Welcome back to Two Founders Podcast! Today we talk about the shocking acquisition of Airtable and the top three mistakes startups make when it comes to sales. Of course Matteo also brings a LinkedIn Nugget - should you have an AI on the board? And Anna has received a listener question - should I keep my day-job or jump and do the startup full time?

— Anna’s topic —

Anna gives her list of the top three sales mistakes startups do:

→ Don’t do a free pilot! - Well, it depends - what is the plan after that? What is your relationship 3 years later?

→ Put your price higher! - You don’t know this yet, but probably you can charge more.

→ Keep any material for yourself! - Don’t send any material, book a meeting instead.

— Matteo’s topic —

Matteo talks about the Milan company Bending Spoons’ acquisition of Airtable.

→ Why did Airtable go from a $11B valuation to finally selling for only $1.3B?

→ Was the issue growing too slowly, being overvalued or not reacting quick enough to the vibe-coding entering the market?

— Linkedin Nugget —

Should you have an AI-board member?

Matteo brings the new Linkedin hot topic of letting AI have a seat at the board.

— Listener Question —

Should I keep my day-job or jump and do the startup full time?

Listener Casper has just raised, and is wondering if he should quit his current full time job and go all in for the startup he is building. Matteo pushes for staying, and Anna is definitely team leave.

— Timestamps —

00:00 Intro

01:14 Why you shouldn’t do a free pilot

05:29 Why startups price too low

09:45 Why you shouldn't show your demo too early

13:47 Bending Spoons & the Airtable acquisition

16:18 How Airtable went from $11B to $1.3B

21:34 What startups can learn from Airtable

26:06 Should AI have a seat on your board?

30:31 AI as the memory of a company

34:08 Should you quit your job to build a startup?

38:02 The final verdict: go all-in?

Subscribe to the Two Founders Podcast, we talk about startups and specifically about sales, based on our own experience of building a startup from 0-1, and finally landing an acquisition.

#Startup #Entrepreneurship #Sales #B2BSales #AI #SaaS #Founders #VentureCapital #Airtable #BendingSpoons

In this episode of The Two Founders Podcast, Anna Nilsson and Matteo Ghetti unpack some of the biggest stories shaping startups, AI, sales, and venture capital.

They discuss Google’s massive stock drop and its $200B AI spending plan, the pressure on Gemini to catch up with ChatGPT and Claude, and what the semiconductor market might tell us about the future of AI.

They also dive into the booming defense startup ecosystem: how companies can sell to the military, why government contracts take so long, why domain expertise matters, and what founders should know before entering the space.

Plus, former Uber CEO Travis Kalanick is back with Atoms, a bet on physical AI, automation, mining, and kitchens. The conversation explores why robotics could be the next major frontier—and why automating the final 20% is much harder than it looks.

And finally: AI-generated content on LinkedIn, why “AI slop” is becoming a problem, and a founder question about whether you should ever offer a free pilot to a potential customer.

A conversation about AI, startups, venture capital, defense, robotics, sales, and the realities of building companies.

Watch on YouTube: https://youtu.be/CNunws5iKPg

Follow Anna:

LinkedIn: https://www.linkedin.com/in/anna-fm-nilsson/

Instagram: https://www.instagram.com/anna.fm.nilsson/

TikTok: https://www.tiktok.com/@anna.fm.nilsson

Follow Matteo:

LinkedIn: https://www.linkedin.com/in/matteo-ghetti/

Microsoft just lost $650 billion in market value after investors questioned whether the company is actually delivering on its AI promise. But what does Microsoft’s story have to do with startups?

In this episode of the Two Founders Podcast, Anna and Matteo discuss:

• Why Microsoft’s AI narrative may have gotten ahead of reality

• What the market expects from Microsoft, Copilot, Azure and OpenAI

• Why startups need to deliver on the promises they make

• Who the world’s top angel investors are and what they have in common • Why many successful angel investors were operators and founders themselves

• Whether you should start selling your startup before your product is finished • Why talking to customers early can be more valuable than building the “perfect” MVP

• How to structure pilots and payments when your product is still evolving

• Why branding and building an online presence can make startup sales easier

The big lesson? A compelling story can get you attention—but eventually, the story has to match reality.

And for founders: go out there and sell.

🎙️ Welcome to Two Founders, where we talk startups, sales, company building, investors and the lessons we learn along the way.

Subscribe: https://dashboard.rss.com/podcasts/twofounderspodcast/

Follow Anna: https://www.linkedin.com/in/anna-fm-nilsson/ https://www.instagram.com/anna.fm.nilsson/

Follow Matteo: https://www.linkedin.com/in/matteo-ghetti/