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The Generation Hustle Podcast

The Generation Hustle Podcast

By Generation H

Sharing the journeys of amazing hustlers making an impact in their industries.

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GHP #89 - VC #11 - Investing in the Future of Commerce with Rachel Star!

The Generation Hustle PodcastNov 10, 2022

GHP # 106 - OP #3 - The Role of CFO and Navigating Hyper Growth in Startup

GHP # 106 - OP #3 - The Role of CFO and Navigating Hyper Growth in Startup

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.

Oct 19, 202356:50
GHP #105 - Operator #2 - The Fragility of Fake Communities and Finding the Right Career Path with Casey Woo

GHP #105 - Operator #2 - The Fragility of Fake Communities and Finding the Right Career Path with Casey Woo

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.

Oct 11, 202352:44
GHP #104 - Operator #1 - How to Become a Great Marketing Leader in Today's Tech World with Charlie Liang

GHP #104 - Operator #1 - How to Become a Great Marketing Leader in Today's Tech World with Charlie Liang

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.

Oct 04, 202351:34
GHP #103 - VC #21 - Breaking the VC Partnership Model and How to Be Value Add with Grace Ge

GHP #103 - VC #21 - Breaking the VC Partnership Model and How to Be Value Add with Grace Ge

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

Sep 06, 202355:54
GHP #102 - VC #20 - From Poker Pro to Venture Capitalist: A Journey of Risk and Reward with Pratyush Buddiga

GHP #102 - VC #20 - From Poker Pro to Venture Capitalist: A Journey of Risk and Reward with Pratyush Buddiga

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.

Aug 09, 202347:52
GHP #101 - VC #19 - Building Relationships with Founders and Teams: A VC's Approach with Zain Rizavi

GHP #101 - VC #19 - Building Relationships with Founders and Teams: A VC's Approach with Zain Rizavi

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.

Jul 25, 202301:00:40
GHP #100 - Making it Easy To Get Your Business Acquired with Andrew Gazdecki

GHP #100 - Making it Easy To Get Your Business Acquired with Andrew Gazdecki

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.

Jun 21, 202354:13
GHP #99 - The Future of Finance with Carla Matheson

GHP #99 - The Future of Finance with Carla Matheson

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

Jun 14, 202301:00:48
GHP#98 - How Ramp Builds Product With Geoff Charles

GHP#98 - How Ramp Builds Product With Geoff Charles

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.


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]

Jun 01, 202352:54
GHP#97 - How I Helped Build a Unicorn and Learning How to Hire with Lucy Guo

GHP#97 - How I Helped Build a Unicorn and Learning How to Hire with Lucy Guo

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 -


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]

May 25, 202352:55
GHP #96 - VC #18 - Backing Bold Founders from Seed to Scale with Kyle Harrison!

GHP #96 - VC #18 - Backing Bold Founders from Seed to Scale with Kyle Harrison!

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.


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

Feb 28, 202357:42
GHP #95 - VC #17 - Investing in Great Companies at the Intersection of Communities with Brian Hollins!

GHP #95 - VC #17 - Investing in Great Companies at the Intersection of Communities with Brian Hollins!

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

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

Feb 22, 202301:00:38
GHP #94 - VC #16 - Supporting Revolutionary (Not Evolutionary) Ideas with Earnest Sweat!

GHP #94 - VC #16 - Supporting Revolutionary (Not Evolutionary) Ideas with Earnest Sweat!

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.

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

Feb 07, 202301:03:10
GHP #93 - VC #15 - Investing In What's Next with Jason Shuman!

GHP #93 - VC #15 - Investing In What's Next with Jason Shuman!

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

 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

Jan 30, 202354:09
GHP #92 - VC #14 - Backing Founders at the Earliest Stages of the Climb with Jordan Segall!

GHP #92 - VC #14 - Backing Founders at the Earliest Stages of the Climb with Jordan Segall!

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

 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 -
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

Jan 23, 202339:60
GHP #91 - VC #13 - Founders Investing in Founders with Alessio Fanelli!

GHP #91 - VC #13 - Founders Investing in Founders with Alessio Fanelli!

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

 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

Jan 17, 202357:05
GHP #90 - VC #12 - Empowering the Next Generational Founders with Amanda "Robby" Robson!

GHP #90 - VC #12 - Empowering the Next Generational Founders with Amanda "Robby" Robson!

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

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

Nov 16, 202257:52
GHP #89 - VC #11 - Investing in the Future of Commerce with Rachel Star!

GHP #89 - VC #11 - Investing in the Future of Commerce with Rachel Star!

Episode 89 is with Rachel Star, Principal at Unusual Ventures!

Unusual Ventures is an early-stage firm that invests in both enterprise and consumer startups. They lead pre-seed to Series A investments in software startups, supporting founders from idea to IPO, enabling startups with hands on support and expertise during their early journey.

Rachel is Principal at Unusual helping to build and support the firm’s consumer investments. With a passion for products and people, she started her career as a consultant with McKinsey & Company with a focus on consumer brands, retailers, supply chain, and manufacturing.

Most recently, Rachel was an early-stage investor on the consumer team at Shasta Ventures. She has been a speaker at TED events, for the Aspen Institute, and at Autodesk University.

We chat with Rachel about her career journey from Consulting to VC. She details key learnings and transferrable skills, what makes a great mentor in this space, how to manage the stress of the job, and ultimately, how to become a VC. This was an insightful conversation that we hope you enjoy!

Unusual Ventures

2:30 - Intro to Rachel
4:55 - Transferrable Skills
7:28 - What Makes a Great Mentor
12:30 - Managing Pressure on the Job
14:27 - Key Learnings
18:18 - Should You Become a VC?
21:11 - Unusual Ventures
25:37 - Investment Criteria
31:57 - Understanding Your Business Needs
33:28 - Working @ Unusual Ventures
35:24 - Hiring @ Early Stage StartUps
45:55 - What Makes a Visionary?
49:35 - How to Become a VC
51:45 - Lightning Round

Nov 10, 202255:11
GHP #88 - VC #10 - Building Communities & Growing Start-Ups with Chris McCann!

GHP #88 - VC #10 - Building Communities & Growing Start-Ups with Chris McCann!

Episode 88 is with Chris McCann, Co-Founder & Partner at Race Capital!

Race Capital is an early stage venture capital fund that lead pre-seed and seed stage technology startups, interested in the enterprise/B2B space, especially anything within the infrastructure layers of the stack. The company prefers the seed stage because it allows for the greatest impact, using a founders’ first, investor second, approach.

Chris is the seed investor in Solana, FTX, Lightning Labs, Zeet, Notifi Network, and many other companies across Web3 and Web2.

Prior to Race Capital, Chris founded and led the community program at Greylock Partners and prior to that, he was the Co-Founder and CEO of Startup Digest – one of the earliest technology focused email newsletters – which he grew to +1M subscribers before being acquired by Techstars.

We talk to Chris about his journey in tech and venture capital. He explains the creation of Startup Digest, how he stumbled into VC, the importance of community, his early investments into bitcoin, Web 3.0 and much more. 

Race Capital

  2:55 - Intro to Chris
  6:11 - Chris’ Award-Winning Photography
13:00 - Creation of ‘Startup Digest’
19:50 - Working at Greylock (VC)
25:12 - What is “Community”?
33:32 - Learnings from Greylock
36:50 - Investing as an Angel vs. Investing as a VC
40:32 - Bitcoin and Ethereum
47:05 - Race Capital
51:30 - Securing an Equitable Deal
59:50 - Web 3.0
1:07:30 - Lightning Round

Nov 03, 202201:10:02
GHP #87 - VC #9 - Building the Canadian Start-Up Ecosystem with Hamzah Nassif!

GHP #87 - VC #9 - Building the Canadian Start-Up Ecosystem with Hamzah Nassif!

Episode 87 is with Hamzah Nassif, Parnter at Real Ventures!

Real Ventures is an early-stage venture firm focused on serving daring entrepreneurs with the ambition to create successful, global companies. Since 2007, Real Ventures has dedicated itself to building the Canadian startup ecosystem on the belief that people, not money, build game-changing companies. Real Ventures manages $325 million across five funds and its active portfolio of 100+ companies is currently valued at $10 billion.

An engineer first and investor second, Hamzah began his career working on Qualcomm’s first-generation multiprocessor chipsets in Boulder, Colorado. After 9 years of engineering study and work in the US, he moved halfway across the world to work with startups in the frontier and emerging markets of the Middle East.

We talk to Hamzah about his career journey thus far, from engineer to Partner. He details the Investment thesis of Real ventures, the day to day of a partner and board member, the importance and role of the board, and much more. 

Real Ventures

2:20 - Intro
12:50 - Defining Product-Market Fit
14:50 - It’s Ok To Be Wrong
17:30 - Convertible Notes & SAFEs - Pros & Cons
25:25 - Advice for Founders to Protect Themselves Financially
26:50 - How to Run a Tight Fundraising Process
28:00 - Why Do Boards Members Exist?
33:38 - Providing Feedback as a Board Member
35:50 - Guidelines for Board Members
38:10 - Day to Day of a Partner at Real Ventures
42:00 - Real Ventures
48:00 - Future Trends of A.I.
53:00 - Risks of Consolidated Power in Tech Companies
57:00 - Lightning Round

Oct 25, 202259:36
GHP #86 - VC #8 - Democratizing Access to Capital with Claire Rafson!

GHP #86 - VC #8 - Democratizing Access to Capital with Claire Rafson!

Episode 86 is with Claire Rafson, Investor at Eniac Ventures!

Based out of Eniac’s New York office, Claire is passionate about democratizing access to capital, making essential services like FinTech and health care more accessible, and embedding ESG (environmental, social, and governance) principles into companies.

Eniac Ventures leads seed rounds in bold founders who use code to create transformational companies. Armed with over 80 years of combined experience building their own companies, Eniac does more than just provide capital. They provide a platform through an expansive network with a strong belief in community at the heart of their investment approach.

We talk to Claire about her journey into VC. She details her day to day as an investor, what Eniac looks for in transformational founders, and how they’re pushing the bar on democratizing access to capital. 

Eniac Ventures

2:22 - Intro to Claire
8:00 - Mentorship & Representation
10:33 - Managing Mental Health
13:28 - Interviewing for Venture Opportunities
19:05 - Eniac Ventures
21:05 - Claire’s Day to Day
25:50 - What VC’s Look for in Founder Meetings
32:00 - Creating Strong Deal Flow
36:15 - Quantity vs. Quality
38:03 - “Lost Deals”
41:45 - Introverts vs. Extroverts in VC
43:45 - Democratizing Access to Capital
56:16 - Lightning Round

Oct 20, 202259:27
GHP #85 - VC #7 - Investing in Visionary Founders with Sai Senthilkumar!

GHP #85 - VC #7 - Investing in Visionary Founders with Sai Senthilkumar!

Episode 85 is with Sai Senthilkumar, Principal at Redpoint Ventures!

Redpoint Ventures partners with visionary founders to create new markets or redefine existing ones. The firm invests in startups across the seed, early and growth phases. Since 1999, Redpoint has backed over 465 companies with 140 IPOs and M&As, including Netflix, Twilio, and Zendesk. Currently, the firm manages $4 billion across multiple funds.

Sai is a Stanford University graduate and former Investment Banker turned VC focussed on growth investing. Pivoting his career from engineering and banking to VC, Sai looks for emerging companies and markets to support within infrastructure software.

We speak with Sai about his career thus far. He details the transferrable knowledge and networking skills he used to transition from IB to VC. He describes what makes an interesting market or company for investment, visionary founders and how to identify them, and the metrics and factors that go into a successful investment. 

Redpoint Ventures

2:30 - Intro to Sai
4:18 - Transferring Skills from IB to VC
5:20 - What Makes a Great Mentor?
7:45 - RedPoint Ventures
12:19 - Sai’s Day to Day
16:00 - What Makes a Market Interesting to Invest In?
17:17 - How to Invest in Developing Markets
20:55 - Investment Case Study - Monte Carlo
25:25 - Due Diligence Process at RedPoint
29:00 - Growth at All Costs Model
31:00 - Key Metrics for VC’s
33:20 - What makes a Visionary?
35:20 - How to Become a VC
37:25 - Lightning Round

Oct 11, 202239:54
GHP #84 - Mastering the Art of Cold Emailing with Prateek Sanjay!

GHP #84 - Mastering the Art of Cold Emailing with Prateek Sanjay!

Episode 84 is with Prateek Sanjay, Founder of Foundraisr!

Prateek helps FinTech and SaaS startups to source angel investors through cold emailing, with his company, Foundraisr.

His ability to create demand, build relationships and ultimately secure funding rounds for startups through cold outreaches have solidified his reputation as an expert in investor outreach.

We sit down with Prateek to talk learn how he created his six-figure business with no initial investment. He details his career journey, the Do's and Don’t's of email outreaches, and how he built his brand on LinkedIn that now consistently reaches millions every single day.


 2:00 - Intro to Prateek
 7:33 - Inbound vs Outbound Email Strategies for Growth
14:55 - Brand Building on LinkedIn
30:25 - How to Qualify Customers
34:00 - What NOT to do in Cold Emails
42:00 - How Prateek Helps Founders
47:30 - Thoughts on current VC/Startup Environment

Oct 06, 202252:14
GHP #83 - Saving Lives & Re-Inventing Emergency Services with Neal Soni!

GHP #83 - Saving Lives & Re-Inventing Emergency Services with Neal Soni!

Episode 83 is with Neal Soni, Co-Founder of Prepared!

Prepared is a start-up building technology to better connect citizens to the US emergency calling system. Currently, 911 call centres are technologically antiquated and unable to accept anything besides calls. Prepared’s services allow 911 dispatchers to send callers a text that connects them to a web app, where they can upload images, videos, GPS location, and even message back and forth.

Born out of personal experience - as Neal was a student in Westport schools during the 2012 Sandy Hook massacre - today over 30 cities have signed up for Prepared’s services to help keep schools and citizens safer.

We sit down with Neal to discuss the journey to building Prepared. He details the personal life experiences that led him and his co-founders to building on the idea, how Prepared is actively saving lives, issues with the emergency services infrastructure, and much more.


Neal Soni

 1:55 - Intro to Neil
 3:50 - Idea behind 'Prepared'
 6:40 - Issues with the Emergency Infrastructure
 8:50 - How 'Prepared' Works
11:50 - Building out the Founding Team
16:55 - Conflict Resolution in Teams
21:50 - Determining the Company Culture
23:05 - Hiring Engineers in Tech
31:49 - Buy vs. Build
34:29 - Work-Life-Balance
39:45 - Wealth Creation
43:53 - Lightning Round

Sep 28, 202246:48
GHP #82 - VC #6 - Democratize Wealth Through Entrepreneurship with Elizabeth Yin!

GHP #82 - VC #6 - Democratize Wealth Through Entrepreneurship with Elizabeth Yin!

Episode 82 is with Elizabeth Yin, Co-Founder & General Partner at Hustle Fund!

Hustle Fund makes pre-seed investments into the fastest-growing start-ups. With a team of former founders, Hustle Fund understands how amazing AND terrible startup life is and brings that authentic element to the table.

Elizabeth Yin was a former partner at 500 Startups where she invested in seed stage companies and ran the Mountain View accelerator. In a prior life, Elizabeth co-founded and ran an ad-tech company called LaunchBit (acq. 2014). Since then, she has reviewed over 20,000 startup pitches from around the world in the last few years and has helped numerous portfolio founders raise hundreds of millions of dollars.

She details her transition to venture capital from being a founder, what Hustle Fund stands for and looks for in founders and their companies, indicators of a good VC, dealing with investment regret, and much more!

Hustle Fund

Elizabeth Yin

 2:10 - A Day in the Life
 3:55 - Elizabeth’s Transition to Venture Capital
 8:40 - Indicators of a Good VC
13:20 - The Best Way to Become a VC
15:30 - The Changing VC Landscape
18:27 - The VC Model - Fundamentals
21:00 - What does Hustle Fund look for?
26:10 - Dealing with Investment Regret/FOMO
27:13 - Lightning Round

Sep 19, 202230:08
GHP #81 - VC #5 - Knowing When to Hold & When to Fold with Pablo Srugo!

GHP #81 - VC #5 - Knowing When to Hold & When to Fold with Pablo Srugo!

Episode 81 is with Pablo Srugo, Partner at Mistral Venture Partners!

Mistral is a seed to early stage venture capital firm that focuses on getting start-ups to Product-Market Fit. They look for investments that leverage the power of the internet to make businesses smarter.

Pablo is a two-time founder, having first launched, a tutoring marketplace for university students that was acquired in 2014. He later founded GymTrack, a VC backed startup in fit-tech that helped monitor equipment usage in gyms.

We talk to Pablo about his unique journey to venture capital. He highlights what they look for in founders and VC partners at Mistral, how they evaluate startups for investments, his thoughts on the growth of the Canadian VC space, and much more!

Mistral Venture Partners

 2:20 - Background - Founder Turned VC
13:00 - Transitioning from Founder to VC
16:10 - Advice for Founders working with VCs
22:33 - VC Deal Red-Flags
24:00 - What to look for in Founders
25:19 - “You want to have a pretty weak close rate.”
29:50 - Evaluating Passion
38:40 - Are we consolidating talent in Big Tech?
40:12 - Mistral Ventures
43:40 - VC Market - Canada vs. USA
50:38 - Building Relationships in VC
53:00 - How to Deal with FOMO
56:24 - Lightning Round

Sep 12, 202257:47
GHP #80 - Fostering Diversity & Empathy in Tech with Maëlle Gavet!

GHP #80 - Fostering Diversity & Empathy in Tech with Maëlle Gavet!

Episode 80 is with Maëlle Gavet, CEO of Techstars!

In June 2022, we attended the Collision Tech Conference in Toronto, Ontario, during which we had the opportunity to sit down with Maëlle for a personal chat.

Maëlle Gavet is a French businesswoman, author, and entrepreneur who has been a leading tech executive for over 15 years. She has been named to Fortune’s 40 Under 40 and Time’s Top 25 Female Techpreneurs’ among many other recognitions.

Her career has spanned across the globe from Principal at the Boston Consulting Group, CEO of OZON, Vice President of Operations at the Priceline Group, and now Techstars.

Techstars is a worldwide network helping entrepreneurs, founded on 3 simple ideas - entrepreneurs create the future, collaboration drives innovation, and great ideas can come from anywhere.

Since 2006, Techstars has invested in more than 3,000 companies and today has a market cap of $75 Billion.

We sit down with Maëlle to discuss her career journey thus far, and what made her choose her current role at Techstars. She highlights the differences in the tech landscape between North America and Europe, provides advice for early stage founders, and gives her perspective on the state of the industry and what needs to change.

Despite some background noise from the conference, this was a fun and informative conversation that we hope you enjoy!

Maëlle Gavet


 2:32 - Ikigai - Why Maëlle chose Techstars
 4:45 - TechStars - a Universal Investor
 7:40 - Advice for Early Stage Founders
12:54 - Current State of Diversity in Tech
15:24 - Trampled by Unicorns: Big Tech's Empathy Problem & How to Fix It
22:50 - “How do you want to be remembered?”

Aug 31, 202223:53
GHP #79 - VC #4 - Empowering Canadian Venture Capital with Chris Neumann!

GHP #79 - VC #4 - Empowering Canadian Venture Capital with Chris Neumann!

Episode 79 is with Chris Neumann, General Partner at Panache Ventures.

Panache Ventures is Canada's most active seed stage venture capital fund. The fund has a founders-first philosophy, a commitment to diversity and strategically co-invests with smart angel investors and seed stage funds.

Chris has 18 years of experience in Silicon Valley as an engineer, early startup employee, founder and investor. He helped build the world’s first 100 TB data warehouse, has invested in companies in more than 20 countries, and has mentored startups across 6 continents.

In this episode, Aman speaks to Chris about his journey from tech to VC. He details his fundraising experiences as a founder, his advisory methods now as a VC, and how Panache is pushing the Canadian tech ecosystem ahead.

Panache Ventures

Chris Neumann

 2:24 - Chris’ Background
13:43 - Tech Industry from 2000s to 2020s
17:20 - Chris’ Lumberjack Profile Pic
20:00 - Fundraising for a Data Start-Up
24:30 - Advisor vs Investor
25:50 - Challenges of Being a Founder
27:54 - Chris Critiques His Own Pitch Deck
33:44 - Best Advice for Founders
37:20 - Risk Tolerance is Relative
42:00 - Why Silicone Valley is so Unique
52:10 - How Panache Helps Companies & Founders
57:35 - Best Advice for Getting into VC

Aug 23, 202201:00:46
GHP #78 - Changing How Consumers Think of the News with Muhammad Lila!

GHP #78 - Changing How Consumers Think of the News with Muhammad Lila!

Episode 78 is with Muhammad Lila, Founder & CEO of Goodable!

Muhammad is an award-winning journalist, media founder, and strategist who leads multi-platform teams and creates content across all platforms. He specializes in taking complex subject matter and distilling it into easy-to-understand content that is designed to create impact. Muhammad holds a vast wealth of experience ranging from CNN, ABC, CBC, and now Goodable.

Goodable is one of the fastest growing news networks today. Using proprietary AI technology to search through thousands of news sources, the company identifies the best stories designed to make you happier and informed, all while avoiding negativity and the fear mongering we are accustomed to in news headlines.

Their tagline: "Give us Five Minutes, we’ll give you a whole new world!"

We sit down to speak with Muhammad about his career in journalism. He details his experiences in war zones, being targeted by ISIS and the Taliban with suicide bombers, how the newsroom and information landscape has changed over generations, and how Goodable is helping solve some of these problems we see today.

This was an incredibly profound conversation that touched on so many current and significant events that we hope you enjoy!


 3:08 - Deciding the News is Innately Difficult
 5:50 - Muhammad’s Background
 6:45 - Seeing Diverse Names in Journalism
 8:25 - “CBC Took a Risk on Me”
10:10 - How Toronto Culture helped Muhammad
15:19 - Meaning Behind Muhammad’s Name
18:12 - Full Circle Moments
19:45 - “Russians, Egyptians, ISIS & the Taliban all tried to kill me.”
21:17 - Muhammad’s Experience in Afghanistan
28:09 - Fear in Journalism
31:33 - Managing Emotions on the Job
34:24 - How the Ad-Revenue Model Destroyed News Media
39:53 - How Do We Fix Journalism?
43:14 - Who Decides the News?
48:05 - What is Goodable? How are they helping Journalism?
58:00 - The War on Freedom of Speech
01:08:06 - Why Donald Trump won the 2016 Election
01:10:31 - Social Media, Censorship & Human Behaviour
01:17:37 - Managing Mental Health
01:24:15 - Lightning Round

Aug 17, 202201:29:09
GHP #77 - VC #3 - Focussing on First Principles with Markell Baldwin!

GHP #77 - VC #3 - Focussing on First Principles with Markell Baldwin!

Episode 77 is with Markell Baldwin, Partner at Drive Capital!

Markell is a former Staff Electronic Design Engineer at Tesla with demonstrated experience in product development, sensor technology from a microcontroller level to the system level, and systems integration. At Drive Capital, he focuses on finding market defining companies in mobility, supply chain, and space.

We chat with Markell about his journey into tech, how minorities can break into tech, and important frameworks for continued growth and success in the industry. He also details his experience at Tesla and the future of Venture Capital. This was a really insightful convo that we hope you enjoy!

Drive Capital

 2:42 - Life-Changing Moments
 9:03 - Working at Tesla
10:50 - Bradley Beal on competition
14:10 - Framework - Exposure, Possibility, Attainability
22:55 - Breaking into Venture Capital
26:22 - Drive Capital
27:50 - First Principles
32:33 - Highlights & Lowlights of VC
37:40 - Future of Electrification
45:30 - What makes Elon Musk so successful?
52:30 - Impact of Diversity in VC
59:00 - Lightning Round

Aug 08, 202201:04:48
GHP #76 - Activating Canadian Startups through Google Accelerators with Ashley Francisco!

GHP #76 - Activating Canadian Startups through Google Accelerators with Ashley Francisco!

Episode 76 is with Ashley Francisco, Head of Startup Developer Ecosystems for Google Canada!

In her role, Ashley manages Google Canada's Accelerator programs, scaled startup ecosystem events, and Canadian partner engagement. Her goal is to bring the best of Google's people, programs, products and technology to startup teams across the country. Ashley is a professional marketer by trade with a diverse background in local and global brand building at Google, Visa, Mondelez and Kraft Foods.

We sit down to talk with Ashley about her path to tech and ultimately Google. She details how Google’s Accelerator Programs are preparing founders of today to be the leaders of tomorrow. She also describes how you can land a job at Google, women empowerment in the tech environment, and the future impact of the tech industry.

Google for Startups Accelerator

Google: Founder Fridays

Google for Startups Accelerator: Women Founders

Google for Startups Accelerator: Black Founders

 2:00 - Ashley’s Role at Google Canada
 3:05 - Landing a job at Google
 8:05 - Skills Required to Work at Google
15:40 - Overcoming Imposter Syndrome
19:50 - Google’s Startup Accelerator Program
27:14 - Startup Story - Paper Stack
31:52 - Building a powerful community
34:37 - The Future of Google’s Accelerator Program
36:14 - Women Empowerment in Tech
38:50 - Future Impact of the Tech industry
41:45 - Thought Leaders to Follow in the Tech Space
43:55 - Making Connections in the Tech Space
47:34 - Managing Mental Health
51:23 - Defining Success

Jul 23, 202255:39
GHP #75 - Building an End-to-End Home Ownership Experience with Jesse Abrams!

GHP #75 - Building an End-to-End Home Ownership Experience with Jesse Abrams!

Episode 75 is with Jesse Abrams, Co-Founder & CEO of Homewise!

Recently distinguished by NEXT Canada as “The W. Galen Weston Top Entrepreneur”, by the American Marketing Association Hall of Legends as one of Canada's top 5 "Marketers on the Rise" and by Marketing Magazine as a "Top 30 Under 30" Marketer in Canada, Jesse is an accomplished business leader, Digital Marketer and Advertiser. He has a passion for growing businesses and never settling for the status quo.

Homewise provides Canadians with a better mortgage process with a simple online application that uses human language, helpful content and access to tech-powered professionals at every step to get a great mortgage. Their goal is to get the best deal and save their customers the most money possible.

We talk to Jesse about his journey into entrepreneurship, how Homewise is disrupting the mortgage industry, the current state of the Canadian real estate market, and much more. This was a great conversation that we hope you enjoy!


  2:40 - Road to Entrepreneurship
  8:15 - Can Entrepreneurship be taught/learned?
 15:55 - Jesse’s Career Transition
 24:30 - Advice for new Entrepreneurs
 29:00 - The story of HomeWise and Early Growth
 34:45 - How HomeWise Simplifies the Mortgage Process
 42:29 - Building a Successful Team
 49:10 - Current State of the Canadian Real Estate Market
 56:16 - Should we stop blind bidding?
 59:09 - Advice for Entering the Housing Market
1:07:17 - Importance of Charity Initiatives
1:14:00 - Lightning Round

Jul 19, 202201:18:06
GHP #74 - VC #2 - Changing the Face of Entrepreneurship with Nicole DeTommaso!

GHP #74 - VC #2 - Changing the Face of Entrepreneurship with Nicole DeTommaso!

Episode 74 is with Nicole DeTommaso, Senior Associate at Harlem Capital!

As a Senior Associate at Harlem Capital, Nicole focuses on deal sourcing, due diligence, and platform development. Prior to Harlem Capital, Nicole worked at RBC Capital Markets within the Investment Banking division, focused primarily on Mergers & Acquisitions and Initial Public Offerings within the technology and digital media sectors.

Harlem Capital is a venture capital firm on a mission to change the face of entrepreneurship by investing in 1,000 diverse founders over the next 20 years. They invest post product, or what they call 'Early Seed', with a commitment to reserving specific capital for investments in minority and women founders.

We talk to Nicole about her journey into Venture Capital. She details the day in the life of a senior associate at Harlem Capital, the criteria and due diligence for investing into good companies, the future of the internet, how VC’s are preparing for future economic downturns, and much more.

If you're looking to get into the VC space, this conversation is a great start!

Harlem Capital

 2:07 - Intro to Nicole
 4:49 - Lived Experience of Being a Minority in VC
 8:45 - Importance of Mentorship along the way
10:53 - Working in Toronto
12:48 - Transitioning into Venture Capital
15:54 - Using Twitter to get into VC
18:03 - Nicole’s Pitch Deck when applying to Harlem Capital
24:15 - Working at Harlem Capital
27:10 - Why Web 3.0 is important
33:08 - A Day in the life of a Senior Associate at Harlem Capital
37:20 - How VC’s are Preparing for a Recession
44:18 - The Lack of Diversity in VC
51:12 - Advice for Maintaining Mental Health
54:23 - Lightning Round

Jul 06, 202257:15
GHP# 73 - Building Relationships at Scale through Email with Jess Chan!

GHP# 73 - Building Relationships at Scale through Email with Jess Chan!

Episode 73 is with Jess Chan, Founder & CEO at Longplay Brands!

Longplay Brands is a marketing agency working with B2C e-commerce brands in the health, wellness, and lifestyle spaces. The company M.O. is to work with businesses who are in it for the longplay - brands who are looking to create a legacy, build a lasting brand, and impact real lives. In other words, they build relationships at scale.

Prior to Longplay, Jess was the Chief Marketing Officer of BestSelf Co., a 7-figure e-commerce brand. Since founding Longplay, she has scaled it to over $1M in just 18 months working with DTC e-commerce brands from startup to 250M+ in revenue, and has grown to a fully distributed team of 20+ people.

We talk to Jess about her journey to entrepreneurship, how she scaled her company, why email marketing is still so important, and her advice on starting your own agency. She details what makes a good email campaign, how she deals with imposter syndrome in her day to day life, and her experiences with psychedelics. We hope you enjoy!

Longplay Brands

2:49 - Introduction to Jess
5:33 - Navigating Imposter Syndrome
7:29 - Shift from Corporate to Entrepreneurship
10:56 - Rejection, Failures, & Building Confidence
15:11 - The idea behind Longplay
16:54 - How Longplay helps businesses
18:38 - Why is Email so important?
21:14 - Do’s & Don’ts of a Good Email Marketing Campaign
24:07 - The Evolution of Email Marketing
30:31 - Key Drivers & Struggles of Scaling
38:35 - How to Make the right Hire
43:14 - Advice for building a Consultancy/Agency
46:13 - Happiness, Personal Development, & Self Reflection
52:55 - Networking & Establishing a Support System
55:50 - Psychedelic experiences
01:01:32 - Lightning Round

Jun 29, 202201:03:59
GHP #72 - VC #1 - Investing in Companies of the Future with Leigh Marie Braswell!

GHP #72 - VC #1 - Investing in Companies of the Future with Leigh Marie Braswell!

Episode 72 is with Leigh Marie Braswell, Principal at Founders Fund!

Before joining Founders Fund, Leigh Marie was an early engineer & the first product manager at Scale AI, where she originally built & later led product development for the LiDAR/3D annotation products, used by many autonomous vehicles, robots, and AR/VR companies. She also has done software development at Blend, machine learning at Google, and quantitative trading at Jane Street. Leigh Marie is originally from Alabama, graduated from MIT, and loves to play poker, run long distances, and scuba dive.

Founders Fund is a San Francisco-based venture capital firm that invests across all stages and sectors, with a portfolio that includes Airbnb, Lyft, Spotify, Stripe, and Oscar Health. Founders Fund was the first institutional investor in SpaceX and Palantir Technologies, and one of the earliest investors in Facebook. Founded in 2005 by Peter Thiel, the fund currently manages over $11B in aggregate capital.

We sit down to talk to Leigh Marie about her journey through to tech. She details what makes a company and its founder investment-worthy, the future of data and machine learning, and provides advice for early startups looking to grow. She also touches on the future of work, Elon Musk, Universal Basic Income, and much more. This was such an insightful conversation that we hope you enjoy!

Founders Fund

 2:43 - Leigh Marie’s Background
12:22 - Core Skills to be a VC
17:29 - What does it mean to “hustle”?
20:15 - The story of Founders Fund
23:11 - Advice for Building a Personal Brand
25:39 - Generalists vs. Specialists
27:15 - The Future of Data, A.I., & ML
32:28 - What Makes a Company Investment-Worthy
39:42 - Working with Peter Thiel
41:34 - Evaluating Start-Ups & Founders
46:39 - Learning from Failed Investments
49:44 - Missed Opportunities - Investment Regret
51:33 - Imposter Syndrome
53:10 - Elon Musk, A.I., & Universal Basic Income
55:29 - Advice for Protecting Future Job Security
58:13 - Lightning Round

Jun 20, 202201:01:23
GHP# 71 - Integrating Every Commerce, Accounting & Payments Platform with Peter Zhou!

GHP# 71 - Integrating Every Commerce, Accounting & Payments Platform with Peter Zhou!

Episode 71 is with Peter Zhou, Co-Founder & CEO of Rutter!

Rutter is building a universal API for e-commerce platforms. The e-commerce market is split across hundreds of platforms, such as Shopify, Squarespace, Amazon, and others. Each of these platforms has its own app store or its equivalent. Rutter is an integration layer letting any e-commerce tool build one integration to access any storefront or marketplace.

Peter attended Yale University before interning at Facebook as a Software Engineer prior to his entrepreneurial endeavours. We sit down to talk to Peter about his journey to founding Rutter, the mindset of a startup CEO, his tools to a successful fundraise and opportunities for wealth creation. This was an incredibly informative episode that we hope you enjoy!


 1:25 - Peter’s Background
 4:39 - The Need to Make an Impact
 6:20 - Cultural Influences
11:05 - How to Embrace Entrepreneurship
13:50 - Mindset of a CEO
16:10 - Importance of Receiving Feedback
18:30 - Biggest Challenge of Becoming a CEO
21:20 - Peter’s Journey
24:40 - Key Learnings of B2B Entrepreneurship
28:07 - Sell Before You Build
30:40 - TL;DR of Rutter
35:45 - Rutter’s Approach to Fundraising
39:35 - Common Errors Made During Fundraising
41:35 - Prioritizing Mental Health as a Founder
46:50 - Wealth Creation Opportunities of the Future
50:10 - Thoughts on the Wealth Gap Issue
51:24 - Lightning Round

Jun 13, 202254:45
GHP #70 - Bridging the Delivery Gap For Small Businesses with Adit Gupta!

GHP #70 - Bridging the Delivery Gap For Small Businesses with Adit Gupta!

Episode 70 is with Adit Gupta, Co-Founder & CEO of Lula!

Lula is an institutionally backed delivery tech company, that helps stores by providing an all-encompassing platform that connects the world to them. They provide stores (convenience, liquor, pet, and more) the specialized technology, data, and customer success these merchants need to serve customers. This united network of stores powered by Lula enables independents and small chains to compete with major corporations as the nation's largest retail delivery marketplace. Adit is a Ph.D. student at Drexel University, with research interests in Computer Vision, Artificial Intelligence, and Human Computer Interaction.

We sit down to talk to Adit about the idea behind Lula, how he founded the company in a pandemic and successfully raised a $5.5M seed round. Adit also speaks on what students today should be prioritizing for their development. This was such an insightful conversation that we hope you enjoy!


1:36 - Adit’s Background & Experiences with Hack-a-thons
 5:17 - Cultural & Family Influences
 9:48 - What should students today invest in?
12:24 - The Story of Lula Delivery
16:40 - How does Lula help business owners?
20:58 - How to Raise a $5.5M Seed Round
30:30 - Prioritizing your investment needs
34:50 - Adit’s pursuit of a PhD
38:40 - Importance of Mental Health in Work & Life
43:53 - “Hustle Culture”
46:00 - Lightning Round

Jun 08, 202248:45
GHP #69 - How to Raise Venture Capital Through Story-Telling with Robbie Crabtree!

GHP #69 - How to Raise Venture Capital Through Story-Telling with Robbie Crabtree!

Episode 69 is with Robbie Crabtree, Founder of Performative Speaking!

Robbie is a retired trial lawyer turned Startup Founder Coach turning founders into powerful storytellers. Having started his career in the legal sector, Robbie helped victims get justice for violent felonies, murders, & child abuse cases as a successful trial lawyer. After eight years of competitive storytelling in a courtroom with 102 jury trials, Robbie realized that his storytelling abilities can be used for much more.

Since shifting his focus to helping founders in Seed to Series C levels as a strategic advisor & coach, Robbie has helped clients raise over $135M in venture funding, build companies worth billions, and make their vision a reality.

We talk to Robbie about his career pivot from lawyer to startup coach. He explains the makings of a great story-teller, how to pickup on cues when people are lying, and the mistakes that founders make with pitch decks. He also details his steps to scaling his influence and how to balance authenticity with growth.

This was a great conversation with so many learnings throughout that we hope you enjoy!

Robbie Crabtree

 1:18 - Background & Career
 7:11 - How to Pivot Careers With Your Skills
10:40 - What Makes a Good Story/Story-teller?
13:50 - Social Media “Guru’s”
17:50 - Jeff Bezos’ Story-Telling in front of Congress
19:21 - How to Tell If Someone is Lying
24:00 - Biggest Mistake Founders Make with Pitch-decks
31:00 - Resources to Become a Better Story-teller
33:39 - Robbie’s Approach to Clients
38:27 - How To Scale Your Influence
42:38 - Validation Through Status
45:36 - Authenticity & Growth
48:24 - Failure & Triumph
50:18 - Lightning Round

May 09, 202253:48
GHP #68 - The World's First Self-Organizing Workspace with Dennis Xu!

GHP #68 - The World's First Self-Organizing Workspace with Dennis Xu!

Episode 68 is with Dennis Xu, Co-Founder of Mem Labs!

Mem is the world's first self-organizing workspace that leverages artificial intelligence to equip knowledge workers in the world with the information they need to do their best work. The free app is an early access platform dedicated to pushing users to quickly jot down their thoughts without focusing too heavily on the underlying organization of them.

We talk to Dennis about his journey to founding Mem and the inspiration behind it. He details the difference in tech landscapes between Canada and the USA, his experience at Stanford University, and how they secured a $5.6M seed round from Andreessen Horowitz. Dennis also explains important skills for builders in tech as well as what a day in the life of a cofounder looks like. 

This was a really insightful conversation that we hope you enjoy!


  1:18 - Dennis’ background
  4:44 - Tech in Canada vs. Tech in USA
 11:35 - Shift to remote work
 16:40 - Experience at Stanford
 21:14 - Must have skills to be a builder
 25:38 - Hard Skills vs. Intangibles
 27:30 - Three types of workers
 32:06 - Navigating terminations
 37:11 - What is
 51:04 - Day to Day Life of a Co-Founder
 54:10 - Securing a Seed Round from Andreessen Horowitz
1:01:07 - Biggest Influences
1:04:02 - Philosophy on Wealth Creation
1:08:39 - Lightning Round

May 04, 202201:11:20
GHP #67 - How to Raise a $6M Series A Through Your Customers & No VC's with Raad Ahmed!

GHP #67 - How to Raise a $6M Series A Through Your Customers & No VC's with Raad Ahmed!

Episode 67 is with Raad Ahmed, Founder & CEO of LawTrades!

LawTrades is pioneering a new work model that economically empowers independent legal professionals to monetize their skills, while helping companies build distributed legal teams. General Counsels have access to a highly selective talent network of attorneys, paralegals, compliance, and legal ops, to complement their own legal department and company culture.

We talk with Raad about his early music passions and influences to entrepreneurship. He details his journey from first discovering the internet to making 6-figures in online ad revenue while in law school. Raad also details his mission to achieve a utopian work-life balance through LawTrades, and how they successfully raised $6M at an $80M valuation using just a link and without pitching to VCs. This was a great conversation that weaves through career, life, and philosophy that we hope you enjoy!


3:05 - Passions & Influences
10:02 - “Passionately curious, but compulsively minimalist.”
18:34 - Challenges of Raising Capital
22:05 - How Justin Khan almost ruined LegalTrades
27:00 - How LegalTrades raised a $6M Series A with their customers
36:11 - VC Funding vs. RUV Funding
43:43 - What is LawTrades & What problem are they solving?
51:34 - Pros & Cons of Legal-Tech Industry
58:34 - Defining & Measuring Success
1:06:00 - Impact of the Founding Team
1:12:38 - Wealth Creation
1:20:36 - How Schooling Needs to Change
1:32:00 - Lightning Round

Apr 27, 202201:38:23
GHP #66 - Protecting Your Digital Assets & Legacy with Maika Isogawa!

GHP #66 - Protecting Your Digital Assets & Legacy with Maika Isogawa!

Episode 66 is with Maika Isogawa, Co-Founder and CEO at Webacy!

Webacy helps protect your digital legacy by allowing you to decide what you want to do with your digital life after you die. This includes your social media accounts blockchain-based assets, cryptocurrencies and other assets. Some of this involves deletion or memorialization of accounts, posting final, sequenced content, and transferring crypto or business accounts to your inner circle.

Maika is a former professional acrobat and performer for the Cirque Du Soleil brand of shows. She is also a Stanford '20 alumnus with a special concentration in Symbolic Systems, a program which combines the study of Human Computer Interaction, Software Engineering, Linguistics, Philosophy, and more. Maika was most recently a Cybersecurity Engineer for Microsoft, while Maika and Webacy have been recently recognized as a member of the Forbes 30 Under 30 list.

We sit down with Maika to discuss her early days with the Cirque du Soleil and how she became an entrepreneur. She details how she battles imposter syndrome, cultural influences in her life, including Anime, and how Webacy is securing digital assets for the world of tomorrow. This was a fun chat that we hope you enjoy!


 2:30 - Circus Acrobatics at Cirque du Soleil
 8:00 - Overcoming Fear & Imposter Syndrome
10:25 - Importance of Hobbies & Side Hustles
13:10 - Influence of Culture
17:00 - Anime Culture
19:50 - Goal Setting for Success
24:40 - Pressure to Succeed
28:18 - Happiness & Success
31:00 - The story behind Webacy
33:14 - Crypto scam that stole from Maika
35:30 - Challenges of Crypto-adoption
38:50 - Defining Company Culture
42:37 - Webacy’s Founding Team
45:37 - Managing Differing Opinions
49:04 - Advice for new entrepreneurs
50:05 - Lightning Round

Apr 19, 202252:51
GHP #65 - Millennials Meet Gen Z with Harsehaj Dhami and Samantha Ouyang!

GHP #65 - Millennials Meet Gen Z with Harsehaj Dhami and Samantha Ouyang!

Episode 65 is with Harsehaj Dhami and Samantha Ouyang, two International Baccalaureate high school students based in Toronto.

Harsehaj is an impact driven student working to bridge the healthcare access gap to low income families and those struggling with their mental health. She is currently helping build a health startup based out of San Francisco that has just raised their seed-round. In her personal projects, she’s working on modelling CNN (convolutional neural networks) that uses brain EEG scans to diagnose depression.

Samantha is a goal oriented student, passionate about using STEM, design, engineering and innovation to create lasting change in the world. Having started off in competitive programming at an early age, her experiences led her to founding, Superposition Toronto, a non-profit that helps to bridge the gender gap in STEM.

Samantha and Harsehaj have both crossed paths in The Knowledge Society - where cohorts of students are encouraged to solve the world’s biggest problems using emerging technologies. They have both previously worked together on a project focussed on removing chemical pollutants from drinking water.

We talk to Harsehaj and Samantha about their respective journeys in the tech space, the various differences in education and culture between generations, the influence of asian households, and much more. This was such an insightful conversation that brought to light the various evolutions of education, life, culture, and tech through the years. We hope you enjoy!

 2:45 - Harsehaj Intro & background
 6:45 - Samantha Intro & background
11:25 - Early Lessons from their experiences
18:58 - Cultural Influences of an Asian household
27:14 - How can schools encourage more innovation?
30:30 - Challenges of Women in Tech
37:30 - Social Pressures on Millennials & Gen Z
44:42 - Pros/Cons of Social Media for Gen Z
53:19 - Increasing Cost & Competition in Schooling
1:00:12 - What is the current tech focus for Gen Z?
1:03:39 - Lightning Round

Mar 29, 202201:09:32
GHP #64 - Empowering Freelancers & Becoming The Financial Company For Independents with Alexandra Nuth!

GHP #64 - Empowering Freelancers & Becoming The Financial Company For Independents with Alexandra Nuth!

Episode 64 is with Alexandra Nuth, Co-Founder and COO at Control HQ!

Control HQ is a financial management tool for freelancers and flexible workers. The freedom and flexibility of self employment is coveted, but not the antiquated process of managing your money, from irregular pay to income taxes.

Alexandra built her way up in corporate strategy before teaming up with two colleagues on this venture to become the financial management company for independents.

We talk to Alex about her move from corporate to entrepreneurship, the future of flexible work and why ControlHQ is so important in this space, the importance of mentorship, and so much more.

This was such an insightful conversation that we hope you enjoy!

Control HQ

1:43 - Intro & Background
4:56 - Transitioning from Corporate to Entrepreneurship
8:50 - Important Core Values
10:57 - Building Company Culture
15:06 - Importance of Mentorship
21:40 - What is Control HQ?
24:29 - What makes Control HQ different?
28:30 - Importance of Diversity & Inclusion
38:40 - Lightning Round

Mar 23, 202241:08
GHP #63 - Maximizing Innovation, Successful Entrepreneurship & Life Lessons From War with Lloyed Lobo!

GHP #63 - Maximizing Innovation, Successful Entrepreneurship & Life Lessons From War with Lloyed Lobo!

Episode 63 is with Lloyed Lobo, Co-Founder and President of Boast A.I.

Boast A.I helps companies access the billions of dollars available in R&D tax credits and funding to improve insights and grow faster. Their software integrates financial, engineering, and project data to increase the speed, accuracy, and size of eligible tax incentives. In other words, Boast helps you maximize claims and innovate faster while you run your business.

Lloyed is an entrepreneur through and through, with a never ending desire to keep moving, building, and hustling. We talk to Lloyed about his journey in tech, how being a refugee of the Gulf War in Kuwait shaped his mentality on life, and the plethora of lessons he’s gathered through his experiences thus far.

This was an insightful and candid conversation that you hope you enjoy!

2:01 - Background
 9:00 - Engineering Uncertainty (for Success)
16:25 - Managing Mental Health
26:43 - Importance of your Network
30:14 - The CAMPER Framework
33:00 - What is Boast A.I?
35:08 - How Boast A.I helps businesses with R&D Credits
38:04 - The Future of Boast A.I
39:51 - Raising $100M from Investors
51:51 - Advice to Founders
53:02 - Lightning Round

Mar 02, 202256:57
GHP #62 - Disrupting the Telecom Industry & Becoming a Better Entrepreneur with Brice Scheschuk!

GHP #62 - Disrupting the Telecom Industry & Becoming a Better Entrepreneur with Brice Scheschuk!

Episode 62 is with Brice Scheschuk, Co-Founder of WIND Mobile (now known as Freedom Mobile) and currently the Managing Partner at Globalive Capital.

The telecom space is one of the most regulated and red-tape ruled industries to work within, making Wind Mobile’s story an incredible achievement.

Brice led the Finance, HR, Procurement and Supply Chain functions of one of the largest new entrant pure play wireless services providers and helped raised approximately $2B in capital to acquire spectrum and operate the WIND network.

Now, he manages a $100M investment firm in Globalive focusing on representative private equity, real estate, and venture investments.

We talk to Brice about his journey breaking into the Canadian telecom space, the evolution of entrepreneurship through different eras, and impactful skills necessary for anyone looking to achieve success. He also explains the importance of mentorship and how he’s helping the next generation through MindFrame Connect.

This was an incredible informative episode that we hope you enjoy!

2:20 - Background and Education
5:30 - The Entrepreneurship Journey & Mindset
11:30 - Transferrable Skills through Generations
15:55 - Founding WIND Mobile
23:00 - Advice on Seeking Investors
30:52 - Assessing & Managing Risk in Life
38:25 - What is Anti-Fragility?
47:30 - Decision Making & Regret
56:55 - MindFrame Connect
01:02:50 - Lightning Round

Feb 21, 202201:11:48
GHP #61 - NFTs, the Blockchain, Codifying Value and Helping Creators Monetize Content with Ben Share!

GHP #61 - NFTs, the Blockchain, Codifying Value and Helping Creators Monetize Content with Ben Share!

Episode 61 is with Ben Share, Co-Founder and CEO at Dime!

Dime helps turn your content into genuine digital collectibles for your followers to buy, sell, trade and collect. While NFTs have the potential to transform the way we create art and use the internet, we still need a system in place that's powerful enough and clear enough for everyone to use.

Dime is the first NFT marketplace to not require a crypto wallet, the first to transact purely in $USD, and most importantly, the first marketplace that ordinary people will want to use.

We talk to Ben about the utility of NFTs, the Blockchain and Web 3.0. We discuss the future of these technologies and how creators will be significantly impacted by advancements in this space. He details his journey founding Dime and what the internet of tomorrow will look like as the foundations are laid today. 

If you’re looking to stay ahead of the next big shift on the internet, this episode is a must!

2:15 - Intro to Ben
4:54 - What is Web 3.0?
6:28 - Significance of Blockchain
8:11 - What is an NFT? Why are they important?
15:47 - Importance of Community
19:05 - What is a Rug Pull?
22:10 - NFT Investing: How To
26:44 - What is Dime?
28:37 - How Dime helps purchase NFTs
31:22 - How NFTs and Web 3.0 will help creators
35:12 - Challenges in & Advice for the Web 3.0 and NFT space
39:38 - The Y Combinator Experience
45:54 - Lightning Round

Feb 01, 202249:31
GHP #60 - Making Sound Financial Decisions using Artificial Intelligence with Kris Bennatti!

GHP #60 - Making Sound Financial Decisions using Artificial Intelligence with Kris Bennatti!

Episode 60 is with Kris Bennatti, Co-Founder, CEO and Lead Developer at Bedrock AI!

Bedrock AI are experts and innovators in the adaptation of language models to financial text that facilitate a unique, quantamental approach to reading and understanding SEC filings.

In other words, they use underused, unstructured data sources to understand and predict earnings management, accounting problems and outright fraud.

We talk to Kris about her journey from accounting as a CPA to founding Bedrock AI. She details the importance of machine learning in the financial markets and how investors and companies alike can benefit from its use. This was an incredibly insightful conversation that we hope you enjoy!

2:50 - Career Journey from CPA to Coding
7:40 - Advice to newcomers to Data Science
10:04 - Machine Learning vs. Artificial Intelligence
13:16 - Deep Learning Based Language Models
17:45 - "AI is inherently biased."
22:00 - The Concept of Singularity
24:17 - What is Bedrock AI?
28:59 - Example of how Bedrock AI helps investors
35:28 - The future of Bedrock AI
39:16 - Finding the right Business Partners
41:36 - Challenges of being a Founder
45:20 - Lightning Round

Jan 25, 202249:34
GHP #59 - Optimizing Onboarding, Offboarding, and Employee Engagement with Evan Hallward!

GHP #59 - Optimizing Onboarding, Offboarding, and Employee Engagement with Evan Hallward!

We're back & starting off 2022 with a great guest from the world of HR!

Episode 59 is with Evan Hallward, Co-Founder and Co-CEO at Aboard!

Aboard enables growing startups & small businesses to find, implement, and automate their People Programs. From onboarding to offboarding, and everything in between, Aboard ensures that employees will be better prepared to succeed.

We talk to Evan about his motivation behind founding this platform. He details how his experiences in recruitment and HR led him to building a people-focussed company of his own. This was a great conversation with so many learnings. We’ve all had our fair share of bad interview and employment experiences. If you’re looking to revamp your recruitment and employee engagement, this episode is sure to help!

2:15 - Evan’s Entrepreneurial Journey
6:14 - What does a successful interview process look like?
10:35 - War for Talent vs. Brand
11:40 - How to Optimize your Hiring Process
13:22 - How Start-Ups Fail at Hiring Talent
17:35 - Debunking the Negative Perception On Employment Length
19:51 - Defining “Employee Engagement”
24:45 - How to Retain Talent at your Company
30:19 - Transitioning from a “Task Role” to a “Manager Role”
31:45 - What is Aboard? How are they helping employers & employees?
36:50 - Lightning Round

Jan 18, 202240:52
GHP #58 - From CFO to Angel Investor, Keys to Success with Mark MacLeod

GHP #58 - From CFO to Angel Investor, Keys to Success with Mark MacLeod

Episode 58 is with Mark MacLeod!

Mark is a semi-active angel investor with a portfolio of 14 investments, 2 highly positive exits and counting. He was most notably General Partner at Real Ventures, Canada’s largest and most active seed stage fund. With a background in finance, he also served as CFO for software companies including, but not limited to, Shopify and Freshbooks.

We talk to Mark about his journey from finance to venture capital. He details his move from C-suite to investor, and the critical skills that are needed to help a start-up succeed. Mark also dives into the critical skills needed to become a leader in the industry.

This was a fun conversation with plenty of gems throughout, so we hope you enjoy!

1:31 - Mark's Career Journey
7:00 - They Key to Learning Fast
8:30 - Importance of Product-Market Fit
9:50 - Managing Stress in Decision Making
12:25 - Critical Skills Young Professionals Need to Learn
15:30 - Don’t Chase Titles. Do this instead.
19:04 - What makes a great leader?
22:45 - How to Develop Trust amongst Your Team
24:42 - How to Successfully Fundraise with VCs
27:10 - What Makes a Start-Up Investment Worthy?
31:40 - How Mark got into DJ-ing and Fitness
34:40 - Lightning Round

Nov 26, 202138:01
GHP #57 - Helping Non-Profits Raise More Money Using Artificial Intelligence with Alexander Jivov!

GHP #57 - Helping Non-Profits Raise More Money Using Artificial Intelligence with Alexander Jivov!

Episode 57 is with Alexander Jivov, Co-Founder & CEO at Hopeful Inc.!

Hopeful Inc. is the first Social Fund-tech platform that enables nonprofits and charities to monetize their social media followers specifically for fundraising, while giving them visibility on why donors are engaging through a proprietary Storytelling A.I. dashboard.

Alex is a Salesperson, Digital Marketer, Full-Stack Web Developer, Chef, and published author - a true jack of all trades with an interesting career path to say the least!

We talk to Alex about his career journey and how he pivoted through so many different avenues. He describes the process of building a start-up in the non-profit industry, building out a successful founding team, and how to figure out the right career for yourself. Alex also details the importance of mentorship through accelerators and incubators from his experience with the Ryerson DMZ and UC Berkeley SkyDeck.

This was an incredibly informative episode that’s sure to have a bit of everything for everyone, so we hope you enjoy!

1:53 - Alex’s Unorthodox Career Path
4:32 - How to effectively experiment early on in your career
6:16 - Building a Client Acquisition Strategy
8:31 - How to Become a Better Salesperson
10:19 - What is Hopeful Inc & How are they helping non-profits?
16:31 - Challenges Faced by Hopeful Inc.
18:30 - Hopeful Inc.’s Acquisition
24:02 - Defining Success For Your Company & Employees
27:10 - The Future of Hopeful Inc.
29:00 - Advice for Entering the Non-Profit industry
32:04 - Lightning Round

Oct 26, 202136:36