The Generation Hustle Podcast

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 https://www.unusual.vc/ Timestamps 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

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 https://race.capital/ Timestamps   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

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 https://realventures.com/ Timestamps 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

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 https://eniac.vc/ Timestamps 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

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 https://www.redpoint.com/ Timestamps 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

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. Foundraisr https://www.foundraisr.com/ Timestamps  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

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. Prepared https://www.prepared911.com/ Neal Soni https://www.nealsoni.com/ Timestamps  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

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 https://www.hustlefund.vc/ Elizabeth Yin https://elizabethyin.com/ Timestamps  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

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 MyTutor.ca, 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 https://mistral.vc/ Timestamps  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

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 https://www.maellegavet.com/ Techstars https://www.techstars.com/ Timestamps  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?”