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Jan 31, 2020 · 38m · 20vc

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

Alexa von Tobel · 25m spoken Harry Stebbings · 10m spoken
0:00 / 0:00

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In this episode of The 20 Minute VC, host Harry Stebbings interviews Alexa von Tobel, founder and managing partner of Inspired Capital. They discuss her transition from founding LearnVest to launching a $200 million NYC-based venture fund, covering LP fundraising, portfolio construction, founder empathy, and the expansion of the New York tech ecosystem.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 29% of the talking time here. How this is scored →

Harry as informed peer 3.0 Guest teaching 2.8 Guest disagreement 0.7 Harry pushing back 1.2
05100:0010:0020:0030:002:45–4:46 · Harry as informed peer 2/10 Alexa von Tobel's Journey from Entrepreneurship to Venture Capital Harry welcomes Alexa and asks a standard opening question about her transition from entrepreneur to angel investor and founder of Inspired Capital. Alexa shares her background starting from selling art as a kid to dropping out of HBS and founding LearnVest.4:46–8:55 · Harry as informed peer 4/10 Transitioning Mindset from Angel Investor to Institutional Fund Manager Harry demonstrates industry knowledge by citing insights from Josh Koppelman and Andy McLaughlin regarding the mindset shift from angel to institutional investing. Alexa details how fiduciary duty sharpens investment decisions and outlines her team's background.8:55–13:36 · Harry as informed peer 3/10 Reflections on Fund One Fundraising Process Harry pushes Alexa to be self-critical about Fund I fundraising mistakes. Alexa explains the personal logistics of having a baby during the raise and then details her 50/50 reserve management and portfolio construction model.13:37–18:45 · Harry as informed peer 5/10 Managing Follow-On Reserves and Aligning with Founders on Valuation Harry directly challenges Alexa on potential misalignment when investors price internal follow-on rounds and want lower valuations. Alexa firmly rejects the premise, arguing that true venture returns are made on selecting breakout winners rather than squeezing valuation margins.18:45–20:50 · Harry as informed peer 3/10 Navigating Compressed Fundraising Timelines through Community Building Harry asks whether compressed fundraising timelines hinder building genuine founder relationships. Alexa outlines her proactive community-building strategy, including informal monthly dinners to meet founders well before rounds happen.21:03–24:24 · Harry as informed peer 2/10 Personal Brand vs. Core Reputation in Venture Capital Harry admits his own difficulty in saying no to founders, prompting Alexa to deliver candid coaching. She advises him to 'lean into the pain' (LITTP) and build a fast, honest refusal muscle as a core duty of the job.24:29–30:04 · Harry as informed peer 2/10 Mentorship Models and Partner Dynamics Harry asks about multi-generational mentorship models and whether co-founders can double as mentors. Alexa shares the origin stories of recruiting Penny Pritzker and Lucy Deland to co-found Inspired Capital.30:06–32:11 · Harry as informed peer 4/10 The Growth and Potential of the New York Tech Ecosystem Harry offers an informed thesis that New York lacks genuine lead investors despite looking crowded. Alexa validates his point and supports it with a 12-to-1 capital disparity statistic comparing Silicon Valley to NYC per capita.32:11–35:48 · Harry as informed peer 2/10 Quickfire Round: Books, Boards, and Recent Investments Harry conducts a standard quickfire round touching on books, board dynamics, and recent investments. Alexa shares takeaways from 'The Power of Moments' and her investment in Snackpass.2:45–4:46 · Guest teaching 1/10 Alexa von Tobel's Journey from Entrepreneurship to Venture Capital Harry welcomes Alexa and asks a standard opening question about her transition from entrepreneur to angel investor and founder of Inspired Capital. Alexa shares her background starting from selling art as a kid to dropping out of HBS and founding LearnVest.4:46–8:55 · Guest teaching 2/10 Transitioning Mindset from Angel Investor to Institutional Fund Manager Harry demonstrates industry knowledge by citing insights from Josh Koppelman and Andy McLaughlin regarding the mindset shift from angel to institutional investing. Alexa details how fiduciary duty sharpens investment decisions and outlines her team's background.8:55–13:36 · Guest teaching 3/10 Reflections on Fund One Fundraising Process Harry pushes Alexa to be self-critical about Fund I fundraising mistakes. Alexa explains the personal logistics of having a baby during the raise and then details her 50/50 reserve management and portfolio construction model.13:37–18:45 · Guest teaching 5/10 Managing Follow-On Reserves and Aligning with Founders on Valuation Harry directly challenges Alexa on potential misalignment when investors price internal follow-on rounds and want lower valuations. Alexa firmly rejects the premise, arguing that true venture returns are made on selecting breakout winners rather than squeezing valuation margins.18:45–20:50 · Guest teaching 2/10 Navigating Compressed Fundraising Timelines through Community Building Harry asks whether compressed fundraising timelines hinder building genuine founder relationships. Alexa outlines her proactive community-building strategy, including informal monthly dinners to meet founders well before rounds happen.21:03–24:24 · Guest teaching 6/10 Personal Brand vs. Core Reputation in Venture Capital Harry admits his own difficulty in saying no to founders, prompting Alexa to deliver candid coaching. She advises him to 'lean into the pain' (LITTP) and build a fast, honest refusal muscle as a core duty of the job.24:29–30:04 · Guest teaching 2/10 Mentorship Models and Partner Dynamics Harry asks about multi-generational mentorship models and whether co-founders can double as mentors. Alexa shares the origin stories of recruiting Penny Pritzker and Lucy Deland to co-found Inspired Capital.30:06–32:11 · Guest teaching 3/10 The Growth and Potential of the New York Tech Ecosystem Harry offers an informed thesis that New York lacks genuine lead investors despite looking crowded. Alexa validates his point and supports it with a 12-to-1 capital disparity statistic comparing Silicon Valley to NYC per capita.32:11–35:48 · Guest teaching 1/10 Quickfire Round: Books, Boards, and Recent Investments Harry conducts a standard quickfire round touching on books, board dynamics, and recent investments. Alexa shares takeaways from 'The Power of Moments' and her investment in Snackpass.2:45–4:46 · Guest disagreement 0/10 Alexa von Tobel's Journey from Entrepreneurship to Venture Capital Harry welcomes Alexa and asks a standard opening question about her transition from entrepreneur to angel investor and founder of Inspired Capital. Alexa shares her background starting from selling art as a kid to dropping out of HBS and founding LearnVest.4:46–8:55 · Guest disagreement 0/10 Transitioning Mindset from Angel Investor to Institutional Fund Manager Harry demonstrates industry knowledge by citing insights from Josh Koppelman and Andy McLaughlin regarding the mindset shift from angel to institutional investing. Alexa details how fiduciary duty sharpens investment decisions and outlines her team's background.8:55–13:36 · Guest disagreement 0/10 Reflections on Fund One Fundraising Process Harry pushes Alexa to be self-critical about Fund I fundraising mistakes. Alexa explains the personal logistics of having a baby during the raise and then details her 50/50 reserve management and portfolio construction model.13:37–18:45 · Guest disagreement 3/10 Managing Follow-On Reserves and Aligning with Founders on Valuation Harry directly challenges Alexa on potential misalignment when investors price internal follow-on rounds and want lower valuations. Alexa firmly rejects the premise, arguing that true venture returns are made on selecting breakout winners rather than squeezing valuation margins.18:45–20:50 · Guest disagreement 1/10 Navigating Compressed Fundraising Timelines through Community Building Harry asks whether compressed fundraising timelines hinder building genuine founder relationships. Alexa outlines her proactive community-building strategy, including informal monthly dinners to meet founders well before rounds happen.21:03–24:24 · Guest disagreement 2/10 Personal Brand vs. Core Reputation in Venture Capital Harry admits his own difficulty in saying no to founders, prompting Alexa to deliver candid coaching. She advises him to 'lean into the pain' (LITTP) and build a fast, honest refusal muscle as a core duty of the job.24:29–30:04 · Guest disagreement 0/10 Mentorship Models and Partner Dynamics Harry asks about multi-generational mentorship models and whether co-founders can double as mentors. Alexa shares the origin stories of recruiting Penny Pritzker and Lucy Deland to co-found Inspired Capital.30:06–32:11 · Guest disagreement 0/10 The Growth and Potential of the New York Tech Ecosystem Harry offers an informed thesis that New York lacks genuine lead investors despite looking crowded. Alexa validates his point and supports it with a 12-to-1 capital disparity statistic comparing Silicon Valley to NYC per capita.32:11–35:48 · Guest disagreement 0/10 Quickfire Round: Books, Boards, and Recent Investments Harry conducts a standard quickfire round touching on books, board dynamics, and recent investments. Alexa shares takeaways from 'The Power of Moments' and her investment in Snackpass.2:45–4:46 · Harry pushing back 0/10 Alexa von Tobel's Journey from Entrepreneurship to Venture Capital Harry welcomes Alexa and asks a standard opening question about her transition from entrepreneur to angel investor and founder of Inspired Capital. Alexa shares her background starting from selling art as a kid to dropping out of HBS and founding LearnVest.4:46–8:55 · Harry pushing back 1/10 Transitioning Mindset from Angel Investor to Institutional Fund Manager Harry demonstrates industry knowledge by citing insights from Josh Koppelman and Andy McLaughlin regarding the mindset shift from angel to institutional investing. Alexa details how fiduciary duty sharpens investment decisions and outlines her team's background.8:55–13:36 · Harry pushing back 2/10 Reflections on Fund One Fundraising Process Harry pushes Alexa to be self-critical about Fund I fundraising mistakes. Alexa explains the personal logistics of having a baby during the raise and then details her 50/50 reserve management and portfolio construction model.13:37–18:45 · Harry pushing back 4/10 Managing Follow-On Reserves and Aligning with Founders on Valuation Harry directly challenges Alexa on potential misalignment when investors price internal follow-on rounds and want lower valuations. Alexa firmly rejects the premise, arguing that true venture returns are made on selecting breakout winners rather than squeezing valuation margins.18:45–20:50 · Harry pushing back 2/10 Navigating Compressed Fundraising Timelines through Community Building Harry asks whether compressed fundraising timelines hinder building genuine founder relationships. Alexa outlines her proactive community-building strategy, including informal monthly dinners to meet founders well before rounds happen.21:03–24:24 · Harry pushing back 1/10 Personal Brand vs. Core Reputation in Venture Capital Harry admits his own difficulty in saying no to founders, prompting Alexa to deliver candid coaching. She advises him to 'lean into the pain' (LITTP) and build a fast, honest refusal muscle as a core duty of the job.24:29–30:04 · Harry pushing back 0/10 Mentorship Models and Partner Dynamics Harry asks about multi-generational mentorship models and whether co-founders can double as mentors. Alexa shares the origin stories of recruiting Penny Pritzker and Lucy Deland to co-found Inspired Capital.30:06–32:11 · Harry pushing back 1/10 The Growth and Potential of the New York Tech Ecosystem Harry offers an informed thesis that New York lacks genuine lead investors despite looking crowded. Alexa validates his point and supports it with a 12-to-1 capital disparity statistic comparing Silicon Valley to NYC per capita.32:11–35:48 · Harry pushing back 0/10 Quickfire Round: Books, Boards, and Recent Investments Harry conducts a standard quickfire round touching on books, board dynamics, and recent investments. Alexa shares takeaways from 'The Power of Moments' and her investment in Snackpass.

speaking balance: gold is Harry, purple is the guest (3 minute bins)

0:00 · Harry 96.2% · guest 3.8%0:00 · Harry 96.2% · guest 3.8%3:00 · Harry 28% · guest 72%3:00 · Harry 28% · guest 72%6:00 · Harry 20.6% · guest 79.4%6:00 · Harry 20.6% · guest 79.4%9:00 · Harry 19.6% · guest 80.4%9:00 · Harry 19.6% · guest 80.4%12:00 · Harry 7.8% · guest 92.2%12:00 · Harry 7.8% · guest 92.2%15:00 · Harry 22.1% · guest 77.9%15:00 · Harry 22.1% · guest 77.9%18:00 · Harry 20.6% · guest 79.4%18:00 · Harry 20.6% · guest 79.4%21:00 · Harry 21.1% · guest 78.9%21:00 · Harry 21.1% · guest 78.9%24:00 · Harry 11.4% · guest 88.6%24:00 · Harry 11.4% · guest 88.6%27:00 · Harry 7% · guest 93%27:00 · Harry 7% · guest 93%30:00 · Harry 28.2% · guest 71.8%30:00 · Harry 28.2% · guest 71.8%33:00 · Harry 15.6% · guest 84.4%33:00 · Harry 15.6% · guest 84.4%36:00 · Harry 100% · guest 0%36:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 15:56 Alexa rejects valuation misalignment premise

Alexa directly rejects Harry's framing that pricing internal follow-on rounds creates core misalignment, asserting that venture returns are not made on squeezing a few million dollars in valuation.

 Hardest push from Harry ▶ 15:20 Harry pushes on investor vs founder valuation conflict

Harry presses Alexa on whether her founder-first mindset clashes with her investor responsibility when pricing rounds and attempting to cram down valuation for optimal ownership.

 Biggest teaching moment ▶ 23:30 Alexa coaches Harry on saying no

When Harry admits he struggles to turn founders down, Alexa takes on a mentor role, telling him to 'lean into the pain' and accept that saying no quickly and clearly is an essential skill.

 Harry holds his own ▶ 4:46 Harry cites top VC partners on mindset shift

Harry showcases his domain knowledge by quoting Josh Koppelman and Andy McLaughlin on how investor risk tolerance narrows when transitioning from angel to institutional fund management.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Alexa von Tobel's Journey from Entrepreneurship to Venture Capital 2100 Harry welcomes Alexa and asks a standard opening question about her transition from entrepreneur to angel investor and founder of Inspired Capital. Alexa shares her background starting from selling art as a kid to dropping out of HBS and founding LearnVest.
Transitioning Mindset from Angel Investor to Institutional Fund Manager 4201 Harry demonstrates industry knowledge by citing insights from Josh Koppelman and Andy McLaughlin regarding the mindset shift from angel to institutional investing. Alexa details how fiduciary duty sharpens investment decisions and outlines her team's background.
Reflections on Fund One Fundraising Process 3302 Harry pushes Alexa to be self-critical about Fund I fundraising mistakes. Alexa explains the personal logistics of having a baby during the raise and then details her 50/50 reserve management and portfolio construction model.
Managing Follow-On Reserves and Aligning with Founders on Valuation 5534 Harry directly challenges Alexa on potential misalignment when investors price internal follow-on rounds and want lower valuations. Alexa firmly rejects the premise, arguing that true venture returns are made on selecting breakout winners rather than squeezing valuation margins.
Navigating Compressed Fundraising Timelines through Community Building 3212 Harry asks whether compressed fundraising timelines hinder building genuine founder relationships. Alexa outlines her proactive community-building strategy, including informal monthly dinners to meet founders well before rounds happen.
Personal Brand vs. Core Reputation in Venture Capital 2621 Harry admits his own difficulty in saying no to founders, prompting Alexa to deliver candid coaching. She advises him to 'lean into the pain' (LITTP) and build a fast, honest refusal muscle as a core duty of the job.
Mentorship Models and Partner Dynamics 2200 Harry asks about multi-generational mentorship models and whether co-founders can double as mentors. Alexa shares the origin stories of recruiting Penny Pritzker and Lucy Deland to co-found Inspired Capital.
The Growth and Potential of the New York Tech Ecosystem 4301 Harry offers an informed thesis that New York lacks genuine lead investors despite looking crowded. Alexa validates his point and supports it with a 12-to-1 capital disparity statistic comparing Silicon Valley to NYC per capita.
Quickfire Round: Books, Boards, and Recent Investments 2100 Harry conducts a standard quickfire round touching on books, board dynamics, and recent investments. Alexa shares takeaways from 'The Power of Moments' and her investment in Snackpass.

Statements from this episode (12)

Assertion Partly supported
Alexa von Tobel Sold LearnVest for Approximately $375 Million
“Eventually LearnVest got acquired for about three hundred and seventy five million dollars”
Alexa von Tobel Jan 31, 2020 ▶ 4:22
Assertion Supported
Inspired Capital is the Largest Female-Led VC Firm in NYC History
“It's the largest ever female-led VC firm in New York.”
Harry Stebbings Jan 31, 2020 ▶ 6:15
Disclosure
Inspired Capital Closed $125 Million on Alexa von Tobel's First Day
“So my last day, as I transitioned off the management team at Northwestern Mutual, the firm, literally the last day that I left Northwestern Mutual and launched Inspired, it was the same day. And on that day, we closed about a hundred and twenty-five million.”
Alexa von Tobel Jan 31, 2020 ▶ 9:10
Disclosure
Inspired Capital Raised its Final $75 Million in 90 Days
“And then we finished the final seventy-five million over the summer, 90 days.”
Alexa von Tobel Jan 31, 2020 ▶ 9:48
Insight
Founders Should Fundraise in Early Year or Fall, Not Summer
“But it was just for us, our reality, and so we did it, and it ended up going really well, and you know, we got everything wrapped up, but I would just say in general, like fundraising, do it in the beginning of the year when people are super focused, do it in …”
Alexa von Tobel Jan 31, 2020 ▶ 10:00
Prediction Not checkable as stated
Inspired Capital Splits its $200M Fund 50/50 Between Initial Checks and Reserves
“So our fund is two hundred million. So for a two hundred million dollar fund, you know, we really do think about it as saving a sizable chunk, 50% for reserves, 50% for initial deployment.”
Alexa von Tobel Jan 31, 2020 ▶ 11:48
Insight
Venture Returns Come From Category Winners, Not Valuation Haggling
“Venture returns are not made on like a few million dollars evaluation. That in the end, it's about picking the breakout companies that are the category creating businesses of the next And making sure that you are at the table in a handful of those.”
Alexa von Tobel Jan 31, 2020 ▶ 16:03
Disclosure
LearnVest Could Have Raised Series B and C at $50M Higher Valuations
“When I was building LearnVest, there were times where I backed our series B and series C, where I could have pushed the valuation by about another fifty million dollars.”
Alexa von Tobel Jan 31, 2020 ▶ 17:51
Assertion Not checkable as stated
Alexa von Tobel Hosts Monthly No-Agenda Dinners for Entrepreneurs
“I once a month have a dinner where people come over to my apartment and we just totally with zero agenda talk about categories we're interested in.”
Alexa von Tobel Jan 31, 2020 ▶ 19:44
Disclosure
Penny Pritzker Co-Founded Inspired Capital With Alexa von Tobel
“I called her back, and she was like, I want to be your business partner. I want to found this with you. Let's go. Let's bring a multi-generational stage to this.”
Alexa von Tobel Jan 31, 2020 ▶ 29:06
Assertion Partly supported
Per Capita VC Funding in NYC is 1:12 Versus Silicon Valley
“There's one dollar here to 12 in the valley. That's the math per capita.”
Alexa von Tobel Jan 31, 2020 ▶ 30:49
Insight
Products Only Need One Extraordinary Moment for a Great Customer Experience
“We often try to make every part of the product development of a customer experience awesome. You just need one A++++ moment. That is then how the psychology works so that you end up having a great experience.”
Alexa von Tobel Jan 31, 2020 ▶ 32:26
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