Jason Calacanis advises against offering free tiers for startup products, arguing that requiring payment (even a small amount) creates 'skin in the game' that filters out casual users and attracts serious customers. He demonstrates this principle through his Founder University program, where completion rates jumped from 20% to over 90% after implementing a $500 refundable deposit requirement. Instead of free versions, he recommends offering cheap paid trials or scholarship paths for those who genuinely cannot afford the service.
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J-Cal founder tip: don’t have a free tier
Added:Polly is an AI that builds and runs your company as you sleep. So, you give it an idea and it's not go about building the product, fixing the bugs, running support, running meta ads even, and really go and you know, build your company with your guidance.
Every night it does work and then in the morning will send you an email with a summary of what it's what it has done, what it will do next, and and and of course you can reply to that email, you can tell it what you want to do and like it will remember what you said and like keep on going. So, sort of like an AI co-founder that like that like just build and build with you without never giving up.
>> Awesome.
>> Yeah, when we were on the show I was like I think it was like at a 100 200k run rate at the time and and there was a lot of hype around around the company because I was actually letting my AI do the fundraising.
And right now I'm at 10 million run rate plus. So, I've got a lot of that in a few months.
>> And people will pay you to use the platform. So, founders pay a monthly fee, yeah?
>> Exactly, yeah. Yeah, essentially you you got a you hire Polly the AI to be your co-founder and like if you if you pay it like it will work for you.
I'm actually trying to make it way more affordable and try to build a free version.
Don't do it. And No.
>> [laughter] >> As your as your unofficial advisor, I say no.
No free version. You know why? Cuz she then you're going to get looky-loos and you know, give them a two-week trial, but I you know, I think you have to have skin in the game. And there's so many people who distract founders with these free versions. Tell me why you're considering a free version. Why? You want to democratize it?
>> I think that like you know, the the people who use it love it so much and I think autonomy is a very new field and I think actually the very few companies even the open and Google's don't offer like a true autonomous AI that is in your inbox every day that is here to guide you and and make sure founder make sure builder. I believe that society needs a lot more founders and a lot of more builders to make it a great society. Uh because you know you don't want to worry about like everyone's on on food stamps because uh the government has >> listen. I agree with you, but I got you covered. This Week in Startups and the other 50 copycat uh tech startup programs are giving people plenty of inspiration. Your job is to get them serious and it gets serious when you take a credit card out.
So, I don't know, man. You could give like a six-week trial for 20 bucks or you could do a startup program where people can email you if they can't afford it, but you know, I had this issue with Founder University and the number of people who would complete my 12-week pre-accelerator year zero unincorporated companies, which is, you know, analogous to what you're doing, you we would have like a 20% rate. Then I made it $500 to secure your spot and said if you come to all 24 sessions, you or your co-founder, which is only 2 hours a week, 3 hours a week, you get your $500 back. All of a sudden 90 plus percent completed the course.
And uh for the, you know, whatever 30 people who didn't, we got $15,000, which paid for the return fees, uh you know, that we had to pay to return people's money and the credit card fees. So, we didn't make any money off of it, but we did have them have skin in the game. So, anyway, that's my advice to you. You take it if you want it.
>> If you're building a startup, you already know how painful legacy systems can be and health care might be the worst one. Crowd Health gives founders, operators, and startup teams a different way to pay for health care without the usual insurance bureaucracy. Now, Crowd Health is not insurance. It's a peer-to-peer funding platform where members help fund each other's medical expenses with a team that helps you navigate bills, find fair prices, and avoid getting buried in paperwork. So, for lean teams, for freelancers, and for early-stage builders who want more control over healthcare costs, CrowdHealth is worth a look. You can get started for $99 a month for your first 3 months if you use the code twist at join.crowdhealth.com/twist.
Again, that's join.crowdhealth.com/twist.
Use the code twist, save some money, and get that bureaucracy under control.
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