StarZero All shows Try the podcast clipper →

Feb 5, 2018 · 25m · 20vc

20VC: Why Vulnerability Is A Strength In VC, 3 Core Components That Make The Most Successful VCs & How VCs and Entrepreneurs Can Build Meaningful Relationships Pre-Investment with Brian Garrett, Founding Partner @ Crosscut Ventures

Brian Garrett · 16m 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, Harry Stebbings interviews Brian Garrett, Founding Partner and Managing Director at Crosscut Ventures. Brian discusses the growth of Crosscut in Southern California while advocating for humility, vulnerability, and authentic relationship-building as core strengths in venture capital and startup leadership.

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 32.3% of the talking time here. How this is scored →

Harry as informed peer 3.2 Guest teaching 2.2 Guest disagreement 0.8 Harry pushing back 1.6
05100:0010:0020:002:25–5:27 · Harry as informed peer 2/10 Brian Garrett's Transition to VC and the Founding of Crosscut Harry asks an open-ended career origin question. Brian details his transition from Silicon Valley to LA and how early dealflow constraints led to founding Crosscut.5:27–9:17 · Harry as informed peer 4/10 Silicon Valley Dynamics vs. Building in Southern California Harry brings up prominent VCs like Peter Fenton and Brad Feld to discuss humility, then pushes back on whether tier-one VC ego creates desirable exclusivity for founders.9:17–13:42 · Harry as informed peer 3/10 Vulnerability as a Strength in Startup Leadership Harry challenges the humility paradigm by raising the Steve Jobs archetype and pointing out the real-world risks of PR leaks when founders show vulnerability.13:42–19:14 · Harry as informed peer 4/10 Fostering Authentic Founder-VC Relationships Pre-Investment Harry cites partner Fred's board intimacy concept and probes whether today's hyper-competitive deal speeds prevent proper pre-investment relationship building.19:16–23:58 · Harry as informed peer 3/10 Quick Fire Round with Brian Garrett Harry guides a fast-paced quickfire round covering personal philosophy, tough fundraises, and memorable LP meetings.2:25–5:27 · Guest teaching 3/10 Brian Garrett's Transition to VC and the Founding of Crosscut Harry asks an open-ended career origin question. Brian details his transition from Silicon Valley to LA and how early dealflow constraints led to founding Crosscut.5:27–9:17 · Guest teaching 2/10 Silicon Valley Dynamics vs. Building in Southern California Harry brings up prominent VCs like Peter Fenton and Brad Feld to discuss humility, then pushes back on whether tier-one VC ego creates desirable exclusivity for founders.9:17–13:42 · Guest teaching 3/10 Vulnerability as a Strength in Startup Leadership Harry challenges the humility paradigm by raising the Steve Jobs archetype and pointing out the real-world risks of PR leaks when founders show vulnerability.13:42–19:14 · Guest teaching 2/10 Fostering Authentic Founder-VC Relationships Pre-Investment Harry cites partner Fred's board intimacy concept and probes whether today's hyper-competitive deal speeds prevent proper pre-investment relationship building.19:16–23:58 · Guest teaching 1/10 Quick Fire Round with Brian Garrett Harry guides a fast-paced quickfire round covering personal philosophy, tough fundraises, and memorable LP meetings.2:25–5:27 · Guest disagreement 1/10 Brian Garrett's Transition to VC and the Founding of Crosscut Harry asks an open-ended career origin question. Brian details his transition from Silicon Valley to LA and how early dealflow constraints led to founding Crosscut.5:27–9:17 · Guest disagreement 1/10 Silicon Valley Dynamics vs. Building in Southern California Harry brings up prominent VCs like Peter Fenton and Brad Feld to discuss humility, then pushes back on whether tier-one VC ego creates desirable exclusivity for founders.9:17–13:42 · Guest disagreement 1/10 Vulnerability as a Strength in Startup Leadership Harry challenges the humility paradigm by raising the Steve Jobs archetype and pointing out the real-world risks of PR leaks when founders show vulnerability.13:42–19:14 · Guest disagreement 1/10 Fostering Authentic Founder-VC Relationships Pre-Investment Harry cites partner Fred's board intimacy concept and probes whether today's hyper-competitive deal speeds prevent proper pre-investment relationship building.19:16–23:58 · Guest disagreement 0/10 Quick Fire Round with Brian Garrett Harry guides a fast-paced quickfire round covering personal philosophy, tough fundraises, and memorable LP meetings.2:25–5:27 · Harry pushing back 0/10 Brian Garrett's Transition to VC and the Founding of Crosscut Harry asks an open-ended career origin question. Brian details his transition from Silicon Valley to LA and how early dealflow constraints led to founding Crosscut.5:27–9:17 · Harry pushing back 3/10 Silicon Valley Dynamics vs. Building in Southern California Harry brings up prominent VCs like Peter Fenton and Brad Feld to discuss humility, then pushes back on whether tier-one VC ego creates desirable exclusivity for founders.9:17–13:42 · Harry pushing back 3/10 Vulnerability as a Strength in Startup Leadership Harry challenges the humility paradigm by raising the Steve Jobs archetype and pointing out the real-world risks of PR leaks when founders show vulnerability.13:42–19:14 · Harry pushing back 2/10 Fostering Authentic Founder-VC Relationships Pre-Investment Harry cites partner Fred's board intimacy concept and probes whether today's hyper-competitive deal speeds prevent proper pre-investment relationship building.19:16–23:58 · Harry pushing back 0/10 Quick Fire Round with Brian Garrett Harry guides a fast-paced quickfire round covering personal philosophy, tough fundraises, and memorable LP meetings.

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

0:00 · Harry 88.6% · guest 11.4%0:00 · Harry 88.6% · guest 11.4%3:00 · Harry 6.1% · guest 93.9%3:00 · Harry 6.1% · guest 93.9%6:00 · Harry 25.9% · guest 74.1%6:00 · Harry 25.9% · guest 74.1%9:00 · Harry 17.1% · guest 82.9%9:00 · Harry 17.1% · guest 82.9%12:00 · Harry 30.3% · guest 69.7%12:00 · Harry 30.3% · guest 69.7%15:00 · Harry 17.9% · guest 82.1%15:00 · Harry 17.9% · guest 82.1%18:00 · Harry 22.4% · guest 77.6%18:00 · Harry 22.4% · guest 77.6%21:00 · Harry 13.5% · guest 86.5%21:00 · Harry 13.5% · guest 86.5%24:00 · Harry 100% · guest 0%24:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 9:30 Brian redefines strength against the Steve Jobs archetype

Brian directly counters the notion that arrogant brute force is necessary for success, reframing true modern leadership around servant leadership and culture.

 Hardest push from Harry ▶ 8:26 Harry questions the utility of VC ego

Harry challenges Brian's emphasis on humility by asking if premier VCs' ego creates a sense of hard-to-get desirability for founders.

 Biggest teaching moment ▶ 10:00 Brian breaks down confidence versus arrogance using Brene Brown

Brian educates the host on psychological safety, drawing from Dr. Brene Brown to explain how vulnerability functions as ultimate strength in leadership.

 Harry holds his own ▶ 8:26 Harry cites top tier VCs to challenge guest narrative

Harry shows strong industry context by referencing elite investors like Peter Fenton and questioning whether arrogance serves as an effective signal in VC.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Brian Garrett's Transition to VC and the Founding of Crosscut 2310 Harry asks an open-ended career origin question. Brian details his transition from Silicon Valley to LA and how early dealflow constraints led to founding Crosscut.
Silicon Valley Dynamics vs. Building in Southern California 4213 Harry brings up prominent VCs like Peter Fenton and Brad Feld to discuss humility, then pushes back on whether tier-one VC ego creates desirable exclusivity for founders.
Vulnerability as a Strength in Startup Leadership 3313 Harry challenges the humility paradigm by raising the Steve Jobs archetype and pointing out the real-world risks of PR leaks when founders show vulnerability.
Fostering Authentic Founder-VC Relationships Pre-Investment 4212 Harry cites partner Fred's board intimacy concept and probes whether today's hyper-competitive deal speeds prevent proper pre-investment relationship building.
Quick Fire Round with Brian Garrett 3100 Harry guides a fast-paced quickfire round covering personal philosophy, tough fundraises, and memorable LP meetings.

Statements from this episode (6)

Assertion Supported
Crosscut Ventures raised $75M for Fund III and $125M in 2017
“Which enabled Crosscut to really scale into a fund with seventy five million dollars raised for Crosscut three. This has then snowballed to their latest fund raised in December, 2017, being one hundred and twenty five million dollars.”
Harry Stebbings Feb 5, 2018 ▶ 0:55
Opinion
Brian Garrett: The venture capital industry is driven by ego and greed
“Industry generally is driven by ego and greed, and I think it brings out some of the bad side of humanity.”
Brian Garrett Feb 5, 2018 ▶ 7:08
Prediction Held up
Brian Garrett limits his investment cadence to two or three deals annually
“I only try to do two or three deals a year.”
Brian Garrett Feb 5, 2018 ▶ 15:19
Insight
Brian Garrett: Venture capital success mostly comes down to luck and timing
“Because at the end of the day, most of this is about luck and timing.”
Brian Garrett Feb 5, 2018 ▶ 16:02
Insight
Brian Garrett: Young VCs speak in board meetings just to feel important
“I have found that the biggest issue I've seen is young VCs believing that they have to speak because they're tasked as a board member, and they're supposed to say important things, and my philosophy is speak when you have something to say, not because you want…”
Brian Garrett Feb 5, 2018 ▶ 17:35
Disclosure
Brian Garrett: LPs doubted Southern California was a real market in 2014
“I think that the most challenging... For us was the first thirty million of Crosscut Three, what we were calling our first close. And it was late in 2014 and not so clear that Southern California was a quote, real market to LPs yet.”
Brian Garrett Feb 5, 2018 ▶ 21:07
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