Todd Jackson
Partner, First Round Capital. On 3 shows, 12 appearances. The Shows tab opens the full record on each.
investorexecutivefounderhostoperator@tjack ↗LinkedIn ↗firstround.com ↗
Todd Jackson is a Partner at First Round Capital known for creating its framework on evaluating product-market fit. He previously co-founded Cover and served as VP of Product and Design at Dropbox, alongside product leadership roles at Google, Facebook, and Twitter.
3shows
12appearances
34statements
5resolved
4supported
0contradicted
80%fully supported
6said about them ↓ Everything Todd Jackson said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Jackson: Repositioning within existing categories is easier than category creation
“I think it's hard to create a category. Like it certainly works in some cases, but if you actually have like a really interesting spin on an existing category, like there's people are, there's already buyers spending money on that thing. They're already lookin…”
Jackson: The 'expensive' price in discovery is what customers will actually pay
“And like, generally when people tell you the fair price, it's a little bit of like, they're trying to get a deal. And the expensive price is the one, like if the price could, the expensive price is the one that they would actually pay. Right? That where they'r…”
Jackson: Sales-led B2B is more science than bottom-up or consumer products
“I think bottom up is its own kind of world. It's closer to consumer product development in my mind. And I have done, you know, consumer products, consumer product. I think there is a little bit more alchemy involved. It's about, you know, having great taste an…”
Jackson: Founders should sell before building to get customer signal
“I tend to gravitate towards the, like, I want to sell it before I build it because I really want the signal from customers. And I want that to sort of be the guide and the oxygen that drives what I'm building.”
Jackson: 60% to 70% of startups stall before achieving strong PMF
“The majority of companies, so greater than 50%, probably closer to 60 or 70% are gonna get stuck at L one or L two. And so that leaves, you know, roughly, let's say, 30%, make it to L three or L four, just in our experience looking broadly.”
Jackson: Founders rarely practice picking ideas, while VCs train it constantly
“As an engineer, as a founder, you, you've developed these muscles on how to build, and you are very good at building. But what you only do once or twice is pick the thing to work on. And VCs, you know, one of the, I think the luxuries that we have VCs, we get …”
Jackson: PMF is the single most important goal for startups in years 1-3
“Product market fit is the single most important thing that your startup does in the first three years.”
Jackson: WeWork and Casper failed on efficiency despite high customer satisfaction
“Like those products managed to achieve customer satisfaction and demand. But they never got the efficiency right. And so sort of the whole business just never worked right at scale.”
Jackson: As PMF strengthens, marginal customer acquisition should get progressively easier
“And if you have product market fit, and as you are progressing along this journey, the marginal customer should be getting easier and easier and easier to get, like easier to acquire them, easier to give them good service with a good product. And that's means …”
Jackson: Enterprise startups take four to six years to reach extreme PMF
“And for the best enterprise companies, I like, I would say they tend to reach extreme product market fit in like roughly four to six years, right? There's some variance but roughly four to six years.”
Jackson: Startups seeking nascent PMF must prioritize satisfaction over efficiency
“Of the three dimensions that you just recapped, Lenny, it's satisfaction first, demand second, efficiency last, when you're at level one. Like, it's actually okay to be inefficient at this stage, if it helps you uncover something that delivers an insanely good…”
Jackson: Early-stage startups should ignore burn multiple, gross margin, and NRR
“And then there are metrics to track efficiency, right? Things like burn multiple, gross margin, NRR, all of these things. They're all of them are just like not applicable at this stage. It's too early and you shouldn't be worrying about that stuff.”
Jackson: Early founders must avoid getting friend-zoned by polite customers
“Rick's analogy. I just love it for level one is you don't want to get friend zoned by your customers. Like you like where your customers like you, but they don't love you and they don't need you.”
Jackson: Cold sales conversion benchmark is around 10% at Level 2 PMF
“A benchmark we would say is that your sales conversion without a warm intro is still probably like 10%, something like that. Like first call to close one is like around 10%.”
Jackson: Slow sales cycles and low ACVs create a 'quadrant of death'
“You can't basically be in the worst of both worlds where you've got a slow sales cycle and a low ACV. Like that is the quadrant of death basically.”
Jackson: Companies reaching Level 3 PMF should see 10% to 20% organic inbound
“I think if you are starting to get to level three, which is where we're getting to next, you've probably got 10%, 20% of your inbound coming or completely organically, organic inbound.”
Jackson: Strong PMF requires >60% gross margin, <10% churn, and >110% NRR
“So like, you know, we're talking about our gross margin needs to be above 60%, hopefully above 70%. Our burn multiple is now below three, right? Like ideally we're in like the, ideally we're like close to one, right? Burn multiple, like in the one to three zon…”
Jackson: Extreme PMF on a core product does not make expansion PMF free
“Just because you got to level four on your main product doesn't mean product market fit is free on all these new products. Right. And you've been inside Airbnb and I've been inside, you know, Dropbox and Twitter, like getting new products to be successful is h…”
Jackson: Founders spend 99% building and only 1% choosing markets
“Founders spend 99% of their time building because that's what they've done, right? And they spend, like, one percent of their time picking and picking the market, picking the problem, picking the customer. And in reality, it's that pick that, like, determines …”
Jackson: Growing from 5 to 25 customers in a year indicates PMF
“If I see a company go from five customers to 25 in a year, that, that is almost always a strong, that there's like a sign that there's some pretty strong product market fit there.”
Jackson: Finding PMF after 4-5 years of stagnation is rare
“I do think if you've been going at it for four to five years and you haven't started to find anything that you're really feeling pull from the market on, I don't know. You've done it for four to five years. It's like, what are the chances that you're going to …”
Jackson: Founders should view markets as people, not abstract categories
“I think it's like much more tangible for a founder to think of the market as like a collection of people. Right? Like Jack Altman was thinking about his market as all of the HR leaders out there. And he was thinking about how many of them are there and what ar…”
Jackson: A prospect calling an idea 'interesting' means 'no'
“If you had reacted like, yeah, that sounds kind of interesting. That's a no, right? That is a no. That is a polite way of saying the word interesting is a polite way of saying no.”
Jackson: Best early customers have already failed to build internal solutions
“If a customer has a problem and like, I really think they have a problem and they know they have the problem and they're looking for a solution for the problem, or they've even tried to build their own solution to it and failed. That's like the best customer, …”
The other half of the tape: Todd Jackson's own voice is left out of every number here. Other people bring the name up 4 times in 3 episodes across the shows. 2 statements on the record name them. every mention, with the transcript →
Who brings them up most Jag Duggal 2Lenny Rachitsky 1Josh Koppelman 1
Statements about Todd Jackson, by other people (2)
Duggal: Companies must reinvent categories to dominate, not just improve incrementally
“At the company level, I think it's absolutely imperative. To be designing your own category so you can then dominate it and defining your own category. And even when you're entering a place where customers are spending money, I think going in with a mindset th…”
Every mention by year
tap a year for its mentions
Lenny's Podcast 3
In Depth 1
2026 1 mention in 1 episode
2024 2 mentions in 1 episode
2023 1 mention in 1 episode
One line per show, most statements first. The link opens Todd's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| LENNY'S PODCASTLEDGER | Partner, First Round Capital | 1 | 27 | 100% 2/2 | full record on Lenny's Podcast → |
 20VCLEDGER | Partner, First Round Capital | 1 | 5 | 50% 1/2 | full record on 20VC → |
| IN DEPTHLEDGER | Partner, First Round Capital | 10 | 2 | 100% 1/1 | full record on In Depth → |