Angel Investing: Creating Your Thesis, Building Conviction, and Investing in the Future of Work with Stella Garber, Former Head of Marketing at Trello
Play • 25 min

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:

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 -
Caroline -
Justin -

Vitalize Angels, our angel investing community open to everyone:

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