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]

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

Timestamps

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

Timestamps

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

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

Timestamps

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

Timestamps

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

Timestamps

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

Timestamps