Building True Community in Venture, the Power of Authentic Expression, and How to Handle Difficult Conversations, with Brandon Brooks of Overlooked Ventures

In this episode, Justin Gordon (@justingordon212) talks with Gale Wilkinson (@galeforceVC) Founder and Managing Partner of Vitalize Venture Capital, a $16M seed-stage fund based in Chicago, San Francisco, and Los Angeles. While Gale mainly invests in the future of work through Vitalize, she also works to empower others - advocating for angel investing for everyone.Gale is also a startup advisor, on the Chicago: Blend Board, in Kauffman Fellows Class 23, has an MBA from the University of Chicago Booth School of Business, and is a dog lover.Gale's Twitter: https://twitter.com/galeforceVCShow NotesHow Gale began angel investing (In 2012)Gale's background leading investments in 65 companies, investing $50MThe story around Gale's first angel investmentGetting more women to start angel investingBuilding a muscle for investing - learning how to identify strong opportunities Choosing winners - Qualities of founders Gale has invested inLPA: Delineating between Angel Investing and Fund InvestingBuilding a portfolio as an angel investor  - Best strategies, writing 30 checks in 25 companies between pre-seed and series A No matter how you start, just start - getting involved, adding value, deploying small amounts of capitalPassionate about sustainability and diverse founding teamsA few of Gale's angel investmentsTime Commitment: An overview for novice Angel investorsAccess: The two kinds of angel investing, passive and active Getting started as an LP into venture funds and how Gale made her investment into Mac Conwell and Rarebreed Ventures  VC's evolving culture: Gale's community-based approach to investing, being an LP with Rarebreed Ventures, Emerging managersThe power of Twitter  More about the show:The Vitalize Podcast, a show by Vitalize Venture Capital (a seed-stage venture capital firm and pre-seed 300+ member angel community open to everyone), dives deep into the world of startup investing and the future of work.Hosted by Justin Gordon, the Director of Marketing at Vitalize Venture Capital, The Vitalize Podcast includes two main series. The Angel Investing series features interviews with a variety of angel investors and VCs around the world. The goal? To help develop the next generation of amazing investors. The Future of Work series takes a look at the founders and investors shaping the new world of work, including insights from our team here at Vitalize Venture Capital. More about us:Vitalize Venture Capital was formed in 2017 as a $16M seed-stage venture fund and now includes both a fund as well as an angel investing community investing in the future of work. Vitalize has offices in Chicago, San Francisco, and Los Angeles.The Vitalize Team:Gale - https://twitter.com/galeforceVCCaroline - https://twitter.com/carolinecasson_Justin - https://twitter.com/justingordon212Vitalize Angels, our angel investing community open to everyone:https://vitalize.vc/vitalizeangels/

In this special episode, Justin Gordon (@justingordon212), the Director of Marketing with VITALIZE Venture Capital, interviews three key VITALIZE team members, Founder and Managing Partner Gale Wilkinson (@galeforceVC), Partner Caroline Casson (@carolinecasson_), and Community Manager Larissa Insogna (@LarissaInsogna).VITALIZE Venture Capital was formed in 2017 as a $16M seed-stage venture fund and now includes both a fund as well as an angel investing community investing in the future of work. VITALIZE has offices in Chicago, San Francisco, and Los Angeles. We believe in people and process. From our investors to team members to the founders we fund, we are focused on building a community of amazing people. Venture capital is a relationship business, and one of our core differentiators is how we leverage our extensive network to provide value to our portfolio companies. We make valuable connections for our companies, mostly to prospective customers and other VC firms, but we field all types of requests to help our portfolio companies flourish. As founders ourselves, we have learned a lot from building this investment firm. We have implemented effective processes for deal flow, due diligence, and helping our companies post-investment, allowing us to move quickly and offer a high-quality product to founders and investors. VITALIZE Venture Capital: https://vitalize.vc/VITALIZE Angels: https://vitalizeangels.com/VITALIZE on LinkedIn: linkedin.com/company/vitalizevcVITALIZE on Twitter: @VitalizeVC Show Notes:How Gale got into venture and started the Irish Angels investment networkHow Caroline decided to partner with GaleCaroline’s cross-country cycling adventure and Gale’s pandemic road tripsLarissa’s diverse professional experiences and how she ended up running community at VITALIZEHow a cold DM to get Gale on Justin’s own podcast led to him joining VITALIZEThe challenges and less glamorous side of working in VCHow Gale envisions achieving a manageable workload for herself and her teamThe effect of the COVID pandemic on their schedulesDifferent strategies the team members use to create boundaries for a healthy work-life balanceMaking investing accessible to everyone through the VITALIZE Angels communityGale and Caroline’s thoughts on the future of early stage ventureVITALIZE’s North Star and the strategy to get therePotential paths for the future of VITALIZEThe trailblazing work some of our VITALIZE Angels community members are involved inThe due diligence process for VITALIZE AngelsWhat makes a good fit to become a VITALIZE Angels portfolio companyWhat to expect in terms of ROI for our VITALIZE Angels membersThe value of angel investing communitiesMore about the show:The Vitalize Podcast, a show by Vitalize Venture Capital (a seed-stage venture capital firm and pre-seed 300+ member angel community open to everyone), dives deep into the world of startup investing and the future of work.Hosted by Justin Gordon, the Director of Marketing at Vitalize Venture Capital, The Vitalize Podcast includes two main series. The Angel Investing series features interviews with a variety of angel investors and VCs around the world. The goal? To help develop the next generation of amazing investors. The Future of Work series takes a look at the founders and investors shaping the new world of work, including insights from our team here at Vitalize Venture Capital. More about us:Vitalize Venture Capital was formed in 2017 as a $16M seed-stage venture fund and now includes both a fund as well as an angel investing community investing in the future of work. Vitalize has offices in Chicago, San Francisco, and Los Angeles.The Vitalize Team:Gale - https://twitter.com/galeforceVCCaroline - https://twitter.com/carolinecasson_Justin - https://twitter.com/justingordon212Vitalize Angels, our angel investing community open to everyone:https://vitalize.vc/vitalizeangels/

Learn more about Vitalize Angels:https://vitalize.vc/vitalizeangels/Our deal close process for founders:https://vitalize.notion.site/Deal-Close-Process-c95157c58dc3447fa8537b8447e9db79More about us:Vitalize Venture Capital was formed in 2017 as a $16M seed-stage venture fund and now includes both a fund as well as an angel investing community investing in the future of work. Vitalize has offices in Chicago, San Francisco, and Los Angeles.The Vitalize Team:Gale - https://twitter.com/galeforceVC​Caroline - https://twitter.com/caroline_yeager​Justin - https://twitter.com/justingordon212​

This is a special episode pulled from the VITALIZE vault—back when The VITALIZE Podcast was Talking Venture! Justin Gordon (@justingordon212) talks with Amanda DoAmaral (@AmandaDoAmanda), Co-Founder of Fiveable, a social learning network for students. Since this original episode released in May 2021, Fiveable has raised a $10M Series A. Fiveable is an educational technology company that is committed to unlocking opportunities for young people through academic and social empowerment. At Fiveable they believe that students who are educated, confident, and informed will open more opportunities for their future. Fiveable aims to give equal opportunities for all students to reach their potential.Amanda DoAmaral is an educator, activist, and co-founder of Fiveable. She spent half a decade teaching high school history in Oakland, CA, where her passion for creating equitable educational opportunities was ignited. Amanda has been a vocal advocate for inclusive history curriculum and is active within the Milwaukee tech community.Website: FiveableLinkedIn: linkedin.com/in/adoamaral/Twitter: @AmandaDoAmandaShow Notes:What Fiveable doesOnboarding Serena Williams and Chelsea Clinton as an investorsFiveable’s origin storyTurning tutoring ex-students via livestream into a VC-backed startupFiveable’s early growth stageHow the Fiveable product has evolved over timeRisk assessment and hiring a teamGenerational entrepreneurship and participating in an acceleratorThe lack of education about available resources for foundersAmanda’s experience with gener8tor and how it contributed to Fiveable’s growthRaising pre-seed capital and the stress of executing fund allocationWhat has fueled Fiveable’s growthContent development and SEO strategyManaging an expansive team and hiring studentsThe impact of building in publicThe big vision for FiveableMore about the show:The Vitalize Podcast, a show by Vitalize Venture Capital (a seed-stage venture capital firm and pre-seed 300+ member angel community open to everyone), dives deep into the world of startup investing and the future of work.Hosted by Justin Gordon, the Director of Marketing at Vitalize Venture Capital, The Vitalize Podcast includes two main series. The Angel Investing series features interviews with a variety of angel investors and VCs around the world. The goal? To help develop the next generation of amazing investors. The Future of Work series takes a look at the founders and investors shaping the new world of work, including insights from our team here at Vitalize Venture Capital. More about us:Vitalize Venture Capital was formed in 2017 as a $16M seed-stage venture fund and now includes both a fund as well as an angel investing community investing in the future of work. Vitalize has offices in Chicago, San Francisco, and Los Angeles.The Vitalize Team:Gale - https://twitter.com/galeforceVCCaroline - https://twitter.com/carolinecasson_Justin - https://twitter.com/justingordon212Vitalize Angels, our angel investing community open to everyone:https://vitalize.vc/vitalizeangels/