StarZero All shows Try the podcast clipper →

Dec 7, 2016 · 33m · 20vc

20VC: How To Assess Founder Psychology, Why Talking About Financial Returns In The First Meeting Is Always Wrong & How To Allocate Time Amongst A VC Portfolio with Kara Nortman, Partner @ Upfront Ventures

Kara Nortman · 24m spoken Harry Stebbings · 7m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of The 20 Minute VC, host Harry Stebbings interviews Kara Nortman, Partner at Upfront Ventures, covering her career journey across tech and venture capital, effective board governance strategies, founder psychology evaluation, and methods for fostering diversity in the venture 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 25% of the talking time here. How this is scored →

Harry as informed peer 2.8 Guest teaching 2.7 Guest disagreement 0.8 Harry pushing back 1.0
05100:0010:0020:0030:002:39–9:01 · Harry as informed peer 1/10 Welcoming Kara Nortman and Her Career Journey Harry welcomes Kara and asks an open-ended career background question. Kara shares a detailed account of her path from Morgan Stanley to Battery Ventures, IAC, and Seedling in a completely collaborative tone.9:01–14:41 · Harry as informed peer 4/10 Understanding Board Dynamics and Building Board Chemistry Harry demonstrates familiarity with board governance by referencing guest Paul Barbarian's prep tactics and questioning whether investors can become 'too friendly' with founders. Kara provides nuanced advice on building authentic rapport while keeping business decisions primary.14:41–17:24 · Harry as informed peer 4/10 Portfolio Time Allocation and VC Support Strategies Harry demonstrates industry knowledge by framing the debate between spending time on portfolio 'unicorns' versus struggling companies. Kara explains her high-touch approach and belief in supporting companies through uncertain turnarounds.17:24–19:59 · Harry as informed peer 2/10 Assessing Founder Psychology and Resilience Harry asks Kara how she evaluates founder resilience across pre- and post-investment stages. Kara outlines her criteria, emphasizing personal stories and how founders handle adversity.19:59–27:23 · Harry as informed peer 4/10 Gender Diversity, Female VCs, and Board Inclusion When Harry asserts that data proves women are better investors, Kara politely checks him by pointing out that VC data is almost entirely anecdotal and asks him to share it if it exists. The rest of the discussion covers actionable steps for expanding gender diversity on private boards and within GP partnerships.27:23–31:14 · Harry as informed peer 2/10 Quickfire Round: Books, Red Flags, Mentors, and Latest Deal Harry enforces a structured 60-second quickfire round covering books, founder red flags, mentors, and recent investments. Kara concisely shares her perspectives, noting early exit discussions as a major red flag.2:39–9:01 · Guest teaching 1/10 Welcoming Kara Nortman and Her Career Journey Harry welcomes Kara and asks an open-ended career background question. Kara shares a detailed account of her path from Morgan Stanley to Battery Ventures, IAC, and Seedling in a completely collaborative tone.9:01–14:41 · Guest teaching 3/10 Understanding Board Dynamics and Building Board Chemistry Harry demonstrates familiarity with board governance by referencing guest Paul Barbarian's prep tactics and questioning whether investors can become 'too friendly' with founders. Kara provides nuanced advice on building authentic rapport while keeping business decisions primary.14:41–17:24 · Guest teaching 2/10 Portfolio Time Allocation and VC Support Strategies Harry demonstrates industry knowledge by framing the debate between spending time on portfolio 'unicorns' versus struggling companies. Kara explains her high-touch approach and belief in supporting companies through uncertain turnarounds.17:24–19:59 · Guest teaching 3/10 Assessing Founder Psychology and Resilience Harry asks Kara how she evaluates founder resilience across pre- and post-investment stages. Kara outlines her criteria, emphasizing personal stories and how founders handle adversity.19:59–27:23 · Guest teaching 5/10 Gender Diversity, Female VCs, and Board Inclusion When Harry asserts that data proves women are better investors, Kara politely checks him by pointing out that VC data is almost entirely anecdotal and asks him to share it if it exists. The rest of the discussion covers actionable steps for expanding gender diversity on private boards and within GP partnerships.27:23–31:14 · Guest teaching 2/10 Quickfire Round: Books, Red Flags, Mentors, and Latest Deal Harry enforces a structured 60-second quickfire round covering books, founder red flags, mentors, and recent investments. Kara concisely shares her perspectives, noting early exit discussions as a major red flag.2:39–9:01 · Guest disagreement 0/10 Welcoming Kara Nortman and Her Career Journey Harry welcomes Kara and asks an open-ended career background question. Kara shares a detailed account of her path from Morgan Stanley to Battery Ventures, IAC, and Seedling in a completely collaborative tone.9:01–14:41 · Guest disagreement 1/10 Understanding Board Dynamics and Building Board Chemistry Harry demonstrates familiarity with board governance by referencing guest Paul Barbarian's prep tactics and questioning whether investors can become 'too friendly' with founders. Kara provides nuanced advice on building authentic rapport while keeping business decisions primary.14:41–17:24 · Guest disagreement 1/10 Portfolio Time Allocation and VC Support Strategies Harry demonstrates industry knowledge by framing the debate between spending time on portfolio 'unicorns' versus struggling companies. Kara explains her high-touch approach and belief in supporting companies through uncertain turnarounds.17:24–19:59 · Guest disagreement 0/10 Assessing Founder Psychology and Resilience Harry asks Kara how she evaluates founder resilience across pre- and post-investment stages. Kara outlines her criteria, emphasizing personal stories and how founders handle adversity.19:59–27:23 · Guest disagreement 3/10 Gender Diversity, Female VCs, and Board Inclusion When Harry asserts that data proves women are better investors, Kara politely checks him by pointing out that VC data is almost entirely anecdotal and asks him to share it if it exists. The rest of the discussion covers actionable steps for expanding gender diversity on private boards and within GP partnerships.27:23–31:14 · Guest disagreement 0/10 Quickfire Round: Books, Red Flags, Mentors, and Latest Deal Harry enforces a structured 60-second quickfire round covering books, founder red flags, mentors, and recent investments. Kara concisely shares her perspectives, noting early exit discussions as a major red flag.2:39–9:01 · Harry pushing back 0/10 Welcoming Kara Nortman and Her Career Journey Harry welcomes Kara and asks an open-ended career background question. Kara shares a detailed account of her path from Morgan Stanley to Battery Ventures, IAC, and Seedling in a completely collaborative tone.9:01–14:41 · Harry pushing back 2/10 Understanding Board Dynamics and Building Board Chemistry Harry demonstrates familiarity with board governance by referencing guest Paul Barbarian's prep tactics and questioning whether investors can become 'too friendly' with founders. Kara provides nuanced advice on building authentic rapport while keeping business decisions primary.14:41–17:24 · Harry pushing back 1/10 Portfolio Time Allocation and VC Support Strategies Harry demonstrates industry knowledge by framing the debate between spending time on portfolio 'unicorns' versus struggling companies. Kara explains her high-touch approach and belief in supporting companies through uncertain turnarounds.17:24–19:59 · Harry pushing back 0/10 Assessing Founder Psychology and Resilience Harry asks Kara how she evaluates founder resilience across pre- and post-investment stages. Kara outlines her criteria, emphasizing personal stories and how founders handle adversity.19:59–27:23 · Harry pushing back 2/10 Gender Diversity, Female VCs, and Board Inclusion When Harry asserts that data proves women are better investors, Kara politely checks him by pointing out that VC data is almost entirely anecdotal and asks him to share it if it exists. The rest of the discussion covers actionable steps for expanding gender diversity on private boards and within GP partnerships.27:23–31:14 · Harry pushing back 1/10 Quickfire Round: Books, Red Flags, Mentors, and Latest Deal Harry enforces a structured 60-second quickfire round covering books, founder red flags, mentors, and recent investments. Kara concisely shares her perspectives, noting early exit discussions as a major red flag.

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

0:00 · Harry 100% · guest 0%0:00 · Harry 100% · guest 0%3:00 · Harry 4.8% · guest 95.2%3:00 · Harry 4.8% · guest 95.2%6:00 · Harry 0% · guest 100%6:00 · Harry 0% · guest 100%9:00 · Harry 28.2% · guest 71.8%9:00 · Harry 28.2% · guest 71.8%12:00 · Harry 15.9% · guest 84.1%12:00 · Harry 15.9% · guest 84.1%15:00 · Harry 18.5% · guest 81.5%15:00 · Harry 18.5% · guest 81.5%18:00 · Harry 12.3% · guest 87.7%18:00 · Harry 12.3% · guest 87.7%21:00 · Harry 8.7% · guest 91.3%21:00 · Harry 8.7% · guest 91.3%24:00 · Harry 0% · guest 100%24:00 · Harry 0% · guest 100%27:00 · Harry 9.6% · guest 90.4%27:00 · Harry 9.6% · guest 90.4%30:00 · Harry 59.1% · guest 40.9%30:00 · Harry 59.1% · guest 40.9%33:00 · Harry 100% · guest 0%33:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 22:14 Kara gently challenges host's data claim

When Harry asserts that data shows women are superior investors, Kara directly challenges the premise by noting venture capital data is almost exclusively anecdotal and asks him to provide proof.

 Hardest push from Harry ▶ 13:04 Harry challenges the boundary of personal closeness on boards

Harry pushes back on Kara's recommendation of taking significant others out for meals by asking if board members can cross professional boundaries and become too friendly with founders.

 Biggest teaching moment ▶ 22:14 Kara corrects host on venture capital data limitations

Kara educates Harry on the nature of venture capital research, explaining that claims regarding investor performance are largely based on anecdote rather than hard empirical data.

 Harry holds his own ▶ 14:41 Harry cites contrasting venture portfolio strategies

Harry demonstrates domain expertise by contrasting the strategy of helping struggling companies against the widely held VC philosophy of doubling down exclusively on outlier portfolio unicorns.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Welcoming Kara Nortman and Her Career Journey 1100 Harry welcomes Kara and asks an open-ended career background question. Kara shares a detailed account of her path from Morgan Stanley to Battery Ventures, IAC, and Seedling in a completely collaborative tone.
Understanding Board Dynamics and Building Board Chemistry 4312 Harry demonstrates familiarity with board governance by referencing guest Paul Barbarian's prep tactics and questioning whether investors can become 'too friendly' with founders. Kara provides nuanced advice on building authentic rapport while keeping business decisions primary.
Portfolio Time Allocation and VC Support Strategies 4211 Harry demonstrates industry knowledge by framing the debate between spending time on portfolio 'unicorns' versus struggling companies. Kara explains her high-touch approach and belief in supporting companies through uncertain turnarounds.
Assessing Founder Psychology and Resilience 2300 Harry asks Kara how she evaluates founder resilience across pre- and post-investment stages. Kara outlines her criteria, emphasizing personal stories and how founders handle adversity.
Gender Diversity, Female VCs, and Board Inclusion 4532 When Harry asserts that data proves women are better investors, Kara politely checks him by pointing out that VC data is almost entirely anecdotal and asks him to share it if it exists. The rest of the discussion covers actionable steps for expanding gender diversity on private boards and within GP partnerships.
Quickfire Round: Books, Red Flags, Mentors, and Latest Deal 2201 Harry enforces a structured 60-second quickfire round covering books, founder red flags, mentors, and recent investments. Kara concisely shares her perspectives, noting early exit discussions as a major red flag.

Statements from this episode (6)

Assertion Partly supported
Nortman recruited Sean Rad to IAC before he created Tinder
“I went in and recruited Sean Radd into IAC and gave him his first business plan, which turned into something completely different. It wasn't Tinder. He took it and very much made it his own, but it was something I got involved with the day-to-day of in the fir…”
Kara Nortman Dec 7, 2016 ▶ 8:36
Insight
Nortman: Selecting board members for brand over chemistry is a founder mistake
“I think this is a mistake a lot of people make as founders, which is to try to get the biggest names or something that they think is sort of like a brand of a particular board member without really doing a lot of work to make sure that you have the right chemi…”
Kara Nortman Dec 7, 2016 ▶ 9:44
Opinion
Nortman: Deal picking accounts for at least 50% of VC value creation
“I definitely think the picking is 50% or more, but I very much believe in the doing”
Kara Nortman Dec 7, 2016 ▶ 16:18
Disclosure
Nortman: Upfront partners only invest in about two new companies per year
“We only invest in about two companies a year.”
Kara Nortman Dec 7, 2016 ▶ 16:50
Insight
Nortman: Board seats drive gender diversity faster than VC partner roles
“I think that's the fastest place to make change, getting more women into venture roles, into, you know, kind of real decision-making GP roles in firms that can write real check is another one. It seems like that takes longer than changing the board, but both o…”
Kara Nortman Dec 7, 2016 ▶ 24:32
Opinion
Kara Nortman: Founders focusing on exits in first pitch are a red flag
“Somebody who's talking about exit in the first meeting. And I should say not, and not exit in terms of, you know, because we may ask that sometimes, hey, where does this go? What happens? Who do you think might this might be a part of someday more like they're…”
Kara Nortman Dec 7, 2016 ▶ 28:20
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 1,200 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more