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 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

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.

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.

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 the corporate world to the tech startup scene.

Carla and I explore the challenges faced by Canadian tech companies, the skills and responsibilities of a startup CFO, and the importance of effective incentives for startups. We also discuss the evolving role of the CFO in the age of artificial intelligence and the complexities of navigating VC and PE investments for early-stage companies.

Finally, we delve into the world of board member communication and the importance of objectivity and critical thinking during times of disagreement. We share our personal definitions of happiness and how it can be applied to our work and lives. Don't miss this insightful conversation with Carla Matheson as we uncover the secrets to success in finance and tech.

(0:01:30) - Finance Journey

(0:08:41) - Startup CFO Qualities & Responsibilities

(0:16:26) - Effective Incentives for Startups

(0:20:10) - Sales and AI in Finance

(0:33:40) - Navigating VC and PE Investments

(0:37:13) - Investing Challenges for Early-Stage Companies

(0:48:27) - Board Member Communication and Disagreements

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, and his approach to making decisions that drive the company forward. Geoff also shares insights on building a successful company, including understanding the Total Addressable Market, tailoring the product playbook to the specific business, and designing a product that leverages top engineering talent.

Finally, we explore the world of AI in product management, the importance of data privacy, and how technology can be used as a tool to empower people.

Timestamps:

Geoff Charles' Background and Transition to Product Management [00:02:45]

The Role of Product Management [00:13:36]

Prioritizing Relationships with Engineers [00:15:25]

Challenging TAM [00:21:08]

User Experience at Ramp [00:28:29]

Ramp's Target Market and Differentiation [00:34:02]

Biggest Mistake at Ramp [00:40:30]

Fear Mongering and AI [00:46:42]

Cultivating Happiness [00:49:37]

Lightning Round [00:51:34]

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 and sharing her thoughts on folks who come from privilege.

If you are a creator check Passes out - https://www.passes.com/

Timestamps

Lucy's journey in the startup space [00:02:35]

Minimum Viable Product [00:07:28]

Confidence in Success [00:10:10]

How Scale AI started [00:13:35]

Landing the first customer [00:17:29]

Building Passes [00:22:23]

Qualities and skills for early-stage startup hiring [00:26:44]

AI's impact on innovation and the economy [00:30:54]

Authenticity and Polarizing Personality [00:36:13]

Emotions in Business Decisions [00:38:57]

Success and Guilt [00:45:36]

Success at a young age [00:47:51]

Lightning round [00:50:24-00:52:39]

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' podcast - 20VC.

Kyle is one of the most prominent writers in the venture space today, sharing his thoughts at his blog, Investing 101 2.0. Before joining Contrary, Kyle worked in some of the best names in VC, from TCV to Coatue to Index. Through all of these experiences, Kyle has led or participated in investments including Ramp, Pave, Anduril, Gitlab, Databricks and Snowflake to name a few.

Contrary
https://contrary.com/

Timestamps
2:12 - Intro to Kyle
7:13 - Storytelling drives the World
9:18 - What makes a good investor?
13:45 - Achieving "Investor-Founder Fit"
17:57 - Contrary's Investment Approach
21:47 - What is one contrarian opinion?
25:30 - “Thinning the Herd”
31:50 - Advice for Managing a Down Round
36:15 - Downstream Impact of Tech Layoffs
48:10 - 20VC with Harry Stebbings
51:35 - Proudest Moment & Biggest Regret
54:45 - Lightning Round

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 Consumer Software. More on that later.

Prior to Collide Capital, Brian spent six years working at Goldman Sachs across investment management, investment banking, and merchant banking. He is also a founding board member of BLCK VC, the largest black investor community in the US.

Born and raised in DC, Brian received his undergrad from Stanford U and his MBA from Harvard Business School.

Collide Capital
https://www.collidecap.com/

Timestamps
2:00 - Path to VC
5:54 - Investment Banking @ Goldman Sachs
10:00 - Transactional Relationships
12:30 - Sibling Relationships
17:35 - Collide Capital
22:30 - Choosing Your Business Partner
25:30 - Importance of Representation
31:14 - Audience Question - Highs and Lows of Fundraising
40:53 - Advice for Emerging Managers/GPs
43:45 - Venture vs. Building
50:30 - Gen Z Minded Consumer Software
54:10 - Pride & Regret
57:20 - Lightning Round

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 Environment, and IT & Data Infrastructures. Prior to GreatPoint, Earnest was a founding member at Prologis Ventures, the venture arm of the world’s largest industrial real estate owner. Earnest is an alum of Columbia University and earned his MBA from Northwestern’s Kellogg School of Management.

Timestamps
2:05 - Intro & Background
12:22 - Breaking into VC
28:40 - Investment Thesis
29:45 - Three Main Problems of Every Industry
36:20 - Unpopular Investment Belief
44:00 - Economic Outlook from the POV of VC
49:40 - Economic Outlook from the POV of Founders
57:00 - Building Relationships & Providing Value
1:00:20 - Lightning Round

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 including consumer healthcare, fintech, and marketplaces. The Boston native and University of Miami alum has jumped between sides of the table over the last eight years but started his career as the Founder of a D2C footwear company.

Forbes featured him on the 30 Under 30 in Venture Capital list; Venture Capital Journal named him one of Venture Capital's 40 rising stars.

Primary Venture Partners
https://www.primary.vc/

Timestamps
 2:05 - Intro to Jason
 4:00 - DTC Sneaker Business
 6:35 - Foray into Venture Capital
 8:15 - Primary Venture Partners
 9:46 - Portfolio Impact vs. Platform
12:09 - Calculating TAM
18:39 - Best Advice for Fundraising
21:04 - Biggest Fundraising Mistakes
24:50 - Hot Take - “Hire Based on Childhood, not Investment Thesis”
28:10 - Defining a Good Investor
30:35 - Macro-Economic Outlook
35:35 - How to Pitch to an LP
45:20 - Company Valuations
51:57 - Lightning Round

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 industry. 

At Redpoint, Jordan has made investments into Cyberhaven, Heartex, Dagger, and Railway. Prior to that, he brings a wealth of experience ranging from McKinsey & Co., Palantir Technologies, SalesforceIQ, C3, and Unusual Ventures. Jordan attended Stanford University from where he holds an MS in Management Science & Engineering. 

Redpoint Ventures
https://www.redpoint.com/

Timestamps
 1:40 - Intro
 6:35 - Redpoint Ventures
 8:46 - Early Stage vs. Later Stage Investing
10:28 - What Makes a Good Market Opportunity?
11:48 - Investment Case Study - Railway.app
14:14 - Biggest Challenge as a VC
17:15 - The Investor-Founder Relationship
20:00 - Providing Candid Feedback to Founders
25:24 - Macro-economic Environment - Fundraising advice
31:58 - Open AI & ChatGPT
34:32 - Hypetrains in A.I.
37:40 - Lightning Round

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 Decibel, Alessio was a Principal at 645 Ventures, where he helped lead investments in dev tools, security, and enterprise SaaS. His investments included Cube Dev, Panther Labs, Launchable, Oort, and Bigeye, amongst others. He works with founders on everything from product design to helping with recruiting technical talent.

Earlier in his career, Alessio was the founder of Smart Torvy, an open source & hardware home automation platform, and was a lead engineer at early-stage startups such as Welcome Tech. He’s still active in the open-source community as well.

Decibel Partners
https://www.decibel.vc/

Timestamps
 1:45 - Intro
5:07 - Becoming a VC
10:07 - VC Focus - Aggregators vs Specialists
13:45 - Evaluating Early Stage investments
18:20 - Most Difficult Part of Being a VC
21:29 - Imposter Syndrome in VC
25:29 - Future of Data Tools - Provide Value
29:19 - Data Security
33:03 - Data Security Companies to Watch
34:55 - Macro-Economic Outlook
41:20 - How to Communicate Lay-offs
45:00 - Transferrable Skills from Gaming
47:35 - Most Memorable Moment
55:15 - Lightning Round

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 billion.

When she’s not crushing it as a newly minted and youngest partner at Cowboy Ventures, she’s running her organization, Modern Angels, which seeks to democratize funding for women and non-binary people. She also co-hosts her own podcast, The Open Source Startup Podcast.

Cowboy Ventures is a seed-stage focused fund investing in digital startups that seeks to back exceptional founders who are building products that re-imagine work and personal life in large and growing markets.

We sit down to speak with Robby about her career journey from Ontario to Silicon Valley. She details the tech landscape across North America, the importance of DEI, why she’s big on Open Source, the art of cold outreach, and much more.

Cowboy Ventures
https://www.cowboy.vc/index

Timestamps
2:45 - Intro
5:24 - Importance of Cold Outreach
9:57 - Tech Industry - Canada vs. USA
12:32 - Amanda “Robby” Robson
15:59 - Joining Cowboy Ventures
18:25 - Cowboy Ventures Investment Thesis
25:17 - What Makes a Successful Founder
28:00 - Common Hiring Mistakes Founders Make
29:40 - Importance of Diverse Teams
32:50 - What is Open Source? Why is it important?
41:50 - The Open Source Podcast
47:20 - Modern Angels
51:24 - Time Management
55:40 - Lightning Round