The Generation Hustle Podcast

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]

In this engaging conversation, Lucy Guo, a visionary entrepreneur and co-founder of Scale AI, shares her inspiring journey from hustler to tech leader. She discusses the pivotal moments of launching Scale AI, the importance of confidence and authenticity, and the dynamics of co-founder relationships. Lucy emphasizes how AI is reshaping the economy and offers insights into effective hiring for startups. She reflects on success, privilege, and her biggest regret, all while encouraging creators to check out her platform, Passes.

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