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 gaps. Brendan highlights his approach to marketing and growth in startups, emphasizing data-driven decision-making, strategic leadership, and the significance of brand and customer satisfaction. We also discuss the future of marketing in the context of AI and changing consumer behaviors. 02:42 The Shift to Fractional Leadership Roles 06:13 The Value of Diverse Experiences in Career Development 10:46 Defining Marketing vs. Growth in Startups 14:35 Leadership Qualities and Strategies in Startups 21:46 Insights on Metrics and Resource Allocation in Marketing 27:48 Exploring Marketing Metrics and Strategies 34:58 The Future of Marketing in the AI Era 43:09 Personal Insights and Philosophical Musings 48:19 Lightning Round: Quick-fire Questions

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 consumption-based business models. This episode peels back the layers of what makes for a successful customer journey, from the initial onboarding experience to the nuanced dance of keeping clients engaged over time. Whether you're a CS professional or curious about the inner workings of tech company growth, Megan's insights are invaluable in understanding the compelling world of Customer Success. 01:58 The Evolution of Megan's Career 04:09 The Importance of Customer Success in Business 05:37 Ramp's Culture and Success Factors 06:44 Evolving Role of Customer Success in Tech 08:49 Hiring for Customer Success: Skills and Qualities 11:54 Revenue Responsibility in Customer Success 13:18 Onboarding and Activation: Key to Customer Retention 15:56 Predictive Analytics and Leading Indicators 18:59 Cross-Functional Collaboration and the Pod Model 24:45 Early Day Struggles and Scaling Onboarding at Ramp 30:41 Addressing Churn: Strategies and Customer Understanding 33:54 The Importance of Credibility and Brand in Customer Retention 35:56 Embracing Innovation and AI in Customer Success 46:32 Lightning Round: Quickfire Questions

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 across different regions. Christina also talks about building relationships in VC, selecting sectors for investment, and offers her unique perspective on work-life balance and success. 03:51 Navigating the Global Tech Landscape06:44 Deep Dive into NewView Capital15:02 The Art of Networking in Venture Capital19:53 Capital Allocation: The Underrated Skill of Top CEOs22:11 Mentorship and Learning from the Best23:25 Reflecting on the Venture Ecosystem: OpenView's Dissolution24:30 The Anatomy of VC Fund Failures28:52 Exploring Promising and Challenging Industries33:43 Personal Insights on Work-Life Balance40:40 Reflections on Career Choices and Regrets45:45 Lightning Round: Quickfire Questions

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 mistakes made by startups - Forecasting in a hypergrowth company - The world of vanity metrics 00:03:00 Path to tech 00:07:52 The CFO role has evolved significantly. 00:10:49 Managing expectations in unpredictable startups. 00:16:37 Choose companies with growth potential. 00:20:02 Transparency and trust drive success. 00:24:06 Personalize and forecast for success. 00:30:20 Importance of cash flow forecasting 00:36:08 Metrics should be understandable, comparative, and be behavior-changing. 00:41:59 Avoid relying on vanity metrics. 00:46:02 Hiring within finance 00:51:32 Control of time equals happiness. 00:55:41 Stack your talents for success.

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 community makes a difference for start-ups and professionals. When he’s not working, Casey spends time in California’s Bay Area with his wife and three children. 00:02:30 Casey's path to tech 00:09:13 Career exploration leads to growth. 00:12:55 Trust your gut, not timelines. 00:19:23 Building a supportive community for operators. 00:23:25 Building a successful community requires authenticity, engagement, and generosity. 00:31:37 Syndicates enable angel investing opportunities. 00:38:09 Empowerment and accountability in leadership. 00:40:22 Let go and trust talented individuals. 00:49:48 Nurture meaningful relationships through community. 00:51:06 Invest time in meaningful relationships.

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 highlights the importance of setting a clear strategy that aligns with company direction and working closely with other teams. We also go into depth on hiring practices and pathway to CMO. 00:03:24 Marketing leaders drive revenue growth. 00:08:47 Pathway to becoming CMO: Gain diverse marketing experience. 00:11:27 Adapting to new roles is important. 00:19:58 AI is changing marketing roles. 00:21:43 Allocating marketing budgets requires strategic decision-making. 00:31:18. Metrics should be connected to revenue. 00:32:38 Connecting marketing to revenue is crucial. 00:41:16 Brand is important for talent. 00:44:49 Embrace adversity for personal growth. 00:49:02 Open to helping and connecting.

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 proactive sourcing and hustling to find the best companies, rather than relying solely on network and brand. We also deep dive into Ilan Frank's (VP Product at Airtable) framework on how to become enterprise-ready, as many companies tend to struggle with scale! 00:10:34 Career path: VC requires experience. 00:13:20 Partnerships in VC need improvement. 00:16:24 VC role has evolved, hyper-specialization. 00:22:01 Proactive sourcing and all-in partnership. 00:32:29 Enterprise readiness criteria: scale, security, compliance, administration, usability. 00:33:06 Importance of scalability in software. 00:41:54 Risks of AI concentration. 00:47:11 Importance of diversity in tech. 00:50:07 Importance of diversity in tech. 00:54:00 Lightning Round

Former professional poker player turned venture capitalist Pratyush Buddiga shares his journey, including his success in poker, the power of intuition in decision-making, overcoming challenges with faith and community, and the future of Web3. They also discuss the role of venture capitalists, the impact of technology on human rights and jobs, and the implications of AGI.

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 relationships and having empathy. Zain shares his thoughts on how being a venture capitalist goes beyond mere transactions and involves forming deep connections with founders. Overall, the episode underscores the significance of building strong personal relationships and possessing empathy as essential skills for successful investors in venture capital. These skills enable investors to truly understand individuals, aid in their growth, and make well-informed investment decisions based on genuine relationships and trust. 00:03:44 Transition from law to tech 00:07:48 Propensity for action and curiosity. 00:13:15 VC trend: Solo GPs emerging. 00:14:48 Venture trends shifting with COVID. 00:22:53 Importance of curiosity in venture. 00:24:06 Learning from mistakes is essential. 00:28:50 Founder qualities for success: special skills, unique storytelling, understanding their motivations. 00:33:37 Importance of building relationships 00:40:11 Secondary sales can benefit founders. 00:43:28 Twitter's evolution and impact 00:49:51 Potential risks of social platforms. 00:53:30 Being empathetic and connecting deeply. 00:58:00 Finding your voice and vulnerabilities.

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 led him to founding Acquire. We also talk about strategies needed to get your business acquired, how to scale as a bootstrapped founder and common mistakes founders make at an early stage 00:02:00 - Entrepreneurship is not about extremes. 00:08:18 - Building in public builds fans. 00:11:10 - Building trust through personal branding. 00:20:45 - Bootstrap success: distribution & payback. 00:21:50 - Bootstrap businesses need quick profitability. 00:28:04 - Brand as David, not Goliath. 00:35:26 - Make acquisitions more efficient. 00:39:28 - Celebrate small exit successes. 00:43:48 - Starting small is perfectly fine. 00:49:10 - The rise of startup marketplaces.