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 Landscape
06:44 Deep Dive into NewView Capital
15:02 The Art of Networking in Venture Capital
19:53 Capital Allocation: The Underrated Skill of Top CEOs
22:11 Mentorship and Learning from the Best
23:25 Reflecting on the Venture Ecosystem: OpenView's Dissolution
24:30 The Anatomy of VC Fund Failures
28:52 Exploring Promising and Challenging Industries
33:43 Personal Insights on Work-Life Balance
40:40 Reflections on Career Choices and Regrets
45:45 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

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!

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-making, the value of faith in overcoming challenges, and the mentorship and learning opportunities at SUSA Ventures. Join us for an insightful conversation on competition, risk, and personal growth in the world of startups and investing.

[00:04:47] Professional poker career

[00:07:39] Competition and mamba mentality.

[00:11:26] Understanding players' strategies in poker.

[00:12:01] People's core being expressed.

[00:16:02] Power of intuition in decisions.

[00:19:06] EV in real life decision-making.

[00:21:35] Overcoming financial and personal challenges.

[00:27:41] Faith and community in career.

[00:31:15] Creating the kingdom of heaven.

[00:35:07] Web3 and its future.

[00:37:14] Control in decentralized finance.

[00:40:35] Regional banks and startup ecosystem.

[00:44:09] Humans are meant to create.

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.

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