Feb 6, 2017 · 30m · 20vc
20VC: What Does It Take To Gain A Late Stage Cheque Today? The Fundamental Mistakes CEOs Make In The Scaling Process & The Importance Of Building The Next S Curve For Founders with Jules Maltz, General Partner @ IVP
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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 VC, host Harry Stebbings interviews Jules Maltz, General Partner at Insight Venture Partners, discussing the evolution of late-stage growth investing, essential startup scaling benchmarks, and the vital role of founder resiliency and board relationships.
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 2.1 Guest teaching 3.3 Guest disagreement 1.0 Harry pushing back 0.7
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 22:06 Rejecting Horse vs. Jockey Binary
Jules explicitly disagrees with the premise brought up by Harry from Rory O'Driscoll, arguing that setting founder vs market as opposing choices is an artificial debate.
Hardest push from Harry ▶ 21:41 Challenging Founder Primacy with Rory O'Driscoll QuoteHarry confronts Jules's founder-centric perspective by quoting Scale VP partner Rory O'Driscoll's thesis that market and product eclipse founders at the late stage.
Biggest teaching moment ▶ 7:00 Correcting the Concept of 'Hacking' TrustJules reframes Harry's suggestion of 'hacking' trust-building, emphasizing that trying to game or optimize relationship onboarding is transparently disingenuous.
Harry holds his own ▶ 21:41 Introducing Late-Stage Market Dynamics DebateHarry demonstrates industry knowledge by bringing up a prominent counter-thesis from a previous high-profile guest to test Jules's philosophy.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Jules Maltz's Journey into Venture Capital | 1 | 2 | 0 | 0 | Harry introduces Jules and asks broad standard questions regarding his career path and trends in late-stage VC. Jules outlines how late-stage investing shifted from a passive relationship-driven model to a proactive sourcing strategy. | |
| Building Authentic Relationships and Trust with Founders | 2 | 4 | 2 | 1 | Jules gently rejects Harry's framing regarding concerns about over-delivering value pre-investment as an 'irrational worry'. He further dismisses Harry's query on how to 'hack' trust-building, explaining that authentic relationship building cannot be shortcut. | |
| Key Metrics for Late-Stage Investments and IPOs | 2 | 4 | 0 | 0 | Harry asks about late-stage check criteria and IPO standards. Jules educates the audience on specific quantitative hurdles such as $100M+ revenue and clear path to profitability, while contrasting current discipline with flawed 2014-2015 unit economics. | |
| Scaling Challenges and Executive Leadership Mistakes | 2 | 3 | 1 | 1 | Harry probes on the extent to which board members should push CEOs to pivot or change. Jules explains that authoritarian table-pounding VCs fail, drawing a parallel to his parents' background in social work and counseling to highlight listening over commanding. | |
| Generational Dynamics, VC Humility, and the S-Curve | 2 | 3 | 0 | 0 | Harry asks about staying connected across changing founder generations. Jules humorously shares a story about a 24-year-old CEO telling him 'people of your generation won't understand this', before breaking down the concept of building sequential S-curves. | |
| Founder Resiliency vs. Market Dynamics | 5 | 5 | 4 | 3 | Harry uses informed pushback by citing Rory O'Driscoll's claim that market/product eclipse the founder at late stage. Jules directly disagrees with the premise, calling the horse vs. jockey debate unnecessary and citing case studies where founder resilience saved failing market thesis investments. | |
| Quick Fire Round with Jules Maltz | 1 | 2 | 0 | 0 | A friendly quick-fire round covering books, mentors, and habits. Jules provides practical advice for young venture capitalists to leverage their energy and relative advantages. |
Statements from this episode (15)
Maltz: Late-stage VC shifted from reactive relationships to proactive sourcing
“Venture historically has been very much a cottage or relationship industry, and so deal flow would often come to the later stage investors from great early stage firms, and early stage firm would fund a series A or series B, and then basically they'd Go to the…”
Maltz: IVP targets five to ten fastest-growing late-stage companies weekly
“Every week we're talking about what are the five or 10 fastest growing later stage companies that we're incredibly excited about. And then we're thinking about ways to connect directly with the CEO, actually add value to the company before we invest, and then …”
Maltz: IVP often makes late-stage investment decisions in days or hours
“We're often making decisions in a matter of days or even hours versus weeks or months, so it's one of those things where you know, you're waiting around a lot, and then you hurry up, and you have this kind of rush process, but the best companies are, that's ho…”
Maltz: Tech IPOs need $100M revenue, 30% growth, and profitability path
“Companies need to be generally over a hundred million dollars in revenue. They need to be growing over 30%, and they need to have, if not, if they're not profitable, they need to have a very clear path to profitability within two to four quarters.”
Maltz: Magic Leap raised billions of dollars without a launched product
“You're seeing companies like magic leap without a launch product raise, you know, billions of dollars.”
Maltz: The 2014-2015 unicorn boom funded startups with flawed unit economics
“I think in 2014 and 15, during kind of the unicorn boom that we were having, you were seeing things that were getting funded that had amazing revenue growth, but fundamentally flawed unit economics.”
Maltz: Top CEOs continuously upgrade management teams even during rapid growth
“The best CEOs, even when things are going incredibly well, are constantly making upgrades and changes to their management team.”
Maltz: Facebook successfully transitioned from desktop to mobile revenue post-IPO
“When the company went public on basically desktop revenues and, you know, the market massively changed to mobile and Facebook had done so much investing around mobile in their platform and in their technology and in their advertising that they made this incred…”
Maltz: Board members cannot dictate strategy to CEOs without losing trust
“Whenever you try to tell a CEO, Hey, you have to do this. The natural reaction is to get defensive and Hey, you don't know my business. You're coming in here once every two or three months. How do you know it better than I do? And the answer is we don't. So th…”
Maltz: Aging VCs lose touch with young founders and consumer trends
“I think there's two big challenges with kind of getting older in venture. The first is you just get Farther away from the age of the CEOs, at least in the consumer space and what the kind of teenagers are doing in terms of using the products.”
Maltz: VCs hear 200 pitches yearly but make only two investments
“In a year, maybe 200 companies will present to you and you'll only do one or two investments.”
Maltz: Top companies plan their next S-curve during peak growth
“The best businesses are actually thinking about, even when they're going through that fastest S curve, they're thinking about, what's the next S curve that I can build in the business?”
Maltz: Initial investment theses for Yext and TuneIn failed to pan out
“You know, I've actually had two companies I've invested in a company called Yaxt and a company called TuneIn where the original investment thesis ended up actually not panning out as well.”
Maltz: Junior VCs win by leveraging late nights and engineer networks
“Thinking about as a young person, thinking about what are your comparative advantages that those people can't do. So those people are all busy and you know, I'm busy too. And as a 24 year old you may be able to go out at night until 11 o'clock with a CEO and y…”