The Generation Hustle Podcast

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 leadership in organizational strategy and filling ga...

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 early customer activation and combating churn in...

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 nuances in communication and business practices acro...

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 such as: - The role of a CFO - Common financial mis...

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 and operations roles. He strongly believes that c...

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 evolved to be more focused on revenue. He highlig...

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. Grace also emphasizes the importance of proactiv...

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 also explore the importance of intuition in decision...

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 significance of building strong personal relationship...

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 how his early fascination with business ultimately...

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 experiences shaped her career and how she transitioned from...

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 aspects of product management in tech startups,...

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 impacts personal image, her biggest regret an...

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 layoffs as well as his experiences on Harry Stebbings'...

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 differences, with a term he refers to as Men Z Minded...

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 three areas: Commerce Infrastructure, the Built En...

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 Primary, Jason leads new consumer investments inc...

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 the macro environment and hype trains in the AI i...

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 gaming helps him be a better VC. Before Deci...

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-software company called Drata, now worth US$1...

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 is Principal at Unusual helping to build and suppo...

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 greatest impact, using a founders’ first, investor...

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 companies. Real Ventures manages $325 million acr...

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 in bold founders who use code to create transforma...

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 Zendesk. Currently, the firm manages $4 billion ac...