How do you know whether an iOS app you have built has potential to be big? Getting an email from Steve Jobs is probably a strong indicator.

Ashish Toshniwal, founder of 10Kr and YML (Y Media Labs), started by trying a bit of everything: classifieds, Groupons, and Facebook apps. That email made him quit his job, but as Ashish says, it took him and YML 14 years to become an overnight success. YML helped businesses go mobile-first long before it became a buzzword, with over 45 Fortune 500 clients including Apple, PayPal, Meta, and Disney.

Along the way, Ashish shares the real decisions every founder faces, such as when to take VC money, when to sell, and how to think about repeat business. He also reflects on turning down opportunities like Credit Karma equity (now worth $7billion), showing the tough choices early-stage founders make just to survive and keep their business running.

This is a story about timing, focus, and conviction, and what happens when you build something real: from Calcutta to Silicon Valley, one decision at a time.

0:00 – Trailer
03:24 – How the Co-founders met
05:28 – The first 3 ideas: Classifieds, Groupons & Facebook apps
06:30 – An email from Steve Jobs made Ashish quit his Job
07:59 – Building apps when App Store launched (Apple as a client too)
09:20 – YML was famous but not profitable
10:07 – Becoming the “app guys” of Silicon Valley
11:56 – The pivot: Stick with products or move to services?
13:43 – 6 acquisition offers on the table: Sell or not?
16:57 – The first exit: 60% acquired at $60M
18:38 – “We’d never seen that kind of money”
19:26 – IOS engineering was like AI engineering
20:13 – “If we don’t have repeat business, we don’t have business”
22:09 – Silicon valley is not a zipcode, it’s a mindset
23:54 – Clients came for design, stayed for engineering
26:11 – Does motivation change when equity shrinks?
29:01 – Firing and re-hiring yourself as founder CEO
30:50 – Why the final decision to sell YML was made
32:55 – The golden window of mobile
34:26 – Could YML have been a billion-dollar company?
37:34 – Turning down Credit Karma equity: now worth $7B
38:39 – Why CEOs are like travel agents
41:50 – Why Ashish invested in Neon
44:22 – What wealth truly enables
47:36 – Investing early in Tesla, Nvidia, and Meta
49:07 – Why founder-led companies outperform in public markets
50:54 – It’s easy to build products, harder to build real businesses
52:44 – If your product isn’t 10x better than ChatGPT, you have no chance
53:04 – The future of jobs: 5 roles merging into 2 with agents on top
57:25 – ChatGPT will not go after human-in-the-loop
59:35 – The first real challenge to Google’s dominance
1:01:59 – Building AI agents that do real work is incredibly hard

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Connect with Siddhartha on:
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Twitter: https://x.com/siddharthaa7

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$350M by Building Apps for iphones when IOS was like AI | Ashish Toshniwal, Calcutta -> Silicon Valley

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