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Josh Stein

Co-Founder and Managing Partner, Threshold Ventures · 1 appearance on the record.

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investorfounderexecutive@dfjjosh ↗LinkedIn ↗threshold.vc ↗Wikipedia ↗

Josh Stein is a venture capitalist best known for leading early-stage investments in enterprise software companies including Box, Twilio, and Doximity. He spent over a decade as a Managing Director at DFJ before co-founding Threshold Ventures in 2019.

10statements → 1claims → 0claims resolved → 3.6/5average certainty → 1.8/5average debate potential → 1said about them ↓

1 not checkable as stated how the 1 claim stands · each chip opens the sources

1 assertion · 7 insights · 2 disclosures · every statement was checked. The predictions and assertion are the 1 claim: statements the public record can support or contradict. 0 are resolved, and 1 names no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Josh argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

How they sound: not measured why? →

We measure speaking style by listening to the audio itself, and a fair number needs at least 2,000 words from one person on tape we have measured. There is too little of Josh Stein on measured tape to publish a rate. This says nothing about how they speak.

Everything Josh Stein said on the Official SaaStr Podcast that made the record, most notable first. Filter by type, assessment or year in the ledger →

Insight
Founders cannot be taught how to communicate a transcendent vision
“And I think that's, you know, that's not, that's the part I don't think you can necessarily teach. I actually think the other stuff can be learned.”
Josh Stein Jul 7, 2017 ▶ 10:07 Josh Stein of DFJ: What Makes a Great SaaS CEO
Insight
Founders fail as scale-stage CEOs when they refuse to change
“I think the people who often fail, not always, but often fail to make the transition to being a bigger company CEO past that kind of initial founder stage, Is they don't want to change.”
Josh Stein Jul 7, 2017 ▶ 13:06 Josh Stein of DFJ: What Makes a Great SaaS CEO
Disclosure
Twilio CEO Jeff Lawson rejected opaque enterprise pricing for 'no shenanigans'
“And we've had talks, like, hey, are we leaving money on the table? Like, you know, And he's like, nope, no shenanigans. Boom. That makes it a very short conversation.”
Josh Stein Jul 7, 2017 ▶ 15:40 Josh Stein of DFJ: What Makes a Great SaaS CEO
Insight
Startups hit severe organizational breakpoints at 50 and 200 employees
“We think, I always tell people, we see three distinct breakpoints for CEOs. The first is around 40 or 50 people and that's usually where communications break down. You can't just rely on osmosis to get information out in the company anymore. You gotta actually…”
Josh Stein Jul 7, 2017 ▶ 16:08 Josh Stein of DFJ: What Makes a Great SaaS CEO
Insight
CEOs of 1,000-person companies should have at most ten direct reports
“And then a thousand is really interesting, because at a thousand, like if you're interacting From a reporting relationship with more than, I'd say, six to 10 people, you're really probably doing something wrong. Spending most of your time externally, and then …”
Josh Stein Jul 7, 2017 ▶ 16:46 Josh Stein of DFJ: What Makes a Great SaaS CEO
Insight
A 'two in a box' shared executive leadership model consistently fails
“What does not work is two in a box where people feel like they have to ask you and this other person to decide and, you know, if you can't find both or they disagree what happens and everyone gets really confused.”
Josh Stein Jul 7, 2017 ▶ 18:27 Josh Stein of DFJ: What Makes a Great SaaS CEO
Insight
Hiring a COO at $1M ARR is far too early
“And I'd say a million in ARRs too early. I think, you know, 40, 50 people is probably where it might become relevant.”
Josh Stein Jul 7, 2017 ▶ 19:10 Josh Stein of DFJ: What Makes a Great SaaS CEO
Assertion Not checkable as stated
Stein: Box's business customers churned least and consumed fewest resources
“The best customers, the ones that were paying us the most, that churned the least, ah, that actually were, interestingly, consuming the least resources. From a cost of goods standpoint, were the businesses”
Josh Stein Jul 7, 2017 ▶ 11:28 Josh Stein of DFJ: What Makes a Great SaaS CEO
Insight
Scaling to $10M ARR requires simultaneously building the foundation for $20M
“One thing companies always forget is, let's say you're going from five to ten million in revenue, it's not just going from five to 10, it's going from five to 10, and in that year, you're laying the groundwork to go from 10 to 20. And if you're not, you're goi…”
Josh Stein Jul 7, 2017 ▶ 21:14 Josh Stein of DFJ: What Makes a Great SaaS CEO
Disclosure
DFJ became Box's first institutional investor after a TechCrunch party
“Yeah, yeah, first institutional investor. We met him at Mike Earrington's house, actually.”
Josh Stein Jul 7, 2017 ▶ 5:52 Josh Stein of DFJ: What Makes a Great SaaS CEO

The other half of the tape: Josh Stein's own voice is left out of every number here. Other people bring the name up 1 time in 1 episode on the Official SaaStr Podcast. every mention, with the transcript →

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Appearances (1)

EpisodeDateSpeaking time
Josh Stein of DFJ: What Makes a Great SaaS CEO Jul 7, 2017 11m
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