Josh Stein
Co-Founder and Managing Partner, Threshold Ventures. On 2 shows, 2 appearances. The Shows tab opens the full record on each.
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.
2shows
2appearances
15statements
2resolved
2supported
0contradicted
100%fully supported
9said about them ↓ Everything Josh Stein said on any show that made the record, most notable first. Each card names its show and opens the statement there.
DFJ replaces portfolio CEOs primarily for failing to learn from mistakes
“The number one reason where we do occasionally say, Hey, this is not the right leader for the company is when you see someone who's not able to learn from their mistakes, right. And adapt to them.”
Salesforce could double its prices without losing many customers
“Salesforce could double their prices. I don't think they would lose many customers.”
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.”
SaaS startups now reach $1M ARR on just $1M to $2M capital
“A typical, back in my day, to get to a million dollars of ARR, you might have spent 10 or twenty million dollars. Now, companies are getting there on a million or two million dollars more typically.”
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.”
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.”
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…”
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 …”
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.”
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.”
Founders must be forceful and willing to annoy people to succeed
“Hey, if you're not annoying people, you're not doing enough as an entrepreneur. I mean, you know, it's not a place for shrinking violence. Like you need to be forceful to get ahead.”
Box's post-2008 revenue ramped from $5M to $125M
“They went rough revenue ramp was five, 10, 25, 55, one, 25, and so just, you know, exploding out of the gate on the heels of that.”
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”
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…”
The other half of the tape: Josh Stein's own voice is left out of every number here. Other people bring the name up 9 times in 5 episodes across the shows. every mention, with the transcript →
Who brings them up most Jason Lemkin 4Harry Stebbings 3Rory O'Driscoll 1Edith Harbaugh 1
Every mention by year
tap a year for its mentions
20VC 8
the Official SaaStr Podcast 1
2023 5 mentions in 3 episodes 2 per episode
- DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
- Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
- Scaling to $100M ARR: The Top 10 Mistakes to Avoid From LaunchDarkly Co-Founder Edith Harbaugh
- every mention in 2023, scene by scene →
2017 3 mentions in 1 episode
One line per show, most statements first. The link opens Josh's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| SAASTRLEDGER | Co-Founder and Managing Partner, Threshold Ventures | 1 | 10 | — | full record on the Official SaaStr Podcast → |
| 20VCLEDGER | Co-Founder and Managing Partner, Threshold Ventures | 1 | 5 | 100% 2/2 | full record on 20VC → |