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Sep 7, 2016 · 28m · 20vc

20VC: What Is Wrong With The VC Industry, Why VC Is A Customer Service Game and Why Car Ownership Will Be A Thing Of The Past with Brett DeMarrais, Partner @ Ludlow Ventures

Brett DeMarrais · 19m 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 Brett DeMarrais, Partner at Ludlow Ventures, who reflects on his transition from founder burnout to venture capital. Brett discusses what true 'founder-first' investing entails, how empathy drives long-term returns, and his investment thesis on autonomous vehicles.

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 29.2% of the talking time here. How this is scored →

Harry as informed peer 3.5 Guest teaching 2.5 Guest disagreement 0.8 Harry pushing back 1.7
05100:0010:0020:002:11–4:19 · Harry as informed peer 2/10 Brett DeMarrais's Journey into Venture Capital Harry asks a standard conversational question about Brett's career entry and offers light, encouraging banter about his potential as an investor. Brett warmly details his transition from his startup Wedit to joining Ludlow Ventures alongside Jonathan Triest.4:19–7:13 · Harry as informed peer 3/10 Founder Struggles and Early Entrepreneurial Lessons Harry opens up about his own early business struggles to set up an empathetic prompt on founder resilience. Brett responds candidly with personal anecdotes about early operational mistakes, including wasting $30k on an unappealing website redesign.7:13–9:54 · Harry as informed peer 3/10 Redefining Founder-First Venture Capital Harry pushes on potential boundary issues between acting as a supportive friend versus a firm investor. Brett reframes 'founder-first' as deep emotional connection rather than superficial niceness, arguing that genuine friendship builds the transparency needed for tough business conversations.9:55–14:43 · Harry as informed peer 4/10 LP Fiduciary Responsibility and Hard Founder Conversations Harry introduces strong pushback regarding LP fiduciary obligations when a founder's needs conflict with fund returns. Brett educates on a long-term venture thesis, explaining how treating failing founders honorably generates far greater long-term deal flow and LP returns than forcing short-term capital recovery.14:51–20:30 · Harry as informed peer 6/10 Autonomous Vehicles and the Future of Mobility Harry demonstrates strong domain familiarity by correcting Brett on GM acquiring Cruise and questioning whether ethical decision-making in self-driving cars constitutes Artificial Superintelligence. Brett presents speculative mobility concepts like specialized autonomous fleet interiors.20:31–26:28 · Harry as informed peer 3/10 Quick Fire Round with Brett DeMarrais Harry guides a brisk quick-fire round covering books, fitness lessons from CrossFit, VR, and recent portfolio company Gather. Brett playfully reacts when Harry admits to never reading or watching Lord of the Rings.2:11–4:19 · Guest teaching 1/10 Brett DeMarrais's Journey into Venture Capital Harry asks a standard conversational question about Brett's career entry and offers light, encouraging banter about his potential as an investor. Brett warmly details his transition from his startup Wedit to joining Ludlow Ventures alongside Jonathan Triest.4:19–7:13 · Guest teaching 2/10 Founder Struggles and Early Entrepreneurial Lessons Harry opens up about his own early business struggles to set up an empathetic prompt on founder resilience. Brett responds candidly with personal anecdotes about early operational mistakes, including wasting $30k on an unappealing website redesign.7:13–9:54 · Guest teaching 3/10 Redefining Founder-First Venture Capital Harry pushes on potential boundary issues between acting as a supportive friend versus a firm investor. Brett reframes 'founder-first' as deep emotional connection rather than superficial niceness, arguing that genuine friendship builds the transparency needed for tough business conversations.9:55–14:43 · Guest teaching 4/10 LP Fiduciary Responsibility and Hard Founder Conversations Harry introduces strong pushback regarding LP fiduciary obligations when a founder's needs conflict with fund returns. Brett educates on a long-term venture thesis, explaining how treating failing founders honorably generates far greater long-term deal flow and LP returns than forcing short-term capital recovery.14:51–20:30 · Guest teaching 3/10 Autonomous Vehicles and the Future of Mobility Harry demonstrates strong domain familiarity by correcting Brett on GM acquiring Cruise and questioning whether ethical decision-making in self-driving cars constitutes Artificial Superintelligence. Brett presents speculative mobility concepts like specialized autonomous fleet interiors.20:31–26:28 · Guest teaching 2/10 Quick Fire Round with Brett DeMarrais Harry guides a brisk quick-fire round covering books, fitness lessons from CrossFit, VR, and recent portfolio company Gather. Brett playfully reacts when Harry admits to never reading or watching Lord of the Rings.2:11–4:19 · Guest disagreement 0/10 Brett DeMarrais's Journey into Venture Capital Harry asks a standard conversational question about Brett's career entry and offers light, encouraging banter about his potential as an investor. Brett warmly details his transition from his startup Wedit to joining Ludlow Ventures alongside Jonathan Triest.4:19–7:13 · Guest disagreement 0/10 Founder Struggles and Early Entrepreneurial Lessons Harry opens up about his own early business struggles to set up an empathetic prompt on founder resilience. Brett responds candidly with personal anecdotes about early operational mistakes, including wasting $30k on an unappealing website redesign.7:13–9:54 · Guest disagreement 1/10 Redefining Founder-First Venture Capital Harry pushes on potential boundary issues between acting as a supportive friend versus a firm investor. Brett reframes 'founder-first' as deep emotional connection rather than superficial niceness, arguing that genuine friendship builds the transparency needed for tough business conversations.9:55–14:43 · Guest disagreement 1/10 LP Fiduciary Responsibility and Hard Founder Conversations Harry introduces strong pushback regarding LP fiduciary obligations when a founder's needs conflict with fund returns. Brett educates on a long-term venture thesis, explaining how treating failing founders honorably generates far greater long-term deal flow and LP returns than forcing short-term capital recovery.14:51–20:30 · Guest disagreement 2/10 Autonomous Vehicles and the Future of Mobility Harry demonstrates strong domain familiarity by correcting Brett on GM acquiring Cruise and questioning whether ethical decision-making in self-driving cars constitutes Artificial Superintelligence. Brett presents speculative mobility concepts like specialized autonomous fleet interiors.20:31–26:28 · Guest disagreement 1/10 Quick Fire Round with Brett DeMarrais Harry guides a brisk quick-fire round covering books, fitness lessons from CrossFit, VR, and recent portfolio company Gather. Brett playfully reacts when Harry admits to never reading or watching Lord of the Rings.2:11–4:19 · Harry pushing back 0/10 Brett DeMarrais's Journey into Venture Capital Harry asks a standard conversational question about Brett's career entry and offers light, encouraging banter about his potential as an investor. Brett warmly details his transition from his startup Wedit to joining Ludlow Ventures alongside Jonathan Triest.4:19–7:13 · Harry pushing back 0/10 Founder Struggles and Early Entrepreneurial Lessons Harry opens up about his own early business struggles to set up an empathetic prompt on founder resilience. Brett responds candidly with personal anecdotes about early operational mistakes, including wasting $30k on an unappealing website redesign.7:13–9:54 · Harry pushing back 2/10 Redefining Founder-First Venture Capital Harry pushes on potential boundary issues between acting as a supportive friend versus a firm investor. Brett reframes 'founder-first' as deep emotional connection rather than superficial niceness, arguing that genuine friendship builds the transparency needed for tough business conversations.9:55–14:43 · Harry pushing back 3/10 LP Fiduciary Responsibility and Hard Founder Conversations Harry introduces strong pushback regarding LP fiduciary obligations when a founder's needs conflict with fund returns. Brett educates on a long-term venture thesis, explaining how treating failing founders honorably generates far greater long-term deal flow and LP returns than forcing short-term capital recovery.14:51–20:30 · Harry pushing back 4/10 Autonomous Vehicles and the Future of Mobility Harry demonstrates strong domain familiarity by correcting Brett on GM acquiring Cruise and questioning whether ethical decision-making in self-driving cars constitutes Artificial Superintelligence. Brett presents speculative mobility concepts like specialized autonomous fleet interiors.20:31–26:28 · Harry pushing back 1/10 Quick Fire Round with Brett DeMarrais Harry guides a brisk quick-fire round covering books, fitness lessons from CrossFit, VR, and recent portfolio company Gather. Brett playfully reacts when Harry admits to never reading or watching Lord of the Rings.

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

0:00 · Harry 77.1% · guest 22.9%0:00 · Harry 77.1% · guest 22.9%3:00 · Harry 21.3% · guest 78.7%3:00 · Harry 21.3% · guest 78.7%6:00 · Harry 11.6% · guest 88.4%6:00 · Harry 11.6% · guest 88.4%9:00 · Harry 18% · guest 82%9:00 · Harry 18% · guest 82%12:00 · Harry 20.1% · guest 79.9%12:00 · Harry 20.1% · guest 79.9%15:00 · Harry 18.5% · guest 81.5%15:00 · Harry 18.5% · guest 81.5%18:00 · Harry 20% · guest 80%18:00 · Harry 20% · guest 80%21:00 · Harry 22.2% · guest 77.8%21:00 · Harry 22.2% · guest 77.8%24:00 · Harry 16.4% · guest 83.6%24:00 · Harry 16.4% · guest 83.6%27:00 · Harry 100% · guest 0%27:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 21:08 You're dead to me

Brett jokingly declares Harry 'dead to me' after Harry reveals he has never read or watched Lord of the Rings.

 Hardest push from Harry ▶ 11:07 Challenging LP fiduciary tension

Harry directly challenges Brett's ultra-founder-friendly stance by pressing him on how to balance that empathy with fiduciary duties to LPs.

 Biggest teaching moment ▶ 11:30 Reframing fiduciary duty around long-term reputation

Brett reframes the host's premise on fiduciary duty, explaining that preserving founder goodwill yields exponentially better long-term deal flow and LP returns than clawing back small short-term returns.

 Harry holds his own ▶ 16:46 Correcting GM's acquisition of Cruise

Harry instantly fills in the buyer details when Brett blanks on who acquired Cruise, correctly naming GM and commenting on their aggressive M&A approach.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Brett DeMarrais's Journey into Venture Capital 2100 Harry asks a standard conversational question about Brett's career entry and offers light, encouraging banter about his potential as an investor. Brett warmly details his transition from his startup Wedit to joining Ludlow Ventures alongside Jonathan Triest.
Founder Struggles and Early Entrepreneurial Lessons 3200 Harry opens up about his own early business struggles to set up an empathetic prompt on founder resilience. Brett responds candidly with personal anecdotes about early operational mistakes, including wasting $30k on an unappealing website redesign.
Redefining Founder-First Venture Capital 3312 Harry pushes on potential boundary issues between acting as a supportive friend versus a firm investor. Brett reframes 'founder-first' as deep emotional connection rather than superficial niceness, arguing that genuine friendship builds the transparency needed for tough business conversations.
LP Fiduciary Responsibility and Hard Founder Conversations 4413 Harry introduces strong pushback regarding LP fiduciary obligations when a founder's needs conflict with fund returns. Brett educates on a long-term venture thesis, explaining how treating failing founders honorably generates far greater long-term deal flow and LP returns than forcing short-term capital recovery.
Autonomous Vehicles and the Future of Mobility 6324 Harry demonstrates strong domain familiarity by correcting Brett on GM acquiring Cruise and questioning whether ethical decision-making in self-driving cars constitutes Artificial Superintelligence. Brett presents speculative mobility concepts like specialized autonomous fleet interiors.
Quick Fire Round with Brett DeMarrais 3211 Harry guides a brisk quick-fire round covering books, fitness lessons from CrossFit, VR, and recent portfolio company Gather. Brett playfully reacts when Harry admits to never reading or watching Lord of the Rings.

Statements from this episode (8)

Assertion Not checkable as stated
Ludlow Ventures Spent 6 to 9 Months Fundraising Before Taking Paychecks
“There was no vehicle to invest out of. And so I said yes on the spot. And then it was, you know, six to nine months of toiling away, raising money before, before we actually took paychecks.”
Brett DeMarrais Sep 7, 2016 ▶ 4:33
Assertion Not checkable as stated
DeMarrais Spent $30K of $75K Startup Capital on Website Design
“I took 30,000 dollars of about the 75,000 dollars I raised, and I hired someone to design a website for my company”
Brett DeMarrais Sep 7, 2016 ▶ 6:13
Insight
DeMarrais: Personal Friendships With Founders Drive Better Venture Outcomes
“I don't think that's a problem at all, because I think the closer you can come to developing an actual friendship, the better the business relationship will be, and so I think if you're the person who they want to go to the ballgame with or have a beer with or…”
Brett DeMarrais Sep 7, 2016 ▶ 9:05
Insight
DeMarrais: Venture capital is a customer service and human relationship business
“People starting businesses are people and they're not an asset class to be invested in. And so I think when more and more VCs understand that and treat venture capital as a customer service business, as a human relationship business, then we'll all be better o…”
Brett DeMarrais Sep 7, 2016 ▶ 10:52
Insight
Respecting Failing Founders Yields Better LP Returns Than Salvage Sales
“Treating that person well, handling it with respect, Making sure that they're comfortable is long-term a better outcome for both our LPs, us, and the founder than trying to sell the company and claw back our money.”
Brett DeMarrais Sep 7, 2016 ▶ 12:19
Prediction Not checkable as stated
DeMarrais: Autonomous Vehicle Fleets Will Make Car Ownership Obsolete
“I think car ownership is, is, is going to be a thing of the past because when autonomous vehicles come around, you know, there'll be these fleets of vehicles. You can just call on one button. I think it'll be cheaper. It'll be more convenient.”
Brett DeMarrais Sep 7, 2016 ▶ 15:10
Insight
DeMarrais: Startup Growth Parallels Fitness Gains, Requiring Exponential Effort Later
“The easiest gains are always at the beginning... The amount I could lift would increase rapidly up until a certain point. And then it was exponential effort to get, you know, a minuscule gain. And I think that's a lot like working at a startup.”
Brett DeMarrais Sep 7, 2016 ▶ 22:06
Opinion
DeMarrais: VR Will Transform Collaboration But Not Replace Traditional Media
“I think it's a game changer for collaboration and workforces. I think it's an extension of entertainment for people. I don't buy in that, you know, VR is going to be a replacement for movies or television or books.”
Brett DeMarrais Sep 7, 2016 ▶ 23:05
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