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Jason Lemkin

Jason Lemkin

Entrepreneur

Search complete. 111 mentions across 38 episodes found for "Jason Lemkin".

Nov 4, 2026

Jack SelbyGUEST
49:41
What I often have to be much more on the lookout for is the grandiosity piece.
David WeisburdHOST
49:45
Reminds me of a Jason Lemkin tweet, which I think it was during COVID where he said, in San Francisco, I'm unhappy, but productive.
David WeisburdHOST
49:52
Outside of San Francisco, I'm happier, but less productive.
David WeisburdHOST
49:55
Therefore, I will stay in San Francisco.
Harry StebbingsHOST
0:26
It's Rory O'Driscoll.
Harry StebbingsHOST
0:28
It's Jason Lemkin coming together to discuss the biggest news in tech.
Harry StebbingsHOST
0:32
Today, we have OpenAI's big fundraise, $1.25 trillion price down from $1.4.
Harry StebbingsHOST
0:38
Apparently, only $11 billion committed.
Rory O'DriscollPANELIST
5:23
It is as simple as that.
Rory O'DriscollPANELIST
5:24
No projection about AI, positively or negatively, just as two securities are going to be sold in the next two months.
Rory O'DriscollPANELIST
5:31
And which one do you want to buy? But Jason told me last week that it was the most
Jason LemkinPANELIST
5:34
underappreciated.
Dale ZwizinskiHOST
32:12
As we start wrapping some of this stuff up, we'd like to go into some uncentered questions with you, a little bit of rapid fire, see how you handle a little bit of the heat in the hot seat.
Dale ZwizinskiHOST
32:20
So Jason Lemkin has written that customer success took the biggest front of the SaaS layoff.
Dale ZwizinskiHOST
32:26
Worse than sales, worse than marketing, and CS got weaponized by sales into chasing renewals.
Dale ZwizinskiHOST
32:34
If CS is really the growth engine, why is it always the first head to be chopped off the block? Ooh, I love this one.
Dan MartellHOST
0:23
You know if you did that you'd actually be able to accelerate the sales process.
Dan MartellHOST
0:26
What I want to share with you and I've learned from a lot of incredible folks like Jason Lemkin at Sastr and the folks at HubSpot and many others in the SaaS pricing world, Why in the early days specifically it might make sense to not show your pricing so that you have more flexibility, more opportunities to learn and then finally design your packages to something that's repeatable, scalable once that's figured out.
Dan MartellHOST
0:48
Now I learned this by accident when I was building my company Spheric Technologies.
Dan MartellHOST
0:52
I was 24 when I started.
Mark RobergeGUEST
4:11
And one of the, one of the venues I love to, kind of bring some of those big annual insights to is Sastr.
Mark RobergeGUEST
4:20
My friend Jason Lemkin puts that thing on.
Mark RobergeGUEST
4:22
He asked me pretty like every other year to go and keynote it.
Mark RobergeGUEST
4:26
And I've always done different things from like the best plastic practices of product led growth to like common pitfalls in SaaS.
Dan MartellHOST
1:36
where he says that he's fired people for not managers, for not doing their one-on-ones.
Dan MartellHOST
1:41
And even Jason Lemkin from Saster Fame talks about it, where he says that one-on-ones are the most powerful tool a founder has to really align with their executive leadership team.
Dan MartellHOST
1:52
So these are all things that I've experienced.
Dan MartellHOST
1:54
I mean, just a few examples.
West BarnwellNARRATOR
0:45
Tech giants are issuing massive corporate bonds to fund this hardware cycle.
West BarnwellNARRATOR
0:49
Jason Lemkin told the 20VC podcast that traditional financial sectors are flashing red.
West BarnwellNARRATOR
0:55
Risk limits have been breached.
West BarnwellNARRATOR
0:57
Broadcom essentially had to bail out a debt issue just so Anthropic could purchase its chips.
David TischGUEST
15:18
Whereas I think in the past, you would probably put like a negative 80% on that number.
Harry StebbingsHOST
15:23
Well, Jason Lemkin, who I do a lot of shows with every week, we do the weekly show and he's like 100 60 you'll be diluted is that not true in your i don't think the best companies
David TischGUEST
15:35
now like not every company goes up and to the right and never sort of runs into bumps i think the macro when you get big can cause some bumps in valuation you're seeing it right now in some of the biggest labs going out and trying to raise rounds and sort of re re-evaluating the price that they're raising at if you go back in history Uber, Facebook, Airbnb, Ramp, which I think is one of the best modern companies ever, they've all had a bump, a down round.
David TischGUEST
16:02
And so I don't think it's always just up and to the right, but I think in this specific sort of three-year window, there is a lot of continued momentum in terms of valuations.
Greg HeadHOST
37:12
today's world.
Greg HeadHOST
37:13
But looking back, you know, Jason Lemkin, the SASTR guy, the big SASTR conference in Silicon Valley, big following, he asked founders, okay, VC-funded founders, now that starting your next company, you're doing it again, would you raise more money? Would you raise the same money? Would you raise less? Would you raise none? 70% of VC funded former founders said I would raise none, 45%, almost half.
Greg HeadHOST
37:43
And then, you know, the other 30 something percent said, you know, I'd raise a lot less.
Greg HeadHOST
37:48
So it's pretty common, right? You know, we get moving and then you kind of get this thing rolling and you kind of have to keep raising to keep the engine going.
Harry StebbingsHOST
0:26
This is 20VC with me, Harry Stebbings.
Harry StebbingsHOST
0:28
This is my favorite show of the week, Jason Lemkin, Rory O'Driscoll, the news that matters.
Harry StebbingsHOST
0:32
And let's be clear.
Harry StebbingsHOST
0:34
There is one story that matters more than any other this week.

5 MINS LATER

Jason LemkinPANELIST
6:02
And why would I waste my time with anything that's 10 to 12 years to IPO? But, you know, it's just one deal in the fund, another two years to distribute, you know, versus five
Rory O'DriscollPANELIST
6:13
years.
Rory O'DriscollPANELIST
6:14
No, I won't ask you, Jason.
Rory O'DriscollPANELIST
6:16
I mean, I think that, you know, I saw a tweet that basically said the same thing.

28 more episodes mention Jason Lemkin.

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