also touches on generational differe…
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Episode 94 is with Earnest Sweat! In this episode, you will learn how to provide value when building relationships, the three main problems faced by every industry, and the current economic outlook from the lens of a VC and that of a Founder. Previously as a venture partner at GreatPoint Ventures, Earnest focused on investments particularly within …
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Episode 93 is with Jason Shuman, General Partner at Primary Venture Partners! In this episode, you will learn how to calculate your business’ TAM, the difference between Portfolio impact and platform, how to pitch to an LP, and hire the best candidates. Jason also explains his outlook on the macro environment and how best to fundraise right now. At…
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Episode 92 is with Jordan Segall, Principal at Redpoint Ventures! In this episode, you will learn the differences between early and late stage investing, what makes a good market opportunity, the balancing act of the Investor-Founder relationship, and how Open AI and ChatGPT is going to change the future of work. Jordan also details his thoughts on…
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Episode 91 and the Season 3 opener is with Alessio Fanelli, Partner at Decibel VC! In this episode, you will learn about Decibel’s investment strategy, how they help early stage startups, and the future of data tools. Alessio also details his journey to Venture Capital, building tools for technical founders, dealing with imposter syndrome, and how …
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Episode 90 is with Amanda Robson, Partner at Cowboy Ventures! Originally from Ancaster, Ontario, Amanda, better known as Robby, invests in B2B seed & pre-seed founders and focuses on innovations in developer tooling, data management, security, applied AI, and supply chain. In November 2020, she led a US$3.2-million investment round in a securities-…
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Episode 89 is with Rachel Star, Principal at Unusual Ventures! Unusual Ventures is an early-stage firm that invests in both enterprise and consumer startups. They lead pre-seed to Series A investments in software startups, supporting founders from idea to IPO, enabling startups with hands on support and expertise during their early journey. Rachel …
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Episode 88 is with Chris McCann, Co-Founder & Partner at Race Capital! Race Capital is an early stage venture capital fund that lead pre-seed and seed stage technology startups, interested in the enterprise/B2B space, especially anything within the infrastructure layers of the stack. The company prefers the seed stage because it allows for the grea…
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Episode 87 is with Hamzah Nassif, Parnter at Real Ventures! Real Ventures is an early-stage venture firm focused on serving daring entrepreneurs with the ambition to create successful, global companies. Since 2007, Real Ventures has dedicated itself to building the Canadian startup ecosystem on the belief that people, not money, build game-changing…
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Episode 86 is with Claire Rafson, Investor at Eniac Ventures! Based out of Eniac’s New York office, Claire is passionate about democratizing access to capital, making essential services like FinTech and health care more accessible, and embedding ESG (environmental, social, and governance) principles into companies. Eniac Ventures leads seed rounds …
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Episode 85 is with Sai Senthilkumar, Principal at Redpoint Ventures! Redpoint Ventures partners with visionary founders to create new markets or redefine existing ones. The firm invests in startups across the seed, early and growth phases. Since 1999, Redpoint has backed over 465 companies with 140 IPOs and M&As, including Netflix, Twilio, and Zend…
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Episode 84 is with Prateek Sanjay, Founder of Foundraisr! Prateek helps FinTech and SaaS startups to source angel investors through cold emailing, with his company, Foundraisr. His ability to create demand, build relationships and ultimately secure funding rounds for startups through cold outreaches have solidified his reputation as an expert in in…
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Episode 83 is with Neal Soni, Co-Founder of Prepared! Prepared is a start-up building technology to better connect citizens to the US emergency calling system. Currently, 911 call centres are technologically antiquated and unable to accept anything besides calls. Prepared’s services allow 911 dispatchers to send callers a text that connects them to…
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Episode 82 is with Elizabeth Yin, Co-Founder & General Partner at Hustle Fund! Hustle Fund makes pre-seed investments into the fastest-growing start-ups. With a team of former founders, Hustle Fund understands how amazing AND terrible startup life is and brings that authentic element to the table. Elizabeth Yin was a former partner at 500 Startups …
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Episode 81 is with Pablo Srugo, Partner at Mistral Venture Partners! Mistral is a seed to early stage venture capital firm that focuses on getting start-ups to Product-Market Fit. They look for investments that leverage the power of the internet to make businesses smarter. Pablo is a two-time founder, having first launched MyTutor.ca, a tutoring ma…
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Episode 80 is with Maëlle Gavet, CEO of Techstars! In June 2022, we attended the Collision Tech Conference in Toronto, Ontario, during which we had the opportunity to sit down with Maëlle for a personal chat. Maëlle Gavet is a French businesswoman, author, and entrepreneur who has been a leading tech executive for over 15 years. She has been named …
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Episode 79 is with Chris Neumann, General Partner at Panache Ventures. Panache Ventures is Canada's most active seed stage venture capital fund. The fund has a founders-first philosophy, a commitment to diversity and strategically co-invests with smart angel investors and seed stage funds. Chris has 18 years of experience in Silicon Valley as an en…
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Episode 78 is with Muhammad Lila, Founder & CEO of Goodable! Muhammad is an award-winning journalist, media founder, and strategist who leads multi-platform teams and creates content across all platforms. He specializes in taking complex subject matter and distilling it into easy-to-understand content that is designed to create impact. Muhammad hol…
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Episode 77 is with Markell Baldwin, Partner at Drive Capital! Markell is a former Staff Electronic Design Engineer at Tesla with demonstrated experience in product development, sensor technology from a microcontroller level to the system level, and systems integration. At Drive Capital, he focuses on finding market defining companies in mobility, s…
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Episode 76 is with Ashley Francisco, Head of Startup Developer Ecosystems for Google Canada! In her role, Ashley manages Google Canada's Accelerator programs, scaled startup ecosystem events, and Canadian partner engagement. Her goal is to bring the best of Google's people, programs, products and technology to startup teams across the country. Ashl…
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Episode 75 is with Jesse Abrams, Co-Founder & CEO of Homewise! Recently distinguished by NEXT Canada as “The W. Galen Weston Top Entrepreneur”, by the American Marketing Association Hall of Legends as one of Canada's top 5 "Marketers on the Rise" and by Marketing Magazine as a "Top 30 Under 30" Marketer in Canada, Jesse is an accomplished business …
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Episode 74 is with Nicole DeTommaso, Senior Associate at Harlem Capital! As a Senior Associate at Harlem Capital, Nicole focuses on deal sourcing, due diligence, and platform development. Prior to Harlem Capital, Nicole worked at RBC Capital Markets within the Investment Banking division, focused primarily on Mergers & Acquisitions and Initial Publ…
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Episode 73 is with Jess Chan, Founder & CEO at Longplay Brands! Longplay Brands is a marketing agency working with B2C e-commerce brands in the health, wellness, and lifestyle spaces. The company M.O. is to work with businesses who are in it for the longplay - brands who are looking to create a legacy, build a lasting brand, and impact real lives. …
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Episode 72 is with Leigh Marie Braswell, Principal at Founders Fund! Before joining Founders Fund, Leigh Marie was an early engineer & the first product manager at Scale AI, where she originally built & later led product development for the LiDAR/3D annotation products, used by many autonomous vehicles, robots, and AR/VR companies. She also has don…
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Episode 71 is with Peter Zhou, Co-Founder & CEO of Rutter! Rutter is building a universal API for e-commerce platforms. The e-commerce market is split across hundreds of platforms, such as Shopify, Squarespace, Amazon, and others. Each of these platforms has its own app store or its equivalent. Rutter is an integration layer letting any e-commerce …
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Episode 70 is with Adit Gupta, Co-Founder & CEO of Lula! Lula is an institutionally backed delivery tech company, that helps stores by providing an all-encompassing platform that connects the world to them. They provide stores (convenience, liquor, pet, and more) the specialized technology, data, and customer success these merchants need to serve c…
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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…
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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 f…
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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 le…
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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 account…
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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 Francisc…
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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 be…
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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 othe…
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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 Chai…
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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 us…
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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 pre…
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