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May 31, 2017 · 25m · 20vc

20VC: How Both Founders & GPs Should Construct Their Pitch, Why VCs Are Eternal Optimists & What Makes The Best Post-Investment VC/Founder Relationship with Brian Ascher, Partner @ Venrock

Brian Ascher · 17m spoken Harry Stebbings · 7m spoken
0:00 / 0:00

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In this episode of The 20 Minute VC, host Harry Stebbings interviews Venrock partner Brian Ascher to explore successful venture capital career paths, pitch deck construction, and post-investment founder-board dynamics. Ascher shares actionable insights on problem-first fundraising narratives, bottom-up market sizing, and building high-trust partnerships between investors and entrepreneurs.

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 31% of the talking time here. How this is scored →

Harry as informed peer 1.8 Guest teaching 5.0 Guest disagreement 0.4 Harry pushing back 0.0
05100:0010:0020:002:22–4:50 · Harry as informed peer 2/10 Brian Ascher's Career Path and Entry into VC Harry introduces Brian and asks standard questions about his entry into venture capital via the Kauffman Fellows Program. Brian explains his path and details two primary routes into VC, while Harry briefly adds a third path about starting a podcast.4:52–8:01 · Harry as informed peer 1/10 Pitch Construction, Storytelling, and Non-Obvious Insights Brian delivers a masterclass on pitch structure, arguing against the 'no slides' trend and explaining why starting with a team slide or origin story is ineffective. Harry acts purely as an agreeable listener guiding the conversation.8:02–13:38 · Harry as informed peer 3/10 Elements of a Pitch: Demos, Market Sizing, Risks, and Capital Raised Harry offers a personal critique of unrealistic top-down market sizing estimates. Brian expands on this by explaining how founders should frame non-obvious market insights rather than becoming defensive when challenged by investors.13:39–19:30 · Harry as informed peer 2/10 Case Study: Castlight Health's Problem-First Pitch Brian uses Castlight Health as a case study for problem-first pitching and discusses building trust in post-investment relationships. Harry asks thoughtful follow-ups about stress-testing board dynamics pre-investment.19:31–23:40 · Harry as informed peer 1/10 Quickfire Round: Books, Tools, Products, and Sokrati Investment During a quickfire round, Brian shares recommendations on leadership books, productivity software, and AI applications like Google Photos. The dynamic is fully collaborative and conversational.2:22–4:50 · Guest teaching 4/10 Brian Ascher's Career Path and Entry into VC Harry introduces Brian and asks standard questions about his entry into venture capital via the Kauffman Fellows Program. Brian explains his path and details two primary routes into VC, while Harry briefly adds a third path about starting a podcast.4:52–8:01 · Guest teaching 6/10 Pitch Construction, Storytelling, and Non-Obvious Insights Brian delivers a masterclass on pitch structure, arguing against the 'no slides' trend and explaining why starting with a team slide or origin story is ineffective. Harry acts purely as an agreeable listener guiding the conversation.8:02–13:38 · Guest teaching 6/10 Elements of a Pitch: Demos, Market Sizing, Risks, and Capital Raised Harry offers a personal critique of unrealistic top-down market sizing estimates. Brian expands on this by explaining how founders should frame non-obvious market insights rather than becoming defensive when challenged by investors.13:39–19:30 · Guest teaching 5/10 Case Study: Castlight Health's Problem-First Pitch Brian uses Castlight Health as a case study for problem-first pitching and discusses building trust in post-investment relationships. Harry asks thoughtful follow-ups about stress-testing board dynamics pre-investment.19:31–23:40 · Guest teaching 4/10 Quickfire Round: Books, Tools, Products, and Sokrati Investment During a quickfire round, Brian shares recommendations on leadership books, productivity software, and AI applications like Google Photos. The dynamic is fully collaborative and conversational.2:22–4:50 · Guest disagreement 0/10 Brian Ascher's Career Path and Entry into VC Harry introduces Brian and asks standard questions about his entry into venture capital via the Kauffman Fellows Program. Brian explains his path and details two primary routes into VC, while Harry briefly adds a third path about starting a podcast.4:52–8:01 · Guest disagreement 1/10 Pitch Construction, Storytelling, and Non-Obvious Insights Brian delivers a masterclass on pitch structure, arguing against the 'no slides' trend and explaining why starting with a team slide or origin story is ineffective. Harry acts purely as an agreeable listener guiding the conversation.8:02–13:38 · Guest disagreement 1/10 Elements of a Pitch: Demos, Market Sizing, Risks, and Capital Raised Harry offers a personal critique of unrealistic top-down market sizing estimates. Brian expands on this by explaining how founders should frame non-obvious market insights rather than becoming defensive when challenged by investors.13:39–19:30 · Guest disagreement 0/10 Case Study: Castlight Health's Problem-First Pitch Brian uses Castlight Health as a case study for problem-first pitching and discusses building trust in post-investment relationships. Harry asks thoughtful follow-ups about stress-testing board dynamics pre-investment.19:31–23:40 · Guest disagreement 0/10 Quickfire Round: Books, Tools, Products, and Sokrati Investment During a quickfire round, Brian shares recommendations on leadership books, productivity software, and AI applications like Google Photos. The dynamic is fully collaborative and conversational.2:22–4:50 · Harry pushing back 0/10 Brian Ascher's Career Path and Entry into VC Harry introduces Brian and asks standard questions about his entry into venture capital via the Kauffman Fellows Program. Brian explains his path and details two primary routes into VC, while Harry briefly adds a third path about starting a podcast.4:52–8:01 · Harry pushing back 0/10 Pitch Construction, Storytelling, and Non-Obvious Insights Brian delivers a masterclass on pitch structure, arguing against the 'no slides' trend and explaining why starting with a team slide or origin story is ineffective. Harry acts purely as an agreeable listener guiding the conversation.8:02–13:38 · Harry pushing back 0/10 Elements of a Pitch: Demos, Market Sizing, Risks, and Capital Raised Harry offers a personal critique of unrealistic top-down market sizing estimates. Brian expands on this by explaining how founders should frame non-obvious market insights rather than becoming defensive when challenged by investors.13:39–19:30 · Harry pushing back 0/10 Case Study: Castlight Health's Problem-First Pitch Brian uses Castlight Health as a case study for problem-first pitching and discusses building trust in post-investment relationships. Harry asks thoughtful follow-ups about stress-testing board dynamics pre-investment.19:31–23:40 · Harry pushing back 0/10 Quickfire Round: Books, Tools, Products, and Sokrati Investment During a quickfire round, Brian shares recommendations on leadership books, productivity software, and AI applications like Google Photos. The dynamic is fully collaborative and conversational.

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

0:00 · Harry 88.7% · guest 11.3%0:00 · Harry 88.7% · guest 11.3%3:00 · Harry 21% · guest 79%3:00 · Harry 21% · guest 79%6:00 · Harry 6.9% · guest 93.1%6:00 · Harry 6.9% · guest 93.1%9:00 · Harry 17.9% · guest 82.1%9:00 · Harry 17.9% · guest 82.1%12:00 · Harry 18.1% · guest 81.9%12:00 · Harry 18.1% · guest 81.9%15:00 · Harry 20.2% · guest 79.8%15:00 · Harry 20.2% · guest 79.8%18:00 · Harry 22.5% · guest 77.5%18:00 · Harry 22.5% · guest 77.5%21:00 · Harry 21.9% · guest 78.1%21:00 · Harry 21.9% · guest 78.1%24:00 · Harry 100% · guest 0%24:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 5:25 Rejecting the 'no slides' pitch trend

Brian forcefully counters the popular industry meme advocating for slide-less pitch conversations, arguing that structured decks craft essential narratives like Oscar-worthy films rather than unscripted improv.

 Hardest push from Harry ▶ 8:56 Challenging absurd top-down market sizing

Harry expresses explicit irritation with founders presenting ridiculous top-down market figures, citing examples of nightclub software decks claiming trillion-dollar TAMs.

 Biggest teaching moment ▶ 10:00 Reframing investor skepticism as a pitch asset

Brian educates founders on how to handle pushback, explaining that defensiveness during investor questioning ruins pitches when founders should instead reframe skepticism as proof of a non-consensus opportunity.

 Harry holds his own ▶ 8:56 Critiquing unrealistic market size slides

Harry draws on his experience interviewing founders to critique flawed market-sizing logic, demonstrating host expertise with specific real-world examples.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Brian Ascher's Career Path and Entry into VC 2400 Harry introduces Brian and asks standard questions about his entry into venture capital via the Kauffman Fellows Program. Brian explains his path and details two primary routes into VC, while Harry briefly adds a third path about starting a podcast.
Pitch Construction, Storytelling, and Non-Obvious Insights 1610 Brian delivers a masterclass on pitch structure, arguing against the 'no slides' trend and explaining why starting with a team slide or origin story is ineffective. Harry acts purely as an agreeable listener guiding the conversation.
Elements of a Pitch: Demos, Market Sizing, Risks, and Capital Raised 3610 Harry offers a personal critique of unrealistic top-down market sizing estimates. Brian expands on this by explaining how founders should frame non-obvious market insights rather than becoming defensive when challenged by investors.
Case Study: Castlight Health's Problem-First Pitch 2500 Brian uses Castlight Health as a case study for problem-first pitching and discusses building trust in post-investment relationships. Harry asks thoughtful follow-ups about stress-testing board dynamics pre-investment.
Quickfire Round: Books, Tools, Products, and Sokrati Investment 1400 During a quickfire round, Brian shares recommendations on leadership books, productivity software, and AI applications like Google Photos. The dynamic is fully collaborative and conversational.

Statements from this episode (8)

Insight
Ascher: Breaking into VC requires starting young or an executive track record
“Well, there's kind of two paths. You beat and kick and scratch and claw your way in as a young person who doesn't yet really have much to bring to the table by way of a track record or proven deal flow based on your stature as a founder or senior executive at …”
Brian Ascher May 31, 2017 ▶ 3:49
Insight
Ascher: Pitch decks have replaced business plans as the de facto standard
“So my first advice is to have slides. They're not only useful for fundraising, but the PowerPoint deck has become the de facto business plan. It can substitute for your mission statement, vision statement, etc. Like, there's never not a good time to have a goo…”
Brian Ascher May 31, 2017 ▶ 6:16
Insight
Ascher: Move team slides to the middle or end of pitch decks
“But generally a team slide, it's hard to generate excitement and interest. Like you might all have very impressive backgrounds, but a five minute slog of three or four or 10 people's resumes, it's just not high energy. And it's much better to do it at the midd…”
Brian Ascher May 31, 2017 ▶ 7:11
Insight
Ascher: Early-stage VCs seek non-consensus viewpoints that prove right
“We're looking for a non-consensus viewpoint that will ultimately prove right, and the market will catch up and reward the company for achieving this goal.”
Brian Ascher May 31, 2017 ▶ 11:23
Assertion Partly supported
Ascher: Jack Dorsey's Square Series A pitch listed 75 company risks
“I remember seeing Jack Dorsey's pitch for squares series a, and he literally started with like, these are 75 things that could kill this company in the short term.”
Brian Ascher May 31, 2017 ▶ 12:24
Insight
Ascher: Board meetings should focus on problem-solving, not celebrating success
“I assume going into every one of our companies that we're going to spend most of our time in board meetings and outside of board meetings, solving problems, fixing things, trying to make it better. We actually spend very little time congratulating ourselves on…”
Brian Ascher May 31, 2017 ▶ 16:08
Opinion
Ascher: Venture capital has become overly transactional and cap-table focused
“I'd like to see it be less transactional and more relationship oriented. I feel like it's become a bit of a, yeah, yeah, yeah, write me a check and join this long cap table list, but ultimately for me, again, it's about the long-term partnership relationship.”
Brian Ascher May 31, 2017 ▶ 20:51
Opinion
Ascher: Google Photos is an underrated example of artificial intelligence
“Google Photos, to me, is not getting nearly the credit and discussion it deserves For being a truly remarkable example of artificial intelligence.”
Brian Ascher May 31, 2017 ▶ 21:08
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