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May 24, 2017 · 26m · 20vc

20VC: The Biggest Indicators Of Success In Founding Teams, How To Balance Both Vision and Operations & Taking Money From "The Man At The Rug Store" with Mar Hershenson, Founding Managing Partner @ Pear.vc

Mar Hershenson · 16m spoken Harry Stebbings · 8m spoken
0:00 / 0:00

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In this episode of The 20 Minute VC, host Harry Stebbings interviews Mar Hershenson, Founding Managing Partner at Pear VC, about her transition from Stanford engineer to venture capitalist. Hershenson shares key insights on founder evaluation, balancing long-term vision with operational discipline, early-stage acceleration, and the unique partnership dynamic behind Pear VC.

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 34.3% of the talking time here. How this is scored →

Harry as informed peer 2.5 Guest teaching 2.0 Guest disagreement 0.0 Harry pushing back 0.0
05100:0010:0020:002:37–5:37 · Harry as informed peer 1/10 Mar Hershenson's Origin Story in Venture Capital Harry welcomes Mar and asks about her background transitioning from a Stanford engineering background to venture capital, followed by a warm inquiry about Pear VC's Launchpad program. Mar describes how Pejman recruited her and how Launchpad organically grew out of informal mentoring for Stanford students.5:37–8:24 · Harry as informed peer 3/10 Evaluating Early-Stage Founders and the Role of VC Platforms Harry references questions from portfolio founders regarding early-stage founder selection and asks if platform offerings represent the future of venture capital amid capital commoditization. Mar explains that Pear focuses on evaluating raw human drive before product traction and clarifies that VC platform services remain an intensive human service rather than an easily automated product.8:24–12:15 · Harry as informed peer 3/10 Balancing Vision with Operational Rigor and Defining Key Metrics Harry asks how founders should balance vision with operational rigor and how investors determine key progress metrics. Mar emphasizes that great founders tackle their hardest risks first rather than comfortable tasks, and notes that concise founder communication is a key indicator of future success.12:15–15:10 · Harry as informed peer 3/10 Series A Benchmarks and the Story of Danger's Seed Investment Harry cites SaaS investor Jason Lemkin regarding Series A benchmarks, which Mar nuances by explaining that category-defining startups often lack clear metrics benchmarks. Mar then shares the memorable story of Danger raising its early seed capital from Pejman at his rug store in 1999 when traditional Sand Hill Road firms rejected them.15:10–20:57 · Harry as informed peer 3/10 The Pear VC Partnership Dynamic, Board Involvement, and Portfolio Management Harry explores the dynamics of Pear's two-person partnership, asking about role segmentation, board seat management, and scaling limited time. Mar explains that she and Pejman operate interchangeably with shared core goals, and notes that seed board commitments naturally rotate off after 18 to 24 months as companies reach Series A.20:57–24:27 · Harry as informed peer 2/10 Quickfire Round with Mar Hershenson Harry conducts a quickfire round covering favorite books, firm vision, life advice, top blogs, time management challenges, and Pear's recent backing of Nova Credit. Mar shares thoughtful, concise answers in a lighthearted exchange.2:37–5:37 · Guest teaching 1/10 Mar Hershenson's Origin Story in Venture Capital Harry welcomes Mar and asks about her background transitioning from a Stanford engineering background to venture capital, followed by a warm inquiry about Pear VC's Launchpad program. Mar describes how Pejman recruited her and how Launchpad organically grew out of informal mentoring for Stanford students.5:37–8:24 · Guest teaching 2/10 Evaluating Early-Stage Founders and the Role of VC Platforms Harry references questions from portfolio founders regarding early-stage founder selection and asks if platform offerings represent the future of venture capital amid capital commoditization. Mar explains that Pear focuses on evaluating raw human drive before product traction and clarifies that VC platform services remain an intensive human service rather than an easily automated product.8:24–12:15 · Guest teaching 2/10 Balancing Vision with Operational Rigor and Defining Key Metrics Harry asks how founders should balance vision with operational rigor and how investors determine key progress metrics. Mar emphasizes that great founders tackle their hardest risks first rather than comfortable tasks, and notes that concise founder communication is a key indicator of future success.12:15–15:10 · Guest teaching 3/10 Series A Benchmarks and the Story of Danger's Seed Investment Harry cites SaaS investor Jason Lemkin regarding Series A benchmarks, which Mar nuances by explaining that category-defining startups often lack clear metrics benchmarks. Mar then shares the memorable story of Danger raising its early seed capital from Pejman at his rug store in 1999 when traditional Sand Hill Road firms rejected them.15:10–20:57 · Guest teaching 3/10 The Pear VC Partnership Dynamic, Board Involvement, and Portfolio Management Harry explores the dynamics of Pear's two-person partnership, asking about role segmentation, board seat management, and scaling limited time. Mar explains that she and Pejman operate interchangeably with shared core goals, and notes that seed board commitments naturally rotate off after 18 to 24 months as companies reach Series A.20:57–24:27 · Guest teaching 1/10 Quickfire Round with Mar Hershenson Harry conducts a quickfire round covering favorite books, firm vision, life advice, top blogs, time management challenges, and Pear's recent backing of Nova Credit. Mar shares thoughtful, concise answers in a lighthearted exchange.2:37–5:37 · Guest disagreement 0/10 Mar Hershenson's Origin Story in Venture Capital Harry welcomes Mar and asks about her background transitioning from a Stanford engineering background to venture capital, followed by a warm inquiry about Pear VC's Launchpad program. Mar describes how Pejman recruited her and how Launchpad organically grew out of informal mentoring for Stanford students.5:37–8:24 · Guest disagreement 0/10 Evaluating Early-Stage Founders and the Role of VC Platforms Harry references questions from portfolio founders regarding early-stage founder selection and asks if platform offerings represent the future of venture capital amid capital commoditization. Mar explains that Pear focuses on evaluating raw human drive before product traction and clarifies that VC platform services remain an intensive human service rather than an easily automated product.8:24–12:15 · Guest disagreement 0/10 Balancing Vision with Operational Rigor and Defining Key Metrics Harry asks how founders should balance vision with operational rigor and how investors determine key progress metrics. Mar emphasizes that great founders tackle their hardest risks first rather than comfortable tasks, and notes that concise founder communication is a key indicator of future success.12:15–15:10 · Guest disagreement 0/10 Series A Benchmarks and the Story of Danger's Seed Investment Harry cites SaaS investor Jason Lemkin regarding Series A benchmarks, which Mar nuances by explaining that category-defining startups often lack clear metrics benchmarks. Mar then shares the memorable story of Danger raising its early seed capital from Pejman at his rug store in 1999 when traditional Sand Hill Road firms rejected them.15:10–20:57 · Guest disagreement 0/10 The Pear VC Partnership Dynamic, Board Involvement, and Portfolio Management Harry explores the dynamics of Pear's two-person partnership, asking about role segmentation, board seat management, and scaling limited time. Mar explains that she and Pejman operate interchangeably with shared core goals, and notes that seed board commitments naturally rotate off after 18 to 24 months as companies reach Series A.20:57–24:27 · Guest disagreement 0/10 Quickfire Round with Mar Hershenson Harry conducts a quickfire round covering favorite books, firm vision, life advice, top blogs, time management challenges, and Pear's recent backing of Nova Credit. Mar shares thoughtful, concise answers in a lighthearted exchange.2:37–5:37 · Harry pushing back 0/10 Mar Hershenson's Origin Story in Venture Capital Harry welcomes Mar and asks about her background transitioning from a Stanford engineering background to venture capital, followed by a warm inquiry about Pear VC's Launchpad program. Mar describes how Pejman recruited her and how Launchpad organically grew out of informal mentoring for Stanford students.5:37–8:24 · Harry pushing back 0/10 Evaluating Early-Stage Founders and the Role of VC Platforms Harry references questions from portfolio founders regarding early-stage founder selection and asks if platform offerings represent the future of venture capital amid capital commoditization. Mar explains that Pear focuses on evaluating raw human drive before product traction and clarifies that VC platform services remain an intensive human service rather than an easily automated product.8:24–12:15 · Harry pushing back 0/10 Balancing Vision with Operational Rigor and Defining Key Metrics Harry asks how founders should balance vision with operational rigor and how investors determine key progress metrics. Mar emphasizes that great founders tackle their hardest risks first rather than comfortable tasks, and notes that concise founder communication is a key indicator of future success.12:15–15:10 · Harry pushing back 0/10 Series A Benchmarks and the Story of Danger's Seed Investment Harry cites SaaS investor Jason Lemkin regarding Series A benchmarks, which Mar nuances by explaining that category-defining startups often lack clear metrics benchmarks. Mar then shares the memorable story of Danger raising its early seed capital from Pejman at his rug store in 1999 when traditional Sand Hill Road firms rejected them.15:10–20:57 · Harry pushing back 0/10 The Pear VC Partnership Dynamic, Board Involvement, and Portfolio Management Harry explores the dynamics of Pear's two-person partnership, asking about role segmentation, board seat management, and scaling limited time. Mar explains that she and Pejman operate interchangeably with shared core goals, and notes that seed board commitments naturally rotate off after 18 to 24 months as companies reach Series A.20:57–24:27 · Harry pushing back 0/10 Quickfire Round with Mar Hershenson Harry conducts a quickfire round covering favorite books, firm vision, life advice, top blogs, time management challenges, and Pear's recent backing of Nova Credit. Mar shares thoughtful, concise answers in a lighthearted exchange.

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

0:00 · Harry 92.8% · guest 7.2%0:00 · Harry 92.8% · guest 7.2%3:00 · Harry 20.9% · guest 79.1%3:00 · Harry 20.9% · guest 79.1%6:00 · Harry 24.8% · guest 75.2%6:00 · Harry 24.8% · guest 75.2%9:00 · Harry 18.5% · guest 81.5%9:00 · Harry 18.5% · guest 81.5%12:00 · Harry 26.4% · guest 73.6%12:00 · Harry 26.4% · guest 73.6%15:00 · Harry 15.9% · guest 84.1%15:00 · Harry 15.9% · guest 84.1%18:00 · Harry 21.6% · guest 78.4%18:00 · Harry 21.6% · guest 78.4%21:00 · Harry 20.3% · guest 79.7%21:00 · Harry 20.3% · guest 79.7%24:00 · Harry 85% · guest 15%24:00 · Harry 85% · guest 15%
Sharpest disagreement ▶ 12:36 Nuancing the applicability of Series A benchmarks

In an entirely agreeable interview, Mar offers the mildest reframe by noting that while standard benchmarks exist for most companies, truly revolutionary startups defy conventional metrics.

 Hardest push from Harry ▶ 17:47 Questioning role differentiation in a two-person firm

Harry presses on how a tight two-partner firm can function effectively without formal role specialization like larger institutional VC partnerships.

 Biggest teaching moment ▶ 20:25 Educating on seed versus Series A board time commitments

Mar educates Harry on the time math of seed investing, pointing out that seed board involvement typically sunsets after 18 to 24 months, unlike the 5 to 8 year horizon of Series A investors.

 Harry holds his own ▶ 12:15 Citing Jason Lemkin on SaaS follow-on benchmarks

Harry displays sharp domain knowledge by invoking SaaS expert Jason Lemkin's standard regarding follow-on fundraising benchmarks.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Mar Hershenson's Origin Story in Venture Capital 1100 Harry welcomes Mar and asks about her background transitioning from a Stanford engineering background to venture capital, followed by a warm inquiry about Pear VC's Launchpad program. Mar describes how Pejman recruited her and how Launchpad organically grew out of informal mentoring for Stanford students.
Evaluating Early-Stage Founders and the Role of VC Platforms 3200 Harry references questions from portfolio founders regarding early-stage founder selection and asks if platform offerings represent the future of venture capital amid capital commoditization. Mar explains that Pear focuses on evaluating raw human drive before product traction and clarifies that VC platform services remain an intensive human service rather than an easily automated product.
Balancing Vision with Operational Rigor and Defining Key Metrics 3200 Harry asks how founders should balance vision with operational rigor and how investors determine key progress metrics. Mar emphasizes that great founders tackle their hardest risks first rather than comfortable tasks, and notes that concise founder communication is a key indicator of future success.
Series A Benchmarks and the Story of Danger's Seed Investment 3300 Harry cites SaaS investor Jason Lemkin regarding Series A benchmarks, which Mar nuances by explaining that category-defining startups often lack clear metrics benchmarks. Mar then shares the memorable story of Danger raising its early seed capital from Pejman at his rug store in 1999 when traditional Sand Hill Road firms rejected them.
The Pear VC Partnership Dynamic, Board Involvement, and Portfolio Management 3300 Harry explores the dynamics of Pear's two-person partnership, asking about role segmentation, board seat management, and scaling limited time. Mar explains that she and Pejman operate interchangeably with shared core goals, and notes that seed board commitments naturally rotate off after 18 to 24 months as companies reach Series A.
Quickfire Round with Mar Hershenson 2100 Harry conducts a quickfire round covering favorite books, firm vision, life advice, top blogs, time management challenges, and Pear's recent backing of Nova Credit. Mar shares thoughtful, concise answers in a lighthearted exchange.

Statements from this episode (10)

Assertion Supported
11 of 13 Pear Launchpad Companies Raised Top 2016 Seed Rounds
“So, you know, last year we had about 13 companies 11 of them ended up raising a seed round from great people. Accel, first round, Index, just really, really top name people. And the other two went back to school.”
Mar Hershenson May 24, 2017 ▶ 5:17
Disclosure
Pear VC Evaluates Pre-Product Founders Solely on Obsession and Drive
“And the only thing we're judging is the human being, and the founder, and whether we think they are obsessed, hungry to achieve something.”
Mar Hershenson May 24, 2017 ▶ 6:27
Insight
VC Platforms Are Intensive Service Operations Scaling via People, Not Software
“At the end of the day, to be honest, what we do is, you know, you can automate and replicate some of it, but it's a very intensive services business, right? It's people. Everybody's different. Founder has a problem, and they really need that human contact with…”
Mar Hershenson May 24, 2017 ▶ 7:56
Insight
Startups Succeed Only by Tackling Their Hardest Problem First
“I think as a founder, you can always be busy, but the only thing that matters is the hardest thing. And a lot of many founders will tend not to do the hard things first. Right. They want to like, it's because you feel more comfortable doing the easy things fir…”
Mar Hershenson May 24, 2017 ▶ 10:17
Insight
Concise Founder Communication Is a Top Predictor of Startup Success
“But again, I think it's almost the way the CEO or the founding team communicates. It's a great predictor of success. And again, I think being a good communicator, it's obvious, but the people that are concise and size and they come to a meeting and they're lik…”
Mar Hershenson May 24, 2017 ▶ 11:41
Insight
Only 1 in 100 Startup Pitches Generates Strong Investment Conviction
“You meet a hundred companies, and 95 of them, you know, it's a clear no, four of them, it's like, maybe, and one of them, you're like, oh my god, I gotta do it”
Mar Hershenson May 24, 2017 ▶ 17:07
Assertion Not publicly verifiable
Seed Startups Without Lead VCs Struggle to Raise Series A Funding
“A seed company that maybe, you know, angel funded and has some sort of party round and there's no clear lead venture person has a much lower chance of getting to a series A than a company that has a lead seed fund behind it.”
Mar Hershenson May 24, 2017 ▶ 19:16
Assertion Supported
Active Seed Fund Involvement Typically Lasts 18 to 24 Months
“The nature of seed is such that they're around for 18 to 24 months, right? It could be less, it could be more, but on average, that's the number.”
Mar Hershenson May 24, 2017 ▶ 20:48
Opinion
Elad Gil's Blog Is Top-Tier Because Every Post Is Dense With Truth
“I mean, every piece that he writes is like, so dense with knowledge and truth. So I think he's, definitely. Definitely. That would be my number one”
Mar Hershenson May 24, 2017 ▶ 22:36
Disclosure
Pear VC Invested in Nova Credit Before It Had a Product
“We invested before there was a product. There were students at Stanford and they were coming here to our lectures or talks, et cetera. Just an amazing team.”
Mar Hershenson May 24, 2017 ▶ 24:06
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