The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20VC: Alexa Von Tobel on Raising NYC's Largest Ever Female Led Fund , Portfolio Construction, Compression of Fundraising Timelines, Reserves Management & Personal Branding in Venture

Jan 31, 2020

Alexa Von Tobel, Founder and Managing Partner at Inspired Capital, discusses her journey from launching LearnVest to leading NYC's largest female-led VC fund. She shares her unique approach to portfolio construction, including a strategy that segments investments into three buckets. Alexa also addresses the challenges of misalignment between VCs and founders, the delicate art of saying no, and the changing dynamics of fundraising timelines. Emphasizing that capital is no longer the only differentiator, she highlights the importance of relationships in venture capital.

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ANECDOTE

Early Entrepreneurial Spirit

Alexa Von Tobel's entrepreneurial journey began early, selling art from her parents' house.
This drive led her to Harvard, Insight Venture Partners, and eventually founding LearnVest, which was acquired for $375 million.

INSIGHT

Angel vs. Institutional Investing

Angel investing involves managing your own capital, allowing for more flexibility in return expectations and founder selection.
Institutional investing requires a stricter approach, prioritizing fiduciary responsibility and fund performance.

INSIGHT

Inspired Capital's LP Pitch

Inspired Capital's pitch to LPs resonated due to the team's strong bond, diverse experience, and passion for entrepreneurship.
Their combined experience building and scaling companies, along with deep New York roots, further solidified their appeal.

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Alexa Von Tobel is the Founder & Managing Partner @ Inspired Capital, announced in 2019 as the largest ever female-led VC fund based in NYC. Prior to co-founding Inspired, Alexa founded LearnVest where she enjoyed an incredible 11-year journey culminating in their $250M exit to Northwestern Mutual in 2015. Alexa is also the author of New York Times Bestseller "Financially Fearless" and is an inaugural member of the Presidential Ambassadors for Global Entrepreneurship for the White House.

In Today’s Episode You Will Learn:

1.) How Alexa made her way into the world of startups with the founding of LearnVest? How did that experience running LearnVest lead to her founding NYC's largest-ever female-led VC fund in the form of Inspired?

2.) How does Alexa think about portfolio construction with the new $200M fund? What does she mean when she says they have segmented it into 3 distinct and separate buckets? How much is in each bucket? How does Alexa think about reserves and re-investment decision making? What is the process here?

3.) As a former entrepreneur, how does Alexa think about those moments when the VC and the Founder are no longer aligned? What are those moments? How does Alexa approach the aspect of saying no to founders? What is the right way? How does Alexa feel about the compression in fundraising timelines? How does Alexa meet founders before they raise their round?

4.) Why does Alexa believe that capital is no longer the differentiator? How does Alexa think about personal brand in venture today? Where does Alexa believe are the most crucial times for reputation building? How does Alexa approach time allocation across the portfolio? What is the correlation between decision-making and reputation?

Items Mentioned In Today’s Show:

Alexa’s Fave Book: The Power of Moments: Why Certain Experiences Have Extraordinary Impact

Alexa’s Most Recent Investment: Snackpass

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