How to Raise a Seed Round in 2026: Ask Jason | E2294

Summary

Podcast Summary: This Week in Startups

Episode: How to Raise a Seed Round in 2026: Ask Jason | E2294

Host: Jason Calacanis
Date: May 29, 2026

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Brief Overview

In this lively and insightful Q&A episode, Jason Calacanis, alongside Lon Harris and Jacob from the Twist team, fields hard-hitting and wide-ranging questions from their private community chat. Topics include strategies for raising a seed round in 2026, standing out in an AI-dominated landscape, community building and founder education, investor-founder alignment, hardware startups, and candid reflections on some of Silicon Valley’s most controversial figures. Blending tactical advice, personal anecdotes, and industry insider knowledge, the episode offers a rich field manual for aspiring founders.

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Key Discussion Points & Insights

1. Seed Fundraising Dynamics in 2026

Timestamp: 03:06–07:41

• Contact Volume & Funnel:
  Jason details the numbers-driven process of modern seed fundraising:

  "In order to get a seed round today, you need to contact 150 seed funds, get 50 meetings with seed funds to get... 15 second meetings, to get two to give you a term sheet. That’s the funnel today." — Jason Calacanis (06:18)

• Judge Investors by Track Record:
  He cautions founders to pay attention to investor behavior, not just supportive words:

  "You have to divorce what people say in social settings, especially investors, from their behavior." — Jason Calacanis (04:43)

• Stage Fit:
  Don’t waste time chasing later-stage investors who only say nice things. Instead, focus on those who regularly invest in your current stage:

  "What you want to look at is, do they actually invest in your stage of startup?" — Jason Calacanis (05:56)

2. Community, Founder Education & The Need for a “Founder Community College”

Timestamp: 08:05–16:18

• Founder Community College Concept:
  Jason is asked about the need for a program for single-person, AI-driven founders not focused on traditional fundraising.
  • He’s considered accreditation issues:

    "Turns out I’m not legally allowed to give a degree in being a founder or a degree in being a venture capitalist. I could give a certificate, but not a degree." — Jason Calacanis (09:59)

  • Describes the paid, immersive associate-in-training path at his own venture firm, contrasting it with expensive, elite programs like Kauffman Fellows (tuition $80k–90k for 2 years).
  • Suggests a possible partnership with universities for more legit credentials, and muses on packaging founder & investor education:

    "Maybe you put the two together and it’s just company building. And you have two tracks, the Founder University track and the Associate... Venture University track." — Jason Calacanis (15:31)

• Curriculum Value Adds:
  The program would also include media training and practical communication skills, which are lacking in current offerings:

  "You’d also come out of this knowing how to make a newsletter, knowing how to do social media, knowing how to make a podcast." — Jacob (15:49)

3. How Tech’s “Must-Haves” Have Changed

Timestamp: 18:14–23:09

• Cheap and Fast Product Launches:
  Jason details 20-year shifts in startup costs, from millions and big offices to near-zero with remote/no-code approaches:

  "It used to take 20, 30 people and $3 to $5 million dollars to get your product to market... Now... it's down to weeks, it's down to a weekend." — Jason Calacanis (19:16)

• No-Code & Cloud Era:
  Time from idea to users is dramatically compressed; what used to take a year can now be built in a matter of days.
• Bounties and Incubation:
  The team is experimenting with bounties to foster new product ideas and potentially incubate them.

4. Surviving in the Age of AI Giants

Timestamp: 23:21–29:22

• Question: How do startups differentiate when OpenAI, Anthropic, etc., move into their vertical?
• Community and UX Moat:
  Jason argues the answer is specialization and building community — AI giants will never customize their interfaces for niche user needs:

  "There’s always going to be a feature set that the interface of the large language model is not going to add because of clutter and confusion." — Jason Calacanis (23:52)

• Example: In travel, an LLM is good, but a startup can add multiplayer trip planning, curated guides, and on-the-ground support.

5. Finding True Alignment with Investors

Timestamp: 29:25–36:25

• Beyond Superficial Fit:
  Jason and Lon discuss how weak, noisy signal and poor coordination plague the founder/investor matchmaking process.
• Do Deep Research:
  Use Crunchbase, social media, and fund portfolio reviews to identify those most likely to fund your company.

  "It’s a bit bespoke and underground... It’s tedious, it’s a full time job. Treat it as such." — Jason Calacanis (33:05)

• Alternative Outreach:
  Sometimes the most creative approaches in dense ecosystems like SF — even sitting in a well-trafficked café with a "Pitch me" sign — can yield results.

6. Hardware Startups: New Respect

Timestamp: 37:19–41:32

• Hardware is Back:
  Jason says VCs have shifted from "hardware is hard" to "hardware is one of the only moats left":

  "Hardware is now a way to get lock-in... Hardware is no longer a blocker with investors, which is really fascinating to me." — Jason Calacanis (38:09)

• Robotics and 'Automatons as a Service' (AAS):
  The future of accessible robotics may look like a SaaS subscription model for robots:

  "You’ll just pay a $299 a month lease. And that gives you 500 hours of your robot’s time. If you go over, it’s a dollar extra." — Jason Calacanis (41:12)

7. Silicon Valley’s “Most Disliked” Figures

Timestamp: 42:20–46:59

• "Spicy" Question: Who does Jason really dislike most in Silicon Valley?
• Mark Zuckerberg:

  "I've been a consistent critic…Every time he had a chance to do the right thing for humanity, he picked his own self-interest over that of humanity..." — Jason Calacanis (43:23)

• Sam Altman:

  "Sam Altman I don’t like because he screwed Elon and Elon’s my friend and I watched it happen, but I kind of liked Sam, or I did like Sam interpersonally…" — Jason Calacanis (44:54)

  • Jason emphasizes these are business judgments, not personal vendettas.

8. Media, Reputation, and Hot Takes

Timestamp: 46:59–49:06

• Caution with Media Narratives:
  Jason stresses the importance of skepticism around viral news stories and “hot takes”:

  "I just don’t trust the media or any report now... I really think through before I pop off..." — Jason Calacanis (48:00)

• Lesson:
  Take time before forwarding or reacting emotionally to stories, especially in the current era of AI-generated misinformation.

9. Off Duty: Travel and Museum Culture

Timestamp: 50:00–57:50

• Italian & Greek Travels:
  Lon Harris recounts his first trip to Italy and Greece, sharing quirky personal stories and travel tips.
• Museum Etiquette:
  Jason and Lon lament the over-documenting tendencies of modern visitors:

  "Just be in the moment, folks. Just be in the moment... What are you documenting? Your life is incredibly boring. You’re the least important person within 100 miles of this place." — Jason Calacanis (52:03)

  • They suggest after-hours, premium museum experiences for smaller crowds and richer enjoyment.

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Memorable Quotes & Moments

• "Fun starts at $10 million. Once you have that... you can just exist."
  — Jason Calacanis (17:06)
• "It’s a sales funnel... you have to qualify each investor. Do they invest? Are they actively investing or is their fund in maintenance mode and they’re in between funds?"
  — Jason Calacanis (34:28)
• "Automatons as a Service. ASS would be your acronym. Yeah, they'll cover your ass."
  — Jacob & Jason Calacanis (41:23)
• "I've been a consistent critic of [Zuckerberg] … every time he had a chance to do the right thing for humanity, he picked his own self-interest."
  — Jason Calacanis (43:23)
• "I kind of liked Sam, or I did like Sam interpersonally... but he, you know, he kind of shiv'd my friend and I'm team Elon. Not cool..."
  — Jason Calacanis (44:54)

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Timestamps for Important Segments

• Seed Fundraising Funnel & Numbers: 03:06–07:41
• Founder Education & "Community College": 08:05–16:18
• Startup Costs Then vs. Now: 18:14–23:09
• Differentiating vs. AI Giants: 23:21–29:22
• True Founder-Investor Alignment: 29:25–36:25
• Hardware Startups & Robotics: 37:19–41:32
• Most Disliked in Silicon Valley: 42:20–46:59
• Media Skepticism & Lessons: 46:59–49:06
• Culture & Museums Rant: 50:00–57:50

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Tone and Style

The episode maintains Jason's classic mix of hard-nosed practicality, sharp wit, industry candor, and an undercurrent of founder optimism. Conversations are candid, direct, and laced with relatable humor — making it approachable for new and veteran founders alike.

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For Founders:

This episode serves as a masterclass in the current art of fundraising, building defensible AI startups, cultivating robust community, and navigating the idiosyncrasies of Silicon Valley. Jason’s guidance, peppered with both tactical to-dos and big picture reality checks, is invaluable listening for anyone serious about the startup game in 2026.

Transcript

[Jason Calacanis]

People in our secret group chat have questions for me. Some might be spicy.

[Lon Harris]

What do you think founders should be

[Jacob]

doing to try to sort of give themselves a little bit of moat against OpenAI?

[Jason Calacanis]

There's always going to be a feature set that the interface of the large language model is not going to add.

[Lon Harris]

Out of all the people in Silicon Valley, who's the one person you really

[Jacob]

don't like the most and why?

[Jason Calacanis]

Some people have damaged the reputation of the industry and the user base and then some people have just maybe screwed over friends of mine I've been a cat consistent critic of. Every time he had a chance to do the right thing for humanity, he

[Guest/Co-host]

picked his own self interest. It's a level of selfishness in decision making. That and cutthroatness that I understand, but I wouldn't do and I think has damaged the reputation of the tech industry. The two people I'm talking about are two of the most successful people ever in the history of business.

[Sponsor/Advertisement Voice]

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[Guest/Co-host]

All right, Lon Harris is here. I'm Jason Calacanis. People in our secret group chat on

[Jason Calacanis]

X formerly known as Twitter have questions for me. I'm going to answer them. Lon is going to give me these questions he's vetted some. Might be spicy, could be political, it could be technical, it could be startup related, it could be life, it could be health, could be dating, can be anything. I'll answer any question for our community if they have it. If you want to join our community x.com twistartups that's our handle. If you DM that handle, we know that you listen to the pod and we will add you to that group. The group's got 400 people in it or so and it's quite a nice little group talking about the topics of this week in startups of Twist. Let's get started.

[Lon Harris]

Yeah, I would add if you're very active in the group and participating and sharing great stuff.

[Jacob]

Thank you. There's Even a higher level insiders group. Maybe you can add that one that's very rarefied. We don't, we don't just let anybody into that one.

[Jason Calacanis]

It's a funnel. We have everybody following the account.

[Guest/Co-host]

Then we have four or five hundred people in this crazy group chat and

[Jason Calacanis]

then I think we have 10 people

[Guest/Co-host]

who are like the best people in

[Jason Calacanis]

the group chat, who we know are

[Guest/Co-host]

good actors that we're filtering into, like just a small group. So it's.

[Jason Calacanis]

I don't know exactly how to build

[Guest/Co-host]

community this day and age, but I'm going to start doing more dinners and live shows since people want to get together in person and a lot of people are sad and lonely and staying at their ranch, smoking cigars, sitting on a bench and want to see more

[Jacob]

humans get out in the world.

[Guest/Co-host]

Yeah, that's what I want to do. I need to get out in the world more. So yeah, more dinners, more hanging out, more live shows.

[Lon Harris]

So first question comes from Richard Corral of Quanto. It is a accounting firm in the age of AI.

[Jacob]

Here I'll share their website.

[Lon Harris]

They are basically, he describes it as an AI powered wealth management platform. And so here, here is his question. We have a $10 trillion a lead interested in us as clients and investors. They gave never seen something like this before level feedback but then ultimately told the company they're too early for now, but they want to stay updated. So Richard wants to know your advice on how to combat the challenges facing startups with that early stage status, even when their tech is advanced and innovative and looking forward.

[Guest/Co-host]

Sure. Each investor has a different area of speciality and you should look at what stage of a startup they invest in most and whatever they tell you is not as important as what they do.

[Lon Harris]

Right.

[Guest/Co-host]

So if you were looking at a person and trying to judge them. The best way to judge a person is to look at their previous behavior or to watch them doing the job you're asking them to do. This is first principles thinking. If you go to a family office and you are in year zero of your startup, you are not incorporated yet, you have a, you know, a demo, a product, they're not going to invest unless they have a history of investing in entrepreneurs who are not yet incorporated and who don't have a product in market yet.

[Jason Calacanis]

Now you have to divorce what people say in social settings, especially investors, from their behavior. If you look at my firm, Founder University is designed as a product occurring in three different geographies, three different continents around the world twice a year, each

[Guest/Co-host]

six cohorts a year. Riyadh, Tokyo and in the US and we explicitly ask people to come who have two or three founders and you don't need to be incorporated, you don't need to have customers yet.

[Jason Calacanis]

We want to meet you in year

[Guest/Co-host]

zero and then the accelerator, we want to invest and we want you to be incorporated at that point. Now, if you go to a family office and they've invested in seven things in the last five years, and all of those things are private equity deals

[Jason Calacanis]

that their friends brought them, and they

[Guest/Co-host]

put $30 million into each deal, how on earth are you going to put 125k or 250k or what you're looking for in your seed?

[Jason Calacanis]

They're not.

[Guest/Co-host]

But you got introduced to them, they took the meeting. They're going to say nice things. You have to divorce the nice things they're saying from the reality of what they do.

[Jason Calacanis]

That's all you have now, somebody who likes you. Okay, great.

[Guest/Co-host]

But they say that to everybody. What you want to look at is, do they actually invest in your stage of startup?

[Jason Calacanis]

The answer is probably no.

[Guest/Co-host]

Therefore, who does Invest? Y Combinator, Techstars, Antler A16Z, Pear has

[Jason Calacanis]

a great summer program, Sequoia has Ark,

[Guest/Co-host]

I have founder, university, launch, accelerator.

[Jason Calacanis]

Go to those programs first. Get your 125k, your 25k check, your

[Guest/Co-host]

250k check, get your first five customers, and then you can go back to them and they might be a greater later stage. And in terms of numbers, in order to get a seed round today, you need to contact 150 seed funds, get 50 meetings with seed funds to get

[Jason Calacanis]

22nd meetings, to get two to give

[Guest/Co-host]

you a term sheet. That's the funnel today.

[Jacob]

Yeah.

[Guest/Co-host]

If you're not doing that, you're just not playing the game. On the field. You may hear of people who get funded, they take a meeting and they instantly get funded and they weren't even looking for funding. Yeah, those are memorable stories because they are not the norm. They're notable because it's not the norm. That's why you're hearing those stories. The norm that we see on the field is emailing and trying to get in touch with 150 different investors getting on the radar and getting a quick Zoom call with 50 getting 10 or 20 of those. In other words, 10% of your initial target list to take a second meeting. 150 targets, 15 second meetings. That would be a reasonable goal. Yeah. If people are not willing to take a second meeting, you're not really. You should really Only judge second meetings. People are not obligated to take a second meeting, therefore a second meeting is notable. Okay, I hope that helps.

[Lon Harris]

Yeah, I think that's, it's interesting. It's how, how many different sort of fields and kinds of work that's applicable to like people think to become a content creator you just create like two or three videos and then one goes

[Jacob]

viral and now you're Mr. Beast and it's like, no, it's hitting

[Lon Harris]

it every single day, it's doing it hundreds of times until you find your

[Jacob]

voice and refine everything and then you start actually growing.

[Lon Harris]

And I think it's kind of the

[Jacob]

same across just about any discipline.

[Lon Harris]

All right, speaking of Founder University at On Protons on X had a pitch for you for what they call Founder Community College. So their question is, why is there no Founder Community College to go alongside Founder University? It would help with the coming wave of 500k to $5 million AI driven single person owner operated companies. So you're not worried about fundraising, you're not worried about board seats, you're not worried about cap tables. It's just focused on tools and building great products. What do you think is there, can you see a level between, you know, Founder University that's for, you know, people

[Jason Calacanis]

who are even earlier so funny they mentioned this. I literally this weekend was asking about the accreditation laws and how I could give a degree. I was asking this because we have an associate in training program for the venture side of our business. We're hiring six people in June to be part of that. They start as researchers, they become analysts, then they become associates. It's a basically a three year program to go through each of those titles. 60, 70, 80, 90K is like sort of the career path in terms of salary. So instead of paying for a degree

[Guest/Co-host]

in venture capital, we pay you is the way I tell people to look at it.

[Jason Calacanis]

And we hire twice as many people, really three times as many people as

[Guest/Co-host]

we need because we think one or two of them are going to opt out.

[Jason Calacanis]

It will be like not the career for them. One or two of them we will not continue on with.

[Guest/Co-host]

In other words, we don't think they have what it takes.

[Jason Calacanis]

And then 1/3 we're going to keep

[Guest/Co-host]

and they're going to become all stars in our firm and we want to replenish that. But I had so many people say to me, I would like to send my child to that.

[Jason Calacanis]

Can you charge me 60k a year

[Guest/Co-host]

for 2 years and I'll pay you 120k. To teach them how to be a venture capitalist. Because there is no course in that. There's like education. It turns out I'm not legally allowed to give a degree in being a

[Jason Calacanis]

founder or a degree in being

[Guest/Co-host]

a venture capitalist. I could give a certificate, but not a degree. When you're a founder and you're moving fast and you want to close a big deal, a traditional bank can kill your momentum. Long approval processes, clunky, outdated systems, not intuitive. I mean, some of these systems look like they were made in the 1970s and have never been updated. Not all banks are designed to work for startups. We all know that. And that's exactly why Grasshopper bank was created. Grasshopper is a real federally charted bank, but with the kind of financial tech stack that you'd build for yourself.

[Jason Calacanis]

They're going to open your new account in just minutes, not days.

[Guest/Co-host]

That's a key pain point.

[Jason Calacanis]

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[Guest/Co-host]

And so that's what I think a lot of people do with these continuing ed certificates, et cetera. So I would have to partner with a local university in the US to do this. And there are some that do this. But you can give certificates or a diploma, but you cannot give a degree. That's the word that I think gets you in trouble. Now, outside the US there are some universities in the UK that will let you use their programs to do a UK accredited degree. And then there are islands, like there were some islands people would go get degrees in medical practices.

[Jacob]

Sure, yeah. I mean, I know that's a big like Central American thing. People go down there to get their degrees.

[Jason Calacanis]

Right. And like dentistry and other things. And it does somehow work in the United States. I don't know about those. It seems. Fugazi. Fugazi. But I have been thinking about this because I do think college is broken. So next year I told my team I want the associate in training program that we start in the summers to be so good this time. And you and I were talking with Jackie about it. We're going to have a Monday morning session and a Friday end of the week session where we do professional training and then in between they work at one of the business units inside the company. The goal I think is for that training program, those two two hour sessions that bookmark the week to be so good that next summer when we do it, we could literally charge for it and literally say for $50,000, you can come work here for nine months out

[Guest/Co-host]

of the year, take your summers off or 10 months and for two years and then take on Kaufman Fellows. There's a program called Kaufman Fellows. You can pull it up on the screen. Kaufman Fellows charges, I believe, 80 or

[Jason Calacanis]

$90,000 for two years.

[Guest/Co-host]

Somebody look up the price. It was extraordinary.

[Jason Calacanis]

And then they were like, oh, well,

[Guest/Co-host]

that's for people who are already in it. So Kauffman Fellows is this program that people do and you can see it's incredibly diverse. They have like scholarships and stuff like that. Because our industry, the venture industry was known for maybe 10 years ago a little too, dare I say, Mal and White and Ivy League, sure. But they've had a thousand fellows. Some of them you might know. There's Jenny Fieldling, I know her. And I don't know which one of these peoples are paying for it. There's Monique Woodard, I'm an LP in her fund.

[Jason Calacanis]

So I don't think there's anything wrong

[Guest/Co-host]

with this program necessarily. There's Mamoon, but I do think it's a bit of an elitist group and It's I think $90,000 a year.

[Lon Harris]

I don't know if someone has looked it up. Jacob looked at producer.

[Jacob]

Jacob looked it up for us.

[Lon Harris]

The Kaufman Fellows two year program tuition is $80,000. Application fee of $100 if submitted by the early deadline. If you missed that, it's a $300

[Jacob]

application before the actual end of time deadline.

[Jason Calacanis]

So I think I could have 10 people in this program charge them 50k each. That'd be 500k. Then I could hire 2 full time people to work on it and create a program. And I think it would be better than co. I know it would be better than Kaufman Fellows because you get to come with me to Saudi, come with me to Tokyo, see those programs and interview companies and I think they're not even in office for that much. I don't think that this. I think this program is all virtual.

[Jacob]

I think they maybe spend a couple weeks together mostly.

[Jason Calacanis]

But I wonder like what the actual curriculum is. If somebody could send me the curriculum or send me like the agenda and what it. I would love to study what Kaufman has done. I don't know if it's public, but anyways, I'm not dissing them for having an incredibly overpriced, elitist program. I am thinking on a competitive basis, like maybe I could create a better program. And then for Founder University, I would be fine with partnering with a university that wanted to give a Founder University degree and make it a two year program. And it just teaches you how to be a founder and embed you in companies. I mean, sure, why not?

[Jacob]

There's probably some young people that would be interested.

[Lon Harris]

They are interested in entrepreneurship, but wouldn't

[Jacob]

even know where to get started. I feel like that's what Founder University is good for.

[Lon Harris]

Like Here are the 10 terms you don't know.

[Jacob]

Here are the concepts everybody's talking about that you're not familiar with. Like that's where I think we can really help young.

[Jason Calacanis]

Or maybe you put the two together and it's just company building. And you have two tracks, the founder University track and the associate.

[Lon Harris]

Right.

[Jason Calacanis]

The venture University track.

[Guest/Co-host]

You have the two tracks and you

[Jason Calacanis]

major in one minor in the other.

[Guest/Co-host]

But you learn both sides of the table.

[Lon Harris]

And I mean we're also. I bet you coffin fellows is not doing media training.

[Jacob]

You'd also come out of this knowing how to make a newsletter, knowing how to do social media, knowing how to make a podcast. You know, like all those communication skills

[Lon Harris]

that you wouldn't get that are so important in this field. I mean we talk about all the time because we're constantly booking investors and

[Jacob]

venture capitalists and founders as guests.

[Lon Harris]

But there are a lot of brilliant founders with great companies or brilliant investors with great portfolios.

[Jacob]

But they are dead air on a podcast. You can't book them on things.

[Guest/Co-host]

Yeah, for sure.

[Lon Harris]

And so like we also help with

[Jacob]

those skills that are important as well.

[Guest/Co-host]

Yeah.

[Jason Calacanis]

Now unfortunately, because some idiot started a podcast about startups 16 years ago and

[Guest/Co-host]

now every venture capitalist has to have a podcast.

[Jacob]

Yeah. Geez. Those four billionaires got together to so brutal.

[Jason Calacanis]

And now especially since one of them is not a billionaire, I think they three of them are not real.

[Jacob]

Technically, that's breaking news. Huge if true.

[Jason Calacanis]

Yeah, I don't think Freeberg's a billionaire. Maybe on paper with oh, hollow stock. I mean people refer. I don't think ch's a billionaire. I don't know.

[Lon Harris]

People just refer to you all as billionaires.

[Jacob]

I just assumed, I've just been guided

[Jason Calacanis]

this might be a billionaire.

[Jacob]

I don't know, I feel like yeah, Saxon chamath maybe pretty close. Maybe chamath after that Grock deal. Come on.

[Jason Calacanis]

I think he probably owned 10, 20%.

[Lon Harris]

Yeah. And maybe like, obviously not liquid, but

[Jacob]

I, I, I feel like he's probably.

[Jason Calacanis]

Yeah, I mean, that's the always. The thing is like, and then who cares?

[Guest/Co-host]

Like, hon, the more I look at wealth, wealth creation. Once you get past like this basic $10 million mark, you have the fu. Money, you have the fun. And once you have fun, it doesn't matter. You could ski, you could podcast, you could do whatever you want. And it's exactly $10 million. I think that that's exactly the fumes number. Fun starts at 10. Once you have that, you make 5% on your money, which is a half million dollars a year, which means, you know, after taxes, four or 500, 000 a year, you can just exist.

[Lon Harris]

Yeah.

[Jacob]

I'd be back in Florence right now.

[Guest/Co-host]

You'd be back. How was your trip, by the way?

[Jacob]

Amazing trip. I had a great time. Yeah.

[Lon Harris]

Rome. Rome.

[Guest/Co-host]

How many days did I give you off?

[Lon Harris]

It was, you kept saying 22. It was technically 19 days off and a lot of those were weekends. Some of the. So it was like, okay, I think it was like 14 work days off total.

[Guest/Co-host]

It felt like you were gone for two months. My God, you definitely have job security. I was like, I'm ccing lawn. And I'm like, jesus, when is this guy going to be back?

[Jason Calacanis]

All right, give me another question.

[Lon Harris]

All right, let's go into number three. This is from Serge Dog, also on X.

[Jason Calacanis]

If you love Surge.

[Lon Harris]

If you compare early stage startups today to 10 years ago, what has changed the most in how you evaluate them? And in particular he's interested in what do investors overvalue, do you think, from the like, old school conventional wisdom playbook? What traditional must haves have become optional and what expectations are now table stakes? Like how, how has the landscape shifted

[Jacob]

for you as a investor in early stage?

[Jason Calacanis]

Yeah, I mean the number one thing is the amount of capital it takes to get a product to market and to the amount of time it takes to get product market fit that is dramatically decreased. So over time, we with vibe coding or the no code revolution, we had these moments where it seemed like really no code was one cloud, the cloud era was another where the cost of running a startup went down. 10x used to be 3 million, then

[Guest/Co-host]

it went to 300.

[Jason Calacanis]

And when that happened, because of wework,

[Guest/Co-host]

outsourced accounting and legal and not having to stand up your own data center, it used to take 20, 30 people and 3 to 5 million dollars to get your product to market, that was in the web, 1.0 ERA. The 90s seed round would be 3 million. It would take 12 months to get your product ready to go to market. And you had all of these expenses which were considered non negotiable and you had to do them. You had to have a PR firm, 10k a month for 18 months, 180k. You had to get an office for 25k a month. You had to put a 250k letter of credit down. So that was another 300,000 a year for two years, 600,250k letter of credit. It was basically a million dollars. To set up your office, you had to put a half million into service. Now you have 1.5 million. You had to spend 100k on legal, 1.6 million. You had to hire an HR person, an accountant and a lawyer, another 250k. Now you're at 1.8, 1.9 million. You get the idea. Then you hired a couple of product people, developers. You're at $3 million. You finally get the product launch and you figure out if you're going to win or not.

[Jason Calacanis]

Adding a new member to your team is a crucial decision and you don't want to rush into a hiring situation that you, you will regret.

[Guest/Co-host]

But if you're a busy founder, you

[Jason Calacanis]

also don't want to spend a ton of time in the trenches looking for that perfect candidate. Instead, you need a partner and you need a trusted partner. And LinkedIn Hiring Pro is that partner. How do I know this? Because I use LinkedIn Hiring Pro. You want a real world testimony. All right, here you go. We recently hired a new customer success manager. They handle all the advertising accounts here on this Week in Startups and they ensure that we're keeping all of our wonderful partners happy. LinkedIn helped us connect with an amazing candidate right here in Austin. And he had exactly the combination of experience we were looking for. It's magic, it's alchemy, it's everything for

[Guest/Co-host]

me to find a great team member.

[Jason Calacanis]

So hire right the first time. Get started by posting your job for [e-mail] twist. Terms and conditions apply. That's LinkedIn.com twist.

[Guest/Co-host]

Then the Y combinator error, the cloud computing error meant you work at home, three people, you eat ramen for 300k. You could stand up a startup in under six months. Now, then it went to like 30k, just paying for some servers, but maybe you got free credits and you and your partners never met in person and you just shipped and You Vibe coded stuff and you got your first customer. Then you applied to Y Combinator or techstars or Antler or one of these incredible programs, Launch Accelerator. Now it's kind of like I built a. I vibe coded a product. I got to 100k in revenue and then I applied to Y Combinator, then I applied to Launch Accelerator. So that's what we're seeing. And so the time from idea to first customer and first customer is light product market fit. You can convince people to pay for anything, but let's just say some level of product market fit that's down to weeks, it's down to a weekend.

[Jacob]

Yeah.

[Lon Harris]

I was going to say it's not just because days. We've seen companies on the last few

[Jacob]

months of the show that are literally like, oh, I built this 14 days ago. And we're talking to them on the show about all of their hundreds of customers.

[Jason Calacanis]

Our bounties program is a perfect example of that. We have two bounties out this week in startups.com bounties or bounty, and the one for the fact checker, Real Time fact Checker. We got 15 people and I think three of them are really good. That was like in under 30 days. And then we're doing another one, another $5,000 bounty for annotated. What I'd like to do with one

[Guest/Co-host]

of those companies is actually make it a startup.

[Jason Calacanis]

So I'll give them the prize, but then I want to hire them and incubate the startup. So that's my hope, is that the Real Time fact checker becomes an actual startup company or Annotated becomes a real startup. So I'm hoping to find a founder or two I can hire and put into like a startup or a company I incubate.

[Lon Harris]

And by the time this airs on vod, we'll have already picked a winner

[Jacob]

for our sidecast or live producer winners or multiple winners. You never know. We've seen some amazing submissions. There are really some great submissions.

[Lon Harris]

All right, next question from founder university vet Mahika Galani of a company called Treya. She wants to know how should startups think about differentiating when Frontier Labs release products in the same vertical that they're building in?

[Jacob]

Of course, this is a huge story. People are always worried about are they going to get death by Clauded and is Anthropic going to just take over their business?

[Lon Harris]

So what do you think founders should

[Jacob]

be doing to try to sort of

[Lon Harris]

early differentiate, give themselves a little bit

[Jacob]

of moat against OpenAI anthropic and others, absolutely.

[Jason Calacanis]

So there's always going to be a feature set that the interface of the large language model is not going to add because of clutter and confusion. So let's take travel. We had a great startup, Rome and they I think were built on like the Preview, like the 2.5 of. And you can look up Rome and we probably have it in our database here. I think they wound up giving the money back to investors because in ChatGPT 2.5 that was like an API and then they were letting you put in, I want a three day trip, I want to go to Italy. I have three weeks. My boss gave me 19 days to

[Guest/Co-host]

be out of the office.

[Jacob]

That was great.

[Jason Calacanis]

What should I do over my 19 days? Because my boss is so goddamn accommodating. And Rome was like one of the best previews I've ever seen.

[Guest/Co-host]

It's in our database.

[Jason Calacanis]

It's not public because it shut down. But let's take that one as a travel example.

[Guest/Co-host]

You can ask all these travel questions inside of ChatGPT and people do.

[Jason Calacanis]

But if you were to build an

[Guest/Co-host]

interface around it and features around it and you're constantly adding features and then

[Jason Calacanis]

building a community around it, the community,

[Guest/Co-host]

the support, these extra features, they're not what ChatGPT is going to work on. They're just going to ChatGPT X, they're going to just give you your basic output. But what if you want, when you get the basic output, you want to play multiplayer mode. So you and I and Amanda and William and Bianca are doing our next trip to Tokyo and we're like, hey, let's do this as a group. Let's all research where we want to go for three days on a bullet train. Let's all research where we want to go for breakfast, lunch, dinner and shopping. And then we all do our research. But we're watching each other do the research and then we click and we vote and we add it to an agenda and then we finalize the agenda. All that stuff roam around was the company. That's not going to be done by ChatGPT. So you can build all that around it. And then you could build the concept of a virtual travel agency. Somebody who uses AI and does all this itinerary with them and you pay them per hour to do it, or you pay them for ground support. When you're on the ground in Tokyo, they match you with a local guide. Those things will not be done by ChatGPT, if that makes sense. Right. So that's, I think the differentiator you

[Jason Calacanis]

can do Tax GPT.

[Guest/Co-host]

Another example of it.

[Lon Harris]

I was just gonna say, having just planned a trip, you do look things up on AI. It's natural. I use it in place of a

[Jacob]

search engine at this point.

[Lon Harris]

But then there's also Viador and TripAdvisor

[Jacob]

and all these other platforms.

[Lon Harris]

And it's using both.

[Jacob]

It's not one or the other. Like, I think a lot of people think it's sort of, you know, you

[Lon Harris]

layer these different tools on top of

[Jacob]

one another to get the best results. So I think there's truth in that.

[Jason Calacanis]

I think community multiplayer mode support services around those things, they're just not going to do that. They're not going to create a marketplace with local guides. One of the things I want to do when I go to Japan next time is there are now food guides who have come out. And, you know, one of the things is because of social media, everybody goes and, you know, does a video of the memorable stuff.

[Jacob]

Right.

[Jason Calacanis]

And then all the influencers go there. But it turns out, like, unless you speak Japanese and, you know, the surrounding area, those places are targeting American tourists. But there's 20 other places with pancakes that are just as good or better, that don't have a line and you can hire. There's one guy who's a bit robust

[Guest/Co-host]

and his thing is like, he's. I don't know if he uses the term fat or, you know, whatever. He's your jolly fat guy who takes you on tour.

[Jacob]

That's amazing.

[Jason Calacanis]

And I guess there was a movie.

[Guest/Co-host]

Yeah, there was a movie about, like,

[Jacob]

Brendan Fraser was in about, like rental family. Yes.

[Guest/Co-host]

And the concept is he's an American

[Lon Harris]

actor and he's hired to pretend to be like a surrogate father in this

[Jacob]

family that doesn't have a dad around.

[Lon Harris]

And apparently this is. I mean, the story behind the movie is that this is a real service

[Jacob]

in Japan that you can, like, rent

[Lon Harris]

a fake family member for occasions or

[Jacob]

for times where you are particularly missing having, like a dad around. And then he becomes, of course, bonded

[Lon Harris]

with the family and it becomes a

[Jacob]

sweet story like that.

[Jason Calacanis]

You could also do rent an old guy for fun.

[Lon Harris]

Yes.

[Jason Calacanis]

So that is a thing. There's a rent an old guy boyfriend,

[Lon Harris]

rent a girlfriend services. Those get talked about a lot. And it's not a sex worker thing. It's just like, I want somebody to go to this ball game with, you

[Jacob]

know, like, it's that kind of thing.

[Jason Calacanis]

Yeah. But the. The renting a food thing is like, that's even better. So let's Say you have this idea for an AI planner, but then the AI planner has to result in something like you're on the ground. Okay. So you get the basic ChatGPT features for free, but we could also connect you with somebody who books this or gets in line for you, brings you, translates it sits with you, gives you the backstory, takes you and arranges for you to go in the back and make the ramen, you know, between, you know, lunch and dinner service.

[Jacob]

Yeah.

[Lon Harris]

In Rome, we booked a.

[Jacob]

One of those golf cart tours or the guys drive you around in the golf course.

[Lon Harris]

We got to go into a bunch of crypts and stuff under the churches because he like, would give. He would give the nuns like 5 Euro. He knew where to go and, like,

[Jacob]

who to talk to. So we got to see like genius,

[Lon Harris]

the tomb of St. Cecilia and all

[Jacob]

this sort of aqueduct under the Trevi Fountain stuff that most tourists don't get into, which is cool.

[Lon Harris]

So, yeah, I think that's a. Yeah, there's, there's a. There's a service there if you can

[Jacob]

find your sort of spot in the stack. Yeah, for sure.

[Lon Harris]

So from tripara.onx, they are a dating app for serious daters.

[Jacob]

I'll bring it up here on the screen.

[Lon Harris]

They compare it to being like. It's like being set up by a

[Jacob]

friend as opposed to just standing on

[Lon Harris]

an app by women for women. A new take on the dating app that is their business. Their question, and I quote from. Founders are often told to find the right investor, but most advice reduces to stage sector or warm intros. When you evaluate founders, what tells you there is real alignment beyond the obvious category fit? And then the founder adds. They're asking because fundraising feels to them like a marketplace with weak signals and poor coordination. They feel like the best founder investor matches are not just about who invests in their space, but who sees their problem the same way that they do.

[Jacob]

Your thoughts?

[Jason Calacanis]

Okay, so you have identified a real problem and you put together a solid solution and a business model that you believe in. So you're all set to launch your new company, right? Not so fast. If you want investors and potential customers to take your new business seriously, you

[Guest/Co-host]

need to consider forming a Delaware C

[Jason Calacanis]

corp. And that's where Northwest registered Agent comes in. They're going to give your new company a real identity. That means an address for your public filings, a domain, a custom website, a business email, and of course a phone number. And that's going to take just 10 minutes and 10 clicks. They don't charge hidden Fees, customer service is available around the clock. They're not overwhelming your inbox with spam, and they make it easy to cancel at any time.

[Guest/Co-host]

So get all the advantages of a Delaware C Corp. Independent, regardless of where in the US you're operating from. Visit northwestregisteredagent.com twist for more details and the links are in the show notes.

[Jason Calacanis]

Okay, so there are investors who. Investors have all different sets of signal and processes in which they invest. I have a friend who's an investor at True Ventures. He only invests on things that come through his network. He's an older guy, he's probably 60 now, and he basically looked at his career of 40 years or 30 years and said, you know what? All the great investments came when one of my friends told me about a company, therefore I'm not taking any emails. People can email me all they want. The only way I'm taking a meeting is if another venture capitalist or a portfolio founder tells me I should meet with it. And he just uses that as his filter and I think it works for him. Then there are people like y Combinator or us. You come to launch co apply. We meet with 10% of the companies that apply every week. So some weeks we get 200 people applying, sometimes 500. We meet with 25 people a week. Now we were meeting with 140. That was too much. So we meet with those 25 at the end of the year. You know, all said and done, we've done 3, 4, 5,000 meetings and we've invested in 100 companies called down from 10 to 20,000 applications. You get the idea. But we don't invest in biotech or military tech. Right now we're looking at military. We actually started with military tech, but we didn't do biotech. We didn't previously do biotech. You know, and everybody's got a different preference. So figuring that out is hard and it's work. And I think the best thing to do is to study what people have already done. You get a Crunchbase account or any of those things, you start following on social media, the different firms, and figure out 150 different firms that invest at your stage and have invested in similar companies. So if you're a marketplace and they did Uber or Thumbtack like I did, or they're doing fintech like I did Wealthfront and Robinhood, you can know that when you come to me, we share that. So if you're doing a fintech marketplace,

[Guest/Co-host]

you can be like, hey, jcal, you did thumbtack and you also did Robinhood. We're doing a marketplace for financial advisors and you pay financial advisors by the hour instead of 1% of your net worth or your portfolio size. And I'd be like, oh yeah, that's a really good idea. I would love to hear that pitch. Yes. So that's your job. And you have realized now as an investor that this is not a clean, easy to navigate marketplace. It's a bit bespoke and underground. We have a product called Whisper Network for our founders where they get to go in and search through and put in their materials, ask us for an introduction. And even with that tool, it's still hard. You're hunting, you're pecking, you're doing research. I think AI will make it a little bit better. But it's your job, it's tedious, it's a full time job. Treat it as such. That's why if you have three, three, three co founders in a company, one of them can focus on the product, one can focus on sales, and one can focus on corporate development. Corporate development is another fancy way of saying raising money. Yeah. And that's what you need to do. You have to look at fundraising as a full time job. You have to collect investors and build deep, meaningful relationships with them over time.

[Lon Harris]

Sort of the same.

[Jacob]

Less is more, number one. Like it's just, it's about legwork and putting in the hours and you know,

[Lon Harris]

shoes on the pavement as they say.

[Jacob]

You know, it's like about just hitting the streets. And here it's a sales funnel.

[Guest/Co-host]

You have to qualify each sale. Are you qualifying each investor? Do they invest? Have they invested in your stage? Are they actively investing or is their fund in maintenance mode and they're in between funds? What check size do they do? Do they lead a deal or do they follow a deal? Are they like my friend and they only take intros from existing founders?

[Jason Calacanis]

Okay.

[Guest/Co-host]

Then you have to do the work to meet one of their founders then in order to meet them. Okay, are you willing to do that work? So if you have 10 great VCs you want to meet with, maybe your best strategy is reaching out to five of their founders, meeting two of them and then using those two founders to get one of them to introduce you to a partner over there. Now you're talking about sending 50 emails to founders to get 20 meetings to maybe get on the radar of those 10 venture firms, maybe get on the radar of three or four of them. So again, that's the sales funnel.

[Jacob]

Yeah, it's like, it's like and you

[Guest/Co-host]

have to treat us.

[Lon Harris]

It's like when you're applying for your summer jobs as a teen and you

[Jacob]

know, like at first you're like, I

[Lon Harris]

filled out three applications. I went to the ice cream store and the bookstore and. And it's like, no, no, you got

[Jacob]

to fill out a hundred applications to get that one interview and to get that job. It's the same kind of story.

[Jason Calacanis]

And, you know, you can be creative about it. Like, there was somebody I saw who went to San Francisco and put the pitch. Somebody can look it up here in the producing team. They put the pitch for their startup on the back of their laptop and they just sat there in a cafe in South Park, I believe, which is not south park, the TV show, but

[Guest/Co-host]

a little park in San Francisco where

[Jason Calacanis]

there's a couple of CAFES and there's VCs tend to be around that park

[Guest/Co-host]

where there's some number of VCs.

[Jason Calacanis]

And they just said, I'm going to sit here and run into some people. And there was a Paul Graham quote or a video clip that went viral recently. It turns out San Francisco and the Bay Area are very unique in that the startup culture there is to help people without an expectation of short term rewards. And everybody helps everybody.

[Guest/Co-host]

This podcast was my way to give back, and that's why I've done 2,000 episodes of it. People tell me all the time, oh my God, you really helped me. I'm like, okay, I've never met you. They're like, oh, no. I listened to your podcast. It inspired me to start a company. Then I started my second. Then I, I met somebody who was on your podcast because I emailed them and told them it's a podcast. That helping people without expectations of return is a unique part of the tech industry and Bay Area culture.

[Jason Calacanis]

You can only experience that by going to the Bay Area and meeting people.

[Jacob]

We found this post. The guy who put a sign on his laptop. I'm going to, I'm going to share it right now. Thanks to producer Jacob, who dug that up. Yeah, a guy put a sign on his laptop.

[Lon Harris]

AI B2B startup raising pre seed product is live. Come say hi. A few investors came up to him. No cold emails, no pitch deck, no

[Jacob]

intro, Just visibility in the right place. So your laptop, love it as a billboard would sort of be the concept there.

[Guest/Co-host]

There you go. All right, people see a coding.

[Lon Harris]

We got a, we got a. What do you want to do? One or two more or you. You're.

[Jason Calacanis]

You're sure?

[Guest/Co-host]

Keep going.

[Lon Harris]

We got a.

[Guest/Co-host]

We Got my energy is good.

[Lon Harris]

Good Question in from one of the live viewers right here on this very live stream we're doing right now from at Yadon 9884, what's the best path for a bootstrap hardware founder, once the prototype is real and nearing profitability, would you stay lean and grind revenue or start bringing in strategic people before you scale up?

[Jason Calacanis]

Yeah, I think you should get investors if you're at that point and investors have totally 180 their position on hardware. It used to be hardware is hard. I don't want any part of it. Now it's hardware is the one of the only moats left. I love hardware. Plaud is doing a great job with that. We just had on the program, somebody made a bookmark that goes into your book and then you can scan it. And Alex was like, over the moon with this product. And I was like, why do I need that? Different strokes for different folks. But hardware is now a way to get lock in.

[Jacob]

Whoop.

[Jason Calacanis]

As a hardware product has some amount of lock in my eight sleep, all of this now has become a moat and a way to increase the fidelity and the usefulness of a product. So, yeah, hardware is no longer a blocker with investors, which is really fascinating to me. I invested in many hardware companies. Terracafe, Cafex, we had a butterfly which was a drop cam, you know, camera ring, competitor didn't work out. We had a smoke detector back in the day before other people came out smoke detectors. You know, most of these things fail and eight Sleep succeeds. It's just Terra Cafe is succeeding really well. Cafe X is still going and be actually doing really well. But hardware is hard and it just takes a little more capital. So you're going to have to find people who are comfortable with investing the capital. And there are now a large number

[Guest/Co-host]

of hardware companies you can work backwards to them. Kickstarter is still like a very viable option. Doing viral ads to get your first thousand customers to give you a thousand dollars and, you know, charging them three or four times what the retail product would be to go first. You get, you know, dummies like me who are like, yeah, I don't care about the price, I just want to be the first to have it.

[Jacob]

Yeah, great.

[Guest/Co-host]

You know, whether it's like the Tesla Roadster that I paid 150k for or countless Kickstarters I've paid for and you know, the boxes are in my closet unopened, or I used it once, it was like, oh, that's interesting. I learned something and Now I move on.

[Jacob]

I wonder if robotics is going to really supercharge this whole thing. Like you're already, you could drop a few grand and get a Chinese humanoid robot at this point. Like soon that's going to be like its own hardware categories, people buying like weird little new robot designs for their house.

[Guest/Co-host]

I think figuring out what to do with commoditized robots is going to be a very interesting business. Yeah, I'm looking forward and I think they ultimately will be a dollar or two dollars an hour is my guess. So if you think about, oh, you

[Lon Harris]

think it is like you don't shell

[Jacob]

out all the money for the hardware

[Lon Harris]

you buy, you pay less.

[Jacob]

And then every month you got to pay your 12.99.

[Jason Calacanis]

If I was making optimus or figure, I would go to Amazon and say, what do you pay somebody to sort packages? They'd say it's $27 an hour. And then fully baked, it's $35 an hour. People sue us for workman's comp, insurance, all this other stuff. And I'd say, okay, we'll give you a figure. Robot, you're currently paying $30 an hour, fully baked, you know, $20 to the person, $10 plus 50% for everything else. We'll give it to you for $4 an hour and we'll have somebody on site who's maintaining them for you. And you have 100 robots here sorting packages for $4 an hour. How does that sound? And they say, great, $4 an hour times 8,000 hours a year. Four times eight, boom. It's going to cost 20, 30, $40,000 a year to have these maintained and ready to go. But then when it goes to consumers, you could really abstract it like a lease. So you'll just pay a $299 a month lease. And that gives you 500 hours of your robot's time. If you go over, it's a dollar extra.

[Guest/Co-host]

Like you lease a car and you go over certain mileage, you pay 50 cents a mile. That will be a really good model for these eventually. And then there are going to be all kinds of applications.

[Jacob]

Great acronym too.

[Lon Harris]

Ass.

[Jacob]

Automatons as a service. It's going to be great.

[Guest/Co-host]

Automatons as a service. Ass. ASS would be your acronym. Yeah, they'll cover your ass.

[Jason Calacanis]

Yeah, I think they're going to be great.

[Guest/Co-host]

I mean, we had a security one, nightscope that had been at like TechCrunch 50 or one of the early launch festivals. One of the early ones that was that weird looking robot that just Drove around. Now there's many of those security robots and I think they were taking the same approach, which is security guards. $20 an hour for them to pay, play Candy Crush and fall asleep. This thing never falls asleep. It works 24 hours and it's $10 an hour. And like, even if it was the same price, it does a better job because it never stops walking around. It's got 360 degree cameras recording everything, which a human's not capable of.

[Jacob]

Accidentally shoot as many people probably, hopefully as the human security guard.

[Jason Calacanis]

But good luck with your hardware startup. You're in. It's good timing. Yeah.

[Lon Harris]

All right, we got, we got a question from Jacob. We got a very spicy question that you're free to punt or we can

[Jacob]

react to some videos. What's your, what's your pleasure?

[Jason Calacanis]

Give me the spicy. And then we'll do a video from

[Lon Harris]

Sean Sully AKA Arugal on X. Out of all the people in Silicon Valley, who's the one person you really

[Jacob]

don't like the most and why?

[Jason Calacanis]

Who don't I like?

[Lon Harris]

One person you don't like. I think you could pick your reason. You disagree with them on things. It's a personality conflict. Whichever. Yeah, you take your pick. I have some, I have some guesses,

[Jacob]

but I'd like to hear your.

[Jason Calacanis]

Well, listen, I, I would say, you know, we all operate in the same ecosystem of users and some people I think have damaged the reputation of the industry and the user base. And then some people have just maybe screwed over friends of mine. So like Zuckerberg, I've been a consistent critic of my number one guest. Personal. It's not personal. It's that every time he had a chance to do the right thing for humanity, he picked his own self interest over that of humanity, whether it's teenage

[Guest/Co-host]

girls or people's privacy or how he

[Jason Calacanis]

worked with partners in his partner program and treated founders. Every single time, time he seemed to make a decision that was not in the best interest of humans, that's it.

[Guest/Co-host]

And so I don't like the way he's behaved.

[Jason Calacanis]

It's not personal.

[Guest/Co-host]

Like, I don't, I haven't seen Zuckerberg in person in a decade.

[Jason Calacanis]

I mean, I might have been at

[Guest/Co-host]

a dinner and been in the same room as him, I'm sure a couple of times.

[Jason Calacanis]

But having sat down and had a

[Guest/Co-host]

conversation with him, I'd be happy to do that and be happy to interview him for a project or a product. But I think he is so obsessed with the growth of his companies, which has made him tremendously successful. That copying other people's ideas, blatantly screwing partners over in the partner program he had. Not being thoughtful about teenagers using his product. Not being thoughtful about, you know, all the reports that he had internally about teenagers and specifically teenage girls and how damaging Instagram was for them in terms of eating disorders and anxiety. And then optimizing all these platforms to keep you online is. It just. It's a level of selfishness in decision making that and cutthroatness that I understand, but that, you know, I wouldn't do and I think has damaged the reputation of the tech industry. I think he actually has made people look at the tech industry and be

[Jacob]

like, ugh, you know, Well, I mean we've.

[Guest/Co-host]

Sam Altman I don't like because he screwed Elon and Elon's my friend and I watched it happen, but I kind of liked it Sam, or I did like Sam intrapersonally. We always had some like interesting things. But he, you know, he kind of shiv'd my friend and I'm team Elon. Not cool to what he did to him. And listen, I'm not the only person who thinks like, hey, maybe Sam should not behave this way on a business level. But again, it doesn't matter. In business you can be incredible. The two people I'm talking about are two of the most successful people ever in the history of business.

[Jacob]

Yeah, they're doing all right.

[Guest/Co-host]

So in some ways being able to make self interested decisions and not worry about what people think about you and not worry about losing and burning relationships is a quick path to extraordinary success.

[Jacob]

Yes.

[Lon Harris]

I think being a, being a like

[Jacob]

high level tech CEO definitely self selects for some of those qualities that we would associate with, you know, like someone

[Lon Harris]

who you might consider like a jerk

[Jacob]

or a not, not very nice person in your life.

[Jason Calacanis]

I mean the number of people who. In that piece in the New Yorker, which, you know, listen, I. These press pieces, like it's probably, you know, 60% true, 40% true, 80% true, who knows? And then people have agendas so you have to sort that out. And the press doesn't care about sorting out the agendas they care about. Like, hey, is this piece going to rip or not? Right? So I don't. The New Yorker piece on Sam was brutal and a number of people called his behavior sociopathic. I didn't call his behavior sociopath. That's what, you know, Ronan Farrow and his collaborator. I didn't participate in that piece. They asked me to. I was like, you know, I don't really have any business interest with Sam, so, like, I'm not qualified. And then number two, I don't talk to the press, so I'm good, thanks. But they were like, we had specific questions to ask you about Sam Altman, about the Sequoia Scouts program. I was like, yeah, feel free to put them in writing and I'll consider. And they're like, we don't do that. And I was like, just.

[Guest/Co-host]

I just didn't respond.

[Jason Calacanis]

I don't care.

[Guest/Co-host]

You know, I just was interested in what the questions were.

[Jason Calacanis]

I probably wasn't going to answer them

[Guest/Co-host]

anyway, but I was curious, like, what.

[Jason Calacanis]

What the question even was.

[Guest/Co-host]

Yeah, yeah.

[Lon Harris]

I mean, when you're writing a piece.

[Jason Calacanis]

So anyway, that's the answer.

[Jacob]

There you go.

[Jason Calacanis]

Fair enough.

[Jacob]

I think.

[Guest/Co-host]

And it's not personal.

[Jason Calacanis]

Like, so, you know, everybody wants to make a person. Like, I'll bring up maybe the guy with the. The guy in military tech, you know, like when I made. When I popped off my answer about him.

[Jacob]

Yeah.

[Jason Calacanis]

It's not that I dislike him. I just thought what he did was brain dead, like, stupid, like to do covert stuff. Now, is the press story correct or not? I don't know if that press story was correct. And I did kind of pop off and I apologized to him because, yeah, I look back on it and I was like, yeah, maybe I was a little bit too hardcore in my answer, but if that story was true, I do think he did the wrong thing, but I didn't have to say it

[Guest/Co-host]

as brutally as I said it.

[Jason Calacanis]

And I did kick him when he was down.

[Guest/Co-host]

He got fired.

[Jason Calacanis]

I was kicking him. So I kind of looked at it and I was like, yeah, maybe that was not a classy or kind or Christian thing for me to do. So I was like, yeah, okay, I take ownership of that. Sure. I kicked a guy when he was down.

[Lon Harris]

When you podcast every day, we shouldn't have done that.

[Jacob]

When you podcast every single day, you're just reacting. You're doing hot takes. It. Can you get caught up in the moment?

[Jason Calacanis]

I think, well, but you see how I do it. Like, we were doing a recording before this and people were asking me about a case and, you know, oh, Y Combinator and General Catalyst supporting a founder who allegedly did things that were unethical and copied another startup. And I went like, I framed it like, if this is true, and we don't know if it's true, this would be maybe unethical, but not illegal behavior. And maybe General Catalyst didn't know what this founder was doing if it's even true. And maybe they're trying to clean it up right now. So I really think through before I pop off and I just don't trust the media or any report now.

[Guest/Co-host]

And when you hear me on all in, sometimes people just run with a Kane koa the great story or some viral clip and I'm like, just so we know, that viral clip could be AI, it could be an old clip.

[Jason Calacanis]

Nobody knows.

[Guest/Co-host]

So this is alleged and I kind of make a joke about it.

[Jason Calacanis]

Allegedly, perhaps not confirmed.

[Guest/Co-host]

I put all those disclaimers on it because I'm old enough now to know.

[Jason Calacanis]

Like.

[Guest/Co-host]

Like I don't some non zero like low double digit percentage of the time I'm reporting on a news story. It's not exactly accurate.

[Lon Harris]

I think that's a good lesson for

[Jacob]

even if you're not hosting a podcast, even just in your everyday life in

[Lon Harris]

2026, you gotta take that beat. It might be very satisf be like, oh, this, this idea story lines up with my personal biases. I can't wait to share it and

[Jacob]

prove how right I've been.

[Lon Harris]

You always have to take that extra beat. Like, is this AI? Is this true? Is there a community note? Is there some additional information? Is this being framed in a certain

[Jacob]

way, designed to provoke as everything is?

[Jason Calacanis]

This was your first trip to Italy?

[Lon Harris]

This was my first time ever in Italy.

[Jacob]

Yes, that's true.

[Jason Calacanis]

Okay, so I went to Greece. Oh, you didn't went to Greece.

[Jacob]

Mykonos. I visited Santorini and Amazing. It was amazing.

[Jason Calacanis]

So give me your general impression of Greece and Italy. What were your favorite parts of it? What was extraordinary and then what was underwhelming and didn't hit the notes as we go off duty here. So I was lawn off duty in Italy.

[Lon Harris]

I went, I did a week in in Rome. Me and a friend, we stayed in an Airbnb right by the Castell San Angelo. Right. Right at sort of the middle of the city, right, you know, not far from Trastevere. The staying in the Airbnb was amazing. We're walking distance from the Vatican. It's a building from the 1600s where the Pope's staff used to live in

[Jacob]

like the Renaissance era.

[Lon Harris]

So it was an unbelievable place. The best thing we did was that Crypt tour. We did a golf cart crypt tour

[Jacob]

and a guy took all sorts of like out of the way, you know,

[Lon Harris]

sort of like churches that had, you know, bone temples in the basement and

[Jacob]

all of this crazy art that was amazing to see.

[Lon Harris]

We took a Bullet train one day to Florence and with. To the Uffizi Gallery.

[Jacob]

We went to this amazing pasta restaurant called Osteria Pastela that was.

[Jason Calacanis]

I think I went to both of those. That's great.

[Lon Harris]

Yeah, they're one of the places they, they take a huge wheel of cheese and they pour brandy in it and then they light it on fire and then they mix your pasta in the cheese bowl and then they topped it with white truffles.

[Jacob]

It was incredible.

[Lon Harris]

And the efficiency, you know, lots of great art. I will say a down thing.

[Jacob]

It's very, very crowded right now in Italy. Lots and lots of tourists want to see Rome and Florence. I was not alone.

[Lon Harris]

And one thing that really bugged me in all the art museums that we went to is people are standing in front of the paintings of the sculptures and they're just snapping photos on their phone. And I mean, this is like Botticelli's Birth of Venus, Caravaggio's Medusa. Just go on Google Images. There's a hundred beautiful up close high resolution photos of every. You could get the Birth of Venus on like a mouse pad. Like, you don't need your own photo.

[Jason Calacanis]

I think this is a, this is a gripe. This is a gripe that's worth noting. Yeah. Like, and just be in the moment, folks. Just be in the moment. And this, I'll tell you the thing that makes me crazy in these places. The selfie stick or the i360 guy. You know the i360 guy with the stick.

[Lon Harris]

They're, they're all.

[Jason Calacanis]

And it goes up.

[Jacob]

Yeah.

[Jason Calacanis]

And he's got to walk around and he's got to have a 360 view that he's never going to look at. But the 360 guy is worse than the selfie guy. Yeah, the selfie guy's got his iPhone on the stick. Whatever. These guys are walking through Vegas casinos and I'm like, what are you documenting? Your life is incredibly boring. You're the least important person within 100 miles of this place. This place has been documented, as you correctly point out, to the point of absurdity. And now everybody's gotta be on your i360 and you're smacking people in the head. Nobody cares. You're never looking at these things. If you want to take a quick photo of yourself in front of your favorite piece, totally fine.

[Guest/Co-host]

Right?

[Lon Harris]

And that's. I did, I posted a few of them to Twitter. I would take a picture of these. Like, here I am, I'm in the Uffizi. I want to remember this moment. I'm not saying don't be a tourist, don't take a photo, don't take a selfie. But it's that stand, just, just taking it. And like we went to a Rothko exhibit as well in Florida. It's like a modern museum and it's like those paintings, it's being in the room with it, that's the point. It's overwhelming when you're standing in front of it. You're not going to appreciate it on your phone. What are you doing?

[Guest/Co-host]

So that, that here's my idea, here's my idea for these museums. 24 hours and increase the price to go a little bit. Yeah, so.

[Jason Calacanis]

Or maybe like on the off hours

[Guest/Co-host]

you pay a premium.

[Jacob]

Oh sure.

[Jason Calacanis]

I would like.

[Guest/Co-host]

Because these all close at six o', clock, right? They're done.

[Lon Harris]

Yeah, it's like Ufizi, I think is. Yeah, it's like 10am to like 4:30. But you have to get a time. They send you through in shifts. So when you buy your tickets they give you a time to show up and then you get in the.

[Jason Calacanis]

And there's like a VIP line. You pay an extra couple of euro euros. So what did you pay, €10 or something? It's not expensive.

[Lon Harris]

No, it was, I think it was like €30 a piece. But we also made those plans a little last minute. I bet if we got it earlier

[Jacob]

we probably could have gotten a cheaper Ufizi pack.

[Jason Calacanis]

Here's my idea. Yeah, the place closes like the Last entrance is 4:30, which means they're kicking you out at 6.

[Jacob]

Right?

[Jason Calacanis]

6 to 8, 8 to 10, 10 to 12, 12 to 2, 6am to 8am I know. Maybe people don't want to work those have a hundred euro experience now. €100, $100 experience per person. Sounds insane. But by the way, if you're an Uber driver or you're a housekeeper in New York, you're making 30, 40, 50 bucks an hour already. And that person might want to have an experience with 10% as many people there or 20% as many people there.

[Jacob]

It would be a totally different experience to go and really like soak it in on your own and have the time instead of being pushed and everybody's trying to push.

[Jason Calacanis]

I would have loved, loved to go to dinner and then I like to do my after dinner walk because I'm old and I'm controlling my weight. Road co twist. I would love to do my two hour walk in the Louvre from 8 to 10pm or even 10 to midnight. How great Would it be for us to be in the Louvre at 11pm and see the Mona Lisa or the Venus de Milo with but a half dozen people there?

[Jacob]

Yeah.

[Lon Harris]

Because also I. Yeah.

[Jacob]

In the British Museum too, in London, I have the same experience where it's

[Lon Harris]

like, it's great, amazing to see that stuff, but you're. You're constantly in like this huge crowd

[Jacob]

and everybody wants to take their photos and it's really.

[Jason Calacanis]

Did you go to the Florence gelato place that I told you about?

[Lon Harris]

You know, I did. I went to a gelato place in

[Jacob]

Florence, but we were only there for 24 hours. I ran out of time. I did not get to. I missed that. I missed that one. But I did.

[Lon Harris]

We did go.

[Jacob]

We got some incredible food. The whole like Rome too. We went to some really amazing restaurants.

[Lon Harris]

And then. So that was week one, and then week two, we joined my dad and

[Jacob]

my uncle and his girlfriend Karen for

[Lon Harris]

a cruise and that went to Santorini, Greece, Mykonos, Greece, and also a town named Kusadashi in Turkey, where there's the ancient Greek ruins of Ephesus are there.

[Jacob]

And so we did a little quick tour.

[Guest/Co-host]

Santorini, Beautiful, right? That hillside with the. Yeah. Did you get to go on the donkey ride?

[Lon Harris]

No.

[Guest/Co-host]

Up and down.

[Lon Harris]

I felt. I felt bad for the donkey. I didn't. I don't.

[Jacob]

I don't want to subject a donkey to my £200. I felt like I'm not going to do that to that.

[Jason Calacanis]

Well, this is why Rocco slash twist will get you down to 180 and you'll be fighting while you're on that. No, I thought the donkey thing was a little bit extreme too, but they have like this very steep hill and you take a donkey ride up it.

[Lon Harris]

Oh, yeah. The. The sort of that it's the city. When you think of Santorini and you see the Instagram post with the white houses in the blue dome, churches, that's oya. And so we got to go check out the town.

[Jacob]

We took a bus to get there

[Lon Harris]

and then we went to Fira as well, another town.

[Jacob]

And then we.

[Lon Harris]

They.

[Jacob]

They took us to one of those black sand beaches. So we got to do a little beach. Santorini. It was incredible. That was. That was.

[Jason Calacanis]

Well, I'm glad you got to take some time off. And this is where I don't have a problem with the metal glasses. Actually, I'm okay, sure. I have an exception for metal glasses. If you take them to dinner, you're not invited to dinner.

[Jacob]

Right.

[Jason Calacanis]

However, if you're in a museum. And you want to put those on and record.

[Jacob]

Go for it.

[Jason Calacanis]

Go for it. It's better than the selfie. Stick everywhere.

[Lon Harris]

I don't think. I still don't think you're really gonna

[Jacob]

get a lot out of that.

[Lon Harris]

After the fact that part of being in the museum is you're there. You're in the museum. It's. It's. It's real. Like, you can look up art on the Internet all the time. I do it all the time.

[Jason Calacanis]

Take ten pictures, okay? Take ten pictures.

[Jacob]

Yeah.

[Lon Harris]

Yourself at the front. Yourself in front of your favorite piece of art that you saw, okay?

[Jason Calacanis]

And nobody's at the cafe having a coffee and whatever.

[Lon Harris]

Thai selfie.

[Jacob]

I took a ton.

[Lon Harris]

But, like, when you're standing in front of a Rothko, you don't need to have your camera. It's just. It's just.

[Guest/Co-host]

What are we doing, folks?

[Jacob]

It's just lines on a canvas, on a photo. You have to.

[Jason Calacanis]

What are we doing?

[Jacob]

Yeah.

[Guest/Co-host]

Yeah. All right, everybody, it's been. Another great twist is in the can. Bye.

[Jacob]

Bye.

[Jason Calacanis]

Mellow.