The VITALIZE Podcast: Venture Capital | Startups | Angel Investing

In this episode of The Vitalize Podcast, Justin Gordon (@justingordon212) talks with Wen-Wen Lam ((@wenwen)) Partner at Gradient Ventures. Former CEO and co-founder of NexTravel (YC15)- acquired by Travelperk in 2020. Advisor/Investor in awesome early stage tech/e-commerce companies including Runway, Tuckernuck, Messageme, Final, Meadow, Aero, and more. Lover of technology, travel, and very expensive shoes.

Website: Gradient Ventures

Linkedin: linkedin.com/in/wenwen

Show Notes

• Transitioning from founder to VC at Gradient Ventures
• How being a founder influenced Wen-Wen as an investor
• What Wen-Wen looks for in founders
• Investing in Party Round's pre-seed funding
• Wen-Wen's core focus for the companies they are investing in with Gradient ventures
• How hands-on Wen-Wen is when working with companies
• Angel investing prior to Gradient Ventures
• How Wen-Wen manages her time now
• What Wen-Wen is excited for next

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/galeforceVC
Caroline - https://twitter.com/carolinecasson_
Justin - https://twitter.com/justingordon212

Vitalize Angels, our angel investing community open to everyone:
https://vitalize.vc/vitalizeangels/

Justin Gordon (@justingordon212) talks with Hunter Walk (@hunterwalk) Partner at Homebrew - Providing early-stage investment, assistance & love to entrepreneurs building companies for the Bottom Up Economy. Investments include ShieldAI, Plaid, Gusto, Chime, Cruise, Bowery Farming, and other FinTech, SaaS, API, marketplace, commerce businesses.

Before Homebrew, he led consumer product management at YouTube, starting when it was acquired by Google. He originally joined Google in 2003, managing product and sales efforts for AdSense, Google‘s contextual advertising business. His first job in Silicon Valley was as the founding product and marketing guy at Linden Lab. Before graduate school, he was a management consultant and also spent a year at Late Night with Conan O‘ Brien. His parents are proud of his BA in History from Vassar and MBA from Stanford University.

Hunter Walk’s Twitter: https://twitter.com/hunterwalk

Topics Discussed: 

• Leaving google and launching his own venture
• Different ways of being an investor
• Angel investing 
• Blogging as an investor
• The value of Twitter
• Screendoor, an organization supporting underrepresented General Partners of emerging venture capital funds
• How Hunter's time at Google impacted him

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/galeforceVC
Caroline - https://twitter.com/carolinecasson_
Justin - https://twitter.com/justingordon212

Vitalize Angels, our angel investing community open to everyone:
https://vitalize.vc/vitalizeangels/

Justin Gordon (@justingordon212) talks with David Chang (@changds) in this episode. David is an entrepreneur and angel investor who has held operating roles at six startups and invested in 70+ companies. He was most recently the Chief Executive Officer of Gradifi, which was acquired by E*TRADE. Previously, he was Entrepreneur-in-Residence at Harvard Business School and Director of the Babson Summer Venture Program.

As a leader in the entrepreneurship community, David holds several advisor/board memberships. He is on the board at MITX, an advisor at Harvard Ventures, Nanigans, CO Everywhere, OpenFrame, and Linkwell Health. He has made 70+ angel investments in startups such as Crashlytics, clypd, Amino, Logz, Cuseum, CarePort Health, Dashfire, Mogul, Uncharted Play, through the Where Angel Fund and TBD Angels. David is a frequent speaker on the topics of startups, fundraising, and the Boston tech ecosystem, and he actively mentors students and founders. 

Awards include Boston Business Journal's Power 50: Most Influential Bostonians, BostInno’s 50 on Fire: Education Winner / Investment Winner / Tech Finalist, and Finalist for NEVY Angel of the Year.

David Chang’s Twitter:  https://twitter.com/changds

Show Notes: 

• Switching from entrepreneurship to investing
• What makes David comfortable investing in more companies
• How David chooses the amount to invest
• David’s portfolio structure as an angel investor
• The best investment David made
• Investing with through an angel group
• The structure of TBD Angels and tools used to manage it
• What David is looking for as an angel investor
• His thoughts about subconscious bias and underrepresented founders
• Sourcing deals from universities

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/galeforceVC
Caroline - https://twitter.com/carolinecasson_
Justin - https://twitter.com/justingordon212

Vitalize Angels, our angel investing community open to everyone:
https://vitalize.vc/vitalizeangels/

Justin Gordon (@justingordon212) talks with Jessica Chang (@jessicajchang) Co-founder and CEO at WeeCare, a childcare network that provides access to affordable, high-quality childcare while supporting childcare providers in operating sustainable businesses through technology.

WeeCare has also created the only childcare benefits program built to enable employers of all sizes to cost-effectively offer employees and team members the most convenience and support for their childcare needs. WeeCare’s Childcare Benefits result in decreased employee absenteeism, reduced job turnover, and increased job satisfaction.

More information about WeeCare:

WeeCare is the largest childcare network in the United States, with the mission of providing access to affordable, high-quality childcare for all families. Parents use WeeCare to find, tour, and enroll with the perfect childcare provider for their family. WeeCare supports families along the way with messaging, photo and video updates, and health and safety features through the app. Childcare providers are supplied with the support and tools they need to manage and grow their business with ease, including enrollment and finance management, tuition payment collection, and professionally developed curriculum. WeeCare was founded by a team set on solving the childcare crisis and proud to support women and minority-owned small businesses.

Jessica Chang’s Twitter: https://twitter.com/jessicajchang

Show notes:

- What WeeCare does
- The other side of Jessica's marketplace
- Where the idea of building a childcare network came from
- What fueled the growth of Weecare
- The experience of building a two-sided marketplace
- Growing WeeCare during the pandemic
- The average daycare costs
- The advantage of having childcare benefits
- The biggest pushback Jessica got from companies
- Jessica's educational advice
- The benefit of providing data back to Jessica’s employees
 
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 ( https://vitalize.vc/ ), 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/galeforceVC
Caroline - https://twitter.com/carolinecasson_
Justin - https://twitter.com/justingordon212

Vitalize Angels, our angel investing community open to everyone:
https://vitalize.vc/vitalizeangels/

Justin Gordon (@justingordon212) talks with Anne Dwane (@adwane) Co-founder and Partner at Village Global - an early-stage venture fund backed by some of the world’s most successful entrepreneurs. From how they invest in startups to how they help founders. They operate as a network.

Anne Dwane is passionate about aligning teams and applying technology to unleash human potential.

The venture firm is backed by an impressive and diverse group of investors that includes:  Jeff Bezos, Sara Blakely, Reid Hoffman, Magic Johnson, Anne Wojcicki, Mark Zuckerberg, Diane Green, Judy Estrin, Bill Gates, and Ken Chennault.

Anne Dwane’s Twitter: https://twitter.com/adwane

Show Notes:

- Switching from executive to venture capitalist
- Starting Village Global
- Building a systemic network to advantage founders
- How Anne started investing
- Anne Dwane's investment strategy
- Village Global's process of evaluating startups
- The best advice Anne got in looking for the best companies
- How Anne helps founders, emerging managers, and angels find simplicity beyond complexity in venture capital
- How Anne and her team decide what projects to focus on
- What Anne is excited about now

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/galeforceVC​
Caroline - https://twitter.com/caroline_yeager​
Justin - https://twitter.com/justingordon212​

Vitalize Angels, our angel investing community open to everyone:
https://vitalize.vc/vitalizeangels/

In this episode of The Vitalize Podcast, Justin Gordon (@justingordon212) talks with Andrew Gluck (@irrvrntVC) the GP of irrvrntVC, a firm focused on early-stage companies in the DTC, AdTech, and NextGen Commerce areas. He especially loves partnering with first-time founders so they can learn from his mistakes. Prior to that he co-founded and ran Agency Within, the largest independent digital marketing agency with a focus on direct-response, data-driven marketing. He managed close to $1BB in spend for clients like Nike, Billie and Zola.

Andrew's Twitter: https://twitter.com/irrvrntVC

Topics Discussed

- How Andrew got into investing and invested in Caraway pre-product and pre-launch, Branch Furniture after reaching out on LinkedIn, and Lunchbox as the first check
- Finding great founders in great markets
- What makes founders stand out
- The benefit of having the experience of working with a lot of different early-stage founding teams
-  Why Andrew over indexes on go-to-market and CAC and the level of detail founders can go into
- The importance of timing at pre-seed
- How hands-on Andrew is as an investor
- How to find companies really early and the cap Andrew put on companies he can invest in out of his fund
- The opportunity at the early stages of investing
- Why Andrew started a rolling fund vs. just continuing angel investing
- Figuring out the structure for a rolling fund and the amount to raise

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/galeforceVC
Caroline - https://twitter.com/carolinecasson_
Justin - https://twitter.com/justingordon212

Vitalize Angels, our angel investing community open to everyone:
https://vitalize.vc/vitalizeangels/

In this episode of The Vitalize Podcast, Justin Gordon (@justingordon212) talks with Stella Garber (@startupstella) former Head of Marketing at Trello and Anger Investor. Stella invests in the future of work and serves as an advisor for Origin Ventures and OpenView. She has invested in 4 women-led funds in 2021 alone and continues to add to her portfolio of more than 25 startups, some of which include Cameo, Tovala, Beam. Her experience as an investor has made her bullish on the value of creating your own investment thesis as an angel investor; being hands-on, and having conviction in your investments.  
 
Before actively angel investing and advising early-stage tech companies and venture funds, Stella built Trello's marketing team and strategy as the first marketing executive and led the team through a $425 million acquisition by Atlassian.

Stella's Twitter: https://twitter.com/startupstella

Show Notes

• How Stella started angel investing (In 2016)
• How her first investment went public and the second one failed
• Investing as an LP in venture capital funds
• Stella's 27 investments so far
• How Stella thought about her portfolio after her first investment
• The different ways to do angel investing (LP, SPVs, AngelList syndicates, direct)
• Why Stella has been doing more direct cap table investing
• The value of creating your own investment thesis as an angel investor
• Thinking about where you can add value as an angel investor
• Areas the Stella enjoys investing in
• Why Stella invests in the future of work
• How Stella gets conviction around writing a check
• How angel investing enables wealth creation
• How Stella thinks through allocating her angel investing dollars
• Gender disparity between women sharing deals and men sharing deals
• Investor networks and the ones Stella is involved with
• Diversity on cap tables and founders saving room on their cap tables for women and people of color
• Balancing being a full-time employee and angel investor
• How hands-on Stella is with her angel investments and what she helps companies with
• The expertise investors can bring to founders 
• The question to ask yourself as an investor
• Ways to get access to deals as an angel investor
• How Stella got started as an LP and the importance of getting more women and people of color LPs in VC
• Future of work trends Stella is interested in

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/galeforceVC
Caroline - https://twitter.com/carolinecasson_
Justin - https://twitter.com/justingordon212

Vitalize Angels, our angel investing community open to everyone:
https://vitalize.vc/vitalizeangels/

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/galeforceVC

Show Notes

• How Gale began angel investing (In 2012)
• Gale's background leading investments in 65 companies, investing $50M
• The story around Gale's first angel investment
• Getting more women to start angel investing
• Building a muscle for investing - learning how to identify strong opportunities 
• Choosing winners - Qualities of founders Gale has invested in
• LPA: Delineating between Angel Investing and Fund Investing
• Building 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 capital
• Passionate about sustainability and diverse founding teams
• A few of Gale's angel investments
• Time Commitment: An overview for novice Angel investors
• Access: 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 managers
• The 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/galeforceVC
Caroline - https://twitter.com/carolinecasson_
Justin - https://twitter.com/justingordon212

Vitalize Angels, our angel investing community open to everyone:
https://vitalize.vc/vitalizeangels/

In this episode of The Vitalize Podcast, Justin Gordon (@justingordon212) talks with Leo Polovets (@lpolovets). Leo Polovets is a co-founder and General Partner at Susa Ventures. He invests across sectors but mostly focuses on b2b companies. A few specific sectors he's invested in heavily are enterprise software; developer tools and technical products; and logistics and supply chain. He led Susa's investments in dozens of companies, including Outlier, Pex, Scalyr, and Stedi. 
 
Having been a software engineer for 10+ years, he approaches challenges with an engineering mindset and supports portfolio companies in vetting and hiring technical talent. 

Prior to Susa, he was the second engineering hire at Linkedin where he helped build the first versions of products like LinkedIn Jobs and LinkedIn Groups. He then worked on payment fraud detection algorithms at Google and was also an early engineer at Factual, where he built data cleaning, processing, and deduping software.

Leo's Blog: https://www.codingvc.com/ 
Leo's Twitter: https://twitter.com/lpolovets

Topics Discussed:

• The story around Susa Ventures' investment in Pex
• 3 big risks Pex had as a company and why Susa Ventures invested a couple of years after initially meeting them
• The importance of moats in startups and why they are a key to what Susa Ventures looks for in companies
• Moats that people don't talk much about including Robinhood's UX moat
• A "schlep moat"
• How to get access to deals as an investor
• Why being a focused investor can attract founders
• The importance of investing in underserved markets
• Sourcing, vetting, and winning when it comes to hiring technical talent
• How Susa Ventures built its reputation over time
• How Leo got started angel investing and invested in 70 companies
• What Leo looks for from angel investing
• How learning accelerates through angel investing
• Building a portfolio of angel investments
• Determining a check size for angel investing
• Why you should spread your investments out over a number of companies and years
• Thoughts on founders becoming angel investors
• What Leo is most excited about in VC

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/galeforceVC
Caroline - https://twitter.com/carolinecasson_
Justin - https://twitter.com/justingordon212

Vitalize 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-c95157c58dc3447fa8537b8447e9db79

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/galeforceVC​
Caroline - https://twitter.com/caroline_yeager​
Justin - https://twitter.com/justingordon212​