Jordan Gal
Co-founder & CEO, Rosie. On 1 show, 7 appearances. The Shows tab opens the full record on each.
founderexecutivehostoperator@jordangal ↗LinkedIn ↗heyrosie.com ↗
Jordan Gal is a software entrepreneur who founded CartHook, co-founded Rally, and currently leads Rosie, an AI voice answering service. He also co-hosts the Bootstrapped Web podcast alongside Brian Casel.
1shows
7appearances
52statements
4resolved
1supported
1contradicted
25%fully supported
29said about them ↓ Everything Jordan Gal said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Gall: Building vertical niche SaaS in AI voice is currently the wrong move
“Normally in SaaS, what would you and I recommend to ourselves and to other people? Don't try to be broad for everybody. Find a niche. The niches are big enough. Kill it for one type of customer, then expand. In this, I think it's the exact opposite. So I see a…”
Gall: Subpar AI categories are the best areas to build in early
“Because I think everything in AI will be very good. And so the things that aren't that good right now are actually the best things to build in because everyone just assumes, oh, who's, is it a voice? Is it really going to replace a person? Yes, actually it is.…”
Gall: Crypto lacks real demand outside gambling
“Because crypto feels like a huge innovation, not much demand outside of, you know, gambling.”
Gall: Exposing full AI power to users creates onboarding friction
“Voice and AI is really, really powerful, and when something's really powerful, you're tempted to bring all that power to the user, and that's what creates onboarding friction.”
Gal: CartHook processed $2 billion in volume without being PCI compliant
“At Cardhook, we built a business that processed two billion dollars, and we were never PCI compliant, because we didn't need to be.”
Gall: Debt financing works best alongside equity raises to extend runway
“It is really tailored for being put alongside an equity raise. That's where it really makes a lot of sense. If you're at three million in ARR and you want to get to five before you fundraise, you can pull a million bucks and you're kind of going for broke anyw…”
Jordan Gall: Software buying in the UK requires personal pub relationships
“The buying process in the UK is not like in the US. That is an understatement. You basically need An inn. A personal inn that, like, requires a Guinness at a pub. And that's how everything is bought there”
Jordan Gall advises early-stage startups against selling into the UK
“Convince them to stop selling into the UK is, that would be my advice, which is, is really tough.”
Gall: Shopify ended CartHook's run by blocking off-platform payment processing
“And then it ran into a wall named Shopify. So they did not want checkouts to take Payment processing off of their platform, and they ended Carthook's run.”
Gall: AI voice agents provide ROI simply by beating voicemail
“Because it's not replacing a human. It replaces voicemail. So it just has to beat voicemail, and you get ROI.”
Gall: MVPs are easier in AI than SaaS because founders build less
“And the reason MVPs in AI and SaaS are like very, very different things is because in AI, you don't build nearly as much as you do in SaaS. So if you want to build a CRM, you kind of can't launch an MVP. You know, if you want an email, for example, Look, you c…”
Gall: DeepSeek commoditizes LLMs and shifts value to the application layer
“I think the conversation changed for the healthier with Deep Seek, because it poked a hole in the potential value right, the flip side of this, the commoditization of the LLMs, and so it put a lot more focus and attention on the application layer, and it, I th…”
Gal: B2B companies broadly struggle to make paid marketing work
“People are having a lot of difficulty making paid marketing work for B to B, and obviously everything I'm seeing is with a caveat. Hopefully there are people out there that are doing fantastically well with it, but it is a genuine problem. No one really knows …”
Gal: Leadpages is an asset that will only decrease in value
“This is an asset that will only decrease in value moving forward.”
Gal: Pipe charges 15% for non-debt SaaS revenue factoring
“Pipe.com is not debt. And it's kind of like factoring, but for SAS and they charge you 15%, which is basically what you would charge people anyway, because you would give them two months free.”
Gall: New AI tooling compressed Rosie's year-long product roadmap to three months
“What we thought would take us a year to build out all these channels with this new tooling, we're understanding, okay, we can probably build all these out in like three months.”
Gall: Rosie hides LLMs, models, and prompts completely from users
“In our product, the concept of an LLM or a model or a prompt does not exist. There is no choose your model, like absolutely not. It's just the problem and here's the solution for it.”
Gall: A $500–$1,000 lawyer threat letter is worth sending to copycats
“Now, I do want to just inject into this that a very strongly worded letter from a lawyer can be very effective. It depends on the person. It depends on the situation and what the resources are of the other company, that sort of thing. But a very scary letter f…”
Gall: True product-market fit feels effortless because customers demand the product
“It's not hard at all. Everyone just wants it, and they're pulling at you, and demanding, and asking, and begging, and want it to work.”
Gall: Rosie does not develop transcription, voice, or LLMs in-house
“So, we don't do the transcribing, we don't do the voice, we don't do the LLM. In some ways, like, what are we actually doing? It's just that the UI layer that allows a three-person painting company to have an AI phone receptionist up and running in 10 minutes.…”
Gall: Software founders have far more flexibility to raise prices and cut features
“In software, we have a lot more flexibility than we think we do, whether it's raising prices, taking features away, or just coming up with other solutions.”
Gall: Rosie switched from 7-day to 25-minute usage trials to cut churn
“So what we did is we switched from a seven-day trial to a twenty-five-minute trial, and what that did is it went from time to usage-based. So now everyone that converts is an activated user that's already converted their behavior. Which is partly why our churn…”
Gall: AI founders must combine extreme optimism with constant paranoia
“Extreme optimism and paranoia. I think that, that is the appropriate stance for the CEO of this company, is we are gonna push so hard, we're gonna crush it, we're gonna get to ten million ARR in 18 months, and at the same time, at any minute, someone could rel…”
The other half of the tape: Jordan Gal's own voice is left out of every number here. Other people bring the name up 28 times in 14 episodes across the shows. 1 statement on the record names them. every mention, with the transcript →
Who brings them up most Rob Walling 25Ruben Gamez 2Anthony Eden 1
Statements about Jordan Gal, by other people (1)
Gomez: CartHook's Upfront Application Friction Succeeded by Creating Exclusivity
“And he added this like crazy amount of friction up front by having an application that people would have to apply. And that helped reduce the amount of people that weren't a good fit, but it also had this side effect. It was like a exclusivity sort of thing, y…”
Every mention by year
tap a year for its mentions
Startups For the Rest of Us 28
2025 3 mentions in 3 episodes 1 per episode
2024 4 mentions in 3 episodes 1 per episode
2023 9 mentions in 3 episodes 3 per episode
2021 1 mention in 1 episode
2020 11 mentions in 4 episodes 3 per episode
- Episode 501 | A Bluetick Update from Mike #Taber
- Episode 509 | Revisiting the Six Stages of SaaS Growth with DNSimple
- Episode 504 | 15 Tools We Use to Run Our Business
- Episode 495 | Advice, Competition, Marketing, and Managing Developers (A Rob Solo Adventure)
- every mention in 2020, scene by scene →
One line per show, most statements first. The link opens Jordan's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| STARTUPS FOR THE REST OF USLEDGER | Co-founder & CEO, Rosie | 7 | 52 | 25% 1/4 | full record on Startups For the Rest of Us → |